12-formatododecanoic acid | 18342-56-8

• 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: 12-formatododecanoic acid
• 英文别名: 12-Formyloxydodecanoic acid
• CAS: 18342-56-8
• 化学式: C₁₃H₂₄O₄
• 分子量: 244.331
• InChiKey: YGAAXQSSFUQNIG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  12-formatododecanoic acid 在 sodium hydroxide 、 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 96.17h， 生成 bis(N-dodecylaza-18-crown-6) ether
  参考文献：
  名称：

  来自新冠醚基博拉两亲物家族的超薄单层脂质膜

  摘要：

  已经制备、表征了 12 种新型 α,Ω-双（N-氮杂冠醚）化合物，并将其转化为以前未知类型的 niosome。四种是具有以下间隔链的双(15-crown-5)衍生物：(CH 2 ) 12 (1)、(CH 2 ) 16 (2)、CO(CH 2 ) 20 CO (3)和(CH 2 ) 22 (4)

  DOI：

  10.1021/ja00058a014
• 作为产物：
  描述：

  甲酸 、 12-羟基十二酸 反应 4.0h， 以91%的产率得到12-formatododecanoic acid
  参考文献：
  名称：

  来自新冠醚基博拉两亲物家族的超薄单层脂质膜

  摘要：

  已经制备、表征了 12 种新型 α,Ω-双（N-氮杂冠醚）化合物，并将其转化为以前未知类型的 niosome。四种是具有以下间隔链的双(15-crown-5)衍生物：(CH 2 ) 12 (1)、(CH 2 ) 16 (2)、CO(CH 2 ) 20 CO (3)和(CH 2 ) 22 (4)

  DOI：

  10.1021/ja00058a014

文献信息

• Predicting Drug-Membrane Interactions by HPLC: Structural Requirements of Chromatographic Surfaces
  作者：Hanlan. Liu、Shaowei. Ong、Louis. Glunz、Charles. Pidgeon

  DOI：10.1021/ac00115a026

  日期：1995.10.1

  Drug-membrane interactions have recently been studied by immobilized artificial membrane (IAM) chromatography (Pidgeon, C,; et al, J. Med. Chem. 1995, 38, 590-595, Ong, S.; et al, Anal. Chem. 1995, 67, 755-762), and the molecular recognition properties of IAM surfaces toward drug binding/partitioning appear to be remarkably close to the molecular recognition properties of fluid membranes. The structural requirements of chromatography surfaces to emulate biological partitioning are unknown. To begin to elucidate the surface structural requirements needed to predict drug partitioning into membranes, three bonded phases were prepared, The chromatography bonded phases were prepared by immobilizing (i) a single-chain analog containing the phosphocholine (PC) headgroup (IAM.PC.DD), (ii) a long-chain alcohol containing polar OH groups protruding from the surface (12-OH-silica), and (iii) a long-chain fatty acid containing OCH3 groups protruding from the surface (12-MO-silica). The 12-OH-silica surface can be considered as an immobilized ''octanol'' phase with OH groups protruding from the surface and is therefore a solid phase model of octanol/water partitioning systems, As expected, improved capability of predicting solute-membrane interactions as found for the chromatographic surface containing the PC polar head-group because the PC headgroup is also found in natural cell membranes, For instance, the IAM.PC.DD column predicted drug partitioning into dimyristoylphosphatidylcholine liposomes (r = 0.864) better than 12-OH-silica (r = 0.812), and 12-MO-silica (r = 0.817), IAM. PC.DD columns also predicted intestinal drug absorption (r = 0.788) better than 12-OH-silica (r = 0.590) and 12-MO-silica (r = 0.681); reversed phase octadecylsilica (ODS) columns could not predict intestinal absorption (r = 0.10). Collectively, these results suggest that chromatographic surfaces containing interfacial polar groups, i.e., PC, OH, and OCH3, model drug-membrane interactions, but surfaces lacking interfacial polar functional groups (e.g., ODS surface) are poor models, Most interestingly, drug partitioning into octanol/water systems does not correlate with drug binding to the immobilized octanol phase, However, drug partitioning into immobilized octanol correlates with drug partitioning into liposomes (r = 0.812).