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=C(O)C(O)=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 |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
|||
| Preventing | Unknown Approved UseUnknown |
|||
| Preventing | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| The role of prolyl hydroxylase domain protein (PHD) during rosiglitazone-induced adipocyte differentiation. | 2014-01-31 |
|
| Ascorbic acid regulates osterix expression in osteoblasts by activation of prolyl hydroxylase and ubiquitination-mediated proteosomal degradation pathway. | 2011-06-28 |
|
| Chelation of intracellular iron enhances endothelial barrier function: a role for vitamin C? | 2010-08-15 |
|
| Induction of heme oxygenase-1, biliverdin reductase and H-ferritin in lung macrophage in smokers with primary spontaneous pneumothorax: role of HIF-1alpha. | 2010-05-28 |
|
| Preconditioning protects against oxidative injury involving hypoxia-inducible factor-1 and vascular endothelial growth factor in cultured astrocytes. | 2010-05-10 |
|
| Adipocyte extracellular matrix composition, dynamics and role in obesity. | 2010-04 |
|
| Increase of reactive oxygen species by desferrioxamine during experimental Chagas' disease. | 2010 |
|
| Inhibition of extracellular matrix assembly induces the expression of osteogenic markers in skeletal muscle cells by a BMP-2 independent mechanism. | 2009-10-05 |
|
| [Studies on the chemical constituents of the fruit of Xylocarpus granatum]. | 2009-08 |
|
| 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. | 2009-05 |
|
| 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. | 2008-11 |
|
| Activation of the oxygen-sensing signal cascade prevents mitochondrial injury after mouse liver ischemia-reperfusion. | 2008-10 |
|
| Beta-cell alpha-ketoglutarate hydroxylases may acutely participate in insulin secretion. | 2008-08 |
|
| Remote renal preconditioning-induced cardioprotection: a key role of hypoxia inducible factor-prolyl 4-hydroxylases. | 2008-05 |
|
| Prolyl hydroxylase inhibitors delay neuronal cell death caused by trophic factor deprivation. | 2007-12 |
|
| Prolyl hydroxylase inhibitor treatment confers whole-animal hypoxia tolerance. | 2007-06 |
|
| The prolyl hydroxylase oxygen-sensing pathway is cytoprotective and allows maintenance of mitochondrial membrane potential during metabolic inhibition. | 2007-02 |
|
| Stimulation of collagen synthesis by insulin and proteoglycan accumulation by ascorbate in bovine keratocytes in vitro. | 2006-12 |
|
| Desferoxamine and ethyl-3,4-dihydroxybenzoate protect myocardium by activating NOS and generating mitochondrial ROS. | 2006-01 |
|
| Effects of structure on radical-scavenging abilities and antioxidative activities of tea polyphenols: NMR analytical approach using 1,1-diphenyl-2-picrylhydrazyl radicals. | 2005-05-04 |
|
| Metabolism of xenobiotics in the incubated hen's egg: investigations with ethyl 4-hydroxybenzoate. | 2005 |
|
| Activation of the hypoxia-inducible factor-pathway and stimulation of angiogenesis by application of prolyl hydroxylase inhibitors. | 2003-06 |
|
| 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. | 2003-05-30 |
|
| Identification of an antioxidant, ethyl protocatechuate, in peanut seed testa. | 2003-04-09 |
|
| The prolyl 4-hydroxylase inhibitor ethyl-3,4-dihydroxybenzoate generates effective iron deficiency in cultured cells. | 2002-10-09 |
|
| Positive effect of collagen V and VI on triglyceride accumulation during differentiation in cultures of bovine intramuscular adipocytes. | 2002-05 |
|
| In vitro activity of polyhydroxycarboxylates against herpesviruses and HIV. | 2001-11 |
|
| Isolation and characterization of novel benzoates, cinnamates, flavonoids, and lignans from Riesling wine and screening for antioxidant activity. | 2001-06 |
|
| The effects of collagen synthesis inhibitory drugs on somitogenesis and myogenin expression in cultured chick and mouse embryos. | 2001-02 |
|
| Polyhydroxybenzoates inhibit ascorbic acid activation of mitochondrial glycerol-3-phosphate dehydrogenase: implications for glucose metabolism and insulin secretion. | 2001-01-26 |
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
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Edited
Mon Mar 31 19:58:48 GMT 2025
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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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