Olivetol
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IUPAC name
5-Pentyl-1,3-benzenediol
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| Other names
5-Pentylresorcinol; 5-n-Amylresorcinol
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3D model (Jmol)
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| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.007.190 |
| EC Number | 207-908-8 |
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PubChem CID
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| Properties | |
| C11H16O2 | |
| Molar mass | 180.25 g·mol−1 |
| 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 |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 (what is   ?) |
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| Infobox references | |
Olivetol, also known as 5-pentylresorcinol or 5-pentyl-1,3-benzenediol, is an organic compound found in certain species of lichen; it is also a precursor in various syntheses of tetrahydrocannabinol.
Olivetol is a naturally occurring organic compound. It is found in certain species of lichens and can be readily extracted.
5-Pentylresorcinol is also produced by a number of insects, either as a pheromone, repellent or antiseptic.
The cannabis plant internally produces the related substance olivetolic acid (OLA), which was hypothesized that the plant in turn utilizes to biosynthesize the psychoactive product tetrahydrocannabinol (THC).
This compound has been documented as being a usable ingredient in various methods of condensation reactions, which can produce a synthetic form of THC.
One such method is a condensation reaction of olivetol and pulegone. In PiHKAL, Shulgin also notes a cruder method of producing the same product by bringing to reaction olivetol and the essential oil obtained from orange peel in the presence of phosphoryl chloride. It can also be produced by reacting olivetol with α-pinene.
Another method for the stereospecific synthesis of Δ9-tetrahydrocannabinol comprising condensing olivetol with 2-carene oxide.
The production, possession and/or distribution of olivetol is not currently known to be outlawed by any country.
Olivetol is biosynthesized by a polyketide synthase-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. 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 PKS's.
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Wikipedia