Tetrahydrocurcumin (CHEM025849)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 22:38:23 UTC
Update Date2016-11-09 01:18:10 UTC
Accession NumberCHEM025849
Identification
Common NameTetrahydrocurcumin
ClassSmall Molecule
DescriptionA beta-diketone that is curcumin in which both of the double bonds have been reduced to single bonds.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
1,7-Bis(4-hydroxy-3-methoxyphenyl)-3,5-heptanedioneChEBI
Chemical FormulaC21H24O6
Average Molecular Mass372.412 g/mol
Monoisotopic Mass372.157 g/mol
CAS Registry Number36062-04-1
IUPAC Name1,7-bis(4-hydroxy-3-methoxyphenyl)heptane-3,5-dione
Traditional Nametetrahydrocurcumin
SMILESCOC1=CC(CCC(=O)CC(=O)CCC2=CC(OC)=C(O)C=C2)=CC=C1O
InChI IdentifierInChI=1S/C21H24O6/c1-26-20-11-14(5-9-18(20)24)3-7-16(22)13-17(23)8-4-15-6-10-19(25)21(12-15)27-2/h5-6,9-12,24-25H,3-4,7-8,13H2,1-2H3
InChI KeyLBTVHXHERHESKG-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as curcuminoids. These are aromatic compounds containing a curcumin moiety, which is composed of two aryl buten-2-one (feruloyl) chromophores joined by a methylene group.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassDiarylheptanoids
Sub ClassLinear diarylheptanoids
Direct ParentCurcuminoids
Alternative Parents
Substituents
  • Curcumin
  • Gingerdione
  • Methoxyphenol
  • Anisole
  • Phenoxy compound
  • Phenol ether
  • Methoxybenzene
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • 1,3-diketone
  • Benzenoid
  • 1,3-dicarbonyl compound
  • Monocyclic benzene moiety
  • Ketone
  • Ether
  • Organooxygen compound
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0056 g/LALOGPS
logP3.51ALOGPS
logP3.96ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)9.31ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area93.06 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity101.62 m³·mol⁻¹ChemAxon
Polarizability39.42 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004r-0910000000-fa5f9c88947d04535eb3Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0umr-9410140000-19c50b651dca5f38ec3cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0209000000-7dfd4c091aad667f4f26Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00bi-0922000000-4172923a1d3dfd5cefd5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004r-1911000000-8ecd77e0bdc5eeb2914cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0109000000-cc999937febfc38f47c1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0639000000-3347b9d7105791a849f6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05ru-5986000000-5bfd0dc38ca2bb0b9efeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-1049000000-140fb262cdbb389db98dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00ks-6962000000-30302cd971363baba315Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-3930000000-7ddc098840a945474666Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0219000000-9f478fd39c93a8ba2530Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0935000000-5253debe0acf5be8a731Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1921000000-1003e2c392e655b3af0fSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0005789
FooDB IDFDB005352
Phenol Explorer IDNot Available
KNApSAcK IDC00055176
BiGG IDNot Available
BioCyc IDCPD-13315
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID110569
ChEBI ID67263
PubChem Compound ID124072
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDECMDB23171
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=21116204
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=21467222
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=21887819
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=21928294
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=22072109
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=22156377
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=22212488
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=22574459
9. Lampe, W.; Smolinska, J. Ability of the two methyl groups of the quaternary base of 3,5-dimethylisoxazole to couple. III. Bull. acad. polon. sci., Ser. sci. chim., geol. et geograph (1958), 6 481-6.
10. Lampe, W.; Smolinska, J. Ability of the two methyl groups of the quaternary base of 3,5-dimethylisoxazole to couple. III. Bull. acad. polon. sci., Ser. sci. chim., geol. et geograph (1958), 6 481-6.
11. Heath DD, Pruitt MA, Brenner DE, Begum AN, Frautschy SA, Rock CL: Tetrahydrocurcumin in plasma and urine: quantitation by high performance liquid chromatography. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Sep 25;824(1-2):206-12.