3,4-Dihydroxyphenylacetic acid

3,4-Dihydroxyphenylacetic acid (DOPAC) is a metabolite of the neurotransmitter dopamine. Dopamine can be metabolized into one of three substances. One such substance is DOPAC. Another is 3-methoxytyramine (3-MT). Both of these substances are degraded to form homovanillic acid (HVA). Both degradations involve the enzymes monoamine oxidase (MAO) and catechol-O-methyl transferase (COMT), albeit in reverse order: MAO catalyzes dopamine to DOPAC, and COMT catalyzes DOPAC to HVA; whereas COMT catalyzes dopamine to 3-MT and MAO catalyzes 3-MT to HVA. The third metabolic end-product of dopamine is norepinephrine (noradrenaline).

Quick facts Names, Identifiers ...

3,4-Dihydroxyphenylacetic acid

Names
Preferred IUPAC name (3,4-Dihydroxyphenyl)acetic acid
Other names 2-(3,4-Dihydroxyphenyl)acetic acid
Identifiers
CAS Number	102-32-9 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:41941 Y
ChEMBL	ChEMBL1284 Y
ChemSpider	532 Y
DrugBank	DB01702 Y
ECHA InfoCard	100.002.750
KEGG	C01161 Y
MeSH	3,4-Dihydroxyphenylacetic+Acid
PubChem CID	547
UNII	KEX5N0R4N5 N
CompTox Dashboard (EPA)	DTXSID9074430
InChI InChI=1S/C8H8O4/c9-6-2-1-5(3-7(6)10)4-8(11)12/h1-3,9-10H,4H2,(H,11,12) Y Key: CFFZDZCDUFSOFZ-UHFFFAOYSA-N Y InChI=1/C8H8O4/c9-6-2-1-5(3-7(6)10)4-8(11)12/h1-3,9-10H,4H2,(H,11,12) Key: CFFZDZCDUFSOFZ-UHFFFAOYAU
SMILES O=C(O)Cc1cc(O)c(O)cc1
Properties
Chemical formula	C8H8O4
Molar mass	168.148 g·mol−1
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

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It can also be found in the bark of Eucalyptus globulus.^[1]

This product has been synthesized (52% yield) from 4-hydroxyphenylacetic acid via aerobic biotransformation using whole cell cultures of Arthrobacter protophormiae.^[2][3]