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cis-Linalool 3,6-oxide (FDB020534)

Record Information
Version1.0
Creation date2010-04-08 22:15:05 UTC
Update date2019-11-26 03:19:05 UTC
Primary IDFDB020534
Secondary Accession Numbers
  • FDB006695
Chemical Information
FooDB Namecis-Linalool 3,6-oxide
Description(±)-cis-Linalyl oxide 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 (±)-cis-Linalyl oxide is a sweet, earthy, and floral tasting compound (±)-cis-Linalyl oxide is found, on average, in the highest concentration within a few different foods, such as teas (Camellia sinensis), red tea, and herbal tea and in a lower concentration in green tea and black tea (±)-cis-Linalyl oxide has also been detected, but not quantified in, several different foods, such as tarragons (Artemisia dracunculus), common oreganos (Origanum vulgare), garden tomato (var.), blackberries (Rubus), and garden tomatoes (Solanum lycopersicum). This could make (±)-cis-linalyl oxide a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on (±)-cis-Linalyl oxide.
CAS Number5989-33-3
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.5 g/LALOGPS
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
Polarizability19.43 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC10H18O2
IUPAC name2-[(2R,5S)-5-ethenyl-5-methyloxolan-2-yl]propan-2-ol
InChI IdentifierInChI=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-/m1/s1
InChI KeyBRHDDEIRQPDPMG-PSASIEDQSA-N
Isomeric SMILESCC(C)(O)[C@H]1CC[C@](C)(O1)C=C
Average Molecular Weight170.2487
Monoisotopic Molecular Weight170.13067982
Classification
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:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 70.55%; H 10.66%; O 18.80%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MScis-Epoxydihydrolinalool, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-9100000000-d76b0d8bd5839f5bad93Spectrum
Predicted GC-MScis-Epoxydihydrolinalool, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-003r-9720000000-d7880141bef77c136d15Spectrum
Predicted GC-MScis-Epoxydihydrolinalool, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-1900000000-3717374e13c0e4e46e012016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fl0-7900000000-1a57b949dcbd663fc1eb2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pbi-9000000000-29f24016ec67ee4e749b2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-92d23807ba882368b9c52016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-1900000000-9591ca26dd3aa91ec77b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00m0-9400000000-adb5d889f7dfc0e0d5582016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-8900000000-a536912550058a32831e2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f7p-9100000000-b3759eefd18d5faed1022021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kc6-9000000000-369ce7815f6cf7814da32021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-efbd93a1a83feefc94df2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0aor-3900000000-6b8e798821e4115bf1d02021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9100000000-ace0a44f890d3bb407342021-09-25View Spectrum
NMRNot Available
ChemSpider ID4933975
ChEMBL IDCHEMBL2252948
KEGG Compound IDNot Available
Pubchem Compound ID6428573
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB40726
CRC / DFC (Dictionary of Food Compounds) IDJVB43-D:MTJ98-E
EAFUS IDNot Available
Dr. Duke IDLINALOOL-OXIDE-B|CIS-LINALOOL-OXIDE|LINALOOL-OXIDE-(CIS-FURANOID)|LINALOOL-OXIDE-I
BIGG IDNot Available
KNApSAcK IDC00034746
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID5989-33-3
GoodScent IDrw1432371
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
flower
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
earthy
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
floral
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sweet
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
woody
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).