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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03 Olivetol powder (500-66-3) video
04 Olivetol powder (500-66-3) Base Information
|Name||Olivetol (3,5-hydroxypentylbenzene) powder|
|Synonyms||3,5-Dihydroxyamylbenzene; 5-n-Amylresorcinol; 5-n-Pentylresorcinol; 1,3-Dihydroxy-5-pentylbenzene; 5-Pentyl-1,3-benzenediol;|
|Melting Point||46-48 °C(lit.)|
|Appearance||light purple to brown crystalline|
|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.|
05 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
06 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.
07 Olivetol powder (500-66-3) Mechanism Of Action
08 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.
09 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.
10 Olivetol powder (500-66-3) Document Download
11 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.
12 PRECAUTION AND DISCLAIMER:
PRECAUTION AND DISCLAIMER:
This Material is Sold For Research Use Only. Terms of Sale Apply. Not for Human Consumption, nor Medical, Veterinary, or Household Uses.
- 01. Overview
- 02. Contact Us
- 03. Olivetol powder (500-66-3) video
- 04. Olivetol powder (500-66-3) Base Information
- 05. Olivetol powder (500-66-3) General Description
- 06. Olivetol powder (500-66-3) History
- 07. Olivetol powder (500-66-3) Mechanism Of Action
- 08. Olivetol powder (500-66-3) Application
- 09. Olivetol powder (500-66-3) More research
- 10. Olivetol powder (500-66-3) Document Download
- 11. Olivetol powder (500-66-3) Reference
- 12. PRECAUTION AND DISCLAIMER: