What is Olivetol CAS 500-66-3
Olivetol CAS 500-66-3, also known as 5-pentylresorcinol or 5-pentyl-1,3-benzenediol, is a naturally occurring organic compound found in certain species of lichen and can be readily extracted; it is also produced by a number of insects, either as a pheromone, repellent, or antiseptic. Olivetol is also a precursor in various syntheses of tetrahydrocannabinol.
Olivetol CAS 500-66-3 Details
|Other Names||1,3-Benzenediol, 5-pentyl-;5-pentylbenzene-1,3-diol;5-Pentyl-1,3-benzenediol;5-Pentylresorcinol;5-n-Amylresorcinol|
|Property||Appearance and properties: light brown powderDensity: 1.068 g / cm3Boiling point: 313.3ºCat 760 mmHgMelting point: 46-48ºC Flash point:> 110ºCRefractive index: 1.546|
|Stability||Stable at room temperature in closed containers under normal storage and handling conditions. May discolor on exposure to light.|
|Storage||Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. Refrigerator (approx 4ºC). Store protected from light.|
Olivetol CAS 500-66-3 Synthetic Route
1. 1,3-Dimethoxy-5-pentylbenzene → Olivetol
2. 2,4-Dihydroxy-6-pentylisophthalic acid dimethyl ester → Olivetol
3. 3,5-Dimethoxybenzoic Acid → Olivetol
Olivetol CAS 500-66-3 Downstream products
1. 5-pentylcyclohexane-1,3-dione CAS#18456-88-7
2. (-)-Cannabidiol CAS#13956-29-1
3. Abn-CBD,4-[(1R,6R)-3-Methyl-6-(1-methylethenyl)-2-cyclohexen-1-yl]-5-pentyl-1,3-benzenediol CAS#22972-55-0
4. Hexanoic acid CAS#142-62-1
5. 1,3-Dimethoxy-5-pentylbenzene CAS#22976-40-5
How to biosynthesize Olivetol CAS 500-66-3?
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. were 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.
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. Crude enzyme extracts prepared from flowers and leaves did not synthesize olivetolic acid, but only yielded olivetol. The exact mechanism of olivetol biosynthesis is as yet unsure, but it is possible that an OLA-forming metabolic complex forms along with OLS. In addition, it also appears that OLS only specifically accepts starter CoA esters with C4 to C8 aliphatic side chains such as hexanoyl-CoA.