1.02020-03-18 23:28:16 UTC2020-12-07 19:07:15 UTCCDB0001942E-Geraniolbeta-Geraniol, also known as (E)-nerol, the isomer of nerol (or geranyl alcohol, is a monoterpenoid alcohol. It belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-eritritol-phosphate (MEP) pathway in the plastids (PMID: 7640522). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. beta-Geraniol is an isoprenoid lipid molecule that is very hydrophobic, practically insoluble in water, and relatively neutral. beta-Geraniol has a sweet, citrus, and floral taste. beta-Geraniol is found in highest concentrations in common grapes, black walnuts, and common thymes and in lower concentrations in cardamoms, common oregano, and gingers. beta-Geraniol has also been detected in lemon verbena, oval-leaf huckleberries, common pea, sweet cherries, and nopals. This could make beta-geraniol a potential biomarker for the consumption of these foods. It is found in as an alcohol and as its ester in many essential oils including geranium oil. It is the primary part of rose oil, palmarosa oil, and citronella oil (Java type) and occurs in small quantities in geranium, lemon, and many other essential oils. Geraniol is a monoterpenoid and an alcohol found in cannabis plants (PMID:6991645). Because it has a rose-like odor, it is commonly used in perfumes. It is used to create flavors such as peach, raspberry, grapefruit, red apple, plum, lime, orange, lemon, watermelon, pineapple, and blueberry. Geraniol is produced by the scent glands of honeybees to mark nectar-bearing flowers and locate the entrances to their hives (http//doi:10.1051/apido:19900403)(2E)-3,7-Dimethyl-2,6-octadien-1-ol(2E)-Geraniol(e)-3,7-Dimethyl-2,6-octadien-1-ol(e)-Geraniol(e)-Nerol2-trans-3,7-Dimethyl-2,6-octadien-1-ol3,7-Dimethyl-trans-2,6-octadien-1-olGeranyl alcoholLemonolt-Geranioltrans-3,7-Dimethyl-2,6-octadien-1-oltrans-Geraniolb-GeraniolΒ-geraniol(2E)-3,7-Dimethylocta-2,6-dien-1-ol2-trans-3,7-Dimethyl-2,6-octadiene-1-ol2E-Geraniol3,7-Dimethyl-(2E)-2,6-octadien-1-ol3,7-Dimethyl-(e)-2,6-octadien-1-olFEMA 2507Geranioltrans-2,6-Dimethyl-2,6-octadien-8-oltrans-3,7-Dimethy- octa-2,6-dien-1-olGeraniol, (Z)-isomerGeraniol, 1-(14)C-labeled, (e)-isomerNerolGeraniol, 2-(14)C-labeled, (e)-isomerGeraniol, titanium (4+) saltGeraniol, (e)-isomer(E)-3,7-Dimethyl-2,6-octadienoltrans-1-Hydroxy-3,7-dimethyl-2,6-octadienebeta-GeraniolC10H18O154.25154.1358(2E)-3,7-dimethylocta-2,6-dien-1-olgeraniol106-24-1CC(C)=CCC\C(C)=C\COInChI=1S/C10H18O/c1-9(2)5-4-6-10(3)7-8-11/h5,7,11H,4,6,8H2,1-3H3/b10-7+GLZPCOQZEFWAFX-JXMROGBWSA-N belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle.Acyclic monoterpenoidsOrganic compoundsLipids and lipid-like moleculesPrenol lipidsMonoterpenoidsAliphatic acyclic compoundsFatty alcoholsHydrocarbon derivativesPrimary alcoholsAcyclic monoterpenoidAlcoholAliphatic acyclic compoundFatty acylFatty alcoholHydrocarbon derivativeOrganic oxygen compoundOrganooxygen compoundPrimary alcohol3,7-dimethylocta-2,6-dien-1-olAcyclic monoterpenoidsAcyclic monoterpenoidsLinear monoterpenesmonoterpenoidprimary alcoholwater_solubility0.1 mg/mL at 25 °Clogp3.56melting_point< -15 °Clogp2.89logs-2.05logp2.5pka_strongest_acidic16.33pka_strongest_basic-2.2iupac(2E)-3,7-dimethylocta-2,6-dien-1-olaverage_mass154.25mono_mass154.1358smilesCC(C)=CCC\C(C)=C\COformulaC10H18OinchiInChI=1S/C10H18O/c1-9(2)5-4-6-10(3)7-8-11/h5,7,11H,4,6,8H2,1-3H3/b10-7+inchikeyGLZPCOQZEFWAFX-JXMROGBWSA-Npolar_surface_area20.23refractivity51.18polarizability19.67rotatable_bond_count4acceptor_count1donor_count1physiological_charge0formal_charge0number_of_rings0bioavailability1rule_of_fiveYesghose_filterYesveber_ruleYesmddr_like_ruleYesFDB01379213849989C0150063756617447C00000845GeraniolTurner 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/np50008a001.6991645McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015.7640522