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
| Product Name | Olivetol |
| Other Names | 1,3-Benzenediol, 5-pentyl-;5-pentylbenzene-1,3-diol;5-Pentyl-1,3-benzenediol;5-Pentylresorcinol;5-n-Amylresorcinol |
| CAS NO. | 500-66-3 |
| Purity | 98% min |
| Molecular Formula | C11H16O2 |
| Molecular Weight | 180.244 |
| 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.[10][11] Crude enzyme extracts prepared from flowers and leaves did not synthesize olivetolic acid, but only yielded olivetol.[10] The exact mechanism of olivetol biosynthesis is as yet unsure, but it is possible that an OLA-forming metabolic complex forms along with OLS.[10] In addition, it also appears that OLS only specifically accepts starter CoA esters with C4 to C8 aliphatic side chains such as hexanoyl-CoA.