3,4-Dihydroxyphenylacetaldehyde

3,4-Dihydroxyphenylacetaldehyde
Names

Systematic IUPAC name 2-(3,4-Dihydroxyphenyl)acetaldehyde^[1]
Other names Dopaldehyde
Identifiers
CAS Number	5707-55-1^N
3D model (Jmol)	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	119219
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	152.15 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 ^YN ?)
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

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

Neurotransmitter metabolic intermediates

catecholamines

Anabolism
(tyrosine→epinephrine)

Tyrosine → Levodopa → Dopamine → Norepinephrine → Epinephrine

Catabolism/
metabolites

dopamine:	DOPAL DOPAC MOPET Hydroxytyrosol 3-Methoxytyramine Homovanillic acid

norepinephrine:	3,4-Dihydroxymandelic acid Normetanephrine Vanillylmandelic acid 3-Methoxy-4-hydroxyphenylglycol Dihydroxyphenylethylene glycol

epinephrine:	Metanephrine

tryptophan→serotonin

anabolism:	5-Hydroxytryptophan

catabolism:	5-Hydroxyindoleacetic acid

serotonin→melatonin

Normelatonin

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