(S)-5-hydroxydecanoic acid | 134625-01-7

• 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: (S)-5-hydroxydecanoic acid
• 英文别名: (5S)-5-hydroxydecanoic acid
• CAS: 134625-01-7
• 化学式: C₁₀H₂₀O₃
• 分子量: 188.267
• InChiKey: LMHJFKYQYDSOQO-VIFPVBQESA-N

物化性质

• 沸点：
  320.8±25.0 °C(Predicted)
• 密度：
  1.011±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-5-hydroxydecanoic acid 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 24.0h， 生成 (S)-(-)-delta-癸内酯
  参考文献：
  名称：

  Enantioselective Synthesis of δ-Lactones with Lipase-Catalyzed Resolution and Mitsunobu Reaction

  摘要：

  Both enantiomers of a series of delta-lactones (e.g., delta-decalactone, delta-dodelactone, and delta-hexadecalactone) were synthesized stereoselectively by Novozym 435-catalyzed resolution. Furthermore, only (S)-enantiomers of delta-lactones were synthesized with a combination of Novozym 435-catalyzed resolution and Mitsunobu reaction.

  DOI：

  10.1080/00397911.2010.529230
• 作为产物：
  描述：

  [(5S)-1-(methylamino)-1-oxodecan-5-yl] acetate 在 sodium hydroxide 、 硫酸 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 (S)-5-hydroxydecanoic acid
  参考文献：
  名称：

  Enantioselective Synthesis of δ-Lactones with Lipase-Catalyzed Resolution and Mitsunobu Reaction

  摘要：

  Both enantiomers of a series of delta-lactones (e.g., delta-decalactone, delta-dodelactone, and delta-hexadecalactone) were synthesized stereoselectively by Novozym 435-catalyzed resolution. Furthermore, only (S)-enantiomers of delta-lactones were synthesized with a combination of Novozym 435-catalyzed resolution and Mitsunobu reaction.

  DOI：

  10.1080/00397911.2010.529230

文献信息

• (S)-5-hydroxydecanoic acid and its therapeutic composition
  申请人：MOCHIDA PHARMACEUTICAL CO., LTD.

  公开号：EP0410446A1

  公开（公告）日：1991-01-30

  The present invention relates to a compound selected from the group consisting of (S)-5-­hydroxydecanoic acid, a salt, a solvate and a solvate of said salt thereof and relates to methods for producing the compound, comprising of inversion of the configuration and also relates to a pharmaceutical composition for treatment of cardiovascular diseases such as arrhythmia and ischemic heart diseases, or diabates.

  本发明涉及一种选择自(S)-5-羟基癸酸、盐、溶剂和该盐的溶剂的组合物的化合物，并涉及用于生产该化合物的方法，包括构象的倒转，并涉及一种用于治疗心血管疾病如心律失常和缺血性心脏病或糖尿病的药物组合物。
• Regio‐ and Enantio‐selective Chemo‐enzymatic C−H‐Lactonization of Decanoic Acid to ( <i>S</i> )‐δ‐Decalactone
  作者：Jack Manning、Michele Tavanti、Joanne L. Porter、Nico Kress、Sam P. De Visser、Nicholas J. Turner、Sabine L. Flitsch

  DOI：10.1002/anie.201901242

  日期：2019.4.16

  AbstractThe conversion of saturated fatty acids to high value chiral hydroxy‐acids and lactones poses a number of synthetic challenges: the activation of unreactive C−H bonds and the need for regio‐ and stereoselectivity. Here the first example of a wild‐type cytochrome P450 monooxygenase (CYP116B46 from Tepidiphilus thermophilus) capable of enantio‐ and regioselective C5 hydroxylation of decanoic acid 1 to (S)‐5‐hydroxydecanoic acid 2 is reported. Subsequent lactonization yields (S)‐δ‐decalactone 3, a high value fragrance compound, with greater than 90 % ee. Docking studies provide a rationale for the high regio‐ and enantioselectivity of the reaction.
• Optical Resolution of Fragrant Lactones
  作者：Hiroyuki Nohira、Keiko Mizuguchi、Toru Murata、Yuko Yazaki、Miho Kanazawa、Yoshio Aoki、Misako Nohira

  DOI：10.3987/com-99-s149

  日期：——

  Optical resolution of six chiral fragrant lactones (delta-jasmine lactone, massoia lactone, tuberolactone, pentynyllactone, delta-decalactone, and gamma-nonalactone) was investigated by means of either the diastereomeric salt formation method or the diastereomeric amide formation method. Using these procedures, we obtained each enantiomer from five of the six lactones, except for massoia lactone. All five lactones were obtained in a good yield and with high optical purity. Sensoric characteristics on both enantiomers and racemic modification of four lactones are given.
• BLANCO, B.;GUIBE-JAMPEL, E.;ROUSSEAU, G., TETRAHEDRON LETT., 29,(1988) N 16, 1915-1918
  作者：BLANCO, B.、GUIBE-JAMPEL, E.、ROUSSEAU, G.

  DOI：——

  日期：——
• MOSANDL, ARMIN;GESSNER, MARTIN, Z. LEBENSM.-UNTERSUCH. UND FORSCH., 187,(1988) N 1, 40-44
  作者：MOSANDL, ARMIN、GESSNER, MARTIN

  DOI：——

  日期：——