Cottonseed as Protein, Moving Up the Food Chain

by Alex Owre

The white lint that is spun into cotton yarn constitutes roughly a quarter
of the raw plant matter sucked into a cotton stripper. Over the years,
U.S. producers have learned to squeeze maximum value out the rest,
especially the seeds. For every pound of fiber, 1.6 pounds of seed are
produced. Once considered garbage and dumped in streams, cottonseed
has long been used as cattle feed, fertilizer, and in countless industrial
applications.

Cottonseed oil comprises about 16% of a seed, by weight; is a well-

known ingredient in many processed snack foods; and is the most
valuable cottonseed product. Current EPA regulations classify it as safe
for human consumption after it has been refined to remove volatile
compounds such as monoglycerides, some pigments, free fatty acids, fatty
oxidation products, pesticide residues and other undesirable compounds.1

Once most of the oil has been removed, the meal, the second most
valuable product of cottonseed, is used principally as livestock feed.
Constituting nearly half of a seed’s weight, the meal contains 23% of
a high biological-value protein.

Today, nearly 10% of U.S.-produced meal goes to fish farms, where some
species thrive on it. Fish farmers praise it as a cheap, highly nutritious
alternative to fish meal, which is composed primarily of wild-caught
marine species, the price of which continues to climb as natural fish
stocks dwindle.

In October, the National Organic Standards Board voted to consider

developing organic standards for some farm-raised fish species, while
unanimously voting against creating national organic standards for wild-
caught fish. Some argue that this could put aquaculturists at a
disadvantage to the beef and poultry industries, which are now eligible
for organic labeling.

But cottonseed might provide a loophole. In a recent study funded by the

National Cottonseed Products Association and the Cotton Foundation,
 Ohio State University researchers replaced fish meal protein with
cottonseed meal protein in up to 100% of the diet of rainbow trout
(“Plant-Based Meal Paves Way for "Organically-Grown" Fish,”
OSU Extension). The growth of the fish was unaffected by the switch, so
the researchers suggest that cottonseed meal could replace fish meal as
the main protein source of species such as trout, making them eligible for
organic labeling.

Most fish and other non-ruminant animals, including humans, cannot eat
cottonseed because it contains a toxin called gossypol. When eaten by
people, this polyphenolic anti-nutrient damages the heart and liver.

For years, scientists have tried to breed cotton with gossypol levels safe
for consumption. In the 1950s they succeeded, but because the toxin was
missing from leaves as well as seeds, the plants proved defenseless against
pests. But last November – via a new technique called RNA
interference, or RNAi, a gene-silencing mechanism for which its
discoverers Andrew Fire and Craig Mello won the 2006 Nobel Prize for
Medicine – researchers at the Texas Agricultural Experiment Station
succeeded in lowering the gossypol level in seeds while sparing the rest of
the plant.

The result of this experimentation (partially funded by Cotton

Incorporated) is being hailed by the cotton industry and biotechnologists
as a breakthrough in the struggle against world hunger. According to Dr.
Keerti Rathore2, one of the Texas researchers, the current level of 44
million tons of cottonseed produced globally each year, containing 22%
high-quality protein, could feed 500 million people. Studies in animals,
including humans, using gossypol-free, glandless cottonseed flour, have
shown that cottonseed protein promotes growth, weight gain, and a
positive nitrogen balance (less N is excreted through urine, feces and
sweat than is taken in). Researchers are already experimenting with
lowering gossypol levels in indigenous African cotton strains, as well as
employing RNAi technology on other crops with toxic components, such
as fava beans.

Solution to Hunger … or Diversion?

Industry estimates put the time-to-market for low-gossypol cotton at 10

years. Scientists maintain that cotton farmers in poor countries will
doubly benefit from a crop that can be sold for food (or be eaten directly)
and clothing. Supporters of genetic engineering hope that the prospect of
“feeding the world” with cotton will win over skeptics and change
policies of those poor countries that are, so far, resisting the pressure to
give in to genetically engineered (GE) crops.

Environmentalists remain wary, citing the example of golden rice,

genetically engineered to contain vitamin A but requiring consumption of
huge amounts to derive any benefit. (Furthermore, fields that are not
clean cultivated usually contain edible greens that are rich in vitamin A
and other nutrienets.) Edible-seed variety cotton will not solve the
problems of GE foods, environmentalists maintain, but will exacerbate
them. Zachary Makanya, in his excellent article for Seedling Magazine
(August 2004, www.grain.org/seedling/?id=294)), explains why GE crops
have no place in African agriculture (a target market for low-gossypol
cotton). GE crops –

1. will contaminate non-GE crops; co-existence is not possible;

2. will foster dependence on a corporate seed supply;
3. will usher in “Terminator” and “Traitor” technologies;
4. will increase the use of chemicals;
5. are patented;
6. favor industrial agricultural systems;
7. threaten organic and sustainable farming;
8. require biosafety systems unrealistic for African countries;
9. will not reduce hunger in Africa;
10.will not resolve problems with pests;
11.will encourage arbitrary destruction of biodiversity;
12.are a threat to human health.

Says Sue Mayer, director of GeneWatch UK: “Poverty and hunger are
complex problems caused by bad government, poor economies and war.
It is not just a matter of finding a new wonder plant.”

Concerning cottonseed as fish meal, the problem of crashing ocean

populations will put into perspective any satisfaction we derive from fish
that will eat, and even thrive, on cotton’s protein. As fish meal,
cottonseed might open new channels of discussion around organic food
labeling, but as human food, is the science of edible cottonseed a red-
herring in the real struggle to feed the world’s poor?
 1. Environmental Protection Agency
40 CFR Part 185 [OPP-300335A; FRL-5357-7]
Revocation of Pesticide Food Additive Regulations

2. http://www.pnas.org/cgi/content/abstract/103/48/18054
Engineering cottonseed for use in human nutrition by tissue-specific
reduction of toxic gossypol
Ganesan Sunilkumar, LeAnne M. Campbell, Lorraine Puckhaber ,
Robert D. Stipanovic , and Keerti S. Rathore.

Read Alex Owre's article about cotton from a previous issue:

King Cotton and the Wal-Mart Shopper (Winter 2006-2007)

Research Project: New and Expanded Uses of

Oilseed Products and By-Products Project Team

Location: Commodity Utilization Research Dowd, Michael -

Mike
Title: COTTONSEED EXTRACTION WITH
Kuk, Myong - Sam
MIXTURES OF ACETONE AND HEXANE
Dailey, Oliver
Authors Klasson, Kjell
Kuk, Myong
Tetlow, R
Dowd, Michael
Submitted to: Journal of the American Oil Publications
Chemists' Society
Publication Type: Peer Reviewed Journal Publications
Publication Acceptance Date: February 15,
2005
Publication Date: May 1, 2005
Citation: Kuk, M.S., Tetlow, R., Dowd, M.K. Related National
2005. Cottonseed extraction with mixtures of Programs
acetone and hexane. Journal of the American
Oil Chemists' Society. 82(8):609-612. Quality and
Interpretive Summary: Cottonseed meal and Utilization of
oil are produced from cottonseed by solvent Agricultural
extraction. Although cottonseed meal is Products (306)
valuable as animal feed, the use of cottonseed
meal is limited by the toxicity of gossypol.
Commercial hexane, currently used for
extracting oil from cottonseed, does not Related Projects
efficiently extract gossypol. Hence, the
cottonseed meal produced by extraction with Derivatization of
commercial hexane has a small amount of Gossypol for Value-
gossypol. In comparison, pure acetone is known Added Utilization
to efficiently extract oil and gossypol from
cottonseed. Although the cottonseed meal Value Added Uses
produced by pure acetone contains a negligible of Cottonseed
amount of gossypol, the meal has a detrimental Products
odor, known as "catty odor." SRRC scientists
found that adding small amounts of acetone (up
to 25%) to hexane significantly increased
extraction of gossypol from cottonseed flakes.
The SRRC scientists also found that a mixture
of acetone/hexane with 10% acetone can be
used to efficiently extract oil and gossypol from
cottonseed, and produce cottonseed meal
without "catty odor." The research directly
benefits the U.S. farmers who grow cotton, and
indirectly the oilseed processing industry which
are involved in producing cottonseed meal and
edible oil.

