Ethyl 3,4-dihydroxybenzoate Property

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

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29053990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Ethyl 3,4-dihydroxybenzoate Chemical Properties,Usage,Production

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.