17-cis-Eicosensaeure | 55833-23-3

• 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-cis-Eicosensaeure
• 英文别名: 17Z-octadecenoic acid；(Z)-icos-17-enoic acid
• CAS: 55833-23-3
• 化学式: C₂₀H₃₈O₂
• 分子量: 310.521
• InChiKey: ZOKDQRULUYMUFA-ARJAWSKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  22
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  17-cis-Eicosensaeure 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以68%的产率得到16-[(Z)-3-ethyloxiran-2-yl]hexadecanoic acid
  参考文献：
  名称：

  Synthetic ω-3 Epoxyfatty Acids As Antiproliferative and Pro-apoptotic Agents in Human Breast Cancer Cells

  摘要：

  ω-3-17,18-Epoxyeicosapentaenoic acid decreases cell proliferation and activates apoptosis, whereas its regioisomers stimulate growth. We evaluated synthetic ω-3 epoxides of saturated fatty acids as antiproliferative and pro-apoptotic agents in MDA-MB-231 breast cancer cells. The epoxides, but not their urea, amide, or carbamate isosteres, impaired ATP production, enhanced caspase-3 activity, and activated c-jun-N-terminal-kinase signaling, leading to cyclin D1 down-regulation and cell cycle arrest in G1-phase. Fatty acid ω-3 monoepoxides may represent a novel class of antitumor agents.

  DOI：

  10.1021/jm501083y
• 作为产物：
  描述：

  10-溴癸酸 在 吡啶 、 sodium hypophosphite 、 [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl) palladium(II) dichloride 、 sodium hexamethyldisilazane 、 溶剂黄146 、 乙酰氯 、 lithium bromide 、 sodium hydroxide 作用下， 以 四氢呋喃 、 N-甲基吡咯烷酮 、 乙醇 、 水 为溶剂， 反应 29.67h， 生成 17-cis-Eicosensaeure
  参考文献：
  名称：

  Antiproliferative and Antimigratory Actions of Synthetic Long Chain n-3 Monounsaturated Fatty Acids in Breast Cancer Cells That Overexpress Cyclooxygenase-2

  摘要：

  Cyclooxygenase-2 (COX-2) is overexpressed in many human cancers and converts the n-6 polyunsaturated fatty acid (PUFA) arachidonic acid to prostaglandin E-2 (PGE(2)), which drives tumorigenesis; in contrast, n-3 PUFA inhibit tumorigenesis. We tested the hypothesis that these antitumor actions of n-3 PUFA may involve the n-3 olefinic bond. n-3 Monounsaturated fatty acids (MUFAs) of chain length C16-C22 were synthesized and evaluated in MDA-MB-468 breast cancer cells that stably overexpressed COX-2 (MDA-COX-2 cells). Longer chain (C19-C22) n-3 MUFAs inhibited proliferation, activated apoptosis, decreased PGE2 formation, and decreased cell invasion; C16-C18 analogues were less active. Molecular modeling showed that interactions of Arg120, Tyr355, and several hydrophobic amino acid residues in the COX-2 active site with C19-C22 MUFA analogues were favored. Thus, longer-chain n-3 MUFAs may be prototypes of novel anticancer agents that decrease the formation of PGE2 in tumor cells that contain high levels of COX-2.

  DOI：

  10.1021/jm300673z

文献信息

• Synthesis of 19-cis-docosenoic, 17-cis-eicosenoic and 15-cis-octadecenoic acid
  作者：R. Klok、G. J. N. Egmond、H. J. J. Pabon

  DOI：10.1002/recl.19740930806

  日期：——

  Large-scale syntheses of 19-cis-docosenoic, 17-cis-eicosenoic and 15-cis-octadecenoic acid by chain extension of 8-undecynoic acid via Kolbe's anodic synthesis, as well as by coupling of 1-butyne with n-bromoalkanoic acids were found unsuitable. Therefore, 15-octadecynoic acid was prepared on a large scale from 13-hexadecyn-1-ol by malonic ester coupling. Esterification and reduction with lithium aluminium

  通过Kolbe的阳极合成方法，通过8-十一碳烯酸的扩链，以及通过将1-丁炔与正溴代链烷酸偶合，大规模合成19-顺-二十二碳酸，17-顺-二十碳烯酸和15-顺-十八碳烯酸被发现不合适。因此，通过丙二酸酯偶联从13-十六炔-1-醇大规模制备15-十八碳烯酸。用氢化锂铝进行酯化和还原，得到15-十八碳烯-1-醇。将后者转化为甲磺酸酯，然后合成丙二酸酯，得到17-二十碳五烯酸，然后通过相同的反应步骤顺序将其转化为19-二十二碳五烯酸。在Lindlar催化剂存在下，乙炔酸的氢化反应产生标题化合物。
• Synthesis of conjugated fatty acid
  申请人：——

  公开号：US20010049451A1

  公开（公告）日：2001-12-06

  A synthesis process is disclosed for producing a conjugated fatty acid at specified temperature in high yield, including providing an ester of a fatty acid having somewhere in its carbon chain a chain of four carbon atoms such that carbon one bears one hydrogen and one hydroxyl group, carbon two bears two hydrogen atoms, and a double bond is positioned between carbon three and carbon four and reacting with a chloride selected from the group consisting of toluenesulfonyl chloride, methanesulfonyl chloride, benzenesulfonyl chloride, alkylsulfonyl chloride, and aryl-sulfonyl chloride at a temperature in the range of 10° C.-100° C., preferably 20° C.-50° C. The synthesis process provides a conjugated fatty acid formed from the ester reacted with diazabicyclo-undecene. In one aspect, the ester is formed in a pyridine solvent. In one aspect, a mesylate is formed with mesyl chloride in acetonitrile and triethyl amine. In one aspect, the reaction with diazabicyclo-undecene is conducted in a polar, non-hydroxylic solvent of acetonitrile to form a preferred isomer at the specified temperature in high yield.

  本发明公开了一种在指定温度下高产率生产共轭脂肪酸的合成工艺，包括提供一种脂肪酸的酯，该脂肪酸的碳链上有四个碳原子，其中碳一含有一个氢原子和一个羟基，碳二含有两个氢原子、与选自甲苯磺酰氯、甲烷磺酰氯、苯磺酰氯、烷基磺酰氯和芳基磺酰氯的氯化物在 10° C.-100合成工艺可提供由酯与重氮双环十一烯反应形成的共轭脂肪酸。一方面，酯在吡啶溶剂中形成。一方面，在乙腈和三乙胺中用甲酰氯形成甲磺酸盐。一方面，与重氮双环十一烯的反应在极性、非羟基溶剂乙腈中进行，在指定温度下以高产率形成优选异构体。
• MIRALLES, JOSEPH;AKNIN, MAURICE;BANDIA, IBRAHIMA;BASSENE, EMMANUEL;DIAGNE+, OCEANOL. ACTA, 12,(1989) N, C. 433-436
  作者：MIRALLES, JOSEPH、AKNIN, MAURICE、BANDIA, IBRAHIMA、BASSENE, EMMANUEL、DIAGNE+

  DOI：——

  日期：——
• US6160141A
  申请人：——

  公开号：US6160141A

  公开（公告）日：2000-12-12
• US6342619B2
  申请人：——

  公开号：US6342619B2

  公开（公告）日：2002-01-29