(Z)-(R)-12-methanesulfonyloksyoctadec-9-enoic acid methyl ester | 57884-97-6

• 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: (Z)-(R)-12-methanesulfonyloksyoctadec-9-enoic acid methyl ester
• 英文别名: methyl (R,Z)-12-((methylsulfonyl)oxy)octadec-9-enoate；methyl (Z)-12-(methylsulfonyloxy)octadec-9-enoate；methyl ricinoleate methanesulphonate；methyl 12-mesyloxy-octadec-9-enoate
• CAS: 57884-97-6
• 化学式: C₂₀H₃₈O₅S
• 分子量: 390.585
• InChiKey: JEQPHUZELAFVAD-KWRJMZDGSA-N

物化性质

• 沸点：
  496.5±38.0 °C(Predicted)
• 密度：
  1.018±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.15
• 重原子数：
  26.0
• 可旋转键数：
  17.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  69.67
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (Z)-(R)-12-methanesulfonyloksyoctadec-9-enoic acid methyl ester 在 甲醇 、 sodium methylate 、 臭氧 作用下， 反应 50.5h， 生成 (3R)-3-羟基壬醛
  参考文献：
  名称：

  Synthesis of (S)-ricinoleic acid and its methyl ester with the participation of ionic liquid

  摘要：

  (R)-Ricinoleic acid methyl ester obtained from commercial castor oil was transformed in a three-step procedure into its S-enantiomer in overall 36% yield using ionic liquid (1-butyl-3-methylimidazolium acetate) in the key step process. The developed procedure provides easy access to (S)-ricinoleic acid and its methyl ester of over 95% enantiomeric excess. Optical rotations of the newly obtained compounds as well as their chromatographic and spectral characteristics are provided and discussed in the context of enantiopurity both of the substrate material and the final products. (C) 2014 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.chemphyslip.2014.06.005
• 作为产物：
  描述：

  蓖麻油酸 在 boron trifluoride methanol complex 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 46.0h， 生成 (Z)-(R)-12-methanesulfonyloksyoctadec-9-enoic acid methyl ester
  参考文献：
  名称：

  四种新型蓖麻油酸衍生的 1-O-烷基甘油的合成和生物学评价。

  摘要：

  以市售蓖麻油酸为原料，合成了一系列新型取代的 1-O-烷基甘油 (AKGs)，其烷基链 12 位含有甲氧基 (8)、偕二氟 (9)、叠氮化物 (10) 和羟基 (11) (12)。这些新合成的 AKG 的结构是通过 NMR 实验以及 HRMS 和元素分析数据确定的。分别评估了所研究的AKGs 8-11的抗菌活性，所有化合物单独以及与一些常用抗生素（庆大霉素、四环素、环丙沙星和氨苄青霉素）联合时均表现出不同程度的抗菌活性。AKG 11 被视为该系列的先导化合物，因为它的抗菌活性明显高于化合物 8-10。

  DOI：

  10.3390/md18020113

文献信息

• Enzyme Cascade Reactions for the Biosynthesis of Long Chain Aliphatic Amines from Renewable Fatty Acids
  作者：Da‐Som Lee、Ji‐Won Song、Moritz Voß、Eva Schuiten、Ravi Kumar Akula、Yong‐Uk Kwon、Uwe Bornscheuer、Jin‐Byung Park

  DOI：10.1002/adsc.201801501

  日期：2019.3.15

  Enzyme cascade reactions for the synthesis of long chain aliphatic amines such as (Z)‐12‐aminooctadec‐9‐enoic acid, 10‐ or 12‐aminooctadecanoic acid, and 10‐amino‐12‐hydroxyoctadecanoic acid from renewable fatty acids were investigated. (Z)‐12‐aminooctadec‐9‐enoic acid was produced from ricinoleic acid ((Z)‐12‐hydroxyoctadec‐9‐enoic acid) via (Z)‐12‐ketooctadec‐9‐enoic acid with a conversion of 71%

