1.0 2016-09-30 23:04:07 UTC 2020-05-11 19:57:32 UTC BMDB0003375 BMDB03375 (-)-Limonene D-Limonene, also known as L-limonen or dipentene, belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Thus, D-limonene is considered to be an isoprenoid lipid molecule. D-Limonene exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. D-Limonene exists in all living organisms, ranging from bacteria to humans. (+)-(4R)-Limonene (+)-(R)-Limonene (+)-4-Isopropenyl-1-methylcyclohexene (+)-Limonene (4R)-1-Methyl-4-isopropenylcyclohex-1-ene (4R)-4-Isopropenyl-1-methylcyclohexene (R)-(+)-Limonene (R)-(+)-p-Mentha-1,8-diene (R)-1-Methyl-4-(1-methylethenyl)cyclohexene (R)-4-Isopropenyl-1-methyl-1-cyclohexene (R)-p-Mentha-1,8-diene 4BetaH-p-mentha-1,8-diene D-(+)-Limonene D-Limonen AISA 5203-L (+)limonene Dipentene (-)-Limonene 1-Methyl-4-(1-methylethenyl)cyclohexene Limonene Limonene, (+-)-isomer (D)-Limonene 4-Mentha-1,8-diene Limonene, (R)-isomer (+)-Dipentene (+)-alpha-Limonene (+)-p-Mentha-1,8-diene (+)-Α-limonene (4R)-(+)-Limonene (4R)-1-Methyl-4-(1-methylethenyl)cyclohexene (4R)-Limonene (R)-1-Methyl-4-(prop-1-en-2-yl)cyclohex-1-ene (R)-Limonene 1-Methyl-4-prop-1-en-2-yl-cyclohexene (+)-(R)-4-Isopropenyl-1-methylcyclohexene D Limonene 4 Mentha 1,8 diene (R)-4-Isopropenyl-1-methylcyclohexene D-Limonene d-Limonene (4R)-1-Methyl-4-(prop-1-en-2-yl)cyclohex-1-ene R-Limonene p-Mentha-1,8-diene (±)-Dipentene (±)-Limonene (±)-alpha-Limonene (±)-α-Limonene 1,8-p-Menthadiene 1-Methyl-4-(prop-1-en-2-yl)cyclohex-1-ene 1-Methyl-4-isopropenyl-1-cyclohexene 1-Methyl-4-isopropenylcyclohexene 1-Methyl-p-isopropenyl-1-cyclohexene 4-Isopropenyl-1-methyl-1-cyclohexene 4-Isopropenyl-1-methylcyclohexene dl-Limonene Dipenten Limonen alpha-Limonene α-Limonene C10H16 136.234 136.125200512 (4R)-1-methyl-4-(prop-1-en-2-yl)cyclohex-1-ene α-limonene 5989-27-5 CC(=C)[C@@H]1CCC(C)=CC1 InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,10H,1,5-7H2,2-3H3/t10-/m0/s1 XMGQYMWWDOXHJM-JTQLQIEISA-N belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Menthane monoterpenoids Branched unsaturated hydrocarbons Cycloalkenes Monocyclic monoterpenoids Unsaturated aliphatic hydrocarbons Aliphatic homomonocyclic compound Branched unsaturated hydrocarbon Cyclic olefin Cycloalkene Hydrocarbon Monocyclic monoterpenoid Olefin P-menthane monoterpenoid Unsaturated aliphatic hydrocarbon Unsaturated hydrocarbon Aliphatic homomonocyclic compounds Cyclic monoterpenes Menthane monoterpenoids Menthane monoterpenoids limonene Liquid logp 4.50 ALOGPS logs -2.47 ALOGPS logp 3.22 ChemAxon iupac (4R)-1-methyl-4-(prop-1-en-2-yl)cyclohex-1-ene ChemAxon average_mass 136.234 ChemAxon mono_mass 136.125200512 ChemAxon smiles CC(=C)[C@@H]1CCC(C)=CC1 ChemAxon formula C10H16 ChemAxon inchi InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,10H,1,5-7H2,2-3H3/t10-/m0/s1 ChemAxon inchikey XMGQYMWWDOXHJM-JTQLQIEISA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 46.48 ChemAxon polarizability 17.55 ChemAxon rotatable_bond_count 1 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 Specdb::EiMs 1674 Specdb::NmrTwoD 1931 Specdb::NmrOneD 1996 Specdb::NmrOneD 3921 Specdb::NmrOneD 4200 Specdb::CMs 6865 Specdb::CMs 26804 Specdb::CMs 28502 Specdb::CMs 28807 Specdb::CMs 99850 Specdb::CMs 99851 Specdb::CMs 99852 Specdb::CMs 103753 Specdb::CMs 167667 Specdb::MsMs 2382 Specdb::MsMs 2383 Specdb::MsMs 2384 Specdb::MsMs 6021 Specdb::MsMs 6022 Specdb::MsMs 6023 Specdb::MsMs 250197 Specdb::MsMs 250198 Specdb::MsMs 250199 Specdb::MsMs 270135 Specdb::MsMs 270136 Specdb::MsMs 270137 Specdb::MsMs 3053483 Specdb::MsMs 3053484 Specdb::MsMs 3053485 Specdb::MsMs 3116352 Specdb::MsMs 3116353 Specdb::MsMs 3116354 Epidermis Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Milk Raw milk, by NMR and GC-MS Antunes-Fernandes EC, van Gastelen S, Dijkstra J, Hettinga KA, Vervoort J: Milk metabolome relates enteric methane emission to milk synthesis and energy metabolism pathways. J Dairy Sci. 2016 Aug;99(8):6251-6262. doi: 10.3168/jds.2015-10248. Epub 2016 May 26. 27236769 C06099 389747 FDB006329 440917 15382 DB08921 CPD-4886 Limonene C00010868 v. Braun, Julius; Lemke, Georg. Preparation of pure d- and l-limonene. Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen (1923), 56B 1562-3. Antunes-Fernandes EC, van Gastelen S, Dijkstra J, Hettinga KA, Vervoort J: Milk metabolome relates enteric methane emission to milk synthesis and energy metabolism pathways. J Dairy Sci. 2016 Aug;99(8):6251-6262. doi: 10.3168/jds.2015-10248. Epub 2016 May 26. 27236769