十六烷酸,2-(4-羟基苯基)乙基酯 | 155623-46-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 十六烷酸,2-(4-羟基苯基)乙基酯
• 英文名称: 2-(4'-hydroxyphenyl)-ethyl palmitate
• 英文别名: 2-(4'-hydroxyphenyl)ethyl palmitate；4-hydroxyphenethyl palmitate；tyrosyl palmitate；2-(4-Hydroxyphenyl)ethyl hexadecanoate
• CAS: 155623-46-4
• 化学式: C₂₄H₄₀O₃
• 分子量: 376.58
• InChiKey: DFQXRQNVYVMYAU-UHFFFAOYSA-N

物化性质

• 沸点：
  491.8±20.0 °C(Predicted)
• 密度：
  0.969±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9
• 重原子数：
  27
• 可旋转键数：
  18
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  十六烷酸,2-(4-羟基苯基)乙基酯 在 三乙胺 、 potassium hydroxide 、 magnesium chloride 作用下， 以 四氢呋喃 、 水 、 异丙醇 、 丙酮 为溶剂， 反应 24.33h， 生成 3,4-bis(ethoxycarbonyloxy)phenethyl palmitate
  参考文献：
  名称：

  HYDROXYTYROSOL DERIVATIVES, THEIR METHOD OF PREPARATION AND USE IN PERSONAL CARE

  摘要：

  披露了羟基酪醇衍生物组合物的制造方法，以及它们在个人护理产品中的应用。脂溶性羟基酪醇碳酸酯化合物可以通过将取代羟基苯甲醛化合物与氧化剂（如过氧化氢）在温和条件下氧化而制得。该过程涉及酶催化的4-(2-羟乙基)酚酯化反应，形成相应的酯化物，将羟基酯的酚羟基正对位引入一个甲酰基，形成一个脂溶性甲酰酪醇酯；将脂溶性甲酰酪醇酯与过氧化物化合物氧化，形成脂溶性羟基酪醇酯化合物；以及将脂溶性羟基酪醇酯化合物与碳酸酯衍生物反应，形成脂溶性羟基酪醇碳酸酯化合物。这些化合物对于各种个人护理产品都很有用，作为抗衰老化合物，具有抗氧化稳定性。

  公开号：

  US20150126759A1
• 作为产物：
  描述：

  棕榈酸甲酯 、 对羟基苯乙醇 在 Candida antarctica lipase B immobilized 作用下， 80.0 ℃ 、80.0 kPa 条件下， 生成 十六烷酸,2-(4-羟基苯基)乙基酯
  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

文献信息

• Convenient Synthesis of Hydroxytyrosol and Its Lipophilic Derivatives from Tyrosol or Homovanillyl Alcohol
  作者：Roberta Bernini、Enrico Mincione、Maurizio Barontini、Fernanda Crisante

  DOI：10.1021/jf801558z

  日期：2008.10.8

  chemoselective protection of the alcoholic group of these compounds was performed by using dimethyl carbonate (DMC) as reagent/solvent; second, the oxidation with 2-iodoxybenzoic acid (IBX) or Dess-Martin periodinane reagent (DMP) and in situ reduction with sodium dithionite (Na2S2O4) allowed the preparation of carboxymethylated hydroxytyrosol; finally, by a mild hydrolytic step, hydroxytyrosol was

  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。
• Hydrolysis and Transport Characteristics of Tyrosol Acyl Esters in Rat Intestine
  作者：Fawen Yin、Xiaopei Hu、Dayong Zhou、Xiaochi Ma、Xiangge Tian、Xiaokui Huo、Kanyasiri Rakariyatham、Fereidoon Shahidi、Beiwei Zhu

  DOI：10.1021/acs.jafc.8b04487

  日期：2018.11.28

  Lipophenols such as palmitoyl esters of green-tea polyphenols (GTP) have been allowed for use as food additives for oxidation control. However, their digestive absorption remains unexplored. In this paper, the hydrolysis and transport characteristics of tyrosol acyl esters (TYr-Es) with various fatty acids (C12:0, C14:0, C16:0, C18:0, C18:1, and C18:2) were evaluated using the everted-rat-gut-sac model

  允许使用脂酚（例如绿茶多酚（GTP）的棕榈酰基酯）作为控制氧化的食品添加剂。然而，它们的消化吸收仍未开发。本文评估了酪醇酰基酯（TYr-Es）与各种脂肪酸（C12：0，C14：0，C16：0，C18：0，C18：1和C18：2）的水解和运输特性首次使用Everted-rat-gut-sac模型。HPLC-UV测量表明TYr-Es水解为TYr，这对TYr跨囊运输起到了重要作用。水解和转运速率与其脂质部分的链长负相关，但与不饱和度呈正相关。一般而言，所有TYr-E均表现出持续释放的行为。所以，
• Monolayer properties of synthesized tyrosyl esters
  作者：Imen Aissa、Julien Leclaire、Yassine Ben Ali、Fakher Frikha、Youssef Gargouri

  DOI：10.1016/j.molcatb.2012.07.002

  日期：2012.11

  Lipase-catalyzed synthesis of eight fatty acid tyrosyl esters (TyC(2) to TyC(18:1)) was investigated using non commercial lipases from Rhizopus oryzae and Staphylococcus xylosus immobilized onto CaCO3. The monomolecular film technique was used to compare the ability of the various synthesized tyrosyl fatty acid esters to form a stable monolayer at the air/water interface and their capacity to interact with a phospholipid monolayer. The measurements of surface pressure versus the molecular area shows that, in contrast to tyrosol esterified with short and medium chains (acetic (TyC(2)), propionic (TyC(3)), caprylic (TyC(8)) and capric (TyC(10)) acids), tyrosol esterified with long chains: lauric (TyC(12)), palmitic (TyC(16)), stearic (TyC(18)) and oleic (TyC(18:1)) acids are able to form a stable monolayer at the air/water interface. A direct correlation was observed between the length of the saturated acyl chain of the derivatives and their corresponding collapse pressures. The presence of unsaturation reduces the collapse pressure value. The interaction of tyrosyl esters with a phospholipid monolayer was studied and the critical surface pressure (pi(c)) of each ester was determined. Only medium and long chain (TyC(8) to TyC(18:1)) derivatives esters were found to interact efficiently with DiC(12)PC film. (C) 2012 Elsevier B.V. All rights reserved.
• HYDROXYTYROSOL DERIVATIVES THEIR METHOD OF PREPARATION AND USE IN PERSONAL CARE
  申请人：Eastman Chemical Company

  公开号：EP3066068A1

  公开（公告）日：2016-09-14
• US9334229B2
  申请人：——

  公开号：US9334229B2

  公开（公告）日：2016-05-10