5-Pentyl-1,3-benzenediol; 5-Pentylresorcinol; 5-n-Amylresorcinol
3D model (JSmol)
|Molar mass||g·mol−1 180.247|
|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).
|what is ?)(|
The cannabis plant internally produces the related substance olivetolic acid (OLA), which was hypothesized that the plant in turn utilizes to biosynthesize the psychoactive product tetrahydrocannabinol (THC).
Synthesis of productsEdit
One such method is a condensation reaction of olivetol and pulegone. 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. It can also be produced by reacting olivetol with α-pinene.
The production, possession and/or distribution of olivetol is not currently known to be outlawed by any country.
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. 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.
- 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). Johnson, Christopher James, ed. "Imbricaric Acid and Perlatolic Acid: Multi-Targeting Anti-Inflammatory Depsides from Cetrelia monachorum". PLoS ONE. 8 (10): e76929. doi:10.1371/journal.pone.0076929. PMC 3793931. 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[clarification needed]
- Shulgin, Alexander T (1991) PiHKAL: 26
- US 3734930, Razdan, Raj Kumar & Handrick, Richard G., "DIRECT SYNTHESIS OF (-)-TRANS-Δ TETRAHYDROCANNABINOL FROM OLIVETOL AND (+)-TRANS-Δ -CARENE OXIDE"
- 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.