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Details

Stereochemistry ACHIRAL
Molecular Formula C7H6O4
Molecular Weight 154.1204
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

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

SMILES

c1cc(c(cc1C(=O)O)O)O

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 154.1204
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
A transcriptional luxAB reporter fusion responding to fluorene in Sphingomonas sp. LB126 and its initial characterisation for whole-cell bioreporter purposes.
2001 Dec
Molecular mechanisms controlling the rate and specificity of catechol O-methylation by human soluble catechol O-methyltransferase.
2001 Feb
Regulation of the p-hydroxybenzoic acid hydroxylase gene (pobA) in plant-growth-promoting Pseudomonas putida WCS358.
2001 Jun
A catechol antioxidant protocatechuic acid potentiates inflammatory leukocyte-derived oxidative stress in mouse skin via a tyrosinase bioactivation pathway.
2001 May 1
Microbial transformations of p-coumaric acid by Bacillus megaterium and Curvularia lunata.
2001 Nov
Effects of the nitrone radical scavengers PBN and S-PBN on in vivo trapping of reactive oxygen species after traumatic brain injury in rats.
2001 Nov
Biodegradation of p-toluenesulphonamide by a Pseudomonas sp.
2001 Nov 13
Biodegradation of dimethylphenols by bacteria with different ring-cleavage pathways of phenolic compounds.
2002
In vitro anti-influenza virus activity of synthetic humate analogues derived from protocatechuic acid.
2002
Genomic analysis of the aromatic catabolic pathways from Pseudomonas putida KT2440.
2002 Dec
Isolation and quantitative analysis of phenolic antioxidants, free sugars, and polyols from mango (Mangifera indica L.) stem bark aqueous decoction used in Cuba as a nutritional supplement.
2002 Feb 13
Determination of active ingredients of Rhododendron dauricum L. by capillary electrophoresis with electrochemical detection.
2002 Jan 11
Multiple operons connected with catabolism of aromatic compounds in Acinetobacter sp. strain ADP1 are under carbon catabolite repression.
2002 Jul
Peroxynitrite scavenging activities of aromatic compounds isolated from Konnyaku, Amorphophallus konjac K.Koch.
2002 Jun
Oxidation of 3,4-dihydroxybenzoic acid by means of hydrogen peroxide in aqueous goethite slurry.
2002 Jun
Hibiscus protocatechuic acid or esculetin can inhibit oxidative LDL induced by either copper ion or nitric oxide donor.
2002 Mar 27
Inhibition of TNF-alpha induced cell death in human umbilical vein endothelial cells and Jurkat cells by protocatechuic acid.
2002 Nov
A trigonal-bipyramidal ferric aqua complex with a sterically hindered salen ligand as a model for the active site of protocatechuate 3,4-dioxygenase.
2002 Oct 4
Characterization of four olive-mill-wastewater indigenous bacterial strains capable of aerobically degrading hydroxylated and methoxylated monocyclic aromatic compounds.
2002 Sep
Oxidative dimers produced from protocatechuic and gallic esters in the DPPH radical scavenging reaction.
2002 Sep 11
Elucidation of the metabolic pathway of fluorene and cometabolic pathways of phenanthrene, fluoranthene, anthracene and dibenzothiophene by Sphingomonas sp. LB126.
2003 Apr
Antioxidant activity of 3-dehydroshikimic acid in liposomes, emulsions, and bulk oil.
2003 Apr 23
Degradation of phenanthrene and naphthalene by a Burkholderia species strain.
2003 Feb
Photo-Fenton treatment of water containing natural phenolic pollutants.
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 Fri Jun 25 23:17:30 UTC 2021
Edited
by admin
on Fri Jun 25 23:17:30 UTC 2021
Record UNII
36R5QJ8L4B
Record Status Validated (UNII)
Record Version
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Name Type Language
3,4-DIHYDROXYBENZOIC ACID
INCI  
INCI  
Official Name English
PROTOCATECHUIC ACID
MI   USP-RS  
Systematic Name English
DIHYDROXYBENZOIC ACID, 3,4-
Common Name English
3,4-DIHYDROXYBENZOIC ACID [INCI]
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 Fri Jun 25 23:17:30 UTC 2021 , Edited by admin on Fri Jun 25 23:17:30 UTC 2021
PRIMARY
PUBCHEM
72
Created by admin on Fri Jun 25 23:17:30 UTC 2021 , Edited by admin on Fri Jun 25 23:17:30 UTC 2021
PRIMARY
MERCK INDEX
M9273
Created by admin on Fri Jun 25 23:17:30 UTC 2021 , Edited by admin on Fri Jun 25 23:17:30 UTC 2021
PRIMARY Merck Index
ECHA (EC/EINECS)
202-760-0
Created by admin on Fri Jun 25 23:17:30 UTC 2021 , Edited by admin on Fri Jun 25 23:17:30 UTC 2021
PRIMARY
FDA UNII
36R5QJ8L4B
Created by admin on Fri Jun 25 23:17:30 UTC 2021 , Edited by admin on Fri Jun 25 23:17:30 UTC 2021
PRIMARY
EPA CompTox
99-50-3
Created by admin on Fri Jun 25 23:17:30 UTC 2021 , Edited by admin on Fri Jun 25 23:17:30 UTC 2021
PRIMARY
CAS
99-50-3
Created by admin on Fri Jun 25 23:17:30 UTC 2021 , Edited by admin on Fri Jun 25 23:17:30 UTC 2021
PRIMARY
DRUG BANK
DB03946
Created by admin on Fri Jun 25 23:17:30 UTC 2021 , Edited by admin on Fri Jun 25 23:17:30 UTC 2021
PRIMARY
WIKIPEDIA
Protocatechuic acid
Created by admin on Fri Jun 25 23:17:30 UTC 2021 , Edited by admin on Fri Jun 25 23:17:30 UTC 2021
PRIMARY
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