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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-08-13 10:08:18 UTC
Update Date2021-09-14 14:57:09 UTC
HMDB IDHMDB0004061
Secondary Accession Numbers
  • HMDB0006776
  • HMDB04061
  • HMDB06776
Metabolite Identification
Common Name3-Methoxy-4-hydroxyphenylglycolaldehyde
Description3-Methoxy-4-hydroxyphenylglycolaldehyde, also known as 4-hydroxy-3-methoxy mandelaldehyde, 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. 3-Methoxy-4-hydroxyphenylglycolaldehyde is an extremely weak basic (essentially neutral) compound (based on its pKa). 3-Methoxy-4-hydroxyphenylglycolaldehyde is the monoamine oxidase (MAO) aldehyde metabolite of metanephrine. 3-Methoxy-4-hydroxyphenylglycolaldehyde exists in all living organisms, ranging from bacteria to humans. Within humans, 3-methoxy-4-hydroxyphenylglycolaldehyde participates in a number of enzymatic reactions. In particular, 3-methoxy-4-hydroxyphenylglycolaldehyde can be biosynthesized from normetanephrine; which is mediated by the enzyme amine oxidase [flavin-containing] a. In addition, 3-methoxy-4-hydroxyphenylglycolaldehyde can be biosynthesized from metanephrine through the action of the enzyme amine oxidase [flavin-containing] a. Metanephrine is an O-methylated metabolite formed by catechol-O-methyltransferase (COMT) from epinephrine. In humans, 3-methoxy-4-hydroxyphenylglycolaldehyde is involved in the metabolic disorder called the monoamine oxidase-a deficiency (mao-a) pathway. Outside of the human body, 3-Methoxy-4-hydroxyphenylglycolaldehyde has been detected, but not quantified in, several different foods, such as chervils, kai-lans, calabash, custard apples, and tea. This could make 3-methoxy-4-hydroxyphenylglycolaldehyde a potential biomarker for the consumption of these foods. Catecholamines are substantially increased during stress, exercise or smoking and could result in clinically important platelet activation if their action was not rapidly regulated. Catecholamines play an important role in platelet activation and aggregation, epinephrine being the most potent one. 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.
Structure
Data?1582752296
Synonyms
ValueSource
4-Hydroxy-3-methoxy mandelaldehydeHMDB
4-Hydroxy-3-methoxymandelaldehydeHMDB
4-Hydroxy-3-methoxyphenylglycolaldehydeHMDB
a,4-Dihydroxy-3-methoxy-benzeneacetaldehydeHMDB
Chemical FormulaC9H10O4
Average Molecular Weight182.1733
Monoisotopic Molecular Weight182.057908808
IUPAC Name2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetaldehyde
Traditional Name2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetaldehyde
CAS Registry Number17592-23-3
SMILES
COC1=C(O)C=CC(=C1)C(O)C=O
InChI Identifier
InChI=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
Chemical Taxonomy
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
Physiological effect

Adverse health effect

Disposition

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP0.517Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility5.13 g/LALOGPS
logP10(0.49) g/LALOGPS
logP10(0.28) g/LChemAxon
logS10(-1.6) g/LALOGPS
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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+140.65731661259
DarkChem[M-H]-138.39931661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-Methoxy-4-hydroxyphenylglycolaldehydeCOC1=C(O)C=CC(=C1)C(O)C=O3004.7Standard polar33892256
3-Methoxy-4-hydroxyphenylglycolaldehydeCOC1=C(O)C=CC(=C1)C(O)C=O1589.9Standard non polar33892256
3-Methoxy-4-hydroxyphenylglycolaldehydeCOC1=C(O)C=CC(=C1)C(O)C=O1592.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-Methoxy-4-hydroxyphenylglycolaldehyde,1TMS,isomer #1COC1=CC(C(O)C=O)=CC=C1O[Si](C)(C)C1728.2Semi standard non polar33892256
3-Methoxy-4-hydroxyphenylglycolaldehyde,1TMS,isomer #2COC1=CC(C(C=O)O[Si](C)(C)C)=CC=C1O1748.8Semi standard non polar33892256
3-Methoxy-4-hydroxyphenylglycolaldehyde,1TMS,isomer #3COC1=CC(C(O)=CO[Si](C)(C)C)=CC=C1O1901.8Semi standard non polar33892256
3-Methoxy-4-hydroxyphenylglycolaldehyde,2TMS,isomer #1COC1=CC(C(C=O)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C1787.7Semi standard non polar33892256
3-Methoxy-4-hydroxyphenylglycolaldehyde,2TMS,isomer #2COC1=CC(C(O)=CO[Si](C)(C)C)=CC=C1O[Si](C)(C)C1936.9Semi standard non polar33892256
3-Methoxy-4-hydroxyphenylglycolaldehyde,2TMS,isomer #3COC1=CC(C(=CO[Si](C)(C)C)O[Si](C)(C)C)=CC=C1O1995.0Semi standard non polar33892256
3-Methoxy-4-hydroxyphenylglycolaldehyde,3TMS,isomer #1COC1=CC(C(=CO[Si](C)(C)C)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C2022.3Semi standard non polar33892256
3-Methoxy-4-hydroxyphenylglycolaldehyde,3TMS,isomer #1COC1=CC(C(=CO[Si](C)(C)C)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C1965.8Standard non polar33892256
