Ethyl 3,4-dihydroxybenzoate
- Product Name
- Ethyl 3,4-dihydroxybenzoate
- CAS No.
- 3943-89-3
- Chemical Name
- Ethyl 3,4-dihydroxybenzoate
- Synonyms
- ETHYL PROTOCATECHUATE;PROTOCATECHUIC ACID ETHYL ESTER;3,4-DIHYDROXYBENZOIC ACID ETHYL ESTER;EDHB;NSC 86130;NSC 619681;3,4-2-ethyl;ERLOTINIBINT-A;RARECHEM AL BI 0069;Ethyl 3,4-dihydroxyb
- CBNumber
- CB0175010
- Molecular Formula
- C9H10O4
- Formula Weight
- 182.17
- MOL File
- 3943-89-3.mol
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.
N-Bromosuccinimide Price
- Product number
- E24859
- Product name
- Protocatechuic acid ethyl ester
- Purity
- 97%
- Packaging
- 5g
- Price
- $45.2
- Updated
- 2025/07/31
- Product number
- D0571
- Product name
- Ethyl 3,4-Dihydroxybenzoate
- Purity
- >98.0%(GC)(T)
- Packaging
- 5g
- Price
- $28
- Updated
- 2025/07/31
- Product number
- D0571
- Product name
- Ethyl 3,4-Dihydroxybenzoate
- Purity
- >98.0%(GC)(T)
- Packaging
- 25g
- Price
- $70
- Updated
- 2025/07/31
- Product number
- E678500
- Product name
- Ethyl 3,4-Dihydroxybenzoate
- Packaging
- 50g
- Price
- $125
- Updated
- 2021/12/16
- Product number
- FD02005
- Product name
- 3,4-Dihydroxybenzoic acid ethyl ester
- Packaging
- 50g
- Price
- $65
- Updated
- 2021/12/16
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].
Synthesis
99-50-3
64-17-5
3943-89-3
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 Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from Ethyl 3,4-dihydroxybenzoate manufacturers
- Product
- Ethyl 3,4-dihydroxybenzoate 3943-89-3
- Price
- US $5.00/kg
- Min. Order
- 1kg
- Purity
- 0.99
- Supply Ability
- 10000
- Release date
- 2024-08-16
- Product
- Ethyl 3,4-dihydroxybenzoate 3943-89-3
- Price
- US $10.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 10 mt
- Release date
- 2024-11-18
- Product
- Ethyl 3,4-dihydroxybenzoate 3943-89-3
- Price
- US $10.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 20 ton
- Release date
- 2024-11-20