5-bromomethyl fluorescein

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 5-bromomethyl fluorescein
• 英文别名: 5-(Bromomethyl)-2-(3-hydroxy-6-oxoxanthen-9-yl)benzoic acid
• 化学式: C₂₁H₁₃BrO₅
• 分子量: 425.235
• InChiKey: YHTMLUJBXDCVND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  棕榈酸 、 5-bromomethyl fluorescein 在 18-冠醚-6 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 1.0h， 生成 5-Hexadecanoyloxymethyl-2-(6-hydroxy-3-oxo-3H-xanthen-9-yl)-benzoic acid 、 2-(6-Hexadecanoyloxy-3-oxo-3H-xanthen-9-yl)-5-hydroxymethyl-benzoic acid
  参考文献：
  名称：

  摘要：

  Purpose. 5-Bromomethyl fluorescein (5-BMF) was evaluated in this work as a pre-column, off-line derivatizing reagent for analytes containing a free carboxyl group. The reagent possessed high molar absorptivity and quantum yield and it's excitation maximum matched the intense 488.0 nm emission line of an argon ion laser. The thermal and photo-stability of the reagent were also suitable for our work. Methods. A mixture of 5-BMF, palmitic acid, 18-crown-6 and potassium carbonate was reacted at 76 degrees C for one hour. The reaction yield was maximized by a sequential single-factor optimization of the reaction variables. Spectral characterizations were accomplished using conventional instrumentation and detection limits were evaluated using a laboratory constructed laser-induced fluorescence (LIF) detector which was optimized for concentration detection. Results. Two apparent conjugates of palmitic acid were formed under the reaction conditions employed. The conjugate chosen for quantitative purposes was stable at room temperature over 24 hours and possessed high molar absorptivity (128,832 M(-1)cm(-1)) and quantum yield (0.82) under basic conditions. The excitation and emission maxima of the conjugate were 500 nm and 523 nm respectively which maintains suitability for argon-ion laser excitation. An argon-ion LIF detector suitable for use with conventional liquid chromatography was constructed. A detection limit of 7.56 x 10(-10) M of palmitic acid was achieved at a signal to noise ratio of three, using the strong 488.0 nm laser emission line and a commercially available flow cell component. This corresponds to 38 femtomoles of palmitic acid on-column. Conclusion. The concentration detection limit was superior to literature reports for detection of fatty acids. The mass detection limit provided approximately an order of magnitude improvement over conventional fluorescence. The reagent is potentially useful for analysis of carboxyl containing analytes at low concentrations.

  DOI：

  10.1023/a:1016285709682

文献信息

• US20140256911A1
  申请人：——

  公开号：US20140256911A1

  公开（公告）日：2014-09-11
• Preparation of Oligo Conjugates
  申请人：Emerald Therapeutics, Inc.

  公开号：US20160333045A1

  公开（公告）日：2016-11-17

  Conjugated molecules are prepared that comprise a predetermined number of oligo conjugation components. The conjugated molecules also may comprise one or more detectable labels. Preparation of these molecules can be implemented according to an asymmetric or a symmetric conjugation strategy.
• PREPARATION OF OLIGO CONJUGATES
  申请人：Emerald Therapeutics, Inc.

  公开号：US20220009956A1

  公开（公告）日：2022-01-13

  Conjugated molecules are prepared that comprise a predetermined number of oligo conjugation components. The conjugated molecules also may comprise one or more detectable labels. Preparation of these molecules can be implemented according to an asymmetric or a symmetric conjugation strategy.
• US7160735B2
  申请人：——

  公开号：US7160735B2

  公开（公告）日：2007-01-09
• US9289502B2
  申请人：——

  公开号：US9289502B2

  公开（公告）日：2016-03-22