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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
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
Bacterial aerobic degradation of benzene, toluene, ethylbenzene and xylene.
2002
In vitro anti-influenza virus activity of synthetic humate analogues derived from protocatechuic acid.
2002
Antioxidative phenolic compounds isolated from almond skins (Prunus amygdalus Batsch).
2002 Apr 10
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
Structural characterisation of humic acid-bound PAH residues in soil by 13C-CPMAS-NMR-spectroscopy: evidence of covalent bonds.
2002 Jul
[Identification of chemical structure of antibacterial components against Legionella pneumophila in a coffee beverage].
2002 Jul
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
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
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
Phytochemical constituents from the fruits of Acanthopanax sessiliflorus.
2002 Jun
Mineralization of aromatic compounds by brown-rot basidiomycetes - mechanisms involved in initial attack on the aromatic ring.
2002 Jun
Anaerobic degradation of protocatechuate (3,4-dihydroxybenzoate) by Thauera aromatica strain AR-1.
2002 Jun 18
Antioxidant activity of prune (Prunus domestica L.) constituents and a new synergist.
2002 Jun 19
Determination of free and total phenolic acids in plant-derived foods by HPLC with diode-array detection.
2002 Jun 19
Hibiscus protocatechuic acid or esculetin can inhibit oxidative LDL induced by either copper ion or nitric oxide donor.
2002 Mar 27
Oxygenative cleavage of catechols including protocatechuic acid with molecular oxygen in water catalysed by water-soluble non-heme iron(III) complexes in relevance to catechol dioxygenases.
2002 Mar 7
Protective effect of colored rice over white rice on Fenton reaction-based renal lipid peroxidation in rats.
2002 May
Absorption and metabolism of antioxidative polyphenolic compounds in red wine.
2002 May
Isolation from a shea cake digester of a tannin-degrading Streptococcus gallolyticus strain that decarboxylates protocatechuic and hydroxycinnamic acids, and emendation of the species.
2002 May
Identification of phenyldecanoic acid as a constituent of triacylglycerols and wax ester produced by Rhodococcus opacus PD630.
2002 May
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
On the application of 4-hydroxybenzoic acid as a trapping agent to study hydroxyl radical generation during cerebral ischemia and reperfusion.
2002 May-Jun
[The nature of melanin pigments from some micro- and macromycetes].
2002 May-Jun
In vitro cytotoxicity of protocatechuic acid to cultured human cells from oral tissue: involvement in oxidative stress.
2002 Nov
Inhibition of TNF-alpha induced cell death in human umbilical vein endothelial cells and Jurkat cells by protocatechuic acid.
2002 Nov
Characterization of five phyllosphere bacteria isolated from Rosa rugosa leaves, and their phenotypic and metabolic properties.
2002 Nov
Oxidation of aromatic substrates in water/goethite slurry by means of hydrogen peroxide.
2002 Nov
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
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
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
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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