三蓖麻精 | 2540-54-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 中文名称: 三蓖麻精
• 英文名称: castor oil
• 英文别名: ricinolein；triricinolein；2,3-bis[[(Z,12R)-12-hydroxyoctadec-9-enoyl]oxy]propyl (Z,12R)-12-hydroxyoctadec-9-enoate
• CAS: 2540-54-7
• 化学式: C₅₇H₁₀₄O₉
• 分子量: 933.447
• InChiKey: ZEMPKEQAKRGZGQ-VBJOUPRGSA-N

物化性质

• 沸点：
  879.2±65.0 °C(Predicted)
• 密度：
  0.977±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于丙酮（少许）、氯仿（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  17.8
• 重原子数：
  66
• 可旋转键数：
  53
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  140
• 氢给体数：
  3
• 氢受体数：
  9

上下游信息

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	(2R)-2,3-di-O-ricinoleoyl-sn-glycerol	——	C39H72O7	652.996
  ——	(2S)-2,3-di-O-ricinoleoyl-sn-glycerol	——	C39H72O7	652.996
  甘油三乙酰基蓖麻醇酸酯	castor oil acetate	101-34-8	C63H110O12	1059.56
  ——	2-monoricinolein	——	C21H40O5	372.546
  ——	2,3-Bis(9-hydroxynonanoyloxy)propyl 9-hydroxynonanoate	939772-34-6	C30H56O9	560.769
  蓖麻油酸甲酯	methyl ricinoleate	141-24-2	C19H36O3	312.493

反应信息

• 作为反应物：
  描述：

  三蓖麻精 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 蓖麻油酸
  参考文献：
  名称：

  Newly synthesized bolaamphiphiles from castor oil and their aggregated morphologies for potential use in drug delivery

  摘要：

  The present study focused on synthesizing bolaamphiphiles from the readily available and inexpensive castor oil, a vegetable oil, which contains about 90% of ricinoleic acid. Two classes of symmetric and asymmetric bolaamphiphiles with acetylcholine head groups were synthesized and characterized by spectroscopic analysis. These novel bolaamphiphilic compounds self-assemble in aqueous media to form stable cationic spherical nano-sized vesicles that are potential drug delivery systems. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.09.031
• 作为产物：
  描述：

  ricinoleoyl-CoA 、 Sn-1,2-diricinolein 生成 三蓖麻精 、 coenzyme A
  参考文献：
  名称：

  Identification and functional expression of a type 2 acyl-CoA:diacylglycerol acyltransferase (DGAT2) in developing castor bean seeds which has high homology to the major triglyceride biosynthetic enzyme of fungi and animals

  摘要：

  Seed oil from castor bean (Ricinus communis) contains high amounts of hydroxy fatty acid rich triacyl glycerols (TAGs) that can serve as raw material for production of bio-based products such as nylon, cosmetics, lubricants, foams, and surfactants. Diacylglycerol acyltransferase (DGAT) catalyses the terminal reaction in the acyl-CoA dependent Kennedy pathway of triglyceride biosynthesis. There is still some debate whether there are three or four enzymes in yeast that have DGAT activity and catalyse the synthesis of TAG but of these the DGAT2 homologue Dga1 contributes in a major way to TAG biosynthesis. Here we report on the cloning of a cDNA for DGAT2 from castor bean and prove its biological activity following expression in yeast and enzymatic assays using diricinolein as the acceptor and ricinoleoyl-CoA as the donor. Previous reports of DGAT in castor have focussed on DGAT1 which has little amino acid sequence homology to DGAT2. Expressional studies demonstrate that DGAT2 is 18-fold more highly expressed in seeds than in leaves and shows temporal specific expression during seed development. In contrast, DGAT1 shows little difference in expression in seeds versus leaves. We conclude that in castor bean DGAT2 is more likely to play a major role in seed TAG biosynthesis than DGAT1. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2006.09.020

文献信息

• METHOD FOR THE SYNTHESIS OF AN OMEGA-AMINO ACID OR ESTER STARTING FROM A MONOUNSATURATED FATTY ACID OR ESTER
  申请人：Dubois Jean-Luc

  公开号：US20110224454A1

  公开（公告）日：2011-09-15

  The invention relates to a method for the synthesis of ω-amino alkanoic acids or esters thereof starting from unsaturated natural fatty acids passing through an ω-unsaturated nitrile intermediate compound.

  该发明涉及一种从非饱和天然脂肪酸开始，通过一种ω-非饱和腈中间化合物来合成ω-氨基烷酸或其酯的方法。
• [EN] LIPID CONJUGATE PREPARED FROM SCAFFOLD MOIETY<br/>[FR] CONJUGUÉ LIPIDIQUE PRÉPARÉ À PARTIR D'UN FRAGMENT SQUELETTE
  申请人：INTEGRATED NANOTHERAPEUTICS INC

  公开号：WO2020191477A1

  公开（公告）日：2020-10-01

  The application relates to a lipid conjugate of formula M-X1-L wherein M is a molecule of interest such as a drug moiety; X1 is a linker group such as ester, ether or carbamate; and L is a lipid scaffold represented by formula (lId): -L1-[L2(H)(X2R)]n-L3-[L4(H)(X2R)]p-L5-L6 and wherein L comprises 5 to 40 carbon atoms and 0 to 2 carbon-carbon double bonds. The lipid conjugate can be formulated in a drug delivery vehicle such as a lipid nanoparticle (LNP).

