丙烯酰胺-13C3 | 287399-26-2

• 物质功能分类: 化学试剂 - 有机试剂 - 酰胺
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 丙烯酰胺-13C3
• 英文名称: [13C3]acrylamide
• 英文别名: (1,2,3-13C)arylamide；Acrylamide-13C3；(1,2,3-13C3)prop-2-enamide
• CAS: 287399-26-2
• 化学式: C₃H₅NO
• 分子量: 74.0458
• InChiKey: HRPVXLWXLXDGHG-VMIGTVKRSA-N

物化性质

• 熔点：
  82-86 °C (lit.)
• 沸点：
  125 °C/25 mmHg (lit.)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  5
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.1
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 危险品标志：
  T
• 安全说明：
  S45,S53
• 危险类别码：
  R45,R46,R20/21,R25,R36/38,R43,R48/23/24/25,R62
• WGK Germany：
  3

制备方法与用途

概述

丙烯酰胺（Acrylamide），化学分子式为CH₂CHCONH₂，是一种易溶于水的无色透明片状结晶。作为一种常见的有机合成原料，在工业上得到了广泛的应用。

国际癌症研究中心（IARC）将丙烯酰胺列为IIA类致癌物；世界卫生组织（WHO）认为“致癌风险性超过10^-5的指导值为0.5 µg/L”。自2002年瑞典科学家首次发现淀粉类食品在高温加工过程中会产生大量的丙烯酰胺后，这一问题引起了全球广泛关注。丙烯酰胺-13C₃ 可用于测定丙烯酰胺含量。

应用

丙烯酰胺-13C₃又称为13C₃-丙烯酰胺，可用于准确测定丙烯酰胺的含量。

反应信息

• 作为反应物：
  描述：

  N,O-双(三甲基硅烷基)三氟乙酰胺 、 丙烯酰胺-13C3 以 乙腈 为溶剂， 反应 1.0h， 生成 N,O-bis(trimethylsilyl)-[13C3]-acrylamide
  参考文献：
  名称：

  Silylation of Acrylamide for Analysis by Solid-Phase Microextraction/Gas Chromatography/Ion-Trap Mass Spectrometry

  摘要：

  A method for quantitative analysis of acrylamide has been developed for use with headspace solid-phase microextraction (SPME). In the method, acrylamide undergoes silylation with N,O-bis(trimethylsilyl)trifluoroacetamide (BSTFA) to form the volatile N,O-bis(trimethylsilyl)acrylamide (BTMSA). Once formed, BTMSA is readily extracted from the headspace over the silylation reaction using a 100,mum poly(dimethylsiloxane) SPME fiber. A series of experiments was undertaken to optimize the amount of BSTFA, the silylation reaction temperature, the silylation reaction duration, and SPME sampling duration to maximize the analytical sensitivity for BTMSA. Acrylamide levels were quantified relative to a [C-13(3)]-acrylamide internal standard using gas chromatography/ion-trap mass spectrometry (GC/MS) in the single ion monitoring mode. An analytical working curve was constructed and found to be linear over the 4 to 6700 ppb acrylamide range investigated with a limit of detection of 0.9 ppb. The native acrylamide levels of three commercial cereals were measured using the optimized analytical method. Quantitative standard additions of acrylamide to the cereal matrixes demonstrated complete recovery of the spiked acrylamide.

  DOI：

  10.1021/jf049759a

文献信息

• Synthesis, characterization and analysis of the acrylamide- and glycidamide-glutathione conjugates
  作者：Yu-Syuan Luo、Tai-Ying Long、Li-Ching Shen、Shou-Ling Huang、Su-Yin Chiang、Kuen-Yuh Wu

  DOI：10.1016/j.cbi.2015.05.002

  日期：2015.7

  Acrylamide (AA) is reported present in high-temperature-processed food and classified as a possible human carcinogen. In vivo metabolic activation of AA by CYP 2E1 to glycidamide (GA) may play an important role on AA carcinogenicity. AA and GA can be detoxified by glutathione-S-transferase to form AA and isomeric GA glutathione conjugates (M-, GA2- and GA3-GSH, respectively), which can be further metabolized to mercapturic acids (MAs). Although many studies analyzed MAs in urine of rodents and humans, few studies have characterized and analyzed the GSH conjugates. The objectives of this study were to synthesize, purify, and characterize AA-GSH, GA2-GSH, GA3-GSH, (C-13(3))-AA-GSH, (C-13(3))-GA2-GSH, and (C-13(3))-GA3-GSH to develop an isotope-dilution liquid chromatography tandem mass spectrometry (LC-MS/MS) method to analyze AA- and GA-GSHs in blood of rats treated with AA. After purification and characterization of these conjugates, the LC-MS/MS method was developed and validated. This method reveals a limit of detection (S/N= 3) at 0.017 and a limit of quantitation (S/N = 10) at 0.05 ng/mL of serum for AA-GSH, 0.075 and 0.25 ng/mL for GA2-GSH, and 0.15 and 0.5 ng/mL for GA3-GSH. Analyzed with this method, AA-GSH, GA2-GSH and GA3-GSH were 1651.1 +/- 374.5, 18.4 +/- 6.3 and 75.3 +/- 31.3 ng/mL in blood of male rats at 2 h after treatment with 5 mg/kg bw of AA by ip injection. These results showed that the LC-MS/MS method was successfully developed to analyze AA-GSH, GA2-GSH and GA3-GSH with satisfying sensitivity of AA and GA which were conjugated by glutathione in vivo. (C) 2015 Elsevier Ireland Ltd. All rights reserved.
• Silylation of Acrylamide for Analysis by Solid-Phase Microextraction/Gas Chromatography/Ion-Trap Mass Spectrometry
  作者：Anthony F. Lagalante、Matthew A. Felter

  DOI：10.1021/jf049759a

  日期：2004.6.1

  A method for quantitative analysis of acrylamide has been developed for use with headspace solid-phase microextraction (SPME). In the method, acrylamide undergoes silylation with N,O-bis(trimethylsilyl)trifluoroacetamide (BSTFA) to form the volatile N,O-bis(trimethylsilyl)acrylamide (BTMSA). Once formed, BTMSA is readily extracted from the headspace over the silylation reaction using a 100,mum poly(dimethylsiloxane) SPME fiber. A series of experiments was undertaken to optimize the amount of BSTFA, the silylation reaction temperature, the silylation reaction duration, and SPME sampling duration to maximize the analytical sensitivity for BTMSA. Acrylamide levels were quantified relative to a [C-13(3)]-acrylamide internal standard using gas chromatography/ion-trap mass spectrometry (GC/MS) in the single ion monitoring mode. An analytical working curve was constructed and found to be linear over the 4 to 6700 ppb acrylamide range investigated with a limit of detection of 0.9 ppb. The native acrylamide levels of three commercial cereals were measured using the optimized analytical method. Quantitative standard additions of acrylamide to the cereal matrixes demonstrated complete recovery of the spiked acrylamide.