hydroxytyrosol decanoate

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: hydroxytyrosol decanoate
• 英文别名: hydroxytyrosol decanoate ester；hydroxytyrosyl decanoate；decanoic acid-3,4-dihydroxyphenylethyl ester；2-(3,4-dihydroxyphenyl)ethyl decanoate
• 化学式: C₁₈H₂₈O₄
• 分子量: 308.418
• InChiKey: NQBXMEBFYHFAIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 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：

  3,4-二羟基苯乙酸 在 硫酸 、 erbium(III) triflate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 23.0h， 生成 hydroxytyrosol decanoate
  参考文献：
  名称：

  Lipophilic Hydroxytyrosol Esters: Fatty Acid Conjugates for Potential Topical Administration

  摘要：

  Hydroxytyrosol is a potent antioxidant natural molecule isolated from olive leaves and fruits. The presence of three hydroxy groups in its structure poses a limit for the topical application of this lead compound. A set of hydroxytyrosol conjugates with fatty acids at different molecular weights were synthesized under mild conditions. The topical delivery features of this new set of antioxidant molecules were evaluated as a function of their permeation profiles through the human stratum corneum and viable epidermis membranes. A dependence on their partition coefficients, their molecular weights, and their isometric configurations was then postulated. Encouraging results prompt further investigations on the polyfunctional role that hydroxytyrosol conjugates could have as agents in both anti-inflammatory and antioxidant therapies.

  DOI：

  10.1021/np200405s

文献信息

• Tyrosol and hydroxytyrosol derivatives as antitrypanosomal and antileishmanial agents
  作者：Efres Belmonte-Reche、Marta Martínez-García、Pablo Peñalver、Verónica Gómez-Pérez、Ricardo Lucas、Francisco Gamarro、José María Pérez-Victoria、Juan Carlos Morales

  DOI：10.1016/j.ejmech.2016.04.047

  日期：2016.8

  Existing treatments have considerable side effects and increase resistance of the parasites. We have measured antitrypanosomal and antileishmanial activity of natural phenols, tyrosol (TYR) and hydroxytyrosol (HT) and several of their esters and metabolites. We found significant IC50 values against Trypanosoma brucei for HT decanoate ester and HT dodecanoate ester (0.6 and 0.36 μM, respectively). This represents

  锥虫病和利什曼病一直是非洲国家健康和发展的真正挑战。现有疗法具有相当大的副作用并增加了寄生虫的抵抗力。我们已经测量了天然酚，酪醇（TYR）和羟基酪醇（HT）以及它们的一些酯和代谢物的抗胰锥虫和抗疟疾活性。我们发现针对布鲁氏锥虫的有效IC 50值用于HT癸酸酯和HT十二酸酯（分别为0.6和0.36μM）。这表示相对于HT的活性大大增加（分别为79和132倍）。此外，两种化合物均对非肿瘤性人类细胞系MRC-5（分别为118和106）表现出高选择性。然后，我们合成了一个有针对性的化合物库，以探索结构活性。我们发现HT癸酸酯和HT十二酸酯的醚和硫脲类似物在低微摩尔范围内也显示出针对布鲁氏杆菌的IC 50值。总之，二邻苯酚环和中等大小的烷基链对于活性至关重要，而它们之间化学键的性质似乎不太重要。
• Lipase-Produced Hydroxytyrosyl Eicosapentaenoate is an Excellent Antioxidant for the Stabilization of Omega-3 Bulk Oils, Emulsions and Microcapsules
  作者：Taiwo Akanbi、Colin Barrow

  DOI：10.3390/molecules23020275

  日期：——

  In this study, several lipophilic hydroxytyrosyl esters were prepared enzymatically using immobilized lipase from Candida antarctica B. Oxidation tests showed that these conjugates are excellent antioxidants in lipid-based matrices, with hydroxytyrosyl eicosapentaenoate showing the highest antioxidant activity. Hydroxytyrosyl eicosapentaenoate effectively stabilized bulk fish oil, fish-oil-in-water emulsions and microencapsulated fish oil. The stabilizing effect of this antioxidant may either be because it orients itself with the omega-3 fatty acids in the oil, thereby protecting them against oxidation, or because this unstable fatty acid can preferentially oxidise, thus providing an additional mechanism of antioxidant protection. Hydroxytyrosyl eicosapentaenoate itself was stable for one year when stored at −20 °C.

