1/2-2012

English Edition
International Journal for Applied Science
Personal Care Detergents Specialties

Alpha-Bisabolol
Naturalness vs. Sustainability?
Natural Sphingolipids and Ceramides
Serenoa Serrulata Fruit Extract
Argan Oil
The Natural Shine Enhancer
Hair Conditioning Ingredients with
Focuson Hair Surface Structure
Vegetable Native Protein
in Shampoo Formulations
Surfactants for Natural
and Organic Cosmetics
Iso-Stearic Acid
in Laundry Detergent Systems

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M. Spiegel*

Alpha-Bisabolol
Naturalness vs. Sustainability?

When thoughts turn to the

responsible use of global
resources, cosmetic raw
materials come under as much
fire as any other resource (1).
One raw material in particular
has been in the headlines
recently: natural Alpha-Bisabolol. This way, natural alphabisabolol can be won in
harmony with the sustainability principle.
Candeia plantation

What Means Sustainability?

The original definition of sustainability
can be traced back into the 16th Century, when a forestry regulation was first
drawn up in 1560 stipulating that only
as much wood may be logged as the forest can still recover from (2).
Since 1992, the term sustainability has
been understood as a three-pillar model
(3). Ecological sustainability is the obligation to sustain the environment for generations to come. Economic sustainability refers to cultivation that conserves
resources. Social sustainability describes
equitable opportunities provided by the
community.
Origin of Bisabolol:

Throughout the Ages

Alpha-bisabolol has been known as an

active ingredient for decades and is used

in many cosmetic and pharmaceutical

products given its good compatibility
and stability. Used as an additive in protection and care products for sensitive
and problematic skin, in sun protection
products, after-sun cosmetics, infant care
products, shaving products and oral hygiene, it is clear how extremely multifunctional it is. This raw material, which
has been used in cosmetics for many
years, has been tested in many scientific
studies that assure its cosmetic and dermatological use.
Natural alpha-bisabolol (sometimes also
called levomenol, which actually refers
to its laevorotatory isomer L--bisabolol)
was first identified in chamomile oil. Bisabolol is obtained from chamomile by
distilling the oil from its flowers, at a
high content of alpha-bisabolol of around
33% (4). Also contained in this oil, at
around 15%, is the blue coloured chamazulene (a name taken from chamomilla,
Latin for chamomile, plus azur, French

for sky blue, and the suffix -lene, for

alkene). Chamazulene arises during distillation from the colourless matricin from
the chamomile flowers and ultimately
leads to colour changes in the final cosmetic or pharmaceutical products.
Since the 1990s, high yields of natural
alpha-bisabolol have been obtainable
from Candeia using a gentle, patented
production process (5). The bark of the
Candeia tree, native of Brazil, contains
oil with a high content of alpha-bisabolol, which can be extracted by steam
distillation. The advantage of this raw
material is that it causes no discoloration
to the final product, and it has a far
lower potential for triggering allergies,
which the sesquiterpene lactones present in chamomile oil are known to do.
Brazil, as the natural habitat of Candeia,
is one of the most species-rich countries
in the world, and is constantly in the
headlines due to claims on how the territory is being used.

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The Brazilian forests currently cover

more than half the total area of the
country, at a total of 520 million hectares
(2010) (7). Some 5.4 million hectares of
this is plantations cultivated for wood
(e.g. eucalyptus, pine, acacia). At around
1% of the forest area, they contribute to
more than 63% of the local wood industry supply. Alongside soy plantations, the
forestry and wood sector has grown into Brazils second most important source
of foreign exchange (8).
Most plant species are native to the primary forests of the Amazonas in the
north of the country. It is this naturally
valuable region that makes the headlines
so often, since swathes of rainforest here
are being cleared at an alarming rate,
among other reasons to make way for
soy and sugar cane plantations. Brazil
has established itself as the secondlargest producer of soy beans at 19% of
the global market, second only to the
USA, and primarily for the animal feed
industry and biodiesel production. Compared to American soy, however, the percentage of genetically modified qualities
is still relatively low. Brazil is also the
leading producer of ethanol (from sugar
cane) (9).
On the east and south-east coasts,
alongside agricultural area, there are
only few remaining areas of the Atlantic rainforest, the Mata Atlantica. This
Atlantic coastal rainforest is an artificial term, since it consists of rainforest,
swamps, mangroves, coastal dune dry
forests and steppe regions.
At the beginning of the 18th century, its
total area was catastrophically reduced
by coffee plantations, as well as by agriculture, cattle farming and heavy population. The meagre 8% of the original
vegetation is now limited to national
parks. Laws govern the protection of
these primary forests and the use of the
secondary forests.
Nature Conservation and the

