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Showing Compound (±)-3',4'-Methylenedioxy-5,7-dimethylepicatechin (FDB017127)

Record Information
Version1.0
Creation date2010-04-08 22:12:51 UTC
Update date2019-11-26 03:14:15 UTC
Primary IDFDB017127
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(±)-3',4'-Methylenedioxy-5,7-dimethylepicatechin
Description(±)-3',4'-Methylenedioxy-5,7-dimethylepicatechin 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 (±)-3',4'-Methylenedioxy-5,7-dimethylepicatechin has been detected, but not quantified in, chinese cinnamons (Cinnamomum aromaticum) and herbs and spices. This could make (±)-3',4'-methylenedioxy-5,7-dimethylepicatechin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (±)-3',4'-Methylenedioxy-5,7-dimethylepicatechin.
CAS Number87562-72-9
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
3',4'-Methylenedioxy epicatechin 5,7-dimethyl etherHMDB
(±)-3',4'-Methylenedioxy-5,7-dimethylepicatechinmanual
Predicted Properties
PropertyValueSource
Water Solubility0.21 g/LALOGPS
logP2.36ALOGPS
logP2.32ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)13.87ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area66.38 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity84.77 m³·mol⁻¹ChemAxon
Polarizability33.97 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC18H18O6
IUPAC name2-(2H-1,3-benzodioxol-5-yl)-5,7-dimethoxy-3,4-dihydro-2H-1-benzopyran-3-ol
InChI IdentifierInChI=1S/C18H18O6/c1-20-11-6-15(21-2)12-8-13(19)18(24-16(12)7-11)10-3-4-14-17(5-10)23-9-22-14/h3-7,13,18-19H,8-9H2,1-2H3
InChI KeyMMKQEVQTCAAXTI-UHFFFAOYSA-N
Isomeric SMILESCOC1=CC(OC)=C2CC(O)C(OC2=C1)C1=CC2=C(OCO2)C=C1
Average Molecular Weight330.3319
Monoisotopic Molecular Weight330.110338308
Classification
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
  • 5-methoxyflavonoid-skeleton
  • 7-methoxyflavonoid-skeleton
  • 3-hydroxyflavonoid
  • Hydroxyflavonoid
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Benzodioxole
  • Anisole
  • Alkyl aryl ether
  • Benzenoid
  • Secondary alcohol
  • Ether
  • Organoheterocyclic compound
  • Acetal
  • Oxacycle
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Alcohol
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 65.45%; H 5.49%; O 29.06%DFC
Melting PointMp 162-164°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D -39.3 (c, 0.84 in CHCl3)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS(±)-3',4'-Methylenedioxy-5,7-dimethylepicatechin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0wmr-0938000000-5468ff40061503bad51aSpectrum
Predicted GC-MS(±)-3',4'-Methylenedioxy-5,7-dimethylepicatechin, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0079-6209000000-5f0c83745d63bbe18004Spectrum
Predicted GC-MS(±)-3',4'-Methylenedioxy-5,7-dimethylepicatechin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(±)-3',4'-Methylenedioxy-5,7-dimethylepicatechin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0319000000-121b6cc518c4b96ee61dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0912000000-3ad8568c3df9e2d3b2e6Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f79-1930000000-28431dd5924e742350adSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0119000000-41fbe2446264fcb7fdbbSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0400-0924000000-1ab90f749d28732d3aadSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0079-2910000000-efc32488c35eeee88117Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009000000-4ca52439b731e1c3fd61Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ta-0269000000-656500212d771efc7e8fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01q1-1291000000-ae986023a6a433789bfcSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0009000000-3b03c1331c05e6f857d3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0908000000-ab3d3a34a917d2d47af3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kr-1931000000-358545b4e78aeba1c6b9Spectrum
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 IDHMDB37955
CRC / DFC (Dictionary of Food Compounds) IDCML31-M:KWF81-Z
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00008829
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 / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.