Record Information
Version1.0
Creation date2011-03-17 23:25:50 UTC
Update date2019-11-26 03:20:41 UTC
Primary IDFDB021659
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name1-Epiprocurcumenol
DescriptionProcurcumenol is a member of the class of compounds known as guaianes. Guaianes are sesquiterpenoids with a structure based on the guaiane skeleton. Guaiane is a bicyclic compound consisting of a decahydroazulene moiety, substituted with two methyl groups and a 1-methylethyl group at the 1-, 4-, and 7-position, respectively. Procurcumenol is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Procurcumenol can be found in herbs and spices and turmeric, which makes procurcumenol a potential biomarker for the consumption of these food products.
CAS Number127214-97-5
Structure
Thumb
Synonyms
SynonymSource
EpiprocurcumenolMeSH
1-Epiprocurcumenoldb_source
4-Hydroxy-7(11),9-guaiadien-8-one; (1b,4b,5b)-formdb_source
Predicted Properties
PropertyValueSource
Water Solubility0.29 g/LALOGPS
logP2.4ALOGPS
logP2.78ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)18.69ChemAxon
pKa (Strongest Basic)-0.67ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity70.68 m³·mol⁻¹ChemAxon
Polarizability27.19 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC15H22O2
IUPAC name3-hydroxy-3,8-dimethyl-5-(propan-2-ylidene)-1,2,3,3a,4,5,6,8a-octahydroazulen-6-one
InChI IdentifierInChI=1S/C15H22O2/c1-9(2)12-8-13-11(5-6-15(13,4)17)10(3)7-14(12)16/h7,11,13,17H,5-6,8H2,1-4H3
InChI KeyRHBOHEXDGUVIIY-UHFFFAOYSA-N
Isomeric SMILESCC(C)=C1CC2C(CCC2(C)O)C(C)=CC1=O
Average Molecular Weight234.334
Monoisotopic Molecular Weight234.161979948
Classification
Description Belongs to the class of organic compounds known as guaianes. These are sesquiterpenoids with a structure based on the guaiane skeleton. Guaiane is a bicyclic compound consisting of a decahydroazulene moiety, substituted with two methyl groups and a 1-methylethyl group at the 1-, 4-, and 7-position, respectively.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentGuaianes
Alternative Parents
Substituents
  • Guaiane sesquiterpenoid
  • Tertiary alcohol
  • Cyclic alcohol
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionOilDFC
Mass CompositionC 76.88%; H 9.46%; O 13.66%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D -20.5 (c, 0.3 in MeOH)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSProcurcumenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-066u-3950000000-993f8de2081ec44fe521Spectrum
Predicted GC-MSProcurcumenol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03dr-4690000000-50dff9364ebbe493c97eSpectrum
Predicted GC-MSProcurcumenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-0190000000-83ff7bf49115c97d99a52015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-2970000000-40fd2709b561d8e607f22015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-9620000000-80e096a7985ac6ddecf22015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-6f7e6bc4fca4d90308432015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0190000000-14de31412f9f14f1d1b72015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-6940000000-45e1f7a1d3feb95a96702015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-9087f47ed0ae51229a172021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0190000000-8762faa7c896b602e28b2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-6930000000-7563fe81c0d128bcbf782021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0190000000-189a46161700f2a6f32a2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-3980000000-2bcf5d27f6a4299b43fe2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00nf-9210000000-bfcfb2c36e80c1528b452021-09-22View 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) IDJZM50-I:LBR41-P
EAFUS IDNot Available
Dr. Duke IDEPI-PROCURCUMENOL
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
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti TNF35222 A substance that diminishes the rate of a chemical reaction.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).