U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
This repository is under review for potential modification in compliance with Administration directives.

Details

Stereochemistry ACHIRAL
Molecular Formula C7H6O4
Molecular Weight 154.1201
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 3,4-DIHYDROXYBENZOIC ACID

SMILES

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

InChI

InChIKey=YQUVCSBJEUQKSH-UHFFFAOYSA-N
InChI=1S/C7H6O4/c8-5-2-1-4(7(10)11)3-6(5)9/h1-3,8-9H,(H,10,11)

HIDE SMILES / InChI

Molecular Formula C7H6O4
Molecular Weight 154.1201
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Protocatechuic acid (3,4-dihydroxybenzoic acid, PCA) is a simple phenolic acid. It is found in a large variety of edible plants and possesses various pharmacological activities. This bioactive compound is famous for its biological properties and pharmacological activities such as: antioxidant, antibacterial, anticancer, antiulcer, antidiabetic, antiaging, antifibrotic, antiviral, anti-inflammatory, analgesic, antiatherosclerotic, cardiac, hepatoprotective, neurological and nephroprotective. The neuroprotective effects of PCA, extracted from Alpinia oxyphylla, on H2O2 resulted in apoptosis and oxidative stress in cultured PC12 cells. Apoptotic cell death by H2O2 was dose-dependent. Enhanced effect of PCA on protecting PC12 cells against apoptosis, augmented glutathione (GSH) level and an increase in catalytic activity was investigated by flow cytometric analysis. In cytotoxic assays, PCA causes cell death in HepG2 cancerous cell line of liver showing that PCA stimulates the c-Jun N-terminal kinase (JNK) and p38 subgroups of the mitogen-activated protein kinase (MAPK) family. Treatment with PCA decreased OVA-induced airway hyper-responsiveness to inhaled methacholine. Cell inflammation and mucus hypersecretion was also decreased by PCA. Thus, PCA can be useful for treating asthma. Experimental studies strongly support the role of protocatechuic acid in the prevention of neurodegenerative processes, including Alzheimer's and Parkinson's diseases, due to its favorable influence on processes underlying cognitive and behavioral impairment, namely accumulation of the β-amyloid plaques in brain tissues, hyperphosphorylation of tau protein in neurons, excessive formation of reactive oxygen species and neuroinflammation.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: CHEMBL614731
0.048 mM [IC50]
300.0 µM [IC50]
334.0 µM [IC50]
470.0 nM [Ki]
Conditions

Conditions

PubMed

PubMed

TitleDatePubMed
Medicinal and ethnoveterinary remedies of hunters in Trinidad.
2001
Purification and properties of p-hydroxybenzoate hydroxylases from Rhodococcus strains.
2001 Aug
Specific inhibition of a family 1A dihydroorotate dehydrogenase by benzoate pyrimidine analogues.
2001 Aug 30
Effect of natural phenolic acids on DNA oxidation in vitro.
2001 Dec
Molecular mechanisms controlling the rate and specificity of catechol O-methylation by human soluble catechol O-methyltransferase.
2001 Feb
Inhibition of human plasmin activity using humic acids with arsenic.
2001 Jun 12
Aromatic inhibitors of dehydroquinate synthase: synthesis, evaluation and implications for gallic acid biosynthesis.
2001 Jun 18
Microbial transformations of p-coumaric acid by Bacillus megaterium and Curvularia lunata.
2001 Nov
Toxic dose of a simple phenolic antioxidant, protocatechuic acid, attenuates the glutathione level in ICR mouse liver and kidney.
2001 Nov
Phenolic acids and depsides from some species of the Erodium genera.
2001 Nov-Dec
Kinetic model for phenolic compound oxidation by Fenton's reagent.
2001 Oct
Antimicrobial activity of Argentine plants used in the treatment of infectious diseases. Isolation of active compounds from Sebastiania brasiliensis.
2001 Sep
Genomic analysis of the aromatic catabolic pathways from Pseudomonas putida KT2440.
2002 Dec
New insights into the acid-promoted reaction of caffeic acid and its esters with nitrite: decarboxylation drives chain nitrosation pathways toward novel oxime derivatives and oxidation/fragmentation products thereof.
2002 Feb 8
Spectroscopic and electronic structure studies of protocatechuate 3,4-dioxygenase: nature of tyrosinate-Fe(III) bonds and their contribution to reactivity.
2002 Jan 30
Multiple operons connected with catabolism of aromatic compounds in Acinetobacter sp. strain ADP1 are under carbon catabolite repression.
2002 Jul
Electroorganic synthesis of new benzofuro[2,3-d]pyrimidine derivatives.
2002 Jul 12
Enhanced detection and characterization of protocatechuate 3,4-dioxygenase in Acinetobacter lwoffii K24 by proteomics using a column separation.
2002 Jul 26
Mineralization of aromatic compounds by brown-rot basidiomycetes - mechanisms involved in initial attack on the aromatic ring.
2002 Jun
In vivo protective effect of protocatechuic acid on tert-butyl hydroperoxide-induced rat hepatotoxicity.
2002 May
Antioxidant activity of phenolic compounds isolated from Mesona procumbens Hemsl.
2002 May 8
[The nature of melanin pigments from some micro- and macromycetes].
2002 May-Jun
Inhibition of TNF-alpha induced cell death in human umbilical vein endothelial cells and Jurkat cells by protocatechuic acid.
2002 Nov
Cloning of Acinetobacter calcoaceticus chromosomal region involved in catechin degradation.
2003
Elucidation of the metabolic pathway of fluorene and cometabolic pathways of phenanthrene, fluoranthene, anthracene and dibenzothiophene by Sphingomonas sp. LB126.
2003 Apr
Effect of naturally occurring plant phenolics on the induction of drug metabolizing enzymes by o-toluidine.
2003 Apr 15
Hibiscus protocatechuic acid inhibits lipopolysaccharide-induced rat hepatic damage.
2003 Jan
Effect of 4-coumaric and 3,4-dihydroxybenzoic acid on oxidative DNA damage in rat colonic mucosa.
2003 May
Patents

