[U-RING-13C6]-4-羟基苯甲醛 | 201595-48-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: [U-RING-13C6]-4-羟基苯甲醛
• 英文名称: 4-hydroxyben[13C₆-ring]aldehyde
• 英文别名: 4-hydroxy-[ring-U-13C6]benzaldehyde；[U-ring-13C6]-4-hydroxybenzaldehyde；4-hydroxy[ring-(13)C6]benzaldehyde；4-Hydroxy-benzaldehyde-1,2,3,4,5,6-13C6；4-hydroxy(1,2,3,4,5,6-13C6)cyclohexa-1,3,5-triene-1-carbaldehyde
• CAS: 201595-48-4
• 化学式: C₇H₆O₂
• 分子量: 128.057
• InChiKey: RGHHSNMVTDWUBI-ZFJHNFROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  [U-RING-13C6]-4-羟基苯甲醛 在 lithium aluminium deuteride 、 camphor-10-sulfonic acid 作用下， 以 二氯甲烷 为溶剂， 生成 4-[9,9-(2)H2, ring-(13)C6]coumaryl alcohol ethoxyethyl ether
  参考文献：
  名称：

  Suzuki; Umezawa; Shimada, Journal of the Chemical Society. Perkin Transactions 1 (2001), 2001, # 24, p. 3252 - 3257

  摘要：

  DOI：

文献信息

• Synthesis of3H,14C and13C6 labelled Sch 58235
  作者：D. Hesk、G. Bignan、J. Lee、J. Yang、K. Voronin、C. Magatti、P. McNamara、D. Koharski、S. Hendershot、S. Saluja、S. Wang

  DOI：10.1002/jlcr.539

  日期：2002.2

  3H-Sch 58235 was prepared at a specific activity of 29.1 Ci/mmol by Ir(COD)(Cy3P)PyPF6 catalysed exchange with tritium gas. 14C-Sch 58235 was prepared in three steps from p-hydroxy[ring-U-14C]benzaldehyde with an overall radiochemical yield of 21%. 13C6-Sch 58235 was similarly prepared in three steps from p-hydroxy[ring-U-13C6]benzaldehyde in an overall yield of 41%. Copyright © 2002 John Wiley & Sons, Ltd.

  3H-Sch 58235 是通过使用Ir(COD)(Cy3P)PyPF6催化剂与氚气进行交换反应制备的，其特定活性为29.1 Ci/mmol。14C-Sch 58235 是从p-羟基[环-U-14C]苯甲醛经过三步反应制备的，总体放射化学产率为21%。13C6-Sch 58235 也是从p-羟基[环-U-13C6]苯甲醛经过三步反应类似制备的，总体产率为41%。版权所有 © 2002 John Wiley & Sons, Ltd.
• Synthesis of JTT-501 and its metabolite JTP-20604 labelled with13C
  作者：A. Pignatti、D. Giribone、C. Felicini、E. Fontana

  DOI：10.1002/jlcr.700

  日期：2003.6

  JTT-501 specifically labelled with 13C was obtained via a four-step synthesis at an isotopic enrichment level of 99% and in 14% overall chemical yield starting from 4-hydroxy-[ring-U-13C6]benzaldehyde (3). The hydrogenation of [13C6]JTT-501 over Pd/C gave [13C6]JTP-20604 in 90% chemical yield. Copyright © 2003 John Wiley & Sons, Ltd.

  以 4-羟基-[环-U-13C6]苯甲醛（3）为起点，通过四步合成法获得了 13C 标记的 JTT-501，同位素富集度为 99%，总化学收率为 14%。在 Pd/C 上氢化 [13C6]JTT-501 得到 [13C6]JTP-20604 ，化学收率为 90%。Copyright © 2003 John Wiley & Sons, Ltd. All Rights Reserved.
• Metabolic analysis of the cinnamate/monolignol pathway in Carthamus tinctorius seeds by a stable-isotope-dilution method
  作者：Norikazu Sakakibara、Tomoyuki Nakatsubo、Shiro Suzuki、Daisuke Shibata、Mikio Shimada、Toshiaki Umezawa

  DOI：10.1039/b616705e

  日期：——

  The present study established a system for comprehensive metabolic analysis of the cinnamate/monolignol and lignan pathways by the use of a stable-isotope-dilution method. The system was successfully applied to characterization of the pathways in Carthamus tinctorius cv. Round-leaved White maturing seeds in combination with administration of stable-isotope-labelled precursors. Experimental results obtained using this technique strongly suggested the intermediacy of ferulic acid in lignan biosynthesis in the plant.

  本研究通过使用稳定同位素稀释法建立了一个对肉桂酸/单木酚和木脂素途径进行综合代谢分析的系统。该系统成功应用于对红花胭脂树（Carthamus tinctorius cv. Round-leaved White）成熟种子中结合稳定同位素标记前体施用途径的表征。使用该技术获得的实验结果有力地表明了阿魏酸在植物木脂素生物合成中的中介作用。
• Assignment of Resonance Raman Spectrum of Photoactive Yellow Protein in Its Long-Lived Blue-Shifted Intermediate
  作者：Masashi Unno、Masato Kumauchi、Jun Sasaki、Fumio Tokunaga、Seigo Yamauchi

  DOI：10.1021/jp026448z

  日期：2003.3.1

  Photoactive yellow protein (PYP) is a bacterial photoreceptor containing a 4-hydroxycinnamyl chromophore. We report the resonance Raman spectra for the long-lived blue-shifted intermediate of PYP whose chromophore is isotopically labeled with 13C at the carbonyl carbon atom or at the ring carbon atoms. Spectra have been also measured with PYP in D2O where the phenolic hydroxyl group of the chromophore

  光敏黄色蛋白 (PYP) 是一种含有 4-羟基肉桂基发色团的细菌光感受器。我们报告了 PYP 的长寿命蓝移中间体的共振拉曼光谱，其生色团在羰基碳原子或环碳原子处用 13C 同位素标记。光谱也用 PYP 在 D2O 中测量，其中发色团的酚羟基被氘化。所有观察到的拉曼谱带都是根据观察到的同位素位移和使用密度泛函理论的正态计算来分配的。完整的任务为未来通过振动光谱研究 PYP 中的光循环机制提供了一个令人满意的框架。
• Optimized synthesis of four isotopically labeled(13C-enriched) phenolic acids via a malonic acid condensation
  作者：Rebecca J. Robbins、Walter F. Schmidt

  DOI：10.1002/jlcr.869

  日期：2004.10.15

  Four isotopically (13C)-labeled phenolic acids (caffeic [M + 3], sinapic [M + 2], p-coumaric [M + 6] and ferulic [M + 6] acids) were synthesized via a simple one-step malonic acid condensation with a series of aldehydes. The aldehydes and the malonic acid were variously labeled and unlabeled to vary the enriched sites. 13C and 1H NMR analyses together confirmed the labeled positions. LC/MS confirmed the masses. These acids are intended for use as internal standards for isotope dilution mass spectrometry (IDMS). Copyright © 2004 John Wiley & Sons, Ltd. (1)

  四种同位素（13C）标记的酚酸（咖啡酸[M + 3]、山奈酸[M + 2]、对香豆酸[M + 6]和阿魏酸[M + 6]）是通过简单的丙二酸与一系列醛缩合一步合成的。为了改变富集位点，对醛和丙二酸进行了不同的标记和非标记。13C 和 1H NMR 分析共同证实了标记的位置。LC/MS 确认了质量。这些酸可用作同位素稀释质谱法 (IDMS) 的内部标准。Copyright © 2004 John Wiley & Sons, Ltd. All Rights Reserved. (1)