(3S,4E)-3-(2-hydroxyethyl)-4-hydroxymethylhex-4-enoic acid 2-(4-hydroxyphenyl)ethyl ester | 951378-02-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (3S,4E)-3-(2-hydroxyethyl)-4-hydroxymethylhex-4-enoic acid 2-(4-hydroxyphenyl)ethyl ester
• 英文别名: 2-(4-hydroxyphenyl)ethyl (E,3S)-3-(2-hydroxyethyl)-4-(hydroxymethyl)hex-4-enoate
• CAS: 951378-02-2
• 化学式: C₁₇H₂₄O₅
• 分子量: 308.375
• InChiKey: LCJKQRREZYVZIP-VAKDEWRISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3S,4E)-3-(2-hydroxyethyl)-4-hydroxymethylhex-4-enoic acid 2-(4-hydroxyphenyl)ethyl ester 在 manganese(IV) oxide 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以52%的产率得到(3S,4E)-4-formyl-3-(2-hydroxyethyl)hex-4-enoic 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
• 作为产物：
  描述：

  对羟基苯乙醇 在 盐酸 、 sodium tetrahydroborate 、 sodium periodate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 水 、 乙腈 为溶剂， 反应 2.0h， 生成 (3S,4E)-3-(2-hydroxyethyl)-4-hydroxymethylhex-4-enoic 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
• Syntheses of (−)-Oleocanthal, a Natural NSAID Found in Extra Virgin Olive Oil, the (−)-Deacetoxy-Oleuropein Aglycone, and Related Analogues
  作者：Amos B. Smith、Jeffrey B. Sperry、Qiang Han

  DOI：10.1021/jo071146k

  日期：2007.8.31

  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.