12-acetylricinoleic acid | 14936-79-9

• 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: 12-acetylricinoleic acid
• 英文别名: (12R)-12-acetoxyoleic acid；acetylated ricinoleate；12-O-acetylricinoleic acid；O-acetyl-ricinolic acid；O-Acetyl-ricinolsaeure；(Z,12R)-12-acetyloxyoctadec-9-enoic acid
• CAS: 14936-79-9
• 化学式: C₂₀H₃₆O₄
• 分子量: 340.503
• InChiKey: OZNJPDLVWMTLKB-QTJNJRLBSA-N

物化性质

• 沸点：
  433.8±28.0 °C(Predicted)
• 密度：
  0.970±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  24
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  12-acetylricinoleic acid 在 氯化亚砜 作用下， 生成 12-acetoxyoleoyl chloride
  参考文献：
  名称：

  Page; Rudy, Biochemische Zeitschrift, 1930, vol. 220, p. 304,308, 321

  摘要：

  DOI：
• 作为产物：
  描述：

  蓖麻油酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 、 锌 作用下， 以 甲醇 、 溶剂黄146 、 甲苯 为溶剂， 反应 18.0h， 生成 12-acetylricinoleic acid
  参考文献：
  名称：

  Development of the First Ultra-Potent “Capsaicinoid” Agonist at Transient Receptor Potential Vanilloid Type 1 (TRPV1) Channels and Its Therapeutic Potential

  摘要：

  Olvanil（N-9-Z-十八碳烯酰-香草酰胺）是一种瞬时受体电位香草素亚型1（TRPV1）通道的激动剂，不具备辣椒素的那种刺激性，开发用于口服镇痛。与结构复杂的树脂佛波酯类TRPV1激动剂（如resiniferatoxin）相比，香草酰胺因其结构简单、合成直接和安全性高等特点而独树一帜。我们对olvanil的脂肪酸酰基链进行了修饰，得到了超强活性的类似物。在C-12位插入一个羟基得到化合物rinvanil，其活性显著低于olvanil（EC50=6与0.7nM相比），但由于存在额外的官能团，使得结构修饰更加多样化。对rinvanil进行乙酰化和苯乙酰化后，其对人TRPV1的活性分别得到恢复和显著增强。苯乙酰基rinvanil（PhAR，IDN5890）的EC50为90皮摩尔，是迄今为止描述的最强效的香草酰胺，其活性与resiniferatoxin相当（EC50，11皮摩尔）。苯甲酰基-和苯丙酰基rinvanil的活性分别与PhAR相当和低于PhAR，而构型反转至ent-PhAR和双键的环丙烷化（而非氢化或环氧化）是可以接受的。最后，对芳香羟基进行碘化会导致功能活性发生剧烈转变，产生的化合物表现为TRPV1拮抗剂而非激动剂。由于PhAR在大鼠背根神经节神经元中的活性得以维持，特别是在大鼠膀胱中，该化合物在大鼠尿失禁体内模型中进行了研究，并证明其减少膀胱逼尿肌过度活动的效力与resiniferatoxin相当。

  DOI：

  10.1124/jpet.104.074864

文献信息

• Novel environmentally sustainable plasticizers based on ricinoleic acid for polyvinyl chloride: structure and properties
  作者：Y. Y. Jiang、F. X. Gao、L. Ren、Q. Liu、T. Song、Y. D. Shen、W. N. Du、Y. B. Wang、M. Y. Zhang

  DOI：10.1039/d3nj05313j

  日期：——

  result in the reduction of petroleum resources. Thus, the development of bio-based plasticizers with migration resistance is very critical. In this study, two novel bio-based plasticizers with different structures derived from ricinoleic acid, i.e., epoxy acetylated benzyl ricinoleate (EABR) and epoxy acetyl terephthalate ricinoleate (EATPR), with good plasticizing effect and migration resistance were

  传统石化增塑剂的迁移会对增塑产品的性能、人类健康和环境产生负面影响，并导致石油资源减少。因此，开发具有抗迁移性的生物基增塑剂非常关键。本研究合成并表征了两种不同结构的蓖麻油酸衍生的新型生物基增塑剂，即环氧乙酰化蓖麻油酸苄酯（EABR）和环氧乙酰对苯二甲酸蓖麻油酸酯（EATPR），具有良好的增塑效果和抗迁移性。使用 FTIR 和1 H NMR 光谱证实了 EABR 和 EATPR 的结构。对用 EABR 和 EATPR 增塑的 PVC 样品的机械、热和迁移性能进行了广泛研究，并使用商业增塑剂对苯二甲酸二辛酯 (DOTP) 进行比较。使用 EABR 和 EATPR 增塑的 PVC 样品表现出与 DOTP 增塑样品相似的冲击强度、断裂伸长率和玻璃化转变温度 ( T g )，表明对 PVC 具有良好的增塑效果。此外，与 DOTP 相比，EABR 和 EATPR 在迁移和挥发性测试中表现出优越的性能
• Method for producing microcapsule
  申请人：Iuchi Seiji

