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HomeProduct name listEthyl 3,4-dihydroxybenzoate

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: 2024-08-21 22:41:43
Ethyl 3,4-dihydroxybenzoate Structural

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)
ghs
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.

Computed Descriptors for Ethyl 3,4-dihydroxybenzoate

InChIKey KBPUBCVJHFXPOC-UHFFFAOYSA-N

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