ricinelaidic acid | 540-12-5

• 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: ricinelaidic acid
• 英文别名: (+)-(R)-ricinelaidic acid；(E,12R)-12-hydroxyoctadec-9-enoic acid
• CAS: 540-12-5
• 化学式: C₁₈H₃₄O₃
• 分子量: 298.466
• InChiKey: WBHHMMIMDMUBKC-XLNAKTSKSA-N

物化性质

• 熔点：
  51～52 1)
• 溶解度：
  DMF：3mg/mL； DMSO：2mg/mL；乙醇：可混溶； PBS（pH 7.2）：2 mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 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

安全信息

• 海关编码：
  2918199090
• 储存条件：
  -20°C，密闭保存，干燥环境中存放。

制备方法与用途

ricinoleic酸是一种含有12-羟基的脂肪酸，并且是环列因B4（LTB4）受体的拮抗剂（在猪中性粒细胞膜上的Ki值为2 μM）。

反应信息

• 作为反应物：
  描述：

  ricinelaidic acid 在 chromium(VI) oxide 、 四氯化碳 、 氢溴酸 、 碳酸氢钠 、 溶剂黄146 作用下， 生成 12-oxo-octadec-trans-10-enoic acid
  参考文献：
  名称：

  Achievement of steady state optimizes results when performing indirect calorimetry

  摘要：

  BACKGROUND: The use of steady state as the endpoint for performance of indirect calorimetry (IC) is controversial. We designed this prospective study to evaluate the necessity and significance of achieving steady state. METHODS: Patients with respiratory failure placed on mechanical ventilation in a short‐ or long‐term acute care unit at any 1 of 3 university‐based urban hospitals were eligible for the study. The 24‐hour total energy expenditure (TEE) was determined by a Nellcor Puritan Bennett 7250 continuous IC monitor. Measured gas exchange parameters were obtained and averaged every 1 minute for the initial hour and then every 15 minutes for the next 23 hours. Over the initial hour, resting energy expenditure (REE) was averaged for intervals over the first 20, 30, 40, and 60 minutes, and for various definitions of steady state where oxygen consumption (VO2) and carbon dioxide production (VCO2) changed by <10%, 15%, and 20%. Coefficient of variation (CV) was calculated for VO2 over the first 30 minutes of study. RESULTS: Twenty‐two patients (mean age, 52.8 years, 59% male, mean Acute Physiology and Chronic Health Evaluation (APACHE III) score 42.0) were entered in the study. The best correlation between short‐term “snapshot” REE and the 24‐hour TEE was achieved by the steady‐state period defined by the most stringent criteria (change in VO2 and VCO2 by <10%). The average REE for all steady‐state and interval periods correlated significantly to TEE with no significant difference in the absolute values for REE and TEE. Adding 10% for an activity factor to the average REE for each steady‐state and interval period again correlated to TEE in a similar fashion with the same R value, but the absolute values for REE + 10% for all steady‐state and interval periods were significantly different than the corresponding TEE. In those patients with less variation (CV for VO2 < or = 9.0), the REE obtained for the steady‐state period defined by the most stringent criteria still had the best correlation, but similar correlation could be obtained by interval testing of > or = 30‐minute duration. In those patients with greater variation (CV for VO2 >9.0), interval testing of at least 60 minutes or more was required to attain levels of correlation similar to that achieved by the steady‐state period defined by the most stringent criteria. CONCLUSIONS: These data support the use of steady state, best defined as an interval of 5 consecutive minutes whereby VO2 and VCO2 change by <10%. The mean REE from this period correlates best to the 24‐hour TEE regardless of CV. IC testing can be completed after achievement of steady state. Activity factors of 10% to 15% should not be added to the steady‐state REE, because this practice significantly decreases the accuracy. In patients who fail to achieve steady state, the CV helps to determine the appropriate duration of IC testing. In those patients with a low CV (< or = 9.0), 30‐minute test duration is adequate. In patients with CV >9.0, test duration of at least 60 minutes may be required. These latter patients should be considered for 24‐hour IC testing.

  DOI：

  10.1177/014860710302700116
• 作为产物：
  描述：

  蓖麻油酸 在 二苯二硫醚 作用下， 以 苯 为溶剂， 生成 ricinelaidic acid
  参考文献：
  名称：

  合成des（R）-反式-11-Hydroxy-8-dodecensäure-lactons（Recieifeiolid）

  摘要：

  雷西福利内酯的合成

  DOI：

  10.1002/hlca.19760590306

文献信息

• Reagents for organic synthesis. Part 3. Tin-mediated esterification in macrolide synthesis
  作者：Kosta Steliou、Marc Andre Poupart

  DOI：10.1021/ja00362a018

  日期：1983.11

  Esterification interne d'ω-hydroxyacides par action de Bu 2 SnO basee sur un processus «template». Application a la synthese de zearalenone, ingramycene, nodusmicine, pyrenophorine et vermiculine. Les β- et ω-aminoacides a longue chaine conduisent preferentiellement a des polymeres mais on arrive cependant a obtenir des lactames a 5, 6 et 7 chainons a partir des ω-aminoacides correspondants

  Esterification interne d'ω-hydroxyacides par action de Bu 2 SnO basee sur un processus «template»。应用 玉米赤霉烯酮、靛蓝霉烯、nodusmicine、pyrenophorine 和 vermiculine 的合成。Les β- et ω-aminoacides a longue chaine conduisent preentiellement a despolymeres mais on obtenir des lactames a 5, 6 et 7 chainons a partir des ω-aminoacides 对应物
• An effective method for the synthesis of carboxylic esters and lactones using substituted benzoic anhydrides with Lewis acid catalysts
  作者：Isamu Shiina

