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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
Structure of ETHYL PROTOCATECHUATE

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

HIDE SMILES / InChI
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

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Prolyl hydroxylase (human)
0.4 mM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Preventing
Unknown

Approved Use

Unknown
Preventing
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
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
Patents

Sample Use Guides

Mice: 100 mg/kg
Route of Administration: Intraperitoneal
In Vitro Use Guide
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.
Name Type Language
ETHYL PROTOCATECHUATE
Systematic Name English
NSC-86130
Preferred Name English
ETHYL 3,4-DIHYDROXYBENZOATE
Systematic Name English
Code System Code Type Description
CAS
3943-89-3
Created by admin on Mon Mar 31 19:58:48 GMT 2025 , Edited by admin on Mon Mar 31 19:58:48 GMT 2025
PRIMARY
EPA CompTox
DTXSID2057732
Created by admin on Mon Mar 31 19:58:48 GMT 2025 , Edited by admin on Mon Mar 31 19:58:48 GMT 2025
PRIMARY
WIKIPEDIA
ETHYL PROTOCATECHUATE
Created by admin on Mon Mar 31 19:58:48 GMT 2025 , Edited by admin on Mon Mar 31 19:58:48 GMT 2025
PRIMARY
NSC
86130
Created by admin on Mon Mar 31 19:58:48 GMT 2025 , Edited by admin on Mon Mar 31 19:58:48 GMT 2025
PRIMARY
CHEBI
132364
Created by admin on Mon Mar 31 19:58:48 GMT 2025 , Edited by admin on Mon Mar 31 19:58:48 GMT 2025
PRIMARY
ECHA (EC/EINECS)
223-529-0
Created by admin on Mon Mar 31 19:58:48 GMT 2025 , Edited by admin on Mon Mar 31 19:58:48 GMT 2025
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PUBCHEM
77547
Created by admin on Mon Mar 31 19:58:48 GMT 2025 , Edited by admin on Mon Mar 31 19:58:48 GMT 2025
PRIMARY
FDA UNII
4YGJ96WTBG
Created by admin on Mon Mar 31 19:58:48 GMT 2025 , Edited by admin on Mon Mar 31 19:58:48 GMT 2025
PRIMARY