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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:38:16 UTC
Update Date2022-03-07 02:52:38 UTC
HMDB IDHMDB0030662
Secondary Accession Numbers
  • HMDB30662
Metabolite Identification
Common Name4'-O-Methylcatechin
Description4'-O-Methylcatechin belongs to the class of organic compounds known as catechins. Catechins are compounds containing a catechin moiety, which is a 3,4-dihydro-2-chromene-3,5.7-tiol. 4'-O-Methylcatechin has been detected, but not quantified in, chinese cinnamons (Cinnamomum aromaticum) and herbs and spices. This could make 4'-O-methylcatechin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 4'-O-Methylcatechin.
Structure
Data?1563862019
Synonyms
ValueSource
3,3',5,7-Tetrahydroxy-4'-methoxyflavanHMDB
Catechin 4'-methyl etherHMDB
Chemical FormulaC16H16O6
Average Molecular Weight304.2946
Monoisotopic Molecular Weight304.094688244
IUPAC Name2-(3-hydroxy-4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
Traditional Name2-(3-hydroxy-4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
CAS Registry Number69912-75-0
SMILES
COC1=C(O)C=C(C=C1)C1OC2=CC(O)=CC(O)=C2CC1O
InChI Identifier
InChI=1S/C16H16O6/c1-21-14-3-2-8(4-12(14)19)16-13(20)7-10-11(18)5-9(17)6-15(10)22-16/h2-6,13,16-20H,7H2,1H3
InChI KeyZHDMPVIDHWJGTN-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as catechins. Catechins are compounds containing a catechin moiety, which is a 3,4-dihydro-2-chromene-3,5.7-Tiol.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavans
Direct ParentCatechins
Alternative Parents
Substituents
  • Catechin
  • 4p-methoxyflavonoid-skeleton
  • 3'-hydroxyflavonoid
  • 3-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Methoxyphenol
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Secondary alcohol
  • Ether
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point152 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.33 g/LALOGPS
logP1.31ALOGPS
logP1.94ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)9.27ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area99.38 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity78.48 m³·mol⁻¹ChemAxon
Polarizability30.29 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+171.59931661259
DarkChem[M-H]-173.72831661259
DeepCCS[M+H]+166.91830932474
DeepCCS[M-H]-164.5630932474
DeepCCS[M-2H]-198.34330932474
DeepCCS[M+Na]+173.5730932474
AllCCS[M+H]+172.432859911
AllCCS[M+H-H2O]+168.832859911
AllCCS[M+NH4]+175.732859911
AllCCS[M+Na]+176.632859911
AllCCS[M-H]-172.332859911
AllCCS[M+Na-2H]-171.932859911
AllCCS[M+HCOO]-171.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4'-O-MethylcatechinCOC1=C(O)C=C(C=C1)C1OC2=CC(O)=CC(O)=C2CC1O4591.8Standard polar33892256
4'-O-MethylcatechinCOC1=C(O)C=C(C=C1)C1OC2=CC(O)=CC(O)=C2CC1O2994.0Standard non polar33892256
4'-O-MethylcatechinCOC1=C(O)C=C(C=C1)C1OC2=CC(O)=CC(O)=C2CC1O3084.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4'-O-Methylcatechin,1TMS,isomer #1COC1=CC=C(C2OC3=CC(O)=CC(O)=C3CC2O)C=C1O[Si](C)(C)C3029.2Semi standard non polar33892256
4'-O-Methylcatechin,1TMS,isomer #2COC1=CC=C(C2OC3=CC(O[Si](C)(C)C)=CC(O)=C3CC2O)C=C1O3059.7Semi standard non polar33892256
4'-O-Methylcatechin,1TMS,isomer #3COC1=CC=C(C2OC3=CC(O)=CC(O[Si](C)(C)C)=C3CC2O)C=C1O3032.8Semi standard non polar33892256
4'-O-Methylcatechin,1TMS,isomer #4COC1=CC=C(C2OC3=CC(O)=CC(O)=C3CC2O[Si](C)(C)C)C=C1O3038.0Semi standard non polar33892256
