(S)-3-羟基十四烷酸 | 35683-15-9

• 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: (S)-3-羟基十四烷酸
• 英文名称: (S)-3-hydroxytetradecanoic acid
• 英文别名: (S)-3-hydroxymyristic acid；(3S)-3-hydroxytetradecanoic acid
• CAS: 35683-15-9
• 化学式: C₁₄H₂₈O₃
• 分子量: 244.375
• InChiKey: ATRNZOYKSNPPBF-ZDUSSCGKSA-N

物化性质

• 熔点：
  73-74oC
• 沸点：
  376.9±25.0 °C(Predicted)
• 密度：
  0.969±0.06 g/cm3(Predicted)
• 溶解度：
  氯仿（少量溶解）、二氯甲烷（少量溶解）、乙醚（少量溶解）

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  17
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 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

反应信息

• 作为反应物：
  描述：

  (S)-3-羟基十四烷酸 在 palladium on activated charcoal 4-二甲氨基吡啶 、 lithium hydroxide 、 sodium hydroxide 、 ammonium cerium(IV) nitrate 、 WSCD*HCl 、 二苯基膦叠氮化物 、 氢气 、 碳酸氢钠 、 benzotriazol-1-yloxy-tris(dimethylamino)-phosphonium chloride 、 1-羟基苯并三唑一水物 、 三乙胺 、 N,N-二异丙基乙胺 、 三苯基膦 、 三氟乙酸 、 lithium hexamethyldisilazane 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 cyclo{glycyl-lysyl-(γ-methyl-leucyl)-[(2R,3R)-2-methyl-3-undecyl-β-alanyl]}
  参考文献：
  名称：

  Synthesis and Antifungal Activity of Rhodopeptin Analogues. 2. Modification of the West Amino Acid Moiety

  摘要：

  [GRAPHICS]Structure-activity relationships of the west amino acid modified analogues of rhodopeptins, novel antifungal tetrapeptide isolated from Rhodococcus species Mer-N1033, have been investigated, Among the analogues synthesized, 2,2-difluoro and 2-hydroxy derivatives retained the antifungal activity with better physical properties, i.e., solubility or acute toxicity.

  DOI：

  10.1021/ol005630k
• 作为产物：
  描述：

  2-[(7-溴庚基)氧基]四氢-2H-吡喃 在 吡啶 、 copper(l) iodide 、 偶氮二异丁腈 、 三正丁基氢锡 、 L-Selectride 、 magnesium 、 溶剂黄146 、 lithium bromide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 丙酮 、 甲苯 为溶剂， 反应 24.83h， 生成 (S)-3-羟基十四烷酸
  参考文献：
  名称：

  Synthesis, Conformational Analysis, and Stereoselective Reduction of 14-Membered Ring 3-Keto Lactones

  摘要：

  The synthesis of 3-oxo-13-tetradecanolide (5) and its 2-methyl and 2,2-dimethyl derivatives 7 and 8 have been carried out. The keto carbonyls in 5, 7, and 8 have been reduced with varying degrees of stereoselectivity. The stereoselectivity of the reduction depends on the counterion with the borohydride reducing agent, but selectivities approaching 100% have been achieved for 5 and 7. The structure of the reduced products were determined by X-ray crystallography and chemical correlation. Heavy reliance on the stereoselectivity in the Frater dianion alkylation was used. The solution conformation of the beta-keto lactones was found to be based on A both from NMR studies and molecular mechanics calculations. However, we are not able to predict the observed stereoselectivity in the hydride reduction of the ketones using this conformation. Thus we suggest the reduction proceeds through conformation B' in which the two carbonyls are chelated to the counterion. The conformations of the resulting alcohols are more complex and have both inter- and intramolecular hydrogen bonding which control the conformations. The use of polar maps to illustrate similarities and differences in conformations is demonstrated. These conformations are used to rationalize the physical and chemical properties of the beta-keto and beta-hydroxy 14-membered lactones.

  DOI：

  10.1021/jo00103a034

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。
• The Preparation of Optically Pure 3-Hydroxyalkanoic Acid. The Enantioface-differentiating Hydrogenation of the C=O Double Bond with Modified Raney Nickel. XXXVII.
  作者：Masaaki Nakahata、Motomasa Imaida、Hiroshi Ozaki、Tadao Harada、Akira Tai

  DOI：10.1246/bcsj.55.2186

  日期：1982.7

  acid–NaBr–modified Raney nickel catalyst ((R,R)-TA–NaBr–MRNi) gave methyl (R)-3-hydroxyalkanoate (CH3(CH2)nCH(OH)CH2COOCH3, n=0, 6, 8, 10, 12) in an average optical yield of 85%. After the methyl ester had been converted to dicyclohexylammonium salt of 3-hydroxyalkanoic acid, the salt was recrystallized three times from acetonitrile and then treated with acid to give optically pure (R)-3-hydroxyalkanoic acid (CH

