3-(3,4-dihydroxyphenyl)propyl hexanoate | 1390634-15-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3-(3,4-dihydroxyphenyl)propyl hexanoate
• CAS: 1390634-15-7
• 化学式: C₁₅H₂₂O₄
• 分子量: 266.337
• InChiKey: SUYFBWHTNYHKHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  在 2-碘酰基苯甲酸 、 sodium dithionite 作用下， 以 甲醇 、 水 为溶剂， 反应 1.08h， 生成 3-(3,4-dihydroxyphenyl)propyl hexanoate
  参考文献：
  名称：

  Synthesis and Structure/Antioxidant Activity Relationship of Novel Catecholic Antioxidant Structural Analogues to Hydroxytyrosol and Its Lipophilic Esters

  摘要：

  A large panel of novel catecholic antioxidants and their fatty acid or methyl carbonate esters has been synthesized in satisfactory to good yields through a 2-iodoxybenzoic acid (IBX)-mediated aromatic hydroxylation as the key step. The new catechols are structural analogues of naturally occurring hydroxytyrosol (3,4-DHE). To evaluate structure/activity relationships, the antioxidant properties of all catecholic compounds were evaluated in vitro by ABTS assay and on whole cells by DCF fluorometric assay and compared with that of the corresponding already known hydroxytyrosyl derivatives. Results outline that all of the new catechols show antioxidant capacity in vitro higher than that of the corresponding hydroxytyrosyl derivatives. Less evident positive effects have been detected in whole cells experiments. Cytotoxicity experiments, using MTT assay, on a representative set of compounds evidenced no influence in cell survival.

  DOI：

  10.1021/jf301131a

文献信息

• Enzymatic continuous-flow preparation of nature-inspired phenolic esters as antiradical and antimicrobial agents
  作者：Francesca Annunziata、Martina L. Contente、Valentina Anzi、Silvia Donzella、Paola Conti、Francesco Molinari、Piera Anna Martino、Gabriele Meroni、Valerio Massimo Sora、Lucia Tamborini、Andrea Pinto

  DOI：10.1016/j.foodchem.2022.133195

  日期：2022.10

  A collection of nature-inspired lipophilic phenolic esters have been prepared by an enzymatic synthesis under flow conditions, using the immobilized lipase B from Candida antarctica (Novozyme 435®) as a catalyst in cyclopentyl methyl ether (CPME), a non-conventional and green solvent. Their antimicrobial activity against four selected bacterial strains together with their efficiency as radical scavengers

  使用来自南极假丝酵母的固定化脂肪酶 B (Novozyme 435®) 作为环戊基甲基醚 (CPME) 中的催化剂，在流动条件下通过酶促合成制备了一系列受自然启发的亲脂性酚酸酯， CPME 是一种非常规和绿色的溶剂。评估了它们对四种选定细菌菌株的抗菌活性以及它们作为自由基清除剂的效率。与母体非酯化化合物相比，所得化合物的特点是亲脂性增强，这增加了它们在食品工业中用作添加剂的可能性。