1.0 2010-04-08 22:15:05 UTC 2020-09-17 15:32:27 UTC FDB020535 trans-Linalool 3,6-oxide (±)-trans-Linalyl oxide, also known as (E)-linalool oxide or trans-Linalool oxide is an oxidized derivative of Linalool which is a terpene alcohol common in various flowers and spice plants. It belongs to the class of organic compounds known as tetrahydrofurans. These are heterocyclic compounds containing a saturated, aliphatic, five-membered ring where a carbon is replaced by an oxygen. From a biosynthetic point of view, trans-Linalool oxide is a monoterpenoid. 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-erythritol-phosphate (MEP) pathway in plant cell 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. Linalool oxide occurs in two distinctly different structural guises in nature. The most common structural form is based on a five member, furan-like ring structure. The less common form is based on a six member, pyran-like structure. Both types of linalool oxide exist as cis- and trans- isomers. Despite the differences in structure, the aromas of the different forms of linalool oxide have a strong family resemblance. The furan-based linalool oxide has a floral character, somewhat reminiscent of lavender, but this is dominated by the profile of black tea. The pyran-based linalool oxide is more obviously floral, with less resemblance to tea. It is used as a perfuming agent and a flavoring agent. trans-Linalool oxide exists as a clear or slightly yellow oil. It is a neutral, hydrophobic molecule that is insoluble in water. (±)-trans-Linalyl oxide is found within tea and ceylon cinnamons and has also been detected, but not quantified in, several different foods, such as common oregano, sweet basils, garden tomatoes, gingers, and tarragons. (±)-trans-Linalyl oxide (E)-Linalool oxide A 2-Furanmethanol, 5-ethenyltetrahydro-a,a,5-trimethyl-, (2R,5R)-rel- 5-Ethenyltetrahydro-a,a,5-trimethyl-(2R,5R)-rel-2-furanmethanol E-Linalool oxide (furanoid) Linalool oxide A Linalool oxide II Linalyl oxide; (±)-trans-form trans-Furanoid linalool oxide trans-Linalool 3,6-oxide trans-Linalool oxide (furanoid) C10H18O2 170.2487 170.13067982 2-[(2S,5S)-5-ethenyl-5-methyloxolan-2-yl]propan-2-ol 2-[(2S,5S)-5-ethenyl-5-methyloxolan-2-yl]propan-2-ol 34995-77-2 CC(C)(O)[C@@H]1CC[C@](C)(O1)C=C InChI=1S/C10H18O2/c1-5-10(4)7-6-8(12-10)9(2,3)11/h5,8,11H,1,6-7H2,2-4H3/t8-,10+/m0/s1 BRHDDEIRQPDPMG-WCBMZHEXSA-N belongs to the class of organic compounds known as tetrahydrofurans. These are heterocyclic compounds containing a saturated, aliphatic, five-membered ring where a carbon is replaced by an oxygen. Tetrahydrofurans Organic compounds Organoheterocyclic compounds Tetrahydrofurans Aliphatic heteromonocyclic compounds Dialkyl ethers Hydrocarbon derivatives Oxacyclic compounds Tertiary alcohols Alcohol Aliphatic heteromonocyclic compound Dialkyl ether Ether Hydrocarbon derivative Organic oxygen compound Organooxygen compound Oxacycle Tertiary alcohol Tetrahydrofuran logp 1.51 ALOGPS logs -2.05 ALOGPS solubility 1.50e+00 g/l ALOGPS logp 1.67 ChemAxon pka_strongest_acidic 14.32 ChemAxon pka_strongest_basic -3.1 ChemAxon iupac 2-[(2S,5S)-5-ethenyl-5-methyloxolan-2-yl]propan-2-ol ChemAxon average_mass 170.2487 ChemAxon mono_mass 170.13067982 ChemAxon smiles CC(C)(O)[C@@H]1CC[C@](C)(O1)C=C ChemAxon formula C10H18O2 ChemAxon inchi InChI=1S/C10H18O2/c1-5-10(4)7-6-8(12-10)9(2,3)11/h5,8,11H,1,6-7H2,2-4H3/t8-,10+/m0/s1 ChemAxon inchikey BRHDDEIRQPDPMG-WCBMZHEXSA-N ChemAxon polar_surface_area 29.46 ChemAxon refractivity 49.04 ChemAxon polarizability 19.52 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 2658 Specdb::CMs 29081 Specdb::CMs 46932 Specdb::CMs 102179 Specdb::CMs 171930 Specdb::MsIr 9065 Specdb::MsIr 9066 Specdb::MsIr 9067 Specdb::NmrOneD 290415 Specdb::NmrOneD 290416 Specdb::NmrOneD 290417 Specdb::NmrOneD 290418 Specdb::NmrOneD 290419 Specdb::NmrOneD 290420 Specdb::NmrOneD 290421 Specdb::NmrOneD 290422 Specdb::NmrOneD 290423 Specdb::NmrOneD 290424 Specdb::NmrOneD 290425 Specdb::NmrOneD 290426 Specdb::NmrOneD 290427 Specdb::NmrOneD 290428 Specdb::NmrOneD 290429 Specdb::NmrOneD 290430 Specdb::NmrOneD 290431 Specdb::NmrOneD 290432 Specdb::NmrOneD 290433 Specdb::NmrOneD 290434 Specdb::MsMs 178623 Specdb::MsMs 178624 Specdb::MsMs 178625 Specdb::MsMs 180942 Specdb::MsMs 180943 Specdb::MsMs 180944 Specdb::MsMs 2370071 Specdb::MsMs 2370072 Specdb::MsMs 2370073 Specdb::MsMs 2569457 Specdb::MsMs 2569458 Specdb::MsMs 2569459 HMDB40727 #<Reference:0x000055ce30545660> Black elderberry Type 1 specific Sambucus nigra 4202 Black tea Type 1 155.625 290.0 21.25 mg/100 g Blackberry Type 1 specific Rubus Ceylon cinnamon Type 1 specific Cinnamomum verum 128608 1.25 1.25 1.25 mg/100 g Cherry tomato Type 1 specific Solanum lycopersicum var. cerasiforme 195583 Common oregano Type 1 specific Origanum vulgare 39352 Evergreen blackberry Type 1 specific Rubus laciniatus Garden tomato Type 1 specific Solanum lycopersicum 4081 Garden tomato (var.) Type 1 specific Solanum lycopersicum var. lycopersicum 397755 Ginger Type 1 specific Zingiber officinale 94328 Ginkgo nuts Type 1 specific Ginkgo biloba 3311 Green tea Type 1 155.625 290.0 21.25 mg/100 g Herbal tea Type 1 155.625 290.0 21.25 mg/100 g Papaya Type 1 specific Carica papaya 3649 Red tea Type 1 155.625 290.0 21.25 mg/100 g Sweet basil Type 1 specific Ocimum basilicum 39350 Tarragon Type 1 specific Artemisia dracunculus 72341 Tea Type 1 specific Camellia sinensis 4442 155.625 290.0 21.25 mg/100 g floral flower