Details
Stereochemistry | ACHIRAL |
Molecular Formula | C9H10O4 |
Molecular Weight | 182.1733 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCOC(=O)C1=CC(O)=C(O)C=C1
InChI
InChIKey=KBPUBCVJHFXPOC-UHFFFAOYSA-N
InChI=1S/C9H10O4/c1-2-13-9(12)6-3-4-7(10)8(11)5-6/h3-5,10-11H,2H2,1H3
Molecular Formula | C9H10O4 |
Molecular Weight | 182.1733 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Ethyl protocatechuate (ethyl 3,4-dihydroxybenzoate) is a lipophilic compound that acts as a pharmacological hypoxic mimetic and prolyl hydroxylase inhibitor. It might serves as a potential anti-fibrotic agent - the synthesis of 4-hydroxyproline in scleroderma cell cultures was reduced by ethyl 3,4-dihydroxybenzoate. Pharmacological activation of the PHD/HIF-1 alpha pathway by a cell-permeable ethyl-3,4 dihydroxybenzoate prevents mitochondrial dysfunction after warm ischemia-reperfusion in vivo. ethyl 3,4-dihydroxybenzoate might prove useful clinically to decrease or eliminate IR injury associated with liver surgery and transplantation. Ethyl protocatechuate supplementation effectively scaled down hypobaric hypoxia induced cerebral edema with concomitant downregulation of brain NF-κB expression – it might serves as effective hypoxic preconditioning agent in ameliorating hypobaric hypoxia mediated injury in brain.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: Prolyl hydroxylase (human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/3036858 |
0.4 mM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Preventing | Unknown Approved UseUnknown |
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Preventing | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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The effects of collagen synthesis inhibitory drugs on somitogenesis and myogenin expression in cultured chick and mouse embryos. | 2001 Feb |
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Polyhydroxybenzoates inhibit ascorbic acid activation of mitochondrial glycerol-3-phosphate dehydrogenase: implications for glucose metabolism and insulin secretion. | 2001 Jan 26 |
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Isolation and characterization of novel benzoates, cinnamates, flavonoids, and lignans from Riesling wine and screening for antioxidant activity. | 2001 Jun |
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In vitro activity of polyhydroxycarboxylates against herpesviruses and HIV. | 2001 Nov |
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Positive effect of collagen V and VI on triglyceride accumulation during differentiation in cultures of bovine intramuscular adipocytes. | 2002 May |
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The prolyl 4-hydroxylase inhibitor ethyl-3,4-dihydroxybenzoate generates effective iron deficiency in cultured cells. | 2002 Oct 9 |
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Identification of an antioxidant, ethyl protocatechuate, in peanut seed testa. | 2003 Apr 9 |
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Activation of the hypoxia-inducible factor-pathway and stimulation of angiogenesis by application of prolyl hydroxylase inhibitors. | 2003 Jun |
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Activation of the prolyl hydroxylase oxygen-sensor results in induction of GLUT1, heme oxygenase-1, and nitric-oxide synthase proteins and confers protection from metabolic inhibition to cardiomyocytes. | 2003 May 30 |
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Metabolism of xenobiotics in the incubated hen's egg: investigations with ethyl 4-hydroxybenzoate. | 2005 |
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Effects of structure on radical-scavenging abilities and antioxidative activities of tea polyphenols: NMR analytical approach using 1,1-diphenyl-2-picrylhydrazyl radicals. | 2005 May 4 |
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Stimulation of collagen synthesis by insulin and proteoglycan accumulation by ascorbate in bovine keratocytes in vitro. | 2006 Dec |
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Desferoxamine and ethyl-3,4-dihydroxybenzoate protect myocardium by activating NOS and generating mitochondrial ROS. | 2006 Jan |
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Prolyl hydroxylase inhibitor treatment confers whole-animal hypoxia tolerance. | 2007 Jun |
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Beta-cell alpha-ketoglutarate hydroxylases may acutely participate in insulin secretion. | 2008 Aug |
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Remote renal preconditioning-induced cardioprotection: a key role of hypoxia inducible factor-prolyl 4-hydroxylases. | 2008 May |
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A prolyl-hydroxylase inhibitor, ethyl-3,4-dihydroxybenzoate, induces haem oxygenase-1 expression in human cells through a mechanism independent of hypoxia-inducible factor-1alpha. | 2008 Nov |
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[Studies on the chemical constituents of the fruit of Xylocarpus granatum]. | 2009 Aug |
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Prolyl hydroxylase inhibitors depend on extracellular glucose and hypoxia-inducible factor (HIF)-2alpha to inhibit cell death caused by nerve growth factor (NGF) deprivation: evidence that HIF-2alpha has a role in NGF-promoted survival of sympathetic neurons. | 2009 May |
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Inhibition of extracellular matrix assembly induces the expression of osteogenic markers in skeletal muscle cells by a BMP-2 independent mechanism. | 2009 Oct 5 |
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Increase of reactive oxygen species by desferrioxamine during experimental Chagas' disease. | 2010 |
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Adipocyte extracellular matrix composition, dynamics and role in obesity. | 2010 Apr |
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Chelation of intracellular iron enhances endothelial barrier function: a role for vitamin C? | 2010 Aug 15 |
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Preconditioning protects against oxidative injury involving hypoxia-inducible factor-1 and vascular endothelial growth factor in cultured astrocytes. | 2010 May 10 |
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Induction of heme oxygenase-1, biliverdin reductase and H-ferritin in lung macrophage in smokers with primary spontaneous pneumothorax: role of HIF-1alpha. | 2010 May 28 |
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Ascorbic acid regulates osterix expression in osteoblasts by activation of prolyl hydroxylase and ubiquitination-mediated proteosomal degradation pathway. | 2011 Jun 28 |
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The role of prolyl hydroxylase domain protein (PHD) during rosiglitazone-induced adipocyte differentiation. | 2014 Jan 31 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18772364
Mice: 100 mg/kg
Route of Administration:
Intraperitoneal
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3036858
The relative collagen synthesis in keloid fibroblast cell cultures incubated with 0.4 mM ethyl-3,4-dihydroxybenzoate was reduced
to 26.1 % (mean & S.D.) of the controls incubated without inhibitor.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 19:51:01 GMT 2023
by
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on
Fri Dec 15 19:51:01 GMT 2023
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Record UNII |
4YGJ96WTBG
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Record Status |
Validated (UNII)
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Record Version |
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