Chemistry:Olivetolic acid
From HandWiki
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| Preferred IUPAC name
2,4-Dihydroxy-6-pentylbenzoic acid | |
| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
PubChem CID
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| Properties | |
| C12H16O4 | |
| Molar mass | 224.256 g·mol−1 |
| Appearance | colorless solid |
| Melting point | 148–9 °C (298–48 °F; 421–282 K) |
| Related compounds | |
Related compounds
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Cannabidiolic acid |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Tracking categories (test):
Olivetolic acid is an organic compound with the formula C
5H
11C
6H
2(OH)
2CO
2H. Several isomers with this formula exist. Olivetolic acid can be viewed as a derivative of olivetol ( 1,3,5-C
5H
11C
6H
2(OH)
2CO
2H, 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
- ↑ 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.
- ↑ 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). doi:10.1371/journal.pone.0060770. PMID 23593306. Bibcode: 2013PLoSO...860770C.
- ↑ 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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