Showing Compound Card for (±)-trans-Linalyl oxide (CDB000294)

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Record Information
Version1.0
Created at2020-03-19 00:29:24 UTC
Updated at2020-12-07 19:07:19 UTC
CannabisDB IDCDB000294
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name(±)-trans-Linalyl oxide
Description(±)-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-Linalool oxide is one of more than 140 terpenoids that are found in cannabis plants (PMID: 6991645 ) and the combination of these terpenoids produces the skunky, fruity odor characteristic of C. savita
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(e)-Linalool oxide aHMDB
5-ethenyltetrahydro-a,a,5-Trimethyl-(2R,5R)-rel-2-furanmethanolHMDB
e-Linalool oxide (furanoid)HMDB
Linalool oxide aHMDB
Linalool oxide IIHMDB
trans-Furanoid linalool oxideHMDB
trans-Linalool 3,6-oxideHMDB
trans-Linalool oxide (furanoid)HMDB
Chemical FormulaC10H18O2
Average Molecular Weight170.25
Monoisotopic Molecular Weight170.1307
IUPAC Name2-[(2S,5S)-5-ethenyl-5-methyloxolan-2-yl]propan-2-ol
Traditional Name2-[(2S,5S)-5-ethenyl-5-methyloxolan-2-yl]propan-2-ol
CAS Registry Number34995-77-2
SMILES
CC(C)(O)[C@@H]1CC[C@](C)(O1)C=C
InChI Identifier
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
InChI KeyBRHDDEIRQPDPMG-WCBMZHEXSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassTetrahydrofurans
Sub ClassNot Available
Direct ParentTetrahydrofurans
Alternative Parents
Substituents
  • Tetrahydrofuran
  • Tertiary alcohol
  • Oxacycle
  • Ether
  • Dialkyl ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.51ALOGPS
logP1.67ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)14.32ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.46 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity49.04 m³·mol⁻¹ChemAxon
Polarizability19.52 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MS(±)-trans-Linalyl oxide, non-derivatized, GC-MS Spectrumsplash10-052f-9000000000-e8c8defcb13d413ce23bSpectrum
GC-MS(±)-trans-Linalyl oxide, non-derivatized, GC-MS Spectrumsplash10-052f-9000000000-e8c8defcb13d413ce23bSpectrum
Predicted GC-MS(±)-trans-Linalyl oxide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-9100000000-d76b0d8bd5839f5bad93Spectrum
Predicted GC-MS(±)-trans-Linalyl oxide, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-003r-9720000000-d7880141bef77c136d15Spectrum
Predicted GC-MS(±)-trans-Linalyl oxide, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-1900000000-3717374e13c0e4e46e012016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fl0-7900000000-1a57b949dcbd663fc1eb2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pbi-9000000000-29f24016ec67ee4e749b2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-92d23807ba882368b9c52016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-1900000000-9591ca26dd3aa91ec77b2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00m0-9400000000-adb5d889f7dfc0e0d5582016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-efbd93a1a83feefc94df2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0aor-3900000000-6b8e798821e4115bf1d02021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9100000000-ace0a44f890d3bb407342021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-8900000000-a536912550058a32831e2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f7p-9100000000-b3759eefd18d5faed1022021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kc6-9000000000-369ce7815f6cf7814da32021-09-22View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0040727
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB020535
KNApSAcK IDC00034496
Chemspider ID4937513
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6432254
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Turner 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. [PubMed:6991645 ]
  2. McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. [PubMed:7640522 ]