hydroxytyrosyl stearate

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: hydroxytyrosyl stearate
• 英文别名: 2-(3,4-dihydroxyphenyl)-ethyl stearate；Hydroxytyrosol Sterate；2-(3,4-dihydroxyphenyl)ethyl octadecanoate
• 化学式: C₂₆H₄₄O₄
• 分子量: 420.633
• InChiKey: HSBOLPVTXXRUOM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  30
• 可旋转键数：
  20
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 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 hydroxytyrosyl stearate
  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

• Natural compounds and their derivatives for the prevention and treatment of cardiovascular, hepatic and renal diseases and for cosmetic applications
  申请人：——

  公开号：US20030225160A1

  公开（公告）日：2003-12-04

  The present invention refers to the use of phenolic compounds and their derivatives represented by formula I wherein R 1 and R 2 are selected from among: OH, OCOalkyl, or OCOalkenyl, and R 3 is either H, OH, OCOalkyl or OCOalkenyl, wherein the alkyl or alkenyl chains present from 2 to 22 carbon atoms and wherein at least one OCOalkyl or OCOalkenyl group is present in the structure, for the prevention and treatment of cardiovascular, hepatic or renal diseases, as well as to their cosmetic applications, to compositions that include these compounds and to some novel phenolic compounds and derivatives.

  本发明涉及酚类化合物及其衍生物的使用，其表示为公式I，其中R1和R2从以下选项中选择：OH、OCO烷基或OCO烯基，R3为H、OH、OCO烷基或OCO烯基，其中烷基或烯基链含有2至22个碳原子，并且结构中至少存在一个OCO烷基或OCO烯基基团，用于预防和治疗心血管、肝脏或肾脏疾病，以及它们的化妆品应用，包括这些化合物的组合物和一些新型酚类化合物和衍生物。
• 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。
• Chemoenzymatic synthesis of hydroxytyrosol monoesters and their suppression effect on nitric oxide production stimulated by lipopolysaccharides
  作者：Ayaka Sakakura、Martin Pauze、Atsuhiro Namiki、Megumi Funakoshi-Tago、Hiroomi Tamura、Kengo Hanaya、Shuhei Higashibayashi、Takeshi Sugai

  DOI：10.1080/09168451.2018.1530970

  日期：2019.2.1

  over phenolic hydroxy group in tyrosol, and 2-iodoxybenzoic acid (IBX)-mediated hydroxylation adjacent to the remaining free phenolic hydroxy group. Examination of their suppression effects on nitric oxide production stimulated by lipopolysaccharides in RAW264.7 cells showed that hydroxytyrosol butyrate exhibited the highest inhibition (IC50 7.0 μM) among the tested compounds.

  羟基酪醇[2-（3,4-二羟基苯基）乙醇]的脂肪酸单酯是由酪醇（4-羟基苯基乙醇）分两步通过连续念珠菌南极脂肪酶B催化酚基羟基上的伯脂族羟基的化学选择性酰化反应而合成的。酪醇和2-碘氧基苯甲酸（IBX）介导的羟基化反应，与剩余的游离酚羟基相邻。检查其对RAW264.7细胞中脂多糖刺激的一氧化氮产生的抑制作用，结果表明丁酸羟基酪醇显示出最高的抑制作用（IC50 7.0μM）。
• Natural products and derivatives thereof for protection against neurodegenerative diseases
  申请人：——

  公开号：US20030236202A1

  公开（公告）日：2003-12-25

  The invention relates to the use of phenolic compounds and derivatives thereof for protection against neurodegenerative diseases, to compositions comprising these compounds, and to some novel phenolic compounds.

  该发明涉及利用酚类化合物及其衍生物来保护免受神经退行性疾病的影响，涉及包含这些化合物的组合物，以及一些新型酚类化合物。
• Identification of hydroxytyrosyl oleate, a derivative of hydroxytyrosol with anti-inflammatory properties, in olive oil by-products
  作者：Pierluigi Plastina、Cinzia Benincasa、Enzo Perri、Alessia Fazio、Giuseppina Augimeri、Mieke Poland、Renger Witkamp、Jocelijn Meijerink

  DOI：10.1016/j.foodchem.2018.12.007

  日期：2019.5

  cyclooxygenase-2 and interleukin-1β. Moreover, HtyOle was identified for the first time in olive oil by-products by means of high performance liquid chromatography coupled with mass spectrometry. By contrast, HtyOle was not found in intact olives. Our results suggest that HtyOle is formed during oil processing and represents a significant form in which hydroxytyrosol occurs.

  评价了具有短，中和长酰基链的羟基酪氨酸酯减少脂多糖刺激的RAW264.7巨噬细胞减少一氧化氮（NO）产生的能力。在测试的化合物中，发现C18酯，即硬脂酸羟基酪氨酯（HtySte）和油酸羟基酪氨酯（HtyOle），以浓度依赖的方式降低NO的产生，而其他化合物（包括母体羟基酪醇）在测试浓度下无效。范围（0.5-5μM）。对HtyOle潜在的免疫调节特性的进一步研究表明，前列腺素E 2具有明显的浓度依赖性。生产。在转录水平上，HtyOle抑制诱导型NO合酶，环氧合酶2和白介素1β的表达。此外，通过高效液相色谱-质谱联用，首次在橄榄油副产品中鉴定出HtyOle。相比之下，完整橄榄中未发现HtyOle。我们的结果表明，HtyOle是在石油加工过程中形成的，代表了其中存在羟基酪醇的重要形式。