Pantothenic acid

Pantothenic acid, also called vitamin B5 (a B vitamin), is a water-soluble

Pantothenic acid
vitamin. Pantothenic acid is an essential nutrient. Animals require pantothenic
acid in order to synthesize coenzyme-A (CoA), as well as to synthesize and
metabolize proteins, carbohydrates, and fats. The anion is called pantothenate.

Pantothenic acid is theamide between pantoic acid and β-alanine. Its name derives
from the Greek pantothen, meaning "from everywhere", and small quantities of
pantothenic acid are found in nearly every food, with high amounts in fortified
whole-grain cereals, egg yolks, liver and dried mushrooms.[7][8] It is commonly
found as its alcohol analog, the provitamin panthenol (pantothenol), and as
calcium pantothenate.
Names
Pantothenic acid was discovered byRoger J. Williams in 1933.[9] Preferred IUPAC name
3-[(2R)-2,4-Dihydroxy-3,3-
dimethylbutanamido]propanoic
acid
Contents Systematic IUPAC name
Biological role 3-[(2R)-(2,4-Dihydroxy-3,3-
dimethylbutanoyl)amino]propanoic
Sources acid
Dietary
Supplementation
Identifiers

Dietary recommendations
CAS 599-54-2
Number
Absorption 79-83-4 (R)
Deficiency 3D model Interactive image
Toxicity (JSmol)
(R): Interactive image
Research
(S): Interactive image
Ruminant nutrition
3DMet B00193
References
Beilstein 1727062, 1727064 (R)
Reference

Biological role ChEBI CHEBI:7916

Only the dextrorotatory (D) isomer of pantothenic acid possesses biologic

ChEMBL ChEMBL1594
activity.[10] The levorotatory (L) form may antagonize the effects of the ChemSpider 963
dextrorotatory isomer.[11]
6361 (R)
Pantothenic acid is used in the synthesis of coenzyme A (CoA). Coenzyme A may 4677898 (S)
act as an acyl group carrier to form acetyl-CoA and other related compounds; this DrugBank DB01783
is a way to transport carbon atoms within the cell.[12] CoA is important in energy
metabolism for pyruvate to enter the tricarboxylic acid cycle (TCA cycle) as
ECHA 100.009.061
acetyl-CoA, and for α-ketoglutarate to be transformed to succinyl-CoA in the
InfoCard
cycle.[13] CoA is also important in the biosynthesis of many important compounds EC Number 209-965-4
such as fatty acids, cholesterol, and acetylcholine.[13] CoA is incidentally also KEGG D07413
required in the formation of ACP,[14] which is also required for fatty acid
MeSH Pantothenic+Acid
synthesis in addition to CoA.[12]
PubChem
CID
Pantothenic acid in the form of CoA is also required for acylation and acetylation, CID 988
which, for example, are involved in signal transduction and enzyme activation and 6613 (R)
deactivation, respectively.[15]
5748353 (S)
Since pantothenic acid participates in a wide array of key biological roles, it is RTECS RU4729000
essential to all forms of life.[10][8] As such, deficiencies in pantothenic acid may number
have numerous wide-ranging effects.
UNII 19F5HK2737

