1.02011-06-09 23:26:07 UTC2020-09-17 15:31:25 UTCFDB021860(-)-beta-PhellandreneBeta-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-dieneb-Phellandrene L-formbeta-Phellandrene L-formL-beta-Phellandreneβ-phellandrene L-formC10H16136.234136.125200512(6S)-3-methylidene-6-(propan-2-yl)cyclohex-1-ene(+)-β-phellandrene6153-17-9[H][C@]1(CCC(=C)C=C1)C(C)CInChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,6,8,10H,3,5,7H2,1-2H3/t10-/m0/s1LFJQCDVYDGGFCH-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 monoterpenoidsOrganic compoundsLipids and lipid-like moleculesPrenol lipidsMonoterpenoidsAliphatic homomonocyclic compoundsBranched unsaturated hydrocarbonsCycloalkenesMonocyclic monoterpenoidsUnsaturated aliphatic hydrocarbonsAliphatic homomonocyclic compoundBranched unsaturated hydrocarbonCyclic olefinCycloalkeneHydrocarbonMonocyclic monoterpenoidOlefinP-menthane monoterpenoidUnsaturated aliphatic hydrocarbonUnsaturated hydrocarbonCyclic monoterpenesMenthane monoterpenoidsMenthane monoterpenoidsbeta-phellandreneLiquidlogp3.98logs-3.60solubility3.44e-02 g/llogp3.26iupac(6S)-3-methylidene-6-(propan-2-yl)cyclohex-1-eneaverage_mass136.234mono_mass136.125200512smiles[H][C@]1(CCC(=C)C=C1)C(C)CformulaC10H16inchiInChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,6,8,10H,3,5,7H2,1-2H3/t10-/m0/s1inchikeyLFJQCDVYDGGFCH-JTQLQIEISA-Npolar_surface_area0refractivity46.75polarizability17.22rotatable_bond_count1acceptor_count0donor_count0physiological_charge0formal_charge0Specdb::EiMs1851Specdb::CMs11729Specdb::CMs161340Specdb::MsMs64230Specdb::MsMs64231Specdb::MsMs64232Specdb::MsMs121335Specdb::MsMs121336Specdb::MsMs121337Specdb::MsMs2800282Specdb::MsMs2800283Specdb::MsMs2800284Specdb::MsMs2878400Specdb::MsMs2878401Specdb::MsMs2878402HMDB41633129#<Reference:0x00005556751dcad8>CarrotType 1specificDaucus carota ssp. sativus79200Pine nutType 1specificPinus3337