Ethyl 3,4-dihydroxybenzoate Chemical Properties

Melting point:

132-134 °C(lit.)

Boiling point:

275.56°C (rough estimate)

Density 

1.2481 (rough estimate)

vapor pressure 

0-9.4Pa at 20-120℃

refractive index 

1.4500 (estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Crystalline Powder

pka

8.19±0.18(Predicted)

color 

Pale yellow to beige

Odor

at 100.00?%. phenolic

Water Solubility 

Insoluble in water. Soluble in ethanol.

BRN 

2097435

InChIKey

KBPUBCVJHFXPOC-UHFFFAOYSA-N

LogP

1.4 at 35℃ and pH6.6

Surface tension

74.7mN/m at 1g/L and 20℃

CAS DataBase Reference

3943-89-3(CAS DataBase Reference)

NIST Chemistry Reference

Benzoic acid, 3,4-dihydroxy-, ethyl ester(3943-89-3)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29053990

MSDS

• Language:English Provider:Ethyl 3,4-dihydroxybenzoate
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Ethyl 3,4-dihydroxybenzoate Usage And Synthesis

Description

Ethyl 3,4-dihydroxybenzoate (EDHB) is an analogue of 2-oxoglutarate and thus a competitive inhibitor of prolyl hydroxylase domain enzymes (PHDs). It is known as protocatechuic acid and is present in plant foods such as olives, roselle, du-zhong, and white grape wine.This compound have antioxidant, cardioprotective, neuroprotective, antimicrobial, anti-inflammatory and myoprotective activity, as well as anti-ulcer activity[1].

Chemical Properties

pale yellow to beige crystalline powder

Uses

An antioxidant compound found in Sicilian virgin olive oils and red wines.

Uses

The compound is a prolyl 4-hydroxylase inhibitor and can be used to protect the myocardium.

Definition

ChEBI: An ethyl ester resulting from the formal condensation of the carboxy group of 3,4-dihydroxybenzoic acid with ethanol. It is the anti-oxidative component of peanut seed testa.

Biological Activity

Ethyl 3,4-dihydroxybenzoate (EDHB) contains reducible polyphenol hydroxyl groups and exhibits antioxidant activity. Recent studies have shown that EDHB acts as an analog of the substrate α-ketoglutarate and competes for prolyl-hydroxylase activity, thus acting as an inhibitor and effectively inhibiting collagen synthesis and breast cancer metastasis. In addition, in vitro and animal studies in a cerebral ischemic rat model have revealed that EDHB shows increased protective effects and improves rat behavior by inhibiting free radical damage[2].

References

[1] Charu Nimker. "Ethyl 3,4-dihydroxy benzoate, a unique preconditioning agent for alleviating hypoxia-mediated oxidative damage in L6 myoblasts cells." Journal of Physiological Sciences 65 1 (2015): 77–87.
[2] Bo Han. "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): e107204.

Ethyl 3,4-dihydroxybenzoate(3943-89-3)Related Product Information

• 4-Quinazolinamine,N-(3-ethenylphenyl)-6,7-bis(2-methoxyethoxy)-,hydrochloride(1:1)
• Ethyl benzoate
• Erlotinib Imp.15
• Erlotinib Imp.5
• Erlotinib Impurity 20
• Erlotinib Impurity 30
• Erlotinib Impurity 38
• Erlotinib Impurity 25
• Erlotinib Impurity 3
• OSI 413
• Erlotinib Imp.12
• 4-ETHYNYLANILINE
• Erlotinib Impurity 35
• Erlotinib Impurity 20
• Erlotinib Impurity 27
• 4-CHLORO-7-(2-CHLORO-ETHOXY)-6-(2-METHOXY-ETHOXY)-QUINAZOLINE
• Ethyl 3,4-bis(2-methoxyethoxy)benzoate
• Erlotinib iMpurity B