alpha-桐酸 | 506-23-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: alpha-桐酸
• 英文名称: eleostearic acid
• 英文别名: α-eleostearic acid；9-cis,11-trans,13-trans-octadecatrienoic acid；alpha-eleostearic acid；αESA；α-Elaeostearinsaeure；(9Z,11E,13E)-octadeca-9,11,13-trienoic acid
• CAS: 506-23-0
• 化学式: C₁₈H₃₀O₂
• 分子量: 278.435
• InChiKey: CUXYLFPMQMFGPL-WPOADVJFSA-N

物化性质

• 熔点：
  49°C
• 沸点：
  361.24°C (rough estimate)
• 密度：
  0.9028
• 溶解度：
  可溶于水基（轻微）、氯仿（轻微）、甲醇（非常轻微）

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  20
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

制备方法与用途

α-异硬脂酸（顺式异硬脂酸），一种共轭亚麻酸，是一种凋亡诱导剂。α-eledostaric 酸也是一种铁死亡诱导剂。α-榄香酸具有抗氧化和抗肿瘤活性。

反应信息

• 作为反应物：
  描述：

  alpha-桐酸 在 platinum(IV) oxide 、 溶剂黄146 作用下， 生成 硬脂酸
  参考文献：
  名称：

  The Preparation of Pure Stearic Acid

  摘要：

  DOI：

  10.1021/ja01858a505
• 作为产物：
  描述：

  9Z,11E,13E-十八碳三烯酸甲酯 生成 alpha-桐酸
  参考文献：
  名称：

  立体选择性制备1-氯-（E，E）-1,3-二烯。在合成硬脂酸甲酯中的应用。

  摘要：

  链烯基丙烯与（E）-二氯乙烯的镍（或钯）催化反应在温和条件下得到1-氯-（E，E）-1,3-二烯。描述了α-硬脂酸甲酯的合成，据报道这是棉铃虫的摄食威慑剂，其异构体之一是芥子酸甲酯。

  DOI：

  10.1016/s0040-4039(01)81743-3

文献信息

• Improved LC−MS Method for the Determination of Fatty Acids in Red Blood Cells by LC−Orbitrap MS
  作者：Xingnan Li、Adrian A. Franke

  DOI：10.1021/ac103093w

  日期：2011.4.15

  We report a new method for fast and sensitive analyses of biologically relevant fatty acids (FAs) in red blood cells (RBC) by liquid chromatography mass spectrometry (LC−MS). A new chemical derivatization approach was developed forming picolylamides from FAs in a quantitative reaction. Fourteen derivatized FA standards, including saturated and unsaturated FAs from C14 to C22, were efficiently separated within 15 min. In addition, the use of a recently introduced benchtop orbitrap mass spectrometer under positive electrospray ionization (ESI) full scan mode showed a 2−10-fold improvement in sensitivity compared with a conventional tandem MS method, with a limit of detection in the low femtomole range for saturated and unsaturated FAs. The developed method was applied to determine FA concentrations in RBC with intra- and interday coefficients of variation below 10%.

  我们报告了一种通过液相色谱质谱联用（LC−MS）快速且灵敏分析红细胞（RBC）中生物学相关的脂肪酸（FAs）的新方法。该方法开发了一种形成吡啶甲酰胺的新化学衍生化途径，通过定量反应从FAs中生成。包括从C14到C22的饱和及不饱和FAs在内的14种衍生化FA标准品，在15分钟内得以高效分离。此外，采用最近推出的台式轨道阱质谱仪在正离子电喷雾电离（ESI）全扫描模式下进行检测，相较于传统串联MS方法，灵敏度提高了2至10倍，对饱和及不饱和FAs的检测限达到了低飞摩尔水平。所开发的方法被应用于测定RBC中的FA浓度，其日内和日间变异系数均低于10%。
• GLYCERYL ASCORBIC ACID ACYLATED DERIVATIVE OR ITS SALT, PRODUCTION METHOD THEREOF, AND COSMETICS
  申请人：YOSHIOKA Masato

  公开号：US20130204017A1

  公开（公告）日：2013-08-08

  A glyceryl ascorbic acid acylated derivative or its salt, which has an ascorbic acid structure where 2- and/or 3-positions of the structure are substituted with glyceryl groups and some of the hydroxyl groups in the structure and/or in the glyceryl group are acylated, a production method of the glyceryl ascorbic acid acylated derivative and a cosmetic containing the glyceryl ascorbic acid acylated derivative or its salt are provided.

  提供一个甘油抗坏血酸酰化衍生物或其盐，其具有抗坏血酸结构，其中2-和/或3-位被甘油基团取代，并且结构中的一些羟基和/或甘油基团被酰化，提供甘油抗坏血酸酰化衍生物的生产方法，以及包含甘油抗坏血酸酰化衍生物或其盐的化妆品。
• Development of a High-Throughput Assay for Measuring Phospholipase A Activity Using Synthetic 1,2-α-Eleostearoyl-<i>sn</i>-glycero-3-phosphocholine Coated on Microtiter Plates
  作者：Meddy El Alaoui、Alexandre Noiriel、Laurent Soulère、Lucie Grand、Yves Queneau、Abdelkarim Abousalham

