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Olivetolic acid

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Olivetolic acid
Names
Preferred IUPAC name 2,4-Dihydroxy-6-pentylbenzoic acid
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C12H16O4/c1-2-3-4-5-8-6-9(13)7-10(14)11(8)12(15)16/h6-7,13-14H,2-5H2,1H3,(H,15,16)Key: SXFKFRRXJUJGSS-UHFFFAOYSA-N
SMILES
  • CCCCCC1=C(C(=CC(=C1)O)O)C(=O)O
Properties
Chemical formula C12H16O4
Molar mass 224.256 g·mol
Appearance colorless solid
Melting point 148–9 °C (298–48 °F; 421–282 K)
Related compounds
Related compounds Cannabidiolic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Olivetolic acid is an organic compound with the formula C5H11C6H2(OH)2CO2H. Several isomers with this formula exist. Olivetolic acid can be viewed as a derivative of olivetol ( 1,3,5-C5H11C6H2(OH)2CO2H, with a carboxylic acid group adjacent to the pentyl (C5H11) group. Olivetolic acid has attracted attention because it is an intermediate in the biosynthetic pathway of the cannabinoids, found in Cannabis sativa.

The ester dimer of olivetolic acid, anziaic acid, is found in lichen.

References

  1. Fellermeier, Monika; Zenk, Meinhart H (May 1998). "Prenylation of olivetolate by a hemp transferase yields cannabigerolic acid, the precursor of tetrahydrocannabinol". FEBS Letters. 427 (2): 283–285. doi:10.1016/S0014-5793(98)00450-5. PMID 9607329.
  2. Cheng, Bokun; Cao, Shugeng; Vasquez, Victor; Annamalai, Thirunavukkarasu; Tamayo-Castillo, Giselle; Clardy, Jon; Tse-Dinh, Yuk-Ching (8 April 2013). "Identification of Anziaic Acid, a Lichen Depside from Hypotrachyna sp., as a New Topoisomerase Poison Inhibitor". PLOS ONE. 8 (4): e60770. Bibcode:2013PLoSO...860770C. doi:10.1371/journal.pone.0060770. PMC 3620467. PMID 23593306.
  3. M.P. Polovinka; N.I. Komarova; D.V. Korchagina; D.N. Sokolov; O.A. Luzina; N.G. Vlasenko; A.A. Malyuga; E.V. Romanova; N.F. Salakhutdinov: Secondary metabolites of the lichen Cladonia stellaris in Chemistry of Natural Compounds 48 (2012) 392–395, doi:10.1007/s10600-012-0259-4.
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