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Pantothenic acid

Pantothenic acid
Skeletal formula of (R)-pantothenic acid
Pantothenic acid molecule
Names
Preferred IUPAC name
3-[(2R)-2,4-Dihydroxy-3,3-dimethylbutanamido]propanoic acid
Systematic IUPAC name
3-[(2R)-(2,4-Dihydroxy-3,3-dimethylbutanoyl)amino]propanoic acid
Identifiers
599-54-2 N
79-83-4 (R) N
3D model (Jmol) Interactive image
(R): Interactive image
(S): Interactive image
3DMet B00193
1727062, 1727064 (R)
ChEBI CHEBI:7916 N
ChEMBL ChEMBL1594 YesY
ChemSpider 963 N
6361 (R) N
4677898 (S) N
DrugBank DB01783 YesY
ECHA InfoCard 100.009.061
EC Number 209-965-4
KEGG D07413 YesY
MeSH Pantothenic+Acid
PubChem 988
6613 (R)
5748353 (S)
RTECS number RU4729000
UNII 19F5HK2737 N
Properties
C9H17NO5
Molar mass 219.24 g·mol−1
Appearance Yellow oil
Colorless crystals (Ca2+ salt)
Odor Odorless
Density 1.266 g/cm3
1.32 g/cm3 (Ca2+ salt)
Melting point 183.83 °C (362.89 °F; 456.98 K)
196–200 °C (385–392 °F; 469–473 K)
decomposes (Ca2+ salt)
138 °C (280 °F; 411 K)
decomposes (Ca2+ salt, monohydrate)
Very soluble
2.11 g/mL (Ca2+ salt)
Solubility Very soluble in C6H6, ether
Ca2+ salt:
Slightly soluble in alcohol, CHCl3
log P −1.416
Acidity (pKa) 4.41
Basicity (pKb) 9.698
+37.5°
+24.3° (Ca2+ salt)
Hazards
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point 287.3 °C (549.1 °F; 560.5 K)
Lethal dose or concentration (LD, LC):
LD50 (median dose)
> 10 mg/g (Ca2+ salt)
Related compounds
Related alkanoic acids
Arginine
Hopantenic acid
4-(γ-Glutamylamino)butanoic acid
Related compounds
Panthenol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YesYN ?)
Infobox references

Pantothenic acid, also called vitamin B5 (a B vitamin), is a water-soluble vitamin. Pantothenic acid is an essential nutrient. Animals require pantothenic acid to synthesize coenzyme-A (CoA), as well as to synthesize and metabolize proteins, carbohydrates, and fats. The anion is called pantothenate.

Pantothenic acid is the amide 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. It is commonly found as its alcohol analog, the provitamin panthenol (pantothenol), and as calcium pantothenate.

Pantothenic acid was discovered by Roger J. Williams in 1933.

Only the dextrorotatory (D) isomer of pantothenic acid possesses biologic activity. The levorotatory (L) form may antagonize the effects of the dextrorotatory isomer.

Pantothenic acid is used in the synthesis of coenzyme A (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. CoA is important in energy metabolism for pyruvate to enter the tricarboxylic acid cycle (TCA cycle) as acetyl-CoA, and for α-ketoglutarate to be transformed to succinyl-CoA in the cycle. CoA is also important in the biosynthesis of many important compounds such as fatty acids, cholesterol, and acetylcholine. CoA is incidentally also required in the formation of ACP, which is also required for fatty acid synthesis in addition to CoA.


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