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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-02-23 11:07:11 UTC
Update Date2020-11-09 23:16:04 UTC
HMDB IDHMDB0001866
Secondary Accession Numbers
  • HMDB01866
Metabolite Identification
Common Name3,4-Dihydroxymandelic acid
Description3,4-Dihydroxymandelic acid, also known as DOMA or 3,4-dihydroxyphenylglycolate, belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety. 3,4-Dihydroxymandelic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). 3,4-Dihydroxymandelic acid exists in all living organisms, ranging from bacteria to humans. Within humans, 3,4-dihydroxymandelic acid participates in a number of enzymatic reactions. In particular, 3,4-dihydroxymandelic acid can be biosynthesized from 3,4-dihydroxymandelaldehyde through its interaction with the enzyme aldehyde dehydrogenase, dimeric nadp-preferring. In addition, 3,4-dihydroxymandelic acid and guaiacol can be converted into vanillylmandelic acid and pyrocatechol through the action of the enzyme catechol O-methyltransferase. In humans, 3,4-dihydroxymandelic acid is involved in the metabolic disorder called tyrosinemia type I. Outside of the human body, 3,4-Dihydroxymandelic acid has been detected, but not quantified in, several different foods, such as yellow wax beans, soy beans, pomegranates, cucurbita (gourd), and daikon radish. This could make 3,4-dihydroxymandelic acid a potential biomarker for the consumption of these foods.
Structure
Data?1582752213
Synonyms
ValueSource
(3,4-Dihydroxyphenyl)(hydroxy)acetic acidChEBI
3,4-DihydroxymandelateChEBI
3,4-Dihydroxyphenylglycolic acidChEBI
Dihydroxymandelic acidChEBI
DOMAChEBI
(3,4-Dihydroxyphenyl)(hydroxy)acetateGenerator
3,4-DihydroxyphenylglycolateGenerator
DihydroxymandelateGenerator
3,4 DihydroxymandelateHMDB
3,4 Dihydroxymandelic acidHMDB
3,4-Dihydroxymandelic acid, (S)-isomerHMDB
3,4-Dihydroxymandelic acid, ion(1-)HMDB
3,4-Dihydroxymandelic acid, monosodium saltHMDB
DHMAHMDB
3,4-Dihydroxymandelic acid, (+-)-isomerHMDB
Chemical FormulaC8H8O5
Average Molecular Weight184.1461
Monoisotopic Molecular Weight184.037173366
IUPAC Name2-(3,4-dihydroxyphenyl)-2-hydroxyacetic acid
Traditional Namedihydroxymandelic acid
CAS Registry Number775-01-9
SMILES
OC(C(O)=O)C1=CC=C(O)C(O)=C1
InChI Identifier
InChI=1S/C8H8O5/c9-5-2-1-4(3-6(5)10)7(11)8(12)13/h1-3,7,9-11H,(H,12,13)
InChI KeyRGHMISIYKIHAJW-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassBenzenediols
Direct ParentCatechols
Alternative Parents
Substituents
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alpha-hydroxy acid
  • Monocyclic benzene moiety
  • Hydroxy acid
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Organooxygen compound
  • Aromatic alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility10.7 g/LALOGPS
logP0.72ALOGPS
logP0.29ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)2.98ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity42.67 m³·mol⁻¹ChemAxon
Polarizability16.52 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0a4i-0629000000-ae329bc0399bdead30eeSpectrum
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-0a4i-1679200000-30b0a470753b8a534ffbSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4i-0629000000-ae329bc0399bdead30eeSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0a4i-1679200000-30b0a470753b8a534ffbSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4i-0938000000-048f9a7dbf493cb105d0Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-06rl-2900000000-45a24bed7c390b0517a9Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0a4i-1009100000-2a01ecfd802a6d86fff7Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-01qi-1900000000-54c118704077cc354da7Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-03k9-5900000000-ef520e550b3f5cce89d4Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0a4l-7900000000-2c2914429bf7b73d4a33Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-001i-0900000000-80a2a015caa693fb0bdbSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-000i-0900000000-5d651845e3e03edc63dcSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-000i-0900000000-5ed666462a4d020d9badSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-000i-1900000000-f785c36e33914dd6cfa0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-052r-3900000000-15fd25c25c09bb878912Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0002-9400000000-42f34c3c13cd670ff16fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-000i-0900000000-e0e14e382ffa485ebcfcSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-0900000000-80a2a015caa693fb0bdbSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-0900000000-717de91658e43f0217e4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-0900000000-5ed666462a4d020d9badSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-1900000000-f7a0f4c346c5c2d4669fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-052r-3900000000-15fd25c25c09bb878912Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-000i-0900000000-e0e14e382ffa485ebcfcSpectrum
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-00kr-0900000000-bd002360ad3147f32bdbSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0002-9400000000-42f34c3c13cd670ff16fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0900000000-adc00447f61ba09ff2b9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-c3215810f102f9a6bcd5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0r7i-7900000000-d9fef758451d2742cf58Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001r-0900000000-6ac7602cc5f3af701662Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0apr-0900000000-b6bce5b5e83f1dd663a7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-2900000000-dfbd957390c079614963Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Neuron
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.011 +/- 0.004 uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.12 +/- 0.05 umol/mmol creatinineAdult (>18 years old)MaleNormal
    • Geigy Scientific ...
