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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:06:17 UTC
Update Date2019-07-23 06:17:55 UTC
HMDB IDHMDB0035158
Secondary Accession Numbers
  • HMDB35158
Metabolite Identification
Common Name1,2-Epoxy-p-menth-8-ene
Description1,2-Epoxy-p-menth-8-ene, also known as 1,2-epoxylimonene or limonene 1,2-oxide, belongs to the class of organic compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms. 1,2-Epoxy-p-menth-8-ene is an extremely weak basic (essentially neutral) compound (based on its pKa). 1,2-Epoxy-p-menth-8-ene is a green tasting compound. Outside of the human body, 1,2-Epoxy-p-menth-8-ene has been detected, but not quantified in, a few different foods, such as celery stalks, lemons, and wild celeries. This could make 1,2-epoxy-p-menth-8-ene a potential biomarker for the consumption of these foods. An epoxide resulting from the formal epoxidation of the cyclic double bond of limonene.
Structure
Data?1563862675
Synonyms
ValueSource
1,2-EpoxylimoneneChEBI
4-Isopropenyl-1-methyl-7-oxabicyclo[4.1.0]heptaneChEBI
Limonene 1,2-oxideChEBI
1-Methyl-4-(1-methylethenyl)-7-oxabicyclo[4.1.0]heptane, 9ciHMDB
1-Methyl-4-(1-methylvinyl)-7-oxabicyclo(4.1.0)heptaneHMDB
1-Methyl-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptaneHMDB
Limonene 1,2-epoxideHMDB
Limonene epoxideHMDB
Limonene monoxideHMDB
Limonene oxideHMDB
Limonene-1,2-epoxideHMDB
Limonene-1,2-epoxide, (1R-(1alpha,4beta,6alpha))-isomerHMDB
Limonene-1,2-epoxide, (1S-(1alpha,4alpha,6alpha))-isomerHMDB
Limonene-1,2-epoxide, cis-(+)-isomerHMDB
Limonene-1,2-epoxide, cis-isomerHMDB
Limonene-1,2-epoxide, trans-(+)-isomerHMDB
Limonene-1,2-oxideHMDB
LimoxideHMDB
Limonene-1,2-epoxide, trans-isomerHMDB
Chemical FormulaC10H16O
Average Molecular Weight152.2334
Monoisotopic Molecular Weight152.120115134
IUPAC Name1-methyl-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptane
Traditional Namelimonene 1,2-epoxide
CAS Registry Number1195-92-2
SMILES
CC(=C)C1CCC2(C)OC2C1
InChI Identifier
InChI=1S/C10H16O/c1-7(2)8-4-5-10(3)9(6-8)11-10/h8-9H,1,4-6H2,2-3H3
InChI KeyCCEFMUBVSUDRLG-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassOxepanes
Sub ClassNot Available
Direct ParentOxepanes
Alternative Parents
Substituents
  • Oxepane
  • Oxacycle
  • Ether
  • Oxirane
  • Dialkyl ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

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 Solubility0.35 g/LALOGPS
logP2.81ALOGPS
logP2.32ChemAxon
logS-2.6ALOGPS
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.53 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity45.24 m³·mol⁻¹ChemAxon
Polarizability18.2 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9200000000-fecff1839cd311e2483cSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9200000000-fecff1839cd311e2483cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-003u-9200000000-d81e209c09694ad9f313Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-3c1aa1a5e0f61835962dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udr-3900000000-86882c765e64ddc05192Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ldi-9000000000-a653f610d8c769c8f581Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-b330335669a8886c1ed3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-1900000000-b7f31881782717e4ef0dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05n0-9600000000-66905c235c49a5386841Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB003372
KNApSAcK IDC00035852
Chemspider ID82617
KEGG Compound IDC07271
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound91496
PDB IDNot Available
ChEBI ID16431
Food Biomarker OntologyNot Available
VMH IDNot Available
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.. .