10-Oxyoctadecanamide | 925700-62-5

• 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-Oxyoctadecanamide
• 英文别名: 10-Oxooctadecanamide；10-oxooctadecanamide
• CAS: 925700-62-5
• 化学式: C₁₈H₃₅NO₂
• 分子量: 297.481
• InChiKey: LHFXASOLCMBMJX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  21
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  60.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  10-氧代-十八烷酸 在 ammonium carbamate 、 Nowozym 435 作用下， 以 2-甲基-2-丁醇 为溶剂， 以92.1%的产率得到10-Oxyoctadecanamide
  参考文献：
  名称：

  10-羟基硬脂酸，10-酮硬脂酸及其伯脂肪酰胺的生物催化生产

  摘要：

  AbstractThe objective of this study was to develop scaleup bioprocesses for producing 10‐hydroxystearic acid (10‐HSA) and 10‐ketostearic acid (10‐KSA) as well as their primary amides for potential new uses. A reactor process was examined to obtain the mono‐oxygenated FA using Sphingobacterium thalpophilum (NRRL B‐14797) and Bacillus sphaericus (NRRL NRS‐732), which solely produce 10‐HSA and 10‐KSA, respectively, from technical‐grade oleic acid. By using an 8‐h‐old B‐14797 culture grown in a manganese‐containing WF6 medium, pH 7.3, at 28°C under 350 rpm agitation and 0–50% dissolved oxygen concentrations provided by a controlled sparger aeration, the production of 10‐HSA reached 7 g/L with a 40% yield in 4 d. In using a 12‐h‐old NRS‐732 culture grown in a pyruvate‐containing PF6 medium, pH 6.5, at 30°C under 750 rpm agitation without any sparger aeration during the conversion reaction, 10‐KSA production reached 7.9 g/L with a yield of more than 54% in 72 h. The scaleup reactor process provided crystalline 10‐HSA and 10‐KSA for producting new primary amides via a lipase‐catalyzed amidation reaction with yields of 94 and 92%, respectively. The primary amides of 10‐HSA and 10‐KSA displayed m.p of 115 and 120°C, respectively.

  DOI：

  10.1007/s11746-006-5022-1

文献信息

• Biocatalytic production of 10-hydroxystearic acid, 10-ketostearic acid, and their primary fatty amides
  作者：Tsung Min Kuo、William E. Levinson

  DOI：10.1007/s11746-006-5022-1

  日期：2006.8

  AbstractThe objective of this study was to develop scaleup bioprocesses for producing 10‐hydroxystearic acid (10‐HSA) and 10‐ketostearic acid (10‐KSA) as well as their primary amides for potential new uses. A reactor process was examined to obtain the mono‐oxygenated FA using Sphingobacterium thalpophilum (NRRL B‐14797) and Bacillus sphaericus (NRRL NRS‐732), which solely produce 10‐HSA and 10‐KSA, respectively, from technical‐grade oleic acid. By using an 8‐h‐old B‐14797 culture grown in a manganese‐containing WF6 medium, pH 7.3, at 28°C under 350 rpm agitation and 0–50% dissolved oxygen concentrations provided by a controlled sparger aeration, the production of 10‐HSA reached 7 g/L with a 40% yield in 4 d. In using a 12‐h‐old NRS‐732 culture grown in a pyruvate‐containing PF6 medium, pH 6.5, at 30°C under 750 rpm agitation without any sparger aeration during the conversion reaction, 10‐KSA production reached 7.9 g/L with a yield of more than 54% in 72 h. The scaleup reactor process provided crystalline 10‐HSA and 10‐KSA for producting new primary amides via a lipase‐catalyzed amidation reaction with yields of 94 and 92%, respectively. The primary amides of 10‐HSA and 10‐KSA displayed m.p of 115 and 120°C, respectively.