  公开号：US10350569B2

  公开（公告）日：2019-07-16

  An object of the present invention is to provide a technique for producing a microcapsule containing a pesticidal compound in a fatty acid ester such as methyl O-acetylricinoleate, which delays the release timing of the pesticidal compound as compared to a conventional microcapsule. Provided is a method for producing a microcapsule, which comprises: (1) keeping a mixture of a pesticidal compound, a compound represented by formula (I): wherein X represents —CH2—CH2— or —CH═CH—, R1 represents a C1-C4 alkyl group, and R2 represents a C1-C4 alkyl group, and a polyisocyanate at 20 to 60° C. for 3 hours or more; (2) adding the mixture to water containing a polyol or a polyamine to prepare liquid droplets in the water; and (3) forming a film of polyurethane or polyurea around the droplets.

  本发明的目的是提供一种生产微胶囊的技术，该微胶囊含有一种脂肪酸酯，如 O-乙酰基蓖麻油酸甲酯中的杀虫化合物，与传统的微胶囊相比，该微胶囊可延长杀虫化合物的释放时间。本发明提供了一种生产微胶囊的方法，其中包括： (1) 保存杀虫化合物、由式 (I) 代表的化合物的混合物： 其中 X 代表-CH2-CH2-或-CH═CH-，R1 代表 C1-C4 烷基，R2 代表 C1-C4 烷基，以及聚异氰酸酯在 20 至 60 摄氏度的条件下 3 小时或更长时间； (2) 将混合物加入含有多元醇或多胺的水中，在水中制备液滴；以及 (3) 在液滴周围形成一层聚氨酯或聚脲薄膜。
• Antioxidant, anti-inflammatory and anti-hyperglycaemic activities of heterocyclic homoprostanoid derivatives
  作者：S.A. Manohara Reddy、Jayesh Mudgal、Punit Bansal、S.G. Vasanthraju、K.K. Srinivasan、C. Mallikarjuna Rao、N. Gopalan Kutty

  DOI：10.1016/j.bmc.2010.11.016

  日期：2011.1

  A series of 19 heterocyclic homoprostanoids were synthesized from easily available oleic and ricinoleic acids and evaluated for their possible antioxidant, anti-inflammatory and anti-hyperlipidaemic activities. Compounds with thioxo- and oxoimidazole ring (1) and (2) have shown potent antioxidant activity with IC(50) values 0.23 +/- 0.09 and 0.41 +/- 0.01 mM comparable with standard ascorbic acid. Compound (3) with a quinoxaline ring showed maximum inhibition of BSA denaturation at 1 mM concentration and comparable with standard diclofenac. Incorporation of electron withdrawing substitutions like chloro- and nitro-groups in the quinoxaline ring has resulted in an increase anti-inflammatory activity. Test compounds (3), (3a) and (3c) showed modest inhibition of DPP-IV in vitro. However, the unsubstituted quinoxaline (3) and substituted quinoxalines (3b and 3c) reduced plasma glucose levels indicating the presence of hypoglycemic activity. (C) 2010 Elsevier Ltd. All rights reserved.
• Dhingra; Uppal; Venkataraman, Journal of the Society of Dyers and Colourists, vol. 53, p. 96
  作者：Dhingra、Uppal、Venkataraman

  DOI：——

  日期：——
• <i>N</i>-Acylvanillamides:  Development of an Expeditious Synthesis and Discovery of New Acyl Templates for Powerful Activation of the Vanilloid Receptor
  作者：Giovanni Appendino、Alberto Minassi、Aniello Schiano Morello、Luciano De Petrocellis、Vincenzo Di Marzo

  DOI：10.1021/jm020844o

  日期：2002.8.1

  A simple and general synthesis of vanillamides was developed and employed to screen acids from the fatty and isoprenoid pools for new acyl templates of biological relevance as capsaicin analogues. Potent activation of the human vanilloid receptor 1 (VR1) was observed for the vanillamides of certain polyfunctional acids from both pools, showing that the vanilloid activity of capsaicinoids can be. substantially improved by introducing polar groups and/or unsaturations on the acyl moiety. The activity of the unsaturated analogues was maintained or even increased by cyclopropAnation, while omega dimerization led to a substantial increase of activity. Because of the Wide structural diversity of the library of compounds screened, these observations could not be translated into a single framework of structure-activity relationships. Nevertheless, a series of new highly active leads was identified, validating the pharmacological potential of the unnatural combination of natural building blocks to provide new bioactive compounds.