Record Information
Version1.0
Creation date2010-04-08 22:13:02 UTC
Update date2019-11-26 03:14:42 UTC
Primary IDFDB017348
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCurcumol
Description5-Methyl-5-hexen-2-one, also known as 4-acetyl-2-methyl-1-butene or fema 3365, belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol. 5-Methyl-5-hexen-2-one is an extremely weak basic (essentially neutral) compound (based on its pKa). 5-Methyl-5-hexen-2-one is a foliage, green, and vegetable tasting compound.
CAS Number4871-97-0
Structure
Thumb
Synonyms
SynonymSource
4-Acetyl-2-methyl-1-buteneHMDB
FEMA 3365HMDB
MethallylacetoneHMDB
5,8-Epoxy-10(14)-guaien-8-olHMDB
CurcumolMeSH
Predicted Properties
PropertyValueSource
Water Solubility0.18 g/LALOGPS
logP2.63ALOGPS
logP3.07ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)11.75ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.46 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity67.92 m³·mol⁻¹ChemAxon
Polarizability27.59 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC15H24O2
IUPAC name2-methyl-6-methylidene-9-(propan-2-yl)-11-oxatricyclo[6.2.1.0¹,⁵]undecan-8-ol
InChI IdentifierInChI=1S/C15H24O2/c1-9(2)13-8-14-11(4)5-6-12(14)10(3)7-15(13,16)17-14/h9,11-13,16H,3,5-8H2,1-2,4H3
InChI KeyQRMPRVXWPCLVNI-UHFFFAOYSA-N
Isomeric SMILESCC(C)C1CC23OC1(O)CC(=C)C2CCC3C
Average Molecular Weight236.3499
Monoisotopic Molecular Weight236.177630012
Classification
Description Belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentKetones
Alternative Parents
Substituents
  • Ketone
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

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 76.23%; H 10.23%; O 13.54%DFC
Melting PointMp 141-142°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D -32.26 (c, 2.127 in CHCl3)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-052f-9430000000-e1674cb346da569a2fb6Spectrum
Predicted GC-MSCurcumol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-052f-9430000000-e1674cb346da569a2fb6Spectrum
Predicted GC-MSCurcumol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000l-9030000000-399b7159ca48b41b17f7Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-2090000000-873dc9ce8ca841c2c385Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05n0-9250000000-2aec5e80266e381c8d6fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-077b489b17b45ea88ce3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-d47490971e8b0274931dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0290000000-80d9c57bbfa557fabffeSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-066r-6910000000-3ba867119318826e533bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-c0031dc201eac6b6350aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kr-0690000000-06dfb3057102cc0a9617Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-8472a524647920e2eae7Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0090000000-a35b1ee8d04c47073402Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4s-7950000000-d30c841ef7a06a60bed9Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-c0031dc201eac6b6350aSpectrum
NMR
TypeDescriptionView
ChemSpider ID2797480
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID3559861
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB38122
CRC / DFC (Dictionary of Food Compounds) IDKXH06-X:KXH06-X
EAFUS IDNot Available
Dr. Duke IDCURCUMOL
BIGG IDNot Available
KNApSAcK IDC00020353
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
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti cancer35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti sarcomic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
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).