2-二苯基乙酰-1,3-茚酮-1-腙 | 5102-79-4

• 物质功能分类: 化学试剂 - 有机试剂 - 腙
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-二苯基乙酰-1,3-茚酮-1-腙
• 中文别名: 2-二苯乙酰基茚满-1,3-二酮-2-腙；2-二苯乙酰基-1,3-茚满二酮-1-腙
• 英文名称: 2-diphenylacetyl-1,3-indandione-1-hydrazone
• 英文别名: DAIH；2-(Diphenylacetyl)-1,3-indandione 1-hydrazone；2-(2,2-diphenylacetyl)-3-hydrazinylideneinden-1-one
• CAS: 5102-79-4
• 化学式: C₂₃H₁₈N₂O₂
• 分子量: 354.408
• InChiKey: QBGMRRUHCFHZLC-UHFFFAOYSA-N

物化性质

• 熔点：
  241-243 °C(lit.)
• 沸点：
  487.63°C (rough estimate)
• 密度：
  1.2033 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.086
• 拓扑面积：
  72.5
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险品标志：
  T,N
• 安全说明：
  S24/25
• 危险类别码：
  R25,R50/53
• WGK Germany：
  3
• 海关编码：
  2928000090

反应信息

• 作为反应物：
  描述：

  反式-2-癸烯醛 、 2-二苯基乙酰-1,3-茚酮-1-腙 在 盐酸 作用下， 以 水 、 乙腈 为溶剂， 反应 0.25h， 生成
  参考文献：
  名称：

  Activation of the Kelch-like ECH-Associated Protein 1 (Keap1)/NF-E2-Related Factor 2 (Nrf2) Pathway through Covalent Modification of the 2-Alkenal Group of Aliphatic Electrophiles in Coriandrum sativum L.

  摘要：

  Phytochemicals able to activate the transcription factor NF-E2-related factor 2 (Nrf2) were isolated from an extract of Coriandrum sativum L. (C. sativum) leaves by preparative octadecyl silica column chromatography. Ultraperformance liquid chromatography and liquid chromatography-tandem mass spectrometry analysis of the isolated components after derivatization with 2-diphenylacetyl-1,3-inandione-1-hydrazone and experiments with HepG2 cells revealed that (E)-2-alkenals with different carbon numbers play a role in Nrf2 activation in these cells. Such Nrf2 activation appears to be attributable to S-alkylation of Kelch-like ECH-associated protein 1 (Keap1), the negative regulator for Nrf2, as determined by a biotin-PEAC(5)-maleimide assay. Interestingly, (E)-2-butenal caused Keap1 modification and Nrf2 activation, whereas butanal did not. These results suggest that (E)-2-alkenals with an alpha,beta-unsaturated aldehyde moiety, which is a common substituent in phytochemicals isolated from C. sativum leaves, activate the Keap1/Nrf2 pathway associated with cellular protection.

  DOI：

  10.1021/jf5030592

文献信息

• Method to Simultaneously Determine the Sphingosine 1-Phosphate Breakdown Product (2<i>E</i>)-Hexadecenal and Its Fatty Acid Derivatives Using Isotope-Dilution HPLC–Electrospray Ionization–Quadrupole/Time-of-Flight Mass Spectrometry
  作者：Corinna Neuber、Fabian Schumacher、Erich Gulbins、Burkhard Kleuser

  DOI：10.1021/ac501677y

  日期：2014.9.16

  Sphingosine 1-phosphate (S1P), a bioactive lipid involved in various physiological processes, can be irreversibly degraded by the membrane-bound S1P lyase (S1PL) yielding (2E)-hexadecenal and phosphoethanolamine. It is discussed that (2E)-hexadecenal is further oxidized to (2E)-hexadecenoic acid by the long-chain fatty aldehyde dehydrogenase ALDH3A2 (also known as FALDH) prior to activation via coupling to coenzyme A (CoA). Inhibition or defects in these enzymes, S1PL or FALDH, result in severe immunological disorders or the Sjögren-Larsson syndrome, respectively. Hence, it is of enormous importance to simultaneously determine the S1P breakdown product (2E)-hexadecenal and its fatty acid metabolites in biological samples. However, no method is available so far. Here, we present a sensitive and selective isotope-dilution high performance liquid chromatography–electrospray ionization–quadrupole/time-of-flight mass spectrometry method for simultaneous quantification of (2E)-hexadecenal and its fatty acid metabolites following derivatization with 2-diphenylacetyl-1,3-indandione-1-hydrazone and 1-ethyl-3-(3-(dimethylamino)propyl)carbodiimide. Optimized conditions for sample derivatization, chromatographic separation, and MS/MS detection are presented as well as an extensive method validation. Finally, our method was successfully applied to biological samples. We found that (2E)-hexadecenal is almost quantitatively oxidized to (2E)-hexadecenoic acid, that is further activated as verified by cotreatment of HepG2 cell lysates with (2E)-hexadecenal and the acyl-CoA synthetase inhibitor triacsin C. Moreover, incubations of cell lysates with deuterated (2E)-hexadecenal revealed that no hexadecanoic acid is formed from the aldehyde. Thus, our method provides new insights into the sphingolipid metabolism and will be useful to investigate diseases known for abnormalities in long-chain fatty acid metabolism, e.g., the Sjögren-Larsson syndrome, in more detail.

  神经酰胺1-磷酸（S1P）是一种参与多种生理过程的生物活性脂质，能够被膜结合的S1P裂解酶（S1PL）不可逆降解，生成（2E）-己烯醛和磷酸乙醇胺。讨论指出，（2E）-己烯醛在通过与辅酶A（CoA）结合激活之前，会被长链脂肪醛脱氢酶ALDH3A2（也称为FALDH）进一步氧化为（2E）-己烯酸。如果这些酶中的任一酶，即S1PL或FALDH被抑制或出现缺陷，将导致严重的免疫疾病或干燥综合症，分别。因此，同时测定生物样本中S1P降解产物（2E）-己烯醛及其脂肪酸代谢物具有重要意义。然而，迄今为止尚无有效的方法。本文提出了一种灵敏且选择性强的同位素稀释高效液相色谱-电喷雾离子化-四极杆/飞行时间质谱法，用于在经过与2-二苯乙酰基-1,3-茚二酮-1-肼联用和1-乙基-3-(3-(二甲氨基)丙基)氨基脲后， simultaneously量化（2E）-己烯醛及其脂肪酸代谢物。我们呈现了样品衍生化、色谱分离和MS/MS检测的优化条件，以及广泛的方法验证。最终，我们的方法成功应用于生物样本。我们发现（2E）-己烯醛几乎完全被氧化为（2E）-己烯酸，并且在HepG2细胞裂解液中与（2E）-己烯醛和酰基-CoA合成酶抑制剂triacsin C共同处理的实验中得到了验证。此外，使用重标记（2E）-己烯醛处理细胞裂解液的实验揭示，未从醛形成己酸。因此，我们的方法为神经酰胺代谢提供了新的见解，并将在研究与长链脂肪酸代谢异常相关的疾病（例如干燥综合症）时发挥重要作用。