Olivetol
Chemical compound
From Wikipedia, the free encyclopedia
Olivetol is an organic compound with the formula C5H11C6H3(OH)2. Several isomers exist; olivetol has the two hydroxyl and the pentyl groups located at the 1,3, and 5 positions on the benzene ring. It is a colorless solid that is soluble in a variety of organic solvents. It is found in certain species of lichen. It is also a precursor in various syntheses of tetrahydrocannabinol.
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| Names | |
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| Preferred IUPAC name
5-Pentylbenzene-1,3-diol | |
| Other names
5-Pentyl-1,3-benzenediol; 5-Pentylresorcinol; 5-n-Amylresorcinol | |
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| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.007.190 |
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PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C11H16O2 | |
| Molar mass | 180.247 g·mol−1 |
| Appearance | colorless solid |
| Melting point | 40 to 41 °C (104 to 106 °F; 313 to 314 K) (49 to 49.5 °C) |
| Boiling point | 162 to 164 °C (324 to 327 °F; 435 to 437 K) at 5 mmHg; 192-195 °C at 11 mmHg |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Occurrence
Olivetol is found in certain species of lichens, from which it can be readily extracted.[1]
Olivetol is also produced by a number of insects, either as a pheromone, repellent, or antiseptic.[2][3]
The cannabis plant produces the related substance olivetolic acid (OLA), which may be involved in the biosynthesis of tetrahydrocannabinol (THC).[4][5]
Synthesis of THC analogs
Olivetol is used in various methods to produce synthetic analogs of THC. One such method is a condensation reaction of olivetol and geraniol in the presence of boron trifluoride, which affords a cannabigerol.[6]
In PiHKAL, Alexander Shulgin reports a cruder method of producing the same product by bringing to reaction olivetol and the essential oil of orange in the presence of phosphoryl chloride.[7]
A method for the synthesis of THC itself consists of the condensation reaction between olivetol and Δ2-carene oxide.[8]
Legality
The production, possession, and/or distribution of olivetol is not outlawed by any country; however, in the United States, it is a DEA watched precursor.[9][unreliable source?]
Biosynthesis
Olivetol is biosynthesized by a polyketide synthase (PKS)-type reaction from hexanoyl-CoA and three molecules of malonyl-CoA by an aldol condensation of a tetraketide intermediate. In 2009, Taura et al. was able to clone a type III PKS named olivetol synthase (OLS) from Cannabis sativa.[10] This PKS is a homodimeric protein that consists of a 385 amino acid polypeptide with a molecular mass of 42,585 Da that has high sequence similarity (60-70%) identity to plant PKSs.[10]
The data from Taura's study of OLS's enzyme kinetics show that OLS catalyzes a decarboxylative-aldol condensation to produce olivetol. This is similar to stilbene synthase's (STS) mechanism for converting p-coumaroyl-CoA and malonyl-CoA to resveratrol. Although olivetol is the decarboxylated form of OLA, it is highly unlikely that OLS produces olivetol from OLA.[10][11] Crude enzyme extracts prepared from flowers and leaves did not synthesize olivetolic acid, but only yielded olivetol.[10] The exact mechanism of olivetol biosynthesis is as yet unsure, but it is possible that an OLA-forming metabolic complex forms along with OLS.[10] In addition, it also appears that OLS only specifically accepts starter CoA esters with C4 to C8 aliphatic side chains such as hexanoyl-CoA.[10][12]
