16-hydroxyhexadecanoic acid methyl ester | 36575-67-4

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 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: 16-hydroxyhexadecanoic acid methyl ester
• 英文别名: methyl 16-Hydroxyhexadecanoate
• CAS: 36575-67-4
• 化学式: C₁₇H₃₄O₃
• 分子量: 286.455
• InChiKey: AOTMRIXFFOGWDT-UHFFFAOYSA-N

物化性质

• 熔点：
  54-55 °C(Solv: ligroine (8032-32-4))
• 沸点：
  374.7±15.0 °C(Predicted)
• 密度：
  0.923±0.06 g/cm3(Predicted)
• 保留指数：
  2335.2

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  20
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  16-hydroxyhexadecanoic acid methyl ester 在 lithium aluminium tetrahydride 、 甲基磺酰氯 作用下， 以 乙醚 、 氯仿 为溶剂， 生成 16-溴-1-十六烷醇
  参考文献：
  名称：

  一系列单链1，omega-bis（phosphocholines）的一般合成和聚集行为。

  摘要：

  描述了一系列具有22至32个碳原子的偶数链长的聚亚甲基-1，ω-双（磷酸胆碱）的合成和理化特性。提出了两种新的合成策略，用于制备长链1，ω-二醇作为烃类结构单元。通过低温透射电子显微镜（cryo-TEM），差示扫描量热法（DSC）和傅里叶变换红外光谱（FTIR）研究了单链双亲性嗜蓝菌的温度依赖性自组装。

  DOI：

  10.1002/chem.200601866
• 作为产物：
  描述：

  十四烷 生成 16-hydroxyhexadecanoic acid methyl ester
  参考文献：
  名称：

  Tulloch,A.P.; Spencer,J.F.T., Canadian Journal of Chemistry, 1968, vol. 46, p. 1523 - 1528

  摘要：

  DOI：

文献信息

• Structure-antitumor Activity Relationship of Semi-synthetic Spicamycin Derivatives.
  作者：TERUYUKI SAKAI、HIROYUKI KAWAI、MASARU KAMISHOHARA、ATSUO ODAGAWA、AKASHI SUZUKI、TAKESHI UCHIDA、TOMIKO KAWASAKI、TAKASHI TSURUO、NOBORU OTAKE

  DOI：10.7164/antibiotics.48.1467

  日期：——

  New derivatives of spicamycin modified at the fatty acid moieties of the molecule were synthesized and their structure-activity relationships were examined. The antitumor activity was greatly influenced by modification of the fatty acid moieties to tetradecadienoyl or dodecadienoyl analogues exhibiting better antitumor activity against COL-1 human colon cancer xenograft than SPM VIII.

  新合成了一系列在分子脂肪酸部分进行了修饰的斯匹卡霉素衍生物，并研究了它们的构效关系。通过对脂肪酸部分进行修饰，将其转化为十四碳二烯酸或十二碳二烯酸类似物，这些衍生物对COL-1人结肠癌异种移植模型的抗肿瘤活性显著优于SPM VIII。
• [EN] ENDOSOMOLYTIC AGENTS FOR GENE THERAPY<br/>[FR] AGENTS ENDOSOMOLYTIQUES POUR THÉRAPIE GÉNIQUE
  申请人：UCB BIOPHARMA SPRL

  公开号：WO2018060280A1

  公开（公告）日：2018-04-05

  Compounds of formula (I), wherein Ar is an aryl group optionally further substituted with one or more groups R3; A is a lipophilic, hydrophobic moiety; R1 is a phosphodiester, phosphotriester, thioether or amide group; X is an unsubstituted or substituted C6 to C24 alkylene or alkenylene group, which is optionally interrupted by one or more -NR9-, -O- or -S- linkages, R2 is -YC(R4)(R5)CO2R6; and pharmaceutically acceptable salts or solvates thereof are useful as endosomolytic agents particularly for the delivery of nucleic acids useful in gene therapy.