3-Methoxy-4-hydroxyphenylglycolaldehyde,3TMS,isomer #1COC1=CC(C(=CO[Si](C)(C)C)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C2133.8Standard polar33892256
3-Methoxy-4-hydroxyphenylglycolaldehyde,1TBDMS,isomer #1COC1=CC(C(O)C=O)=CC=C1O[Si](C)(C)C(C)(C)C1978.9Semi standard non polar33892256
3-Methoxy-4-hydroxyphenylglycolaldehyde,1TBDMS,isomer #2COC1=CC(C(C=O)O[Si](C)(C)C(C)(C)C)=CC=C1O2001.6Semi standard non polar33892256
3-Methoxy-4-hydroxyphenylglycolaldehyde,1TBDMS,isomer #3COC1=CC(C(O)=CO[Si](C)(C)C(C)(C)C)=CC=C1O2169.5Semi standard non polar33892256
3-Methoxy-4-hydroxyphenylglycolaldehyde,2TBDMS,isomer #1COC1=CC(C(C=O)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C2280.1Semi standard non polar33892256
3-Methoxy-4-hydroxyphenylglycolaldehyde,2TBDMS,isomer #2COC1=CC(C(O)=CO[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C2466.3Semi standard non polar33892256
3-Methoxy-4-hydroxyphenylglycolaldehyde,2TBDMS,isomer #3COC1=CC(C(=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=CC=C1O2496.0Semi standard non polar33892256
3-Methoxy-4-hydroxyphenylglycolaldehyde,3TBDMS,isomer #1COC1=CC(C(=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C2735.0Semi standard non polar33892256
3-Methoxy-4-hydroxyphenylglycolaldehyde,3TBDMS,isomer #1COC1=CC(C(=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C2617.0Standard non polar33892256
3-Methoxy-4-hydroxyphenylglycolaldehyde,3TBDMS,isomer #1COC1=CC(C(=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C2475.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3-Methoxy-4-hydroxyphenylglycolaldehyde GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-2900000000-c3b751a80e98556beecd2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Methoxy-4-hydroxyphenylglycolaldehyde GC-MS (2 TMS) - 70eV, Positivesplash10-00di-5193000000-6e22ae7f509439b91a972017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Methoxy-4-hydroxyphenylglycolaldehyde GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Methoxy-4-hydroxyphenylglycolaldehyde 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 - 3-Methoxy-4-hydroxyphenylglycolaldehyde 10V, Positive-QTOFsplash10-001i-0900000000-241e0f5c9b5867f24f802017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methoxy-4-hydroxyphenylglycolaldehyde 20V, Positive-QTOFsplash10-0fsi-0900000000-ad05d32557d49f4e68532017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methoxy-4-hydroxyphenylglycolaldehyde 40V, Positive-QTOFsplash10-0abj-6900000000-3b0305c2b5932c3966b52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methoxy-4-hydroxyphenylglycolaldehyde 10V, Negative-QTOFsplash10-001i-0900000000-6784d8af6231fa2706032017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methoxy-4-hydroxyphenylglycolaldehyde 20V, Negative-QTOFsplash10-0kn9-0900000000-8395d2966f8d730d3dd32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methoxy-4-hydroxyphenylglycolaldehyde 40V, Negative-QTOFsplash10-0a4i-7900000000-348d28ad54efde88e76b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methoxy-4-hydroxyphenylglycolaldehyde 10V, Negative-QTOFsplash10-001i-0900000000-e0b0d2106fad76afa1fe2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methoxy-4-hydroxyphenylglycolaldehyde 20V, Negative-QTOFsplash10-0pi3-3900000000-cdf305b3288279dea0a12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methoxy-4-hydroxyphenylglycolaldehyde 40V, Negative-QTOFsplash10-056r-5900000000-4c8fbae5388a3e0a51002021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methoxy-4-hydroxyphenylglycolaldehyde 10V, Positive-QTOFsplash10-00kr-0900000000-656cb77ee0208456f90b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methoxy-4-hydroxyphenylglycolaldehyde 20V, Positive-QTOFsplash10-00dl-4900000000-e5c44a99eda118e291d32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methoxy-4-hydroxyphenylglycolaldehyde 40V, Positive-QTOFsplash10-0fj3-9500000000-b4df271139281b8e52ff2021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
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 IDFDB023294
KNApSAcK IDNot Available
Chemspider ID389601
KEGG Compound IDC05583
BioCyc IDNot Available
BiGG ID46069
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440729
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH ID3M4HPGA
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Kawamura M, Eisenhofer G, Kopin IJ, Kador PF, Lee YS, Fujisawa S, Sato S: Aldose reductase: an aldehyde scavenging enzyme in the intraneuronal metabolism of norepinephrine in human sympathetic ganglia. Auton Neurosci. 2002 Mar 18;96(2):131-9. [PubMed:11958479 ]
  2. Evangelou AM, Malamas MP, Vezyraki P, Karkabounas SC: Is epinephrine-induced platelet aggregation autoregulated by its metabolic degradation products in vivo? In Vivo. 1998 May-Jun;12(3):321-5. [PubMed:9706478 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOB preferentially degrades benzylamine and phenylethylamine.
