3,4-Dihydroxyphenylacetaldehyde

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.

3,4-Dihydroxyphenylacetaldehyde

Names
Preferred IUPAC name (3,4-Dihydroxyphenyl)acetaldehyde
Other names 2-(3,4-Dihydroxyphenyl)acetaldehyde[1] Dopaldehyde
Identifiers
CAS Number	5707-55-1^N
3D model (JSmol)	Interactive image Interactive image
3DMet	B00668
Abbreviations	DOPAL
ChEBI	CHEBI:27978^Y
ChemSpider	106504^Y
ECHA InfoCard	100.237.172
IUPHAR/BPS	6632
KEGG	C04043^Y
MeSH	3,4-dihydroxyphenylacetaldehyde
PubChem CID	119219
CompTox Dashboard (EPA)	DTXSID10205680
InChI InChI=1S/C8H8O3/c9-4-3-6-1-2-7(10)8(11)5-6/h1-2,4-5,10-11H,3H2^Y Key: IADQVXRMSNIUEL-UHFFFAOYSA-N^Y 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
SMILES Oc1ccc(CC=O)cc1O OC1=CC=C(CC=O)C=C1O
Properties
Chemical formula	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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Infobox references

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.