Technical Abstract: Cottonseed flakes were

extracted with mixtures of n-hexane and
acetone with the concentration of acetone
varying between 10 and 75%. Adding small
amounts of acetone (<25%) to n-hexane has
significantly increased the extraction of free
and total gossypol from cottonseed flakes.
Sensory testing detected no difference in the
odor of cottonseed meals of those produced
either by extraction with 100% n-hexane or by
extraction with a 10/90(v/v)% of
acetone/hexane. More than 80% the free
gossypol was removed by the 10/90%
acetone/hexane extraction mixture. A solvent
mixture containing 25% acetone removed
nearly 90% of the free gossypol that was
removed by extraction with pure acetone and
had only a minimum increase in meal odor. In
contrast, cottonseed meals produced by
extraction with pure acetone had a much
higher odor intensity. The composition of the
cottonseed crude oil was insignificantly affected
by the acetone concentration of the extraction
solvent.
Cottonseed extraction with a new solvent system: Isohexane and alcohol
mixtures
Authors: Kuk, M.1; Hron, R.
Source: Journal of the American Oil Chemists' Society, Volume
75, Number 8, August 1998 , pp. 927-930(4)
Publisher: Springer

• < previous article

• next article > |
• view table of contents

Key:
- Free Content
- New Content
- Subscribed Content
- Free Trial Content
Abstract:
A solvent system, consisting of isohexane and 5 to 25% alcohol, either
ethanol (EtOH) or isopropyl alcohol (IPA), was tested for extracting
gossypol and oil from cottonseed. The test results indicate that this new
solvent system not only is effective in removing free and total gossypol
but also is as efficient as n-hexane when extracting oil. The amino acid
analysis of cottonseed meal, produced by the new solvent system, is
similar to that produced by commercial n-hexane. Present commercial
cottonseed extraction and downstream processing of cottonseed oil
refining may need little change to adopt this new solvent system. This
new solvent system may lead to a solution to the gossypol problem of
cottonseed extraction.
Keywords: Cottonseed; extraction; free gossypol; meal; new solvent;
oil total gossypol
Document Type: Research article
DOI: 10.1007/s11746-998-0268-4
Affiliations: 1: Email: mskuk@nola.srrc.usda.gov

Titre du document / Document title

Ethanol extraction of oil, gossypol and aflatoxin from cottonseed
Auteur(s) / Author(s)
HRON R. J. ; KUK M. S. ; ABRAHAM G. ; WAN P. J. ;
Affiliation(s) du ou des auteurs / Author(s) Affiliation(s)
ARS, SRRC, New Orleans LA 70719, ETATS-UNIS
Résumé / Abstract
Commercial processing of cottonseed requires hexane to extract and
recover edible oil. Gossypol and aflatoxin are not removed from
extracted meals. A bench-top extraction process with 95% (vol/vol)
aqueous ethanol (EtOH) solvent has been developed that extracts all
three of the above materials with a much less volatile solvent. In this
process, cottonseed is pretreated and extracted with ambient 95%
EtOH to remove gossypol and then extracted with hot 95% EtOH to
extract oil and aflatoxin. Membranes and adsorption columns are used
to purify the various extract streams, so that they can be recycled
directly. A representative extracted meal contained a total gossypol
content of 0.47% (a 70% reduction) and 3 ppb aflatoxin (a 95%
reduction)
Revue / Journal Title
Journal of the American Oil Chemists' Society (J. Am. Oil Chem. Soc.)
ISSN 0003-021X
Source / Source
1994, vol. 71, no4, pp. 417-421 (28 ref.)
Langue / Language
Anglais
Editeur / Publisher
Springer, Heidelberg, ALLEMAGNE (1947) (Revue)
Mots-clés anglais / English Keywords
Cottonseed meal ; Cottonseed oil ; Solvent extraction ; Ethanol ;
Chemical contamination ; Aflatoxin ; Gossypol ;
Mots-clés français / French Keywords
Farine coton ; Huile coton ; Extraction solvant ; Ethanol ;
Contamination chimique ; Aflatoxine ; Gossypol ;
Mots-clés espagnols / Spanish Keywords
Harina algodón(semilla) ; Aceite algodón ; Extracción solvente ;
Etanol ; Contaminación química ; Aflatoxina ; Gosipol ;
Localisation / Location
INIST-CNRS, Cote INIST : 204, 35400004538725.0120

Copyright 2007 INIST-CNRS. All rights reserved

--------------------------------------------------------------------------------------------
-------------------------------------------------------------------------------------------
Title:
Extraction of gossypol from cottonseed
Document Type and Number:
United States Patent 5112637
Link to this page:
http://www.freepatentsonline.com/5112637.html
Abstract:
The present invention is drawn to a process for extraction of gossypol
for cottonseed using a solvent solution which includes: (a) a water
miscible organic solvent; (b) water; and (c) an acid which is strong
enough to prevent binding of gossypol to cottonseed protein but which is
not so strong as to hydrolyze a substantial portion of the cottonseed
protein. The present invention also includes cotton seed meals of
reduced gossypol content (and optionally reduced aflatoxin and/or fat
content) produced by the aforementioned extraction.
Inventors:
Hron Sr., Robert J. (New Orleans, LA)
Abraham, George (Metairie, LA)
Kuk, Myong S. (Metairie, LA)
Fisher, Gordon S. (Metairie, LA)
Application Number:
07/608786
Filing Date:
11/05/1990
Publication Date:
05/12/1992
View Patent Images:
Images are available in PDF form when logged in. To view PDFs,
Login or Create Account (Free!)
Referenced by:
View patents that cite this patent
Export Citation:
Click for automatic bibliography generation
Assignee:
Agriculture US. (US)
Primary Class:
426/629
Other Classes:
426/430, 554/13, 426/486, 426/331, 554/11
International Classes:
A23K1/14; A23L1/211; C11B1/10; C11B1/00; A23B9/16
Field of Search:
426/486, 426/629, 426/656, 426/622, 426/430, 426/331, 260/412.4
US Patent References:
October, Preparation of cottonseed
2615808 Rice 260/412.4
1952 meal
August, Production of cottonseed
2950198 King et al. 426/417
1960 meal of improved quality
Process for recovery of
November,
3062876 Pons et al. 260/520 gossypol from cottonseed
1962
gums
METHOD AND
March, APPARATUS FOR THE
3432529 Depmer 260/412.4
1969 EXTRACTION OF OIL
FROM COTTONSEED
January, Don, Jr. et
3557168 260/412
1971 al.
PROCESS FOR
October, PRODUCING
3615657 Gastrock 426/486
1971 COTTONSEED PROTEIN
CONCENTRATE
Use of acidic hexane to
March,
3941764 Hensarling 426/656 process oil seeds for protein
1976
and oil
Process for producing an
August,
3972861 Gardner 426/656 edible cottonseed protein
1976
concentrate
Method for extracting
February,
4072671 Sodini 426/634 phenols and oligosaccharides
1978
from vegetable tissues
Method of producing edible
4084007 April, 1978 Hipp 426/430
meal from cottonseed
 February, Process for treating
4139646 Gastrock 426/430
1979 cottonseed meats
Method for the extraction of
undesirable and/or toxic
4148928 April, 1979 Sodini et al. 426/430
glucosidic compound from
vegetables
Process for producing a low
4201709 May, 1980 Kadan 426/430 gossypol protein product
from glanded cottonseed
Extraction of cottonseed and
August, Kadan et
4219469 260/123.5 concentrates to improve the
1980 al.
color of protein isolate
Process for extracting
November, Karnofsky oleaginous seed materials
4359417 260/235
1982 et al. particularly cottonseed with
aqueous alcohol
Method of producing low-
October,
4546004 Rhee 426/629 gossypol cottonseed protein
1985
material
Removal of toxins from
4747979 May, 1988 Gimber 260/412.4
cottonseed
Other References:
Canella et al, Journ. of Food Science, 42:1218-1219, 1977.
Abov-Donia et al, "High-Performance Liquid . . . ", Journal of Chrom.
206 (1981) 606-610.
English Language abstract of German Offen 2,606,961, 9 Sep. 1976.
English Language abstract of Spanish patent 445,653, 01 Jun. 1977.
Abstract of: M. Canella et al, "Functional Properties . . . " Riv. Ital.
Sostanze Grasse 1977, 54(2), 73-6.
Abstract of: G. Sodini et al, "Effect of . . . " Riv. Sci Technol. Alimenti
Nutr. UM 1976, 6(4), 219-21.
Abstract of German Offen 2,631,695, 26 Jan. 1977.
Primary Examiner:
Paden, Carolyn
Attorney, Agent or Firm:
Sadowski, David R.
Silverstein, Howard M.
Claims:
What is claimed is:

1. A process for extraction of gossypol from cottonseed, which process

comprises:

(a) contacting cottonseed with a solvent solution comprised of: (i) a

water miscible organic solvent; (ii) water, and; (iii) an acid which is
characterized as being strong enough to prevent binding of gossypol to
cottonseed protein, but not so strong that it will hydrolyze a substantial
portion of said cottonseed protein; under conditions providing
extraction of gossypol from said cottonseed by said solvent solution,
thereby producing cottonseed meal of reduced gossypol content and
solvent solution having gossypol therein; and

(b) separating said cottonseed meal of reduced gossypol content from

said solvent solution having gossypol therein.

2. The process of claim 1 wherein said water miscible organic solvent is

selected from the group consisting of alcohols, esters, ethers, nitriles and
mixtures thereof.

3. The process of claim 2 wherein said water miscible solvent is a C1 to

C3 monohydric alcohol.

4. The process of claim 3 wherein said water miscible alcohol is ethanol.

5. The process of claim 3 wherein said step of contacting is carried out

with a weight ratio of solvent solution to cottonseed of from about 15 to
1 to about 1 to 1.

6. The process of claim 1 wherein said cottonseed meal of reduced

gossypol content is rinsed with fresh solvent after said step of
contacting.

7. The process of claim 6 wherein said fresh solvent includes a water

miscible organic solvent selected from the group consisting of alcohols,
esters, ethers, nitriles and mixtures thereof.
8. The process of claim 1 wherein said solvent solution has a pH of from
about 2 to about 5.

9. The process of claim 8 wherein said solvent solution has a pH of from

about 2 to about 4.

10. The process of claim 1 wherein said acid is a tribasic inorganic or

organic acid.