Prevailing Circumstances

The Brazilian Forest Code, the Cdigo

Florestal, is the central instrument for
nature conservation in Brazil.
It was originally issued in 1945 as a
means to protect the energy supply (fire-

Candeia tree

Candeia blossoms

Fig. 1 Candeia (vernacular) is a tree-like representative of the Asteraceae family

(Eremanthus erythropappus (DC) MacLeish syn. Vanillosmopsis erythropappus).
MacLeish (1987) (6) intensely investigated in the differences between the two
genera Eremanthus and Vanillosmopsis, and ultimately decided that hardly any
difference could be discerned between the two. This is why Candeia also has different botanical names

wood). It stipulated that every landowner must leave one quarter of the original
vegetation on his property untouched,
the Reserva Legal (RL), and also defined
reforestation measures. The amendment
in the 1960s, ultimately aimed at greater
protection of the Amazon region, increased the legal reserve area to 50 percent. Permanently protected areas (reas
de Proteo Permanente, abbreviated
below as APPs) were also defined (10).
Among other changes, the revision of
1996 raised the Reserva Legal even further from 50 to 80 percent.
In May 2011, the Brazilian congress
passed a heavily disputed amendment.
The senate had not made a final decision
by the time of printing. This amended
version favours emergent agriculture
and gives rise to the fear that large areas of the Amazon may be cleared for
logging (11).
Many nature conservation organizations, including WWF (World Wide Fund
For Nature), see four points of critique in
the new bill: Amnesty for wrongdoers,
the reduction of the Reserva Legal and
APP, the waiving of the conservation
quota for small farms, and the fact that
compensation plantations will not have
to be spatially proportionate (12). Above

all, many organizations fear this will lead

to extensive deforestation of the Amazon region.
Sustainable Use of Bisabolol
Candeia, whose oil is used for producing
the natural IMPAG alpha-bisabolol, does
not grow in the Amazon region, rather
mainly in the south-east of Brazil, in the
states Minas Gerais (second-largest state
after So Paulo) and Bahia. Other stocks
are in So Paulo, Rio de Janeiro, Minas
Gerais, Esprito Santo, Paran and Estao Ecolgica da Jureia on the southern stretch of coast. The Candeia plantations are not part of the controversial areas near the Amazon which are constantly in the headlines.
Quite the opposite: Candeia is a lightdemanding tree species that prefers to
grow in sparse woodlands. Studies conducted by UFLA (Universidade Federal de
Lavras, Federal University of Lavras in
Brazil), for example, confirm that Candeia is a pioneer tree species that can
quickly populate grassland and generates relatively pure stocks. As a commercial tree species, it is used not only for its
oil. Its wood has always been used for

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making fence posts as well. Large cultivation areas of Candeia (as well as eucalyptus trees) are found in particular on
degraded areas that were once cleared
and used for agriculture and livestock in
earlier decades (8).
Sustainable Management Plans
In recent years, Brazil has made considerable progress in integrating the principle of sustainability into its plantation
economies. Certification of forestry activities and production in compliance
with ISO, FSC or the Brazilian standard
CERFLOR ensure positive developments
in this respect, since the buying markets
demand proof of ecologically and socially sustainable cultivation, and thereby ensure production is happening to the
latest technical standards and level of
knowledge.

Today, the Candeia wood for IMPAGs

natural alpha-bisabolol comes exclusively from plantations in the state of Bahia
and the south of Minas Gerais, and is obtained in accordance with sustainable
criteria. IMPAG works together with local partners who are cooperating with
the Universidade Federal de Lavras (UFLA)
(13). This educational institute in the
south of Minas Gerais is endeavouring to
achieve sustainable cultivation and land
use in Brazil, and is conducting research
on management systems for Candeia
(14, 15).
These management plans cover a series
of measures:

Selective felling of predefined trees

Reforestation measures to secure the
forest stand
Most effective implementation of
the knowledge gained from research
in consideration of age structures

Securing the livelihoods of farmers

who plant Candeia

Environmentally friendly, economical

and socially acceptable production,
from planting to production of bisabolol.

These measures ultimately serve to

maintain biodiversity and to protect
nature, and are carried out in accordance
with the prevailing environmental laws.
As a producer of alpha-bisabolol, the
IMPAG partner must therefore observe
the Cdigo Florestal, the Brazilian nature
conservation act, as well as the stipulations of the IBAMA (Instituto Brasileiro
do Meio Ambiente e dos Recursos Naturais Renovveis, at federal level) (16)
and of the IEF (Instituto Estadual de Florestas, state forestry authority) (17).
Even transporting forestry products requires authorization and must be accompanied with papers, called ATPFs.

