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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:33:54 UTC
Update Date2022-03-07 02:53:51 UTC
HMDB IDHMDB0033801
Secondary Accession Numbers
  • HMDB33801
Metabolite Identification
Common NameDemethoxycurcumin
DescriptionDemethoxycurcumin, also known as curcuminii or BHCFM, 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. Demethoxycurcumin is found, on average, in the highest concentration within turmerics (Curcuma longa). Demethoxycurcumin has also been detected, but not quantified in, a few different foods, such as beverages, herbs and spices, and root vegetables. This could make demethoxycurcumin a potential biomarker for the consumption of these foods. Demethoxycurcumin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on Demethoxycurcumin.
Structure
Data?1563862462
Synonyms
ValueSource
(1E,6E)-1-(4-Hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-1,6-heptadiene-3,5-dioneChEBI
(1E,6E)-1-(4-Hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-hepta-1,6-diene-3,5-dioneChEBI
4-Hydroxycinnamoyl(feroyl)methaneChEBI
4-Hydroxycinnamoyl(feruloyl)methaneChEBI
BHCFMChEBI
CurcuminIIChEBI
Feruloyl-p-hydroxycinnnamoylmethaneChEBI
MonodemethoxycurcuminMeSH
Curcumin IIMeSH
Demethoxy-curcuminMeSH
1-(4-Hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione, 9ciHMDB
P-HydroxycinnamoylferuloylmethaneHMDB
Chemical FormulaC20H18O5
Average Molecular Weight338.3539
Monoisotopic Molecular Weight338.115423686
IUPAC Name(1E,6E)-1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione
Traditional Name(1E,6E)-1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione
CAS Registry Number22608-11-3
SMILES
COC1=CC(\C=C\C(=O)CC(=O)\C=C\C2=CC=C(O)C=C2)=CC=C1O
InChI Identifier
InChI=1S/C20H18O5/c1-25-20-12-15(6-11-19(20)24)5-10-18(23)13-17(22)9-4-14-2-7-16(21)8-3-14/h2-12,21,24H,13H2,1H3/b9-4+,10-5+
InChI KeyHJTVQHVGMGKONQ-LUZURFALSA-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
  • Desmethoxycurcumin
  • 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
Ontology
Disposition

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point168 °CNot Available
Boiling Point571.40 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility30.6 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP3.150 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0067 g/LALOGPS
logP3.54ALOGPS
logP4.28ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)8.84ChemAxon
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area83.83 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity97.35 m³·mol⁻¹ChemAxon
Polarizability35.35 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+177.10430932474
DeepCCS[M-H]-174.74630932474
DeepCCS[M-2H]-208.97130932474
DeepCCS[M+Na]+184.32630932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DemethoxycurcuminCOC1=CC(\C=C\C(=O)CC(=O)\C=C\C2=CC=C(O)C=C2)=CC=C1O5671.3Standard polar33892256
DemethoxycurcuminCOC1=CC(\C=C\C(=O)CC(=O)\C=C\C2=CC=C(O)C=C2)=CC=C1O3245.5Standard non polar33892256
DemethoxycurcuminCOC1=CC(\C=C\C(=O)CC(=O)\C=C\C2=CC=C(O)C=C2)=CC=C1O3622.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Demethoxycurcumin,1TMS,isomer #1COC1=CC(/C=C/C(=O)CC(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C=C2)=CC=C1O3373.1Semi standard non polar33892256
Demethoxycurcumin,1TMS,isomer #2COC1=CC(/C=C/C(=O)CC(=O)/C=C/C2=CC=C(O)C=C2)=CC=C1O[Si](C)(C)C3364.1Semi standard non polar33892256
Demethoxycurcumin,1TMS,isomer #3COC1=CC(/C=C/C(=CC(=O)/C=C/C2=CC=C(O)C=C2)O[Si](C)(C)C)=CC=C1O3621.5Semi standard non polar33892256
Demethoxycurcumin,1TMS,isomer #4COC1=CC(/C=C/C(=O)C=C(/C=C/C2=CC=C(O)C=C2)O[Si](C)(C)C)=CC=C1O3600.9Semi standard non polar33892256
Demethoxycurcumin,2TMS,isomer #1COC1=CC(/C=C/C(=O)CC(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C=C2)=CC=C1O[Si](C)(C)C3437.4Semi standard non polar33892256
Demethoxycurcumin,2TMS,isomer #2COC1=CC(/C=C/C(=CC(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C=C2)O[Si](C)(C)C)=CC=C1O3593.3Semi standard non polar33892256
Demethoxycurcumin,2TMS,isomer #3COC1=CC(/C=C/C(=O)C=C(/C=C/C2=CC=C(O[Si](C)(C)C)C=C2)O[Si](C)(C)C)=CC=C1O3591.5Semi standard non polar33892256
Demethoxycurcumin,2TMS,isomer #4COC1=CC(/C=C/C(=CC(=O)/C=C/C2=CC=C(O)C=C2)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C3605.1Semi standard non polar33892256
Demethoxycurcumin,2TMS,isomer #5COC1=CC(/C=C/C(=O)C=C(/C=C/C2=CC=C(O)C=C2)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C3586.0Semi standard non polar33892256
Demethoxycurcumin,3TMS,isomer #1COC1=CC(/C=C/C(=CC(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C=C2)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C3620.9Semi standard non polar33892256
Demethoxycurcumin,3TMS,isomer #1COC1=CC(/C=C/C(=CC(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C=C2)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C3591.0Standard non polar33892256
Demethoxycurcumin,3TMS,isomer #2COC1=CC(/C=C/C(=O)C=C(/C=C/C2=CC=C(O[Si](C)(C)C)C=C2)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C3617.6Semi standard non polar33892256
Demethoxycurcumin,3TMS,isomer #2COC1=CC(/C=C/C(=O)C=C(/C=C/C2=CC=C(O[Si](C)(C)C)C=C2)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C3588.4Standard non polar33892256
Demethoxycurcumin,1TBDMS,isomer #1COC1=CC(/C=C/C(=O)CC(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)=CC=C1O3682.1Semi standard non polar33892256
Demethoxycurcumin,1TBDMS,isomer #2COC1=CC(/C=C/C(=O)CC(=O)/C=C/C2=CC=C(O)C=C2)=CC=C1O[Si](C)(C)C(C)(C)C3650.6Semi standard non polar33892256
Demethoxycurcumin,1TBDMS,isomer #3COC1=CC(/C=C/C(=CC(=O)/C=C/C2=CC=C(O)C=C2)O[Si](C)(C)C(C)(C)C)=CC=C1O3891.7Semi standard non polar33892256
Demethoxycurcumin,1TBDMS,isomer #4COC1=CC(/C=C/C(=O)C=C(/C=C/C2=CC=C(O)C=C2)O[Si](C)(C)C(C)(C)C)=CC=C1O3864.9Semi standard non polar33892256
Demethoxycurcumin,2TBDMS,isomer #1COC1=CC(/C=C/C(=O)CC(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)=CC=C1O[Si](C)(C)C(C)(C)C4003.6Semi standard non polar33892256
Demethoxycurcumin,2TBDMS,isomer #2COC1=CC(/C=C/C(=CC(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)O[Si](C)(C)C(C)(C)C)=CC=C1O4184.0Semi standard non polar33892256
Demethoxycurcumin,2TBDMS,isomer #3COC1=CC(/C=C/C(=O)C=C(/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)O[Si](C)(C)C(C)(C)C)=CC=C1O4180.1Semi standard non polar33892256
Demethoxycurcumin,2TBDMS,isomer #4COC1=CC(/C=C/C(=CC(=O)/C=C/C2=CC=C(O)C=C2)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C4150.8Semi standard non polar33892256
Demethoxycurcumin,2TBDMS,isomer #5COC1=CC(/C=C/C(=O)C=C(/C=C/C2=CC=C(O)C=C2)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C4131.7Semi standard non polar33892256
Demethoxycurcumin,3TBDMS,isomer #1COC1=CC(/C=C/C(=CC(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C4401.5Semi standard non polar33892256
Demethoxycurcumin,3TBDMS,isomer #1COC1=CC(/C=C/C(=CC(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C4207.2Standard non polar33892256
Demethoxycurcumin,3TBDMS,isomer #2COC1=CC(/C=C/C(=O)C=C(/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C4401.9Semi standard non polar33892256
Demethoxycurcumin,3TBDMS,isomer #2COC1=CC(/C=C/C(=O)C=C(/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C4208.3Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Demethoxycurcumin GC-MS (Non-derivatized) - 70eV, Positivesplash10-00r2-0901000000-654fca3f02d69e7560db2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Demethoxycurcumin GC-MS (2 TMS) - 70eV, Positivesplash10-014i-3071900000-50aab8ffd9b366fd14d72017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Demethoxycurcumin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Demethoxycurcumin 50V, Positive-QTOFsplash10-0002-0900000000-9517befe911ff515a3922021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Demethoxycurcumin 10V, Negative-QTOFsplash10-000i-0239000000-696b9f742f1375d511b62021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Demethoxycurcumin 30V, Negative-QTOFsplash10-014i-0910000000-9ba8139233df2e7399cd2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Demethoxycurcumin 20V, Negative-QTOFsplash10-014i-0920000000-d6ec1db1bc78454ca02e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Demethoxycurcumin 30V, Positive-QTOFsplash10-002b-0910000000-2b60408614dbac128af72021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Demethoxycurcumin 40V, Positive-QTOFsplash10-0002-0900000000-5fbd4f101ab8f66c229a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Demethoxycurcumin 