4'-O-Methylcatechin,2TMS,isomer #1COC1=CC=C(C2OC3=CC(O[Si](C)(C)C)=CC(O)=C3CC2O)C=C1O[Si](C)(C)C2931.2Semi standard non polar33892256
4'-O-Methylcatechin,2TMS,isomer #2COC1=CC=C(C2OC3=CC(O)=CC(O[Si](C)(C)C)=C3CC2O)C=C1O[Si](C)(C)C2910.1Semi standard non polar33892256
4'-O-Methylcatechin,2TMS,isomer #3COC1=CC=C(C2OC3=CC(O)=CC(O)=C3CC2O[Si](C)(C)C)C=C1O[Si](C)(C)C2963.3Semi standard non polar33892256
4'-O-Methylcatechin,2TMS,isomer #4COC1=CC=C(C2OC3=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3CC2O)C=C1O2946.9Semi standard non polar33892256
4'-O-Methylcatechin,2TMS,isomer #5COC1=CC=C(C2OC3=CC(O[Si](C)(C)C)=CC(O)=C3CC2O[Si](C)(C)C)C=C1O2886.0Semi standard non polar33892256
4'-O-Methylcatechin,2TMS,isomer #6COC1=CC=C(C2OC3=CC(O)=CC(O[Si](C)(C)C)=C3CC2O[Si](C)(C)C)C=C1O2908.1Semi standard non polar33892256
4'-O-Methylcatechin,3TMS,isomer #1COC1=CC=C(C2OC3=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3CC2O)C=C1O[Si](C)(C)C2902.9Semi standard non polar33892256
4'-O-Methylcatechin,3TMS,isomer #2COC1=CC=C(C2OC3=CC(O[Si](C)(C)C)=CC(O)=C3CC2O[Si](C)(C)C)C=C1O[Si](C)(C)C2796.0Semi standard non polar33892256
4'-O-Methylcatechin,3TMS,isomer #3COC1=CC=C(C2OC3=CC(O)=CC(O[Si](C)(C)C)=C3CC2O[Si](C)(C)C)C=C1O[Si](C)(C)C2819.9Semi standard non polar33892256
4'-O-Methylcatechin,3TMS,isomer #4COC1=CC=C(C2OC3=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3CC2O[Si](C)(C)C)C=C1O2835.0Semi standard non polar33892256
4'-O-Methylcatechin,4TMS,isomer #1COC1=CC=C(C2OC3=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3CC2O[Si](C)(C)C)C=C1O[Si](C)(C)C2825.6Semi standard non polar33892256
4'-O-Methylcatechin,1TBDMS,isomer #1COC1=CC=C(C2OC3=CC(O)=CC(O)=C3CC2O)C=C1O[Si](C)(C)C(C)(C)C3327.7Semi standard non polar33892256
4'-O-Methylcatechin,1TBDMS,isomer #2COC1=CC=C(C2OC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C3CC2O)C=C1O3339.5Semi standard non polar33892256
4'-O-Methylcatechin,1TBDMS,isomer #3COC1=CC=C(C2OC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3CC2O)C=C1O3326.8Semi standard non polar33892256
4'-O-Methylcatechin,1TBDMS,isomer #4COC1=CC=C(C2OC3=CC(O)=CC(O)=C3CC2O[Si](C)(C)C(C)(C)C)C=C1O3361.3Semi standard non polar33892256
4'-O-Methylcatechin,2TBDMS,isomer #1COC1=CC=C(C2OC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C3CC2O)C=C1O[Si](C)(C)C(C)(C)C3463.6Semi standard non polar33892256
4'-O-Methylcatechin,2TBDMS,isomer #2COC1=CC=C(C2OC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3CC2O)C=C1O[Si](C)(C)C(C)(C)C3454.5Semi standard non polar33892256
4'-O-Methylcatechin,2TBDMS,isomer #3COC1=CC=C(C2OC3=CC(O)=CC(O)=C3CC2O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C3521.4Semi standard non polar33892256
4'-O-Methylcatechin,2TBDMS,isomer #4COC1=CC=C(C2OC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C3CC2O)C=C1O3483.5Semi standard non polar33892256
4'-O-Methylcatechin,2TBDMS,isomer #5COC1=CC=C(C2OC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C3CC2O[Si](C)(C)C(C)(C)C)C=C1O3456.8Semi standard non polar33892256
4'-O-Methylcatechin,2TBDMS,isomer #6COC1=CC=C(C2OC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3CC2O[Si](C)(C)C(C)(C)C)C=C1O3468.1Semi standard non polar33892256
4'-O-Methylcatechin,3TBDMS,isomer #1COC1=CC=C(C2OC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C3CC2O)C=C1O[Si](C)(C)C(C)(C)C3613.0Semi standard non polar33892256
4'-O-Methylcatechin,3TBDMS,isomer #2COC1=CC=C(C2OC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C3CC2O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C3550.3Semi standard non polar33892256
