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
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 FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
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
ClassificationNot classified
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-3c1aa1a5e0f61835962d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udr-3900000000-86882c765e64ddc051922016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ldi-9000000000-a653f610d8c769c8f5812016-08-03View 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, Negativesplash10-0udi-0900000000-c373c9eea3cebf186f532021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-4c49b375f7aae96ad3052021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-1000-6900000000-ab085761a68f750732562021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udr-3900000000-fbc31cf20658ca9fcd342021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05n3-9500000000-edf4637ffc55f65c3f8f2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fr6-9100000000-b94cebb6da5a89465afb2021-10-21View Spectrum
NMRNot Available
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
Celery stalksExpected but not quantifiedNot AvailableC. W. Wilson Relative Recovery and Identification of Carbonyl Compounds from Celery Essential Oil. Journal of Food Science 35, 766-768, 1970
LemonExpected but not quantifiedNot AvailableDUKE
Wild celeryExpected but not quantifiedNot AvailableDUKE
Showing 1 to 3 of 3 entries
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
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).