(R)-5-hydroxydecanoic acid | 197856-91-0

• 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: (R)-5-hydroxydecanoic acid
• 英文别名: (5R)-5-hydroxydecanoic acid
• CAS: 197856-91-0
• 化学式: C₁₀H₂₀O₃
• 分子量: 188.267
• InChiKey: LMHJFKYQYDSOQO-SECBINFHSA-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：

  (R)-5-hydroxydecanoic acid 在 硫酸 作用下， 反应 2.0h， 生成 (R)-6-庚基四氢吡喃-2-酮
  参考文献：
  名称：

  用新的羰基还原酶对4-和5-氧代癸酸/酯的酮基进行不对称生物还原

  摘要：

  来自粘质沙雷氏菌的新型羰基还原酶，Sm CR，已成功克隆并在大肠杆菌中过表达。Sm CR可以催化含有远端羰基的长链酮酸/酯（例如4-氧代和5-氧代十二酸）的不对称还原，产生具有高对映体纯度（高达99％ee）的手性γ-和δ-癸内酯。。这是关于使用游离酶从γ-，δ-酮酸开始酶促合成（R）-γ-和（R）-δ-十内酯的第一个报道。

  DOI：

  10.1016/j.catcom.2017.08.023
• 作为产物：
  描述：

  (R)-δ-decalactone 在 四乙基氢氧化铵 作用下， 生成 (R)-5-hydroxydecanoic acid
  参考文献：
  名称：

  Enantiomeric separation of carboxylic acids having chiral centers remote from the carboxyl group by labelling with a chiral fluorescent derivatization reagent

  摘要：

  Enantiomeric separations of 2-, 3-, 4-, 5- and 6-methyl fatty acids and 3-, 4- and 5-hydroxy fatty acids derivatized with (S)-(+)-2-(anthracene-2,3-dicarboximido)-1-propyl trifluoromethanesulfonate are described. Although there are 4-8 bond distances between the chiral centers of these diastereomeric derivatives, they are separated on HPLC and detected at fmol levels. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01616-x

文献信息

• Efficient Stereoselective Synthesis of Structurally Diverse γ‐ and δ‐Lactones Using an Engineered Carbonyl Reductase
  作者：Meng Chen、Xiao‐Yan Zhang、Chen‐Guang Xing、Chao Zhang、Yu‐Cong Zheng、Jiang Pan、Jian‐He Xu、Yun‐Peng Bai

  DOI：10.1002/cctc.201900382

  日期：2019.6.6

  efficiently synthesized stereoselectively using an engineered carbonyl reductase from Serratia marcescens (SmCRV4). SmCRV4 exhibited improved activity (up to 500‐fold) and thermostability toward 14 γ‐/δ‐keto acids and esters, compared with the wild‐type enzyme, with 110‐fold enhancement in catalytic efficiency (kcat/Km) toward methyl 4‐oxodecanoate. The preparative synthesis of alkyl and aromatic γ‐ and δ‐lactones

  结构结构多样的γ-和δ-内酯是利用粘质沙雷氏菌（Sm CR V4）中的一种工程化羰基还原酶有效地立体选择性合成的。与野生型酶相比，Sm CR V4表现出更高的活性（最高达500倍）和对14种γ-/δ-酮酸和酯的热稳定性，催化效率提高了110倍（k cat / K m）对4-氧代十二烷甲酸甲酯。证明了烷基和芳香族γ-和δ-内酯的制备合成，其ee率为95％-> 99％，收率为78％-90％。最高时空产量为1175 g L -1  d -1，达到了（R）-γ-癸内酯
• Stereoselective synthesis of chiral δ-lactones <i>via</i> an engineered carbonyl reductase
  作者：Tao Wang、Xiao-Yan Zhang、Yu-Cong Zheng、Yun-Peng Bai

  DOI：10.1039/d1cc04542c

  日期：——

  A carbonyl reductase variant, SmCRM5, from Serratia marcescens was obtained through structure-guided directed evolution. The variant showed improved specific activity (U mg−1) towards most of the 16 tested substrates and gave high stereoselectivities of up to 99% in the asymmetric synthesis of 13 γ-/δ-lactones. In particular, SmCRM5 showed a 13.8-fold higher specific activity towards the model substrate

  来自粘质沙雷氏菌的羰基还原酶变体Sm CR M5是通过结构引导的定向进化获得的。该变体对 16 种测试底物中的大多数表现出改善的比活性 (U mg -1 )，并在 13 种 γ-/δ-内酯的不对称合成中提供高达 99% 的高立体选择性。特别是，SmCR M5对模型底物（即5-氧代癸酸）的比活性高出 13.8 倍，并在 99% ee 中产生 ( R )-δ-癸内酯，时空产率 (STY) 为 301 g L -1 d -1. 六种δ-内酯的高收率和高对映体纯度的制备表明这些高附加值化学品的生物催化合成是可行的，为贵金属催化提供了一种具有成本效益的绿色替代品。
• (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。
• Continuous-flow enzymatic synthesis of chiral lactones in a three-dimensional microfluidic reactor
  作者：Xuelei Deng、Meng Fan、Miao Wu、Xiaoyan Zhang、Ya Cheng、Jianye Xia、Yingping Zhuang、Weiping Zhu、Xuhong Qian、Yunpeng Bai

  DOI：10.1016/j.cclet.2023.108684

  日期：2024.3

  enzymes was enhanced, allowing the adjustment of residence time in a wide window. SmCRV4, a carbonyl reductase with excellent catalytic activity and enantioselectivity toward γ/δ-keto acids, was employed for the asymmetric synthesis of various chiral lactones. 30 mmol/L (R)-γ-decalactone (3g) can be obtained in 26 s with a space-time yield (STY) up to 16,877 g L−1 d−1, which is 14.4 times higher than the

  一种用于酶法合成光学纯 γ-内酯的新连续流工艺，该工艺在食品和化妆品行业中用作香精和香料，经过三轮研发三维微流控反应器。使用超快飞秒激光在单个硼硅酸盐玻璃（90mm×75mm×12mm）内精确雕刻微通道（长175mm，深0.9mm，体积1.72mL）微机械加工。流场分析和反应模拟表明，底物和酶的混合得到增强，可以在较宽的窗口内调整停留时间。 SmCRV4，一种羰基还原酶，具有优异的催化活性和对映选择性γ/δ-酮酸用于各种手性内酯的不对称合成。 30mmol/L (R)-γ-十内酯 (3g) 26 秒内即可获得，时空产率 (STY) 高达 16,877g L−1 d −1，比之前报道的间歇反应最高STY高出14.4倍。该连续流程应用于 6 种手性内酯的合成。此外，3g在6个级联微反应器中连续6h进行放大合成，证明了3D连续合成的可行性和稳定性。光学纯化合物酶法合成的流程。
• Enantioselective Synthesis of <font>δ</font>-Lactones with Lipase-Catalyzed Resolution and Mitsunobu Reaction
  作者：Yasutaka Shimotori、Masakazu Aoyama、Tetsuo Miyakoshi

  DOI：10.1080/00397911.2010.529230

  日期：2012.3.1

  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.