[(3aS,4E,5S,6aR)-4-ethylidene-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-5-yl]acetic acid | 869476-95-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(3aS,4E,5S,6aR)-4-ethylidene-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-5-yl]acetic acid
• 英文别名: 2-[(3aS,4E,5S,6aR)-4-ethylidene-2,2-dimethyl-3a,5,6,6a-tetrahydrocyclopenta[d][1,3]dioxol-5-yl]acetic acid
• CAS: 869476-95-9
• 化学式: C₁₂H₁₈O₄
• 分子量: 226.273
• InChiKey: DVYATKNKJHDGFD-CALKAPRBSA-N

物化性质

• 沸点：
  353.1±32.0 °C(Predicted)
• 密度：
  1.173±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(3aS,4E,5S,6aR)-4-ethylidene-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-5-yl]acetic acid 在 盐酸 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 sodium periodate 、 氢氟酸 、 四丁基氟化铵 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 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
• 作为产物：
  描述：

  (-)-(3Ar,6ar)-四氢-2,2-二甲基-4H-环戊并-1,3-二氧代-4-酮 在 六甲基磷酰三胺 、 lithium hydroxide 、 cerium(III) chloride 、 Dimethylzinc 、 双(三甲基硅烷基)氨基钾 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 水 、 甲苯 为溶剂， 反应 1.0h， 生成 [(3aS,4E,5S,6aR)-4-ethylidene-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-5-yl]acetic acid
  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。
• Synthesis and Assignment of Absolute Configuration of (−)-Oleocanthal:  A Potent, Naturally Occurring Non-steroidal Anti-inflammatory and Anti-oxidant Agent Derived from Extra Virgin Olive Oils
  作者：Amos B. Smith、Qiang Han、Paul A. S. Breslin、Gary K. Beauchamp

  DOI：10.1021/ol052106a

  日期：2005.10.1

  see text] Effective total syntheses and the assignment of absolute configurations of both the (+)- and (-)-enantiomers of oleocanthal 1 (a.k.a. deacetoxy ligstroside aglycon), the latter derived from extra virgin olive oils and known to be responsible for the back of the throat irritant properties of olive oils, have been achieved. The absolute and relative stereochemistry of the naturally occurring

  [结构：见正文]有效的全合成和油酸双酚1（又称脱乙酰氧基葡糖苷糖苷配基）的（+）-和（-）-对映体的绝对构型分配，后者是从特级初榨橄榄油衍生而来的，已经实现了负责橄榄油的喉咙刺激特性的背部。天然对映异构体（-）-1的绝对和相对立体化学被证明是3S，4E。两种合成均以d-（-）-核糖开始，分12步进行，总产率为7％。两种对映异构体均被证明是非甾体类抗炎药和抗氧化剂。
• Oleocanthal for treating pain
  申请人：The Trustees of The University of Pennsylvania

  公开号：EP2583676A1

  公开（公告）日：2013-04-24

  The invention provides methods of synthesizing the purified enantiomers of oleocanthal. The invention further provides oleocanthals in various formulations for use in a method of treating pain.

  本发明提供了合成纯化的油黄质对映体的方法。本发明进一步提供了用于治疗疼痛方法的各种配方中的油黄质。
• WO2007/81808
  申请人：——

  公开号：——

  公开（公告）日：——
• Compounds and derivatives for the treatment of medical conditions by modulating hormone-sensitive lipase activity
  申请人：Sauniere Jean-Frederic

  公开号：US20070299129A1

  公开（公告）日：2007-12-27

  The present invention discloses compounds that are inhibitors of hormone-sensitive lipase. The present invention also discloses the use of the compounds and derivatives to inhibit hormone-sensitive lipase, various pharmaceutical compositions including the compounds, and methods of treatment using these compounds and compositions.