tyrosol butyrate | 386263-87-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: tyrosol butyrate
• 英文别名: tyrosyl butyrate；2-(4-Hydroxyphenyl)ethyl butanoate
• CAS: 386263-87-2
• 化学式: C₁₂H₁₆O₃
• 分子量: 208.257
• InChiKey: HKGWRAOJKDOIII-UHFFFAOYSA-N

物化性质

• 沸点：
  329.3±17.0 °C(Predicted)
• 密度：
  1.094±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tyrosol butyrate 在 N-碘代丁二酰亚胺 、 Cl^(1-)*C₄₈H₆₈ClN₆NiO⁽¹⁺⁾ 、 四丁基碘化铵 、 potassium carbonate 、 对甲苯磺酸 、 锌 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 27.42h， 生成 (R)-2-(5-(2-(butyryloxy)ethyl)-3-methyl-2,3-dihydrobenzofuran-3-yl)acetic acid
  参考文献：
  名称：

  通过镍催化的Heck-偶联/羧化级联固定对映体选择性CO2

  摘要：

  已经开发出一种新颖的基于镍的不对称程序，其中将CO 2固定作为截短的Heck偶联的第二步。为此，已经制备了新的手性配体，并显示出达到99％的对映体过量。整个过程从易于制备的起始原料有效地提供了重要的一类生物活性产品手性2,3-二氢苯并呋喃-3-基乙酸。实验和计算的共同努力揭示了催化循环的关键步骤，并暗示了Ni（I）物种意外参与偶联事件。

  DOI：

  10.1002/chem.202101082
• 作为产物：
  描述：

  对羟基苯乙醇 、 丁酸 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 24.0h， 生成 tyrosol butyrate
  参考文献：
  名称：

  通过镍催化的Heck-偶联/羧化级联固定对映体选择性CO2

  摘要：

  已经开发出一种新颖的基于镍的不对称程序，其中将CO 2固定作为截短的Heck偶联的第二步。为此，已经制备了新的手性配体，并显示出达到99％的对映体过量。整个过程从易于制备的起始原料有效地提供了重要的一类生物活性产品手性2,3-二氢苯并呋喃-3-基乙酸。实验和计算的共同努力揭示了催化循环的关键步骤，并暗示了Ni（I）物种意外参与偶联事件。

  DOI：

  10.1002/chem.202101082

文献信息

• 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）。
• 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。
• Tyrosinase and Layer-by-Layer supported tyrosinases in the synthesis of lipophilic catechols with antiinfluenza activity
  作者：Tiziana Bozzini、Giorgia Botta、Michela Delfino、Silvano Onofri、Raffaele Saladino、Donatella Amatore、Rossella Sgarbanti、Lucia Nencioni、Anna Teresa Palamara

  DOI：10.1016/j.bmc.2013.10.026

  日期：2013.12

  Catechol derivatives with lipophilic properties have been selectively synthesized by tyrosinase in high yield avoiding long and tedious protection/deprotection steps usually required in traditional procedures. The synthesis was effective also with immobilized tyrosinase able to perform for more runs. The novel catechols were evaluated against influenza A virus, that continue to represent a severe threat worldwide. A significant antiviral activity was observed in derivatives characterized by antioxidant activity and long carbon alkyl side-chains, suggesting the possibility of a new inhibition mechanism based on both redox and lipophilic properties. (C) 2013 Elsevier Ltd. 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.
• Carbon nanotubes supported tyrosinase in the synthesis of lipophilic hydroxytyrosol and dihydrocaffeoyl catechols with antiviral activity against DNA and RNA viruses
  作者：Giorgia Botta、Bruno Mattia Bizzarri、Adriana Garozzo、Rossella Timpanaro、Benedetta Bisignano、Donatella Amatore、Anna Teresa Palamara、Lucia Nencioni、Raffaele Saladino

  DOI：10.1016/j.bmc.2015.07.061

  日期：2015.9

  Hydroxytyrosol and dihydrocaffeoyl catechols with lipophilic properties have been synthesized in high yield using tyrosinase immobilized on multi-walled carbon nanotubes by the Layer-by-Layer technique. All synthesized catechols were evaluated against a large panel of DNA and RNA viruses, including Poliovirus type 1, Echovirus type 9, Herpes simplex virus type 1 (HSV-1), Herpes simplex virus type 2 (HSV-2), Coxsackievirus type B3 (Cox B3), Adenovirus type 2 and type 5 and Cytomegalovirus (CMV). A significant antiviral activity was observed in the inhibition of HSV-1, HSV-2, Cox B3 and CMV. The mechanism of action of the most active dihydrocaffeoyl derivative was investigated against a model of HSV-1 infection. (C) 2015 Elsevier Ltd. All rights reserved.