| Identification | More | [Name]
Ethyl 3,4-dihydroxybenzoate | [CAS]
3943-89-3 | [Synonyms]
3,4-DIHYDROXYBENZOIC ACID ETHYL ESTER
ETHYL 3,4-DIHYDROXYBENZOATE
ETHYL PROTOCATECHUATE
PROTOCATECHUIC ACID ETHYL ESTER
RARECHEM AL BI 0069
3,4-dihydroxybenzate ethyl ester
3,4-DIHYDROXYBENZOIC ACID ETHYL ESTER 97%
3,4-DIHYDROXYBENZOIC ACID ETHYL ESTER 98+%
ETHYL 3,4-DIHYDROXYBENZOATE (PROTOCATECHUIC ACID ETHYL ESTER)
Benzoic acid, 3,4-dihydroxy-, ethyl ester
EDHB | [EINECS(EC#)]
223-529-0 | [Molecular Formula]
C9H10O4 | [MDL Number]
MFCD00002199 | [Molecular Weight]
182.17 | [MOL File]
3943-89-3.mol |
| Chemical Properties | Back Directory | [Appearance]
pale yellow to beige crystalline powder | [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 Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S37/39:Wear suitable gloves and eye/face protection . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HS Code ]
29053990 |
| Hazard Information | Back Directory | [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. | [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]
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. | [storage]
4°C, stored under nitrogen | [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. |
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