  式(I)的化合物，其中Ar是一种芳基，可选择性地进一步取代为一个或多个基团R3；A是一个亲脂性、疏水性的基团；R1是一个磷酸二酯、磷酸三酯、硫醚或酰胺基团；X是一个未取代或取代的C6到C24烷基或烯基基团，该基团可被一个或多个-NR9-、-O-或-S-键所中断；R2是-YC(R4)(R5)CO2R6；以及其药学上可接受的盐或溶剂化合物，可用作内体溶解剂，特别用于传递在基因治疗中有用的核酸。
• Synthesis of Tenuilobine, a Bis-polyamine Alkaloid fromOncinotis tenuiloba, and Its Transamidation to Isotenuilobine
  作者：Martin K.-H. Doll、Armin Guggisberg、Manfred Hesse

  DOI：10.1002/hlca.19960790221

  日期：1996.3.20

  From the leaves of Oncinotis tenuiloba STAPF, a novel polyamine alkaloid, tenuilobine (9), was isolated. This paper presents the synthesis of 9, as well as the base-catalyzed Zip reaction of 9, leading to the transamidation product isotenuilobine (10). The structure of 10 was further confirmed by 2D-NMR correlation spectroscopy. For analytical purposes, the bis-polyamines 9 and 10 were converted into

  从Oncinotis tenuiloba STAPF的叶子中，分离出一种新型的多胺生物碱tenuilobine（9）。本文介绍了合成的9，以及碱催化邮编的反应9，导致转酰氨产物isotenuilobine（10）。通过2D-NMR相关光谱进一步确认了10的结构。为了分析目的，将双聚胺9和10分别转化为其五乙酰基衍生物12和11，它们可以通过反相HPLC容易地分离。
• An expedient synthesis of 5-<i>n</i>-alkylresorcinols and novel 5-<i>n</i>-alkylresorcinol haptens
  作者：Kirsti Parikka、Kristiina Wähälä

  DOI：10.3762/bjoc.5.22

  日期：——

  The first synthesis of bioactive long alkyl chain 5-n-alkylresorcinols, present in whole grain products, by a novel modification of the Wittig reaction is described. All the main long chain 5-n-alkylresorcinols present in rye and wheat, including C₂₃ and C₂₅ analogues and haptens, which have not been previously prepared, were synthesised. Microwave-promoted reactions of a semi-stabilized ylid and alkanals in water gave good yields in both pressurized and open systems. An alternative microwave-promoted synthesis starting from non-stabilized alkyltriphenylphosphonium salts and 3,5-dimethoxybenzaldehyde worked as well. Aqueous media were suitable for the reactions even if the starting materials were not soluble in water. The 5-n-alkylresorcinols are potential biomarkers of whole grain intake, and the new hapten derivatives of 5-n-alkylresorcinols will open the way for the immunochemical detection techniques of alkylresorcinols.

  描述了通过一种新颖的Wittig反应改进合成生物活性长烷基链5-烷基间苯二酚，这种物质存在于全谷物产品中。合成了黑麦和小麦中所有主要的长链5-烷基间苯二酚，包括C23和C25类似物以及以前未制备的半抗原。在水中，半稳定叶立德和烷醛的微波促进反应在加压和开放系统中均获得良好产率。另一种微波促进合成方法是从非稳定的烷基三苯基膦盐和3,5-二甲氧基苯甲醛出发。即使起始材料在水中不溶解，水介质也适用于这些反应。5-烷基间苯二酚是全谷物摄入的潜在生物标志物，而新的5-烷基间苯二酚半抗原衍生物将为烷基间苯二酚的免疫化学检测技术打开道路。
• Synthesis of 23-, 25-, 27-, and 29-Membered (<i>Z</i>)-Selective Unsaturated and Saturated Macrocyclic Lactones from 16- and 17-Membered Macrocyclic Lactones and Bromoalcohols by Wittig Reaction, Yamaguchi Macrolactonization, and Photoinduced Decarboxylative Radical Macrolactonization
  作者：Tomoya Iwasaki、Yuka Tajimi、Kenta Kameda、Callum Kingwell、William Wcislo、Kazuyuki Osaka、Mugen Yamawaki、Toshio Morita、Yasuharu Yoshimi

  DOI：10.1021/acs.joc.9b00870

  日期：2019.6.21

  A new strategy for the synthesis of 23-, 25-, 27-, and 29-membered (Z)-selective unsaturated and saturated macrocyclic lactones from commercially available 16- and 17-membered macrocyclic lactones and bromoalcohols by Wittig reaction, Yamaguchi macrolactonization, and photoinduced decarboxylative radical macrolactonization is described. The position of the unsaturated part in the macrocyclic lactones

  一种新的策略，可通过Wittig反应，山口宏内酯化，由Wittig反应从市售的16和17元大环内酯和溴代醇合成23、25、27和29元（Z）选择性不饱和和饱和大环内酯，并且描述了光诱导的脱羧自由基大内酯化。大环内酯中不饱和部分的位置可以通过改变原料中的碳数来控制。该方案可以从简单的起始原料容易地获得所需的大环（Z）-选择性不饱和和饱和大环内酯。