Olivetolic acid

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Olivetolic acid
Olivetolic acid.svg
Names
Preferred IUPAC name
2,4-Dihydroxy-6-pentylbenzoic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
PubChem CID
UNII
  • 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
  • CCCCCC1=C(C(=CC(=C1)O)O)C(=O)O
Properties
C12H16O4
Molar mass 224.256 g·mol−1
Appearancecolorless 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 [77 °F], 100 kPa).

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 . [1]

The ester dimer of olivetolic acid, anziaic acid, is found in lichen. [2] [3]

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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