Record Information
Version1.0
Creation date2010-04-08 22:06:30 UTC
Update date2019-11-26 03:00:20 UTC
Primary IDFDB005025
Secondary Accession NumbersNot Available
Chemical Information
FooDB Namecis-Limonene-1,2-oxide
Description(4r)-limonene 1α,2α-epoxide, also known as 1beta,2beta-epoxy-4betah-P-menth-8-ene, 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 (4r)-limonene 1α,2α-epoxide is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). (4r)-limonene 1α,2α-epoxide is a citrus and fresh tasting compound found in lemon and wild celery, which makes (4r)-limonene 1α,2α-epoxide a potential biomarker for the consumption of these food products.
CAS Number13837-75-7
Structure
Thumb
Synonyms
SynonymSource
(1R,4R,6S)-4-Isopropenyl-1-methyl-7-oxabicyclo[4.1.0]heptaneChEBI
1beta,2beta-Epoxy-4betah-p-menth-8-eneChEBI
1b,2b-Epoxy-4betah-p-menth-8-eneGenerator
1Β,2β-epoxy-4betah-p-menth-8-eneGenerator
1,2-Epoxy-cis-p-menth-8-enemanual
1,2-Epoxydipentenemanual
1a,2a-Epoxylimonenemanual
7-Oxabicyclo[4.1.0]heptane, 1-methyl-4-(1-methylethenyl)-, (1a,4a,6a)-manual
7-Oxabicyclo[4.1.0]heptane, 1-methyl-4-(1-methylethenyl)-, (1R,4R,6S)-rel-manual
cis-1,2-Limonene epoxidebiospider
cis-Limonen-1,2-epoxidebiospider
cis-limonene 1,2-epoxidebiospider
cis-Limonene monoepoxidemanual
Cis-limonene oxidebiospider
Limonene oxide, cis-biospider
Limonene, epoxy, cisbiospider
p-Menth-8-ene, 1,2-epoxy-, cis- (8CI)manual
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
Polarizability18.19 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC10H16O
IUPAC name(1R,4R,6S)-1-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/t8-,9+,10-/m1/s1
InChI KeyCCEFMUBVSUDRLG-KXUCPTDWSA-N
Isomeric SMILESCC(=C)[C@@H]1CC[C@@]2(C)O[C@H]2C1
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
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
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
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-3c1aa1a5e0f61835962dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udr-3900000000-86882c765e64ddc05192JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ldi-9000000000-a653f610d8c769c8f581JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-b330335669a8886c1ed3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-1900000000-b7f31881782717e4ef0dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05n0-9600000000-66905c235c49a5386841JSpectraViewer
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID6430738
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDCIS-LIMONENE-1,2-OXIDE|CIS-LIMONENE-OXIDE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID13837-75-7
GoodScent IDNot Available
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
fresh
  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
citrus
  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
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).