3,4-Dihydroxyphenylacetaldehyde

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 ;
3D model (JSmol)	Interactive image; Interactive image;
3DMet	B00668;
Abbreviations	DOPAL
ChEBI	CHEBI:27978 ;
ChemSpider	106504 ;
ECHA InfoCard	100.237.172
IUPHAR/BPS	6632;
KEGG	C04043 ;
MeSH	3,4-dihydroxyphenylacetaldehyde
PubChem CID	119219;
UNII	F2E9Q24TSL ;
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 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	152.149 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). verify (what is ?) 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. 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

"3,4-dihydroxyphenylacetaldehyde - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 24 June 2005. Identification and Related Records. Retrieved 13 October 2011.
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.
Li, W., Spaziano, V.T., Burke, WJ., "Synthesis of a biochemically important aldehyde - 3,4-dihydroxyphenylacetaldehyde", Bio-Organic Chemistry, 26, 45-50, 1998.
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.

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[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.

[:0-4] 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.