3,4-Dihydroxyphenylacetaldehyde

From Wikipedia, the free encyclopedia
Jump to navigation Jump to search
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 B00668
Abbreviations DOPAL
ChEBI
ChemSpider
ECHA InfoCard 100.237.172
KEGG
MeSH 3,4-dihydroxyphenylacetaldehyde
Properties
C8H8O3
Molar mass 152.15 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).
☒N verify (what is ☑Y☒N ?)
Infobox references

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.

References[edit]

  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 biochemicallly important aldehyde - 3,4-dihydroxyphenylacetaldehyde", Bio-Organic Chemistry, 26, 45-50, 1998.