3,4-Dihydroxyphenylacetic acid

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

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).

DOPAC can be oxidized by hydrogen peroxide, leading to the formation of toxic metabolites which destroy dopamine storage vesicles in the substantia nigra. This may contribute to the failure of levodopa treatment of Parkinson's disease. A MAO-B inhibitor such as selegiline or rasagiline can prevent this from happening.^{[citation needed]}

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]

References

This page was last edited on 24 January 2024, at 09:51