Olivetol

Olivetol
IUPAC name 5-Pentyl-1,3-benzenediol
Other names 5-Pentylresorcinol; 5-n-Amylresorcinol
Identifiers
CAS number	500-66-3
PubChem	10377
UNII	65OP0NEZ1P Y
Jmol-3D images	Image 1
SMILES CCCCCC1=CC(=CC(=C1)O)O
Properties
Molecular formula	C11H16O2
Molar mass	180.24 g mol−1
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Olivetol, also known as 5-pentylresorcinol or 5-pentyl-1,3-benzenediol, is an organic compound found in certain species of lichen; it is also a precursor in various syntheses of tetrahydrocannabinol.

Occurrence

Olivetol is a naturally occurring organic compound. It is found in certain species of lichens and can be readily extracted.

The cannabis plant also internally produces the related substance olivetolic acid, which it in turn uses to biosynthesize the psychoactive product tetrahydrocannabinol (THC).^[1]

^[2]

Synthesis of Products

This compound has been documented ^[3] as being a usable ingredient in various methods of condensation reactions, which can produce a synthetic form of THC.

One such method is a condensation reaction of olivetol and pulegone^[4] as mentioned in the book PiHKAL by Alexander Shulgin. In PiHKAL, Shulgin also notes a cruder method of producing the same product by bringing to reaction olivetol and the essential oil obtained from orange peel in the presence of phosphoryl chloride.^[4] It can also be produced by reacting olivetol with a-pinene.

Another method for the stereospecific synthesis of Δ⁹-tetrahydrocannabinol comprising condensing olivetol with ²-carene oxide.^[5]

Legality

The production, possession and/or distribution of olivetol is not currently known to be outlawed by any country.

References

1. ^ Hassuni I, Razxouk H. (2005). "Olivetol: Constituent of lichen Evernia prunastri Ach. or "oakmoss"". Physical and Chemical News 26: 98–103. 
2. ^ Volatile constituents of selected Parmeliaceae lichens Author: IGOR Ž. STOJANOVIĆ ; NIKO S. RADULOVIĆ ; TATJANA LJ. MITROVIĆ ; SLAVIŠA M. STAMENKOVIĆ ; GORDANA S. STOJANOVIĆ
3. ^ Adams, Roger University of Illinois^{[clarification needed]}
4. ^ ^{a b} Shulgin, Alexander T (1991) PiHKAL
5. ^ Razdan, Raj Kumar & Handrick, Richard G. DIRECT SYNTHESIS OF (-)-TRANS-Δ TETRAHYDROCANNABINOL FROM OLIVETOL AND (+)-TRANS-Δ -CARENE OXIDE, US Patent 3734930