2-十六烷基十八烷酰氯 | 153252-39-2

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 酰卤
• 中文名称: 2-十六烷基十八烷酰氯
• 英文名称: 2-(n-hexadecyl)stearic acid chloride
• 英文别名: 2-Hexadecyloctadecanoyl chloride；2-hexadecyloctadecanoyl chloride
• CAS: 153252-39-2
• 化学式: C₃₄H₆₇ClO
• 分子量: 527.358
• InChiKey: FLOXZHHLFQNHMM-UHFFFAOYSA-N

物化性质

• 沸点：
  558.4±18.0 °C(Predicted)
• 密度：
  0.880±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  17.7
• 重原子数：
  36
• 可旋转键数：
  31
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-十六烷基十八烷酰氯 在 甲醇 、 sodium methylate 、 三乙胺 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 12.0h， 生成 <2-(2-hexadecyloctadecanoylamido)ethyl>-β-D-galactoside
  参考文献：
  名称：

  Syntheses of Novel Galoctosyl Ligands for Liposomes and the Influence of the Spacer on Accumulation in the Rat Liver.

  摘要：

  我们将半乳糖基配体修饰到脂质体表面。首先，我们确定半乳糖基团是否暴露在脂质体表面。然后，我们研究了这些配体对大鼠肝脏中脂质体积累的影响。我们引入了一个聚乙二醇基团作为间隔基。在测试的各种配体中，具有三或四聚乙二醇间隔基的配体导致脂质体在肝脏中积累最多。带有三或四聚乙二醇间隔基配体的脂质体被蓖麻凝集素聚集。另一方面，修饰有单或二聚乙二醇间隔基配体的脂质体没有明显聚集。这些结果显示了归巢装置与配体锚定基之间间隔基的重要性。

  DOI：

  10.1248/bpb.18.740
• 作为产物：
  描述：

  2-十六烷基十八烷酸 在 氯化亚砜 作用下， 反应 3.0h， 生成 2-十六烷基十八烷酰氯
  参考文献：
  名称：

  Syntheses of Novel Galoctosyl Ligands for Liposomes and the Influence of the Spacer on Accumulation in the Rat Liver.

  摘要：

  我们将半乳糖基配体修饰到脂质体表面。首先，我们确定半乳糖基团是否暴露在脂质体表面。然后，我们研究了这些配体对大鼠肝脏中脂质体积累的影响。我们引入了一个聚乙二醇基团作为间隔基。在测试的各种配体中，具有三或四聚乙二醇间隔基的配体导致脂质体在肝脏中积累最多。带有三或四聚乙二醇间隔基配体的脂质体被蓖麻凝集素聚集。另一方面，修饰有单或二聚乙二醇间隔基配体的脂质体没有明显聚集。这些结果显示了归巢装置与配体锚定基之间间隔基的重要性。

  DOI：

  10.1248/bpb.18.740

文献信息

• Synthesis and Application of Neoglycolipids for Liposome Modification.
  作者：Naokazu MURAHASHI、Hiroshi ISHIHARA、Masahiro SAKAGAMI、Atsushi SASAKI

  DOI：10.1248/bpb.20.704

  日期：——

  We synthesized various glycolipid derivatives and examined the in vivo behaviors of liposomes modified with these movel glycolipid derivatives. Gal-t-pas (1, 8-(2-hexadecyloctadecanoylamino)-3, 6-dioxaoctyl}-β-D-galactoside), Lac-t-psa (3, 8-(2-hexadecyloctadecanoylamino)-3, 6-dioxaoctyl β-D-lactoside) and GalNAc-t-psa (4, 8-(2-hexadecyloctadecanoylamino)-3, 6-dioxaoctyl 2-acetamido-β-D-galactopyranoside) modified liposomes were recognized by the liver. Lac-t-psa (3) modified liposome was accumulated to the highest degree, followed by GalNAc-t-psa (4) modified liposome and then Gal-t-psa (1) modified liposome. The intrahepatic distributions of Gal-t-psa (1), GalNAc-t-psa (4), Glc-t-psa (2, 8-(2-hexadecyloctadecanoylamido)-3, 6-dioxaoctylβ-D-glucopyranoside) and Lac-t-psa (3) modified liposomes were investigated. GalNAc-t-psa (4) and Lac-t-psa (3) modified liposome were accumulated to greater extents than Gal-t-psa (1) modified liposome in hepatic parenchymal cells. The intrahepatic distribution of these liposomes showed that Lac-t-psa (3) and GalNAc-t-psa (4) were preferable to Gal-t-psa (1) for the selective delivery of liposomes to hepatic parenchymal cells.

