4-hydroxypentadecan-2-one

• 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: 4-hydroxypentadecan-2-one
• 英文别名: 4-hydroxy-pentadecan-2-one；4-Hydroxy-pentadecan-2-on；4-Hydroxypentadecan-2-one
• 化学式: C₁₅H₃₀O₂
• 分子量: 242.402
• InChiKey: BSWVGIFZMYWHHG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 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：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  十二醛 、 2-(氯甲基)-3,5-二氧杂-1-己烯 在 indium 、 1,2-二溴乙烷 作用下， 以 四氢呋喃 、 水 为溶剂， 以50%的产率得到4-hydroxypentadecan-2-one
  参考文献：
  名称：

  A useful synthetic equivalent of an acetone enolate

  摘要：

  2-Methoxymethoxy-3-chloropropene derived organometallics act as synthetic equivalents of an acetone enolate. Indium-promoted reaction of this reagent with aldehydes affords aldol adducts in moderate to excellent yields. When the reaction was performed with zinc, aldol products were isolated in protected form as the corresponding MOM-enol ethers. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.09.113

文献信息

• [EN] LIPID A MIMICS, METHODS OF PREPARATION, AND USES THEREOF<br/>[FR] MIMÉTIQUES DE LIPIDE A, PROCÉDÉS DE PRÉPARATION, ET LEURS UTILISATIONS
  申请人：IMMUNOVACCINE TECHNOLOGIES INC

  公开号：WO2016109880A1

  公开（公告）日：2016-07-14

  The invention provides lipid A mimics in which one or both of the sugar residues of a natural lipid A disaccharide backbone has been replaced with an aromatic group. These lipid A mimics may further differ from a natural lipid A molecule with respect to other structural characteristics, such as, a different number of phosphate groups present, changes in the number, structure and location of lipid chains and/or changes in the spacing and linkage of the sugar residues (or their aromatic replacements). The lipid A mimics may be lipid A agonists and as such may be useful as immunostimulatory agents in inducing or patenting an antibody and/or cell-mediated immune response, or may be lipid A antagonists and as such may be useful in treating or preventing a lipopolysaccharide (LPS)/lipid A-mediated disease or disorder. Also provided are methods for preparing the lipid A mimics.

  本发明提供了脂多糖A（lipid A）类似物，其中天然脂多糖A二糖骨架的一个或两个糖残基已被芳香族基团取代。这些脂多糖A类似物可能还与天然脂多糖A分子在其他结构特征方面有所不同，例如，存在不同数量的磷酸基团，脂肪链的数量、结构和位置发生变化和/或糖残基（或其芳香族替代物）的间距和连接发生变化。这些脂多糖A类似物可以是脂多糖A激动剂，因此可用作免疫刺激剂，诱导或产生抗体和/或细胞介导的免疫反应，或者可以是脂多糖A拮抗剂，因此可用于治疗或预防脂多糖体（LPS）/脂多糖A介导的疾病或障碍。还提供了制备这些脂多糖A类似物的方法。
• Lipid A mimics, methods of preparation, and uses thereof
  申请人：Immunovaccine Technologies Inc.

  公开号：US10988500B2

  公开（公告）日：2021-04-27

  The invention provides lipid A mimics in which one or both of the sugar residues of a natural lipid A disaccharide backbone has been replaced with an aromatic group. These lipid A mimics may further differ from a natural lipid A molecule with respect to other structural characteristics, such as, a different number of phosphate groups present, changes in the number, structure and location of lipid chains and/or changes in the spacing and linkage of the sugar residues (or their aromatic replacements). The lipid A mimics may be lipid A agonists and as such may be useful as immunostimulatory agents in inducing or patenting an antibody and/or cell-mediated immune response, or may be lipid A antagonists and as such may be useful in treating or preventing a lipopolysaccharide (LPS)/lipid A-mediated disease or disorder. Also provided are methods for preparing the lipid A mimics.

  本发明提供了脂质 A 拟体，其中天然脂质 A 双糖骨架的一个或两个糖残基已被芳香基团取代。这些脂质 A 拟态物在其他结构特征方面可能与天然脂质 A 分子有进一步的不同，例如存在不同数量的磷酸基团，脂质链的数量、结构和位置发生变化，以及/或糖残基（或其芳香基替代物）的间距和连接发生变化。脂质 A 拟态物可以是脂质 A 激动剂，因此可用作免疫刺激剂，诱导或激发抗体和/或细胞介导的免疫反应；也可以是脂质 A 拮抗剂，因此可用于治疗或预防脂多糖（LPS）/脂质 A 介导的疾病或紊乱。此外，还提供了制备脂质 A 模仿物的方法。
• Most Infectious Complications in Parenterally Fed Trauma Patients Are Not Due to Elevated Blood Glucose Levels
  作者：Kenneth A. Kudsk、Anne Laulederkind、M. Keith Hanna

  DOI：10.1177/0148607101025004174

  日期：2001.7

  Objective: To determine the relationship between hyperglycemia and infectious complications in nutritional studies of trauma patients. Methods: Retrospective review of serum glucose values in two published randomized, prospective studies of patients receiving either enteral or parenteral feeding (trial 1) or isonitrogenous, isocaloric enteral diets (trial 2). Trial 2 also included patients prospectively followed who received little or no enteral feeding. Results: Patients randomized to enteral or parenteral feeding in trial 1 exhibited no significant differences in the highest recorded serum glucose (SG) until the fourth or fifth day after protocol entry. SG tended to be higher in infected than noninfected patients in the first 4 hospital days, but SG was far below values considered to increase the risk for infection (SG > 220 mg/dL). In trial 2, glucose levels tended to be slightly higher in infected than in noninfected patients within the first 5 days reaching statistical significance by day 5. Unfed control patients had similar SG values but significantly more major infectious complications. Conclusions: Patients developing infections had slightly higher SG levels than noninfected patients early in admission, but these SG values were far below levels considered a risk for infective complications. Significant hyperglycemia does not explain differences in infectious complications in critically ill trauma patients randomized to various routes and types of nutrition. (Journal of Parenteral and Enteral Nutrition 25:174–179, 2001)
• MUC1 Based Glycolipopeptide Vaccine with Adjuvant
  申请人：PETERSON Scott

  公开号：US20120219617A1

  公开（公告）日：2012-08-30

  Provided herein are liposomal glycolipopeptidic vaccine formulations comprising an adjuvant and an immunogen for immunotherapy and/or treatment of cancer.
• PROCESS FOR DETERGENT-FREE PRODUCTION OF OUTER MEMBRANE VESICLES OF A GRAM-NEGATIVE BACTERIUM
  申请人：Van De Waterbeemd Bas

  公开号：US20140147469A1

  公开（公告）日：2014-05-29

  The present invention relates to the fields of medical microbiology and vaccines. In particular the invention relates to a process for detergent-free preparation of outer membrane vesicles (OMV) of Gram negative bacteria for use in vaccines, to OMV obtainable by said process, and to a pharmaceutical composition comprising such OMV. The present invention further relates to the use of OMV of the present invention as a medicament in particular for use in a method for eliciting an immune response.