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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-12 01:52:10 UTC
Update Date2019-07-23 06:32:20 UTC
HMDB IDHMDB0040338
Secondary Accession Numbers
  • HMDB40338
Metabolite Identification
Common Name3,5,5-Trimethyl-3-cyclohexen-1-one
Description3,5,5-Trimethyl-3-cyclohexen-1-one, also known as .beta-isophorone or b-phorone, belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond. 3,5,5-Trimethyl-3-cyclohexen-1-one is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 3,5,5-Trimethyl-3-cyclohexen-1-one has been detected, but not quantified in, a few different foods, such as fruits, herbs and spices, and saffrons. This could make 3,5,5-trimethyl-3-cyclohexen-1-one a potential biomarker for the consumption of these foods.
Structure
Data?1563863540
Synonyms
ValueSource
.beta-isophoroneHMDB
3,5,5-Trimethyl-3-cyclohexene-1-oneHMDB
3,5,5-Trimethylcyclohex-3-enoneHMDB
b-IsophoroneHMDB
b-PhoroneHMDB
beta -IsophoroneHMDB
beta -PhoroneHMDB
beta-IsophoroneHMDB
beta-PhoroneHMDB
Crocusatin eHMDB
Chemical FormulaC9H14O
Average Molecular Weight138.2069
Monoisotopic Molecular Weight138.10446507
IUPAC Name3,5,5-trimethylcyclohex-3-en-1-one
Traditional Name3,5,5-trimethylcyclohex-3-en-1-one
CAS Registry Number471-01-2
SMILES
CC1=CC(C)(C)CC(=O)C1
InChI Identifier
InChI=1S/C9H14O/c1-7-4-8(10)6-9(2,3)5-7/h5H,4,6H2,1-3H3
InChI KeyLKOKKQDYMZUSCG-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentCyclohexenones
Alternative Parents
Substituents
  • Cyclohexenone
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility4.57 g/LALOGPS
logP1.72ALOGPS
logP1.96ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)16.62ChemAxon
pKa (Strongest Basic)-7.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity42.67 m³·mol⁻¹ChemAxon
Polarizability16.27 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000b-9200000000-44cce750b46a7c0248bfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-ae6ee4405608e5f7a0c9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-5900000000-7e83a4ecb52be1c7aca0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052k-9000000000-c4a885c2890f13a74403Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-12e4fd56237f81a516deSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-57e3939106050a782b1aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000f-9600000000-89b45e9ad286053f2766Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB020063
KNApSAcK IDC00032863
Chemspider ID9704
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10108
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .