3,4-Dihydroxyphenylacetic acid

Synonym(s):DOPAC;Homoprotocatechuic acid

CAS NO.：102-32-9
Empirical Formula: C8H8O4
Molecular Weight: 168.15
MDL number: MFCD00004338
EINECS: 203-024-1
SAFETY DATA SHEET (SDS)
Update Date: 2024-08-19 17:35:41

3,4-Dihydroxyphenylacetic acid Structural

What is 3,4-Dihydroxyphenylacetic acid?

Description

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.
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Chemical properties

beige to light brown crystalline powder

The Uses of 3,4-Dihydroxyphenylacetic acid

3,4-Dihydroxyphenylacetic Acid is a metabolite of Dopamine (D533782).

The Uses of 3,4-Dihydroxyphenylacetic acid

3,4-Dihydroxyphenylacetic acid is an important metabolite when studying the behavior of the dopaminergic system.

Definition

ChEBI: (3,4-dihydroxyphenyl)acetic acid is a dihydroxyphenylacetic acid having the two hydroxy substituents located at the 3- and 4-positions. It is a metabolite of dopamine. It has a role as a human metabolite. It is a dihydroxyphenylacetic acid and a member of catechols. It is functionally related to a phenylacetic acid. It is a conjugate acid of a (3,4-dihydroxyphenyl)acetate.

General Description

3,4-dihydroxyphenylacetic acid (DOPAC) is a normal constituent of rat brain tissue. A mass fragmentographic method for determination of DOPAC in rat brain tissue has been described. It is major metabolite of dopamine (DA). The voltammetric reduction of DOPAC has been studied at a glassy carbon electrode modified with single-wall carbon nanotubes (SWNTs). Semi-automatic fluorometric assay technique for DOPAC has been reported.

Properties of 3,4-Dihydroxyphenylacetic acid

Melting point:	127-130 °C (lit.)
Boiling point:	257.07°C (rough estimate)
Density	1.3037 (rough estimate)
refractive index	1.5090 (estimate)
storage temp.	Inert atmosphere,Room Temperature
solubility	water: soluble50mg/mL, clear, almost colorless
form	Powder, Crystals or Lumps
pka	4.42±0.10(Predicted)
color	White to off-white
Water Solubility	Soluble in water and methanol.
BRN	2211017
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)
CAS DataBase Reference	102-32-9(CAS DataBase Reference)
NIST Chemistry Reference	Acetic acid, (3,4-dihydroxyphenyl)-,(102-32-9)
EPA Substance Registry System	3,4-Dihydroxyphenylacetic acid (102-32-9)

Safety information for 3,4-Dihydroxyphenylacetic acid

Signal word	Warning
Pictogram(s)	Exclamation Mark Irritant GHS07
GHS Hazard Statements	H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes	P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P271:Use only outdoors or in a well-ventilated area. P280:Wear protective gloves/protective clothing/eye protection/face protection. P302+P352:IF ON SKIN: wash with plenty of soap and water. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.