1.0 2010-04-08 22:10:47 UTC 2020-09-17 15:31:25 UTC FDB013568 (S)-alpha-Phellandrene alpha-Phellandrene, also known as menthadiene, is one of two known Phellandrene isomers, alpha- and beta-, which are double-bonded. In Œ±-phellandrene, both double bonds are endocyclic and in alpha-phellandrene, one of them is exocyclic. alpha-Phellandrene 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. alpha-Phellandrene is possibly neutral, insoluble in water, but miscible with ether. alpha-Phellandrene has a mint, spice, and turpentine taste. alpha-Phellandrene is found in highest concentrations in anises, common sages, and ceylon cinnamons and in lower concentrations in peppermints. alpha-Phellandrene has also been detected in dills, fennels, sweet basils, and tarragons. This could make alpha-phellandrene a potential biomarker for the consumption of these foods. The phellandrenes are used in fragrances because of their pleasing aromas. (+)-alpha-Phellandrene (4S)-p-Mentha-1,5-diene (4S)-p-Mentha-1(6),2-diene (5S)-2-Methyl-5-(propan-2-yl)cyclohexa-1,3-diene (5S)-5-Isopropyl-2-methylcyclohexa-1,3-diene (S)-(+)-a-Phellandrene (S)-(+)-alpha-Phellandrene (S)-(+)-α-phellandrene D-alpha-Phellandrene C10H16 136.234 136.125200512 (5S)-2-methyl-5-(propan-2-yl)cyclohexa-1,3-diene (+)-α-phellandrene 2243-33-6 [H][C@]1(CC=C(C)C=C1)C(C)C InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4-6,8,10H,7H2,1-3H3/t10-/m0/s1 OGLDWXZKYODSOB-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. Menthane monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aliphatic homomonocyclic compounds Branched unsaturated hydrocarbons Cyclic olefins Monocyclic monoterpenoids Unsaturated aliphatic hydrocarbons Aliphatic homomonocyclic compound Branched unsaturated hydrocarbon Cyclic olefin Hydrocarbon Monocyclic monoterpenoid Olefin P-menthane monoterpenoid Unsaturated aliphatic hydrocarbon Unsaturated hydrocarbon Cyclic monoterpenes Menthane monoterpenoids alpha-phellandrene Liquid logp 4.29 ALOGPS logs -3.01 ALOGPS solubility 1.33e-01 g/l ALOGPS logp 3.21 ChemAxon iupac (5S)-2-methyl-5-(propan-2-yl)cyclohexa-1,3-diene ChemAxon average_mass 136.234 ChemAxon mono_mass 136.125200512 ChemAxon smiles [H][C@]1(CC=C(C)C=C1)C(C)C ChemAxon formula C10H16 ChemAxon inchi InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4-6,8,10H,7H2,1-3H3/t10-/m0/s1 ChemAxon inchikey OGLDWXZKYODSOB-JTQLQIEISA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 47.82 ChemAxon polarizability 17.14 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 22165 Specdb::CMs 165128 Specdb::MsMs 59142 Specdb::MsMs 59143 Specdb::MsMs 59144 Specdb::MsMs 115200 Specdb::MsMs 115201 Specdb::MsMs 115202 Specdb::MsMs 2835006 Specdb::MsMs 2835007 Specdb::MsMs 2835008 Specdb::MsMs 2870846 Specdb::MsMs 2870847 Specdb::MsMs 2870848 HMDB34970 367 #<Reference:0x000055ce32046040> Ceylon cinnamon Type 1 specific Cinnamomum verum 128608 Dill Type 1 specific Anethum graveolens 40922 399.25 399.25 399.25 mg/100 g Fennel Type 1 specific Foeniculum vulgare 48038 Herbs and Spices Unknown generic Turmeric Type 1 specific Curcuma longa 136217 37.5 37.5 37.5 mg/100 g dill