InChI
Sources
SMILES
Properties
Dietary Chemical C9H17NO5
Content of pantothenic acid varies among manufactured and natural foods, formula
especially fortified ready-to-eat cereals, infant formulas, energy bars and dried Molar mass 219.237 g·mol−1
foods.[7] Major food sources of pantothenic acid are dried shiitake mushrooms, Appearance Yellow oil
liver, kidney, egg yolks and sunflower seeds.[7] Whole grains are another source Colorless crystals (Ca2+
of the vitamin, but milling removes much of the pantothenic acid, as it is found in salt)
the outer layers of whole grains.[16] In animal feeds, the most important sources
Odor Odorless
are alfalfa, cereal, fish meal, peanut meal, molasses, mushrooms, rice, wheat bran,
and yeasts.[17] Density 1.266 g/cm3
1.32 g/cm3 (Ca2+ salt)[1]
Melting 183.833 °C
Supplementation point (362.899 °F; 456.983 K)
The derivative of pantothenic acid, pantothenol (panthenol), is a more stable form 196–200 °C (385–
of the vitamin and is often used as a source of the vitamin in multivitamin 392 °F; 469–473 K)
supplements. Another common supplemental form of the vitamin is calcium decomposes (Ca2+
pantothenate. Calcium pantothenate is often used in dietary supplements because, salt)[1][3][5]
as a salt, it is more stable than pantothenic acid.[17] 138 °C (280 °F; 411 K)
decomposes (Ca2+ salt,
Dietary recommendations monohydrate)[6]
Solubility in Very soluble[2]
The U.S. Institute of Medicine (IOM) updated Estimated Average Requirements water 2.11 g/mL (Ca2+ salt)[1]
(EARs) and Recommended Dietary Allowances (RDAs) for B vitamins in 1998.
At that time there was not sufficient information to establish EARs and RDAs for
Solubility Very soluble in C6H6,
pantothenic acid. In instances such as this, the Board sets Adequate Intakes (AIs),
ether[2]
with the understanding that at some later date, AIs will be replaced by more exact
Ca2+ salt:
information. The current AI for teens and adults ages 14 and up is 5 mg/day. AI
Slightly soluble in
for pregnancy is 6 mg/day. AI for lactation is 7 mg/day. For infants up to 12
alcohol, CHCl3[3]
months the AI is 1.8 mg/day. For children ages 1–13 years the AI increases with log P −1.416[4]
age from 2 to 4 mg/day. As for safety, the IOM sets Tolerable upper intake levels Acidity (pKa) 4.41[5]
(ULs) for vitamins and minerals when evidence is sufficient. In the case of
Basicity 9.698
pantothenic acid there is no UL, as there is no human data for adverse effects from
(pKb)
high doses. Collectively the EARs, RDAs, AIs and ULs are referred to as Dietary
Chiral +37.5°
Reference Intakes (DRIs).[16]
rotation +24.3° (Ca2+ salt)[5]
([α]D)
The European Food Safety Authority (EFSA) refers to the collective set of
information as Dietary Reference Values, with Population Reference Intake (PRI) Hazards
instead of RDA, and Average Requirement instead of EAR. AI and UL are NFPA 704
defined the same as in the U.S. For women and men over age 11 the Adequate
1
Intake (AI) is set at 5 mg/day. AI for pregnancy is 5 mg/day, for lactation
2 0
7 mg/day. For children ages 1–10 years the AI is 4 mg/day. These AIs are similar
to the U.S. AIs.[18] The EFSA also reviewed the safety question and reached the Flash point 287.3 °C (549.1 °F;
same conclusion as in United States - that there was not sufficient evidence to set 560.5 K)[6]
a UL for pantothenic acid.[19] Lethal dose or concentration (LD, LC):

For U.S. food and dietary supplement labeling purposes the amount in a serving is
LD50 > 10 mg/g (Ca2+ salt)[3]
(median
expressed as a percent of Daily Value (%DV). For pantothenic acid labeling dose)
purposes 100% of the Daily Value was 10 mg, but as of May 27, 2016 it was
Related compounds
revised to 5 mg to bring it into agreement with the AI.[20] A table of the old and
Related Arginine
new adult Daily Values is provided at Reference Daily Intake. Food and
alkanoic Hopantenic acid
[21]
supplement companies have until January 1, 2020 to comply with the change. acids
4-(γ-
Age group Age Adequate intake[16] Glutamylamino)butanoic
acid
Infants 0–6 months 1.7 mg
Related Panthenol
Infants 7–12 months 1.8 mg compounds
Children 1–3 years 2 mg Except where otherwise noted, data
Children 4–8 years 3 mg
are given for materials in their
standard state (at 25 °C [77 °F],
Children 9–13 years 4 mg 100 kPa).
Adult men and women 14+ years 5 mg verify (what is ?)
Pregnant women (vs. 5) 6 mg Infobox references
Breastfeeding women (vs. 5) 7 mg

Absorption
When found in foods, most pantothenic acid is in the form of CoA or bound to acyl carrier protein (ACP). For the intestinal cells to
absorb this vitamin, it must be converted into free pantothenic acid. Within the lumen of the intestine, CoA and ACP are hydrolyzed
into 4'-phosphopantetheine. The 4'-phosphopantetheine is then dephosphorylated into pantetheine. Pantetheinase, an intestinal
[22]
enzyme, then hydrolyzes pantetheine into free pantothenic acid.

Free pantothenic acid is absorbed into intestinal cells via a saturable, sodium-dependent active transport system.[13] At high levels of
intake, when this mechanism is saturated, some pantothenic acid may also be absorbed via passive diffusion.[17] As intake increases
10-fold, however, absorption rate decreases to 10%.[13]

Deficiency
Pantothenic acid deficiency is exceptionally rare and has not been thoroughly studied. In the few cases where deficiency has been
[13]
seen (victims of starvation and limited volunteer trials), nearly all symptoms can be reversed with the return of pantothenic acid.

