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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(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

HIDE SMILES / InChI

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

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 effects of collagen synthesis inhibitory drugs on somitogenesis and myogenin expression in cultured chick and mouse embryos.
2001 Feb
Polyhydroxybenzoates inhibit ascorbic acid activation of mitochondrial glycerol-3-phosphate dehydrogenase: implications for glucose metabolism and insulin secretion.
2001 Jan 26
Isolation and characterization of novel benzoates, cinnamates, flavonoids, and lignans from Riesling wine and screening for antioxidant activity.
2001 Jun
In vitro activity of polyhydroxycarboxylates against herpesviruses and HIV.
2001 Nov
Positive effect of collagen V and VI on triglyceride accumulation during differentiation in cultures of bovine intramuscular adipocytes.
2002 May
The prolyl 4-hydroxylase inhibitor ethyl-3,4-dihydroxybenzoate generates effective iron deficiency in cultured cells.
2002 Oct 9
Identification of an antioxidant, ethyl protocatechuate, in peanut seed testa.
2003 Apr 9
Activation of the hypoxia-inducible factor-pathway and stimulation of angiogenesis by application of prolyl hydroxylase inhibitors.
2003 Jun
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
Metabolism of xenobiotics in the incubated hen's egg: investigations with ethyl 4-hydroxybenzoate.
2005
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
Stimulation of collagen synthesis by insulin and proteoglycan accumulation by ascorbate in bovine keratocytes in vitro.
2006 Dec
Desferoxamine and ethyl-3,4-dihydroxybenzoate protect myocardium by activating NOS and generating mitochondrial ROS.
2006 Jan
Prolyl hydroxylase inhibitor treatment confers whole-animal hypoxia tolerance.
2007 Jun
Beta-cell alpha-ketoglutarate hydroxylases may acutely participate in insulin secretion.
2008 Aug
Remote renal preconditioning-induced cardioprotection: a key role of hypoxia inducible factor-prolyl 4-hydroxylases.
2008 May
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
[Studies on the chemical constituents of the fruit of Xylocarpus granatum].
2009 Aug
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
Inhibition of extracellular matrix assembly induces the expression of osteogenic markers in skeletal muscle cells by a BMP-2 independent mechanism.
2009 Oct 5
Increase of reactive oxygen species by desferrioxamine during experimental Chagas' disease.
2010
Adipocyte extracellular matrix composition, dynamics and role in obesity.
2010 Apr
Chelation of intracellular iron enhances endothelial barrier function: a role for vitamin C?
2010 Aug 15
Preconditioning protects against oxidative injury involving hypoxia-inducible factor-1 and vascular endothelial growth factor in cultured astrocytes.
2010 May 10
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
Ascorbic acid regulates osterix expression in osteoblasts by activation of prolyl hydroxylase and ubiquitination-mediated proteosomal degradation pathway.
2011 Jun 28
The role of prolyl hydroxylase domain protein (PHD) during rosiglitazone-induced adipocyte differentiation.
2014 Jan 31
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 19:51:01 GMT 2023
Edited
by admin
on Fri Dec 15 19:51:01 GMT 2023
Record UNII
4YGJ96WTBG
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ETHYL PROTOCATECHUATE
Systematic Name English
ETHYL 3,4-DIHYDROXYBENZOATE
Systematic Name English
NSC-86130
Code English
Code System Code Type Description
CAS
3943-89-3
Created by admin on Fri Dec 15 19:51:01 GMT 2023 , Edited by admin on Fri Dec 15 19:51:01 GMT 2023
PRIMARY
EPA CompTox
DTXSID2057732
Created by admin on Fri Dec 15 19:51:01 GMT 2023 , Edited by admin on Fri Dec 15 19:51:01 GMT 2023
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WIKIPEDIA
ETHYL PROTOCATECHUATE
Created by admin on Fri Dec 15 19:51:01 GMT 2023 , Edited by admin on Fri Dec 15 19:51:01 GMT 2023
PRIMARY
NSC
86130
Created by admin on Fri Dec 15 19:51:01 GMT 2023 , Edited by admin on Fri Dec 15 19:51:01 GMT 2023
PRIMARY
CHEBI
132364
Created by admin on Fri Dec 15 19:51:01 GMT 2023 , Edited by admin on Fri Dec 15 19:51:01 GMT 2023
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ECHA (EC/EINECS)
223-529-0
Created by admin on Fri Dec 15 19:51:01 GMT 2023 , Edited by admin on Fri Dec 15 19:51:01 GMT 2023
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PUBCHEM
77547
Created by admin on Fri Dec 15 19:51:01 GMT 2023 , Edited by admin on Fri Dec 15 19:51:01 GMT 2023
PRIMARY
FDA UNII
4YGJ96WTBG
Created by admin on Fri Dec 15 19:51:01 GMT 2023 , Edited by admin on Fri Dec 15 19:51:01 GMT 2023
PRIMARY