Sample Use Guides

Rats: Protocatechuic acid (PCA) was administered orally at three different doses (50, 100, 200 mg/kg BW/day) to STZ-diabetic rats for 45 days. PCA at 100 mg possesses a potential antihyperglycemic effect that is comparable with glibenclamide.
Route of Administration: Oral
Protocatechuic acid showed potent inhibition against MAO-B (IC50 300 umol/L) and DBH (334 umol/L), exhibiting weak MAO-A inhibition (2.41 mmol/L).
Substance Class Chemical
Created
by admin
on Wed Apr 02 18:42:22 GMT 2025
Edited
by admin
on Wed Apr 02 18:42:22 GMT 2025
Record UNII
36R5QJ8L4B
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PROTOCATECHUIC ACID
MI   USP-RS  
Preferred Name English
3,4-DIHYDROXYBENZOIC ACID
INCI  
INCI  
Official Name English
DIHYDROXYBENZOIC ACID, 3,4-
Common Name English
PROTOCATECHOIC ACID
Common Name English
PROTOCATECHUIC ACID (PCA)
Common Name English
PROTOCATECHOIC ACID (CONSTITUENT OF MARITIME PINE) [DSC]
Common Name English
FEMA NO. 4430
Code English
PROTOCATECHUIC ACID [MI]
Common Name English
DROXIDOPA METABOLITE (PROTOCATECHOIC ACID)
Common Name English
NSC-16631
Code English
Code System Code Type Description
EVMPD
SUB183866
Created by admin on Wed Apr 02 18:42:22 GMT 2025 , Edited by admin on Wed Apr 02 18:42:22 GMT 2025
PRIMARY
PUBCHEM
72
Created by admin on Wed Apr 02 18:42:22 GMT 2025 , Edited by admin on Wed Apr 02 18:42:22 GMT 2025
PRIMARY
CHEBI
36062
Created by admin on Wed Apr 02 18:42:22 GMT 2025 , Edited by admin on Wed Apr 02 18:42:22 GMT 2025
PRIMARY
MERCK INDEX
m9273
Created by admin on Wed Apr 02 18:42:22 GMT 2025 , Edited by admin on Wed Apr 02 18:42:22 GMT 2025
PRIMARY Merck Index
ECHA (EC/EINECS)
202-760-0
Created by admin on Wed Apr 02 18:42:22 GMT 2025 , Edited by admin on Wed Apr 02 18:42:22 GMT 2025
PRIMARY
FDA UNII
36R5QJ8L4B
Created by admin on Wed Apr 02 18:42:22 GMT 2025 , Edited by admin on Wed Apr 02 18:42:22 GMT 2025
PRIMARY
EPA CompTox
DTXSID4021212
Created by admin on Wed Apr 02 18:42:22 GMT 2025 , Edited by admin on Wed Apr 02 18:42:22 GMT 2025
PRIMARY
SMS_ID
100000170044
Created by admin on Wed Apr 02 18:42:22 GMT 2025 , Edited by admin on Wed Apr 02 18:42:22 GMT 2025
PRIMARY
CAS
99-50-3
Created by admin on Wed Apr 02 18:42:22 GMT 2025 , Edited by admin on Wed Apr 02 18:42:22 GMT 2025
PRIMARY
DRUG BANK
DB03946
Created by admin on Wed Apr 02 18:42:22 GMT 2025 , Edited by admin on Wed Apr 02 18:42:22 GMT 2025
PRIMARY
WIKIPEDIA
Protocatechuic acid
Created by admin on Wed Apr 02 18:42:22 GMT 2025 , Edited by admin on Wed Apr 02 18:42:22 GMT 2025
PRIMARY
NSC
16631
Created by admin on Wed Apr 02 18:42:22 GMT 2025 , Edited by admin on Wed Apr 02 18:42:22 GMT 2025
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT
PARENT -> CONSTITUENT ALWAYS PRESENT
154.5% reaction on PG synthase w/10.0 mM conc. of compound
PARENT -> CONSTITUENT ALWAYS PRESENT
PARENT -> CONSTITUENT ALWAYS PRESENT
PARENT -> CONSTITUENT ALWAYS PRESENT
PARENT -> CONSTITUENT ALWAYS PRESENT
PARENT -> CONSTITUENT ALWAYS PRESENT
Related Record Type Details
PARENT -> METABOLITE
Related Record Type Details
ACTIVE MOIETY
Antiviral