<1-14C>octanoic acid | 3106-28-3

• 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: <1-14C>octanoic acid
• 英文别名: [1-14C]octanoic acid；n-Octansaeure；(1-14C)-Caprylsaeure；[1-¹⁴C]Octansaeure；(114C)octanoic acid
• CAS: 3106-28-3
• 化学式: C₈H₁₆O₂
• 分子量: 146.203
• InChiKey: WWZKQHOCKIZLMA-PPJXEINESA-N

物化性质

• 密度：
  0.929±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  10
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  <1-14C>octanoic acid 、 3-溴丙烯 以71%的产率得到C₁₀⁽¹⁴⁾CH₂₂O₂
  参考文献：
  名称：

  Solid-phase synthesis of isotope-labeled 2-propyloctanoic acid, a therapeutic agent for stroke and Alzheimer's disease

  摘要：

  DOI：

  10.1002/jlcr.1221
• 作为产物：
  描述：

  二氧化碳-14C 、 HEPTYLMAGNESIUM BROMIDE 在 乙醚 作用下， 生成 <1-14C>octanoic acid
  参考文献：
  名称：

  Geyer; Matthews; Stare, Journal of Biological Chemistry, 1949, vol. 180, p. 1038

  摘要：

  DOI：

文献信息

• Synthesis of fluorescent and radioactive analogues of two lactosylceramides and glucosylceramide containing β-thioglycosidic bonds that are resistant to enzymatic degradation
  作者：Bernd Albrecht、Ute Pütz、Günter Schwarzmann

  DOI：10.1016/0008-6215(95)00189-z

  日期：1995.10

  Condensation of 2-S-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)-2-thiopseudourea hydrobromide with 2,3,6-tri-O-benzoyl-4-O-trifluoromethylsulfonyl-beta-D-galactopyranosy-(1-->1)-(2S,3R,4E)-3-O-benzoyl-2-dichloroacetamido-4-octadecan afforded S-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)-(1-->4)-2,3,6-tri-O-benzoyl-4-thio-beta-D-glucopyranosyl-(1-->1)-(2S, 3R,4E)-3-O-benzoyl-2-dichloroacetamido-4 in good yield. Removal of the protecting groups, followed by selective N-acylation of the sphingosine amino group with either a fluorescent or a radioactive fatty acid, gave labeled lactosylceramide analogues in good yield. Since these products contained a beta-thioglycosidic bond between the two sugar moieties, they were totally resistant to the action of acid lysosomal glycosidases. Likewise, condensation of 2-S(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosy hydrobromide and 2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl-(1-->4)-2,3,6-tri-O- acetyl-1-S-acetyl-1-thio-beta-D-glucopyranose with (2R,3R,4E)-3-O-benzoyl-2-dichloroacetamido-1-iodo-4-octadecen-3-ol in methanolic sodium acetate afforded the corresponding beta-thioglycosides 14 and 16, respectively, in good yield. These beta-thioglycosides were converted into glucosylceramide and lactosylceramide analogues following removal of the protecting groups and by subsequent selective N-acylation using either a fluorescent or radioactive fatty acid N-succinimidyl ester. Whereas the glucosylthioceramides thus obtained proved to be completely undegradable by lysosomal glucocerebrosidase, the lactosylceramides containing the beta-thioglycosidic bond between the lactose and the ceramide residues could be degraded by lysosomal GM1-beta-galactosidase to give the corresponding glucosylthioceramides. These compounds did not yield to any further enzymatic degradation.
• Geyer; Matthews; Stare, Journal of Biological Chemistry, 1949, vol. 180, p. 1038
  作者：Geyer、Matthews、Stare

  DOI：——

  日期：——
• Solid-phase synthesis of isotope-labeled 2-propyloctanoic acid, a therapeutic agent for stroke and Alzheimer's disease
  作者：Jonathan Z. Ho、Cheng Tang、Matthew P. Braun

  DOI：10.1002/jlcr.1221

  日期：2007.4