3,4-dihydroxyphenethyl octanoate | 205241-38-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3,4-dihydroxyphenethyl octanoate
• 英文别名: 2-(3,4-Dihydroxyphenyl)ethyl octanoate
• CAS: 205241-38-9
• 化学式: C₁₆H₂₄O₄
• 分子量: 280.364
• InChiKey: BSMMTDHVUMNCEC-UHFFFAOYSA-N

物化性质

• 沸点：
  427.2±30.0 °C(Predicted)
• 密度：
  1.100±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 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：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  辛酸乙烯酯 、 羟基酪醇 在 Candida antarctica lipase 作用下， 以 甲基叔丁基醚 为溶剂， 生成 3,4-dihydroxyphenethyl octanoate
  参考文献：
  名称：

  酪醇和羟基酪醇衍生物作为抗锥虫和抗疟药

  摘要：

  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。

  DOI：

  10.1016/j.ejmech.2016.04.047

文献信息

• The potential of hydroxytyrosol fatty acid esters to enhance oral bioavailabilities of hydroxytyrosol and fatty acids: Continuous and slow-release ability in small intestine and blood
  作者：Xinmiao Wang、Qian Wang、Jinghan Yu、Xu Guo、Peiyong Tong、Fawen Yin、Xiaoyang Liu、Dayong Zhou

  DOI：10.1016/j.foodchem.2023.136246

  日期：2023.10

  models indicated that hydroxytyrosol fatty acid esters (HTy-Es) could be hydrolyzed by pancreatic lipase to slow-release of free fatty acids (FAs) and HTy. Meanwhile, the HTy-Es, the liberated FAs and the HTy could cross the membrane and were transported into blood circulation. HTy-Es were further hydrolyzed by carboxylesterase in in vitro rat plasma hydrolysis model, which also showed slow-release of

  大鼠外翻肠囊的 HPLC-UV 分析和体外模拟消化模型表明，羟基酪醇脂肪酸酯 (HTy-Es) 可被胰脂肪酶水解，从而缓慢释放游离脂肪酸 (FAs) 和 HTy。同时，HTy-Es、游离的 FAs 和 HTy 可以穿过细胞膜进入血液循环。HTy-Es 在体外被羧酸酯酶进一步水解大鼠血浆水解模型，也显示 FAs (C1-C4) 和 HTy 的缓慢释放。特别是，随着烷基链长度的增加，水解和转运速率先升高后降低。此外，直链HTy-Es的上述速率大于其支链异构体的速率。因此，上述 FAs 和 HTy 在小肠和血液中的持续和缓慢释放清楚地表明 HTy-Es 将是提高游离脂肪酸和羟基酪醇口服生物利用度的有效方法。
• 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。
• Effect of Lipophilization of Hydroxytyrosol on Its Antioxidant Activity in Fish Oils and Fish Oil-in-Water Emulsions
  作者：I. Medina、S. Lois、D. Alcántara、R. Lucas、J. C. Morales

  DOI：10.1021/jf9023867

  日期：2009.10.28

  The effect of lipophilization of the antioxidant efficiency of hydroxytyrosol on fish oil enriched systems was studied. Hydroxytyrosol fatty acid esters with increasing size of the alkyl chain and different lipophilicity were tested in bulk fish oils and fish oil-in-water emulsions. Results showed a significant antioxidant activity of hydroxytyrosol esters in both systems especially in emulsions. The introduction of a lipophilic chain decreased the antioxidant effectiveness of hydroxytyrosol in homogeneous systems as fish oils. In emulsion systems, the presence of a short-medium lipophilic chain (acetate, butyrate or octanoate) improved The antioxidant efficiency of hydroxytyrosol favoring the physical location of the antioxidant in the interface, but longer alkyl chain (laurate) maintained or even decreased their antioxidant activity. A maximum of antioxidant efficiency seems to appear when the chain length of the hydroxytyrosol derivative is that of eight carbons which is probably associated with a preferential location of the diorthophenolic moiety in the right geometry. These results are of high importance for the optimum design of effective antioxidants for omega 3 enriched foods, which are very susceptible to suffer oxidation and, then, rancidity.
• 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.