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
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)
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.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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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 |
---|---|---|
Medicinal and ethnoveterinary remedies of hunters in Trinidad. | 2001 |
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Purification and properties of p-hydroxybenzoate hydroxylases from Rhodococcus strains. | 2001 Aug |
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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 |
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Molecular mechanisms controlling the rate and specificity of catechol O-methylation by human soluble catechol O-methyltransferase. | 2001 Feb |
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Inhibition of human plasmin activity using humic acids with arsenic. | 2001 Jun 12 |
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Aromatic inhibitors of dehydroquinate synthase: synthesis, evaluation and implications for gallic acid biosynthesis. | 2001 Jun 18 |
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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 |
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Phenolic acids and depsides from some species of the Erodium genera. | 2001 Nov-Dec |
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Kinetic model for phenolic compound oxidation by Fenton's reagent. | 2001 Oct |
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Antimicrobial activity of Argentine plants used in the treatment of infectious diseases. Isolation of active compounds from Sebastiania brasiliensis. | 2001 Sep |
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Genomic analysis of the aromatic catabolic pathways from Pseudomonas putida KT2440. | 2002 Dec |
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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 |
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Spectroscopic and electronic structure studies of protocatechuate 3,4-dioxygenase: nature of tyrosinate-Fe(III) bonds and their contribution to reactivity. | 2002 Jan 30 |
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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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Electroorganic synthesis of new benzofuro[2,3-d]pyrimidine derivatives. | 2002 Jul 12 |
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Enhanced detection and characterization of protocatechuate 3,4-dioxygenase in Acinetobacter lwoffii K24 by proteomics using a column separation. | 2002 Jul 26 |
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Mineralization of aromatic compounds by brown-rot basidiomycetes - mechanisms involved in initial attack on the aromatic ring. | 2002 Jun |
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In vivo protective effect of protocatechuic acid on tert-butyl hydroperoxide-induced rat hepatotoxicity. | 2002 May |
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Antioxidant activity of phenolic compounds isolated from Mesona procumbens Hemsl. | 2002 May 8 |
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[The nature of melanin pigments from some micro- and macromycetes]. | 2002 May-Jun |
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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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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 |
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Effect of naturally occurring plant phenolics on the induction of drug metabolizing enzymes by o-toluidine. | 2003 Apr 15 |
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Hibiscus protocatechuic acid inhibits lipopolysaccharide-induced rat hepatic damage. | 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
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Edited
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Record UNII |
36R5QJ8L4B
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Record Status |
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
154.5% reaction on PG synthase w/10.0 mM conc. of compound
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
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PARENT -> METABOLITE |
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ACTIVE MOIETY |
Antiviral
|