11. The process of claim 10 wherein said acid is selected from the group
consisting of citric acid, ascorbic acid, phosphoric acid, and mixtures
thereof.

12. The process of claim 1 wherein said step of contacting is carried out
with a weight ratio of solvent solution to cottonseed of from about 1 to 1
to about 1 to 1.

13. The process of claim 1 wherein said cottonseed and said solvent
solution, contain a total of from about 2 to about 32 wt. % water.

14. The process of claim 13 wherein said cottonseed and said solvent
solution, contain a total of from about 4 to about 12 wt. % water.

15. A cottonseed meal of reduced gossypol content produced by the

process of claim 13.

16. The process of claim 1 wherein said step of contacting is carried out
at a temperature from about 50° C. to about 90° C.

17. The process of claim 1 which is practiced at pressures up to about 60

psig and temperatures up to about 130° C.

18. The process of claim 1 which is practices at pressures of about 3 to

about 10 psig and temperatures from about 80° C. to about 90° C.

19. A cottonseed meal of reduced gossypol content produced by the

process of claim 18.

20. The process of claim 1 wherein said step of contacting removes

aflatoxins from said cottonseed.
21. A cottonseed meal of reduced gossypol and reduced aflatoxin
content produced by the process of claim 20.

22. The process of claim 1 wherein said cottonseed is full fat, and said
step of contacting extracts fat from said cottonseed.

23. A cottonseed meal of reduced gossypol and reduced fat content

produced by the process of claim 22.

24. The process of claim 1 wherein said cottonseed is wholly or partially

defatted prior to said step of contacting.

25. A cottonseed meal of reduced gossypol content produced by the

process of claim 1.

26. A cottonseed meal of reduced gossypol, aflatoxin and fat content

produced by the process of claim 1.

Description:

FIELD OF THE INVENTION

This invention relates to a solvent extraction process for removing

gossypol (a toxic pigment) from cottonseed. The extraction is conducted
with a solvent solution comprised of: a water miscible organic solvent,
water and an acid which is strong enough to prevent gossypol from
binding to cottonseed protein, but not so strong that it hydrolyses a
substantial amount of the cottonseed protein.

BACKGROUND OF THE INVENTION

Unlike other commercial oilseeds, cottonseed contains a toxic pigment,

gossypol, which prevents it from being a feed for animals, other than
those that have a rumen. That is, while some whole cottonseed is fed to
mature ruminants, most of it is separated into oil and meal, typically by
solvent extraction using hexane. As used herein, cottonseed meal, or
flour, refers to the whole residue remaining after most of the oil has
been removed. Before the oil and meal can be used as a food source, the
gossypol must be removed or deactivated. In addition, unfavorable
growing, harvesting, or storage conditions can cause cottonseed to mold
and become contaminated with a mold metabolite aflatoxin, which,
because it is carcinogenic, must be removed, or destroyed. The presence
of such toxic components prevents cottonseed from reaching its full
potential as a food source, especially in countries that grow cotton but
not soybeans. In the intact cottonseed, the gossypol is concentrated in
glands that are covered with a hydrophilic coating, which keeps the
gossypol from coming into contact with other components of the seed.
Originally, gossypol was deactivated by pressing, or expelling, the oil
out of moist seeds at relatively high temperatures, such as at
temperatures from about 110° to 130° C. Under these conditions, the
glands are ruptured by hot moisture, releasing gossypol. Most of the
gossypol reacts with protein, thereby forming bound gossypol, which is
insoluble. The rest reacts with phospholipids and other low molecular
weight components of the seed to give products that are soluble in oil
and other organic solvents, as is any unreacted gossypol. The gossypol
in these soluble products is referred to as free gossypol. Total gossypol is
the sum of bound gossypol and free gossypol. Total gossypol content of
meals made by such a process are typically from about 0.7 to 1.0 wt. %.
While binding to protein is advantageous in that it acts to detoxify the
gossypol, it is disadvantageous because it reduces the nutritive value of
the meal by reducing the available lysine content.

Currently, separation is done by expression, or by extraction of the oil

from flaked kernels at elevated temperatures with a solvent such as
hexane, or a combination of expression and extraction. The most
common method used today is solvent extraction, but unless a separate
moist heating preconditioning step is included, meals produced by this
method will contain unruptured glands and excessive amounts of free
gossypol. Furthermore, it is well known that adverse physiological
effects can occur with some meals containing high total gossypol, even
though free gossypol is within acceptable limits.

Hence, it has long been recognized that a process is needed that could
reduce the total gossypol of cottonseed meal by removing gossypol
instead of binding it to protein. Various processes have been developed
in an attempt to accomplish this. For example, multistep processes in
which both the oil and gossypol are extracted with different solvents, in
different steps, are known. For example, U.S. Pat. No. 4,359,417, teaches
a two step process comprising first extracting cottonseed flakes with an
85% aqueous ethanol solution at about 110° F., which removes some of
the gossypol with the remainder becoming bound to the meal. This is
followed by a second extraction but with a 95% ethanol solution at 175°
F., which removes the oil. Although such a process has merit, it can do
no better than produce a meal which still contains from 0.29 to 0.45 wt.
% total gossypol and 0.019 to 0.045 wt. % free gossypol.

Another reference, Canella and Sodini (Journal of Food Science,

42:1218-1219 (1977)), discloses a method wherein hexane extraction of
raw cottonseed at 25° C. is used to produce a cottonseed meal, followed
by room temperature extraction with n-butanol containing HCl at
carefully controlled pH of about 4.5, in order to obtain a product which
contains 0.34 wt. % total and 0.07 wt. % free gossypol. One
disadvantage of such a process is that the high boiling point of n-butanol
makes its removal from the meal difficult. Further, the one-solvent
processes that have been described in the art generally use mixed
solvent systems which are not suitable for food use. For example, U.S.
Pat. No. 3,557,168 teaches the use of a hexane-acetone mixture and U.S.
Pat. No. 2,950,198 (King et al, 8/1960) teaches the use of a hexane-
acetone-water mixture. Both of these processes leave residues which
produce a strong objectionable catty odor in the meal, thus making
them unsuitable for food use. Further, U.S. Pat. No. 4,747,979 teaches
the use of a chlorinated hydrocarbon as one component of their mixed
solvent, which of course is also unsuitable for food use.

Although other separation processes, such as the liquid cyclone process

taught in U.S. Pat. No. 3,615,657 can yield solid products containing less
than about 0.3 wt. % total gossypol from glanded seed, such low
gossypol fractions account for only about 50% of the total meal. The
remaining fraction contains relatively high total gossypol
concentrations.

Also, U.S. Pat. No. 4,219,469, teaches the use of a solvent solution
comprised of: a non-polar solvent, such as hexane; a polar solvent, such
as ethanol; and a food grade acid, such as citric acid; to obtain protein
isolates from cottonseed. The isolates are improved because of their
improved coloration. Gossypol is not significantly removed by the
process of this reference.
Furthermore, in conventional processes for producing cottonseed meal,
a small amount of the gossypol which is present in the seed, is bound to
phospholipids and extracted with the oil. This is in contrast to the major
portion which is bound to protein and remains in the meal. Another
patent, U.S. Pat. No. 3,062,876 discloses that the soluble bound gossypol
can be dissolved in methyethylketone (MEK) and hydrolyzed in the
presence of phosphoric acid. It is stressed that MEK be used because
the bound gossypol must be soluble in the acidic solution used for
hydrolysis.

The potential use of gossypol as a male contraceptive is an added

incentive for the need for a process that can separate unmodified
gossypol from both cottonseed oil and meal, instead of binding it to the
meal. Consequently, there still exists a need in the art for more effective
processes for removing gossypol, as well as other non food grade
components from cottonseed.

SUMMARY OF THE INVENTION

In accordance with the present invention, there is provided a process for

the extraction of gossypol from cottonseed, which process comprises:

(a) contacting cottonseed with a solvent solution comprised of: (i) a

water miscible organic solvent; (ii) water; and (iii) an acid which is
characterized as being strong enough to prevent binding of the gossypol
to the cottonseed protein, but not so strong that it will hydrolyze a
substantial portion of the cottonseed protein; under conditions
providing extraction of gossypol from said cottonseed by said solvent
solution, thereby producing cottonseed meal of reduced gossypol
content and solvent solution having gossypol therein; and

(b) separating said cottonseed meal of reduced gossypol content from

said solvent solution having gossypol therein.

In a preferred embodiment of the present invention, the water miscible

solvent is selected from the water miscible alcohols, esters, ethers,
nitriles and mixtures thereof, and is present in a weight ratio of solvent
solution to cottonseed of from about 12 to 1 to about 1 to 1, and the
cottonseed is in the form of kernels, flakes or a meal.
In other preferred embodiments of the present invention, the acid
present is such that it is able to provide the solvent solution with a pH of
from about 2 to about 5.

In yet other preferred embodiments of the present invention, the solvent

solution is comprised of about 2 to 12 wt. % water and from about 75 to
95 wt. % solvent and the extraction is conducted at a temperature from
about 50° C. up to, but not including, the boiling point of the solvent.

In still further preferred embodiments of the present invention, the

water miscible solvent is selected from the group consisting of the C 1 to
C 3 monohydric alcohols and the acid is selected from the tribasic acids:
citric acid, ascorbic acid, phosphoric acid, and mixtures thereof.

