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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
Medicinal and ethnoveterinary remedies of hunters in Trinidad.
2001
Fluorene degradation by Sphingomonas sp. LB126 proceeds through protocatechuic acid: a genetic analysis.
2001 Dec
A transcriptional luxAB reporter fusion responding to fluorene in Sphingomonas sp. LB126 and its initial characterisation for whole-cell bioreporter purposes.
2001 Dec
Catecholamine metabolism in the brain by membrane-bound and soluble catechol-o-methyltransferase (COMT) estimated by enzyme kinetic values.
2001 Nov
Microbial transformations of p-coumaric acid by Bacillus megaterium and Curvularia lunata.
2001 Nov
Biodegradation of p-toluenesulphonamide by a Pseudomonas sp.
2001 Nov 13
Phenolic acids and depsides from some species of the Erodium genera.
2001 Nov-Dec
Molecularly imprinted polymer using-p-hydroxybenzoic acid, p-hydroxyphenylacetic acid and p-hydroxyphenylpropionic acid as templates.
2001 Nov-Dec
Biodegradation of dimethylphenols by bacteria with different ring-cleavage pathways of phenolic compounds.
2002
Effect of natural phenols on the catalytic activity of cytochrome P450 2E1.
2002
In vitro anti-influenza virus activity of synthetic humate analogues derived from protocatechuic acid.
2002
The trans-anethole degradation pathway in an Arthrobacter sp.
2002 Apr 5
[Study on the constituents from Neonauclea sessilifolia].
2002 Dec
Genomic analysis of the aromatic catabolic pathways from Pseudomonas putida KT2440.
2002 Dec
Evaluation of the antioxidant properties of free and bound phenolic acids from native and malted finger millet (ragi, Eleusine coracana Indaf-15).
2002 Feb 13
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
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
Phenolic compounds from Hypericum perforatum.
2002 Jan
Natural products inhibiting Candida albicans secreted aspartic proteases from Tovomita krukovii.
2002 Jan
4-Hydroxybenzoate uptake in Klebsiella planticola strain DSZ1 is driven by DeltapH.
2002 Jan
New prenylated benzoic acid and other constituents from almond hulls (Prunus amygdalus Batsch).
2002 Jan 30
Spectroscopic and electronic structure studies of protocatechuate 3,4-dioxygenase: nature of tyrosinate-Fe(III) bonds and their contribution to reactivity.
2002 Jan 30
The activity of Arabidopsis glycosyltransferases toward salicylic acid, 4-hydroxybenzoic acid, and other benzoates.
2002 Jan 4
Multiple operons connected with catabolism of aromatic compounds in Acinetobacter sp. strain ADP1 are under carbon catabolite repression.
2002 Jul
An in vitro hydroxyl radical generation assay for microdialysis sampling calibration.
2002 Jul 1
Protective effect of colored rice over white rice on Fenton reaction-based renal lipid peroxidation in rats.
2002 May
Identification of phenyldecanoic acid as a constituent of triacylglycerols and wax ester produced by Rhodococcus opacus PD630.
2002 May
Copper-induced vascular endothelial growth factor expression and wound healing.
2002 May
In vitro cytotoxicity of protocatechuic acid to cultured human cells from oral tissue: involvement in oxidative stress.
2002 Nov
Characterization of five phyllosphere bacteria isolated from Rosa rugosa leaves, and their phenotypic and metabolic properties.
2002 Nov
Efficient synthesis and cell-transfection properties of a new multivalent cationic lipid for nonviral gene delivery.
2002 Nov 7
Effects of L-ascorbic acid on lysyl oxidase in the formation of collagen cross-links.
2002 Oct
Sessiline, a new nitrogenous compound from the fruits of Acanthopanax sessiliflorus.
2002 Oct
Further investigation of the modifying effect of various chemopreventive agents on apoptosis and cell proliferation in human colon cancer cells.
2002 Oct
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
Oxidative dimers produced from protocatechuic and gallic esters in the DPPH radical scavenging reaction.
2002 Sep 11
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
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
Redox reactions obtained by gamma irradiation of quercetin methanol solution are similar to in vivo metabolism.
2003 Feb
Effects of phenolic acids on human phenolsulfotransferases in relation to their antioxidant activity.
2003 Feb 26
Photo-Fenton treatment of water containing natural phenolic pollutants.
2003 Jan
Hibiscus protocatechuic acid inhibits lipopolysaccharide-induced rat hepatic damage.
2003 Jan
Identification of the hydroxyl radical and other reactive oxygen species in human neutrophil granulocytes exposed to a fragment of the amyloid beta peptide.
2003 Mar
Phthalate catabolic gene cluster is linked to the angular dioxygenase gene in Terrabacter sp. strain DBF63.
2003 Mar
High-performance liquid chromatography determination of phenolic constituents in 17 varieties of cowpeas.
2003 Mar 12
Hydroxyl radical formation is greater in striatal core than in penumbra in a rat model of ischemic stroke.
2003 Mar 15
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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