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].

Synthesis

General procedure for the synthesis of ethyl 3,4-dihydroxybenzoate from 3,4-dihydroxybenzoic acid and ethanol: 3,4-dihydroxybenzoic acid (5.0 g, 32.0 mmol) was placed in a round-bottomed flask, and 40 mL of anhydrous ethanol was added, and the temperature was slowly elevated to 40°C. The reaction was carried out in the following manner. Under stirring, 5 mL of concentrated sulfuric acid was added dropwise. After the dropwise addition, the reaction system was warmed up to 80 °C, and the reaction was kept at reflux for 10 hours. After completion of the reaction, the reaction solution was cooled to room temperature and the pH was adjusted to neutral with 10 M potassium hydroxide solution. Subsequently, the solvent was removed by distillation under reduced pressure and the resulting solid was washed with a small amount of cold water to afford the target product ethyl 3,4-dihydroxybenzoate. The product was a white solid in 89% yield.

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