The present invention also includes cottonseed meals of reduced

gossypol content (and optionally reduced aflatoxin and/or fat content)
produced by the processes of the instant invention. Other aspects,
objects and advantages of the present invention will become readily
apparent from the ensuing description.

DESCRIPTION OF THE PREFERRED EMBODIMENTS

In general, the solvent solution of the present invention contains: a

water miscible organic solvent, the aforementioned acid, and water. The
water content of the combination of both the cottonseed and the solvent
solution should range from about 2 to 32 wt. %, preferably from about
2 to 14 wt. %, and more preferably from about 4 to 12 wt. %. The
amount of water required in the solvent solution will be affected by the
water already present in the cottonseed. After preparation for
extraction, the cottonseed kernels, flakes, or full fat meal, usually
contains from about 2 to 14 wt. % water. Preferably, the weight percent
of water in the solvent should be at least 12 wt. % minus the wt. % of
water in the cottonseed product. The upper limit of water concentration
is set by the minimum functional concentration of the other two
components, the solvent and the acid, which will be discussed in detail
below.

In order to inhibit binding of gossypol without significant hydrolysis of

protein, the pH of the solvent solution should be from about 2 to about
5, preferably from about 2 to about 4, and more preferably from about
2 to about 3. Depending on the equivalent weight and pK (negative
logarithm of the first dissociation constant of the acid) the effective
amount of acid will usually range from about 1 to 20 wt. % acid,
preferably from about 2 to 10 wt. % acid. Preferred acids are those
having equivalent weights of less than about 80 and a pK of from about
2 to about 4.2. Acetic acid, which has a pK of 4.75, is unsuitable for use
herein. Nonlimiting examples of preferred acids, are both organic and
inorganic (e.g. tribasic inorganic or organic acids) and include
phosphoric, citric, and ascorbic acids, and mixtures thereof. More
preferred are phosphoric (eq.wt.=33, pK=2.1) and citric (eq.wt. =64, pK
=3.1) acids, which at concentrations of 0.1 to 0.4 molar give pHs from
about 3.2 to 2.3. Most preferred are food grades of these acids, so that
residual acid in the cottonseed meal or flakes would not preclude
approval for food use.

Non-limiting examples of water miscible organic solvents usable in the

present invention include: alcohols, esters, ethers, nitriles, and mixtures
thereof. Preferred are the water miscible organic solvents. More
preferred are the C 1 to C 3 monohydric alcohols, most preferably are
those that are suitable for use in food processing, such as ethanol, which
is non-toxic, has favorable oil- and acid-solubility, is easy to recover for
recycling, and is a standard article of commerce. Maximum
concentration of organic solvent in the solvent solution is determined by
subtracting the required water and acid concentrations from 100 wt. %,
i.e. about 99 wt. % for extraction of cottonseed containing more than 12
wt. % water using the minimum amount of acid. The minimum
concentration will depend on the specific organic solvent and is
determined by the requirement that both oil and gossypol be soluble in
the solvent solution. The minimum will be highest for low extraction
temperatures and lowest for extractions carried out under pressure at
temperatures above the normal boiling point of the solvent. In general,
the solvent solution will contain about 70 to about 98 wt. % organic
solvent, preferably about 75 to about 95 wt. %, more preferably about
80 to about 90 wt. %. Most preferred is about 83 to about 92 wt. %
ethanol, which corresponds to use of commercial 95 vol. % ethanol to
prepare 0.1 to 0.4 molar solutions of citric and phosphoric acid.

The present invention can be practiced in a variety of ways. For

example, the extraction can be performed in a batch mode. As in any
extraction process, a single equilibration of the cottonseed flakes with
the solvent, followed by separation of the two phases, yields a miscella
containing extracted oil and gossypol, and a marc consisting of residual
flakes saturated with absorbed miscella. In order to remove all of the oil
and gossypol, the equilibrium process must be repeated several times
with fresh solvent. The number of cycles required will be dependent on
such things as the strength of the solvent, the solvent to flakes ratios, the
temperature and pressure conditions, and the desired degree of oil and
gossypol removal. In general, for maximum removal, from about 5 to 10
cycles may be required using the most preferred solvents at about 78°
C. and atmospheric pressure, with about a 3 to 1 wt. ratio of solvent to
flakes in the first cycle, and a 2 to 1 wt. ratio in subsequent cycles.

In general, the process of the present invention may be carried out over
a wide range of temperatures. This range will generally be from about
50° C. up to about 90° C. It is also understood that the extraction can
also be run at elevated temperatures and pressures, preferably up to
those pressures which can be safely practiced with the type of
equipment used in commercial cottonseed extraction. This pressure can
be up to about 60 psig at temperatures up to about 130° C, more
preferably from about 3 to about 10 psig, at temperatures of from about
70° C to about 90° C, preferably from about 80° C to about 90° C

The present invention can also be practiced in a continuous process

wherein the solvent solution is preferably run countercurrent to the
cottonseed and the residence time of the cottonseed, in contact with
fresh solvent, will determine the extent of oil and gossypol removal.
Such determinations of residence times etc. are within the ordinary skill
of those in the art, given the teachings herein, and need not be discussed
further. It is preferred to rinse the cottonseed meal of reduced gossypol
content (after the step of contacting) With fresh solvent, which may be
similar to that used in the extraction but without added acid in order to
recover acid absorbed by the cottonseed. Thus, the fresh solvent may
include a water miscible organic solvent selected from the group
consisting of alcohols, esters, ethers, nitriles and mixtures thereof.

The term cottonseed, as used herein, is meant to include cottonseed in

any form. That is, the present invention can be practiced on cottonseed
in any form (e.g. kernels, flakes, meal, full fat, wholly defatted prior to
the step of contacting, partially defatted prior to the step of contacting,
etc.), although it is preferred not to us whole seed because of the
difficulty of achieving an effective extraction. Also, ground kernels
present a problem of fines which makes separation of the meal from
miscella difficult.

The foregoing detailed description is given merely for purposes of

illustration. Modifications and variations may be made therein without
departing from the spirit and scope of the invention.

The following examples are presented for illustrative purposes only and
are

not to be taken as limiting the scope of the claims hereof.

EXAMPLE 1

Full-fat cottonseed meals, containing 8% moisture, were flaked using

conventional flaking rolls set at 0.008 inches. A 300 gram (g) portion of
the flakes and a 95 vol. % ethanol solution (800g) were placed in a
jacketed, stainless steel, cylindrical extractor (6" diam.×6" deep) fitted
with a 12 mesh stainless steel retaining screen at the bottom. Hot (79° C)
water was circulated through the jacket. Solvent was recirculated
through the flakes at a rate of 1 liter (L)/min for 10 min. Miscella (ca
300 g) was drained from the extractor and the flakes were reextracted
under the same conditions using 600 g portions of solvent solution. After
the seventh extraction, each extraction being about 10 min in duration,
the spent flakes were washed with 650 g of 95 vol. % ethanol to remove
acid absorbed by the meal. Spent flakes were allowed to air dry at room
temperature (ca 25° C) over night and then oven dried at 1010 C for one
hour. They were then ground with a Wiley mill to pass a 20 mesh
screen, analyzed for residual lipids, total gossypol, and free gossypol.
The solvent solutions were comprised of 0.1 and 0.4M citric acid,
prepared using anhydrous citric acid, and 0.1 and 0.34M phosphoric
acid, prepared using 85 wt. % orthophosphoric acid, all in 95 vol. %
ethanol. For comparison, an extraction of the same lot of flakes was
made using 95 vol. % ethanol without tribasic acid. The results are
shown in Table I below for full fat flakes which initially contained 26.3
wt. % lipids, 8 wt. % moisture, 1.08 wt. % total gossypol and 1.06 wt. %
free gossypol.

TABLE I
______________________________________
 wt. % wt. % wt. % RESIDUAL TOTAL FREE SOLVENT LIPIDS
GOSSYPOL* GOSSYPOL*
______________________________________

No acid 0.75 1.08 0.08

0.1M citric
1.1 0.40 0.02
0.4M citric
1.1 0.09 0.007
0.1M 0.5 0.27 0.02
phosphoric
0.34M 1.4 0.03 0.005
phosphoric
______________________________________

*Moisture- and oilfree basis. Conventional hexane extraction left 1.46

wt. % total gossypol, of which 0.56 wt. % was free gossypol, in the meal.

This example shows that the present invention provides a u very

substantial reduction in the concentration of total gossypol and free
gossypol, as compared to extraction with ethanol alone or extraction
with hexane.

EXAMPLE 2

As shown in the following Table II below, when cottonseed containing

aflatoxin, chiefly aflatoxin B1, is processed as described in Example 1
hereinabove, aflatoxin, as well as gossypol, are removed from the meal.

TABLE II
________________________________________________________
__________________
wt. % ppb wt. % wt. % RESIDUAL B1 TOTAL FREE SOLVENT
LIPIDS AFLATOXIN* GOSSYPOL* GOSSYPOL*
________________________________________________________
__________________

None** 26.2 69 1.00 0.91

No Acid 0.94 3.6 0.80 0.01
0.1M citric
0.87 3.8 0.22 0.01
0.4M citric
2.3 3.4 0.09 0.06
0.1M phosphoric
1.1 3.7 0.08 0.01
0.34M phosphoric
5.1 2.9 0.05 0.004
________________________________________________________
__________________

*Moisture- and oilfree basis. **Unprocessed fullfat flakes; as is basis.