  DOI：10.1016/j.tet.2003.12.013

  日期：2004.2

  benzoic anhydride having electron withdrawing substituent(s) is developed by the promotion of Lewis acid catalysts. In the presence of a catalytic amount of TiCl2(ClO4)2, various carboxylic esters are prepared in high yields through the formation of the corresponding mixed-anhydrides from 3,5-bis(trifluoromethyl)benzoic anhydride and carboxylic acids. The combined catalyst consisting of TiCl2(ClO4)2 together

  通过促进路易斯酸催化剂，开发了一种使用具有吸电子取代基的苯甲酸酐合成羧酸酯和内酯的有效的混合酸酐方法。在催化量的TiCl 2（ClO 4）2的存在下，通过由3,5-双（三氟甲基）苯甲酸酐和羧酸形成相应的混合酸酐，可以高收率制备各种羧酸酯。由TiCl 2（ClO 4）2组成的组合催化剂与氯代三甲基硅烷一起用作由游离羧酸和醇与4-（三氟甲基）苯甲酸酐合成羧酸酯的有效催化剂。在温和的反应条件下，通过将4-（三氟甲基）苯甲酸酐和钛（IV）催化剂与氯代三甲基硅烷一起使用，可以从游离的ω-羟基羧酸制得各种大分子内酯。在室温下，在催化量的TiCl 2（ClO 4）2存在下，还使用4-（三氟甲基）苯甲酸酐促进了三甲基甲硅烷基ω-（三甲基甲硅烷氧基）羧酸酯的内酯化。。通过使用4-（三氟甲基）苯甲酸酐，通过促进催化量的Hf（OTf）4，根据该混合酸酐法成功地合成了头孢菌素D的合成中间体8元环内酯。
• Elongation of the Hydrophobic Chain as a Molecular Switch: Discovery of Capsaicin Derivatives and Endogenous Lipids as Potent Transient Receptor Potential Vanilloid Channel 2 Antagonists
  作者：Aniello Schiano Moriello、Silvia López Chinarro、Olalla Novo Fernández、Jordi Eras、Pietro Amodeo、Ramon Canela-Garayoa、Rosa Maria Vitale、Vincenzo Di Marzo、Luciano De Petrocellis

  DOI：10.1021/acs.jmedchem.8b00734

  日期：2018.9.27

  potent pharmacological tools and endogenous modulators. Here we describe the discovery of novel synthetic long-chain capsaicin derivatives as potent TRPV2 antagonists in comparison to the totally inactive capsaicin, the role of their hydrophobic chain, and how the structure–activity relationships of such derivatives led, through a ligand-based approach, to the identification of endogenous long-chain

  瞬时受体电位香草2型（TRPV2）蛋白是非选择性Ca 2+由于缺乏可用的选择性和有效的药理学工具和内源性调节剂，TRPV亚家族的可渗透通道成员仍被认为是孤立的TRP通道。在这里，我们描述了通过完全基于配体的方法发现的新型合成长链辣椒素衍生物作为强效TRPV2拮抗剂（与完全无活性的辣椒素相比），它们的疏水链的作用以及这些衍生物的结构-活性关系如何导致的发现。 ，以鉴定充当TRPV2拮抗剂的内源性长链脂肪酸乙醇酰胺或伯酰胺。合成的和内源性的拮抗剂都表现出对以不同的动力学特征为特征的已知TRPV2激动剂的不同抑制作用。
• Gelating abilities of metal salts of ricinelaidic acid. Structural and rheological considerations
  作者：Mohan Zhang、Richard G. Weiss

  DOI：10.1002/poc.3826

  日期：2019.1

  and zinc(II) are inefficient gelators, while the calcium salt can gelate various organic liquids and the sodium salt is an ambidextrous gelator. Also, gels of calcium and sodium salts in nitrobenzene and/or in water are among the few known examples with crystalline gelator networks that exhibit thixotropic behavior. Structural insights from FT‐IR and powder X‐ray diffraction indicate that the specific

  天然存在的顺式异构体D-蓖麻油酸的反式异构体蓖麻油酸（D-REA）的金属盐的胶凝能力已在多种液体中进行了研究。D‐REA由于其弯曲的形状和较低的熔化温度，因此不是很好的胶凝剂。尽管在形成金属盐时有助于D-REA的聚集，其胶凝能力根据金属阳离子的性质而有很大差异。与镍（II），铜（II）和锌（II）形成的盐是无效的胶凝剂，而钙盐可以使各种有机液体胶凝，而钠盐则是一种灵巧的胶凝剂。同样，在硝基苯和/或水中的钙盐和钠盐的凝胶是少数具有结晶触变剂网络且表现出触变行为的已知例子。FT-IR和粉末X射线衍射的结构见解表明，盐在其首基处相互作用的特殊性质导致了不同的堆积排列，并改变了二次相互作用中一维生长的驱动力强度。D‐REA胶凝能力之间的简短比较以及来自相关结构酸9,10-二氧十八碳烯酸的相应盐。提供了对金属羧酸盐中心的相互作用之间的关系，它们形成分子凝胶的能力及其聚集结构的性质的见解。
• A Novel Method for the Preparation of Macrolides from ω-Hydroxycarboxylic Acids
  作者：Isamu Shiina、Teruaki Mukaiyama

  DOI：10.1246/cl.1994.677

  日期：1994.4

  An efficient method for the synthesis of macrolides directly from ω-hydroxycarboxylic acids is established by using 4-(trifluoromethyl)benzoic anhydride and a catalytic amount of active titanium(IV) salts together with chlorotrimethylsilane under mild conditions.

  建立了一种从ω-羟基羧酸直接合成大环内酯的高效方法，使用4-(三氟甲基)苯甲酸酐和少量活性钛(IV)盐以及氯三甲基硅烷，在温和条件下进行。

表征谱图