2-(4'-hydroxy-3'-methoxyphenyl)ethyl oleate | 1037077-63-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-(4'-hydroxy-3'-methoxyphenyl)ethyl oleate
• 英文别名: 2-(4-hydroxy-3-methoxyphenyl)ethyl oleate；2-(4-hydroxy-3-methoxyphenyl)ethyl (Z)-octadec-9-enoate
• CAS: 1037077-63-6
• 化学式: C₂₇H₄₄O₄
• 分子量: 432.644
• InChiKey: TUKGGTRSZGLCDD-KHPPLWFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.52
• 重原子数：
  31.0
• 可旋转键数：
  19.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-(4'-hydroxy-3'-methoxyphenyl)ethyl oleate 在 2-碘酰基苯甲酸 、 sodium dithionite 作用下， 以 甲醇 、 水 为溶剂， 反应 0.58h， 以68%的产率得到hydroxytyrosyl oleate
  参考文献：
  名称：

  从酪醇或高香草醇方便地合成羟基酪醇及其亲脂性衍生物。

  摘要：

  羟基酪醇是一种天然存在的具有抗氧化性能的邻酚类化合物，它是通过三步高产率程序从天然和低成本的化合物（例如酪醇或高香草醇）合成的。首先，通过使用碳酸二甲酯（DMC）作为试剂/溶剂，对这些化合物的醇基进行有效的化学选择性保护。其次，用2-碘氧基苯甲酸（IBX）或Dess-Martin高碘烷试剂（DMP）氧化并用连二亚硫酸钠（Na 2 S 2 O 4）原位还原，可以制备羧甲基化羟基酪醇。最终，通过温和的水解步骤，以高收率和高纯度获得了羟基酪醇，这已通过NMR光谱和HPLC谱图得到了证实。通过类似的方法，亲脂性羟基酪醇衍生物被用作药物，食品，和化妆品制剂，都准备好了。实际上，首先，通过使用酰氯在没有任何催化剂的情况下对酪醇和高香草醇的醇基团进行化学选择性保护，以获得相应的亲脂性衍生物，然后将这些化合物以高收率和高纯度转化为羟基酪醇衍生物。 IBX或DMP和Na2S2O4的氧化/还原途径。

  DOI：

  10.1021/jf801558z
• 作为产物：
  描述：

  油酸 、 4-羟基-3-甲氧基苯乙醇 在 Candida antarctica lipase B immobilized 作用下， 80.0 ℃ 、80.0 kPa 条件下， 生成 2-(4'-hydroxy-3'-methoxyphenyl)ethyl oleate
  参考文献：
  名称：

  Lipophilic (Hydroxy)phenylacetates by Solvent-Free Lipase-Catalyzed Esterification and Transesterification in Vacuo

  摘要：

  Various long-chain alkyl (hydroxy)phenylacetates were prepared in high yield by lipase-catalyzed transesterification of the corresponding short-chain alkyl hydroxyphenyl acetates and fatty alcohols in equimolar ratios. The reactions were performed in vacuo at moderate temperatures in the absence of solvents and drying agents in direct contact with the reaction mixture. Immobilized lipase B from Candida antarctica(Novozym 435) was the most effective biocatalyst for the various transesterification reactions. Generally, Novozym 435-catalyzed transesterifications of short-chain alkyl (hydroxy)phenylacetates with long-chain alcohols led to higher conversions and enzyme activities than the corresponding esterifications. For example, the transesterification activity was up to 4-fold higher than the esterification activity for the formation of oleyl 4-hydroxy-3-methoxyphenylacetate using Novozym 435 as a biocatalyst. The relative transesterification activities were as follows: phenylacetate > 3-methoxyphenylacetate approximate to 4-methoxyphenylacetate > 4-hydroxy-3-methoxyphenylacetate > 3-hydroxyphenylacetate approximate to 4-hydroxyphenylacetate >> 2-methoxyphenylacetate >> 3,4-dihydroxyphenylacetate. With respect to the position of methoxy and hydroxy substituents, the transesterification activity of Novozym 435 decreased in the order meta approximate to para >> ortho. Compounds with inverse chemical structures, for example, tyrosyl oleate, were obtained by Novozym 435-catalyzed esterification and transesterification of fatty acids and their methyl esters, respectively, with 2-phenylethan-1-ols. In contrast to the transesterifications of short-chain alkyl (hydroxy)phenylacetates with fatty alcohols, higher conversions and enzyme activities were observed for the Novozym 435-catalyzed esterifications of (hydroxy)phenylethanols with long-chain fatty acids than the corresponding transesterifications with fatty acid methyl esters.

  DOI：

  10.1021/jf8002224