Gene Name:
MAOB
Uniprot ID:
P27338
Molecular weight:
58762.475
Reactions
Normetanephrine + Water + Oxygen → 3-Methoxy-4-hydroxyphenylglycolaldehyde + Ammonia + Hydrogen peroxidedetails
Metanephrine + Water + Oxygen → 3-Methoxy-4-hydroxyphenylglycolaldehyde + Hydrogen peroxide + Methylaminedetails
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:
MAOA
Uniprot ID:
P21397
Molecular weight:
59681.27
Reactions
Normetanephrine + Water + Oxygen → 3-Methoxy-4-hydroxyphenylglycolaldehyde + Ammonia + Hydrogen peroxidedetails
Metanephrine + Water + Oxygen → 3-Methoxy-4-hydroxyphenylglycolaldehyde + Hydrogen peroxide + Methylaminedetails
General function:
Involved in oxidoreductase activity
Specific function:
ALDHs play a major role in the detoxification of alcohol-derived acetaldehyde. They are involved in the metabolism of corticosteroids, biogenic amines, neurotransmitters, and lipid peroxidation. This protein preferentially oxidizes aromatic aldehyde substrates. It may play a role in the oxidation of toxic aldehydes.
Gene Name:
ALDH3A1
Uniprot ID:
P30838
Molecular weight:
50394.57
Reactions
3-Methoxy-4-hydroxyphenylglycolaldehyde + NAD + Water → Vanillylmandelic acid + NADH + Hydrogen Iondetails
3-Methoxy-4-hydroxyphenylglycolaldehyde + NADP + Water → Vanillylmandelic acid + NADPH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Recognizes as substrates free retinal and cellular retinol-binding protein-bound retinal. Seems to be the key enzyme in the formation of an RA gradient along the dorso-ventral axis during the early eye development and also in the development of the olfactory system (By similarity).
Gene Name:
ALDH1A3
Uniprot ID:
P47895
Molecular weight:
56107.995
Reactions
3-Methoxy-4-hydroxyphenylglycolaldehyde + NAD + Water → Vanillylmandelic acid + NADH + Hydrogen Iondetails
3-Methoxy-4-hydroxyphenylglycolaldehyde + NADP + Water → Vanillylmandelic acid + NADPH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
ALDH3B2
Uniprot ID:
P48448
Molecular weight:
42623.62
Reactions
3-Methoxy-4-hydroxyphenylglycolaldehyde + NAD + Water → Vanillylmandelic acid + NADH + Hydrogen Iondetails
3-Methoxy-4-hydroxyphenylglycolaldehyde + NADP + Water → Vanillylmandelic acid + NADPH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Oxidizes medium and long chain saturated and unsaturated aldehydes. Metabolizes also benzaldehyde. Low activity towards acetaldehyde and 3,4-dihydroxyphenylacetaldehyde. May not metabolize short chain aldehydes. May use both NADP(+) and NAD(+) as cofactors. May have a protective role against the cytotoxicity induced by lipid peroxidation.
Gene Name:
ALDH3B1
Uniprot ID:
P43353
Molecular weight:
51839.245
Reactions
3-Methoxy-4-hydroxyphenylglycolaldehyde + NAD + Water → Vanillylmandelic acid + NADH + Hydrogen Iondetails
3-Methoxy-4-hydroxyphenylglycolaldehyde + NADP + Water → Vanillylmandelic acid + NADPH + Hydrogen Iondetails