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).
Soluble in water (partly miscible), chloroform, and methanol.
In a dry and ventilated warehouse; keep away from sunshine; avoid fire; avoid moisture.
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.
Olivetol powder (500-66-3) General Description
Olivetol was used as a template molecule in the synthesis of molecularly imprinted polymer (MIP). It was also used as an inhibitor of (S)-mephenytoin 4′-hydroxylase activity of recombinant CYP2C19.
Olivetol is used in various methods to produce synthetic analogs of THC.full citation needed] One such method is a condensation reaction of olivetol and pulegone. 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.
A method for the synthesis of THC itself consists of the condensation reaction between olivetol and Δ2-carene oxide
Olivetol powder (500-66-3) History
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.
Olivetol powder (500-66-3) Application
1, Used as pharmaceutical industry.
2, Used as Organic Intermediate.
3, Used as the determination of lipopolysaccharides, carrageenan and sialic acid.
Olivetol powder (500-66-3) More research
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.
Olivetol powder (500-66-3) Reference
Kumano, T., et al.: Bioorg. Med. Chem., 16, 8117 (2008), Appendino, G., et al.: J. Nat. Prod., 71, 1427 (2008), Sampietro, D., et al.: Food Chem., 115, 1170 (2009),
. Jiang R, et al. Cannabidiol is a potent inhibitor of the catalytic activity of cytochrome P450 2C19. Drug Metab Pharmacokinet. 2013;28(4):332-8.
. Yamaori S, et al. Cannabidiol, a major phytocannabinoid, as a potent atypical inhibitor for CYP2D6. Drug Metab Dispos. 2011 Nov;39(11):2049-56.