  该应用涉及公式M-X1-L的脂质共轭物，其中M是感兴趣的分子，如药物基团；X1是连接基团，如酯、醚或氨基甲酸酯；L是由公式(lId)表示的脂质支架：-L1-[L2(H)(X2R)]n-L3-[L4(H)(X2R)]p-L5-L6，其中L包含5至40个碳原子和0至2个碳-碳双键。该脂质共轭物可以配制在药物传递载体中，如脂质纳米粒子（LNP）。
• METHOD FOR SYNTHESIZING AN OMEGA-AMINO ACID OR ESTER FROM A MONOUNSATURATED FATTY ACID OR ESTER
  申请人：Couturier Jean-Luc

  公开号：US20140187808A1

  公开（公告）日：2014-07-03

  A method for synthesizing ω-amino-alkanoic acids or the esters thereof from natural unsaturated fatty acids passing through an intermediate ω-unsaturated nitrile compound. The method is simple to implement and, relative to known methods, avoids the environmental constraints and economic disadvantages resulting from the reaction by-products. The method includes synthesizing an ω-amino acid (ester) of formula R3OOC—(CH2) q —CH2NH2, in which R3 is H or an n-butyl radical and q is an integral index of between 2 and 13, from a monounsaturated fatty acid (ester) of formula (R1-CH═CH—(CH2)p-COO) xR2, in which x represents 1, 2 or 3, R1 is H or a hydrocarbon radical comprising from 4 to 11 carbon atoms and, where appropriate, a hydroxyl function, R2 is H or an alkyl radical comprising from 2 to 4 carbon atoms, and may contain one or more heteroatoms, and p is an integral index of between 2 and 11, including a reaction step of ammoniation.

  一种从天然不饱和脂肪酸通过中间体ω-不饱和腈化合物合成ω-氨基-烷酸或其酯的方法。该方法实施简单，与已知方法相比，避免了由反应副产物导致的环境限制和经济劣势。该方法包括从公式为(R1-CH═CH—(CH2)p-COO)xR2的单不饱和脂肪酸(酯)合成公式为R3OOC—(CH2)q—CH2NH2的ω-氨基酸(酯)，其中R3是H或n-丁基基团，q是2到13之间的整数指数，x代表1、2或3，R1是H或含4到11个碳原子的烃基团，适当情况下还含有羟基，R2是H或含2到4个碳原子的烷基基团，可包含一个或多个杂原子，p是2到11之间的整数指数，包括氨化反应步骤。
• Synthesis from Undecylenic Acid of Macroheterocycles with Diacylhydrazine and Ester Fragments
  作者：G. R. Mingaleeva、M. P. Yakovleva、G. Yu. Ishmuratov

  DOI：10.1007/s10600-019-02840-2

  日期：2019.9

  A three-step synthesis of potentially biologically active 30- and 32-membered macroheterocycles with esters and acylhydrazines starting from methyl undecylenate was developed based on [1+1]-condensation of intermediate tetraesters, i.e., bis(10′ -methoxy-10′-oxodecyl)- or bis(11′-methoxy-11′ -oxoundecyl)hexanedioate, with hydrazine hydrate. The structures of the synthesized compounds were confirmed

  基于中间体四酯（即双（10'-甲氧基-10'）的 [1+1]-缩合，以十一烯酸甲酯为原料，三步合成具有潜在生物活性的 30 元和 32 元大杂环与酯和酰基肼-氧代癸基)-或双(11'-甲氧基-11'-氧十一烷基)己二酸酯，与水合肼。合成化合物的结构通过红外和核磁共振光谱和质谱进行了确认。
• Synthesis of Fatty Acetoacetates Under Microwave Irradiation Catalysed by Sulfamic Acid in a Solvent-Free System
  作者：Andressa C. H. Weber、Thaís C. Batista、Bruno Gonçalves、Carolina R. L. Hack、Larissa M. Porciuncula、Tamara G. M. Treptow、Caroline Da R. Montes D'Oca、Dennis Russowsky、Marcelo G. Montes D'Oca

  DOI：10.1007/s11746-016-2879-5

  日期：2016.10

  The 1,3‐dicarbonyl compounds are important building blocks to obtain products with various biological activities and technological applications. In this work, we used a simple transesterification method to develop fatty acetoacetates in a solvent‐free medium using a green catalyst, sulfamic acid (NH2SO3H), under microwave irradiation. The experimental results demonstrate good yields in a short reaction

  1,3-二羰基化合物是获得具有各种生物活性和技术应用产品的重要组成部分。在这项工作中，我们使用一种简单的酯交换方法，在无溶剂的介质中，使用绿色催化剂氨基磺酸（NH 2 SO 3 H），在微波辐射下开发了乙酰乙酸脂肪酯。实验结果表明，在短的反应时间（13分钟）内具有良好的收率，这使该方法成为从多种饱和，不饱和和多不饱和长链脂肪醇和蓖麻油酸衍生物合成脂肪族乙酰乙酸酯的有效方法。进行了催化剂再循环的实验，未观察到氨基磺酸的催化活性降低。