(Z)-9-hydroxyoctadec-12-enoic acid | 105182-18-1

• 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: (Z)-9-hydroxyoctadec-12-enoic acid
• 英文别名: 9-hydroxy-cis-12-octadecenoic acid；9-OH 18:1(Δ12)；isoricinoleic acid；9-hydroxyoctadec-cis-12-enoic acid
• CAS: 105182-18-1
• 化学式: C₁₈H₃₄O₃
• 分子量: 298.466
• InChiKey: BNZYDQIAPCVNAT-VURMDHGXSA-N

物化性质

• 沸点：
  445.5±28.0 °C(Predicted)
• 密度：
  0.957±0.06 g/cm3(Predicted)

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

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  (Z,Z)-9,12-十八烷二烯酸二聚物	linoleic acid	60-33-3	C18H32O2	280.451
  ——	9-oxooctadec-cis-12-enoic acid	112543-32-5	C18H32O3	296.45

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	isoricinoleic acid methyl ester	10026-39-8	C19H36O3	312.493
  9-羟基十八烷酸	9-hydroxystearic acid	3384-24-5	C18H36O3	300.482
  ——	9-oxooctadec-cis-12-enoic acid	112543-32-5	C18H32O3	296.45

反应信息

• 作为反应物：
  描述：

  (Z)-9-hydroxyoctadec-12-enoic acid 在 silver(I) chromate 、 间氯过氧苯甲酸 作用下， 生成 9,12-二氧代十八烷酸
  参考文献：
  名称：

  由γ-hydroxyolefinic酸与银的反应的1,4-二氧代衍生物的新的合成铬酸盐-碘配合物，随后米氯过苯甲酸氧化

  摘要：

  用复杂的铬酸银和碘的反应γ -hydroxylefinic酸（isoricinoleic），得到13-碘-9,12- epoxyoctadecanoic酸，其在用治疗米氯过苯甲酸具有-9,12-二氧代十八烷定量产率的酸。

  DOI：

  10.1039/c39830001057
• 作为产物：
  描述：

  1-溴-2辛炔 在 Lindlar's catalyst 氢氧化钾 、 sodium tetrahydroborate 、 草酰氯 、 氢气 、 sodium ethanolate 作用下， 以 乙醇 为溶剂， 生成 (Z)-9-hydroxyoctadec-12-enoic acid
  参考文献：
  名称：

  974.（±）-顺式-9-羟基十八烷基-12-烯酸的合成

  摘要：

  DOI：

  10.1039/jr9610004945

文献信息

• NOVEL COOLANTS WITH IMPROVED STORAGE STABILITY
  申请人：BASF SE

  公开号：EP4015596A1

  公开（公告）日：2022-06-22

  The present application describes coolants with increased activity against corrosion of aluminium and aluminium alloys and improved storage stability, the corresponding coolant concentrates, and the use of such coolants.

  本申请介绍了具有更高抗铝和铝合金腐蚀活性和更佳储存稳定性的冷却剂、相应的冷却剂浓缩物以及此类冷却剂的使用。
• Coolant for cooling systems in electric vehicles having fuel cells and/or batteries containing azole derivatives and additional corrosion protectants
  申请人：BASF SE

  公开号：US11248155B2

  公开（公告）日：2022-02-15

  The present invention relates to coolants for cooling systems in electric vehicles having fuel cells and/or batteries, preferably for motor vehicles, particularly preferably for passenger cars and commercial vehicles (known as light and heavy duty vehicles), based on alkylene glycols or derivatives thereof, which comprise additional corrosion inhibitors for improved corrosion protection in addition to specific azole derivatives.

  本发明涉及用于具有燃料电池和/或电池的电动汽车冷却系统的冷却剂，优选用于机动车辆，尤其优选用于乘用车和商用车辆（称为轻型和重型车辆），冷却剂以亚乙基二醇或其衍生物为基础，除特定的唑衍生物外，还包括用于改善腐蚀保护的附加腐蚀抑制剂。
• ω-Alkynyl Lipid Surrogates for Polyunsaturated Fatty Acids: Free Radical and Enzymatic Oxidations
  作者：William N. Beavers、Remigiusz Serwa、Yuki Shimozu、Keri A. Tallman、Melissa Vaught、Esha D. Dalvie、Lawrence J. Marnett、Ned A. Porter

  DOI：10.1021/ja506038v

  日期：2014.8.13

  Lipid and lipid metabolite profiling are important parameters in understanding the pathogenesis of many diseases. Alkynylated polyunsaturated fatty acids are potentially useful probes for tracking the fate of fatty acid metabolites. The nonenzymatic and enzymatic oxidations of omega-alkynyl linoleic acid and omega-alkynyl arachidonic acid were compared to that of linoleic and arachidonic acid. There was no detectable difference in the primary products of nonenzymatic oxidation, which comprised cis,trans-hydroxy fatty acids. Similar hydroxy fatty acid products were formed when omega-alkynyl linoleic acid and omega-alkynyl arachidonic acid were reacted with lipoxygenase enzymes that introduce oxygen at different positions in the carbon chains. The rates of oxidation of omega-alkynylated fatty acids were reduced compared to those of the natural fatty acids. Cyclooxygenase-1 and -2 did not oxidize alkynyl linoleic but efficiently oxidized alkynyl arachidonic acid. The products were identified as alkynyl 11-hydroxy-eicosatetraenoic acid, alkynyl 11-hydroxy-8,9-epoxy-eicosatrienoic acid, and alkynyl prostaglandins. This deviation from the metabolic profile of arachidonic acid may limit the utility of alkynyl arachidonic acid in the tracking of cyclooxygenase-based lipid oxidation. The formation of alkynyl 11-hydroxy-8,9-epoxy-eicosatrienoic acid compared to alkynyl prostaglandins suggests that the omega-alkyne group causes a conformational change in the fatty acid bound to the enzyme, which reduces the efficiency of cyclization of dioxalanyl intermediates to endoperoxide intermediates. Overall, omega-alkynyl linoleic acid and omega-alkynyl arachidonic acid appear to be metabolically competent surrogates for tracking the fate of polyunsaturated fatty acids when looking at models involving autoxidation and oxidation by lipoxygenases.
• Husain, Syed Rafat; Ahmad, Fasih; Ahmad, Mashood, Acta Chimica Hungarica, 1985, vol. 120, # 1, p. 29 - 38
  作者：Husain, Syed Rafat、Ahmad, Fasih、Ahmad, Mashood

  DOI：——

  日期：——
• Pseudohalogenation of methyl 9-hydroxy-<i>cis</i>-12-and 12-hydroxy-<i>cis</i>-9-octadecenoate
  作者：Fehmida Naqvi、Abdul Rauf、M. M. Siddiqui、M. S. Ahmad、S. M. Osman

  DOI：10.1007/s11746-997-0206-x

  日期：1997.6

  AbstractPseudohalogenation of methyl 9‐hydroxy‐cis‐12‐octadecenoate (I) and methyl 12‐hydroxy‐cis‐9‐octadecenoate (II) has been carried out with N,N‐dibromobenzenesulfonamide (NNDBS). Compounds I and II, on reaction with NNDBS, formed four and three products, respectively. The interesting feature of these reactions was the formation of 1,4‐epoxy compounds. The structures of individual compounds were established with the help of elemental and spectral analysis.