Record Information
Version1.0
Creation date2010-04-08 22:12:11 UTC
Update date2019-11-26 03:12:38 UTC
Primary IDFDB016026
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameRotundifolone
DescriptionRotundifolone 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. Rotundifolone is an extremely weak basic (essentially neutral) compound (based on its pKa). Rotundifolone is a herbal and minty tasting compound. Rotundifolone is found, on average, in the highest concentration within spearmints and cornmints. Rotundifolone has also been detected, but not quantified in, herbs and spices. This could make rotundifolone a potential biomarker for the consumption of these foods.
CAS Number5945-46-0
Structure
Thumb
Synonyms
SynonymSource
1,2-Epoxy-p-menth-4(8)-en-3-oneHMDB
2,3-Epoxy-6-isopropylidene-3-methylcyclohexanoneHMDB
6-Methyl-3-(1-methylethylidene)-7-oxabicyclo[4.1.0]heptan-2-one, 9ciHMDB
Piperitenone oxideHMDB
1,2-Epoxy-P-menth-4(8)-en-3-oneHMDB
6-Methyl-3-(1-methylethylidene)-7-oxabicyclo[4.1.0]heptan-2-one, 9CIdb_source
P-Menth-4(8)-en-3-one, 1,2-epoxy-biospider
Rotundifolonedb_source
Predicted Properties
PropertyValueSource
Water Solubility8.95 g/LALOGPS
logP1.61ALOGPS
logP2.07ChemAxon
logS-1.3ALOGPS
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area29.6 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity46.56 m³·mol⁻¹ChemAxon
Polarizability18.49 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC10H14O2
IUPAC name6-methyl-3-(propan-2-ylidene)-7-oxabicyclo[4.1.0]heptan-2-one
InChI IdentifierInChI=1S/C10H14O2/c1-6(2)7-4-5-10(3)9(12-10)8(7)11/h9H,4-5H2,1-3H3
InChI KeyAKASWINDKIEEBO-UHFFFAOYSA-N
Isomeric SMILESCC(C)=C1CCC2(C)OC2C1=O
Average Molecular Weight166.217
Monoisotopic Molecular Weight166.099379692
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
  • 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 - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 72.26%; H 8.49%; O 19.25%DFC
Melting PointMp 27.5°DFC
Boiling PointBp1 86°DFC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]10D +166.5 (MeOH)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00o4-9300000000-28ac35eefccb97ecf8f7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-0d2244bb050ca70a3c49JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-4900000000-a49b13c97830692f36f0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-067i-9100000000-5d3ca3ad1a2c8d254117JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-ab194c3e028cf03581b8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-1900000000-a1934865dd6aa8ca0d4aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a59-9600000000-37561a809cd7b097631eJSpectraViewer
ChemSpider ID55800
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID61942
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB37044
CRC / DFC (Dictionary of Food Compounds) IDKMC41-G:KMC41-G
EAFUS ID3056
Dr. Duke IDPIPERITENONE-OXIDE|(+)-PIPERITENONE-OXIDE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1049431
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 / Bioactivities
DescriptorIDDefinitionReference
anti acetylcholinesterase38462 An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of enzyme acetylcholinesterase (EC 3.1.1.7), which helps breaking down of acetylcholine into choline and acetic acid.DUKE
insecticide24852 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
herbal
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
minty
  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).