3,4-DIHYDROXYPHENYLACETIC ACID

Details

Stereochemistry	ACHIRAL
Molecular Formula	C8H8O4
Molecular Weight	168.1467
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of 3,4-DIHYDROXYPHENYLACETIC ACID

Structure Search

SMILES

OC(=O)CC1=CC(O)=C(O)C=C1

InChI

InChIKey=CFFZDZCDUFSOFZ-UHFFFAOYSA-N

InChI=1S/C8H8O4/c9-6-2-1-5(3-7(6)10)4-8(11)12/h1-3,9-10H,4H2,(H,11,12)

HIDE SMILES / InChI

Molecular Formula	C8H8O4
Molecular Weight	168.1467
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16365058 | https://www.ncbi.nlm.nih.gov/pubmed/16956664 | https://www.ncbi.nlm.nih.gov/pubmed/28828965

3, 4-dihydroxyphenylacetic acid (DOPAC) is a neuronal metabolite of dopamine (DA). DA undergoes monoamine oxidase-catalyzed oxidative deamination to 3,4-dihydroxyphenylacetaldehyde (DOPAL), which is metabolized primarily to 3,4-dihydroxyphenylacetic acid (DOPAC) via aldehyde dehydrogenase, ALDH2. DOPAC exhibits the antiproliferative effect in colon cancer cells. In addition, DOPAC enhances not only the total ALDH activity but also the gene expression of ALDH1A1, ALDH2, and ALDH3A1 in a concentration-dependent manner. The pretreatment of DOPAC completely protects the cells from the acetaldehyde-induced cytotoxicity, thus DOPAC acts as a potential ALDH inducer to prevent the alcohol-induced abnormal reaction.

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Colon cancer 62 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16365058	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Molecular cloning and characterization of a new multispecific organic anion transporter from rat brain.	1999 May 7	10224140
Patterns of cerebrospinal fluid catechols support increased central noradrenergic responsiveness in aging and Alzheimer's disease.	1999 Sep 15	10494443
Comparison between the role of the neuronal and inducible nitric oxide synthase in methamphetamine-induced neurotoxicity and sensitization.	2000 Sep	11085313
Renal dopaminergic mechanisms in renal parenchymal diseases and hypertension.	2001	11369822
The central catechol-O-methyltransferase inhibitor tolcapone increases striatal hydroxyl radical production in L-DOPA/carbidopa treated rats.	2001	11314772
Effect of GBR 12909 and fluoxetine on the acute and long term changes induced by MDMA ('ecstasy') on the 5-HT and dopamine concentrations in mouse brain.	2001	11077072
Changes in endogenous monoamines in aged rats.	2001 Apr	11251641
Periodic maternal separation of neonatal rats produces region- and gender-specific effects on biogenic amine content in postmortem adult brain.	2001 Apr	11170216
Continuous phencyclidine treatment induces schizophrenia-like hyperreactivity of striatal dopamine release.	2001 Aug	11425499
Molecular mechanisms controlling the rate and specificity of catechol O-methylation by human soluble catechol O-methyltransferase.	2001 Feb	11160877
Changes in striatal electroencephalography and neurochemistry induced by kainic acid seizures are modified by dopamine receptor antagonists.	2001 Feb 16	11226392
Mice with a partial deficiency of manganese superoxide dismutase show increased vulnerability to the mitochondrial toxins malonate, 3-nitropropionic acid, and MPTP.	2001 Jan	11161607
The central aromatic amino acid DOPA decarboxylase inhibitor, NSD-1015, does not inhibit L-DOPA-induced circling in unilateral 6-OHDA-lesioned-rats.	2001 Jan	11135014
Protective effect of quinacrine on striatal dopamine levels in 6-OHDA and MPTP models of Parkinsonism in rodents.	2001 Jan 1	11226716
Nicotine prevents striatal dopamine loss produced by 6-hydroxydopamine lesion in the substantia nigra.	2001 Jan 12	11150495
Significance of glutamate and dopamine neurons in the ventral pallidum in the expression of behavioral sensitization to amphetamine.	2001 Jan 19	11212872
Biogenic aldehyde(s) derived from the action of monoamine oxidase may mediate the antidipsotropic effect of daidzin.	2001 Jan 30	11306106
Cloning of the genes for a 4-sulphocatechol-oxidizing protocatechuate 3,4-dioxygenase from Hydrogenophaga intermedia S1 and identification of the amino acid residues responsible for the ability to convert 4-sulphocatechol.	2001 Jul	11454212
Dissociation of prolactin secretion from tuberoinfundibular dopamine activity in late pregnant rats.	2001 Jun	11356724
Inhibition of cytochrome P450 2E1 induces an increase in extracellular dopamine in rat substantia nigra: a new metabolic pathway?	2001 Jun 15	11309845
Oxygen inhalation enhances striatal dopamine metabolism and monoamineoxidase enzyme inhibition prevents it: a microdialysis study.	2001 Jun 22	11430914
3,4-Methylenedioxymethamphetamine induces monoamine release, but not toxicity, when administered centrally at a concentration occurring following a peripherally injected neurotoxic dose.	2001 Mar	11351932
Effects of orphanin FQ on central dopaminergic neuronal activities and prolactin secretion.	2001 Mar	11171648
Evidence for a dissociation between MPTP toxicity and tyrosinase activity based on congenic mouse strain susceptibility.	2001 Mar	11170726
Ovulation delay induced by blockade of the cholinergic system on dioestrus-1, is related to changes in dopaminergic activity of the preoptic anterior-hypothalamic area of the rat.	2001 Mar 1	11306184
Day/night variations of dopamine ocular content during Xenopus laevis ontogeny.	2001 Mar 16	11226628
Neuroprotective effects of GDNF against 6-OHDA in young and aged rats.	2001 Mar 30	11277973
Rapid changes in monoamine levels following administration of corticotropin-releasing factor or corticosterone are localized in the dorsomedial hypothalamus.	2001 May	11300710
Prostaglandins play an important role in diurnal changes of tuberoinfundibular dopaminergic neuronal activity and prolactin secretion in ovariectomized, estrogen-treated rats.	2001 May 1	11427342
Chronic estrogen treatment replaces striatal dopaminergic function in ovariectomized rats.	2001 May 11	11334794

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:22:20 GMT 2023` Edited by `admin` on `Fri Dec 15 15:22:20 GMT 2023`
Record UNII	KEX5N0R4N5
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

3,4-DIHYDROXYPHENYLACETIC ACID

Systematic Name

English

2-(3,4-DIHYDROXYPHENYL)ACETIC ACID

Systematic Name

English

BENZENEACETIC ACID, 3,4-DIHYDROXY-

Systematic Name

English

3,4-DIHYDROXYBENZENEACETIC ACID

Systematic Name

English

(3,4-DIHYDROXYPHENYL)ACETIC ACID

Systematic Name

English

HOMOPROTOCATECHUIC ACID

Common Name

English

HMDB01336

Code

English

DOPACETIC ACID

Common Name

English

NSC-73191

Code

English

DIHYDROXYPHENYLACETIC ACID

Systematic Name

English

DOPAC

Common Name

English

ACETIC ACID, (3,4-DIHYDROXYPHENYL)-

Systematic Name

English

Code System Code Type Description

CAS

102-32-9