2-Hydroxybutyric acid

2-Hydroxybutyric acid
Names
	IUPAC name 2-Hydroxybutanoic acid
	Other names alpha-hydroxybutyrate
Identifiers
CAS Number	565-70-8 ;
3D model (JSmol)	Interactive image; Interactive image;
ChEBI	CHEBI:1148 ;
ChEMBL	ChEMBL567588 ;
ChemSpider	10792 ;
ECHA InfoCard	100.009.079
MeSH	2-hydroxybutyric+acid
PubChem CID	11266;
CompTox Dashboard (EPA)	DTXSID8041903 ;
	InChI InChI=1S/C4H8O3/c1-2-3(5)4(6)7/h3,5H,2H2,1H3,(H,6,7) Key: AFENDNXGAFYKQO-UHFFFAOYSA-N ; InChI=1/C4H8O3/c1-2-3(5)4(6)7/h3,5H,2H2,1H3,(H,6,7) Key: AFENDNXGAFYKQO-UHFFFAOYAH;
	SMILES CCC(O)C(=O)O; O=C(O)C(O)CC;
Properties
Chemical formula	C4H8O3
Molar mass	104.105 g·mol−1
Related compounds
Other anions	hydroxybutyrate
Related carboxylic acids	propionic acid; lactic acid; 3-hydroxypropionic acid; malonic acid; butyric acid; hydroxypentanoic 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).
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	Infobox references

2-Hydroxybutyric acid, also known as alpha-hydroxybutyrate and α-hydroxybutyrate, is a hydroxybutyric acid with the hydroxyl group on the carbon adjacent to the carboxyl. It is a chiral compound having two enantiomers, D-2-hydroxybutyric acid and L-2-hydroxybutyric acid.

(R)-2-hydroxybutyric acid
(S)-2-hydroxybutyric acid

2-Hydroxybutyrate, the conjugate base of 2-hydroxybutyric acid, is produced in mammalian tissues (principally hepatic) that catabolize L-threonine or synthesize glutathione. Oxidative stress or detoxification demands can dramatically increase the rate of hepatic glutathione synthesis. Under such metabolic stress conditions, supplies of L-cysteine for glutathione synthesis become limiting, so homocysteine is diverted from the transmethylation pathway forming methionine into the transsulfuration pathway forming cystathionine. 2-Hydroxybutyrate is released as a byproduct when cystathionine is cleaved to cysteine that is incorporated into glutathione. Chronic shifts in the rate of glutathione synthesis may be reflected by urinary excretion of 2-hydroxybutyrate.

α-hydroxybutyrate may be useful as an early indicator of insulin resistance in non-diabetic subjects.[1] Moreover, elevated serum α-hydroxybutyrate predicts worsening glucose tolerance.[2]

References

Gall WE, Beebe K, Lawton KA, Adam KP, Mitchell MW, Nakhle PJ, Ryals JA, Milburn MV, Nannipieri M, Camastra S, Natali A, Ferrannini E, RISC Study Group (2010). "alpha-hydroxybutyrate is an early biomarker of insulin resistance and glucose intolerance in a nondiabetic population". PLOS ONE. 5 (5): 10883. doi:10.1371/journal.pone.0010883. PMC 2878333. PMID 20526369.
Ferrannini E, Natali A, Camastra S, Nannipieri M, Mari A, Adam KP, Milburn MV, Kastenmüller G, Adamski J, Tuomi T, Lyssenko V, Groop L, Gall WE (2013). "Early metabolic markers of the development of dysglycemia and type 2 diabetes and their physiological significance". Diabetes. 62 (5): 1730–1737. doi:10.2337/db12-0707. PMC 3636608. PMID 23160532.

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[pmid20526369-1] Gall WE, Beebe K, Lawton KA, Adam KP, Mitchell MW, Nakhle PJ, Ryals JA, Milburn MV, Nannipieri M, Camastra S, Natali A, Ferrannini E, RISC Study Group (2010). "alpha-hydroxybutyrate is an early biomarker of insulin resistance and glucose intolerance in a nondiabetic population". PLOS ONE. 5 (5): 10883. doi:10.1371/journal.pone.0010883. PMC 2878333. PMID 20526369.

[pmid23160532-2] Ferrannini E, Natali A, Camastra S, Nannipieri M, Mari A, Adam KP, Milburn MV, Kastenmüller G, Adamski J, Tuomi T, Lyssenko V, Groop L, Gall WE (2013). "Early metabolic markers of the development of dysglycemia and type 2 diabetes and their physiological significance". Diabetes. 62 (5): 1730–1737. doi:10.2337/db12-0707. PMC 3636608. PMID 23160532.