(R)-15-hydroxyhexadecanoic acid | 212012-94-7

• 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)-15-hydroxyhexadecanoic acid
• 英文别名: (15R)-15-hydroxyhexadecanoic acid
• CAS: 212012-94-7
• 化学式: C₁₆H₃₂O₃
• 分子量: 272.428
• InChiKey: WQPQDBIUAFINBH-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  19
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 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)-15-hydroxyhexadecanoic acid 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 乙醚 为溶剂， 反应 24.0h， 以31%的产率得到(S)-(+)-15-hexadecanolide
  参考文献：
  名称：

  Synthesis of Both Enantiomers of 15-Hexadecanolide, a Sex Pheromone Component of the Stink Bug,Piezodorus hybneri

  摘要：

  通过对 (R)-β-hydroxybutyrate 乙酯制备的 (R)-15-hydroxyhexadecanoic acid（(R)-15-羟基十六烷酸）进行山口或 Mitsunobu 大内酯化反应，分 5 个步骤合成了臭虫（Piezodorus hybneri）性信息素成分 15-十六烷内酯的两种对映体。

  DOI：

  10.1271/bbb.62.1261
• 作为产物：
  描述：

  12-溴十二烷酸 在 10% palladium on active carbon 氢氟酸 、 氢气 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 乙醇 、 水 、 甲苯 、 乙腈 为溶剂， 反应 130.16h， 生成 (R)-15-hydroxyhexadecanoic acid
  参考文献：
  名称：

  Synthesis of Both Enantiomers of 15-Hexadecanolide, a Sex Pheromone Component of the Stink Bug,Piezodorus hybneri

  摘要：

  通过对 (R)-β-hydroxybutyrate 乙酯制备的 (R)-15-hydroxyhexadecanoic acid（(R)-15-羟基十六烷酸）进行山口或 Mitsunobu 大内酯化反应，分 5 个步骤合成了臭虫（Piezodorus hybneri）性信息素成分 15-十六烷内酯的两种对映体。

  DOI：

  10.1271/bbb.62.1261

文献信息

• Gene encoding cyclododecanone monooxygenase
  申请人：Iwaki Hiroaki

  公开号：US20050202547A1

  公开（公告）日：2005-09-15

  The invention relates to a new strain of Pseudomonas putida (designated as HI-70) and to the isolation, cloning, and sequencing of a cyclododecanone monooxygenase-encoding gene (named cdnB) from said strain. The invention also relates to a new cyclododecanone monooxygenase and to a method of use of the cyclododecanone monooxygenase-encoding gene.

  该发明涉及一种新的假单胞菌普提达菌株（命名为HI-70），以及从该菌株中分离、克隆和测序环十二酮单氧酶编码基因（命名为cdnB）。该发明还涉及一种新的环十二酮单氧酶以及使用环十二酮单氧酶编码基因的方法。
• Are branched chain fatty acids the natural substrates for P450BM3?
  作者：Max J. Cryle、Rocio D. Espinoza、Sarah J. Smith、Nicholas J. Matovic、James J. De Voss

  DOI：10.1039/b601202g

  日期：——

  Branched chain fatty acids are substrates for cytochrome P450BM3 (CYP102) from Bacillus megaterium; oxidation of C15 and C17iso and anteiso fatty acids by P450BM3 leads to the formation of hydroxylated products that possess high levels of regiochemical and stereochemical purity.

  支链脂肪酸是巨大芽孢杆菌细胞色素 P450BM3 (CYP102) 的底物； P450BM3 对 C15 和 C17 异和反异脂肪酸的氧化导致形成具有高水平区域化学和立体化学纯度的羟基化产物。
• The stereochemistry of fatty acid hydroxylation by cytochrome P450BM3
  作者：Max J. Cryle、Nick J. Matovic、James J. De Voss

  DOI：10.1016/j.tetlet.2006.10.136

  日期：2007.1

  The stereochemical preference for the cytochrome P450BM3-catalysed hydroxylation of tetradecanoic and pentadecanoic acids has been determined via comparison with authentic non-racemic standards utilising enantioselective HPLC. The sub-terminal hydroxylation of these fatty acids by P450BM3 is highly selective for the formation of the R-alcohols. This is the same enantioselectivity as is seen for hexadecanoic

  通过与对映选择性HPLC的可靠非外消旋标准品进行比较，确定了细胞色素P450 BM3催化的十四烷酸和十五烷酸羟基化的立体化学偏好。这些脂肪酸通过P450 BM3的亚末端羟基化对于R-醇的形成具有高度选择性。这与十六烷酸氧化反应的对映选择性相同，但与先前报道的P450 BM3对十五烷酸进行S-羟基化反应相反。
• ——
  作者：Walter Soares Leal、Shigefumi Kuwahara、Xiongwei Shi、Hiroya Higuchi、Claudia E. B. Marino、Mikio Ono、Jerrold Meinwald

  DOI：10.1023/a:1022307600446

  日期：——

  Male-released semiochemicals of the stink bug Piezodorus hybneri (Heteroptera: Pentatomidae) elicit attraction of male and female bugs and homosexual behavior in males. Three active components were isolated from the airborne volatiles of males by flash chromatography, with the activity monitored by GC-EAD and behavioral bioassay. The pheromone system was characterized as a mixture of beta-sesquiphellandrene, (R)-15-hexadecanolide, and methyl 8-(Z)-hexadecenoate (ratio: 10:4:1), and the activity of the semiochemicals was assessed with authentic samples. Enantiomerically pure samples of the R and S macrolactones were obtained by Yamaguchi's and Mitsunobu's macrolactonization of a key intermediate, (R)-15-hydroxyhexadecanoic acid. The nonnatural S stereoisomer was neither a beneficial nor a behavioral antagonist. Individual constituents or binary mixtures were active, but the optimal male response was elicited only by the full mixture. Behavioral observation and the fact that the onset of pheromone production is coincident with ovarian development strongly suggest that these semiochemicals are, in fact, sex pheromones.
• A GENE ENCODING CYCLODODECANONE MONOOXYGENASE
  申请人：NATIONAL RESEARCH COUNCIL OF CANADA

  公开号：EP1430118A2

  公开（公告）日：2004-06-23