| 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].
| [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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