  在本研究中，采用来自南极酵母B的固定化脂肪酶酶法制备了几种亲脂性羟基酪醇酯。氧化测试表明，这些结合物在脂质基质中表现出优异的抗氧化性能，其中羟基酪醇二十烯酸酯展现出最高的抗氧化活性。羟基酪醇二十烯酸酯有效稳定了大宗鱼油、鱼油水乳液和微胶囊鱼油。该抗氧化剂的稳定作用可能是因为它与油中的 omega-3 脂肪酸排列在一起，从而保护它们免受氧化，或者是因为这种不稳定的脂肪酸能够优先氧化，从而提供额外的抗氧化保护机制。羟基酪醇二十烯酸酯在 -20 °C 存储时本身稳定性可达一年。
• 10.1039/d4gc02467b
  作者：Wang, Kang-Hong、Yang, Cheng、Liang, Guo-Bin、Meng, Ying-Fen、Zou, Yong、Li, Shuangfei、Yang, Zhen

  DOI：10.1039/d4gc02467b

  日期：——

  instead of a secondary/primary one as the hydrogen bond acceptor (HBA). Inverse correlations were found between enzyme activity and the polarity and viscosity of the HDES. Carboxylic acid-based eutectic solvents can play a dual role as both a reaction medium and a substrate reservoir for the acylation reaction. These findings provide valuable guidelines for selecting HDESs for biocatalytic applications.

  疏水性低共熔溶剂 (HDES) 是新一代与水不混溶的溶剂，已显示出作为生物催化应用的绿色和可持续反应介质的潜力。本研究以Novozym 435（固定在丙烯酸树脂上的南极假丝酵母脂肪酶B）催化的酪醇和羟基酪醇的酯化反应为模型反应，探讨使用HDES作为酰化反应溶剂的可行性以及组分和理化性质的影响HDES 对酶性能的影响。筛选了 21 个 HDES。在 HDES 中反应 2 小时内收率高达 95.1%，与有机溶剂中获得的结果相当甚至更好。包含叔醇而不是仲醇/伯醇作为氢键受体（HBA）的HDES有利于酶促反应。酶活性与 HDES 的极性和粘度之间存在负相关。羧酸基低共熔溶剂可以起到酰化反应的反应介质和底物储存库的双重作用。这些发现为选择用于生物催化应用的 HDES 提供了宝贵的指导。
• Hydroxytyrosol lipophilic analogues: Enzymatic synthesis, radical scavenging activity and DNA oxidative damage protection
  作者：Salvatore Grasso、Laura Siracusa、Carmela Spatafora、Marcella Renis、Corrado Tringali

  DOI：10.1016/j.bioorg.2006.09.003

  日期：2007.4

  The olive oil phenol hydroxytyrosol (3), as well its metabolite homovanillic alcohol (4), were subjected to chemoselective lipase-catalysed acylations, affording with good yield 10 derivatives (5-14) bearing C-2, C-3, C-4, C-10 and C-18 acyl chains at C-1. Hydroxytyrosol (3) and its lipophilic derivatives showed very good DPPH radical scavenging activity. Compounds 3, 4 and their lipophilic analogues 5-14 were subjected to the atypical Comet test on whole blood cells: 3 and its analogues 5 and 6, with little hydrophobic character (logP <= 1.20), showed a good protective effect against H2O2 induced oxidative DNA damage. The homovanillic alcohol 4 and its analogues 10-14 resulted scarcely effective both as radical scavengers and antioxidant agents. (c) 2006 Elsevier Inc. All rights reserved.
• Surface-Active Properties of Lipophilic Antioxidants Tyrosol and Hydroxytyrosol Fatty Acid Esters: A Potential Explanation for the Nonlinear Hypothesis of the Antioxidant Activity in Oil-in-Water Emulsions
  作者：Ricardo Lucas、Francisco Comelles、David Alcántara、Olivia S. Maldonado、Melanie Curcuroze、Jose L. Parra、Juan C. Morales

  DOI：10.1021/jf1009928

  日期：2010.7.14

  Our group has recently observed a nonlinear tendency in antioxidant capacity of different hydroxytyrosol fatty acid esters in fish oil-in-water emulsions, where a maximum of antioxidant efficiency appeared for hydroxytyrosol octanoate. These results appear to disagree with the antioxidant polar paradox. Because the physical location of the antioxidants in an oil water interface has been postulated as an important factor in explaining this behavior, we have prepared a series of tyrosol and hydroxytyrosol fatty acid esters with different chain length and studied their surface-active properties in water, because these physicochemical parameters could be directly related to the preferential placement at the interface. We have found that tyrosol and hydroxytyrosol fatty acid esters are relevant surfactants when the right hydrophilic-lipophilic balance (HLB) is attained and, in some cases, as efficient as emulsifiers commonly used in industry, such as Brij 30 or Tween 20. Moreover, a nonlinear dependency of surfactant effectiveness is observed with the increase in chain length of the lipophilic antioxidants. This tendency seems to fit quite well with the reported antioxidant activity in emulsions, and the best antioxidant of the series (hydroxytyrosol octanoate) is also a very effective surfactant. This potential explanation of the nonlinear hypothesis will help in the rational design of antioxidants used in oil-in-water emulsions.