4'-O-Methylcatechin,3TBDMS,isomer #3COC1=CC=C(C2OC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3CC2O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C3556.5Semi standard non polar33892256
4'-O-Methylcatechin,3TBDMS,isomer #4COC1=CC=C(C2OC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C3CC2O[Si](C)(C)C(C)(C)C)C=C1O3562.8Semi standard non polar33892256
4'-O-Methylcatechin,4TBDMS,isomer #1COC1=CC=C(C2OC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C3CC2O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C3702.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4'-O-Methylcatechin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0079-0970000000-d27ddfc79073862dcd9c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4'-O-Methylcatechin GC-MS (4 TMS) - 70eV, Positivesplash10-004i-1300090000-ee3f296bbddc7aa5e4912017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4'-O-Methylcatechin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4'-O-Methylcatechin 10V, Negative-QTOFsplash10-0udi-0219000000-c9afcfda1946a83ecbc32015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4'-O-Methylcatechin 20V, Negative-QTOFsplash10-0fri-0932000000-a8aa8768d2a221093e1b2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4'-O-Methylcatechin 40V, Negative-QTOFsplash10-05g0-2910000000-5cae78f2b80b6ddf99d92015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4'-O-Methylcatechin 10V, Negative-QTOFsplash10-0udi-0009000000-04ccc09c7865adc860512021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4'-O-Methylcatechin 20V, Negative-QTOFsplash10-0f79-0793000000-e569d28f0ecd87ef4d372021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4'-O-Methylcatechin 40V, Negative-QTOFsplash10-0udr-1962000000-746f85e5bc0332b291422021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4'-O-Methylcatechin 10V, Positive-QTOFsplash10-0a4r-0539000000-934dd89af13464b3c7132015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4'-O-Methylcatechin 20V, Positive-QTOFsplash10-000i-0911000000-5c29468cb66a1f05cbb02015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4'-O-Methylcatechin 40V, Positive-QTOFsplash10-00di-3900000000-bd4ed88865f407f25d312015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4'-O-Methylcatechin 10V, Positive-QTOFsplash10-0a4i-0109000000-0458d0e451e6416bde7a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4'-O-Methylcatechin 20V, Positive-QTOFsplash10-052r-0923000000-f681b7ebcec09766aa022021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4'-O-Methylcatechin 40V, Positive-QTOFsplash10-000i-3960000000-4a5dd78638112937f07c2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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 IDNot Available
FooDB IDFDB002573
KNApSAcK IDC00008810
Chemspider ID13077666
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14332897
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
4'-O-Methylcatechin → 6-{[3,5-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
4'-O-Methylcatechin → 3,4,5-trihydroxy-6-[2-methoxy-5-(3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-2-yl)phenoxy]oxane-2-carboxylic aciddetails
General function:
sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:
SULT1A3
Uniprot ID:
P0DMM9
Molecular weight:
34195.96
Reactions
4'-O-Methylcatechin → [2-methoxy-5-(3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-2-yl)phenyl]oxidanesulfonic aciddetails