1,2-bis<(3RS,7R,11R)-dihydrophthyl>glycerol | 200715-68-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 1,2-bis<(3RS,7R,11R)-dihydrophthyl>glycerol
• 英文别名: (RS)-2,3-bis-[[(3RS,7R,11R)-3,7,11,15-tetramethylhexadecyl]oxy]propanol；2,3-bis[(7R,11R)-3,7,11,15-tetramethylhexadecoxy]propan-1-ol
• CAS: 200715-68-0
• 化学式: C₄₃H₈₈O₃
• 分子量: 653.17
• InChiKey: ISDBCJSGCHUHFI-RZYBXOIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.2
• 重原子数：
  46
• 可旋转键数：
  34
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,2-bis<(3RS,7R,11R)-dihydrophthyl>glycerol 在 4-二甲氨基吡啶 、 N-碘代丁二酰亚胺 、 三乙基硅基三氟甲磺酸酯 、 sodium methylate 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 为溶剂， 反应 74.0h， 生成
  参考文献：
  名称：

  Synthesis and liquid-crystalline properties of novel archaeal diether-type glycolipids possessing one or two furanosyl units

  摘要：

  Archaeal diether-type analogues possessing one or two furanosyl polar head groups and methyl branched aliphatic moieties were synthesized by glycosylation of glycerolipids with pent-4-enyl 2,3,5,6-tetra-O-acetyl-D-glycofuranoside as the donors. The products were shown to form thermotropic and lyotropic liquid crystalline mesophases, tubules and vesicles. The self-assembling properties of the compounds prepared were found to be similar to those of naturally occurring materials, in that they exhibited columnar thermotropic mesophases and hexagonal lyotropic phases. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00291-2
• 作为产物：
  描述：

  二苄醚 在 Pd-C 作用下， 以 四氢呋喃 为溶剂， 生成 1,2-bis<(3RS,7R,11R)-dihydrophthyl>glycerol
  参考文献：
  名称：

  Glycerol ether phosphatides

  摘要：

  通式为##STR1##的化合物，其中两个残基R.sup.1、R.sup.2和R.sup.3代表至少有8个C原子的直链C.sub.10-30烷基残基，其中至少一个残基被至少2个C.sub.1-3烷基残基取代，这两个残基中的C原子总数大于20；第三个残基是一个残基--P(O)(O.sup.-)OR.sup.4，其中R.sup.4代表一个取代有季铵基团的低烷基或C.sub.5-7环烷基残基，或者一个含有二(低烷基)取代氮原子的C.sub.5-7环烷基残基，这些化合物可用于制备胶体溶液系统。通式I的化合物可以从甘油衍生物开始制备，详细描述在说明书中。

  公开号：

  US04694084A1

文献信息

• Archaebacterial Lipids: Stable Anionic Membranes from 1,2-Bis(dihydrophytyl)glycero-3-phosphate
  作者：Kiyoshi Yamauchi、Katsuya Togawa、Masayoshi Kinoshita

  DOI：10.1246/bcsj.66.2097

  日期：1993.7

  1,2-Bis(dihydrophytyl)glycero-3-phosphate (DPhyPA) was synthesized as an analog of archaebacterial lipids. Upon sonicating in amine-containing buffers like 0.05 M Tris–HCl (pH 7.8), the lipid gave rise to the stable liposomal assemblies, which could store 5(6)-carboxyfluorescein at high temperature as high as 70 °C in the interior. The assembly also had a large negative zeta-potential and showed an absence of gel-to-liquid crystalline phase transition from −20 to 80 °C. A Langmuir monolayer at an air/water interface suggested that the maximum molecular area of the lipid was 0.9—1.0 nm2. These properties were compared with the assemblies prepared from conventional 1,2-dipalmitoyl-sn-glycero-3-phosphate and 1,2-dipalmitoyl-sn-glycero-3-phosphocholine.

  1,2-双（二氢phytyl）甘油-3-磷酸酯（DPhyPA）是作为古细菌脂质的类似物合成的。在 0.05 M Tris-HCl（pH 7.8）等含胺缓冲液中超声处理后，这种脂质产生了稳定的脂质体组装体，其内部可在高达 70 °C 的高温下储存 5(6)- 羧基荧光素。这种组装体还具有较大的负Zeta电位，并且在-20至80 °C期间没有出现凝胶到液态结晶的相变。空气/水界面上的朗缪尔单层表明，脂质的最大分子面积为 0.9-1.0 nm2。将这些特性与传统的 1,2-二棕榈酰-sn-甘油-3-磷酸和 1,2-二棕榈酰-sn-甘油-3-磷酸胆碱制备的组合物进行了比较。
• STEWART, L. C.;KATES, M., CHEM. AND PHYS. LIPIDS, 50,(1989) N, C. 23-42
  作者：STEWART, L. C.、KATES, M.

  DOI：——

  日期：——
• US4694084A
  申请人：——

  公开号：US4694084A

  公开（公告）日：1987-09-15
• Synthesis and liquid-crystalline properties of novel archaeal diether-type glycolipids possessing one or two furanosyl units
  作者：Rachel Auzély-Velty、Thierry Benvegnu、Grahame Mackenzie、Julie A Haley、John W Goodby、Daniel Plusquellec

  DOI：10.1016/s0008-6215(98)00291-2

  日期：1998.12

  Archaeal diether-type analogues possessing one or two furanosyl polar head groups and methyl branched aliphatic moieties were synthesized by glycosylation of glycerolipids with pent-4-enyl 2,3,5,6-tetra-O-acetyl-D-glycofuranoside as the donors. The products were shown to form thermotropic and lyotropic liquid crystalline mesophases, tubules and vesicles. The self-assembling properties of the compounds prepared were found to be similar to those of naturally occurring materials, in that they exhibited columnar thermotropic mesophases and hexagonal lyotropic phases. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Glycerol ether phosphatides
  申请人：Hoffmann-La Roche Inc.

  公开号：US04694084A1

  公开（公告）日：1987-09-15

  Compounds of the general formula ##STR1## wherein two of the residues R.sup.1, R.sup.2 and R.sup.3 represent C.sub.10-30 -alkyl residues with at least 8 C-atoms in a straight chain, at least one of these residues being substituted by at least 2 C.sub.1-3 -alkyl residues and the sum of the C-atoms in the two residues being greater than 20; and the third residue is a residue --P(O)(O.sup.-)OR.sup.4 in which R.sup.4 represents a lower-alkyl or C.sub.5-7 -cycloalkyl residue which is substituted by a quaternary ammonium group or a C.sub.5-7 -cycloalkyl residue which contains a di-(lower-alkyl)-substituted nitrogen atom, are useful for the manufacture of colloidal solution systems. The compounds of formula I can be prepared starting from glycerol derivatives as described in more detail in the specification.

  通式为##STR1##的化合物，其中两个残基R.sup.1、R.sup.2和R.sup.3代表至少有8个C原子的直链C.sub.10-30烷基残基，其中至少一个残基被至少2个C.sub.1-3烷基残基取代，这两个残基中的C原子总数大于20；第三个残基是一个残基--P(O)(O.sup.-)OR.sup.4，其中R.sup.4代表一个取代有季铵基团的低烷基或C.sub.5-7环烷基残基，或者一个含有二(低烷基)取代氮原子的C.sub.5-7环烷基残基，这些化合物可用于制备胶体溶液系统。通式I的化合物可以从甘油衍生物开始制备，详细描述在说明书中。