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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-02-23 11:07:11 UTC
Update Date2021-09-14 15:00:08 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 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.
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
Physiological effect

Adverse health effect

Disposition

Biological location

Source

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-MetCCS_train_neg135.00130932474
[M-H]-Not Available137.0http://allccs.zhulab.cn/database/detail?ID=AllCCS00000299
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+143.0331661259
DarkChem[M-H]-135.96131661259
AllCCS[M+H]+140.36332859911
AllCCS[M-H]-135.0432859911
DeepCCS[M+H]+134.62730932474
DeepCCS[M-H]-132.00530932474
DeepCCS[M-2H]-167.80830932474
DeepCCS[M+Na]+142.80330932474
AllCCS[M+H]+140.432859911
AllCCS[M+H-H2O]+136.132859911
AllCCS[M+NH4]+144.332859911
AllCCS[M+Na]+145.432859911
AllCCS[M-H]-135.032859911
AllCCS[M+Na-2H]-135.832859911
AllCCS[M+HCOO]-136.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3,4-Dihydroxymandelic acidOC(C(O)=O)C1=CC=C(O)C(O)=C13487.5Standard polar33892256
3,4-Dihydroxymandelic acidOC(C(O)=O)C1=CC=C(O)C(O)=C11843.0Standard non polar33892256
3,4-Dihydroxymandelic acidOC(C(O)=O)C1=CC=C(O)C(O)=C11712.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3,4-Dihydroxymandelic acid,1TMS,isomer #1C[Si](C)(C)OC(C(=O)O)C1=CC=C(O)C(O)=C11949.0Semi standard non polar33892256
3,4-Dihydroxymandelic acid,1TMS,isomer #2C[Si](C)(C)OC(=O)C(O)C1=CC=C(O)C(O)=C11952.2Semi standard non polar33892256
3,4-Dihydroxymandelic acid,1TMS,isomer #3C[Si](C)(C)OC1=CC=C(C(O)C(=O)O)C=C1O1860.5Semi standard non polar33892256
3,4-Dihydroxymandelic acid,1TMS,isomer #4C[Si](C)(C)OC1=CC(C(O)C(=O)O)=CC=C1O1868.2Semi standard non polar33892256
3,4-Dihydroxymandelic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)C(O[Si](C)(C)C)C1=CC=C(O)C(O)=C11926.7Semi standard non polar33892256
3,4-Dihydroxymandelic acid,2TMS,isomer #2C[Si](C)(C)OC1=CC=C(C(O[Si](C)(C)C)C(=O)O)C=C1O1882.1Semi standard non polar33892256
3,4-Dihydroxymandelic acid,2TMS,isomer #3C[Si](C)(C)OC1=CC(C(O[Si](C)(C)C)C(=O)O)=CC=C1O1899.3Semi standard non polar33892256
3,4-Dihydroxymandelic acid,2TMS,isomer #4C[Si](C)(C)OC(=O)C(O)C1=CC=C(O[Si](C)(C)C)C(O)=C11864.7Semi standard non polar33892256
3,4-Dihydroxymandelic acid,2TMS,isomer #5C[Si](C)(C)OC(=O)C(O)C1=CC=C(O)C(O[Si](C)(C)C)=C11849.5Semi standard non polar33892256
3,4-Dihydroxymandelic acid,2TMS,isomer #6C[Si](C)(C)OC1=CC=C(C(O)C(=O)O)C=C1O[Si](C)(C)C1864.6Semi standard non polar33892256
3,4-Dihydroxymandelic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)C(O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C(O)=C11903.1Semi standard non polar33892256
3,4-Dihydroxymandelic acid,3TMS,isomer #2C[Si](C)(C)OC(=O)C(O[Si](C)(C)C)C1=CC=C(O)C(O[Si](C)(C)C)=C11903.5Semi standard non polar33892256
3,4-Dihydroxymandelic acid,3TMS,isomer #3C[Si](C)(C)OC1=CC=C(C(O[Si](C)(C)C)C(=O)O)C=C1O[Si](C)(C)C1900.4Semi standard non polar33892256
3,4-Dihydroxymandelic acid,3TMS,isomer #4C[Si](C)(C)OC(=O)C(O)C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C11905.2Semi standard non polar33892256
3,4-Dihydroxymandelic acid,4TMS,isomer #1C[Si](C)(C)OC(=O)C(O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C11941.3Semi standard non polar33892256
3,4-Dihydroxymandelic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(C(=O)O)C1=CC=C(O)C(O)=C12215.3Semi standard non polar33892256
3,4-Dihydroxymandelic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C(O)C1=CC=C(O)C(O)=C12202.2Semi standard non polar33892256
3,4-Dihydroxymandelic acid,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C(C(O)C(=O)O)C=C1O2143.9Semi standard non polar33892256
3,4-Dihydroxymandelic acid,1TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1=CC(C(O)C(=O)O)=CC=C1O2133.4Semi standard non polar33892256
3,4-Dihydroxymandelic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(O[Si](C)(C)C(C)(C)C)C1=CC=C(O)C(O)=C12396.9Semi standard non polar33892256
3,4-Dihydroxymandelic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C(C(O[Si](C)(C)C(C)(C)C)C(=O)O)C=C1O2400.0Semi standard non polar33892256
3,4-Dihydroxymandelic acid,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC(C(O[Si](C)(C)C(C)(C)C)C(=O)O)=CC=C1O2406.2Semi standard non polar33892256
3,4-Dihydroxymandelic acid,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=O)C(O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C12370.8Semi standard non polar33892256
3,4-Dihydroxymandelic acid,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC(=O)C(O)C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C12345.9Semi standard non polar33892256
3,4-Dihydroxymandelic acid,2TBDMS,isomer #6CC(C)(C)[Si](C)(C)OC1=CC=C(C(O)C(=O)O)C=C1O[Si](C)(C)C(C)(C)C2387.9Semi standard non polar33892256
3,4-Dihydroxymandelic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C12565.3Semi standard non polar33892256
3,4-Dihydroxymandelic acid,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C(O[Si](C)(C)C(C)(C)C)C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C12567.3Semi standard non polar33892256
3,4-Dihydroxymandelic acid,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C(C(O[Si](C)(C)C(C)(C)C)C(=O)O)C=C1O[Si](C)(C)C(C)(C)C2595.9Semi standard non polar33892256
3,4-Dihydroxymandelic acid,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=O)C(O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C12609.6Semi standard non polar33892256
3,4-Dihydroxymandelic acid,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C12774.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 3,4-Dihydroxymandelic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0a4i-0629000000-ae329bc0399bdead30ee2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3,4-Dihydroxymandelic acid GC-MS (4 TMS)splash10-0a4i-1679200000-30b0a470753b8a534ffb2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3,4-Dihydroxymandelic acid GC-EI-TOF (Non-derivatized)splash10-0a4i-0629000000-ae329bc0399bdead30ee2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3,4-Dihydroxymandelic acid GC-MS (Non-derivatized)splash10-0a4i-1679200000-30b0a470753b8a534ffb2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3,4-Dihydroxymandelic acid GC-EI-TOF (Non-derivatized)splash10-0a4i-0938000000-048f9a7dbf493cb105d02017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-Dihydroxymandelic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-06rl-2900000000-45a24bed7c390b0517a92017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-Dihydroxymandelic acid GC-MS (4 TMS) - 70eV, Positivesplash10-0a4i-1009100000-2a01ecfd802a6d86fff72017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-Dihydroxymandelic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dihydroxymandelic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-01qi-1900000000-54c118704077cc354da72012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dihydroxymandelic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-03k9-5900000000-ef520e550b3f5cce89d42012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dihydroxymandelic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0a4l-7900000000-2c2914429bf7b73d4a332012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dihydroxymandelic acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOFsplash10-001i-0900000000-80a2a015caa693fb0bdb2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dihydroxymandelic acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOFsplash10-000i-0900000000-5d651845e3e03edc63dc2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dihydroxymandelic acid LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOFsplash10-000i-0900000000-5ed666462a4d020d9bad2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dihydroxymandelic acid LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOFsplash10-000i-1900000000-f785c36e33914dd6cfa02012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dihydroxymandelic acid LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOFsplash10-052r-3900000000-15fd25c25c09bb8789122012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dihydroxymandelic acid LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOFsplash10-0002-9400000000-42f34c3c13cd670ff16f2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dihydroxymandelic acid LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOFsplash10-000i-0900000000-e0e14e382ffa485ebcfc2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dihydroxymandelic acid LC-ESI-QQ , negative-QTOFsplash10-001i-0900000000-80a2a015caa693fb0bdb2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dihydroxymandelic acid LC-ESI-QQ , negative-QTOFsplash10-000i-0900000000-717de91658e43f0217e42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dihydroxymandelic acid LC-ESI-QQ , negative-QTOFsplash10-000i-0900000000-5ed666462a4d020d9bad2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dihydroxymandelic acid LC-ESI-QQ , negative-QTOFsplash10-000i-1900000000-f7a0f4c346c5c2d4669f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dihydroxymandelic acid LC-ESI-QQ , negative-QTOFsplash10-052r-3900000000-15fd25c25c09bb8789122017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dihydroxymandelic acid LC-ESI-QTOF , negative-QTOFsplash10-000i-0900000000-e0e14e382ffa485ebcfc2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dihydroxymandelic acid , negative-QTOFsplash10-00kr-0900000000-bd002360ad3147f32bdb2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dihydroxymandelic acid LC-ESI-QTOF , positive-QTOFsplash10-0002-9400000000-42f34c3c13cd670ff16f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dihydroxymandelic acid 20V, Negative-QTOFsplash10-000i-0900000000-1b8bb3963db8dbdf68b72021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxymandelic acid 10V, Positive-QTOFsplash10-00kr-0900000000-adc00447f61ba09ff2b92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxymandelic acid 20V, Positive-QTOFsplash10-000i-0900000000-c3215810f102f9a6bcd52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxymandelic acid 40V, Positive-QTOFsplash10-0r7i-7900000000-d9fef758451d2742cf582017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxymandelic acid 10V, Negative-QTOFsplash10-001r-0900000000-6ac7602cc5f3af7016622017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxymandelic acid 20V, Negative-QTOFsplash10-0apr-0900000000-b6bce5b5e83f1dd663a72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxymandelic acid 40V, Negative-QTOFsplash10-0a4i-2900000000-dfbd957390c0796149632017-09-01Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
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 IDNot Available
Good Scents IDNot Available
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. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]

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