Back to Compounds

Showing Compound 2,6,6-Trimethylcyclohex-2-en-1,4-dione (FDB004389)

Record Information
Version1.0
Creation date2010-04-08 22:06:13 UTC
Update date2019-11-26 02:59:59 UTC
Primary IDFDB004389
Secondary Accession Numbers
  • FDB019928
Chemical Information
FooDB Name2,6,6-Trimethylcyclohex-2-en-1,4-dione
Description2,6,6-trimethyl-2-cyclohexene-1,4-dione, also known as ketoisophorone, is a member of the class of 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. 2,6,6-trimethyl-2-cyclohexene-1,4-dione is slightly soluble (in water) and an extremely weak acidic compound (based on its pKa). 2,6,6-trimethyl-2-cyclohexene-1,4-dione is a sweet, leaf, and musty tasting compound found in herbs and spices and tea, which makes 2,6,6-trimethyl-2-cyclohexene-1,4-dione a potential biomarker for the consumption of these food products. 2,6,6-trimethyl-2-cyclohexene-1,4-dione exists in all eukaryotes, ranging from yeast to humans.
CAS Number1125-21-9
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility8.73 g/LALOGPS
logP1.51ALOGPS
logP2.16ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)18.85ChemAxon
pKa (Strongest Basic)-6.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity43.39 m³·mol⁻¹ChemAxon
Polarizability16.33 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC9H12O2
IUPAC name2,6,6-trimethylcyclohex-2-ene-1,4-dione
InChI IdentifierInChI=1S/C9H12O2/c1-6-4-7(10)5-9(2,3)8(6)11/h4H,5H2,1-3H3
InChI KeyAYJXHIDNNLJQDT-UHFFFAOYSA-N
Isomeric SMILESCC1=CC(=O)CC(C)(C)C1=O
Average Molecular Weight152.1904
Monoisotopic Molecular Weight152.083729628
Classification
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:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS2,6,6-Trimethylcyclohex-2-en-1,4-dione, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0pbc-9400000000-ac4a8e5a500a122e8961Spectrum
Predicted GC-MS2,6,6-Trimethylcyclohex-2-en-1,4-dione, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-1900000000-a2ede87c0b92081444bf2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-5900000000-43128d887aa49e04c9962015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-8359b62696f36de8253d2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-4d79e09516d33207e3522015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-1900000000-ebd44ede68a343ed2c8c2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052r-9300000000-edfbab726fbefc90241c2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-3cd265ceef2fb5f5db202021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-2900000000-031e7bfb242b17e4a4952021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uyl-9200000000-9950f21d73347619ba592021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-1900000000-bde85b5db3f5d24f0db42021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-053g-9300000000-e49845f95178fde26c7e2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-506b290021f45d0865df2021-09-23View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
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 ID2,6,6-TRIMETHYL-CYCLOHEX-2-EN-1,4-DIONE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
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
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
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).