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Encyclopedia > Pantothenic acid
Pantothenic acid
IUPAC name 3-[(2,4-dihydroxy-3, 3-dimethyl-1-oxobutyl) amino]propanoic acid
Identifiers
CAS number 137-08-6
PubChem 988
SMILES CC(C)(CO)C(C(=O)NCCC(=O)O)O
Properties
Molecular formula C9H17NO5
Molar mass 219.235
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

Pantothenic acid, also called vitamin B5 (a B vitamin), is a water-soluble vitamin required to sustain life (essential nutrient). Pantothenic acid is needed to form coenzyme-A (CoA), and is critical in the metabolism and synthesis of carbohydrates, proteins, and fats. Chemically it is the amide between D-pantoate and beta-alanine. Its name is derived from the Greek pantothen (παντόθεν) meaning "from everywhere" and small quantities of pantothenic acid are found in nearly every food, with high amounts in whole grain cereals, legumes, eggs, meat, and royal jelly. It is commonly found as its alcohol analog, the provitamin panthenol, and as calcium pantothenate. Image File history File links No higher resolution available. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... PubChem is a database of chemical molecules. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... This article or section does not cite any references or sources. ... This article does not cite any references or sources. ... In chemistry, the standard state of a material is its state at 1 bar (100 kilopascals) and 25 degrees Celsius (298. ... Retinol (Vitamin A) For the record label, see Vitamin Records A vitamin is an organic compound required in tiny amounts for essential metabolic reactions in a living organism. ... Vitamin B is a complex of several vitamins. ... It has been suggested that this article or section be merged with Solution. ... An essential nutrient is a nutrient required for normal body functioning that cannot be synthesized by the body. ... Coenzyme A (CoA, CoASH, or HSCoA) is a coenzyme, notable for its role in the synthesis and oxidization of fatty acids, and the oxidation of pyruvate in the citric acid cycle. ... Lactose is a disaccharide found in milk. ... A representation of the 3D structure of myoglobin, showing coloured alpha helices. ... For other uses, see FAT. Fats consist of a wide group of compounds that are generally soluble in organic solvents and largely insoluble in water. ... Non-essential, beta-alanine is the only naturally occurring beta amino acid; however, this biochemical is not used in the biosynthesis of any major proteins or enzymes. ... This article or section does not cite its references or sources. ... This article is about cereals in general. ... Varieties of soybean seeds, a popular legume Pea pods A legume is a plant in the family Fabaceae (or Leguminosae), or a fruit of these plants. ... An egg is a body consisting of an ovum surrounded by layers of membranes and an outer casing of some type, which acts to nourish and protect a developing embryo. ... Kinnikuman character, see Meat Alexandria. ... To meet Wikipedias content policies, the external links section for this article may require cleanup. ... A provitamin is a substance that can be converted into a vitamin by animal tissues. ... Panthenol is the alcohol analog of pantothenic acid (vitamin B5), and is thus the provitamin of B5. ...


Bold text== Biologic role == Only the dextrorotatory (D) isomer of pantothenic acid possesses biologic activity. [1] The levorotatory (L) form may antagonize the effects of the dextrorotatory isomer.[2]


Pantothenic acid is used in the synthesis of coenzyme A (abbreviated as CoA). Coenzyme A may act as an acyl group carrier to form acetyl-CoA and other related compounds; this is a way to transport carbon atoms within the cell. The transfer of carbon atoms by coenzyme A is important in cellular respiration, as well as the biosynthesis of many important compounds such as fatty acids, cholesterol, and acetylcholine. Coenzyme A (CoA, CoASH, or HSCoA) is a coenzyme, notable for its role in the synthesis and oxidization of fatty acids, and the oxidation of pyruvate in the citric acid cycle. ... In chemistry, the terms acyl or acyl group refer to a functional group obtained from an acid by removal of a hydroxyl group. ... Categories: Biochemistry stubs | Thiols ... General Name, symbol, number carbon, C, 6 Chemical series nonmetals Group, period, block 14, 2, p Appearance black (graphite) colorless (diamond) Standard atomic weight 12. ... Cellular respiration describes the metabolism reactions and processes that take place in a cell to obtain biochemical energy from fuel molecules. ... In chemistry, especially biochemistry, a fatty acid is a carboxylic acid often with a long unbranched aliphatic tail (chain), which is either saturated or unsaturated. ... Cholesterol is a sterol (a combination steroid and alcohol), a lipid found in the cell membranes of all body tissues, and is transported in the blood plasma of all animals. ... The chemical compound acetylcholine, often abbreviated as ACh, was the first neurotransmitter to be identified. ...


Since pantothenic acid participates in a wide array of key biological roles, it is considered essential to all forms of life[3]. As such, deficiencies in pantothenic acid may have numerous wide-ranging effects, as discussed below Italic text

Contents

Sources

Small quantities of pantothenic acid are found in most foods,[4] with high quantities found in whole grain and eggs. Pantothenic acid can also be found in many dietary supplements (as calcium-D-pantothenate), and some energy drink companies are now adding pantothenic acid to their beverages. This article or section does not cite its references or sources. ... An egg is a body consisting of an ovum surrounded by layers of membranes and an outer casing of some type, which acts to nourish and protect a developing embryo. ... A variety of energy drinks are available; the skinny bullet can shape is popular. ...


A recent study also suggests that gut bacteria in humans can generate pantothenic acid[5].


Daily requirement

Pantothenate in the form of pantethine is considered to be the more active form of the vitamin in the body, but is unstable at high temperatures or when stored for long periods, so calcium pantothenate is the more usual form of vitamin B5 when it is sold as a dietary supplement. 10 mg of calcium pantothenate is equivalent to 9.2 mg of pantothenic acid. Pantethine (Bis-pantethine) or Co-enzyme pantethine is a dimeric form of vitamin B5, composed of two molecules of pantothenic acid linked by cysteamine bridging groups. ... A dietary supplement is intended to supply nutrients, (vitamins, minerals, fatty acids or amino acids) that are missing or not consumed in sufficient quantity in a persons diet. ...

Age group Age Requirements

(in mg per day)

infants 0-6 months 1.7
infants 7-12 months 2
children 4-8 years 3
children 9-13 years 4
adolescents 14-18 years 5
adults 19 years and older 5
pregnant women 6
breastfeeding women 7
  • United Kingdom RDA: 6 mg/day

Deficiency

Pantothenic acid deficiency is exceptionally rare and has not been thoroughly studied. In the few cases where deficiency has been 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. Most are minor, including fatigue, allergies, nausea, and abdominal pain. In a few rare circumstances more serious (but reversible) conditions have been seen, such as adrenal insufficiency and hepatic encephalopathy. Vitamin B is a complex of several vitamins. ... An allergy is an abnormal, acquired sensitivity to a given substance, including pollen, drugs, or numerous environmental triggers. ... In mammals, the adrenal gland (also known as suprarenal glands) are the triangle-shaped endocrine glands that sit on top of the kidneys; their name indicates that position (ad, near or at + renes, kidneys). They are chiefly responsible for regulating the stress response through the synthesis of corticosteroids and catecholamines... Hepatic encephalopathy is a potentially reversible neuropsychiatic abnormality in the setting of liver failure, whether chronic (as in cirrhosis), or acutely. ...


Notably, painful burning sensations of the feet were reported in tests conducted on volunteers. Deficiency of pantothenic acid may explain similar sensations reported in malnourished prisoners of war[3].


Disputed uses

Given pantothenic acid's prevalence among living things and the limited body of studies in deficiency, many "alternative" uses of pantothenic acid have been devised.


Hair care

Mouse models identified skin irritation and loss of hair color as possible results of severe pantothenic acid deficiency.[citation needed] As a result, the cosmetic industry began adding pantothenic acid to various cosmetic products, including shampoo. These products, however, showed no benefits in human trials.[citation needed] Despite this, many cosmetic products still advertise pantothenic acid additives.


Acne

Following from discoveries in mouse trials[citation needed], in the late 1990s a small study was published promoting the use of pantothenic acid to treat acne vulgaris. Different types of Acne Vulgaris: A: Cystic acne on the face, B: Subsiding tropical acne of trunk, C: Extensive acne on chest and shoulders. ...


According to a study published in 1995 by Dr. Lit-Hung Leung[6], high doses of Vitamin B5 resolved acne and decreased pore size. Dr. Leung also proposes a mechanism, stating that CoA regulates both hormones and fatty-acids, and without sufficient quantities of pantothenic acid, CoA will preferentially produce androgens.[citation needed] This causes fatty acids to build up and be excreted through sebaceous glands, causing acne.[citation needed] Leung's study gave 45 Asian males and 55 Asian females varying doses of 10-20g of pantothenic acid (100,000%-200,000% of the US Daily Value), 80% orally and 20% through topical cream. Leung noted improvement of acne within one week to one month of the start of the treatment.[citation needed] Coenzyme A (CoA, CoASH, or HSCoA) is a coenzyme, notable for its role in the synthesis and oxidization of fatty acids, and the oxidation of pyruvate in the citric acid cycle. ... Coenzyme A (CoA, CoASH, or HSCoA) is a coenzyme, notable for its role in the synthesis and oxidization of fatty acids, and the oxidation of pyruvate in the citric acid cycle. ... Androgen is the generic term for any natural or synthetic compound, usually a steroid hormone, that stimulates or controls the development and maintenance of masculine characteristics in vertebrates. ... The sebaceous glands are glands found in the skin of mammals. ...