  我们合成了多种甘油脂衍生物，并检查了用这些新型甘油脂衍生物修饰的脂质体在体内的行为。Gal-t-pas (1, 8-(2-十六烷基十八酸酰胺)-3, 6-二氧八烯}-β-D-半乳糖苷)、Lac-t-psa (3, 8-(2-十六烷基十八酸酰胺)-3, 6-二氧八烯 β-D-乳糖苷) 和 GalNAc-t-psa (4, 8-(2-十六烷基十八酸酰胺)-3, 6-二氧八烯 2-乙酰氨基-β-D-半乳糖吡喃糖苷) 修饰的脂质体被肝脏识别。Lac-t-psa (3) 修饰的脂质体积累程度最高，其次是 GalNAc-t-psa (4) 修饰的脂质体，最后是 Gal-t-psa (1) 修饰的脂质体。我们研究了 Gal-t-psa (1)、GalNAc-t-psa (4)、Glc-t-psa (2, 8-(2-十六烷基十八酸酰胺)-3, 6-二氧八烯 β-D-葡萄糖吡喃糖苷) 和 Lac-t-psa (3) 修饰脂质体在肝脏内的分布情况。GalNAc-t-psa (4) 和 Lac-t-psa (3) 修饰的脂质体在肝实质细胞中的积累程度大于 Gal-t-psa (1) 修饰的脂质体。这些脂质体的肝内分布显示，Lac-t-psa (3) 和 GalNAc-t-psa (4) 在选择性地将脂质体输送至肝实质细胞方面比 Gal-t-psa (1) 更为理想。
• Hepatic Accumulation of Glutamic Acid Branched Neogalactosyllipid Modified Liposomes.
  作者：Naokazu MURAHASHI、Hiroshi ISHIHARA、Atsushi SASAKI、Masahiro SAKAGAMI、Hiroshi HAMANA

  DOI：10.1248/bpb.20.259

  日期：——

  We synthesized branched type galactosyllipid derivatives for liposome modification for the targeting of asialoglycoprotein receptors on the surface of liver cells. Galactose was coupled to the α- and γ-carboxyl groups of glutamic acid via a triethyleneglycol spacer, then this glutamic moiety was bound to the lipid anchor. Ricinus communis agglutinin (RCA120) induced the agglutination of liposomes modified with mono-, bi- and tri-antennary neogalactosyllipid. With the bi- or tri-antennary derivatives, agglutination was observed at fewer galactosyl residues on the liposomes.We examined the effect of the branching structure in vivo. The difference in accumulation of liposomes between non-branched type neogalactosyllipid and branched type neogalactosyllipid was not large. Liver accumulation of liposomes depended on the galactosyl residues. The number of galactosyl residues was more effective for accumulation in the liver than for branching.We studied the effect of asialofetuin preinjection on the hepatic accumulation of neogalactosyllipid modified liposomes. Hepatic accumulation of liposomes was inhibited by preinjection of asialofetuin. The effect of preinjection was almost equal among the ligands. These results show that the saccharide density on the liposome surface seemed to be a more important factor than the branching structure of the ligand for liver targeting.

  我们合成了支链型半乳糖脂衍生物，用于脂质体修饰，以靶向肝细胞表面的asialoglycoprotein受体。半乳糖通过三乙二醇间隔与谷氨酸的α-和γ-羧基偶联，然后该谷氨酸分子与脂质锚结合。蓖麻凝集素（RCA120）可诱导单、双和三触角新半乳糖脂修饰的脂质体发生凝集。我们研究了分支结构对体内脂质体的影响。非分支型新半乳糖苷脂和分支型新半乳糖苷脂的脂质体积累差异不大。肝脏脂质体的积累取决于半乳糖基残基。我们研究了asialofetuin预注射对新半乳糖苷脂修饰脂质体肝脏蓄积的影响。预注射asialofetuin抑制了脂质体的肝脏蓄积。不同配体的预注射效果几乎相同。这些结果表明，在肝脏靶向作用中，脂质体表面的糖密度似乎比配体的分支结构更为重要。
• Physicochemical Studies on the Phospholipid Bilayer Incorporated.
  作者：Hideo KANEKO、Naokazu MURAHASHI、Atsushi SASAKI、Harutami YAMADA、Masahiro SAKAGAMI、Masahiro IKEDA

