methyl 17-hydroxyoleate | 6084-86-2

• 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: methyl 17-hydroxyoleate
• 英文别名: 17-hydroxy oleic acid methyl ester；Methyl 17-hydroxy oleate；methyl (Z)-17-hydroxyoctadec-9-enoate
• CAS: 6084-86-2
• 化学式: C₁₉H₃₆O₃
• 分子量: 312.493
• InChiKey: YFBTWGWAXOETRB-ARJAWSKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  22
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 17-hydroxyoleate 在 lithium hydroxide 、 二苯基膦叠氮化物 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 24.0h， 生成 16-hydroxyheptadecylisocyanate
  参考文献：
  名称：

  由槐糖脂衍生的17-羟基油酸合成多官能脂肪胺

  摘要：

  AbstractA series of mono‐ and diamines and one triamine have been prepared using methyl 17‐hydroxy oleate as the common starting material. The 17‐hydroxy oleate is an abundant bioderived material obtained from acid alcoholysis of sophorolipids, which in turn are produced by fermentation of agricultural by‐products. Incorporation of the amino unit(s) can be selectively performed at either end of the chain or at its middle. The chief synthetic reactions used are allylic bromination, Curtius rearrangement, and the Mitsunobu reaction. These fatty amines also possess functionality such as hydroxy groups, carboxylic acids, and C−C double bonds. The amines are isolated in protected form using a variety of protecting groups, the identities of which can be selected on the basis of the intended use of the amine. These novel compounds will be of interest in the preparation of highly functionalized polymers and surfactants, among other areas.

  DOI：

  10.1007/s11746-006-1248-1
• 作为产物：
  描述：

  油酸甲酯 在 双氧水 、 unspecific peroxygenase Fett from Pichia pastoris strain X-33 mutant A₇₇L 作用下， 以 aq. phosphate buffer 、 丙酮 为溶剂， 以100 %的产率得到methyl 17-hydroxyoleate
  参考文献：
  名称：

  设计一种用于合成羟基脂肪酸的高区域选择性真菌过氧化酶

  摘要：

  脂肪酸的生物催化羟基化是一个吸引人的反应，但过度氧化副产物的产生和选择性的缺乏阻碍了它向工业的转移。现在，一种高选择性和高效的过氧化酶已被设计用于通过可快速适应制备规模的合成程序来生产羟基脂肪酸。

  DOI：

  10.1002/anie.202217372

文献信息

• Epoxidizable Fatty Amide–Phenol Conjugates
  作者：Jonathan A. Zerkowski、Michael J. Haas

  DOI：10.1007/s11746-011-1785-0

  日期：2011.8

  also prepared: one acrylamide, one styrene derivative, and two types of AB2 diamino acids, all of which contain oleic units that are sites for epoxidation and crosslinking. Fatty acid aryl ethers were prepared using hydroxy fatty acids. These molecules are intended to serve as augmented analogues of epoxidized vegetable oil. Their amide groups should lead to intermolecular aggregation through hydrogen

  本文报道了一系列新型化合物的合成，其中羧酸已通过酰胺甲基单元与苯酚连接。例如，已将一种，两种或三种脂肪酸选择性地连接到苯酚上，产率超过75％。所使用的脂肪酸是油酸，其随后被环氧化。可以将其他官能团例如氨基酸结合到这些化合物中。还制备了适合聚合的单体实例：一种丙烯酰胺，一种苯乙烯衍生物和两种类型的AB 2二氨基酸，全部都含有油酸单元，这些单元是环氧化和交联的位点。使用羟基脂肪酸制备脂肪酸芳基醚。这些分子旨在用作环氧化植物油的增强类似物。它们的酰胺基应通过氢键导致分子间聚集，共价包括其他官能团的选择可能会允许调节由它们构成的薄膜，涂层或固体的宏观材料性能。
• Structured Estolides: Control of Length and Sequence
  作者：Jonathan A. Zerkowski、Alberto Nuñez、Daniel K. Y. Solaiman

  DOI：10.1007/s11746-007-1185-7

  日期：2008.3

  AbstractUsing ester‐forming reactions such as carbodiimide coupling and a modified Yamaguchi symmetrical anhydride method, a variety of estolides based on 17‐hydroxy oleic and 17‐hydroxy stearic acid have been prepared. These hydroxy fatty acids are produced in good yields from hydrolysis of sophorolipids, which are in turn derived from fermentation of fats and oils. Since the estolides are formed one unit, or ester bond, at a time, their length and sequence can be precisely controlled. The key to this control is the use of protecting groups at either the carboxylic or hydroxy end of the starting hydroxy fatty acids. Two mono‐protected dimers, for example, when combined in a fragment‐condensation approach, give a tetramer with no “contamination” from estolides of other lengths. This methodology opens the way to functionalized estolides, and several variants were prepared: hybrid estolides, containing non‐fatty acid moieties such as amino acids; polymerizable estolides, containing a norbornene unit; and non‐linear estolides that extend from a branched core such as glycerol or pentaerythritol. With the benzoyl chloride‐mediated symmetrical anhydride method, yields for individual coupling steps ranged from 75 to 93%.
• US9382566B1
  申请人：——

  公开号：US9382566B1

  公开（公告）日：2016-07-05