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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-09-12 02:18:13 UTC
Update Date2019-07-23 06:33:02 UTC
HMDB IDHMDB0040726
Secondary Accession Numbers
  • HMDB40726
Metabolite Identification
Common Name(±)-cis-Linalyl oxide
Description(±)-cis-Linalyl oxide, also known as cis-linalool 3,6-oxide or linalool oxide b, 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 an extremely weak basic (essentially neutral) compound (based on its pKa) (±)-cis-Linalyl oxide is a sweet, earthy, and floral tasting compound. Outside of the human body, (±)-cis-Linalyl oxide is found, on average, in the highest concentration within tea (±)-cis-Linalyl oxide has also been detected, but not quantified in, several different foods, such as sweet basils, black elderberries, common oregano, garden tomato (var.), and papaya. This could make (±)-cis-linalyl oxide a potential biomarker for the consumption of these foods. A monoterpenoid that is 2-(2-hydroxypropan-2-yl)oxolane carying additional methyl and vinyl substituents both located at position 5 (the 2R,5S-diastereomer).
Structure
Data?1563863582
Synonyms
ValueSource
cis-Linalyl oxideChEBI
(Z)-Furanoid linalool oxideHMDB
5-Ethenyltetrahydro-a,a,5-trimethyl-(2R,5S)-rel-2-furanmethanolHMDB
5-Ethenyltetrahydro-a,a,5-trimethyl-cis-2-furanmethanolHMDB
cis-Furanoid linalool oxideHMDB
cis-Linalool 3,6-oxideHMDB
Linalool oxide bHMDB
Linalool oxide IHMDB
Chemical FormulaC10H18O2
Average Molecular Weight170.2487
Monoisotopic Molecular Weight170.13067982
IUPAC Name2-[(2R,5S)-5-ethenyl-5-methyloxolan-2-yl]propan-2-ol
Traditional Name2-[(2R,5S)-5-ethenyl-5-methyloxolan-2-yl]propan-2-ol
CAS Registry Number5989-33-3
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-/m1/s1
InChI KeyBRHDDEIRQPDPMG-PSASIEDQSA-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
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot 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
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9100000000-d76b0d8bd5839f5bad93Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-003r-9720000000-d7880141bef77c136d15Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-1900000000-3717374e13c0e4e46e01Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fl0-7900000000-1a57b949dcbd663fc1ebSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pbi-9000000000-29f24016ec67ee4e749bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-92d23807ba882368b9c5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-1900000000-9591ca26dd3aa91ec77bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00m0-9400000000-adb5d889f7dfc0e0d558Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Ulcerative Colitis
details
Associated Disorders and Diseases
Disease References
Ulcerative colitis
  1. Garner CE, Smith S, de Lacy Costello B, White P, Spencer R, Probert CS, Ratcliffe NM: Volatile organic compounds from feces and their potential for diagnosis of gastrointestinal disease. FASEB J. 2007 Jun;21(8):1675-88. Epub 2007 Feb 21. [PubMed:17314143 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB020534
KNApSAcK IDC00034746
Chemspider ID4933975
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6428573
PDB IDNot Available
ChEBI ID132839
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .