10,12-octadecadienoic acid | 22880-03-1

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物 - 无环羧酸
• 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: 10,12-octadecadienoic acid
• 英文别名: 10,12 octadecadienoate；Octadeca-10,12-dienoic acid
• CAS: 22880-03-1
• 化学式: C₁₈H₃₂O₂
• 分子量: 280.451
• InChiKey: GKJZMAHZJGSBKD-UHFFFAOYSA-N

物化性质

• 熔点：
  55.7-57.5 °C
• 沸点：
  377.7±11.0 °C(Predicted)
• 密度：
  0.86857 g/cm3(Temp: 70 °C)
• 溶解度：
  可溶于氯仿、DMSO（微溶）、甲醇（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  20
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  蓖麻油酸 在 氢氧化钾 、 三氟化硼 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 9.75h， 生成 10,12-octadecadienoic acid
  参考文献：
  名称：

  Production of conjugated linoleic acids through KOH-catalyzed dehydration of ricinoleic acid

  摘要：

  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.

  DOI：

  10.1016/s0009-3084(02)00052-x

文献信息

• 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.