3-Hydroxyoctanoic acid

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

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
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−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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.[1][2] In plants, signalling chemical emitted by the orchid Cymbidium floribundum and recognized by Japanese honeybees (Apis cerana japonica).[3]

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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