stearyl α-D-glucopyranoside | 35176-29-5

• 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: stearyl α-D-glucopyranoside
• 英文别名: Stearyl alpha-D-glucopyranoside；(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-octadecoxyoxane-3,4,5-triol
• CAS: 35176-29-5
• 化学式: C₂₄H₄₈O₆
• 分子量: 432.642
• InChiKey: UFSKIYBOKFBSOA-SJSRKZJXSA-N

物化性质

• 熔点：
  98.0 °C
• 沸点：
  565.4±50.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  30
• 可旋转键数：
  19
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 stearyl α-D-glucopyranoside 在 吡啶 作用下， 生成 stearyl tetrakis(2,3,4,6-O-acetyl)-α-D-glucopyranoside
  参考文献：
  名称：

  Control of headgroup orientation of monolayer by glucolipid

  摘要：

  The mixed monolayers of 1-laurylpyrene-8-carboxylic acid (LP8C) and glucolipids have been studied by measuring pressure-area isotherms and fluorescence spectral changes during compression. LP8C itself does not form a monolayer on pure water and is dispersed as a solid which shows a blue-shifted excimer-like fluorescence at around 470 nm. The 1:1 mixture of LP8C and stearyl alpha-D-glucopyranoside (SGP), however, forms a relatively stable monolayer having a collapse pressure of 36 mN/m. The fluorescence maximum of the LP8C-SGP monolayer is 520 nm. Glycerol alpha-monostearate (GMS), stearyl tetrakis(2,3,4,6-O-methyl)-alpha-D-glucopyranoside (MeSGP), and stearyl tetrakis(2,3,4,6-O-acetyl)-alpha-D-glucopyranoside (AcSGP) do not show the same effect as does SGP, the fluorescence maxima of the mixed monolayers of LP8C and these hydrocarbons being 470 nm. These results can be explained on the basis that the pyrene chromophores are well ordered at the air-water interface by hydrogen bonding between the carboxyl groups of LP8C and the hydroxyl groups of SGP. The fluorescence of dansyllaurylamine suggests that the dehydration from the headgroups of SGP readily occurs during the compression of the monolayer. The easy dehydration from the headgroups may be essential to from the intermolecular hydrogen bonds at the interface.

  DOI：

  10.1021/j100173a052
• 作为产物：
  描述：

  硬脂醇 在 甲醇 、 sodium methylate 、 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 stearyl α-D-glucopyranoside
  参考文献：
  名称：

  Thermotropic and lyotropic properties of long chain alkyl glycopyranosides

  摘要：

  A systematic structure variation of a classical amphiphile (dodecyl-P-D-glucopyranoside) is performed, demonstrating the influence of anomeric linkage, configuration, ring size and flexibility as well as electric charges on the mesophase behaviour. In addition, we have investigated the thermotropic and lyotropic properties of some long chain alkyl glycosides with monosaccharide headgroups. The thermotropism was measured with polarizing microscopy and differential scanning calorimetry, and additionally the lyotropism with FTIR spectroscopy and X-ray diffraction. (C) 2000 Elsevier Science Ireland Ltd. All rights reserved.

  DOI：

  10.1016/s0009-3084(99)00119-x

文献信息

• Effects of lipid packing and intermolecular hydrogen bond on thermotropic phase transition of stearyl glucoside
  作者：Khairul Anwar Ishak、N. Idayu Zahid、Thamil Selvi Velayutham、Mohamad Suffian Mohamad Annuar、Rauzah Hashim

  DOI：10.1016/j.molliq.2019.02.075

  日期：2019.5

  dielectric response of the glycolipid self-assembly system, respectively. A distinctive solid-to-liquid crystal phase transition of α- and β-stearyl glucoside was observed. At ambient temperature we observed semi-crystalline structure for the former and gel phase for the latter. α-Stearyl glucoside showed only one-step transition from semi-crystal to lamellar liquid crystal phase. In contrast, the gel phase

  研究了糖异头物对硬脂基葡糖苷的热致相变的影响。通过差示扫描量热法（DSC）和光学偏振显微镜（OPM）进行标准分析以研究相变。此外，分别使用小角和广角X射线散射（SWAXS）和阻抗谱（IS）来阐明糖脂自组装系统的相结构信息和介电响应。观察到α-和β-硬脂基葡糖苷具有独特的固-液晶相变。在环境温度下，我们观察到前者为半结晶结构，而后者为凝胶相。α-硬脂基葡糖苷仅显示从半结晶相到层状液晶相的一步转变。相反，β-硬脂基葡糖苷的凝胶相在层状液晶相之前显示出几种不同的过渡态。在此，观察到的β-硬脂基葡糖苷多态性的根本原因可能涉及强烈的分子间相互作用，这是由层间氢键和层内范德华力的组合引起的。
• Drilling mud
  申请人：——

  公开号：US20030092579A1

  公开（公告）日：2003-05-15

  The drilling mud with a lowered coefficient of friction comprising a silicate-based mud and a lubricant selected from the group comprising glycosides, alkylpolyalkoxyalcohols, alcohol ester polymers, amine phosphates, starch and combinations thereof.

  降低摩擦系数的钻井泥浆，包括硅酸盐基泥浆和润滑剂，润滑剂选自糖苷、烷基聚烷氧基醇、醇酯聚合物、胺磷酸盐、淀粉及其组合。
• Abdel Salam; El Sawady, Egyptian Journal of Chemistry, 2004, vol. 47, # 2, p. 127 - 142
  作者：Abdel Salam、El Sawady

  DOI：——

  日期：——
• Synthesis and characterization of mesogenic alkyl O-glycosides and their drug release studies
  作者：Saliha Nazir、Hina Daud、Erum Akbar Hussain

  DOI：10.1016/j.molliq.2022.121138

  日期：2023.2
• PROCEDE DE FABRICATION ENZYMATIQUE D'$g(a)-GLUCOSIDES ET D'ESTERS D'$g(a)-GLUCOSIDES, ET UTILISATIONS DES PRODUITS AINSI OBTENUS
  申请人：ULICE S.A.

  公开号：EP0605453A1

  公开（公告）日：1994-07-13