Curcumin (CHEM017316)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 04:14:18 UTC
Update Date2016-10-28 10:02:12 UTC
Accession NumberCHEM017316
Identification
Common NameCurcumin
ClassSmall Molecule
DescriptionA beta-diketone that is methane in which two of the hydrogens are substituted by feruloyl groups. A natural dyestuff found in the root of Curcuma longa.
Contaminant Sources
  • Cosmetic Chemicals
  • FooDB Chemicals
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
C.I. 75300ChEBI
C.I. natural yellow 3ChEBI
DiferuloylmethaneChEBI
e 100ChEBI
Kacha haldiChEBI
Natural yellow 3ChEBI
Turmeric yellowChEBI
Yellow, turmericMeSH
1,7-Bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dioneHMDB
1,7-Bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dioneHMDB
1,9-Bis(4-hydroxy-3-methoxyphenyl)-2,7-nonadiene-4,6-dioneHMDB
CI natural yellow 3HMDB
CucurminHMDB
CurcumaHMDB
Curcumin IHMDB
DiferaloylmethaneHMDB
GelbwurzHMDB
Golden sealHMDB
HaidrHMDB
HaladHMDB
HaldarHMDB
HaludHMDB
HydrastisHMDB
Merita earthHMDB
Orange rootHMDB
Safran d'indeHMDB
SouchetHMDB
Terra meritaHMDB
Tumeric yellowHMDB
TurmericHMDB
Turmeric (>98% curcurmin)HMDB
Turmeric oleoresin (79%-85% curcumin)HMDB
Yellow gingerHMDB
Yellow puccoonHMDB
Yellow rootHMDB
yo-KinHMDB
Chemical FormulaC21H20O6
Average Molecular Mass368.380 g/mol
Monoisotopic Mass368.126 g/mol
CAS Registry Number458-37-7
IUPAC Name(1E,6E)-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione
Traditional Namecurcumin
SMILESCOC1=CC(\C=C\C(=O)CC(=O)\C=C\C2=CC(OC)=C(O)C=C2)=CC=C1O
InChI IdentifierInChI=1S/C21H20O6/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/h3-12,24-25H,13H2,1-2H3/b7-3+,8-4+
InChI KeyVFLDPWHFBUODDF-FCXRPNKRSA-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
  • Hydroxycinnamic acid or derivatives
  • Methoxyphenol
  • Anisole
  • Phenoxy compound
  • Phenol ether
  • Styrene
  • Methoxybenzene
  • Phenol
  • 1,3-diketone
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • 1,3-dicarbonyl compound
  • Monocyclic benzene moiety
  • Acryloyl-group
  • Alpha,beta-unsaturated ketone
  • Enone
  • Ketone
  • Ether
  • Organooxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • 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 Solubility0.0058 g/LALOGPS
logP3.62ALOGPS
logP4.12ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)9.06ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area93.06 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity103.81 m³·mol⁻¹ChemAxon
Polarizability38.12 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0fbc-0923000000-107f42bbc825be91449bSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0fbc-0923000000-107f42bbc825be91449bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-0902000000-a583c69443735ecee34dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-006t-3090600000-d97f58b9779a3d4c58d5Spectrum
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
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITTOF , negativesplash10-0600-0920000000-c006d38848959c621ec5Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0982000000-2c508f0e4a39ae290728Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-00di-0950000000-af821cd7589af1e24d16Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0fk9-0981000000-e4da18f81a545b08874bSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-002b-2920000000-3c3aa8613bf16651cdf5Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-000t-0911000000-abf0df68155c943697d1Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-001i-0900000000-0a0213a836a78f6e54cdSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-03k9-0169000000-ba031996da79b96e1951Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-004r-0960000000-f8dd0033b656ce57faaaSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00di-0291000000-2396d815134514f2f735Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-014j-0982000000-9cbccf58679bdd2133efSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0209000000-f995da101a08357914b0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0913000000-6bece31c8c8078c2fda4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004j-1900000000-6706d488783638730883Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0109000000-3cbd5e4d9320bc54c318Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0729000000-ae0fe93ebdfbeed7cc4fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004v-0914000000-72385474a47d42818f05Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0419000000-9ca31d2513afa0489fabSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00ls-0924000000-a7bc7daf4e9622a19a4bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-008j-0922000000-5ce00b7393b9b7b00d5bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-016r-0609000000-79fd92244350d542a9f0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0171-0955000000-d16b5d995679749aff17Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002k-1943000000-404ab5fc28a3d651940eSpectrum
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 IDDB11672
HMDB IDHMDB0002269
FooDB IDFDB012292
Phenol Explorer ID713
KNApSAcK IDC00002731
BiGG IDNot Available
BioCyc IDCPD-6602
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCurcumin
Chemspider ID839564
ChEBI ID3962
PubChem Compound ID969516
Kegg Compound IDC10443
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10923784
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=12083767
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=12826232
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=14561543
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=14634121
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=15129424
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=15659840
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=15753945
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=15809436
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=15842781
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=15879598
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=16276182
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=16292655
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=16972983
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=17182546
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=18815282
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=19038979
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=19204190
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=19234767
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=20057137
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=21466422
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=21642934
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=22044005
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=22051121
25. https://www.ncbi.nlm.nih.gov/pubmed/?term=22118895
26. https://www.ncbi.nlm.nih.gov/pubmed/?term=22122768
27. https://www.ncbi.nlm.nih.gov/pubmed/?term=22211691
28. https://www.ncbi.nlm.nih.gov/pubmed/?term=22318308
29. https://www.ncbi.nlm.nih.gov/pubmed/?term=22753715
30. https://www.ncbi.nlm.nih.gov/pubmed/?term=23386263
31. https://www.ncbi.nlm.nih.gov/pubmed/?term=23574161
32. https://www.ncbi.nlm.nih.gov/pubmed/?term=9698073
33. Wehrli, Christof. Curcumin synthesis. PCT Int. Appl. (2007), 11pp.
34. Singh S, Khar A: Biological effects of curcumin and its role in cancer chemoprevention and therapy. Anticancer Agents Med Chem. 2006 May;6(3):259-70.
35. Maheshwari RK, Singh AK, Gaddipati J, Srimal RC: Multiple biological activities of curcumin: a short review. Life Sci. 2006 Mar 27;78(18):2081-7. Epub 2006 Jan 18.