Conventional hexane extraction left 37.5 ppb aflatoxin, 1.24% total-,

and 0.84% free- gossypol, all moisture- and oil-free basis by weight, in
the meal.

EXAMPLE 3

The process of the instant invention is intended primarily for use on

full-fat flakes that contain very little bound gossypol (total minus free);
however, as illustrated in this example a significant reduction in total
gossypol content of partially defatted or fully defatted meals and other
products containing large amounts of bound gossypol can be achieved
by extraction with solvents described herein.

A 300 g sample of cottonseed flakes, similar to those used in Example 1,

were extracted with 95 vol. % ethanol in a Soxhlet apparatus for 4
hours, which removed most of the oil and converted most of the
gossypol from free to bound form. The resulting defatted meal, which
contained 6.5 wt. % residual lipids, 1.40 wt. % total gossypol and 0.02
wt. % free gossypol, was extracted three times using 800, 600, and 600 g
of acidified 95 vol. % ethanol as indicated in Table III below. Each
extraction was at 78° C. for 20 min.

TABLE III
______________________________________
wt. % RE- wt. % wt. % SIDUAL TOTAL FREE LIPIDS*
GOSSYPOL* GOSSYPOL*
______________________________________
Starting Material
6.5 1.40 0.02
(i.e. defatted
meal)
0.4M citric acid
0.29 0.88 0.12
in 95 vol. %
ethanol
0.34M phosphoric
0.13 0.52 0.09
acid in 95 vol. %
ethanol
______________________________________

*Moisture- and oilfree basis.

Journal Article
Isopropanol as a solvent for extraction of Add to
cottonseed oil marked
I. Preliminary investigations items
Journal Journal of the Add to
American Oil shopping
Chemists' Society cart
Publisher Springer Berlin / Add to
Heidelberg saved items
Permissions
ISSN 0003-021X (Print) & Reprints
1558-9331 (Online) Recommend
Issue Volume 24, Number this article
11 / November, 1947
DOI 10.1007/BF02643518
Pages 370-375
Subject Collection Chemistry and
 Materials Science
SpringerLink Date Monday, June 11,
2007

W. D. Harris1, F. F. Bishop1, C. M. Lyman2 and R. Helpert1

(1) Chemical Engineering Department, A. & M. College of Texas,

Texas, USA
(2) Texas Agricultural Experiment Station, A. & M. College of Texas,
Texas, USA
Summary Phase equilibrium data for the system; cottonseed oil-
isopropanol-water were determined at 30°C. and compared with data for
the system; cottonseed oilethanol-water. The relative phase distribution
of fatty acids and cottonseed oil in mixtures with isopropanol and water
was studied under varying conditions of water and fatty acid
concentrations. These tests showed the fatty acids to be highly
concentrated in the alcohol-water phase.
Flaked cottonseed meats were extracted in continuous extraction
apparatus with 91% isopropanol, 99% isopropanol, and mixtures of
commercial hexane and isopropanol. Analytical data on the extractions
show that 91% isopropanol is an efficient solvent for extracting active
gossypol along with the oil.
Rat and swine feeding tests of the isopropanol extracted meal showed it
to be highly superior to hydraulic meal as a source of protein.
A method was developed for treatment of the cottonseed-isopropanol
miscella by liquid-liquid extraction to separate purified oil and fatty acid
fractions from other materials in the extract.

References secured to subscribers.

Journal of Food Science

Volume 49 Issue 4 Page 1057-1060, July 1984

To cite this article: E. H. RAHMA, M. S. NARASINGA RAO (1984)

Gossypol Removal and Functional Properties of Protein Produced by
Extraction of Glanded Cottonseed with Different Solvents
Journal of Food Science 49 (4), 1057–1060.
doi:10.1111/j.1365-2621.1984.tb10391.x

Prev Article Next Article

Abstract

Gossypol Removal and Functional Properties of Protein Produced by

Extraction of Glanded Cottonseed with Different Solvents

• E. H. RAHMA11Author Narasinga Rao (to whom

inquiries should be directed) is Project
Coordinator, Protein Technology Discipline,
Central Food Technological Research Institute,
Mysore — 570 013, India. Author Rahma is a
United Nations University Fellow; present
address: Food Science & Technology Dept.,
Faculty of Agriculture, Univ. of Monoufeia,
Shibin-EI-Kom, Egypt. and
• M. S. NARASINGA RAO11Author Narasinga Rao (to
whom inquiries should be directed) is Project
Coordinator, Protein Technology Discipline,
Central Food Technological Research Institute,
Mysore — 570 013, India. Author Rahma is a
United Nations University Fellow; present
address: Food Science & Technology Dept.,
Faculty of Agriculture, Univ. of Monoufeia,
Shibin-EI-Kom, Egypt.
•
•
•
1
• Author Narasinga Rao (to whom inquiries should be directed) is
Project Coordinator, Protein Technology Discipline, Central Food
Technological Research Institute, Mysore — 570 013, India.
Author Rahma is a United Nations University Fellow; present
address: Food Science & Technology Dept., Faculty of Agriculture,
Univ. of Monoufeia, Shibin-EI-Kom, Egypt.

ABSTRACT
Cottonseed flakes were extracted with one of the following solvents: (A)
hexane; (B) 1:1 mixture of 85% isopropanol and hexane; and (C)
acetone followed by 1:1 mixture of isopropanol and hexane. Meal B had
the lowest free gossypol content of 0.069%. The functional properties
and the protein content of all the meals were similar.
Ultracentrifugation did not reveal any change in the proportion of the
protein fractions. Gel electrophoresis indicated minor differences.

This article is cited by:

• I. Vroh Bi, J. P. Baudoin and G. Mergeai. (1998) Cytogenetics of

the 'glandless-seed and glanded-plant' trait from Gossypium
sturtianum Willis introgressed into upland cotton (Gossypium
hirsutum L.). Plant Breeding 117:3, 235–241

Abstract Abstract and References Full Article PDF

Journal of Food Science

Volume 48 Issue 3 Page 988-989, May 1983

To cite this article: HAYTHAM JADDOU, M. AL-HAKIM, L.Z. AL-

ADAMY, M.T. MHAISEN (1983)
Effect of Gamma-Radiation on Gossypol in Cottonseed Meal
Journal of Food Science 48 (3), 988–989.
doi:10.1111/j.1365-2621.1983.tb14948.x

Prev Article Next Article

Welcome to Blackwell Synergy - the source of highly cited peer-

reviewed society journals from Blackwell Publishing
You are attempting to access the PDF of this article. To access this
content you, or your library, will need to have an online subscription to
the journal. Alternatively you can purchase immediate access to the
article using a credit card.

• If you already have an online subscription please login at the top

of this page.
• To purchase an online subscription to this journal please visit the
journal homepage and click on 'Subscribe'.
• To purchase immediate access to this article for 30 days through
our secure web site using a credit card, please click the 'Full Text
Article' or 'PDF' button below, and follow the instructions.

Abstract

Effect of Gamma-Radiation on Gossypol in Cottonseed Meal

• HAYTHAM JADDOU11The authors are affiliated with

the Nuclear Research Center, Agriculture &
Biology Dept., P.O. Box 765, Baghdad, Iraq.,
• M. AL-HAKIM11The authors are affiliated with the
Nuclear Research Center, Agriculture & Biology
Dept., P.O. Box 765, Baghdad, Iraq.,
• L.Z. AL-ADAMY11The authors are affiliated with the
Nuclear Research Center, Agriculture & Biology
Dept., P.O. Box 765, Baghdad, Iraq., and
• M.T. MHAISEN11The authors are affiliated with the
Nuclear Research Center, Agriculture & Biology
Dept., P.O. Box 765, Baghdad, Iraq.
1
• The authors are affiliated with the Nuclear Research Center,
Agriculture & Biology Dept., P.O. Box 765, Baghdad, Iraq.

The authors are indebted to Dr. A. Pans, of the USDA-ARS Southern

Regional Research Center, for the donation of a standard sample of
pure gossypol.

ABSTRACT

The effect of gamma–radiation, in the range 5–30 KGy on free,

total and pure gossypol was investigated in an attempt to reduce or
eliminate gossypol from cottonseed meal using different solvent systems.
Maximum reduction in gossypol concentration was attained at a dose of
25 KGy of gamma-radiation with chloroform as a solvent, a
spectrometric method was used for analysis. The reductions attained for
pure, free and total gossypol were found to be 96%, 60% and 80%,
respectively.

Journal of Food Science

Volume 46 Issue 6 Page 1726-1733, November 1981

To cite this article: JOHN P. CHERRY, MARIE S. GRAY (1981)

Methylene Chloride Extraction of Gossypol from Cottonseed Products
Journal of Food Science 46 (6), 1726–1733.
doi:10.1111/j.1365-2621.1981.tb04473.x

Prev Article Next Article

Welcome to Blackwell Synergy - the source of highly cited peer-

reviewed society journals from Blackwell Publishing

You are attempting to access the PDF of this article. To access this
content you, or your library, will need to have an online subscription to
the journal. Alternatively you can purchase immediate access to the
article using a credit card.

