Ethyl-3,4-dihydroxybenzoat

Gefahreninformationscode (GHS)

• Bildanzeige (GHS)

  

• Alarmwort

  Warnung

• Gefahrenhinweise

  H315：Verursacht Hautreizungen.

  H319：Verursacht schwere Augenreizung.

  H335：Kann die Atemwege reizen.

• Sicherheit

  P261：Einatmen von Staub vermeiden.

  P264：Nach Gebrauch gründlich waschen.

  P264：Nach Gebrauch gründlich waschen.

  P271：Nur im Freien oder in gut belüfteten Räumen verwenden.

  P280：Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.

  P302+P352：BEI BERÜHRUNG MIT DER HAUT: Mit viel Wasser/... (Hersteller kann, falls zweckmäßig, ein Reinigungsmittel angeben oder, wenn Wasser eindeutig ungeeignet ist, ein alternatives Mittel empfehlen) waschen.

  P305+P351+P338：BEI KONTAKT MIT DEN AUGEN: Einige Minuten lang behutsam mit Wasser spülen. Eventuell vorhandene Kontaktlinsen nach Möglichkeit entfernen. Weiter spülen.

Ethyl 3,4-dihydroxybenzoate Chemische Eigenschaften,Einsatz,Produktion Methoden

• R-Sätze Betriebsanweisung:

  R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.

• S-Sätze Betriebsanweisung:

  S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
  S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
  S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.

• Beschreibung

  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].

• Chemische Eigenschaften

  pale yellow to beige crystalline powder

• Verwenden

  An antioxidant compound found in Sicilian virgin olive oils and red wines.

• Verwenden

  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.

• Biologische Aktivität

  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].

• Synthese

  

  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.

• Einzelnachweise

  [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 Upstream-Materialien And Downstream Produkte

Ethyl-3,4-dihydroxybenzoat Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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