[1-11C]octanoic acid

• 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: [1-11C]octanoic acid
• 英文别名: (111C)octanoic acid
• 化学式: C₈H₁₆O₂
• 分子量: 143.203
• InChiKey: WWZKQHOCKIZLMA-COJKEBBMSA-N

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

• 作为产物：
  描述：

  HEPTYLMAGNESIUM BROMIDE 、 [11C]二氧化碳 以 四氢呋喃 为溶剂， 生成 [1-11C]octanoic acid
  参考文献：
  名称：

  Critical evaluation of the chemical standardization procedure for measuring gastric emptying of solids

  摘要：

  本研究的目的是评估添加辛酸盐的蛋黄烘烤过程，以测量固体的胃排空速率。[1-11C]辛酸盐是通过将[11C]CO2与七碳镁溴化物在四氢呋喃（THF）中反应生成的，随后通过HPLC进行纯化。衰变校正后的放射化学产率范围为24%至38%（5.9–9.8 GBq EOS，合成时间：25分钟；特定放射活度约为90 GBq μmol−1）。为了检查在蛋黄烘烤过程中[1-11C]辛酸盐的蒸发情况，分别添加了[1-11C]辛酸盐或氢氧化钾[1-11C]辛酸盐。重要的一部分酸在蒸发过程中消失，而氢氧化钾[1-11C]辛酸盐的蒸发率则低于10%。结论：氢氧化钾（1-13C）辛酸盐在研究胃肠现象时比（1-13C）辛酸盐更为合适。版权所有 © 2002 John Wiley & Sons, Ltd.

  DOI：

  10.1002/jlcr.609

文献信息

• [1-11C]Octanoate as a PET Tracer for Studying Ischemic Stroke. Evaluation in a Canine Model of Thromboembolic Stroke with Positron Emission Tomography.
  作者：Yuji KUGE、Hidefumi KAWASHIMA、Kazuo MINEMATSU、Yasuhiro HASEGAWA、Takenori YAMAGUCHI、Yoshihiro MIYAKE、Tadatoshi HASHIMOTO、Mitsuaki IMANISHI、Mie SHIOMI、Nagara TAMAKI、Naoto HASHIMOTO

  DOI：10.1248/bpb.23.984

  日期：——

  Octanoate is taken up by the brain and converted in astrocytes to glutamine through the TCA cycle after β-oxidation. Consequently, [111C]octanoate might serve as a useful positron emission tomography (PET) probe for studying cerebral oxidative metabolism and/or astroglial functions. The present study attempted to evaluate the utility of using [111C]octanoate as a PET tracer for imaging and evaluating the pathopysiology of ischemic stroke. We used a canine model of thromboembolic stroke. Five male beagle dogs were implanted with an indwelling catheter in the left internal carotid artery. A single autologous blood clot was injected into the left internal carotid artery through the catheter. The brain distribution of [111C]octanoate and cerebral blood flow (CBF) were determined 24 h after insult using a high resolution PET scanner. Post mortem brain regions unstained with 2, 3, 5-triphenyltetrazolium chloride (TTC) were defined as infarcts. In the region of an infarct, accumulation of [111C]octanoate decreased concurrently with CBF reduction. In contrast, normal accumulation of [111C]octanoate was observed in ischemic but vital regions, suggesting that an increased accumulation of [111C]octanoate relative to CBF takes place in these regions. In conclusion, [111C]octanoate accumulated in ischemic but vital retions, indicating that [111C]octanoate is potentially useful PET tracer for imaging and evaluating the pathophysiology of ischemic stroke.

