n-decanyl β-D-galactopyranoside | 6801-91-8

• 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: n-decanyl β-D-galactopyranoside
• 英文别名: decyl β-D-galactopyranoside；decyl-β-D-galactopyranoside；Decyl-β-D-galactopyranosid；Decyl beta-D-galactopyranoside；(2R,3R,4S,5R,6R)-2-decoxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 6801-91-8；29781-81-5；29781-82-6；58846-77-8；68225-08-1；142035-51-6；148347-28-8
• 化学式: C₁₆H₃₂O₆
• 分子量: 320.426
• InChiKey: JDRSMPFHFNXQRB-LYYZXLFJSA-N

物化性质

• 沸点：
  476.5±45.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  11
• 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

• 作为产物：
  描述：

  2,3,4,6-tetra-O-acetyl-β-D-galactopyranose 在 ammonium hydroxide 、 三氟化硼乙醚 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 3.2h， 生成 n-decanyl β-D-galactopyranoside
  参考文献：
  名称：

  The anomeric mixture of some O-galactolipid derivatives is more toxic against cancer cells than either anomer alone

  摘要：

  The anomeric mixture of a series of O-galactolipid derivatives is revealed to be more toxic against several cancer cell lines than their either single component with the pure alpha- or beta-configuration. This interesting phenomenon has been confirmed on pairs of synthesized O-galactosyl anomers bearing length-varied alkyl chains at the lipid end. Furthermore, the most potent mixture was determined inoffensive to a normal cell line tested. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.01.069

文献信息

• POLYMER STABILIZER
  申请人：KIMURA Yoshikazu

  公开号：US20100179253A1

  公开（公告）日：2010-07-15

  A polymer stabilizer comprising the following alkoxy compound: the alkoxy compound: a compound obtained by alkoxylating at least one hydroxyl group contained in a compound of the following formula (1) containing one formyl group or carbonyl group and (n− 1 ) hydroxyl groups in the molecule with an alkyl group having 1 to 12 carbon atoms: C n H 2n O n (1) (wherein, n represents an integer of 3 or more).

  一种聚合物稳定剂，包含以下烷氧基化合物：所述烷氧基化合物是通过将含有以下通式（1）中的一个甲酰基或羰基以及分子中（n-1）个羟基的化合物中的至少一个羟基进行烷氧基化而得到的化合物，其中烷基团含有1至12个碳原子：CnH2nOn（1）（其中，n代表3或以上的整数）。
• Antimicrobial and cytotoxic activity of (thio)alkyl hexopyranosides, nonionic glycolipid mimetics
  作者：Petr Džubák、Soňa Gurská、Kateřina Bogdanová、Daniela Uhríková、Nina Kanjaková、Sophie Combet、Tomáš Klunda、Milan Kolář、Marian Hajdúch、Monika Poláková

  DOI：10.1016/j.carres.2019.107905

  日期：2020.2

  as well as for antimicrobial potential on 12 bacterial and yeast strains. The most potent compounds were found to be tetradecyl and hexadecyl β-d-galactopyranosides (18, 19), which showed the best cytotoxicity and therapeutic index against CCRF-CEM cancer cell line. Similar cytotoxic activity showed hexadecyl α-d-mannopyranoside (5) but it also inhibited non-tumor cell lines. Because these two galactosides

