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Showing Compound 5,6-Epoxy-7-megastigmen-9-one (FDB013585)

Record Information
Version1.0
Creation date2010-04-08 22:10:48 UTC
Update date2025-11-18 23:53:30 UTC
Primary IDFDB013585
Secondary Accession Numbers
  • FDB013586
Chemical Information
FooDB Name5,6-Epoxy-7-megastigmen-9-one
Description(5r,6s)-5,6-epoxy-7-megastigmen-9-one, also known as 5,6-epoxy-beta-ionone, 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 (5r,6s)-5,6-epoxy-7-megastigmen-9-one is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). (5r,6s)-5,6-epoxy-7-megastigmen-9-one can be found in garden tomato and root vegetables, which makes (5r,6s)-5,6-epoxy-7-megastigmen-9-one a potential biomarker for the consumption of these food products.
CAS Number23267-57-4
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
5,6-Epoxy-beta-iononeMeSH
4-(2,2,6-Trimethylbicyclo[4.1.0]hept-1-yl)-3-buten-2-one, 9CIdb_source
5,6-Epoxy-5,6-dihydro-b-iononedb_source
Predicted Properties
PropertyValueSource
Water Solubility0.048 g/LALOGPS
logP3.2ALOGPS
logP2.8ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)19.83ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area29.6 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity60.55 m³·mol⁻¹ChemAxon
Polarizability23.95 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC13H20O2
IUPAC name(3E)-4-{2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}but-3-en-2-one
InChI IdentifierInChI=1S/C13H20O2/c1-10(14)6-9-13-11(2,3)7-5-8-12(13,4)15-13/h6,9H,5,7-8H2,1-4H3/b9-6+
InChI KeyZTJZJYUGOJYHCU-RMKNXTFCSA-N
Isomeric SMILESCC(=O)\C=C\C12OC1(C)CCCC2(C)C
Average Molecular Weight208.2967
Monoisotopic Molecular Weight208.146329884
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
  • Alpha,beta-unsaturated ketone
  • Enone
  • Acryloyl-group
  • Ketone
  • Oxacycle
  • Ether
  • Oxirane
  • Dialkyl ether
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
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 74.96%; H 9.68%; O 15.36%DFC
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MS5,6-Epoxy-7-megastigmen-9-one, non-derivatized, GC-MS Spectrumsplash10-00di-3900000000-642601a39cf4828a95ccSpectrum
GC-MS5,6-Epoxy-7-megastigmen-9-one, non-derivatized, GC-MS Spectrumsplash10-00di-3900000000-642601a39cf4828a95ccSpectrum
Predicted GC-MS5,6-Epoxy-7-megastigmen-9-one, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00kf-9800000000-13d41ca061e64c920db9Spectrum
Predicted GC-MS5,6-Epoxy-7-megastigmen-9-one, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4l-1980000000-ab9ee34d0704e1203f752016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052f-6930000000-677e48043052ae8aa6eb2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05nf-9100000000-c9569a9bf6b01df749fb2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0390000000-25629cabf4557eb256b52016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1980000000-3ff703712ae234f705672016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0080-3900000000-d31c654648f4308ec2512016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-066r-0980000000-30ceab1651a7cfac80dc2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0920000000-c6d7089ea87e89a6ca352021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05g0-0910000000-a61bfd0db05ab7db837b2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052f-0940000000-3fbf6630fa03ee051c9a2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4l-1970000000-c4f484b79f9008b6e7592021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-009f-9300000000-a4b084ffa5ef5aab4e262021-09-23View Spectrum
NMRNot Available
ChemSpider ID4509354
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID5352481
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB0034984
CRC / DFC (Dictionary of Food Compounds) IDJFM41-W:JFM41-W
EAFUS ID1808
Dr. Duke IDBETA-IONONE-EPOXIDE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID23267-57-4
GoodScent IDrw1378141
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
fruit
  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
sweet
  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.
wood
  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
fruity
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
berry
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
woody
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
violet
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
orris
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
powdery
  1. 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).