• If you already have an online subscription please login at the top

of this page.
• To purchase an online subscription to this journal please visit the
journal homepage and click on 'Subscribe'.
 • To purchase immediate access to this article for 30 days through
our secure web site using a credit card, please click the 'Full Text
Article' or 'PDF' button below, and follow the instructions.

Abstract

Methylene Chloride Extraction of Gossypol from Cottonseed Products

• JOHN P. CHERRY11Authors Cherry and Gray

(retired) are affiliated with the Southern
Regional Research Center, USDA-SEA-AR, P.O.
Box 19687, New Orleans, LA 70179. and
• MARIE S. GRAY11Authors Cherry and Gray (retired)
are affiliated with the Southern Regional
Research Center, USDA-SEA-AR, P.O. Box 19687,
New Orleans, LA 70179.
1
• Authors Cherry and Gray (retired) are affiliated with the Southern
Regional Research Center, USDA-SEA-AR, P.O. Box 19687, New
Orleans, LA 70179.

Presented at the 39th Annual Meeting of the Institute of Food

Technologists, St. Louis, MO, June 10–13, 1979.

The authors express their appreciation to C. James for the quantitative

gel electrophoretic analyses of proteins, and to J.H. Carra and J.J.
Herbert for the photomicrograph of the gossypol glands.

Names of companies or commercial products are given solely for the

purpose of providing specific information; their mention does not imply
recommendation or endorsement by the U.S. Department of Agriculture
over others not mentioned.

ABSTRACT

Methylene chloride was used to reduce the amount of free and total
(free plus bound) gossypol in hexane-defatted meal and the
liquidcyclone-processed (LCP) underflow fraction of glanded
cottonseeds from 2.6% and 3.4% to 0.013% and 0.15%, respectively
(the accepted level of free gossypol in cottonseed products for food is
0.045%). The cottonseed meals were pretreated one of three ways to
rupture the gossypol glands: (a) equilibrated with additional water; (b)
suspended in various water-propylene glycol mixtures; or (c) mixed
with an acetic acid-water-propylene glycol solution. The gossypol was
then readily extracted from the meals with methylene chloride. Low
levels of water and acetic acid in propylene glycol aided methylene
chloride in the removal of free and total gossypol and did not greatly
alter the proximate composition, solubility, and gel electrophoretic
properties of proteins; amino acid content; and chemical scores of the
treated meals. Success with this process should improve the potential of
LCP-cottonseed by-product (underflow) as feed or food.

This article is cited by:

• E. H. RAHMA and M. S. NARASINGA RAO. (1984) Gossypol

Removal and Functional Properties of Protein Produced by
Extraction of Glanded Cottonseed with Different Solvents.
Journal of Food Science 49:4, 1057–1060

Abstract Abstract and References Full Article PDF

Journal of Food Science

Volume 42 Issue 5 Page 1218-1219, September 1977

To cite this article: M. CANELLA, G. SODINI (1977)

EXTRACTION OF GOSSYPOL AND OLIGOSACCHARIDES FROM
OILSEED MEALS
Journal of Food Science 42 (5), 1218–1219.
doi:10.1111/j.1365-2621.1977.tb14463.x

Prev Article Next Article

Welcome to Blackwell Synergy - the source of highly cited peer-

reviewed society journals from Blackwell Publishing

You are attempting to access the PDF of this article. To access this
content you, or your library, will need to have an online subscription to
the journal. Alternatively you can purchase immediate access to the
article using a credit card.

• If you already have an online subscription please login at the top

of this page.
• To purchase an online subscription to this journal please visit the
journal homepage and click on 'Subscribe'.
• To purchase immediate access to this article for 30 days through
our secure web site using a credit card, please click the 'Full Text
Article' or 'PDF' button below, and follow the instructions.

Abstract

EXTRACTION OF GOSSYPOL AND OLIGOSACCHARIDES FROM

OILSEED MEALS

• M. CANELLA11Laboratori Ricarche di Base,

Snamprogetti S.p.A. Monterotondo, Rome, Italy
and
• G. SODINI11Laboratori Ricarche di Base,
Snamprogetti S.p.A. Monterotondo, Rome, Italy
1
• Laboratori Ricarche di Base, Snamprogetti S.p.A. Monterotondo,
Rome, Italy

ABSTRACT

Removal of gossypol from cottonseed meal and fermentable sugars from

soybean meal by butanol-HCl solution was tested. Acidic butanol
treatment yields low gossypol cottonseed protein concentrates and low
oligosaccharides soy protein concentrates, respectively. This procedure
does not appreciably alter proteins, as it is shown by the comparison of
electrophoretic patterns of albumins and globulins extracted from meal
and corresponding protein concentrates.

This article is cited by:

 • E. H. RAHMA and M. S. NARASINGA RAO. (1984) Gossypol
Removal and Functional Properties of Protein Produced by
Extraction of Glanded Cottonseed with Different Solvents.
Journal of Food Science 49:4, 1057–1060

Abstract Abstract and References Full Article PDF

Journal of Food Lipids

Volume 9 Issue 2 Page 161-173, June 2002

To cite this article: F. ZHANG, K. C. RHEE, S. S. KOSEOGLU (2002)

ISOPROPYL ALCOHOL EXTRACTION OF COTTONSEED
COLLETS: CRUDE OIL COMPOSITION
Journal of Food Lipids 9 (2), 161–173.
doi:10.1111/j.1745-4522.2002.tb00216.x

Prev Article
Abstract
ISOPROPYL ALCOHOL EXTRACTION OF COTTONSEED
COLLETS: CRUDE OIL COMPOSITION

• F. ZHANG11Food Protein Research & Development

Center Texas A&M University College Station,
Texas 77843–2746,
• K. C. RHEE Food Protein Research & Development
11

Center Texas A&M University College Station,

Texas 77843–2746,
• S. S. KOSEOGLU Food Protein Research &
11

Development Center Texas A&M University

College Station, Texas 77843–
274611Corresponding author: TEL: (979) 845–
2749; FAX: (979) 845–2744; E-mail: s-
koseoglu@tamu.edu
1
• Food Protein Research & Development Center Texas A&M
University College Station, Texas 77843–2746
1
Corresponding author: TEL: (979) 845–2749; FAX: (979) 845–2744; E-
mail: s-koseoglu@tamu.edu

ABSTRACT

Isopropyl alcohol (IPA) is an attractive alternative solvent to hexane for

use in vegetable oil extraction. The relative efficiencies of IPA and
hexane extractions using both cottonseed collets and flakes were
evaluated in terms of product composition. The aqueous IPA extracted
crude cottonseed oils from expander pretreated collets were analyzed
for their nonacylglycerol compositions. The IPA extraction (88, 93, 95
and 97% IPA) resulted in more free fatty acids in the crude oils than
did hexane extraction, and the level of the free fatty acids increased as
the IPA concentration increased. The phosphorus content was higher in
the IPA-extracted oils compared to those of their hexane-extracted
counterparts. The HPLC analysis showed that the IPA extractions
increased concentrations of phosphatidylcholine (PC),
phosphatidylethanolamine (PE), and phosphatidylinositol (PI) in the
crude cottonseed oils. More sugar and less gossypol were found in IPA-
extracted oils and the level of sugar decreased as the IPA concentration
increased. The oil extracted with 95% IPA from the expander-produced
collets were lower in free fatty acid, sugar, and gossypol than those
obtained from the flakes. The amount of phosphorus in the oil extracted
from the collets was approximately 45% higher than that from the
flakes. The IPA extraction, in combination with expander pretreatment,
produced cottonseed meals with free gossypol of 366 ppm, making them
suitable for feeding nonruminant animals.

Users who read this article also read:

PROPERTIES OF CARICA PAPAYA L. (PAPAYA) SEED OIL

FOLLOWING EXTRACTIONS USING SOLVENT AND
AQUEOUS ENZYMATIC METHODS
T. PUANGSRI, S.M. ABDULKARIM and H.M. GHAZALI
Preparation of low-gossypol cottonseed flour
Sayed M. Damaty, Bertram J. F. Hudson
Department of Food Science, University of Reading, Reading, England
ABSTRACT
A new laboratory process has been developed for the production of fat-
free cottonseed flour with a very low content of both free and bound
gossypol. The process depends on the successive extraction of flaked
cottonseed meats with (1) hexane and (2) aqueous acetone, followed by
anhydrous acetone. The cottonseed flour so derived, with a total
gossypol content of about 0.1%and a protein content around 63%is
considered appropriate for use in human food.
Received: 8 April 1974; Accepted: 6 August 1974
DIGITAL OBJECT IDENTIFIER (DOI)