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB030383
KNApSAcK IDNot Available
Chemspider ID77371
KEGG Compound IDC05580
BioCyc IDCPD-11879
BiGG ID46062
Wikipedia Link3,4-Dihydroxymandelic_acid
METLIN ID696
PubChem Compound85782
PDB IDNot Available
ChEBI ID27637
Food Biomarker OntologyNot Available
VMH ID34DHOXMAND
MarkerDB ID
References
Synthesis ReferenceJoray, Marcel; Breuninger, Manfred. Process for the preparation of phenolic compounds. PCT Int. Appl. (2007), 15pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. O'Meara A, Tormey W, FitzGerald RJ, Fitzgibbon M, Kenny D: Interpretation of random urinary catecholamines and their metabolites in neuroblastoma. Acta Paediatr. 1994 Jan;83(1):88-92. [PubMed:8193481 ]
  2. Eisenhofer G, Kopin IJ, Goldstein DS: Catecholamine metabolism: a contemporary view with implications for physiology and medicine. Pharmacol Rev. 2004 Sep;56(3):331-49. [PubMed:15317907 ]
  3. Zambotti F, Blau K, King GS, Campbell S, Sandler M: Monoamine metabolites and related compounds in human amniotic fluid: assay by gas chromatography and gas chromatography-mass spectrometry. Clin Chim Acta. 1975 Jun 20;61(3):247-56. [PubMed:1149252 ]
  4. Nohta H, Yamaguchi E, Ohkura Y, Watanabe H: Measurement of catecholamines, their precursor and metabolites in human urine and plasma by solid-phase extraction followed by high-performance liquid chromatography with fluorescence derivatization. J Chromatogr. 1989 Aug 25;493(1):15-26. [PubMed:2778005 ]
  5. Odink J, Korthals H, Knijff JH: Simultaneous determination of the major acidic metabolites of catecholamines and serotonin in urine by liquid chromatography with electrochemical detection after a one-step sample clean-up on Sephadex G-10; influence of vanilla and banana ingestion. J Chromatogr. 1988 Feb 26;424(2):273-83. [PubMed:2453525 ]
  6. Goldstein DS, Eisenhofer G, Kopin IJ: Sources and significance of plasma levels of catechols and their metabolites in humans. J Pharmacol Exp Ther. 2003 Jun;305(3):800-11. Epub 2003 Mar 20. [PubMed:12649306 ]

Enzymes

General function:
Involved in magnesium ion binding
Specific function:
Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOPA, alpha-methyl DOPA and isoproterenol.
Gene Name:
COMT
Uniprot ID:
P21964
Molecular weight:
30036.77
Reactions
S-Adenosylmethionine + 3,4-Dihydroxymandelic acid → S-Adenosylhomocysteine + Vanillylmandelic aciddetails
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
3,4-Dihydroxymandelaldehyde + NAD + Water → 3,4-Dihydroxymandelic acid + NADH + Hydrogen Iondetails
3,4-Dihydroxymandelaldehyde + NADP + Water → 3,4-Dihydroxymandelic 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
3,4-Dihydroxymandelaldehyde + NAD + Water → 3,4-Dihydroxymandelic acid + NADH + Hydrogen Iondetails
3,4-Dihydroxymandelaldehyde + NADP + Water → 3,4-Dihydroxymandelic 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
3,4-Dihydroxymandelaldehyde + NAD + Water → 3,4-Dihydroxymandelic acid + NADH + Hydrogen Iondetails
3,4-Dihydroxymandelaldehyde + NADP + Water → 3,4-Dihydroxymandelic 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
3,4-Dihydroxymandelaldehyde + NAD + Water → 3,4-Dihydroxymandelic acid + NADH + Hydrogen Iondetails
3,4-Dihydroxymandelaldehyde + NADP + Water → 3,4-Dihydroxymandelic acid + NADPH + Hydrogen Iondetails