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3-Hydroxyoctanoic acid

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3-Hydroxyoctanoic acid
Names
Preferred IUPAC name 3-Hydroxyoctanoic acid
Other names 3-Hydroxycaprylic acid; β-Hydroxyoctanoic acid
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
MeSH C101940
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C8H16O3/c1-2-3-4-5-7(9)6-8(10)11/h7,9H,2-6H2,1H3,(H,10,11)Key: NDPLAKGOSZHTPH-UHFFFAOYSA-N
  • InChI=1/C8H16O3/c1-2-3-4-5-7(9)6-8(10)11/h7,9H,2-6H2,1H3,(H,10,11)Key: NDPLAKGOSZHTPH-UHFFFAOYAI
SMILES
  • CCCCCC(CC(=O)O)O
Properties
Chemical formula C8H16O3
Molar mass 160.213 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

3-Hydroxyoctanoic acid is a beta-hydroxy acid that is naturally produced in humans, other animals, and plants.

3-Hydroxyoctanoic acid is the primary endogenous agonist of hydroxycarboxylic acid receptor 3 (HCA3), a G protein-coupled receptor protein which is encoded by the human gene HCAR3. In plants, signalling chemical emitted by the orchid Cymbidium floribundum and recognized by Japanese honeybees (Apis cerana japonica).

References

  1. Offermanns, S; Colletti, S. L; Lovenberg, T. W; Semple, G; Wise, A; Ijzerman, A. P (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): 269–90. doi:10.1124/pr.110.003301. PMID 21454438.
  2. Offermanns, S.; Colletti, S. L.; IJzerman, A. P.; Lovenberg, T. W.; Semple, G.; Wise, A.; Waters, M. G.; CGTP Collaborators. "Hydroxycarboxylic acid receptors". IUPHAR/BPS Guide to Pharmacology. International Union of Basic and Clinical Pharmacology. Retrieved 13 July 2018.
  3. Sugahara, M; Izutsu, K; Nishimura, Y; Sakamoto, F (2013). "Oriental orchid (Cymbidium floribundum) attracts the Japanese honeybee (Apis cerana japonica) with a mixture of 3-hydroxyoctanoic acid and 10-hydroxy- (E)-2-decenoic acid". Zoological Science. 30 (2): 99–104. doi:10.2108/zsj.30.99. PMID 23387843. S2CID 45520680.


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