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
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)
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.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL614731 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28468298 |
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Target ID: CHEMBL2622 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28111996 |
0.048 mM [IC50] | ||
Target ID: CHEMBL2039 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24116298 |
300.0 µM [IC50] | ||
Target ID: CHEMBL3102 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24116298 |
334.0 µM [IC50] | ||
Target ID: CHEMBL205 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21282059 |
470.0 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
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Preventing | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
A transcriptional luxAB reporter fusion responding to fluorene in Sphingomonas sp. LB126 and its initial characterisation for whole-cell bioreporter purposes. | 2001 Dec |
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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 |
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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 |
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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 |
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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 |
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Determination of active ingredients of Rhododendron dauricum L. by capillary electrophoresis with electrochemical detection. | 2002 Jan 11 |
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Multiple operons connected with catabolism of aromatic compounds in Acinetobacter sp. strain ADP1 are under carbon catabolite repression. | 2002 Jul |
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Peroxynitrite scavenging activities of aromatic compounds isolated from Konnyaku, Amorphophallus konjac K.Koch. | 2002 Jun |
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Oxidation of 3,4-dihydroxybenzoic acid by means of hydrogen peroxide in aqueous goethite slurry. | 2002 Jun |
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Hibiscus protocatechuic acid or esculetin can inhibit oxidative LDL induced by either copper ion or nitric oxide donor. | 2002 Mar 27 |
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Inhibition of TNF-alpha induced cell death in human umbilical vein endothelial cells and Jurkat cells by protocatechuic acid. | 2002 Nov |
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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 |
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Characterization of four olive-mill-wastewater indigenous bacterial strains capable of aerobically degrading hydroxylated and methoxylated monocyclic aromatic compounds. | 2002 Sep |
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Oxidative dimers produced from protocatechuic and gallic esters in the DPPH radical scavenging reaction. | 2002 Sep 11 |
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Elucidation of the metabolic pathway of fluorene and cometabolic pathways of phenanthrene, fluoranthene, anthracene and dibenzothiophene by Sphingomonas sp. LB126. | 2003 Apr |
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Antioxidant activity of 3-dehydroshikimic acid in liposomes, emulsions, and bulk oil. | 2003 Apr 23 |
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Degradation of phenanthrene and naphthalene by a Burkholderia species strain. | 2003 Feb |
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Photo-Fenton treatment of water containing natural phenolic pollutants. | 2003 Jan |
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Effect of 4-coumaric and 3,4-dihydroxybenzoic acid on oxidative DNA damage in rat colonic mucosa. | 2003 May |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20506690
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24116298
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
Edited
Fri Jun 25 23:17:30 UTC 2021
by
admin
on
Fri Jun 25 23:17:30 UTC 2021
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Record UNII |
36R5QJ8L4B
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Record Status |
Validated (UNII)
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DB03946
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Protocatechuic acid
Created by
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154.5% reaction on PG synthase w/10.0 mM conc. of compound
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PARENT -> CONSTITUENT ALWAYS PRESENT |
USP
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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ACTIVE MOIETY |
Antiviral
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