17-Hydroxyoleic acid | 4546-57-0

• 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: 17-Hydroxyoleic acid
• 英文别名: 17-OH oleic acid；(Z)-17-hydroxyoctadec-9-enoic acid
• CAS: 4546-57-0
• 化学式: C₁₈H₃₄O₃
• 分子量: 298.466
• InChiKey: UMIZOHMCQYCZRX-IHWYPQMZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  21
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

ADMET

代谢

17-羟基油酸是油酸的已知人体代谢物。

17-Hydroxyoleic acid is a known human metabolite of oleic acid.

来源:NORMAN Suspect List Exchange

反应信息

• 作为反应物：
  描述：

  17-Hydroxyoleic acid 在 二苯基膦叠氮化物 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 [(Z)-7-(9H-Fluoren-9-ylmethoxycarbonylamino)-16-hydroxy-heptadec-8-enyl]-carbamic acid tert-butyl ester
  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：

  methyl 17-hydroxyoleate 在 lithium hydroxide 作用下， 以 甲醇 为溶剂， 以98%的产率得到17-Hydroxyoleic acid
  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

文献信息

• Sustained release of active molecules from polymers topically applied to skin or hair
  申请人：Giacomoni Paolo

  公开号：US20060088489A1

  公开（公告）日：2006-04-27

  The invention relates to a polymer for topical delivery of biologically active ingredients, the polymer comprising at least one moiety: U-B-A in which U represents a physiologically acceptable unit of an oligomer or polymer, A represents a biologically active component, and B represents one or more bond(s) linking A to U, which bond is capable of being disrupted by a biological, physical or chemical process occurring in or on skin.

  该发明涉及一种用于局部传递生物活性成分的聚合物，该聚合物包括至少一种基团：U-B-A，其中U代表寡聚物或聚合物的生理可接受的单元，A代表生物活性成分，B代表将A与U连接的一个或多个键，该键能够被在皮肤内或外发生的生物、物理或化学过程破坏。
• MODIFIED SOPHOROLIPIDS FOR THE INHIBITION OF PLANT PATHOGENS
  申请人：Polytechnic Institute of New York University

  公开号：US20130085067A1

  公开（公告）日：2013-04-04

  A method for controlling pests by modifying derivatives of sophorolipids (SL) and applying the modified sophorolipid derivatives (MSL) to the plant pathogen or to an environment in which the pathogens may occur or are located in an amount such that the pathogens are substantially controlled.

  一种通过修饰Sophorolipids（SL）衍生物并将修饰后的Sophorolipid衍生物（MSL）应用于植物病原体或病原体可能出现或位于其中的环境中，以控制害虫的方法，其应用量足以实现对病原体的实质性控制。
• [EN] SOPHOROLIPID ANALOG COMPOSITIONS<br/>[FR] COMPOSITIONS D'ANALOGUES DE SOPHOROLIPIDES
  申请人：POLITECHNIC INST UNIV NEW YORK

  公开号：WO2011127101A1

  公开（公告）日：2011-10-13

  A composition of matter comprising sophorolipids as antimicrobial agents, antifungal agents, biopesticides, for uses as drugs to treat HIV, septic shock, cancer, asthma, dermatological conditions, as spermicidal agents, as anti-inflammatory drugs, as ingredients in cosmetics and building blocks for monomers and polymers and self-assembled templates for further chemical elaboration.

  一种物质组成，包含了作为抗菌剂、抗真菌剂、生物农药的Sophorolipids，可用于治疗HIV、败血症休克、癌症、哮喘、皮肤病等药物，作为杀精剂，作为抗炎药物，作为化妆品成分和单体和聚合物的构建模块以及自组装模板，以进一步进行化学改进。
• Engineering a Highly Regioselective Fungal Peroxygenase for the Synthesis of Hydroxy Fatty Acids
  作者：Patricia Gomez de Santos、Alejandro González‐Benjumea、Angela Fernandez‐Garcia、Carmen Aranda、Yinqi Wu、Andrada But、Patricia Molina‐Espeja、Diana M. Maté、David Gonzalez‐Perez、Wuyuan Zhang、Jan Kiebist、Katrin Scheibner、Martin Hofrichter、Katarzyna Świderek、Vicent Moliner、Julia Sanz‐Aparicio、Frank Hollmann、Ana Gutiérrez、Miguel Alcalde

  DOI：10.1002/anie.202217372

  日期：2023.2.20

  The biocatalytic hydroxylation of fatty acids is an appealing reaction, but the generation of over-oxidation by-products and the lack of selectivity hampers its transfer to industry. Now a highly selective and efficient peroxygenase has been engineered for the production of hydroxy fatty acids through a synthetic procedure that can be rapidly adapted to the preparative scale.

  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。
• Regioselective silyl exchange of per-silylated oligosaccharides
  申请人：THE REGENTS OF THE UNIVERSITY OF CALIFORNIA

  公开号：US10100074B2

  公开（公告）日：2018-10-16

  The present invention provides novel, regioselectively-acylated oligosaccharide compounds and methods for preparing them. In another aspect, the. invention provides a method for preparing a selectively-acylated oligosaccharide. The method includes forming a reaction mixture containing a protected oligosaccharide and an acylating agent. The protected oligosaccharide includes at least three hydroxyl moieties and each hydroxyl moiety is protected with a silyl protecting group. The reaction mixture is formed under conditions sufficient to selectively replace at least one silyl protecting group with a —C(0)-C1_6 alkyl group, and the selectively-acylated oligosaccharide comprises at least one —C(0)-C1_6 alkyl group and at least one silyl protecting group.

  本发明提供了新型的、区域选择性酰化的寡糖化合物及其制备方法。另一方面，本发明提供了一种制备选择性酰化寡糖的方法。该方法包括形成含有受保护寡糖和酰化剂的反应混合物。受保护的寡糖包括至少三个羟基，每个羟基都有一个硅基保护基团。反应混合物是在足以选择性地用-C(0)-C1_6 烷基取代至少一个硅烷基保护基的条件下形成的，选择性酰化的寡糖包括至少一个-C(0)-C1_6 烷基和至少一个硅烷基保护基。