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Olivetol (3,5-hydroxypentylbenzene) powder (500-66-3)

Olivetol powder (500-66-3)

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).

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Olivetol powder (500-66-3) video

 

 

Olivetol powder (500-66-3) Base Information

Name Olivetol (3,5-hydroxypentylbenzene) powder
CAS 500-66-3
Purity 98%
Chemical name Olivetol
Synonyms 3,5-Dihydroxyamylbenzene; 5-n-Amylresorcinol; 5-n-Pentylresorcinol; 1,3-Dihydroxy-5-pentylbenzene; 5-Pentyl-1,3-benzenediol;
Molecular Formula C11H16O2
Molecular Weight 180.2435
Melting Point 46-48 °C(lit.)
InChI Key IRMPFYJSHJGOPE-UHFFFAOYSA-N
Form solid
Appearance light purple to brown crystalline
Half Life /
Solubility Soluble in water (partly miscible), chloroform, and methanol.
Storage Condition In a dry and ventilated warehouse; keep away from sunshine; avoid fire; avoid moisture.
Application 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.
Testing Document Available

 

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.

 

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