十八酸-D1 | 62163-41-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 十八酸-D1
• 英文名称: (12)D1-Octadecanoic acid
• 英文别名: 12-deuterio-octadecanoic acid；Octadecanoic-12-D1 acid；12-deuteriooctadecanoic acid
• CAS: 62163-41-1
• 化学式: C₁₈H₃₆O₂
• 分子量: 285.475
• InChiKey: QIQXTHQIDYTFRH-WHRKIXHSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  20
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 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：

  12-羟基硬脂酸甲酯 在 硼氘化钠 、 pyridinium chlorochromate 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 十八酸-D1
  参考文献：
  名称：

  Why not be a queen? Regioselectivity in mandibular secretions of honeybee castes

  摘要：

  Both female castes of the honeybee (Apis mellifera L.) synthesize hydroxylated 2(E)-decenoic acids in their mandibular glands. Queens produce 9-hydroxy-2(E)-decenoic acid as part of their primer pheromone, while workers produce the regioisomeric 10-hydroxy acid, probably as a larval food source and an antiseptic secretion. Both workers and queens are biosynthetically competent to produce the other caste's dominant hydroxylated compound, as both isomers can be detected in queens and workers. We investigated the source of the caste-determined regioselectivity of hydroxy acid biosynthesis by investigating the production and interconversion of these compounds in isolated worker honeybee mandibular glands with specifically deuterated precursors. Gas chromatographic-mass spectroscopic identification of the labeled product indicates that octadecanoic acid is converted into 10-hydroxy-2(E)-decenoic acid with higher efficiency than either hexadecanoic or decanoic acids. 10-Hydroxydecanoic acid is readily converted into 10-hydroxy-2(E)-decenoic acid as expected in the beta-oxidation process. The saturated and unsaturated 10-hydroxy acids are oxidized to the corresponding ten carbon diacids.

  DOI：

  10.1007/bf02033805