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
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. |
Computed Descriptors for Ethyl 3,4-dihydroxybenzoate
InChIKey | KBPUBCVJHFXPOC-UHFFFAOYSA-N |
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