Record Information
Version1.0
Creation date2015-05-07 19:09:00 UTC
Update date2019-11-26 03:21:43 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
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 - Experimental
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-1900000000-54c118704077cc354da7Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-03k9-5900000000-ef520e550b3f5cce89d4Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0a4l-7900000000-2c2914429bf7b73d4a33Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-001i-0900000000-80a2a015caa693fb0bdbSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-000i-0900000000-5d651845e3e03edc63dcSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-000i-0900000000-5ed666462a4d020d9badSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-000i-1900000000-f785c36e33914dd6cfa0Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-052r-3900000000-15fd25c25c09bb878912Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0002-9400000000-42f34c3c13cd670ff16fSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-000i-0900000000-e0e14e382ffa485ebcfcSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-0900000000-80a2a015caa693fb0bdbSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-0900000000-717de91658e43f0217e4Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-0900000000-5ed666462a4d020d9badSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-1900000000-f7a0f4c346c5c2d4669fSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-052r-3900000000-15fd25c25c09bb878912Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-000i-0900000000-e0e14e382ffa485ebcfcSpectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-00kr-0900000000-bd002360ad3147f32bdbSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0002-9400000000-42f34c3c13cd670ff16fSpectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-1b8bb3963db8dbdf68b7Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0900000000-adc00447f61ba09ff2b9Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-c3215810f102f9a6bcd5Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0r7i-7900000000-d9fef758451d2742cf58Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001r-0900000000-6ac7602cc5f3af701662Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0apr-0900000000-b6bce5b5e83f1dd663a7Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-2900000000-dfbd957390c079614963Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
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 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
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference