1.0 2020-03-19 00:46:23 UTC 2020-12-07 19:07:34 UTC CDB000607 Fenchyl alcohol Fenchyl alcohol, also known as fenchol, belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings. Fenchol or 1,3,3-trimethyl-2-norbornanol is a monoterpenoid and an isomer of borneol. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-eritritol-phosphate (MEP) pathway in the plastids. Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. It is a colorless or white solid. It occurs widely in nature. The naturally occurring enantiopure (1R)-endo-(+)-fenchol is used extensively in perfumery. Fenchol gives basil its characteristic scent (DOI: https://doi.org/10.1515/znc-2007-7-808) and comprises 15.9% of the volatile oils of some species of Aster (https://doi.org/10.1016/j.foodchem.2006.03.021). Fenchyl alcohol has also been detected as a volatile component in cannabis plant samples ( PMID: 6991645, 26657499). 1,3,3-Trimethyl-2-norbornanol endo-Fenchol Fenchol Fenchol, ((endo)-(+-))-isomer Fenchol, ((exo)-(+-))-isomer Fenchol, (1R-endo)-isomer Fenchol, (1S-endo)-isomer Fenchol, (1S-exo)-isomer Fenchol, (endo)-isomer Fenchol, (exo)-isomer Fenchyl alcohol C10H18O 154.25 154.1358 (1R,2R,4S)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-ol (1R,2R,4S)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-ol 2217-02-9 CC1(C)[C@H]2CC[C@](C)(C2)[C@H]1O InChI=1S/C10H18O/c1-9(2)7-4-5-10(3,6-7)8(9)11/h7-8,11H,4-6H2,1-3H3/t7-,8-,10+/m0/s1 IAIHUHQCLTYTSF-OYNCUSHFSA-N belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Bicyclic monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aliphatic homopolycyclic compounds Cyclic alcohols and derivatives Hydrocarbon derivatives Secondary alcohols Alcohol Aliphatic homopolycyclic compound Bicyclic monoterpenoid Cyclic alcohol Fenchane monoterpenoid Hydrocarbon derivative Organic oxygen compound Organooxygen compound Secondary alcohol melting_point 39 to 45 °C Wikipedia boiling_point 201 °C Wikipedia logp 2.30 ALOGPS logs -2.25 ALOGPS logp 2.15 ChemAxon pka_strongest_basic -0.52 ChemAxon iupac (1R,2R,4S)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-ol ChemAxon average_mass 154.25 ChemAxon mono_mass 154.1358 ChemAxon smiles CC1(C)[C@H]2CC[C@](C)(C2)[C@H]1O ChemAxon formula C10H18O ChemAxon inchi InChI=1S/C10H18O/c1-9(2)7-4-5-10(3,6-7)8(9)11/h7-8,11H,4-6H2,1-3H3/t7-,8-,10+/m0/s1 ChemAxon inchikey IAIHUHQCLTYTSF-OYNCUSHFSA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 45.16 ChemAxon polarizability 18.51 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 6997371 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499