3,4-Dihydroxyphenylacetaldehyde

3,4-Dihydroxyphenylacetaldehyde

Names
Systematic IUPAC name 2-(3,4-Dihydroxyphenyl)acetaldehyde[1]
Identifiers
CAS Number	5707-55-1
3DMet	B00668
Abbreviations	DOPAL
ChEBI	CHEBI:27978
ChemSpider	106504
IUPHAR/BPS	6632
Jmol interactive 3D	Image Image
KEGG	C04043
MeSH	3,4-dihydroxyphenylacetaldehyde
PubChem	119219
InChI InChI=1S/C8H8O3/c9-4-3-6-1-2-7(10)8(11)5-6/h1-2,4-5,10-11H,3H2 Key: IADQVXRMSNIUEL-UHFFFAOYSA-N 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	152.15 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).
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Infobox references

3,4-Dihydroxyphenylacetaldehyde (DOPAL) is a metabolite of the neurotransmitter dopamine. DOPAL is an important precursor of the major brain metabolites of dopamine, 3,4-dihydroxyphenylacetic acid and 4-hydroxy-3-methoxy-phenylacetic acid. DOPAL plays a role in Parkinson's disease.^[2] DOPAL has been chemically synthesized.^[3]

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