1.0 2011-06-09 23:26:07 UTC 2020-09-17 15:31:25 UTC FDB021860 (-)-beta-Phellandrene Beta-Phellandrene, also known 2-p-menthadiene, is one of two known Phellandrene isomers, Œ±- and Œ≤-, which are double-bonded. In Œ±-phellandrene, both double bonds are endocyclic and in Œ≤-phellandrene, one of them is exocyclic. It 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. Plants biosynthesize phellandrene through geranyl pyrophosphate (GPP) in the mevalonate pathway (MVA, PMID: 17467679). The MVA pathway yields the precursors dimethylallyl pyrophosphate and isopentenyl pyrophosphate which combine to produce GPP. This resultant monoterpene undergoes cyclization to form a menthyl cationic species. A hydride shift then forms an allylic carbocation followed by an elimination reaction that occurs at one of two positions, yielding either alpha-phellandrene or beta-phellandrene. Beta-phellandrene colorless to pale yellow clear liquid with a minty, terpenic odor ( http://www.thegoodscentscompany.com/data/rw1103551.html#tophyp). It is found in allspice and is widely distributed in essential oils from various plant families including Angelica, Eucalyptus, Lavandula, Mentha, Pinus species, water fennel, Canada balsam and Cannibis. It is also used as a perfuming agent or fragrance ingredient in cosmetics. Beta-phellandrene is found in, or is added to many foods including dairy products, confectionery, frozen dairy treats, soups and sauces. It has also found use as a natural pesticide. It has recently been found to induce DNA damage at high doses (2850 mg/kg) (PMID: 28668705). (-)-3-Methylene-6-(1-methylethyl)cyclohexene (-)-b-Phellandrene (-)-beta-Phellandrene (-)-p-Mentha-1(7),2-diene (-)-β-phellandrene (3R)-3-Isopropyl-6-methylenecyclohexene (4R)-p-Mentha-1(7),2-diene (6R)-3-Methylidene-6-(propan-2-yl)cyclohex-1-ene (R)-3-Isopropyl-6-methylenecyclohexene (R)-p-Mentha-1(7),2-diene b-Phellandrene L-form beta-Phellandrene L-form L-beta-Phellandrene β-phellandrene L-form C10H16 136.234 136.125200512 (6S)-3-methylidene-6-(propan-2-yl)cyclohex-1-ene (+)-β-phellandrene 6153-17-9 [H][C@]1(CCC(=C)C=C1)C(C)C InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,6,8,10H,3,5,7H2,1-2H3/t10-/m0/s1 LFJQCDVYDGGFCH-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 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 Cyclic monoterpenes Menthane monoterpenoids Menthane monoterpenoids beta-phellandrene Liquid logp 3.98 ALOGPS logs -3.60 ALOGPS solubility 3.44e-02 g/l ALOGPS logp 3.26 ChemAxon iupac (6S)-3-methylidene-6-(propan-2-yl)cyclohex-1-ene ChemAxon average_mass 136.234 ChemAxon mono_mass 136.125200512 ChemAxon smiles [H][C@]1(CCC(=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,3,5,7H2,1-2H3/t10-/m0/s1 ChemAxon inchikey LFJQCDVYDGGFCH-JTQLQIEISA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 46.75 ChemAxon polarizability 17.22 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::EiMs 1851 Specdb::CMs 11729 Specdb::CMs 161340 Specdb::MsMs 64230 Specdb::MsMs 64231 Specdb::MsMs 64232 Specdb::MsMs 121335 Specdb::MsMs 121336 Specdb::MsMs 121337 Specdb::MsMs 2800282 Specdb::MsMs 2800283 Specdb::MsMs 2800284 Specdb::MsMs 2878400 Specdb::MsMs 2878401 Specdb::MsMs 2878402 HMDB41633 129 #<Reference:0x000055ce2e902368> Carrot Type 1 specific Daucus carota ssp. sativus 79200 Pine nut Type 1 specific Pinus 3337