3,4-Dihydroxyphenylacetaldehyde

3,4-Dihydroxyphenylacetaldehyde
Kekulé, skeletal formula of 3,4-dihydroxyphenylacetaldehyde
Names
Preferred IUPAC name
(3,4-Dihydroxyphenyl)acetaldehyde
Other names
DOPAL; 2-(3,4-Dihydroxyphenyl)acetaldehyde;[1] Dopaldehyde; Dopamine aldehyde
Identifiers
3D model (JSmol)
3DMet
Abbreviations DOPAL
ChEBI
ChemSpider
ECHA InfoCard 100.237.172 Edit this at Wikidata
KEGG
MeSH 3,4-dihydroxyphenylacetaldehyde
UNII
  • InChI=1S/C8H8O3/c9-4-3-6-1-2-7(10)8(11)5-6/h1-2,4-5,10-11H,3H2 checkY
    Key: IADQVXRMSNIUEL-UHFFFAOYSA-N checkY
  • InChI=1/C8H8O3/c9-4-3-6-1-2-7(10)8(11)5-6/h1-2,4-5,10-11H,3H2
    Key: IADQVXRMSNIUEL-UHFFFAOYAV
  • Oc1ccc(CC=O)cc1O
  • OC1=CC=C(CC=O)C=C1O
Properties
C8H8O3
Molar mass 152.149 g·mol−1
Density 1.306 g/mL
Boiling point 351 °C (664 °F; 624 K)
Related compounds
Related 2-phenyl aldehydes
 Phenylacetaldehyde

Phenylglyoxal

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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3,4-Dihydroxyphenylacetaldehyde (DOPAL), also known as dopamine aldehyde, is a metabolite of the monoamine neurotransmitter dopamine formed by monoamine oxidase (MAO).[2][3]

Other metabolic pathways of dopamine metabolism include methylation by catechol O-methyltransferase (COMT) into 3-methoxytyramine and β-hydroxylation by dopamine β-hydroxylase (DBH) into norepinephrine. There is also spontaneous oxidation of dopamine into dopamine quinones and reactive oxygen species.[3]

  1. ^ "3,4-dihydroxyphenylacetaldehyde - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 24 June 2005. Identification and Related Records. Retrieved 13 October 2011.
  2. ^ Cite error: The named reference Goldstein2020a was invoked but never defined (see the help page).
  3. ^ a b Cite error: The named reference Goldstein2021 was invoked but never defined (see the help page).