Record Information
Version1.0
Creation date2010-04-08 22:05:42 UTC
Update date2018-05-29 18:26:54 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 is a flavouring ingredient. It is present in cranberries (Vaccinium microcarpa) and saffron (Crocus sativus), as well as in other herbs and spices.
CAS Number78-59-1
Structure
Thumb
Synonyms
SynonymSource
1,1,3-Trimethyl-3-cyclohexene-5-oneChEBI
3,5,5-Trimethyl-2-cyclohexen-1-ONChEBI
IsoacetophoroneChEBI
IsoforoneChEBI
IsooctopheroneChEBI
IzoforonChEBI
1,1, 3-Trimethyl-3-cyclohexene-5-oneHMDB
1,5,5-Trimethyl-1-cyclohexen-3-oneHMDB
3,3,5-Trimethyl-2-cyclohexen-1-oneHMDB
3,5, 5-Trimethyl-2-cyclohexene-1-oneHMDB
3,5,5-Trimethyl-2-cyclohexene-1-oneHMDB
3,5,5-Trimethyl-2-cyclohexenoneHMDB
3,5,5-Trimethylcyclohex-2-enoneHMDB
3,5,5-Trimethylcyclohexen oneHMDB
3,5,5-Trimethylcyclohexen-2-one-1HMDB
3,5,5-TrimethylcyclohexenoneHMDB
3,5,5-Trimetil-2-cicloesen-1-oneHMDB
a-IsophoroneHMDB
alpha -IsophoronHMDB
alpha -IsophoroneHMDB
alpha-IsophoroneHMDB
DIIsophoroneHMDB
FEMA 3553HMDB
IsoforonHMDB
IsophoronHMDB
IsophoroneHMDB
Isophorone, reagHMDB
Nchem.180-comp3HMDB
α-isophoronbiospider
α-isophoronebiospider
2-Cyclohexen-1-one, 3,5, 5-trimethyl-biospider
2-Cyclohexen-1-one, 3,5,5-trimethyl-biospider
3,5,5-Trimethyl-2-cyclohexen-1-onbiospider
3,5,5-trimethylcyclohex-2-en-1-onebiospider
Alpha-isophoronebiospider
nchem.180-comp3biospider
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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
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
Spectrum TypeDescriptionSplash Key
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
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.