  3-氧代链烷酸甲酯 (CH3(CH2)nCOCH2COOCH3, n=0, 6, 8, 10, 12) 在 (R,R)-酒石酸-NaBr-改性阮内镍催化剂（(R, R)-TA-NaBr-MRNi) 生成 (R)-3-羟基链烷酸甲酯 (CH3(CH2)nCH(OH)CH2COOCH3, n=0, 6, 8, 10, 12)，平均光学产率为 85%。在甲酯转化为 3-羟基链烷酸的二环己基铵盐后，该盐从乙腈中重结晶 3 次，然后用酸处理得到光学纯的 (R)-3-羟基链烷酸 (CH3(CH2)nCH(OH) CH2COOH，n=0, 6, 8, 10, 12) 以合理的产率。从与 (S,S)-TA-NaBr-MRNi 的氢化产物中，通过与上述相同的方法获得光学纯的 (S)-3-羟基链烷酸。
• Chemical Synthesis of a Glycolipid Library by a Solid-Phase Strategy Allows Elucidation of the Structural Specificity of Immunostimulation by Rhamnolipids
  作者：Jörg Bauer、Klaus Brandenburg、Ulrich Zähringer、Jörg Rademann

  DOI：10.1002/chem.200600482

  日期：2006.9.18

  variations in the carbohydrate part, the lipid components, and the stereochemistry of the 3-hydroxy fatty acids was designed and synthesized. The enantioselective synthesis of the 3-hydroxy fatty acid building blocks was achieved by employing asymmetric hydrogenation of 3-oxo fatty acids. Glycolipids were prepared by this approach without any intermediary isolation steps, mostly in excellent yields. Final

  描述了通过疏水辅助开关相（HASP）合成的糖脂文库的首次合成。HASP合成可在溶液相步骤和与附着在疏水性二氧化硅载体上的分子进行的固相支持反应之间灵活切换。设计并合成了衍生自先导化合物1-a强免疫刺激鼠李糖脂的糖脂库-碳水化合物部分，脂质成分和3-羟基脂肪酸的立体化学存在差异。通过使用3-氧代脂肪酸的不对称氢化来实现3-羟基脂肪酸结构单元的对映选择性合成。糖脂是通过这种方法制备的，无需任何中间分离步骤，大部分收率都很高。通过酶促酯裂解完成对羧酸的最终脱保护。通过测定细胞因子肿瘤坏死因子α（TNFα）向培养基中的分泌，测试所有制备的鼠李糖脂对人单核细胞的免疫刺激特性。观察到的鼠李糖脂的构效关系表明了一种特定的，基于识别的作用方式，鼠李糖脂的结构变化很小，从而在低微摩尔浓度下对鼠李糖脂的免疫刺激活性产生了强烈影响。
• Synthesis of an analog of biosynthetic precursor Ia of lipid A by an improved method: a novel antagonist containing four (S)-3-hydroxy fatty acids
  作者：Koichi Fukase、Wen-Chi Liu、Yasuo Suda、Masato Oikawa、Akira Wada、Saeko Mori、Arthur J. Ulmer、Ernst Th. Rietschel、Shoichi Kusumoto

  DOI：10.1016/0040-4039(95)01433-0

  日期：1995.10

  Synthesis of an analog of a biosynthetic precursor of lipid A containing four (S)-3-hydroxytetradecanoic acids was effected via an improved synthetic route to investigate the relationship between the bioactivity and the chirality of the 3-hydroxy fatty acid residues in lipid A. The S-analog inhibited endotoxin-induced interleukin-6 (IL-6) production from human peripheral whole blood cells more strongly

  通过改进的合成途径合成脂质A的生物合成前体包含四个（S）-3-羟基十四烷酸的类似物，以研究脂质A中3-羟基脂肪酸残基的生物活性与手性之间的关系。该小号从人末梢全血细胞比更强烈的天然型的生物合成前体与（ -模拟抑制内毒素诱导的白细胞介素-6（IL-6）的生产- [R ）-羟基酸，在LPS诱导的细胞因子释放的一个已知的拮抗剂人外周血单核细胞。
• Synergy among humimycins against methicillin‐resistant <scp> <i>Staphylococcus aureus</i> </scp>
  作者：Robert J. Tancer、Kazim Baynes、Gregory R. Wiedman

  DOI：10.1002/pep2.24197

  日期：2021.5

  specific class of lipopeptides: humimycins. We explored various changes to their structure including altering their hydrophobicity and enantiomeric amino acid substitutions. Of specific note, the “dehydroxy” analogue, synthesized with myristic anhydride, has a 4-fold improved activity against MRSA (USA300) as determined in minimum inhibitory concentration (MIC) assays. When used together, the original

  耐药性和多药耐药性微生物是公共卫生日益严重的问题。在这项工作中，我们调查了脂肽协同作用作为耐甲氧西林金黄色葡萄球菌（ MRSA ）的潜在治疗方法的能力。感染。我们提出了特定类别的脂肽：humimycins的结果。我们探索了其结构的各种变化，包括改变其疏水性和对映体氨基酸取代。特别值得注意的是，与肉豆蔻酸酐合成的“脱羟基”类似物，通过最小抑菌浓度（MIC）测定，对MRSA（USA300）的活性提高了4倍。当一起使用时，原始的humimycin和脱羟基类似物的抗MRSA的MIC低于20μg/ mL。我们还报告了humimycins形成直径小于250 nm的纳米颗粒胶束。这些颗粒可以用作递送多种Humimycin药物的制剂，作为MRSA感染的有效治疗方法。