20V, Positive-QTOFsplash10-0a6s-0961000000-682f6b15c69a852c5c252021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Demethoxycurcumin 10V, Positive-QTOFsplash10-000i-0219000000-e3bd2864892e4f6e23182021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Demethoxycurcumin 40V, Negative-QTOFsplash10-014i-0910000000-dc9c78751e44dd920a702021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Demethoxycurcumin 50V, Negative-QTOFsplash10-014i-0900000000-0a19a373bd22907fff2f2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Demethoxycurcumin 10V, Positive-QTOFsplash10-000i-0419000000-127d78c62fb7431896b52016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Demethoxycurcumin 20V, Positive-QTOFsplash10-002b-0901000000-c40b24a8778d2fa9787d2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Demethoxycurcumin 40V, Positive-QTOFsplash10-002b-1900000000-82aa8b73d450c54c4c302016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Demethoxycurcumin 10V, Negative-QTOFsplash10-000i-0309000000-1e9e9a7c9cdc0d078ad52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Demethoxycurcumin 20V, Negative-QTOFsplash10-000j-0914000000-656374264de68ab93dd62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Demethoxycurcumin 40V, Negative-QTOFsplash10-07xs-1911000000-d77a4b8103374473002f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Demethoxycurcumin 10V, Positive-QTOFsplash10-000i-0709000000-d28143d2357c12a71e642021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Demethoxycurcumin 20V, Positive-QTOFsplash10-0002-0901000000-071370f22d66d14d47d22021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Demethoxycurcumin 40V, Positive-QTOFsplash10-014j-1910000000-dbecc05d29e924e0b5352021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Demethoxycurcumin 10V, Negative-QTOFsplash10-014i-0952000000-238d293f45f85e124a772021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Demethoxycurcumin 20V, Negative-QTOFsplash10-014r-0913000000-2bcebdb0a036193118c72021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Demethoxycurcumin 40V, Negative-QTOFsplash10-014r-0912000000-46bf9193d3b8351d35052021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound ID714
FooDB IDFDB011964
KNApSAcK IDC00033297
Chemspider ID4579941
KEGG Compound IDNot Available
BioCyc IDCPD-12187
BiGG IDNot Available
Wikipedia LinkDesmethoxycurcumin
METLIN IDNot Available
PubChem Compound5469424
PDB IDNot Available
ChEBI ID65737
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1486801
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Villaflores OB, Chen YJ, Chen CP, Yeh JM, Wu TY: Effects of curcumin and demethoxycurcumin on amyloid-beta precursor and tau proteins through the internal ribosome entry sites: a potential therapeutic for Alzheimer's disease. Taiwan J Obstet Gynecol. 2012 Dec;51(4):554-64. doi: 10.1016/j.tjog.2012.09.010. [PubMed:23276558 ]
  2. Chaneiam N, Changtam C, Mungkongdee T, Suthatvoravut U, Winichagoon P, Vadolas J, Suksamrarn A, Fucharoen S, Svasti S: A reduced curcuminoid analog as a novel inducer of fetal hemoglobin. Ann Hematol. 2013 Mar;92(3):379-86. doi: 10.1007/s00277-012-1604-1. Epub 2012 Oct 19. [PubMed:23079892 ]
  3. Jitoe-Masuda A, Fujimoto A, Masuda T: Curcumin: from chemistry to chemistry-based functions. Curr Pharm Des. 2013;19(11):2084-92. [PubMed:23116314 ]
  4. Villaflores OB, Chen YJ, Chen CP, Yeh JM, Wu TY: Curcuminoids and resveratrol as anti-Alzheimer agents. Taiwan J Obstet Gynecol. 2012 Dec;51(4):515-25. doi: 10.1016/j.tjog.2012.09.005. [PubMed:23276553 ]
  5. Jantan I, Saputri FC, Qaisar MN, Buang F: Correlation between Chemical Composition of Curcuma domestica and Curcuma xanthorrhiza and Their Antioxidant Effect on Human Low-Density Lipoprotein Oxidation. Evid Based Complement Alternat Med. 2012;2012:438356. doi: 10.1155/2012/438356. Epub 2012 Nov 26. [PubMed:23243446 ]
  6. Kumar A, Bora U: Molecular docking studies on inhibition of Stat3 dimerization by curcumin natural derivatives and its conjugates with amino acids. Bioinformation. 2012;8(20):988-93. doi: 10.6026/97320630008988. Epub 2012 Oct 13. [PubMed:23275693 ]
  7. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .