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Showing Compound 3,4-dihydroxymandelate (FDB030383)

Record Information
Version1.0
Creation date2015-05-07 19:09:00 UTC
Update date2025-11-19 03:01:05 UTC
Primary IDFDB030383
Secondary Accession Numbers
  • FDB022719
Chemical Information
FooDB Name3,4-dihydroxymandelate
Description3,4-dihydroxymandelic acid, also known as 3,4-dihydroxyphenylglycolate or (3,4-dihydroxyphenyl)(hydroxy)acetic acid, is a member of the class of compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety. 3,4-dihydroxymandelic acid is soluble (in water) and a moderately acidic compound (based on its pKa). 3,4-dihydroxymandelic acid can be found in a number of food items such as lime, pitanga, sapodilla, and persimmon, which makes 3,4-dihydroxymandelic acid a potential biomarker for the consumption of these food products. 3,4-dihydroxymandelic acid can be found primarily in blood and urine, as well as in human nerve cells tissue. In humans, 3,4-dihydroxymandelic acid is involved in a couple of metabolic pathways, which include disulfiram action pathway and tyrosine metabolism. 3,4-dihydroxymandelic acid is also involved in several metabolic disorders, some of which include hawkinsinuria, alkaptonuria, dopamine beta-hydroxylase deficiency, and tyrosinemia, transient, of the newborn.
CAS Number775-01-9
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(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
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
Chemical FormulaC8H8O5
IUPAC name2-(3,4-dihydroxyphenyl)-2-hydroxyacetic acid
InChI IdentifierInChI=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
Isomeric SMILESOC(C(O)=O)C1=CC=C(O)C(O)=C1
Average Molecular Weight184.1461
Monoisotopic Molecular Weight184.037173366
Classification
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:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
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
GC-MS3,4-Dihydroxymandelic acid, non-derivatized, GC-MS Spectrumsplash10-0a4i-0629000000-ae329bc0399bdead30eeSpectrum
GC-MS3,4-Dihydroxymandelic acid, 4 TMS, GC-MS Spectrumsplash10-0a4i-1679200000-30b0a470753b8a534ffbSpectrum
GC-MS3,4-Dihydroxymandelic acid, non-derivatized, GC-MS Spectrumsplash10-0a4i-0629000000-ae329bc0399bdead30eeSpectrum
GC-MS3,4-Dihydroxymandelic acid, non-derivatized, GC-MS Spectrumsplash10-0a4i-1679200000-30b0a470753b8a534ffbSpectrum
GC-MS3,4-Dihydroxymandelic acid, non-derivatized, GC-MS Spectrumsplash10-0a4i-0938000000-048f9a7dbf493cb105d0Spectrum
Predicted GC-MS3,4-Dihydroxymandelic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-06rl-2900000000-45a24bed7c390b0517a9Spectrum
Predicted GC-MS3,4-Dihydroxymandelic acid, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-1009100000-2a01ecfd802a6d86fff7Spectrum
Predicted GC-MS3,4-Dihydroxymandelic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-01qi-1900000000-54c118704077cc354da72012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-03k9-5900000000-ef520e550b3f5cce89d42012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0a4l-7900000000-2c2914429bf7b73d4a332012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-001i-0900000000-80a2a015caa693fb0bdb2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-000i-0900000000-5d651845e3e03edc63dc2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-000i-0900000000-5ed666462a4d020d9bad2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-000i-1900000000-f785c36e33914dd6cfa02012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-052r-3900000000-15fd25c25c09bb8789122012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0002-9400000000-42f34c3c13cd670ff16f2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-000i-0900000000-e0e14e382ffa485ebcfc2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-0900000000-80a2a015caa693fb0bdb2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-0900000000-717de91658e43f0217e42017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-0900000000-5ed666462a4d020d9bad2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-1900000000-f7a0f4c346c5c2d4669f2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-052r-3900000000-15fd25c25c09bb8789122017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-000i-0900000000-e0e14e382ffa485ebcfc2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-00kr-0900000000-bd002360ad3147f32bdb2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0002-9400000000-42f34c3c13cd670ff16f2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-1b8bb3963db8dbdf68b72021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0900000000-adc00447f61ba09ff2b92017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-c3215810f102f9a6bcd52017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0r7i-7900000000-d9fef758451d2742cf582017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001r-0900000000-6ac7602cc5f3af7016622017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0apr-0900000000-b6bce5b5e83f1dd663a72017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-2900000000-dfbd957390c0796149632017-09-01View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider ID77371
ChEMBL IDNot Available
KEGG Compound IDC05580
Pubchem Compound ID85782
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB0001866
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia ID3,4-Dihydroxymandelic_acid
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