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Showing Compound (1S,2R,4R)-1,2-Epoxy-p-menth-8-ene (FDB003372)

Record Information
Version1.0
Creation date2010-04-08 22:05:46 UTC
Update date2019-11-26 02:59:05 UTC
Primary IDFDB003372
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(1S,2R,4R)-1,2-Epoxy-p-menth-8-ene
Description1,2-epoxy-p-menth-8-ene, also known as limonene-1,2-epoxide or 1,2-epoxylimonene, is a member of the class of 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 practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 1,2-epoxy-p-menth-8-ene is a green tasting compound found in lemon and wild celery, which makes 1,2-epoxy-p-menth-8-ene a potential biomarker for the consumption of these food products.
CAS Number6909-30-4
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
1,2-EpoxylimoneneChEBI
4-Isopropenyl-1-methyl-7-oxabicyclo[4.1.0]heptaneChEBI
Limonene 1,2-oxideChEBI
Limonene-1,2-epoxide, cis-isomerMeSH
Limonene-1,2-epoxide, (1R-(1alpha,4beta,6alpha))-isomerMeSH
Limonene-1,2-epoxide, (1S-(1alpha,4alpha,6alpha))-isomerMeSH
Limonene-1,2-epoxide, cis-(+)-isomerMeSH
Limonene-1,2-oxideMeSH
LimoxideMeSH
Limonene-1,2-epoxide, trans-(+)-isomerMeSH
Limonene-1,2-epoxide, trans-isomerMeSH
Limonene-1,2-epoxideMeSH
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, MeSH
(+)-(e)-limonene oxidebiospider
(+)-trans-Limonene 1,2-epoxidebiospider
(+)-trans-limonene oxidebiospider
(+)-trans-p-Mentha-1,8-diene 1,2-epoxidebiospider
(1S,2R,4R)-4-Isopropenyl-1-methyl-1-cyclohexene 1,2-epoxidebiospider
(1S,4R)-1,2-Epoxy-p-menth-8-enebiospider
(e)-limonene oxidebiospider
D-LIMONENE 1,2-EPOXIDEbiospider
trans-1,2-Limonene epoxidebiospider
trans-1,2-limonene oxidebiospider
Trans-d-limonene oxidebiospider
Trans-limonen oxidebiospider
trans-Limonen-1,2-epoxidebiospider
Trans-limonene oxidebiospider
Trans-limonene oxydebiospider
trans-Limonene-1,2-epoxidebiospider
trans-limonene-1,2-oxidebiospider
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
Chemical FormulaC10H16O
IUPAC name1-methyl-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptane
InChI IdentifierInChI=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
Isomeric SMILESCC(=C)C1CCC2(C)OC2C1
Average Molecular Weight152.2334
Monoisotopic Molecular Weight152.120115134
Classification
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:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 78.90%; H 10.59%; O 10.51%DFC
Melting PointNot Available
Boiling PointBp10 78.5-80.5°DFC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]24D +83.22 (neat)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive Indexn24D 1.4657DFC
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MS(1S,2R,4R)-1,2-Epoxy-p-menth-8-ene, non-derivatized, GC-MS Spectrumsplash10-052f-9200000000-fecff1839cd311e2483cSpectrum
GC-MS(1S,2R,4R)-1,2-Epoxy-p-menth-8-ene, non-derivatized, GC-MS Spectrumsplash10-052f-9200000000-fecff1839cd311e2483cSpectrum
Predicted GC-MS(1S,2R,4R)-1,2-Epoxy-p-menth-8-ene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-003u-9200000000-d81e209c09694ad9f313Spectrum
Predicted GC-MS(1S,2R,4R)-1,2-Epoxy-p-menth-8-ene, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(1S,2R,4R)-1,2-Epoxy-p-menth-8-ene, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-3c1aa1a5e0f61835962d2016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udr-3900000000-86882c765e64ddc051922016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ldi-9000000000-a653f610d8c769c8f5812016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-b330335669a8886c1ed32016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-1900000000-b7f31881782717e4ef0d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05n0-9600000000-66905c235c49a53868412016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udr-3900000000-fbc31cf20658ca9fcd342021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05n3-9500000000-edf4637ffc55f65c3f8f2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fr6-9100000000-b94cebb6da5a89465afb2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-c373c9eea3cebf186f532021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-4c49b375f7aae96ad3052021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-1000-6900000000-ab085761a68f750732562021-09-22View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID449290
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDJHG15-B:CWO28-X
EAFUS IDNot Available
Dr. Duke IDTRANS-LIMONENE-1,2-OXIDE|TRANS-LIMONENE-OXIDE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID6909-30-4
GoodScent IDrw1450681
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
green
  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
  2. 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).