  八烷酸在β氧化后被脑部吸收，并在星形胶质细胞中通过三羧酸循环转化为谷氨酰胺。因此，[111C]八烷酸可能作为一种有用的正电子发射断层扫描（PET）探针，用于研究大脑的氧化代谢和/或星胶质功能。本研究旨在评估使用[111C]八烷酸作为PET示踪剂在成像和评估缺血性中风的病理生理学中的实用性。我们采用了一种犬模型的血栓栓塞中风。将五只雄性比格犬的左侧颈内动脉植入了一个留置导管。通过导管向左侧颈内动脉注入一个自体血栓。在受损后24小时，使用高分辨率PET扫描仪确定[111C]八烷酸的脑部分布和大脑血流（CBF）。用2, 3, 5-三苯基氮杂氛丙酮（TTC）染色后未着色的脑区被定义为梗死区。在梗死区，[111C]八烷酸的积累与CBF减少同时发生减少。相反，在缺血但仍然存活的区域观察到了正常的[111C]八烷酸积累，提示这些区域的[111C]八烷酸相对于CBF有增加的积累。总之，[111C]八烷酸在缺血但存活的区域中积累，这表明[111C]八烷酸可能是用于成像和评估缺血性中风病理生理学的有用PET示踪剂。
• Kinetic Study on the Reaction of Heptylmagnesium Bromide with Carbon Dioxide Using Non-Carrier-Added C-11 Labeled Carbon Dioxide
  作者：Kazuyoshi Yajima、Hidefumi Kawashima、Naoto Hashimoto、Yoshihiro Miyake

  DOI：10.1021/jp961023w

  日期：1996.1.1

  We studied the chemical kinetics of the Grignard reaction between heptylmagnesium bromide and carbon dioxide with a new experimental method utilizing positron emitter C-11 labeled CO2; A series of experiments was carried out in the presence of a large excess of heptylmagnesium bromide (C7H15MgBr = ca, 1.0 x 10(-4) mol) relative to carbon dioxide (CO2 = ca. 1.2 x 10(-8) mol). An empirical scheme was assumed based on the results obtained in experiments at the reaction temperature of 20 degrees C. Differential equations were determined by the scheme. It was possible to calculate rate constant values at each temperature of the reaction (at 10, 20, and 30 degrees C) by fitting the equations to experimental measurements. We obtained the value 1.76 x 10(4) J/mol as the activation energy of the main reaction between C7H15MgBr and CO2 from the Arrhenius plot (r(2) = 0.9986) of the rate constants. The reaction simulated with the equations and the activation energy value were in good agreement with the ones obtained experimentally. The obtained value for the activation energy of the main reaction would be applicable to the more common type of Grignard carboxylation with a large excess of CO2.
• Critical evaluation of the chemical standardization procedure for measuring gastric emptying of solids
  作者：P. Goethals、A. Volkaert、B. Van Vlem、R. Vanholder

  DOI：10.1002/jlcr.609

  日期：2002.11

  The purpose of this study was to evaluate the baking process of yolk spiked with octanoate to measure gastric emptying rate of solids. [1-11C]octanoate was produced by the reaction of [11C]CO2 with heptyl magnesium bromide in tetrahydrofuran (THF), followed by purification with HPLC. The decay corrected radiochemical yield ranged from 24 to 38% (5.9–9.8 GBq EOS, synthesis time: 25 min; specific radioactivity ∼90 GBq μmol−1). To check the evaporation of [1-11C]octanoate during the baking process of yolk, [1-11C]octanoate or potassium [1-11C]octanoate, respectively, was added. An important fraction of the acid evaporated while for the potassium [1-11C]octanoate <10% disappeared. Conclusion: potassium (1-13C)octanoate is a better tracer than (1-13C) octanoate to study gastroenterological phenomena. Copyright © 2002 John Wiley & Sons, Ltd.

  本研究的目的是评估添加辛酸盐的蛋黄烘烤过程，以测量固体的胃排空速率。[1-11C]辛酸盐是通过将[11C]CO2与七碳镁溴化物在四氢呋喃（THF）中反应生成的，随后通过HPLC进行纯化。衰变校正后的放射化学产率范围为24%至38%（5.9–9.8 GBq EOS，合成时间：25分钟；特定放射活度约为90 GBq μmol−1）。为了检查在蛋黄烘烤过程中[1-11C]辛酸盐的蒸发情况，分别添加了[1-11C]辛酸盐或氢氧化钾[1-11C]辛酸盐。重要的一部分酸在蒸发过程中消失，而氢氧化钾[1-11C]辛酸盐的蒸发率则低于10%。结论：氢氧化钾（1-13C）辛酸盐在研究胃肠现象时比（1-13C）辛酸盐更为合适。版权所有 © 2002 John Wiley & Sons, Ltd.