hydroxytyrosol propionate

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: hydroxytyrosol propionate
• 英文别名: 2-(3,4-Dihydroxyphenyl)ethyl propanoate
• 化学式: C₁₁H₁₄O₄
• 分子量: 210.23
• InChiKey: HNCXLIDKZIHUPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  对羟基苯乙醇 在 Agaricus bisporus 、 Candida antarctica 、 氧气 作用下， 以 aq. phosphate buffer 、 二氯甲烷 为溶剂， 反应 48.0h， 生成 hydroxytyrosol propionate
  参考文献：
  名称：

  Tyrosinase and Layer-by-Layer supported tyrosinases in the synthesis of lipophilic catechols with antiinfluenza activity

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2013.10.026

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。
• 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。
• Hydroxytyrosol lipophilic analogues: Enzymatic synthesis, radical scavenging activity and DNA oxidative damage protection
  作者：Salvatore Grasso、Laura Siracusa、Carmela Spatafora、Marcella Renis、Corrado Tringali

  DOI：10.1016/j.bioorg.2006.09.003

  日期：2007.4

  The olive oil phenol hydroxytyrosol (3), as well its metabolite homovanillic alcohol (4), were subjected to chemoselective lipase-catalysed acylations, affording with good yield 10 derivatives (5-14) bearing C-2, C-3, C-4, C-10 and C-18 acyl chains at C-1. Hydroxytyrosol (3) and its lipophilic derivatives showed very good DPPH radical scavenging activity. Compounds 3, 4 and their lipophilic analogues 5-14 were subjected to the atypical Comet test on whole blood cells: 3 and its analogues 5 and 6, with little hydrophobic character (logP <= 1.20), showed a good protective effect against H2O2 induced oxidative DNA damage. The homovanillic alcohol 4 and its analogues 10-14 resulted scarcely effective both as radical scavengers and antioxidant agents. (c) 2006 Elsevier Inc. All rights reserved.
• Expedient Synthesis of Hydroxytyrosol and its Esters
  作者：Paolo Bovicelli、Roberto Antonioletti、Silvia Mancini、Stefano Causio、Giorgio Borioni、Sergio Ammendola、Maurizio Barontini

  DOI：10.1080/00397910701575509

  日期：2007.12

  An efficient and friendly method for obtaining hydroxytyrosol from tyrosol, a component of olive waste, is reported. Hydroxytyrosol also may be obtained in the form of enzymatically convertible precursors (e.g., hydroxytyrosyl acetate), thus increasing the stability of the active principle.
• 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.