  DOI：10.1248/cpb.45.951

  日期：——

  With the intention of obtaining a novel liposome as a drug carrier able to avoid clearance by the reticuloendothelial system (RES), the authors synthesized two sialoglycolipids, i.e., 2-O-(8-hexadecanoylamino-3, 6-dioxaoctyl)-β-N-acetylneuraminic acid sodium salt (Sia-t-pa) and 2-O-[8-(2-hexadecyloctadecanoylamino)-3, 6-dioxaoctyl]-β-N-acetylneuraminic acid sodium salt (Sia-t-psa) and modified the surface of their liposomal membrane.Sia-t-pa was found to be eluted from the liposomal membrane by serum albumin, whereas Sia-t-psa was not, using the gel filtration method. In order to clarify the reason why there was such a difference between Sia-t-pa and Sia-t-psa, we investigated the properties of the phospholipid bilayer-incorporated sialoglycolipids physicochemically.The effect of the anchor structure of the sialoglycolipids, i.e., single acyl chain (Sia-t-pa) or double acyl chain (Sia-t-psa), on the fluidity and calorimetric properties was noticeably different. It was inferred that the effect was attributable to a difference in the position of the sialoglycolipid incorporated in the bilayer membrane.

  为了获得一种新型脂质体作为药物载体，以避免被网状内皮系统（RES）清除，作者合成了两种sialoglycolipids，即：2-O-(8-hexadecanoylamino-3, 6-dioxaoctyl)-β-N-乙酰神经氨酸钠盐（Sia-t-pa）、2-O-(8-hexadecyloctadanoylamino-3, 6-dioxaoctyl)-β-N-acetylneuraminic acid sodium salt (Sia-t-pa)和 2-O-[8-(2-hexadecyloctadanoylamino)-3, 6-dioxaoctyl]-β-N-acetylneuraminic acid sodium salt (Sia-t-psa)，并对其脂质体膜表面进行了修饰。使用凝胶过滤法发现，血清白蛋白能从脂质体膜上洗脱 Sia-t-pa，而 Sia-t-psa 却不能。为了弄清 Sia-t-pa 和 Sia-t-psa 之间存在这种差异的原因，我们从理化角度研究了磷脂双分子层包合的硅氧烷糖脂的特性。硅氧烷糖脂的锚结构（即单酰基链（Sia-t-pa）或双酰基链（Sia-t-psa））对流动性和热量特性的影响明显不同。据推断，这种影响可归因于双分子层膜中的酰基糖脂的位置不同。
• Permeability-controllable membranes. 7. Electrochemical responsive gate membranes of a multibilayer film containing a viologen group as redox sites
  作者：Yoshio Okahata、Genichiro Enna

  DOI：10.1021/j100326a058

  日期：1988.7
• Syntheses of Novel Galoctosyl Ligands for Liposomes and the Influence of the Spacer on Accumulation in the Rat Liver.
  作者：Atsushi SASAKI、Naokazu MURAHASHI、Harutami YAMADA、Anri MORIKAWA

  DOI：10.1248/bpb.18.740

  日期：——

  We modified the surface of liposomes with galactosyl ligands. At first we determined whether or not the galactosyl moiety was exposed on the liposomes. We then investigated the effect of the ligands on the hepatic accumulation of liposomes in rats. We introduced an oligoethylene glycol moiety as a spacer. Among the various ligands tested, those with a tri-or tetraethylene glycol moiety as a spacer caused the greatest accumulation of liposomes in the liver. Liposomes bearing ligands with a tri-or tetraethylene glycol moiety as a spacer, were aggregated by Ricinus communis agglutinin. On the other hand, those modified with ligands with a mono- or diethylene glycol spacer did not clearly agglutinate. These results show the importance of a spacer between the homing device and the ligand anchor.

  我们将半乳糖基配体修饰到脂质体表面。首先，我们确定半乳糖基团是否暴露在脂质体表面。然后，我们研究了这些配体对大鼠肝脏中脂质体积累的影响。我们引入了一个聚乙二醇基团作为间隔基。在测试的各种配体中，具有三或四聚乙二醇间隔基的配体导致脂质体在肝脏中积累最多。带有三或四聚乙二醇间隔基配体的脂质体被蓖麻凝集素聚集。另一方面，修饰有单或二聚乙二醇间隔基配体的脂质体没有明显聚集。这些结果显示了归巢装置与配体锚定基之间间隔基的重要性。