  DOI：10.1021/ac502096v

  日期：2014.11.4

  To date, several sensitive methods, based on radiolabeled elements or sterically hindered fluorochrome groups, are usually employed to screen phospholipase A (PLA) activities. With the aim of developing a convenient, specific, sensitive, and continuous new ultraviolet (UV) spectrophotometric assay for PLA, we have synthesized a specific glycerophosphatidylcholine (PC) esterified at the sn-1 and sn-2 positions, with α-eleostearic acid (9Z, 11E, 13E-octadecatrienoic acid) purified from Aleurites fordii seed oil. The conjugated triene present in α-eleostearic acid constitutes an intrinsic chromophore and, consequently, confers the strong UV absorption properties of this free fatty acid as well as of the glycerophospholipids harboring it. This coated PC film cannot be desorbed by the various buffers used during PLA assays. Following the action of PLA at the oil–water interface, α-eleostearic acid is freed and desorbed from the film and then solubilized with β-cyclodextrin. The UV absorbance of the α-eleostearic acid is considerably enhanced due to the transformation from an adsorbed to a water-soluble state. The PLA activity can be measured continuously by recording the variations with time of the UV absorption spectra. The rate of lipolysis was monitored by measuring the increase of absorption at 272 nm, which was found to be linear with time and proportional to the amount of added PLA. This continuous high-throughput PLA assay could be used to screen new PLA and/or PLA inhibitors present in various biological samples.

  迄今为止，基于放射性标记元素或空间位阻氟硼荧光素基团的多种敏感方法通常被用于筛选磷脂酶A（PLA）活性。为了开发一种方便、特异、敏感且可连续进行的新型紫外（UV）分光光度法PLA检测方法，我们合成了一种在sn-1和sn-2位置上酯化有从油桐（Aleurites fordii）种子油中纯化的α-桐酸（9Z,11E,13E-十八碳三烯酸）的特定甘油磷脂酰胆碱（PC）。α-桐酸中存在的共轭三烯构成了一种固有的发色团，因此赋予了这种游离脂肪酸及其包含的甘油磷脂强大的紫外吸收特性。这种涂覆的PC膜在PLA检测过程中无法被各种缓冲液解吸。在油水界面经过PLA作用后，α-桐酸被释放并从膜中解吸，然后与β-环糊精溶解。由于从吸附状态转变为水溶性状态，α-桐酸的紫外吸光度显著增强。通过记录紫外吸收光谱随时间的变化，可以连续测量PLA活性。通过测量272 nm处吸收增加的情况来监测脂解速率，发现其随时间呈线性且与添加的PLA量成正比。这种连续的高通量PLA检测方法可用于筛选存在于各种生物样本中的新型PLA和/或PLA抑制剂。
• METHOD OF STABILIZING IMINO-FUNCTIONAL SILANE
  申请人：Momentive Performance Materials Inc.

  公开号：US20180016287A1

  公开（公告）日：2018-01-18

  A method of stabilizing imino-functional silane involving adding thereto at least one Brønsted-Lowry base to inhibit, suppress or prevent the addition reactions of the imino-functional silane with itself to form a imino- and amino-functional silane and the subsequent deamination reactions to form conjugated carbon-carbon double bond-containing imino-functional silanes and stabilized imino-functional silanes containing the at least one Brønsted-Lowry base.

  一种稳定亚胺官能硅烷的方法涉及向其中添加至少一种布朗斯特-洛里碱，以抑制、抑制或防止亚胺官能硅烷与自身的加成反应，形成亚胺和氨基官能硅烷，以及随后的去氨反应，形成含有共轭碳-碳双键的亚胺官能硅烷和含有至少一种布朗斯特-洛里碱的稳定亚胺官能硅烷。
• Vegetable based dioxanone derivatives, synthesis and uses thereof
  申请人：Binder Paul Thomas

  公开号：US20050234121A1

  公开（公告）日：2005-10-20

  The present invention is directed to carboxylic acid and ester moieties that are attached to a carbon chain that is between 2 and 24 carbons in length wherein, the chain contains at least one dioxanone ring system, said dioxanone being formed from two adjacent carbons in the chain and/or at least one carbon in the chain is substituted with a pendant dioxanone ring system. In preferred embodiments, the carbon chain is a fatty acid residue. The carbons of said chain can be optionally substituted, saturated or unsaturated. When two or more said ester moieties are present, the invention is directed to a polyester such as a triglyceride, that contains multiple carbon chains wherein each chain is independently derivatized such that the triglyceride contains at least one dioxanone ring system, said dioxanone being formed from two adjacent carbons in at least one of said chains. The present invention is also directed to a method of preparing a dioxanone containing composition or fatty acid derivative. The present invention is also directed to coating formulations and polymers that utilize a dioxanone containing composition or fatty acid derivative, and methods of making such coatings and polymers.

  本发明涉及连接到长度在2到24碳之间的碳链上的羧酸和酯基团，其中该链含有至少一个二氧杂环己酮环系统，所述二氧杂环己酮是由链中的两个相邻碳和/或链中的至少一个碳被取代为挂链的二氧杂环己酮环系统而形成的。在优选实施例中，碳链是脂肪酸残基。所述链的碳可以选择性地被取代、饱和或不饱和。当存在两个或更多的酯基团时，该发明涉及一种聚酯，例如三酸甘油酯，其中包含多个碳链，每个链都独立地衍生，使得三酸甘油酯含有至少一个二氧杂环己酮环系统，所述二氧杂环己酮是由至少一个链中的两个相邻碳形成的。本发明还涉及制备含有二氧杂环己酮的组合物或脂肪酸衍生物的方法。本发明还涉及利用含有二氧杂环己酮的组合物或脂肪酸衍生物的涂料配方和聚合物，以及制备此类涂料和聚合物的方法。