3,4-Dihydroxymandelaldehyde (CHEM036048)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 07:10:44 UTC
Update Date2016-11-09 01:21:25 UTC
Accession NumberCHEM036048
Identification
Common Name3,4-Dihydroxymandelaldehyde
ClassSmall Molecule
Description3,4-Dihydroxymandelaldehyde, also known as 3,4-dihydroxymandelaldehyde or 3,4-dihydroxymandelaldehyde, belongs to the class of organic compounds known as phenylacetaldehydes. Phenylacetaldehydes are compounds containing a phenylacetaldehyde moiety, which consists of a phenyl group substituted at the second position by an acetalydehyde. 3,4-Dihydroxymandelaldehyde is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 3,4-Dihydroxymandelaldehyde exists in all living organisms, ranging from bacteria to humans. 3,4-Dihydroxymandelaldehyde participates in a number of enzymatic reactions, within cattle. In particular, 3,4-Dihydroxymandelaldehyde can be biosynthesized from norepinephrine through the action of the enzyme amine oxidase [flavin-containing] a. In addition, 3,4-Dihydroxymandelaldehyde and methylamine can be biosynthesized from epinephrine; which is mediated by the enzyme amine oxidase [flavin-containing] a. In cattle, 3,4-dihydroxymandelaldehyde is involved in the metabolic pathway called the tyrosine metabolism pathway.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3,4-Dihydroxymandelic aldehydeChEBI
3,4-DihydroxyphenylglycolaldehydeChEBI
3,4-Dihydroxyphenylglycolic aldehydeChEBI
alpha,3,4-TrihydroxybenzeneacetaldehydeChEBI
alpha,3,4-TrihydroxyphenylacetaldehydeChEBI
DHMALChEBI
DHPGALDChEBI
DOPEGALChEBI
a,3,4-TrihydroxybenzeneacetaldehydeGenerator
Α,3,4-trihydroxybenzeneacetaldehydeGenerator
a,3,4-TrihydroxyphenylacetaldehydeGenerator
Α,3,4-trihydroxyphenylacetaldehydeGenerator
a,3,4-Trihydroxy-benzeneacetaldehydeHMDB
alpha,3,4-Trihydroxy-benzeneacetaldehydeHMDB
Chemical FormulaC8H8O4
Average Molecular Mass168.147 g/mol
Monoisotopic Mass168.042 g/mol
CAS Registry Number13023-73-9
IUPAC Name2-(3,4-dihydroxyphenyl)-2-hydroxyacetaldehyde
Traditional Namedhmal
SMILESOC(C=O)C1=CC(O)=C(O)C=C1
InChI IdentifierInChI=1S/C8H8O4/c9-4-8(12)5-1-2-6(10)7(11)3-5/h1-4,8,10-12H
InChI KeyYUGMCLJIWGEKCK-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenylacetaldehydes. Phenylacetaldehydes are compounds containing a phenylacetaldehyde moiety, which consists of a phenyl group substituted at the second position by an acetalydehyde.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylacetaldehydes
Direct ParentPhenylacetaldehydes
Alternative Parents
Substituents
  • Phenylacetaldehyde
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Alpha-hydroxyaldehyde
  • Secondary alcohol
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organic oxygen compound
  • Carbonyl group
  • Aldehyde
  • Aromatic alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility11 g/LALOGPS
logP0.2ALOGPS
logP0.13ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)9.2ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity41.74 m³·mol⁻¹ChemAxon
Polarizability15.68 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-06ri-1900000000-d14339278a251a7d9df1Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-01b9-7079000000-441c5f66bee2b8f14be7Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-01c8f9ca75c86beb7118Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gb9-0900000000-30165da526b8042721a9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kn9-9800000000-24ef8505a6b8f892128dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-2ce2cd9a3f1a5d4737b3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0aor-0900000000-a9b6cf257bb2c852ffd9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-6900000000-1f2d65b1c1a32c4ea1fdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014j-0900000000-876434025a3e5951556fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0900000000-667ec91845715350734fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9200000000-1663e47bc16a5fa465e4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fki-0900000000-d67f635e503103dc887eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0r7i-4900000000-0f535b7035498a1a6303Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ue9-9200000000-344fc9120de4f34191d3Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0006242
FooDB IDFDB030386
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID46056
BioCyc IDDIHYDROXYPHENYLGLYCOLALDEHYDE
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID133725
ChEBI ID27852
PubChem Compound ID151725
Kegg Compound IDC05577
YMDB IDNot Available
ECMDB IDECMDB06242
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Marchitti SA, Deitrich RA, Vasiliou V: Neurotoxicity and metabolism of the catecholamine-derived 3,4-dihydroxyphenylacetaldehyde and 3,4-dihydroxyphenylglycolaldehyde: the role of aldehyde dehydrogenase. Pharmacol Rev. 2007 Jun;59(2):125-50. Epub 2007 Mar 22.
2. Burke WJ, Li SW, Chung HD, Ruggiero DA, Kristal BS, Johnson EM, Lampe P, Kumar VB, Franko M, Williams EA, Zahm DS: Neurotoxicity of MAO metabolites of catecholamine neurotransmitters: role in neurodegenerative diseases. Neurotoxicology. 2004 Jan;25(1-2):101-15.
3. Burke WJ, Li SW, Zahm DS, Macarthur H, Kolo LL, Westfall TC, Anwar M, Glickstein SB, Ruggiero DA: Catecholamine monoamine oxidase a metabolite in adrenergic neurons is cytotoxic in vivo. Brain Res. 2001 Feb 9;891(1-2):218-27.
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=10424772
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=11532332
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=12729575
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=14697885
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=18783367
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=8813375
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=9237550
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=9518674
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=9878889