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Showing Compound 3-Methoxy-4-hydroxyphenylglycolaldehyde (FDB023294)

Record Information
Version1.0
Creation date2011-09-21 00:27:38 UTC
Update date2019-11-26 03:21:08 UTC
Primary IDFDB023294
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name3-Methoxy-4-hydroxyphenylglycolaldehyde
Description3-Methoxy-4-hydroxyphenylglycolaldehyde is the monoamine oxidase (MAO) aldehyde metabolite of metanephrine. Metanephrine is an O-methylated metabolite formed by catechol-O-methyltransferase (COMT) from epinephrine. Catecholamines play an important role in platelet activation and aggregation, epinephrine being the most potent one. Catecholamines are substantially increased during stress, exercise or smoking and could result in clinically important platelet activation if their action was not rapidly regulated. The inhibitory effects of methoxy phenolic derivatives on epinephrine-induced platelet aggregation may possibly be attributed to their free radical scavenging properties. There is substantial evidence to conclude that an internal rapid autoregulation of epinephrine-induced platelet aggregation, caused by its metabolic degradation products, takes place in vivo. (PMID: 11958479, 9706478) [HMDB]. 3-Methoxy-4-hydroxyphenylglycolaldehyde is found in many foods, some of which are nutmeg, peach (variety), common oregano, and olive.
CAS Number17592-23-3
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
4-Hydroxy-3-methoxy mandelaldehydeHMDB
4-Hydroxy-3-methoxymandelaldehydeHMDB
4-Hydroxy-3-methoxyphenylglycolaldehydeHMDB
a,4-Dihydroxy-3-methoxy-benzeneacetaldehydeHMDB
4-hydroxy-3-methoxy Mandelaldehydehmdb
a,4-dihydroxy-3-methoxy-Benzeneacetaldehydehmdb
Predicted Properties
PropertyValueSource
Water Solubility5.13 g/LALOGPS
logP0.49ALOGPS
logP0.28ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)9.9ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity46.22 m³·mol⁻¹ChemAxon
Polarizability17.67 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC9H10O4
IUPAC name2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetaldehyde
InChI IdentifierInChI=1S/C9H10O4/c1-13-9-4-6(8(12)5-10)2-3-7(9)11/h2-5,8,11-12H,1H3
InChI KeyVISAJVAPYPFKCL-UHFFFAOYSA-N
Isomeric SMILESCOC1=C(O)C=CC(=C1)C(O)C=O
Average Molecular Weight182.1733
Monoisotopic Molecular Weight182.057908808
Classification
Description Belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassMethoxyphenols
Direct ParentMethoxyphenols
Alternative Parents
Substituents
  • Methoxyphenol
  • Phenylacetaldehyde
  • Anisole
  • Phenoxy compound
  • Phenol ether
  • Methoxybenzene
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Alpha-hydroxyaldehyde
  • Secondary alcohol
  • Ether
  • Aromatic alcohol
  • Organooxygen compound
  • Aldehyde
  • Carbonyl group
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS3-Methoxy-4-hydroxyphenylglycolaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0udi-2900000000-c3b751a80e98556beecdSpectrum
Predicted GC-MS3-Methoxy-4-hydroxyphenylglycolaldehyde, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-5193000000-6e22ae7f509439b91a97Spectrum
Predicted GC-MS3-Methoxy-4-hydroxyphenylglycolaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Methoxy-4-hydroxyphenylglycolaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-241e0f5c9b5867f24f802017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fsi-0900000000-ad05d32557d49f4e68532017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0abj-6900000000-3b0305c2b5932c3966b52017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-6784d8af6231fa2706032017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0kn9-0900000000-8395d2966f8d730d3dd32017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-7900000000-348d28ad54efde88e76b2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-e0b0d2106fad76afa1fe2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pi3-3900000000-cdf305b3288279dea0a12021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-5900000000-4c8fbae5388a3e0a51002021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0900000000-656cb77ee0208456f90b2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dl-4900000000-e5c44a99eda118e291d32021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fj3-9500000000-b4df271139281b8e52ff2021-09-22View Spectrum
NMRNot Available
ChemSpider ID389601
ChEMBL IDNot Available
KEGG Compound IDC05583
Pubchem Compound ID440729
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB04061
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID46069
KNApSAcK IDNot Available
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
Pathways
NameSMPDB LinkKEGG Link
Tyrosine MetabolismSMP00006 map00350
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference