1.0 2020-03-18 23:25:27 UTC 2020-11-18 16:34:47 UTC CDB000118 beta-Curcumene Beta-curcumene belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA; PMID:17467679), in the cytosol. However, in plants, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP) pathway in the cytoplasm (PMID:23746261). Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Beta-curcumene is possibly neutral. Beta-curcumene has been detected in several plant species, as well as in Cannabis sativa (PMID: 6991645). It occurs in java ginger, turmeric, cedrala wood oil and sandal wood oil ( http://www.thegoodscentscompany.com/data/rw1701351.html#tooccur ). beta-Curcumene b-Curcumene Β-curcumene (-)-b-Curcumene (-)-Β-curcumene C15H24 204.36 204.1878 1-methyl-4-[(2R)-6-methylhept-5-en-2-yl]cyclohexa-1,4-diene (-)-β-curcumene C[C@H](CCC=C(C)C)C1=CCC(C)=CC1 InChI=1S/C15H24/c1-12(2)6-5-7-14(4)15-10-8-13(3)9-11-15/h6,8,11,14H,5,7,9-10H2,1-4H3/t14-/m1/s1 JXZQZARENYGJMK-CQSZACIVSA-N belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Sesquiterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids Aliphatic homomonocyclic compounds Branched unsaturated hydrocarbons Cyclic olefins Unsaturated aliphatic hydrocarbons Aliphatic homomonocyclic compound Bisabolane sesquiterpenoid Branched unsaturated hydrocarbon Cyclic olefin Hydrocarbon Olefin Sesquiterpenoid Unsaturated aliphatic hydrocarbon Unsaturated hydrocarbon beta-curcumene logp 6.03 ALOGPS logs -3.92 ALOGPS logp 4.82 ChemAxon iupac 1-methyl-4-[(2R)-6-methylhept-5-en-2-yl]cyclohexa-1,4-diene ChemAxon average_mass 204.36 ChemAxon mono_mass 204.1878 ChemAxon smiles C[C@H](CCC=C(C)C)C1=CCC(C)=CC1 ChemAxon formula C15H24 ChemAxon inchi InChI=1S/C15H24/c1-12(2)6-5-7-14(4)15-10-8-13(3)9-11-15/h6,8,11,14H,5,7,9-10H2,1-4H3/t14-/m1/s1 ChemAxon inchikey JXZQZARENYGJMK-CQSZACIVSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 71.36 ChemAxon polarizability 26.47 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 26332858 14014430 62760 CPD-11392 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 Buhaescu I, Izzedine H: Mevalonate pathway: a review of clinical and therapeutical implications. Clin Biochem. 2007 Jun;40(9-10):575-84. doi: 10.1016/j.clinbiochem.2007.03.016. Epub 2007 Mar 31. 17467679 Zhao L, Chang WC, Xiao Y, Liu HW, Liu P: Methylerythritol phosphate pathway of isoprenoid biosynthesis. Annu Rev Biochem. 2013;82:497-530. doi: 10.1146/annurev-biochem-052010-100934. 23746261