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 ; 79-83-4 (R) ;
3D model (JSmol)	Interactive image; (R): Interactive image; (S): Interactive image;
Beilstein Reference	1727062, 1727064 (R)
ChEBI	CHEBI:7916 ;
ChEMBL	ChEMBL1594 ;
ChemSpider	963 ; 6361 (R) ; 4677898 (S) ;
DrugBank	DB01783 ;
ECHA InfoCard	100.009.061
EC Number	209-965-4;
KEGG	D07413 ;
MeSH	Pantothenic+Acid
PubChem CID	988; 6613 (R); 5748353 (S);
RTECS number	RU4729000;
UNII	66Y94D1203 ; 19F5HK2737 (R) ;
CompTox Dashboard (EPA)	DTXSID7047229 ;
	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) Key: GHOKWGTUZJEAQD-UHFFFAOYSA-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	219.237 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	183.833 °C (362.899 °F; 456.983 K) ; 196–200 °C (385–392 °F; 469–473 K); decomposes (Ca2+ salt)
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 (fire diamond)	2 1 0
	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). verify (what is ?) Infobox references

Pantothenic acid (vitamin B₅) is a B vitamin and an essential nutrient. All animals need pantothenic acid in order to synthesize coenzyme A (CoA), which is essential for cellular energy production and for the synthesis and degradation of proteins, carbohydrates, and fats.

Pantothenic acid is the combination of pantoic acid and β-alanine. Its name comes from the Greek πάντοθεν pantothen, meaning "from everywhere", because pantothenic acid, at least in small amounts, is in almost all foods. Deficiency of pantothenic acid is very rare in humans. In dietary supplements and animal feed, the form commonly used is calcium pantothenate, because chemically it is more stable, and hence makes for longer product shelf-life, than sodium pantothenate and free pantothenic acid.