hydroxytyrosyl linoleate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: hydroxytyrosyl linoleate
• 英文别名: hydroxytyrosol linoleate；2-(3',4'-dihydroxyphenyl)ethyl linoleate；Cis-Hydroxytyrosol Linoleate；2-(3,4-dihydroxyphenyl)ethyl (9Z,12Z)-octadeca-9,12-dienoate
• 化学式: C₂₆H₄₀O₄
• 分子量: 416.601
• InChiKey: REWQVNRZRPEQBD-HZJYTTRNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  30
• 可旋转键数：
  18
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 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：

  3,4-二羟基苯乙酸 在 硫酸 、 erbium(III) triflate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 23.0h， 生成 hydroxytyrosyl linoleate
  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

• 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。
• 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。
• 抗氧化剂共价结合的亚油酸及其制备方法和用途
  申请人：中国农业大学

  公开号：CN111196757A

  公开（公告）日：2020-05-26

  本发明公开了抗氧化剂共价结合的亚油酸及其制备方法和用途。其中，制备抗氧化剂共价结合的亚油酸的方法包括：将亚油酸、羧基活化剂、抗氧化剂、醇羟基活化剂、溶剂混合并进行反应，得到所述抗氧化剂共价结合的亚油酸。该方法将亚油酸与抗氧化剂通过酯键共价结合，打破了现有亚油酸抗氧化保护方法中抗氧化剂与亚油酸相对位置的限制和包封效率的限制，大大提高抗氧化剂对亚油酸的保护效果。同时，亚油酸与抗氧化剂之间形成的酯键在人体内会被脂肪酶水解，从而释放出亚油酸，不会影响亚油酸的营养功能。
• Lipophilic Hydroxytyrosyl Esters. Antioxidant Activity in Lipid Matrices and Biological Systems
  作者：Mariana Trujillo、Raquel Mateos、Laura Collantes de Teran、José L. Espartero、Rosa Cert、Maria Jover、Felipe Alcudia、Juan Bautista、Arturo Cert、Juan Parrado

  DOI：10.1021/jf060520z

  日期：2006.5.1

  Antioxidant activities of lipophilic hydroxytyrosyl acetate, palmitate, oleate, and linoleate were compared with those of hydroxytyrosol, alpha-tocopherol, and butylhydroxytoluene (BHT) in both glyceridic matrix and biological systems. Aliquots of a glyceridic matrix spiked with various concentrations of antioxidant were subjected to accelerated oxidation in a Rancimat apparatus operated at 90 degrees C. The relationships between induction time (IT) and antioxidant concentration (mmol/kg) presented by hydroxytyrosol and hydroxytyrosyl acetate, palmitate, oleate, and linoleate were similar. Hydroxytyrosol and its esters showed greater antioxidant activity than R-tocopherol or BHT. We also evaluated the capacity of hydroxytyrosyl esters to protect proteins and lipids against oxidation caused by peroxyl radicals, using a brain homogenate as an ex vivo model. All tested compounds showed a protective effect in these systems, which was greater in preventing the generation of carbonyl groups in protein than of malondialdehyde in lipid. Inclusion of a lipophilic chain in the hydroxytyrosol molecule enhanced its antioxidant capacities in this biological model.
• Lipophilic Hydroxytyrosol Esters: Fatty Acid Conjugates for Potential Topical Administration
  作者：Antonio Procopio、Christian Celia、Monica Nardi、Manuela Oliverio、Donatella Paolino、Giovanni Sindona

  DOI：10.1021/np200405s

  日期：2011.11.28

  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.