  研究了一系列衍生自d-甘露糖，d-葡萄糖和d-半乳糖的，具有C10-C16糖苷配基的19种合成烷基和硫代烷基糖苷对7种人类癌症和2种非肿瘤细胞系的细胞毒活性以及抗菌潜力在12种细菌和酵母菌株上。发现最有效的化合物是十四烷基和十六烷基β-d-吡喃半乳糖苷（18、19），显示出对CCRF-CEM癌细胞系最佳的细胞毒性和治疗指数。相似的细胞毒活性显示十六烷基α-d-甘露吡喃糖苷（5），但它也抑制了非肿瘤细胞系。因为这两个半乳糖苷（18、19）对所有测试的细菌和酵母菌株均无活性，所以它们可能是真核细胞的靶标特异性靶标。另一方面，具有十四烷基（11）和十六烷基（12）糖苷配基的β-D-吡喃葡萄糖苷仅抑制革兰氏阳性菌粪肠球菌。从POPC模型膜上的SAXS实验推导，所研究的苷在高浓度下诱导脂质双层厚度和侧向相分离的变化。通常，葡糖苷和半乳糖苷表现出更具体的性质。具有较长糖苷配基的化合物显示出高细胞毒性，
• Sweet surfactants: packing parameter-invariant amphiphiles as emulsifiers and capping agents for morphology control of inorganic particles
  作者：Michael Voggel、Rebecca M. Meinusch、Vanessa Siewert、Marius Kunkel、Valentin Wittmann、Sebastian Polarz

  DOI：10.1039/c8sm01091a

  日期：——

  Exploration of isomer effects on amphiphile properties (e.g.emulsification and as nanoparticle growth modifiers) using a library of glycoside-based surfactants.

  对异构体对两性分子性质（如乳化和作为纳米粒子生长调节剂）的影响进行探索，使用基于糖苷的表面活性剂库。
• A Facile Transgalactosylation catalyzed by a Lipid-Coated β-<i>D</i>-Galactosidase in the Water-Organic Two Phases
  作者：Toshiaki Mori、Sanae Fujita、Yoshio Okahata

  DOI：10.1246/cl.1997.73

  日期：1997.1

  A lipid-coated β-D-galactosidase could act as an efficient catalyst for transgalactosylation in the water-organic two phases: both the hydrophobic lipid-coated enzyme and alcohols were solubilized in isopropyl ether and mixed with an aqueous solution of lactose (a galactosyl donor). When a native β-D-galactosidase was employed for the same reaction, neither the transgalactosylation nor the hydrolysis reaction proceeded due to the deactivation of the enzyme at the interface.

  一种脂质包被的β-D-半乳糖苷酶可以作为水-有机两相中转半乳糖基化的高效催化剂：脂肪性脂质包被的酶和醇在异丙醚中被溶解，并与乳糖（半乳糖基供体）的水溶液混合。当使用天然的β-D-半乳糖苷酶进行相同反应时，由于酶在界面处失活，既未发生转半乳糖基化反应，也未发生水解反应。
• Synthesis and Properties of Alkyl β-d-Galactopyranoside
  作者：Guoyong Chen、Zhencao Li、Langqiu Chen、Shanwei Ji、Wangzhen Shen

  DOI：10.1007/s11743-016-1865-0

  日期：2016.11

  decreases with increasing alkyl chain length. Decyl β‐d‐galactopyranoside was insoluble in water, but soluble in ethanol. Dissolution of alkyl β‐d‐galactopyranoside in water is an endothermic process with dissolution enthalpies greater than zero. Nonyl β‐d‐galactopyranoside had an excellent emulsifying property, better foaming ability and the best foam stability. The CMC values of alkyl β‐d‐galactopyranosides

  用三氯乙酰亚氨酸酯方法，以d-半乳糖和不同链长的醇为原料，制备了一系列烷基β - d-吡喃半乳糖苷。研究了它们的溶解度，表面张力，乳化，发泡，润湿性，热致液晶性能和热稳定性。烷基β - d-吡喃半乳糖苷可溶于水和乙醇，且溶解度随烷基链长度的增加而降低。癸基β - d-吡喃半乳糖苷不溶于水，但可溶于乙醇。烷基β - d的溶解水中的吡喃半乳糖苷是一个吸热过程，其溶解焓大于零。壬基β - d-吡喃半乳糖苷具有优异的乳化性能，更好的发泡能力和最佳的泡沫稳定性。烷基β - d-吡喃半乳糖苷的CMC值随烷基链长的增加而降低。烷基β - d-吡喃半乳糖苷在高达270°C的温度下具有热稳定性。烷基β - d-半乳糖吡喃糖苷显示出热致液晶近晶A型相的独特光学结构。癸基β - d-吡喃半乳糖苷显示出最强的润湿性。