4-hydroxyphenethyl octanoate | 1021296-42-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-hydroxyphenethyl octanoate
• 英文别名: 2-(4-Hydroxyphenyl)ethyl octanoate
• CAS: 1021296-42-3
• 化学式: C₁₆H₂₄O₃
• 分子量: 264.365
• InChiKey: NTTPXOUIYZQWQL-UHFFFAOYSA-N

物化性质

• 沸点：
  386.6±17.0 °C(Predicted)
• 密度：
  1.031±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  19
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  辛酸 、 对羟基苯乙醇 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以93%的产率得到4-hydroxyphenethyl octanoate
  参考文献：
  名称：

  酪醇脂肪酸酯类化合物及其制备方法和应用

  摘要：

  本发明公开了酪醇脂肪酸酯类化合物及其制备方法和应用，属于生物医药技术领域，该酪醇脂肪酸酯类化合物是对酪醇的化学结构进行衍生化，在其结构中引入脂肪酸，其结构与酪醇相比有较大差异，且具有较好的抑菌和抗氧化作用。本发明还提供了酪醇脂肪酸酯的制备方法，即以酪醇、三苯基磷和脂肪酸为原料，氮气保护下加入四氢呋喃，0℃下滴加偶氮二甲酸二异丙酯，反应后经柱层析即得。有益效果为：本发明酪醇脂肪酸酯类化合物药物动力学性能好、生物活性高；该制备方法反应过程步骤短、选择性好，一步反应即可得到目标化合物，收率高，环境友好；该酪醇脂肪酸酯具有抑菌和抗氧化作用。

  公开号：

  CN109111362A

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。
• Lignin Nanoparticles Support Lipase‐Tyrosinase Enzymatic Cascade in the Synthesis of Lipophilic Hydroxytyrosol Ester Derivatives
  作者：Elisabetta Tomaino、Eliana Capecchi、Davide Piccinino、Raffaele Saladino

  DOI：10.1002/cctc.202200380

  日期：2022.9.20

  Enzyme catalysis: Layer-by-layer functionalized lignin nanoparticles acts as a sustainable platform in the lipase M and tyrosinase cascade synthesis of bioactive lipophilic hydroxytyrosol esters from tyrosol and long side-chain carboxylic acids under organic solvent conditions.

  酶催化：在有机溶剂条件下，由酪醇和长侧链羧酸合成生物活性亲脂性羟基酪醇酯的脂肪酶 M 和酪氨酸酶级联合成中，逐层功能化木质素纳米颗粒充当了可持续的平台。
• Synthesis of Bioactive Hydroxytyrosol Esters via Multienzyme Cascade on Electroactive Melanin Lignin Nanoparticles: A One‐Pot Approach without Extra Reducing Agents
  作者：Davide Piccinino、Valentina Ubertini、Eliana Capecchi、Elisabetta Tomaino、Valeria Gigli、Raffaele Saladino

  DOI：10.1002/cctc.202300533

  日期：2023.7.21

  A one‐pot strategy for the synthesis of bioactive hydroxytyrosol esters from tyrosol and lipophilic carboxylic acids has been developedviamultienzyme cascade immobilized on electroactive melanin lignin nanoparticles. The novel catalyst involved the co‐immobilization of lipase and tyrosinase on the polyphenolic support and was operative in the presence of sustainable 2‐methyltetrahydrofuran as organic reaction solvent. The system did not require the use of extra reducing agents for the selective synthesis of catechols. Optoelectronic and electrochemical studies suggested the role played by melanin lignin nanoparticles in the regeneration of the active site of tyrosinase from unproductivemet‐form to reversibledeoxy/oxy‐form. This effect improved the overall activity of tyrosinase in the multienzyme cascade favouring the reduction of undesired quinones to corresponding catechols.

  摘要 开发了一种以酪醇和亲脂性羧酸为原料合成生物活性羟基酪醇酯的单锅策略，该策略是将多酶级联固定在具有电活性的黑色素木质素纳米颗粒上。这种新型催化剂将脂肪酶和酪氨酸酶共同固定在多酚载体上，并可在可持续的 2-甲基四氢呋喃作为有机反应溶剂的情况下工作。该系统在选择性合成儿茶酚时无需使用额外的还原剂。光电和电化学研究表明，黑色素木质素纳米颗粒在将酪氨酸酶的活性位点从非生产性的金属形式再生为可逆的乙氧基/氧形式方面发挥了作用。这种作用提高了酪氨酸酶在多酶级联中的整体活性，有利于将不需要的醌还原为相应的儿茶酚。
• Synthesis of Benzoxazines by Heterogeneous Multicomponent Biochemo Multienzymes Cascade Reaction
  作者：Elisabetta Tomaino、Eliana Capecchi、Valentina Ubertini、Davide Piccinino、Bruno M. Bizzarri、Raffaele Saladino

  DOI：10.1021/acs.joc.3c02314

  日期：2024.2.16

  This work describes the possibility to combine multicomponent chemistry and multienzymes cascade transformations in a unique reactive framework to yield highly functionalized 1,4-benzoxazines under favorable heterogeneous conditions. The synthetic scheme involved the generation in situ of electrophilic reactive quinone intermediates of tyrosol esters catalyzed by lipase M and tyrosinase followed by

  这项工作描述了在独特的反应框架中结合多组分化学和多酶级联转化的可能性，以在有利的异质条件下产生高度功能化的 1,4-苯并恶嗪。该合成方案包括在脂肪酶 M 和酪氨酸酶催化下原位生成酪醇酯的亲电活性醌中间体，然后对选定的 α-氨基酸甲酯进行亲核 1,6-Michael 加成，以及连续的分子内内酯化和芳构化过程。多酶级联在电活性木质素纳米颗粒上的固定化提高了整个系统的可持续性和可回收性。
• 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.