Symptoms of deficiency are similar to other vitamin B deficiencies. There is impaired energy production, due to low CoA levels,
which could cause symptoms of irritability, fatigue, and apathy.[13] Acetylcholine synthesis is also impaired; therefore, neurological
symptoms can also appear in deficiency;[23] they include numbness, paresthesia, and muscle cramps.[23] Deficiency in pantothenic
acid can also cause hypoglycemia, or an increased sensitivity to insulin.[13] Insulin receptors are acylated with palmitic acid when
they do not want to bind with insulin.[22] Therefore, more insulin will bind to receptors when acylation decreases, causing
hypoglycemia.[12] Additional symptoms could include restlessness, malaise, sleep disturbances, nausea, vomiting, and abdominal
cramps.[23] In a few rare circumstances, more serious (but reversible) conditions have been seen, such as adrenal insufficiency and
hepatic encephalopathy.

Deficiency symptoms in other nonruminant animals include disorders of the nervous, gastrointestinal, and immune systems, reduced
[24]
growth rate, decreased food intake, skin lesions and changes in hair coat, and alterations in lipid and carbohydrate metabolism.
Toxicity
Toxicity of pantothenic acid is unlikely. In fact, no Tolerable Upper Level Intake (UL) has been established.[16] Large doses of the
vitamin, when ingested, have no reported side effects and massive doses (e.g., 10 g/day) may only yield mild diarrhea.[13] There are
also no adverse reactions known following parenteral (injected) or topical (skin) applications of the vitamin.[25] Pantothenic acid, in
an animal study, was shown to induce adrenal hyper-responsiveness to stress stimulation.[26]

Research
Although pantothenic acid supplementation is under preliminary research for a variety of human diseases, there is insufficient
evidence to date that it has any effect.[10][8]

Ruminant nutrition
No dietary requirement for pantothenic acid has been established as synthesis of pantothenic acid by ruminal microorganisms appears
to be 20 to 30 times more than dietary amounts. Net microbial synthesis of pantothenic acid in the rumen of steer calves has been
estimated to be 2.2 mg/kg of digestible organic matter consumed per day. The degradation of dietary intake of pantothenic acid is
considered to be 78 percent. Supplementation of pantothenic acid at 5 to 10 times theoretic requirements did not improve
performance of feedlot cattle.[27]

