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3,5,5-Trimethyl-2-cyclohexen-1-one (FDB003216)

Record Information
Version1.0
Creation date2010-04-08 22:05:42 UTC
Update date2019-11-26 02:58:38 UTC
Primary IDFDB003216
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name3,5,5-Trimethyl-2-cyclohexen-1-one
Description3,5,5-Trimethyl-2-cyclohexen-1-one, also known as isoacetophorone or isoforone, 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-2-cyclohexen-1-one is a sweet, camphor, and camphoraceous tasting compound. 3,5,5-Trimethyl-2-cyclohexen-1-one is found, on average, in the highest concentration within kohlrabis (Brassica oleracea var. gongylodes). 3,5,5-Trimethyl-2-cyclohexen-1-one has also been detected, but not quantified in, several different foods, such as garden tomatoes (Solanum lycopersicum), fruits, saffrons (Crocus sativus), white mustards (Sinapis alba), and garden tomato (var.). This could make 3,5,5-trimethyl-2-cyclohexen-1-one a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 3,5,5-Trimethyl-2-cyclohexen-1-one.
CAS Number78-59-1
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.89 g/LALOGPS
logP1.9ALOGPS
logP2.32ChemAxon
logS-1.9ALOGPS
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity42.65 m³·mol⁻¹ChemAxon
Polarizability16.22 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC9H14O
IUPAC name3,5,5-trimethylcyclohex-2-en-1-one
InChI IdentifierInChI=1S/C9H14O/c1-7-4-8(10)6-9(2,3)5-7/h4H,5-6H2,1-3H3
InChI KeyHJOVHMDZYOCNQW-UHFFFAOYSA-N
Isomeric SMILESCC1=CC(=O)CC(C)(C)C1
Average Molecular Weight138.2069
Monoisotopic Molecular Weight138.10446507
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 Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Environmental role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 78.21%; H 10.21%; O 11.58%DFC
Melting Point-8.1 oC
Boiling PointBp10 89°DFC
Experimental Water Solubility12 mg/mL at 25 oCPARRISH,CF (1983)
Experimental logP1.70VEITH,GD ET AL. (1980)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
Densityd2020 0.92DFC
Refractive Indexn20D 1.4759DFC
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MS3,5,5-Trimethyl-2-cyclohexen-1-one, non-derivatized, GC-MS Spectrumsplash10-001i-9000000000-8ed7b012531653c3a41eSpectrum
GC-MS3,5,5-Trimethyl-2-cyclohexen-1-one, non-derivatized, GC-MS Spectrumsplash10-001i-9200000000-e8bfe4751592e28e4c9eSpectrum
GC-MS3,5,5-Trimethyl-2-cyclohexen-1-one, non-derivatized, GC-MS Spectrumsplash10-000i-2900000000-44ee32aafc71c88ceb86Spectrum
GC-MS3,5,5-Trimethyl-2-cyclohexen-1-one, non-derivatized, GC-MS Spectrumsplash10-001i-9000000000-35f5f51e1d1c8b9f41ebSpectrum
GC-MS3,5,5-Trimethyl-2-cyclohexen-1-one, non-derivatized, GC-MS Spectrumsplash10-001i-9000000000-8ed7b012531653c3a41eSpectrum
GC-MS3,5,5-Trimethyl-2-cyclohexen-1-one, non-derivatized, GC-MS Spectrumsplash10-001i-9200000000-e8bfe4751592e28e4c9eSpectrum
GC-MS3,5,5-Trimethyl-2-cyclohexen-1-one, non-derivatized, GC-MS Spectrumsplash10-000i-2900000000-44ee32aafc71c88ceb86Spectrum
GC-MS3,5,5-Trimethyl-2-cyclohexen-1-one, non-derivatized, GC-MS Spectrumsplash10-001i-9000000000-35f5f51e1d1c8b9f41ebSpectrum
Predicted GC-MS3,5,5-Trimethyl-2-cyclohexen-1-one, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-008i-9300000000-2b6a3c30cc2cb9b7c81dSpectrum
Predicted GC-MS3,5,5-Trimethyl-2-cyclohexen-1-one, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3,5,5-Trimethyl-2-cyclohexen-1-one, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-c0e6d09278faa8f9f6422021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-dccd82444801bb71001a2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-4900000000-5268782d409da6b9a25a2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053u-9100000000-6b6035d03526824e4f4a2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-10c654c5b0e1c7d814282015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-f5ce7cb3d1f20b415ad92015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-007c-9600000000-8b2034251abbccebb7392015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9700000000-eaf3d45b160fad9677282021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0560-9100000000-d0446ecf5f19dbc3eeae2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a7i-9000000000-49bfbbf2837b17d788982021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-928b413704490084a3032021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-928b413704490084a3032021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00xr-4900000000-88d428c6a2e6fff994aa2021-09-23View Spectrum
NMRNot Available
ChemSpider ID6296
ChEMBL IDCHEMBL1882894
KEGG Compound IDC14743
Pubchem Compound ID6544
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB31195
CRC / DFC (Dictionary of Food Compounds) IDCTL71-V:CTL71-V
EAFUS ID1901
Dr. Duke IDISOPHORONE|3,5,5-TRIMETHYLCYCLOHEX-2-ENONE
BIGG IDNot Available
KNApSAcK IDC00030540
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1036811
SuperScent ID6544
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
camphoraceous
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
tobacco
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
  2. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
cooling
  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.
sweet
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
green
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
camphor
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
fruity
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
musty
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
cedarwood
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
leather
  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).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.