β-Hydroxybutyric acid

β-Hydroxybutyric acid
Names
	Preferred IUPAC name 3-Hydroxybutanoic acid
Identifiers
CAS Number	300-85-6 ;
3D model (JSmol)	Interactive image; Interactive image;
Beilstein Reference	773861
ChEBI	CHEBI:20067 ;
ChEMBL	ChEMBL1162496 ;
ChemSpider	428 ;
ECHA InfoCard	100.005.546
IUPHAR/BPS	1593;
KEGG	C01089;
MeSH	beta-Hydroxybutyrate
PubChem CID	441;
UNII	TZP1275679 ;
CompTox Dashboard (EPA)	DTXSID60859511 ;
	InChI InChI=1S/C4H8O3/c1-3(5)2-4(6)7/h3,5H,2H2,1H3,(H,6,7) Key: WHBMMWSBFZVSSR-UHFFFAOYSA-N ; InChI=1/C4H8O3/c1-3(5)2-4(6)7/h3,5H,2H2,1H3,(H,6,7) Key: WHBMMWSBFZVSSR-UHFFFAOYAO;
	SMILES O=C(O)CC(O)C; CC(CC(=O)O)O;
Properties
Chemical formula	C4H8O3
Molar mass	104.105 g·mol−1
Appearance	white solid
Melting point	44-46
Related compounds
Other anions	hydroxybutyrate
Related carboxylic acids	propionic acid; lactic acid; 3-hydroxypropanoic acid; malonic acid; β-hydroxyvaleric acid; butyric acid; β-methylbutyric acid; β-hydroxy β-methylbutyric acid; crotonic acid
Related compounds	erythrose; threose; 1,2-butanediol; 1,3-butanediol; 2,3-butanediol; 1,4-butanediol
	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

β-Hydroxybutyric acid, also known as 3-hydroxybutyric acid or BHB, is an organic compound and a beta hydroxy acid with the chemical formula CH₃CH(OH)CH₂CO₂H; its conjugate base is β-hydroxybutyrate, also known as 3-hydroxybutyrate. β-Hydroxybutyric acid is a chiral compound with two enantiomers: D-β-hydroxybutyric acid and L-β-hydroxybutyric acid. Its oxidized and polymeric derivatives occur widely in nature. In humans, D-β-hydroxybutyric acid is one of two primary endogenous agonists of hydroxycarboxylic acid receptor 2 (HCA₂), a G_i/o-coupled G protein-coupled receptor (GPCR).^[1]^[2]

^ Offermanns S, Colletti SL, Lovenberg TW, Semple G, Wise A, IJzerman AP (June 2011). "International Union of Basic and Clinical Pharmacology. LXXXII: Nomenclature and Classification of Hydroxy-carboxylic Acid Receptors (GPR81, GPR109A, and GPR109B)". Pharmacological Reviews. 63 (2): 269–290. doi:10.1124/pr.110.003301. PMID 21454438.
^ Offermanns S, Colletti SL, IJzerman AP, Lovenberg TW, Semple G, Wise A, Waters MG. "Hydroxycarboxylic acid receptors". IUPHAR/BPS Guide to Pharmacology. International Union of Basic and Clinical Pharmacology. Retrieved 13 July 2018.

[IUPHAR's_comprehensive_2011_review_on_HCARs-1] Offermanns S, Colletti SL, Lovenberg TW, Semple G, Wise A, IJzerman AP (June 2011). "International Union of Basic and Clinical Pharmacology. LXXXII: Nomenclature and Classification of Hydroxy-carboxylic Acid Receptors (GPR81, GPR109A, and GPR109B)". Pharmacological Reviews. 63 (2): 269–290. doi:10.1124/pr.110.003301. PMID 21454438.

[IUPHAR-DB_HCAR_family_page-2] Offermanns S, Colletti SL, IJzerman AP, Lovenberg TW, Semple G, Wise A, Waters MG. "Hydroxycarboxylic acid receptors". IUPHAR/BPS Guide to Pharmacology. International Union of Basic and Clinical Pharmacology. Retrieved 13 July 2018.

[1]

[2]