Pantothenic acid

Pantothenic acid

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
CAS Number	599-54-2 N 79-83-4 (R) N
3D model (Jmol)	Interactive image (R): Interactive image (S): Interactive image
3DMet	B00193
Beilstein Reference	1727062, 1727064 (R)
ChEBI	CHEBI:7916 N
ChEMBL	ChEMBL1594 Y
ChemSpider	963 N 6361 (R) N 4677898 (S) N
DrugBank	DB01783 Y
ECHA InfoCard	100.009.061
EC Number	209-965-4
KEGG	D07413 Y
MeSH	Pantothenic+Acid
PubChem	988 6613 (R) 5748353 (S)
RTECS number	RU4729000
UNII	19F5HK2737 N
InChI InChI=1S/C9H17NO5/c1-9(2,5-11)7(14)8(15)10-4-3-6(12)13/h7,11,14H,3-5H2,1-2H3,(H,10,15)(H,12,13) N Key: GHOKWGTUZJEAQD-UHFFFAOYSA-N N
SMILES CC(C)(CO)C(C(=O)NCCC(=O)O)O (R): CC(C)(CO)[C@H](C(=O)NCCC(=O)O)O (S): CC(C)(CO)[C@@H](C(=O)NCCC(=O)O)O
Properties
Chemical formula	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)
Solubility in water	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
Chiral rotation ([α]D)	+37.5° +24.3° (Ca2+ salt)
Hazards
NFPA 704	1 2 0
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 YN ?)
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.