3,4-Dihydroxyphenylacetaldehyde
Kekulé, skeletal formula of 3,4-dihydroxyphenylacetaldehyde
Names
Preferred IUPAC name
(3,4-Dihydroxyphenyl)acetaldehyde
Other names
2-(3,4-Dihydroxyphenyl)acetaldehyde[1]
Dopaldehyde
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) is an important metabolite of the major brain neurotransmitter dopamine. All of the enzymatic metabolism of dopamine in neurons passes through DOPAL. According to the "catecholaldehyde hypothesis," DOPAL plays a role in the pathogenesis of Parkinson's disease.[2] DOPAL has been chemically synthesized.[3] DOPAL is detoxified mainly by aldehyde dehydrogenase. DOPAL is a metabolite of dopamine by monoamine oxidase activity, or MAO, in differentiated neuronal cells of the PC12 line. [4]Physiological concentrations of DOPAL in isolated mitochondria were highly potent in inducing a pathway associated with programmed cell death (or apoptosis), permeability transition. This suggests the cytotoxity of DOPAL and its role in the progression of Parkinson's disease, which has long been associated with mitochondrial abnormalities and neurotoxicity by way of dopaminergic compounds, while reducing the emphasis on other dopamine derivatives and metabolites.[4]

References

  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. ^ Goldstein DS, Sullivan P, Holmes C, Miller GW, Alter S, Strong R, Mash DC, Kopin IJ, Sharabi Y., "Determinants of buildup of the toxic dopamine metabolite DOPAL in Parkinson's disease," J. Neurochem. 2013 Sep;126(5):591-603.
  3. ^ Li, W., Spaziano, V.T., Burke, WJ., "Synthesis of a biochemically important aldehyde - 3,4-dihydroxyphenylacetaldehyde", Bio-Organic Chemistry, 26, 45-50, 1998.
  4. ^ a b Kristal, B. S., Conway, A. D., Brown, A. M., Jain, J. C., Ulluci, P. A., Li, S. W., & Burke, W. J. (2001). Selective dopaminergic vulnerability: 3, 4-dihydroxyphenylacetaldehyde targets mitochondria. Free Radical Biology and Medicine, 30(8), 924-931.