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These are issued by IBAMA and are proof

of the origin of the wood, as a measure
to prevent illegal logging.
In Portaria No. 234 (supplemented by
No. 01/2007), IEF prescribes cultivation
plans for the production of Candeia in
Minas Gerais. The foremost concern is
the principle of sustainability and biodiversity. This approval can only be given
by IEF upon compliance with a specific
procedure.
Another enactment of the state of Minas Gerais (No. 43,710 von 2004 / Law
No. 14,309 of 2002) stipulates, among
other things, the consideration of biodiversity protection in the use of natural
resources and land. Furthermore, any intended use of the Candeia stocks requires the purchase of permits called
APEFs (Authorizations for Forestry Explorations).
Companies can now become certified
according to the forest management
plans by the FSC (18) (Forest Stewardship Council). The FSC is a global, independent, non-governmental umbrella organization. FSC aims to promote environmentally appropriate, socially beneficial
and economically viable forest cultivation.

The partner and producer of natural IMPAG bisabolol expects to become FSC
certified soon on the merits of its sustainable cultivation.
As a long time supplier of natural alpha
bisabolol, IMPAG applied for ECOCERT
compliance for the active ingredient,
which was granted in 2010. This affirms
that it is an ingredient obtained from renewable resources and produced in an
environmentally sound process.
Advantages of Natural

Alpha-Bisabolol

Bisabolol is a much studied, healing-promoting ingredient. It is highly suitable

for sensitive, impure and problematic
skin. It counteracts the skin reddening
(19) induced by exposure to UV light. This
action has long been known and is described in numerous publications (20).
Furthermore, natural bisabolol has good
anti-inflammatory (antiphlogistic, antiproliferative) and regenerative properties (21). Also much studied are its antibacterial (22) and antimycotic effects,
as well as its use in pharmaceutical applications (23, 24).

Synthetic or Natural

Alpha-Bisabolol ?

Bisabolol refers to the - and -isomers

of the chemical compound bisabolol, for
each of which an enantiomer (mirror image) exists. It is a monocyclic sesquiterpene alcohol. Most predominant in nature is ()--bisabolol. There is a synthetic bisabolol available, produced in a
patented method from farnesol or
nerolidol (an isomer of farnesol, a
sesquiterpene alcohol), which is transformed together with a mixture of a ketone, a sulfonic acid and perchloric acid
(25). While this product can be purified
(26), it still contains trace amounts of
farnesol, at about 0.5%.
The difference between natural and synthetic bisabolol is the content of the
active ()-alpha-bisabolol isomer. The
synthetic product contains only about
42.5% ()-alpha-bisabolol, while the
natural product contains at least 97%.
Since the above mentioned effects of
bisabolol are attributed to the alpha-bisabolol isomer, the synthetic quality must
be employed at relatively high concentration (27).

Fig. 2 Primary forests of the Amazon (in the north of the country) and the Atlantic coastal rainforest where Candeia forests
grow

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Properties of Natural

Alpha-Bisabolol

Bisabolol is a clear, colourless to very

slightly yellowish liquid of medium viscosity. Its odour is very faint and slightly flowery-sweet.
Applications:
For face and body care products, skin
protection, sun protection products, baby care, aftershaves, mouthwashes and
dental care.
Possible Application Concentrations:
approx. 0,07 - 1%, for example:

0,07%: Lipstick products

0,2%: Products against dry skin,

products for skin regeneration, sun
protection and after-sun products,
body care products, aftershave products, scrubs, depilation products

0,1%: Oils and childrens products,

anti-acne products, hair protection
preparations

0,06%: Make-up

0,15%: Hand care creams.

Conclusion
Natural alpha-bisabolol obtained from
Candeia can be produced in harmony
with the principle of sustainability. The
diverse effects of alpha-bisabolol have
been comprehensively demonstrated in
many studies.
This natural raw material, which is also
available in an ECOCERT-compliant version, is therefore an indispensable, valuable component of modern cosmetics
and pharmaceutical products.
Literature
(1)

Cropwatch: Threatened Species Contd: The

Brazilian Candeia Plant (Eremanthus erythropappus (DC) MacLeish). Modified (Feb
2009) from Cropwatch Newsletter 8; www.
cropwatch.org Stand 11/2011

(2)

Bundesregierung: Nachhaltigkeit (http://www.

dialog-nachhaltigkeit.de/nachhaltigkeit.html
Stand 11/2011)

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(3)

BUND: Erfolgsgeschichte eines Begriffs (http://

www.bund-bawue.de/themen-projekte/nach
haltigkeit/ Stand 11/2011)

(4)

Goethe Universitt, Fachbereich Pharmazie:

Echte Kamille (http://www.pharmazie.uni-frank
furt.de/Neuer_Senckenbergischer_Arznei
pflanzengarten/Kraempfe/Matricaria.html),
Stand 11/2011)

(5)

Lauterbach et al.: Purification of .alpha.-bisabolol U.S. Patent 5,132,471, July 21, 1992