Critics are quick to point out the flaws in Dr. Leung's study, however. Dr. Leung's study was not a double-blind placebo controlled trial. To date, the only study looking at the effect of Vitamin B5 on acne is Dr. Leung's, and few if any dermatologists prescribe high-dose pantothenic acid. Furthermore, there is no evidence documenting acetyl-CoA regulation of androgens instead of fatty acids in times of stress or limited availability, since fatty acids are also necessary for life. Androgen is the generic term for any natural or synthetic compound, usually a steroid hormone, that stimulates or controls the development and maintenance of masculine characteristics in vertebrates. ... In chemistry, especially biochemistry, a fatty acid is a carboxylic acid (or organic acid), often with a long aliphatic tail (long chains), either saturated or unsaturated. ...


Diabetic Peripheral polyneuropathy

28 out of 33 patients (84,8%) previously treated with alpha-lipoic acid for peripheral polyneuropathy reported further improvement after combination with pantothenic acid. The theoretical basis for this is that both substances intervene at different sites in pyruvate metabolism and are thus more effective than one substance alone. Additional clinical findings indicated that diabetic neuropathy may occur in association with a latent prediabetic metabolic disturbance, and that the symptoms of neuropathy can be favourably influenced by the described combination therapy, even in poorly controlled diabetes. [7]


Today, many companies offer Vitamin B5 supplements aimed at reducing acne. The recommended treatment course, however, can be perceived as difficult and expensive. Many sites suggest starting off the first three days with 5g and then moving up to 10g a day for three months. Since the largest pill available is 1g, this can result in as many as 10 pills a day or more if smaller pills are taken. The average cost for a bottle of 200 B5 500mg tablets is $10, so the cost can be steep. B5 sold as a powder that can be dissolved in water and drunk is generally a cheaper and for some people a more convenient alternative. Furthermore, after three months many users suggest decreasing to 3-5g a day, with some claiming 1 g/day is sufficient.


Synonyms

  • Pantothenate
  • Vitamin B5
  • Vilantae — a brand name for the supplement when used to treat acne.

See also

Coenzyme A (CoA, CoASH, or HSCoA) is a coenzyme, notable for its role in the synthesis and oxidization of fatty acids, and the oxidation of pyruvate in the citric acid cycle. ... Panthenol is the alcohol analog of pantothenic acid (vitamin B5), and is thus the provitamin of B5. ...

Enzymes

  • Ketopantoate hydroxymethyltransferase

References

  1. ^ MedlinePlus. "Pantothenic acid (Vitamin-B5), Dexpanthenol". Natural Standard Research Collaboration. U.S. National Library of Medicine. Last accessed 4 Jan 2007. [1]
  2. ^ Kimura S, Furukawa Y, Wakasugi J, Ishihara Y, Nakayama A. Antagonism of L(-)pantothenic acid on lipid metabolism in animals. J Nutr Sci Vitaminol (Tokyo). 1980;26(2):113-7. PMID 7400861.
  3. ^ a b Jane Higdon, "Pantothenic Acid", Micronutrient Information Center, Linus Pauling Institute
  4. ^ Nutrient Data Products and Services, Nutrient Data : Reports by Single Nutrients. Retrieved on 2007-08-12.
  5. ^ Said H, Ortiz A, McCloud E, Dyer D, Moyer M, Rubin S (1998). "Biotin uptake by human colonic epithelial NCM460 cells: a carrier-mediated process shared with pantothenic acid.". Am J Physiol 275 (5 Pt 1): C1365-71. PMID 9814986. 
  6. ^ Leung L (1995). "Pantothenic acid deficiency as the pathogenesis of acne vulgaris". Med Hypotheses 44 (6): 490-2. PMID 7476595. 
  7. ^ Münchener Medizinische Wochenschrift (Germany), 1997, 139/12 (34-37)

Oregon State University (OSU) is a four-year research and degree-granting public university, located in Corvallis, Oregon in the United States. ... Year 2007 (MMVII) is the current year, a common year starting on Monday of the Gregorian calendar and the AD/CE era. ... is the 224th day of the year (225th in leap years) in the Gregorian calendar. ...

External links


  Results from FactBites:
 
Linus Pauling Institute at Oregon State University (1719 words)
Pantothenic acid is found throughout living cells in the form of coenzyme A (CoA), a vital coenzyme in numerous chemical reactions (2).
Pantothenic acid is a component of coenzyme A (CoA), an essential coenzyme in a variety of reactions that sustain life.
However, a specialized process for the uptake of biotin and pantothenic acid was recently identified in cultured cells derived from the lining of the colon, suggesting that humans may be able to absorb pantothenic acid and biotin produced by the bacteria normally present in the colon (13).
Pantothenic Acid: Encyclopedia of Alternative Medicine (1008 words)
Other claims for pantothenic acid that remain unproven are that it improves immune function, decreases allergies, and acts as an anti-aging substance.
Pantothenic acid is fairly heat-stable, and is not broken down by cooking although it is destroyed by extremes of pH as may be created by adding such things as baking soda or vinegar.
Experimentally induced deficiency of pantothenic acid has caused fatigue, somnolence, headache, hyperreflexia of extremities, tingling, numbness, or burning in hands and feet, weakness, gastrointestinal problems, irritability, and increased numbers of infections.
  More results at FactBites »

 
 

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