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Ethyl 3,4-dihydroxybenzoate

Ethyl 3,4-dihydroxybenzoate (Protocatechuic acid ethyl ester) is an orally effective, blood-brain barrier-permeable, competitive prolyl hydroxylase (PHD) inhibitor that inhibits the hydroxylation modification of hypoxia-inducible factor (HIF) by PHD. Ethyl 3,4-dihydroxybenzoate stabilizes HIF-1α by inhibiting PHD, activates downstream pathways to induce autophagy and apoptosis of tumor cells, and regulates inflammatory responses, inhibits the NF-κB pathway, improves vascular permeability, and promotes osteoblast differentiation. Ethyl 3,4-dihydroxybenzoate has anti-tumor, anti-hypoxic injury, and bone metabolism regulation effects. It can also be used in the research of cardiovascular protection (such as reducing myocardial ischemic damage), bone tissue engineering (promoting osteogenesis/inhibiting osteoclast differentiation), and prevention and treatment of high-altitude cerebral edema[1][2][3][4].

Product Specifications

CAS Number

[3943-89-3]

Product Name Alternative

Protocatechuic acid ethyl ester

UNSPSC

12352005

Hazard Statement

H315, H319, H335

Target

Apoptosis; Autophagy; HIF/HIF Prolyl-Hydroxylase; NO Synthase; Reactive Oxygen Species (ROS)

Type

Natural Products

Related Pathways

Apoptosis; Autophagy; Immunology/Inflammation; Metabolic Enzyme/Protease; NF-κB

Applications

Cancer-programmed cell death

Field of Research

Cancer; Metabolic Disease

Assay Protocol

https://www.medchemexpress.com/ethyl-3-4-dihydroxybenzoate.html

Purity

99.96

Solubility

DMSO : 100 mg/mL (ultrasonic)

Smiles

O=C(OCC)C1=CC=C(O)C(O)=C1

Molecular Formula

C9H10O4

Molecular Weight

182.18

Precautions

H315, H319, H335

References & Citations

[1]Bo Han, et al. A prolyl-hydroxylase inhibitor, ethyl-3,4-dihydroxybenzoate, induces cell autophagy and apoptosis in esophageal squamous cell carcinoma cells via up-regulation of BNIP3 and N-myc downstream-regulated gene-1. PLoS One. 2014 Sep 18;9 (9) :e107204.|[2]Sebastian Philipp, et al. Desferoxamine and ethyl-3,4-dihydroxybenzoate protect myocardium by activating NOS and generating mitochondrial ROS. Am J Physiol Heart Circ Physiol. 2006 Jan;290 (1) :H450-7.|[3]Byeong-Ju Kwon, et al. Ethyl-3,4-dihydroxybenzoate with a dual function of induction of osteogenic differentiation and inhibition of osteoclast differentiation for bone tissue engineering. Tissue Eng Part A. 2014 Nov;20 (21-22) :2975-84.|[4]Singh DP, et al. Ethyl 3,4-dihydroxybenzoate (EDHB) : a prolyl hydroxylase inhibitor attenuates acute hypobaric hypoxia mediated vascular leakage in brain. J Physiol Sci. 2016 Jul;66 (4) :315-26.

Shipping Conditions

Room Temperature

Storage Conditions

4°C (Powder, stored under nitrogen)

Scientific Category

Natural Products

Clinical Information

No Development Reported

Curated Selection

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