(6)

MacLeish N.F.F. (1987) Revision of Eremanthus (Compositae: Vernonieae). Annals of

the Missouri Botanical Garden 74(2), 265-290

(7)

BPB: Globalisierung (http://www.bpb.de/wis

sen/0XZOJP,0,0,Jaehrliche_Aenderung_der_
Waldbestaende.html, Stand 11/2011)

(8)

Nutto, L. (2007): Die Eukalyptus-Plantagenwirtschaft in Brasilien. Nachhaltige Holzproduktion oder kologisches Desaster? Wald
Holz 88, 6: 49-53

(9)

ntv: Biosprit-Anbau zerstrt Regenwald

(http:// www.n-tv.de/wissen/Biosprit-Anbauzerstoert-Regenwald-article717821.html,
Stand 11/2011)

setz in Gefahr (http://www.tropenwaldnetzwerk-brasilien.de/codigo-florestal%E2%80%93-brasiliens-waldschutzgesetz

gefahr, Stand 11/2011)
(13) Clark A., Khweiss N., Salazar L., Verdadero L.:
Promoting Sustainability in the Value Chain
of Natural Bisabolol, a Brazilian Rainforest
Product School of International and Public
Affairs, SIPA at Columbia University, May
2011
(14) Prez J.F.M, de Oliveira A.D., de Mello J.M.,
Borges L.F.R., Camolesi J.F. (2004): Management system for native Candeia forest (Eremanthus erythropappus (DC) MacLeish) - the
option for selective cutting. Cerne, 10 (2),
257-273
(15) De Oliveira A.D., Ribeiro I. S., Scolforo J.R.S.,
De Mello J. M., De Rezende J. L. P.: Economic
Analysis of Sustainable Managemeng of Candeia (received: February 5, 2009; accepted:
April 30, 2010) http://www.dcf.ufla.br/cerne/
artigos/25-10-20105225v16_n3_artigo%
2009.pdf
(16) IBAMA: Instituto Brasileiro do Meio Ambiente
e dos Recursos Naturais Renovveis
(www.ibama.gov.br)

(21) Jellinek J.S. (1984) Alpha-bisabolol un agent

anti-inflammatoire pour produits cosmtiques. Parfums Cosmet. Aromes 57, 55-57
(22) Brehm-Stecher, B. F., Johnson, E. A.: Sensitization of Staphylococcus aureus and Escherichia coli to Antibiotics by the Sesquiterpenoids Nerolidol, Farnesol, Bisabolol, and
Apritone. Antimicrob Agents Chemother.
2003 October; 47(10): 33573360
(23) Kadir R., Barry BW., alpha-Bisabolol, for possible escapes penetration enhancer for dermal and transdermal therapeutics Int J Pharmaceutics 1991; 70:87-94
(24) Hahn B., Holzl J., Absorption, distribution and
metabolism of [14C]-levomenol in the skin.
Arzneimittelforschung 1987 Jun; 37(6): 71620
(25) Symrise GmbH & Co. KG: Verfahren zur Herstellung von alpha-Bisabolol aus Nerolidol,
DE10246038B3 15.04.2004
(26) Symrise GmbH & Co. KG: Verfahren zum Entfernen von Farnesol aus Mischungen mit alpha-Bisabolol, DE102005051903A1
03.05.2007.
(27) Marti, M.E.: SOFW Journal 117, 626 (1991)

(10) Konrad-Adenauer-Stiftung e.V.: Online-Publikation August 2011: Das neue brasilianische

Waldschutzgesetz (Cdigo Florestal) -Modifikation und mgliche Konsequenzen (http://
www.kas.de/wf/doc/4432-1442-1-30.pdf
Stand 11/2011)
(11) Brasilien Nachrichten (http://www.brasiliennachrichten.de/index.php?option=com_cont
ent&task=view&id=94&Itemid=31&limit=1&
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(12) Uta Grunert, Tropenwaldnetzwerk Brasilien:
Codigo florestal Brasiliens Waldschutzge-

(17) IEF: Instituto Estadual de Florestas

(http://www.ief.mg.gov.br/)
(18) Forest Stewardship Council, FSC
(http://www.fsc.org/)
(19) Stanzl K, Vollhardt J. The Case of alpha-Bisabolol. Handbook of cosmetic science and
technology. (2001), 24: 277
(20) Jakovlev V., Schlichtegroll A.: Anti-inflammatory activity of (-) Alpha-Bisabolol, an essential component of chamomila oil. Arzneimittelforschung, 1969, 19(4), 615-616

* Authors address:
Dipl.-Biologin Martina Spiegel
IMPAG GmbH
Fritz-Remy-Strae 25
63071 Offenbach am Main
Germany
Email: martina.spiegel@impag.de

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