  研究了由可再生脂肪酸合成长链脂族胺如（Z）-12-氨基十八碳9-烯酸，10-或12-氨基十八碳烯酸和10-氨基-12-羟基十八碳烯酸的酶级联反应。（Z）-12-氨基十八烷基-9-烯酸是由蓖麻油酸（（Z）-12-羟基十八烷基-9-烯酸）经（Z）-12-酮十八烷基-9-烯酸生产的，转化率为71％通过分两步进行的体内生物转化，涉及黄腐微球菌的长链仲醇脱氢酶（SADH）和黄潮弧菌的胺转氨酶（ATA）的变体。由油酸制备10-氨基十八碳烯酸（（Z体内的三步生物催化反应，不仅通过SADH和ATA变体，而且还通过嗜麦芽气单胞菌的脂肪酸双键水合酶（OhyA）通过10-羟基十八碳烯酸和10-酮十八碳烯酸）嗜麦芽癖。
• Synthesis, antimicrobial and anti-biofilm activities of novel Schiff base analogues derived from methyl-12-aminooctadec-9-enoate
  作者：Y. Mohini、R.B.N. Prasad、M.S.L. Karuna、Y. Poornachandra、C. Ganesh Kumar

  DOI：10.1016/j.bmcl.2014.09.062

  日期：2014.11

  methoxy (5o), were found to exhibit excellent to good antimicrobial activities (MIC value 9–18 μM) against Staphylococcus aureus MTCC 96, Staphylococcus aureus MLS-16 MTCC 2940 and Bacillus subtilis MTCC 121. The products were also screened for anti-biofilm and MBC (Minimum Bactericidal Concentration) activities which exhibited promising activities.

  席夫碱类似物（5a - q）的新型文库是由12-氨基十八烷基-9-烯酸甲酯与不同取代的芳族醛缩合而合成的。通过光谱技术（FT-IR，1 H NMR，13 C NMR，ESI-MS和HRMS）对合成的化合物进行了全面表征。筛选具有不同取代基的席夫碱类似物对7种不同细菌菌株的体外抗菌活性。其中，具有吸电子取代基的化合物为氯（5a），具有给电子取代基的化合物为羟基（5n）和甲氧基（5o）。）对金黄色葡萄球菌MTCC 96，金黄色葡萄球菌MLS-16 MTCC 2940和枯草芽孢杆菌MTCC 121表现出优异的抗菌性能（MIC值为9-18μM）。还对产品进行了抗生物膜和MBC筛选（最低杀菌浓度）活动，表现出良好的发展前景。
• Synthesis of a saturated lipid hydroperoxy-cyclic peroxide
  作者：Edwin N. Frankel、David Weisleder、William E. Neff

  DOI：10.1039/c39810000766

  日期：——

  A simple one-step method has been developed for the synthesis of a saturated hydroperoxy-epidioxide by allowing the methanesulphonate of methyl ricinoleate to react with 90% H2O2 in diethyl ether; the stereo-chemistry of the cyclic peroxide product has been established.

  通过使蓖麻油酸甲酯的甲磺酸盐与二乙醚中的90％H 2 O 2反应，已开发出一种简单的一步法来合成饱和的氢过氧-环氧乙烷。已经建立了环状过氧化物产物的立体化学。
• Production of conjugated linoleic acids through KOH-catalyzed dehydration of ricinoleic acid
  作者：Lin Yang、Yu Huang、Han Qing Wang、Zhen-Yu Chen

  DOI：10.1016/s0009-3084(02)00052-x

  日期：2002.10

  Production of conjugated linoleic acids (CLA) using castor oil as starting material involves conversion of ricinoleic acid to methyl 12-mesyloxy-octadec-9-enoate (MMOE) followed by dehydration. This process usually uses 1,8diazabicyclo-(5.4.0)-undec-7-ene (DBU) as an expensive dehydrating reagent. The present study reports that potassium hydroxide (KOH) can serve as a dehydrating reagent in replacement of DBU. The results showed that conversion of MMOE to CLA catalyzed by KOH was an efficient reaction, with a 77% conversion efficiency at 80 degreesC. The CLA isomeric profile produced in KOH-catalyzed dehydration reaction was similar to that catalyzed by DBU. The CLA mixture produced in KOH-catalyzed dehydration of MMOE at 80 degreesC contained 72% 9c,11t-18:2 and 26% 9c,11c-18:2 while in that catalyzed by DBU, 9c,11t-18:2 and 9c,11c-18:2 accounted for 78 and 16%, respectively. It was found that the temperature of dehydration was an important factor in the determination of CLA isomer composition and yield of conversion. Elevating the temperature from 78 to 180 degreesC decreased not only the conversion efficiency but also production of total c,t-18:2 and c,c-18:2 isomers regardless of dehydration catalyzed by either DBU or KOH. It is concluded that KOH may replace DBU as a dehydrating reagent in conversion of MMOE to CLA when the reaction conditions are optimized. (C) 2002 Elsevier Science Ireland Ltd. All rights reserved.