(3S,4R)-4-formyl-3-(2-oxoethyl)hexanoic acid 2-(4-hydroxyphenyl)ethyl ester

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (3S,4R)-4-formyl-3-(2-oxoethyl)hexanoic acid 2-(4-hydroxyphenyl)ethyl ester
• 英文别名: 2-(4-hydroxyphenyl)ethyl (3S,4R)-4-formyl-3-(2-oxoethyl)hexanoate
• 化学式: C₁₇H₂₂O₅
• 分子量: 306.359
• InChiKey: ABEMYYFQYNXZNF-GJZGRUSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  22
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  对羟基苯乙醇 在 Crabtree' catalyst 盐酸 、 sodium periodate 、 氢气 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙腈 为溶剂， 23.0 ℃ 、1.72 MPa 条件下， 反应 5.25h， 生成 (3S,4R)-4-formyl-3-(2-oxoethyl)hexanoic acid 2-(4-hydroxyphenyl)ethyl ester
  参考文献：
  名称：

  Syntheses of (−)-Oleocanthal, a Natural NSAID Found in Extra Virgin Olive Oil, the (−)-Deacetoxy-Oleuropein Aglycone, and Related Analogues

  摘要：

  Phenolic compounds extracted from extra virgin olive oil have attracted considerable recent attention. One of the components, (-)-oleocanthal (1), an inhibitor of the COX-1 and COX-2 enzymes, possesses similar potency as the NSAID ibuprofen. In this, a full account, we disclose the first- and now second-generation syntheses of both enantiomers of the oleocanthals, as well as the first synthesis of the closely related (-)-deacetoxy-oleuropein aglycone and a series of related analogues for structure activity studies. To demonstrate the utility of the second-generation synthesis, multigram quantities of (-)-oleocanthal were prepared in 10 steps (14% overall yield) from commercially available D-lyxose.

  DOI：

  10.1021/jo071146k

文献信息

• USE OF THE IRRITATING PRINCIPAL OLEOCANTHAL IN OLIVE OIL, AS WELL AS STRUCTURALLY AND FUNCTIONALLY SIMILAR COMPOUNDS
  申请人：Peyrot Des Gachons Catherine

  公开号：US20110020424A1

  公开（公告）日：2011-01-27

  The invention provides oleocanthal analogs and methods of using oleocanthals in various formulations including, food additives; pharmaceuticals; cosmetics; animal repellants; and discovery tools for mammalian irritation receptor genes, gene products, alleles, splice variants, alternate transcripts and the like.

  这项发明提供了油酸甘露醇类似物以及在各种配方中使用油酸甘露醇的方法，包括食品添加剂；药品；化妆品；动物驱避剂；以及用于哺乳动物刺激受体基因、基因产物、等位基因、剪接变体、替代转录本等的发现工具。
• US8586632B2
  申请人：——

  公开号：US8586632B2

  公开（公告）日：2013-11-19
• [EN] USE OF THE IRRITATING PRINCIPAL OLEOCANTHAL IN OLIVE OIL, AS WELL AS STRUCTURALLY AND FUNCTIONALLY SIMILAR COMPOUNDS<br/>[FR] EMPLOI DE L'OLÉOCANTHAL, PRINCIPE IRRITANT DE L'HUILE D'OLIVE, AINSI QUE DE COMPOSÉS DE STRUCTURE ET DE FONCTION SIMILAIRES
  申请人：UNIV PENNSYLVANIA

  公开号：WO2007133908A2

  公开（公告）日：2007-11-22

  [EN] The invention provides oleocanthal analogs and methods of using oleocanthals in various formulations including, food additives; pharmaceuticals; cosmetics; animal repellants; and discovery tools for mammalian irritation receptor genes, gene products, alleles, splice variants, alternate transcripts and the like.
  [FR] La présente invention concerne des analogues d'oléocanthal ainsi que des méthodes d'emploi d'oléocanthals dans diverses formules, y compris les additifs alimentaires; les produits pharmaceutiques; les produits cosmétiques; les produits de répulsion d'animaux; et des outils de découverte de gènes, de produits de gènes, d'allèles, de variants d'épissage, de variants de transcription, entre autres, concernant les récepteurs d'irritation chez les mammifères.