10.1002/jsfa.2740260114 About DOI

Modified Cottonseed May Be Used for Food
By RANDOLPH E. SCHMID
The Associated Press
Monday, November 20, 2006; 8:38 PM
WASHINGTON -- Cotton, for thousands
of years one of the most important crops
for clothing and shelter, might also
become a source of food. A chemical
called gossypol makes cottonseed inedible
for humans, though some of it is used in
feed for cattle, which are less affected by
the toxin. Now, researchers at Texas
A&M University have genetically
modified cotton to produce seeds with
little or no gossypol.
It's a step they say could help provide
valuable protein to millions of people.
Their findings are reported in Tuesday's
issue of Proceedings of the National
Academy of Sciences.
Keerti Rathore of the university's
Institute for Plant Genomics and
Biotechnology, said the modified plants
continue to have gossypol in their stems
and leaves where it helps resist insects,
but the chemical is significantly reduced
in the seed.
Worldwide, 44 million tons of cottonseed
is produced annually. It is grown in 80
countries and the seeds are 23 percent
protein, Rathore said.
They are pressed for oil, and in the
United States about half of the remaining
meal goes into animal feed, he explained.
But, with the gossypol removed, the meal
can be ground into flour and used in
cooking, he said.
These undated black-and-
white photos provided by
the Proceedings of the
National Academy of
Sciences (PNAS) show
normal, top and engineered
toxin-free, bottom,
cottonseeds. Cotton, for
thousands of years one of
the most important crops
for clothing and shelter,
might also become a source
of food. A chemical called
gossypol makes cottonseed
inedible for humans,
though some of it is used in
feed for cattle, which are
less affected by the toxin.
(AP Photo/PNAS) (AP)
David Woods, a delegate
from West Virginia's
Berkeley County, shares
his views on Mitt Romney
during the state's
Republican convention.
Romney finished second to
Mike Huckabee, with John
McCain registering just 1
percent. ( Kiichiro Sato
-- AP )
Rathore said he hasn't tasted the cottonseed meal, but added that
researchers who had bred a different gossypol-free cottonseed had, and
reported that tasted good.

Unfortunately, he said, that earlier version removed gossypol from all

parts of the plant, which was then attacked by a variety of insects.

Jodi Scheffler, a research geneticist at the Agriculture Department's

Agricultural Research Service center in Stoneville, Miss., said the
development has potential.

"It definitely gives us new hope," said Scheffler, who was not part of
Rathore's research team.

"This is an age-old problem," she explained, the protein contained in

cottonseed is good, but cannot be used by people or most animals
because it contains this toxin.

The potential problems that have to be worked out, she said, are
determining whether the genetic change is stable through generations,
and overcoming regulatory and public acceptance problems that can
face any genetically modified foods.

One of the reasons it is important is for regions such as West Africa,

where many small farmers grow cotton as a cash crop and would like to
be able to use the seed to feed themselves and their livestock, she added.

Rathore's research was funded by the Texas Cotton Biotechnology

Initiative, Cotton Inc., and the Texas Agricultural Experiment Station.

___

On the Net:

Proceedings of the National Academy of Sciences:

http://www.pnas.org

Institute for Plant Genomics and Biotechnology:

http://ipgb.tamu.edu

New solvent for cottonseed oil processing.

From: Agricultural Research | Date: 8/1/1996 | Author: Lee, Jill

• Print
• Digg
• del.icio.us

Petroleum-based solvents that are meant to extract more oil from

cottonseeds were initially used during World War I to account for the
shortage in oil for food, soaps and explosives. However, a more efficient
way of getting oil from seeds was discovered by switching from the oil
removing solvent hexane to isohexane. The use of isohexane as an
alternative solvent proves to be cleaner, safer and more cost-effective
than using hexane. Cottonseed, a billion-dollar industry in the US alone,
is mainly used for frying snack foods.

Consider cottonseed oil. It fries the humble potato chip, an American

picnic classic. Summer sunbathers glisten with tanning oil made from it.

Cottonseeed was the first major vegetable oil used in the United States.
In the 19th century, hydraulic presses were used to remove the oil.
Later, continuous screw-type presses offered more efficiency. The
shortage of oil for soaps, food, and explosives during World War I
prompted the use of petroleum-based solvents to get more oil from the
seeds.

Now a scientist with the Agricultural Research Service may have found
a more efficient way to meet industry's needs. The key: switching from
hexane, the current oil removing solvent, to isohexane, which has
several benefits.

"We found that substituting isohexane for hexane in production

required little or no change in the cottonseed crushing operation," says
chemical engineer Peter J. Wan. "We tested isohexane in plants
operating at full capacity and saw both savings in energy and more
product produced per hour."

Scientists at ARS began to study alternative solvents during the energy

crisis of the 1970's.

At first, their goal was to find more effective solvents, such as acetone,
to remove oil and undesirable pigments. Later, renewable solvents that
didn't rely on petroleum sources became the focus. But the ideal
candidate - ethanol - proved too costly.

During the 1980's and 1990's the focus switched to achieving cleaner,
safer, and cost-effective production, so the search for alternative
solvents continued.

A research team led by Wan decided to give isohexane a try. The

National Cottonseed Products Association also supported him, and
some of its members offered their mills to test the new solvent.

"Our experience with isohexane was positive. We saw good extraction

and some energy savings," says Billy Clark, president of Yazoo Valley
Mill in Greenwood, Mississippi.

"We even reran the test to confirm results. We had no trouble getting
isohexane from the supplier for that second test."

"Cottonseed processors have always been industry leaders," says David

Kinard, director of research and education for the century-old National
Cottonseed Products Association. "Alternative production methods that
increase efficiency are appreciated by everyone."
The cottonseed industry represents a billion-dollar U.S. market, says
Wan. Each year, 1.4 billion pounds of cottonseed oil are consumed, and
their main use is in snack-making.

"Cottonseed oil is considered the 'gold standard' for frying potato

chips," says Scott Sanford, who is with the USDA's Economic Research
Service. "It's also replacing animal fat in some fast-food restaurants."

"Provided isohexane is economically priced, any oilseed processor could

benefit from using it," says Wan. "For example, they'd save energy,
because it takes less steam to recover isohexane from the meal and oil
during processing."

Peter Wan is in the USDA-ARS Commodity Utilization Research Unit,

Southern Regional Research Center, 1100 Robert E. Lee Blvd., New
Orleans, LA 70124; phone (504) 286-4450, fax (504) 286-4419, e-mail
pwan@nola.srrc.usda.gov

COPYRIGHT 1996 U.S. Government Printing Office

This material is published under license from the publisher through the
Gale Group, Farmington Hills, Michigan. All inquiries regarding rights
should be directed to the Gale Group.
For permission to reuse this article, contact Copyright Clearance
Center.

• Print
• Digg
• del.icio.us
Gossypol

The use of glanded cottonseed meal is limited in fish diets due to its
gossypol content. Gossypol is found in the pigment glands of cotton and
may account for as much as 2.4 percent of seed weight in certain
varieties (Berardi and Goldblatt, 1980). Free gossypol is tolerated at
varying amounts by different fish species, but excessive concentrations
can depress growth and cause damage to various organ tissues.
Gossypol has also been identified as a carcinogen with aflatoxin B in
rainbow trout (Sinnhuber et al., 1968a).

Roehm et al. (1967) reported adverse effects of free gossypol on the

growth of rainbow trout fed concentrations of 1,000 mg/kg of diet or
higher, but not at 250 mg/kg of diet. Herman (1970) found that although
growth depression did not occur at concentrations lower than 290
mg/kg of diet, histopathological changes were noted at 95 mg/kg of diet
and included thickening of the glomerular basement membrane of the
kidney and necrosis and ceroid deposition in the liver. Wood and
Yasutake (1956) noted similar histopathology in rainbow trout. These
results indicate that the maximum concentration of free gossypol in the
diets of salmonids should be restricted to 100 mg/kg of diet or less.

Growth inhibition was observed in fingerling channel catfish fed more

than 900 mg of free gossypol/kg of diet (Dorsa et al., 1982), but a portion
of the depression was possibly due to a dietary lysine deficiency
resulting from the irreversible binding of lysine and gossypol (Wilson et
al., 1981; Dorsa et al., 1982). In commercial catfish diets in the United
States, 10 to 20 percent cottonseed meal is commonly used. Robinson
(1991) reported that the solvent extracted cottonseed meal used in
catfish diets, which typically contains 400 to 800 mg of free gossypol/kg,
would not provide toxic concentrations of free gossypol when mixed into
catfish diets; however, the concentration of available lysine in the diet
should be scrutinized when cottonseed meal replaces soybean meal. Blue
tilapia have been shown to tolerate free gossypol concentrations as high
as 1,800 mg/kg of diet with no apparent growth depression (Robinson et
al., 1984).

Title: Release of gossypol from cottonseed meal in fermentation

medium.

POPLINE Document Number: 003195

Author(s):

Khandeparkar VG

Source citation:

Indian Journal of Experimental Biology, 1981 Jun;19(6):574-6.

Abstract:

Cottonseed meal is a source of rich protein used traditionally in

ruminant feeds and even for human nutrition in certain areas of the
world. Is is known, however, that gossypol, a toxic substance, is released
from cottonseed meal during processing. Toxicity is attributed to free
gossypol. Laboratory experimentation was conducted to determined
how gossypol is released during fermentation. Cottonseed meal was
added to a growth medium of Bacillus subtilis-159 and assayed after 48
hours for the presence of amylase. Cottonseed meal from India and the
U.S. were used in the research. Gossypol was released in free form
through hydrolyzing of the meal protein by the protease of B. Subtilis.
The concentration of gossypol in the assay increased progressively over
the incubation time. This released gossypol was inhibitory to the
organisms.