References
1. "Scientific Opinion on the safety and efficacy of pantothenic acid (calcium D-pantothenate and D-panthenol) as a
feed additive for all animal species based on a dossier submitted by Lohmann Animal Health". EFSA Journal.
Parma, Italy: European Food Safety Authority. 9 (11): 2409. 2011. doi:10.2903/j.efsa.2011.2409(https://doi.org/10.2
903%2Fj.efsa.2011.2409).
2. Lide, David R., ed. (2009).CRC Handbook of Chemistry and Physics(90th ed.). Boca Raton, Florida: CRC Press.
ISBN 978-1-4200-9084-0.
3. "Calcium D-pantothenate"(http://www.chemicalland21.com/lifescience/foco/CALCIUM%20PANTOTHENATE.htm).
AroKor Holdings Inc. Retrieved 2014-09-05.
4. "MSDS of D-pantothenic acid"(http://www.hmdb.ca/system/metabolites/msds/000/000/148/original/HMDB00210.pd
f?1358462271) (PDF). Human Metabolome Database. Retrieved 2014-09-05.
5. Leenheer, André P. De; Lambert, Willy E.; Bocxlaer, Jan F. Van, eds. (2000). Modern Chromatographic Analysis Of
Vitamins: Revised And Expanded(https://books.google.com/books?id=8UppGvIN_t0C&pg=P A533).
Chromatographic Science.84 (3rd ed.). Marcel Dekker. p. 533. ISBN 978-0-203-90962-1.
6. "DL-Pantothenic acid calcium salt"(http://www.guidechem.com/products/6381-63-1.html). Retrieved 2014-09-05.
7. "Pantothenic acid ordered by nutrient content per 100 g"(https://ndb.nal.usda.gov/ndb/nutrients/report?nutrient1=41
0&nutrient2=&nutrient3=&&max=25&subset=0&of fset=0&sort=c&totCount=6356&measureby=g) . US Department of
Agriculture National Nutrient Database. October 2016. Retrieved 25 October 2016.
8. "Pantothenic Acid" (http://lpi.oregonstate.edu/infocenter/vitamins/pa/)
. Linus Pauling Institute at Oregon State
University. Micronutrient Information Center. Retrieved 7 November 2010.
9. Richards, Oscar W. (1938). "The Stimulation of Yeast Proliferation By Pantothenic Acid" (http://www.jbc.org/content/1
13/2/531.full.pdf) (PDF). Journal of Biological Chemistry. 113 (2): 531–536.
10. "Pantothenic acid (Vitamin B5)" (https://www.nlm.nih.gov/medlineplus/druginfo/natural/patient-vitaminb5.html).
MedlinePlus, U.S. National Library of Medicine, National Institutes of Health. 2016.
11. Kimura S, Furukawa Y, Wakasugi J, Ishihara Y, Nakayama A (1980). "Antagonism of L(-)pantothenic acid on lipid
metabolism in animals".J. Nutr. Sci. Vitaminol. 26 (2): 113–7. doi:10.3177/jnsv.26.113 (https://doi.org/10.3177%2Fjn
sv.26.113). PMID 7400861 (https://www.ncbi.nlm.nih.gov/pubmed/7400861).
12. Voet, D., Voet, J.G., Pratt, C.W. (2006). Fundamentals of Biochemistry: Life at the Molecular Level, 2nd ed.
Hoboken, NJ: John Wiley & Sons, Inc.
13. Gropper, S. S, Smith, J. L., Groff, J. L. (2009). Advanced nutrition and human metabolism.Belmont, CA: Wadsworth,
Cengage learning.
14. Sweetman, L. (2005). Pantothenic Acid. Encyclopedia of Dietary Supplements.
1: 517-525.
15. Gropper, S. S, Smith, J. L., Groff, J. L. (2009). Advanced nutrition and human metabolism.Belmont, CA: Wadsworth,
Cengage learning
16. Institute of Medicine (1998). "Pantothenic Acid" (http://www.nap.edu/openbook.php?record_id=6015&page=357).
Dietary Reference Intakes for Thiamin, Riboflavin, Niacin, iVtamin B6, Folate, Vitamin B12, Pantothenic Acid, Biotin,
and Choline. Washington, DC: The National Academies Press. pp. 357–373. ISBN 978-0-309-06554-2. Retrieved
2017-08-29.
17. Combs, G. F. (2008). The Vitamins: Fundamental Aspects in Nutrition and Health (3rd ed.). Boston: Elsevier.
ISBN 978-0-12-183493-7.
18. "Overview on Dietary Reference Values for the EU population as derived by the EFSA Panel on Dietetic Products,
Nutrition and Allergies"(https://www.efsa.europa.eu/sites/default/files/assets/DRV_Summary_tables_jan_17.pdf)
(PDF). 2017.
19. "Tolerable Upper Intake Levels For Vitamins And Minerals" (http://www.efsa.europa.eu/sites/default/files/efsa_rep/blo
bserver_assets/ndatolerableuil.pdf)(PDF). European Food Safety Authority. 2006.
20. "Federal Register May 27, 2016 Food Labeling: Revision of the Nutrition and Supplement Facts Labels"
(https://ww
w.gpo.gov/fdsys/pkg/FR-2016-05-27/pdf/2016-11867.pdf) (PDF).
21. "Changes to the Nutrition Facts Panel - Compliance Date"(https://www.fda.gov/Food/GuidanceRegulation/Guidance
DocumentsRegulatoryInformation/LabelingNutrition/ucm385663.htm#dates)
22. Trumbo, P. R. (2006). "Pantothenic Acid".In Shils, M. E.; Shike, M.; Ross, A. C.; Caballero, B.; Cousins, R. J.
Modern Nutrition in Health and Disease(10th ed.). Philadelphia, PA: Lippincott Williams & Wilkins. pp. 462–467.
ISBN 978-0-7817-4133-0.
23. Otten, J. J., Hellwig, J. P., Meyers, L. D. (2008). Dietary reference intakes: The essential guide to nutrient
requirements. Washington, DC: The National Academies Press
24. Smith, C. M.; Song, W. O. (1996). "Comparative nutrition of pantothenic acid".Journal of Nutritional Biochemistry. 7
(6): 312–321. doi:10.1016/0955-2863(96)00034-4(https://doi.org/10.1016%2F0955-2863%2896%2900034-4) .
25. Combs, G. F. Jr. (1998). The Vitamins: Fundamental Aspects in Nutrition and Health (2nd ed.). Ithaca, NY: Elsevier
Academic Press. p. 374.ISBN 978-0-12-183492-0.
26. Jaroenporn S; Yamamoto T (2008). "Effects of pantothenic acid supplementation on adrenal steroid secretion from
male rats". Biol Pharm Bull. 31 (6): 1205–8. doi:10.1007/s12522-011-0113-6(https://doi.org/10.1007%2Fs12522-011
-0113-6). PMID 18520055 (https://www.ncbi.nlm.nih.gov/pubmed/18520055).
27. National Research Council. 2001. Nutrient Requirements of Dairy Cattle. 7th rev
. ed. Natl. Acad. Sci., Washington,
DC.

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