Ethyl 3,4-dihydroxybenzoate

Synonym(s):Ethyl 3,4-dihydroxybenzoate

CAS NO.：3943-89-3
Empirical Formula: C9H10O4
Molecular Weight: 182.17
MDL number: MFCD00002199
EINECS: 223-529-0
SAFETY DATA SHEET (SDS)
Update Date: 2025-12-05 14:33:18

What is Ethyl 3,4-dihydroxybenzoate?

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

The Uses of Ethyl 3,4-dihydroxybenzoate

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

The Uses of Ethyl 3,4-dihydroxybenzoate

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

What are the applications of Application

Protocatechuic acid ethyl ester is an antioxidant

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.

Properties of Ethyl 3,4-dihydroxybenzoate

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)
pka	8.19±0.18(Predicted)
form	Crystalline Powder
color	Pale yellow to beige
Odor	at 100.00?%. phenolic
Water Solubility	Insoluble in water. Soluble in ethanol.
BRN	2097435
CAS DataBase Reference	3943-89-3(CAS DataBase Reference)
NIST Chemistry Reference	Benzoic acid, 3,4-dihydroxy-, ethyl ester(3943-89-3)

Safety information for Ethyl 3,4-dihydroxybenzoate

Signal word	Warning
Pictogram(s)	Exclamation Mark Irritant GHS07
GHS Hazard Statements	H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes	P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P271:Use only outdoors or in a well-ventilated area. P280:Wear protective gloves/protective clothing/eye protection/face protection. P302+P352:IF ON SKIN: wash with plenty of soap and water. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.