Keywords:

Clinical Research
Plants, Medicinal
Laboratory Procedures
Ingredients and Chemicals
Research Methodology
Medicine
Health Services
Delivery of Health Care
Health
Laboratory Examinations and Diagnoses
Examinations and Diagnoses
Index page
Antioxidative effects of cottonseed meals as evaluated in cooked meat

K. S. Rhee , , a, Y. A. Ziprina and M. C. Calhounb

a
Meat Science Section, Department of Animal Science, Texas A&M
University, College Station, TX 77843-2471, USA
b
Agricultural Research and Extension Center, Texas Agricultural
Experiment Station, San Angelo, TX 76901, USA
Received 6 June 2000; revised 13 October 2000; accepted 13 October
2000 Available online 22 March 2001.

Abstract

Cottonseed meal samples were collected from nine cottonseed oil mills
in the USA. The meal samples contained 230–1,820 ppm free gossypol
and 8,300–16,480 ppm total gossypol. Finely ground meals were
incorporated into ground beef with 15% fat or ground lean meats (beef
semimembranosus muscle and goat lean composite), at 0–3% of the final
meat mixture weight. The meat mixtures were cooked to an internal
temperature of 77°C, aerobically refrigerated for 3 days, and analyzed
for lipid oxidation using a distillation 2-thiobarbituric acid-reactive
substances (TBARS) assay method. All the cottonseed meals were highly
effective antioxidants in cooked meats, decreasing day-3 TBARS values
by 77–91% with 3% addition. Estimated gossypol levels in the meat
samples with 3% cottonseed meal were 7–55 ppm free gossypol (vs. the
450 ppm maximum limit set by the United States Food and Drug
Administration for human food products) and 249–494 ppm total
gossypol (vs. the 12,000 ppm maximum limit by the UN Food and
Agriculture and World Health Organizations for food products). There
was no significant correlation between the antioxidative efficacy of the
meals and free or total gossypol levels.

Author Keywords: Antioxidant; Cottonseed meal; Cooked meat

Supercritical carbon dioxide extraction of cottonseed oil

Paramita Bhattacharjeea, , , Rekha S. Singhala and Sudha R. Tiwarib

a
Food and Fermentation Technology Department, Institute of Chemical
Technology, University of Mumbai, Matunga 400 019, Mumbai, India
b
Central Institute for Research in Cotton, Adenwala Road, Matunga,
Mumbai 400 019, India
Received 11 October 2005; accepted 6 March 2006. Available online 28
March 2006.

Abstract

Supercritical fluid extraction (SFE) using carbon dioxide is a popular

technique for oil extraction due to its high extraction efficiency, short
extracting time, lower refining requirement and absence of chemical
residues or contamination in the extracted oils. In this work, an attempt
has been made to extract oil from a local variety of cottonseed using this
technique. The effects of the extraction parameters of pressure,
temperature and time of extraction of oil were optimized by using
statistical techniques such as central composite rotate design (CCRD)
and response surface methodology (RSM), with a view to maximize the
oil yield with minimum gossypol extraction. From this study, it could be
concluded that the yield of cottonseed oil can be improved at pressure
higher than 550 bar, in the temperature zone of 70–80 °C and extracting
time of 2–3 h.
 Quick method for estimating free gossypol in cottonseed, meats, collets, an
extracted meals
Journal Journal of the American Oil Chemists' Society
Publisher Springer Berlin / Heidelberg
ISSN 0003-021X (Print) 1558-9331 (Online)
Issue Volume 73, Number 2 / February, 1996
DOI 10.1007/BF02523895
Pages 199-202
Subject Collection Chemistry and Materials Science
SpringerLink Date Thursday, November 09, 2006
&lta target="_blank" href="http://adfarm.mediaplex.com/ad/ck/49692?
mpt=200802061125167848154"> &ltimg
src="http://adfarm.mediaplex.com/ad/bn/49692?mpt=200802061125167848
alt="Advertisment"> </a>

R. J. Hron Sr.1 , M. S. Kuk1 and P. J. Wan1

(1) SRRC, ARS, USDA, 70179 New Orleans, Louisiana

(2) Southern Regional Research Center, P. O. Box 19687, 70179 New Orlea
LA
 Received: 11 August 1995 Accepted: 4 September 1995
Abstract A method for estimating free gossypol (FG) has been developed th
decreases sample-determination time from over 2 h to about 25 min per sam
With auto pipetters and bottle-to dispensers, six sample determinations can
completed in approximately 50 min. The method consisted of adding water
acetone separately to a fixed sample weight, mixing, filtering, diluting with
acetone, and reading absorbance on a spectrophotometer. Absorbance was
against the official American Oil Chemists’ Society’s FG method fo
samples that contained FG between 0.02 and 0.9%. Quadratic least squares
regression for 31 samples had a correlation coefficient ofr 2=0.986 and a stan
error of estimated FG of 0.032%.

Key Words Analysis - cottonseed - environment - gossypol - plant

breeder - polyphenol - spectrophotometer

Presented in part at the AOCS Annual Meeting, Anaheim, California, Apri

References secured to subscribers.

Technology Reduces Gossypol In Cotton Seed

ScienceDaily (Jan. 27, 2007) — Genetic technology developed by

Agricultural Research Service (ARS) scientists and cooperators suggests
that cottonseed could one day become a significant source of low-cost
protein for the developing world.

See also:
Plants & Animals

• Seeds
• Agriculture and Food
• Biotechnology
• Botany
• Genetics
• Life Sciences

Reference

• Cotton
• Transgenic plants
• Plant breeding
 • Seed predation

The research team, headed by Keerti Rathore at the Institute for Plant
Genomics and Biotechnology, Texas A&M University, and ARS
chemists Robert D. Stipanovic and Lorraine S. Puckhaber in College
Station, Texas, found a way to genetically reduce the amount of the
natural toxin known as gossypol in cottonseed.

Stipanovic and Puckhaber are with the ARS Cotton Pathology Research
Unit, part of Southern Plains Agricultural Research Center in College
Station.

The research team showed that by coupling what's known as RNA

interference technology, or RNAi, with a seed-specific gene promoter,
it's possible to significantly reduce gossypol levels within cottonseed and
not reduce the levels of gossypol and related compounds in the foliage.
The presence of these compounds in the foliage helps protect the plant
from attack by insects.

Gossypol is a toxic pigment that can be safely ingested only by ruminant

animals with complex stomachs, so most of the nutritious meal
produced during cottonseed processing is currently sold as cattle feed.

Use of the RNAi technology to develop new cotton lines could lead to
plants with low enough gossypol levels in the seed that the 44 million
metric tons of cottonseed produced yearly could be used to provide
roughly 10 million metric tons of protein. This would help meet the total
protein needs of almost a half billion people.

In addition, U.S. consumers craving a new and nutritious snack food

could soon be reaching for crunchy "TAMU nuts," which were
developed at Texas A&M over 20 years ago. Reduced-gossypol cotton
seeds have a nutty flavor and crunch.

The research was published in a recent edition of the Proceedings of the

National Academy of Sciences.

ARS is the U.S. Department of Agriculture's chief scientific research

agency.

Adapted from materials provided by USDA/Agricultural Research Service.

Need to cite this story in your essay, paper, or report? Use one of the
following formats:
APA

MLA
USDA/Agricultural Research Service (2007, January 27). Technology
Reduces Gossypol In Cotton Seed. ScienceDaily. Retrieved February 7,
2008, from file:///C:/Documents%20and%20Settings/GAURAV
%20GOEL/Desktop/SHEETANSHU%20PROJECT/project
%20links/Technology%20Reduces%20Gossypol%20In%20Cotton
%20Seed.htm

Reducing a toxic compound normally in cottonseed could lead to

production of 10 million metric tons of food-grade protein from cotton
plants every year. (Photo by David Nance)
Ads by Google
Advertise here
Water Fuel
Discover Technology That Uses Water To Run A Car.
www.Fuel-Rebel.com
Biodiesel Plants
Biodiesel Equipment- BioForce9000 Biodiesel Affordable Systems
www.CavitationTechnologies.com
Thilot Seeding Machine
A reliable and durable hand seeding machine
www.hz423.com
Fashion of cotton bags
The new trends of cotton bags กระเป๋ าผ้าแบบใหม่
www.khundaeng.com
MARIBO - Sugar beet seed
Sugar beet seed of superb quality from Danisco Seed.
www.maribo.com

Related Stories

Got Cotton? Texas Researchers' Discovery Could Yield

Protein To Feed Millions (Nov. 20, 2006) — Researchers at the Texas
Agricultural Experiment Station used RNAi to reduce the toxic
compound gossypol from cottonseed to a level that is considered safe for
consumption, but left the compound in ... > read more

Cotton Roots Coaxed Into Producing Promising Compound

(Jul. 28, 2005) — When it comes to cotton, it's usually the plants' soft,
downy fibers that are the focus of Agricultural Research Service (ARS)
scientists. But right now, what's getting their attention is a powerful ...
> read more

Remote Sensing Technique Uses Agricultural Aircraft (Apr. 16, 2005)

— The need for higher resolution images in remote sensing projects has
led to a new technique using agricultural airplanes in the Mississippi ...
> read more

Helping Cotton Thrive In The Heat (Dec. 7, 2004) — Cotton grown

in the United States comes from areas prone to periods of extremely
high temperatures that can have a negative effect on cotton yield.
Agricultural Research Service scientists Michael E. ... > read more