hydroxytyrosyl palmitate

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: hydroxytyrosyl palmitate
• 英文别名: Hydroxytyrosol Palmitate；2-(3,4-dihydroxyphenyl)ethyl hexadecanoate
• 化学式: C₂₄H₄₀O₄
• 分子量: 392.579
• InChiKey: BLTGRACDRXBTNT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  28
• 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：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  hydroxytyrosyl palmitate 、 氯甲酸乙酯 在 三乙胺 作用下， 以 丙酮 为溶剂， 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：

  3,4-二羟基苯乙酸 在 硫酸 、 erbium(III) triflate 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 11.0h， 生成 hydroxytyrosyl palmitate
  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。
• 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。
• 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。
• METHOD OF PREPARING HYDROXYTYROSOL ESTERS, ESTERS THUS OBTAINED AND USE OF SAME
  申请人：CONSEJO SUPERIOR DE INVESTIGACIONES CIENTIFICAS

  公开号：EP1541544A1

  公开（公告）日：2005-06-15

  The invention relates to a method of preparing a wide range of hydroxytyrosol esters. According to the invention, the compounds are synthesised by reacting synthetic hydroxytyrosol or natural hydroxytyrosol compounds, oleuropein or oleuropein aglycones (which are found in olive oil, vegetable water, olive marc or olive leaves) with an acylating agent which is a compound containing at least one acylic group R, wherein R is H, an alkyl radical with between 1 and 31 linear, branched or cyclic carbon atoms, an alkenyl radical with up to 31 linear, branched or cyclic carbon atoms or an aryl group. The invention also relates to the esters prepared with the inventive method, which can be used as an additive in food and cosmetic products as well as in pharmaceutical preparations.

  该发明涉及一种制备多种羟基酪醇酯的方法。根据该发明，这些化合物是通过将合成羟基酪醇或天然羟基酪醇化合物、橄榄叶苷或橄榄叶苷缺失物（这些物质存在于橄榄油、植物水、橄榄渣或橄榄叶中）与至少含有一个酰基R的酰化剂反应合成的，其中R为H、具有1至31个线性、支链或环状碳原子的烷基基团、具有最多31个线性、支链或环状碳原子的烯基基团或芳基团。该发明还涉及用该创新方法制备的酯，可用作食品和化妆品中的添加剂，以及药物制剂中使用。