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 | |
| Jmol-3D images | Image 1 | |
| ||
| Properties | ||
| Molecular formula | C11H16O2 | |
| Molar mass | 180.24 g mol−1 | |
| Melting point | 40-41°C; 49-49.5°C | |
| Boiling point | 162-164°C @ 5 mm; 192-195°C @ 11 mm | |
(verify) (what is: / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 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.[1]
5-Pentylresorcinol is also produced by a number of insects, either as a pheromone, repellent or antiseptic.[2][3]
The cannabis plant also internally produces the related substance olivetolic acid, which it in turn is used to biosynthesize the psychoactive product tetrahydrocannabinol (THC).[4][5]
Synthesis of products
This compound has been documented as being a usable ingredient in various methods of condensation reactions, which can produce a synthetic form of THC.[6]
One such method is a condensation reaction of olivetol and pulegone.[7] 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.[7] It can also be produced by reacting olivetol with α-pinene.
Another method for the stereospecific synthesis of Δ9-tetrahydrocannabinol comprising condensing olivetol with 2-carene oxide.[8]
Legality
The production, possession and/or distribution of olivetol is not currently known to be outlawed by any country.
Biosynthesis
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.[9] 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.[9]
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 olivetolic acid (OLA), it is highly unlikely that OLS produces olivetol from OLA.[9][10] Crude enzyme extracts prepared from flowers and leaves did not synthesize olivetolic acid, but only yielded olivetol.[9] The exact mechanism of olivetol biosynthesis is as yet unsure, but it is possible that an OLA-forming metabolic complex forms along with OLS.[9] In addition, it also appears that OLS only specifically accepts starter CoA esters with C4 to C8 aliphatic side chains such as hexanoyl-CoA.[9][11]
References
- ↑ Oettl, Sarah K.; Gerstmeier, Jana; Khan, Shafaat Y.; Wiechmann, Katja; Bauer, Julia; Atanasov, Atanas G.; Malainer, Clemens; Awad, Ezzat M.; Uhrin, Pavel; Heiss, Elke H.; Waltenberger, Birgit; Remias, Daniel; Breuss, Johannes M.; Boustie, Joel; Dirsch, Verena M.; Stuppner, Hermann; Werz, Oliver; Rollinger, Judith M. (2013). "Imbricaric Acid and Perlatolic Acid: Multi-Targeting Anti-Inflammatory Depsides from Cetrelia monachorum". In Johnson, Christopher James. PLoS ONE 8 (10): e76929. doi:10.1371/journal.pone.0076929. PMID 24130812.
- ↑ Attygalle et al. (1989). Journal of Chemical Ecology. (15) 1: 317-28 ISSN: 0098-0331/89/0100-0317506.00/0
- ↑ The Pherobase (Database pf pheromones and semiochemicals). 5-Pentylresorcinol]. Retrieved 18 January 2014
- ↑ Hassuni, I; Razxouk, H (2005). "Olivetol: Constituent of lichen Evernia prunastri Ach. or "oakmoss"". Physical and Chemical News 26: 98–103.
- ↑ Stojanovic, Igor; Radulovic, Niko; Mitrovic, Tatjana; Stamenkovic, Slavisa; Stojanovic, Gordana (2011). "Volatile constituents of selected Parmeliaceae lichens". Journal of the Serbian Chemical Society 76 (7): 987–94. doi:10.2298/JSC101004087S.
- ↑ Adams, Roger University of Illinois
- ↑ 7.0 7.1 Shulgin, Alexander T (1991) PiHKAL
- ↑ US 3734930, Razdan, Raj Kumar & Handrick, Richard G., "DIRECT SYNTHESIS OF (-)-TRANS-Δ TETRAHYDROCANNABINOL FROM OLIVETOL AND (+)-TRANS-Δ -CARENE OXIDE"
- ↑ 9.0 9.1 9.2 9.3 9.4 9.5 Taura, Futoshi; Tanaka, Shinji; Taguchi, Chiho; Fukamizu, Tomohide; Tanaka, Hiroyuki; Shoyama, Yukihiro; Morimoto, Satoshi (2009). "Characterization of olivetol synthase, a polyketide synthase putatively involved in cannabinoid biosynthetic pathway". FEBS Letters 583 (12): 2061–6. doi:10.1016/j.febslet.2009.05.024. PMID 19454282.
- ↑ Raharjo, Tri J; Chang, Wen-Te; Choi, Young Hae; Peltenburg-Looman, Anja M.G; Verpoorte, Robert (2004). "Olivetol as product of a polyketide synthase in Cannabis sativa L". Plant Science 166 (2): 381–5. doi:10.1016/j.plantsci.2003.09.027.
- ↑ Raharjo, Tri J.; Chang, Wen-Te; Verberne, Marianne C.; Peltenburg-Looman, Anja M.G.; Linthorst, Huub J.M.; Verpoorte, Robert (2004). "Cloning and over-expression of a cDNA encoding a polyketide synthase from Cannabis sativa". Plant Physiology and Biochemistry 42 (4): 291–7. doi:10.1016/j.plaphy.2004.02.011. PMID 15120113.