13023-73-9

Basic information

• Product Name: 2-(3,4-dihydroxyphenyl)-2-hydroxy-acetaldehyde
• Synonyms: 2-(3,4-dihydroxyphenyl)-2-hydroxy-acetaldehyde;3,4-Dihydroxymandelaldehyde;3,4-dihydroxyphenylglycolaldehyde
• CAS NO: 13023-73-9
• Molecular Formula: C₈H₈O₄
• Molecular Weight: 168.15
• Mol File: 13023-73-9.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 391.9°Cat760mmHg
• Flash Point: 205°C
• Appearance: /
• Density: 1.466g/cm³
• Vapor Pressure: 7.64E-07mmHg at 25°C
• Refractive Index: 1.639
• PKA: 9.43±0.10(Predicted)
• CAS DataBase Reference: 2-(3,4-dihydroxyphenyl)-2-hydroxy-acetaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(3,4-dihydroxyphenyl)-2-hydroxy-acetaldehyde(13023-73-9)
• EPA Substance Registry System: 2-(3,4-dihydroxyphenyl)-2-hydroxy-acetaldehyde(13023-73-9)

Safety Data

• Hazardous Substances Data: 13023-73-9(Hazardous Substances Data)

Usage

Uses

3,4-Dihydroxyphenylglycolaldehyde (Dopegal) is the monoamine oxidase metabolite of dopamine which is toxic of in a concentrated amount and may be a target for Alzheimer or Parkinson’s therapy.

Definition

ChEBI: An aldehyde consisting of phenylacetaldehyde having three hydroxy substituents located at the alpha-, 3- and 4-positions

InChI:InChI=1/C8H8O4/c9-4-8(12)5-1-2-6(10)7(11)3-5/h1-4,8,10-12H

Upstream product

• 120-80-9 benzene-1,2-diol 
• 582289-87-0 2-(3,4-bis(tetrahydropyran-2-yloxy)phenyl)-2-(tetrahydropyran-2-yloxy)acetic acid methyl ester 
• 582289-88-1 2-(3,4-bis(tetrahydropyran-2-yloxy)phenyl)-2-(tetrahydropyran-2-yloxy)acetaldehyde 
• 582289-86-9 2-(3,4-bis(tetrahydropyran-2-yloxy)phenyl)-2-hydroxyacetic acid methyl ester 
• 582289-84-7 3,4-bis(tetrahydropyran-2-yloxy)phenylacetic acid methyl ester 
• 25379-88-8 2-(3,4-dihydroxyphenyl)acetic acid methyl ester 
• 102-32-9 3,4-dihydroxyphenylacetate 

Relevant articles and documents

Synthetic Evidence of the Amadori-Type Alkylation of Biogenic Amines by the Neurotoxic Metabolite Dopegal

The neurotransmitter metabolite 3,4-dihydroxy-phenylglycolaldehyde (dopegal) damages neurons and the myocardium by protein cross-linking, resulting in conglomerations and cell death. We investigated this process on a synthetic scale, leading to the discovery of an Amadori-type rearrangement of dopegal in the reaction with several amino acids and neuropeptides. This alkylation also occurs with neurotransmitters, suggesting an influence of dopegal on neurochemical processes. The rearrangement occurs readily under physiological conditions.

Synthesis of a Biochemically Important Aldehyde, 3,4-Dihydroxyphenylglycolaldehyde

3,4-Dihydroxyphenylglycolaldehyde (DOPEGAL) is an important precursor of the major brain metabolites of noradrenaline, 3,4-dihydroxyphenylglycol, and 3-methoxy-4-hydroxyphenylglycol.Methods for the synthesis of DOPEGAL have been developed.The α-hydroxy an