2-Hydroxybutyric acid

2-Hydroxybutyric acid, 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. Its conjugate base is known as alpha-hydroxybutyrate and α-hydroxybutyrate.

  • Molecular diagram of 2-hydroxybutyric acid, with the central alcohol carbon labeled "(R)"
    d-2-hydroxybutyric acid
  • Molecular diagram of 2-hydroxybutyric acid, with the central alcohol carbon labeled "(S)"
    l-2-hydroxybutyric acid
2-Hydroxybutyric acid
2-Hydroxybutyric acid molecule
Names
Preferred IUPAC name
2-Hydroxybutanoic acid
Other names
α-Hydroxybutyric acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.009.079
KEGG
MeSH 2-hydroxybutyric+acid
UNII
  • InChI=1S/C4H8O3/c1-2-3(5)4(6)7/h3,5H,2H2,1H3,(H,6,7) checkY
    Key: AFENDNXGAFYKQO-UHFFFAOYSA-N checkY
  • InChI=1/C4H8O3/c1-2-3(5)4(6)7/h3,5H,2H2,1H3,(H,6,7)
    Key: AFENDNXGAFYKQO-UHFFFAOYAH
  • CCC(O)C(=O)O
  • O=C(O)C(O)CC
Properties
C4H8O3
Molar mass 104.105 g·mol−1
Related compounds
Other anions
 hydroxybutyrate
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).
☒N verify (what is checkY☒N ?)
Infobox references

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
  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. Bibcode:2010PLoSO...510883G. doi:10.1371/journal.pone.0010883. PMC 2878333. PMID 20526369.
  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.
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