Olivetol

Olivetol is an organic compound with the formula C₅H₁₁C₆H₃(OH)₂. Several isomers exist; olivetol has the two hydroxyl and the pentyl groups located at the 1,3, and 5 positions on the benzene ring. It is a colorless solid that is soluble in a variety of organic solvents. It is found in certain species of lichen. It is also a precursor in various syntheses of tetrahydrocannabinol.

Olivetol

Names
Preferred IUPAC name 5-Pentylbenzene-1,3-diol
Other names 5-Pentyl-1,3-benzenediol; 5-Pentylresorcinol; 5-n-Amylresorcinol
Identifiers
CAS Number	500-66-3 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:66960 N
ChemSpider	9949 N
ECHA InfoCard	100.007.190
EC Number	207-908-8
PubChem CID	10377
UNII	65OP0NEZ1P Y
CompTox Dashboard (EPA)	DTXSID0025812
InChI InChI=1S/C11H16O2/c1-2-3-4-5-9-6-10(12)8-11(13)7-9/h6-8,12-13H,2-5H2,1H3 N Key: IRMPFYJSHJGOPE-UHFFFAOYSA-N N InChI=1/C11H16O2/c1-2-3-4-5-9-6-10(12)8-11(13)7-9/h6-8,12-13H,2-5H2,1H3 Key: IRMPFYJSHJGOPE-UHFFFAOYAG
SMILES CCCCCC1=CC(=CC(=C1)O)O
Properties
Chemical formula	C11H16O2
Molar mass	180.247 g·mol−1
Appearance	colorless solid
Melting point	40 to 41 °C (104 to 106 °F; 313 to 314 K) (49 to 49.5 °C)
Boiling point	162 to 164 °C (324 to 327 °F; 435 to 437 K) at 5 mmHg; 192-195 °C at 11 mmHg
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Occurrence

Olivetol is found in certain species of lichens, from which it can be readily extracted.^[1]

Olivetol is also produced by a number of insects, either as a pheromone, repellent, or antiseptic.^[2][3]

The cannabis plant produces the related substance olivetolic acid (OLA), which may be involved in the biosynthesis of tetrahydrocannabinol (THC).^[4][5]

Synthesis of THC analogs

Olivetol is used in various methods to produce synthetic analogs of THC. One such method is a condensation reaction of olivetol and geraniol in the presence of boron trifluoride, which affords a cannabigerol.^[6]

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.^[7]

A method for the synthesis of THC itself consists of the condensation reaction between olivetol and Δ²-carene oxide.^[8]

Legality

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.^{[9][unreliable source?]}

Biosynthesis

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. was able to clone a type III PKS named olivetol synthase (OLS) from Cannabis sativa.^[10] 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 PKSs.^[10]

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.^[10][12]

Biosynthesis of olivetol