酸性红94

酸性红94
	IUPAC名; 4,5,6,7-Tetrachloro-3′,6′-dihydroxy-2′,4′,5′,7′-tetraiodo-3H-spiro[[2]benzofuran-1,9′-xanthen]-3-one
别名	C.I. 45440; C.I.酸性红94; 孟加拉红; 孟加拉玫瑰红; 溶剂红141
识别
CAS号	4159-77-7
PubChem	69439
ChemSpider	62647
SMILES	O=C(O1)C2=C(C(Cl)=C(Cl)C(Cl)=C2Cl)C31C4=C(C(I)=C(O)C(I)=C4)OC5=C(I)C(O)=C(I)C=C53;
性质
化学式	C20H4Cl4I4O5
摩尔质量	973.67 g·mol−1
药理学
ATC代码	S01JA02（S01）
危险性
	GHS危险性符号;
GHS提示词	警告
H-术语	H315, H319, H335
P-术语	P261, P264, P271, P280, P302+352, P304+340, P305+351+338, P312, P321, P332+313, P337+313, P362, P403+233, P405
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

酸性红94（4,5,6,7-四氯-2',4',5',7'-四碘荧光素）是一种有机化合物，化学式为C₂₀H₄Cl₄I₄O₅。它可以四氯邻苯二甲酸酐（德语：Tetrachlorphthalsäureanhydrid）和间苯二酚为原料反应制得。^[1]它和碘甲烷在碳酸钾存在下于DMF中反应，可以得到6'-O-甲基酸性红94。^[2]

化學上的應用[编辑]

儘管孟加拉玫瑰紅在光化學上涉及的物種眾多^[3]，其也可用於在化學合成上作為三线态氧到單線態氧的轉化試劑。其後單線態氧可用於和烯及其他相似化合物進行[2+2]环加成反应。

衍生物和鹽類[编辑]

孟加拉玫瑰紅可用於生成許多在醫學上有用的化學衍生物。其中一個孟加拉玫瑰紅的衍生物在研究中被稱為RB2，此衍生物由孟加拉玫瑰紅的醯胺化生成，進而去除了螢光和光敏性而改具有聲敏性，可以用於輔助在高強度集中的超聲波下治療癌症。^[4]

孟加拉玫瑰紅的鹽類包括其二鈉鹽 C₂₀H₂Cl₄I₄Na₂O₅ (CAS 632-69-9)，此二鈉鹽為一染料，具有其獨特性質和應用。^[5]

参考文献[编辑]

^ Singer, Jamie; Wachter, Eric A.; Scott, Timothy; Lutz, Marlon; Babiak, Kevin; Damireddi, Sahadeva Reddy; Durrwachter, J. Robert. Process for the synthesis of rose bengal and related xanthenes. 2014 US 20140343296 A1.
^ Nicolas Pietrancosta, Albane Kessler, Franck-Cyril Favre-Besse, Nicolas Triballeau, Thomas Quentin, Bruno Giros, Salah El Mestikawy, Francine C. Acher. Rose Bengal analogs and vesicular glutamate transporters (VGLUTs). Bioorganic & Medicinal Chemistry. 2010-09, 18 (18): 6922–6933 [2023-02-28]. doi:10.1016/j.bmc.2010.06.069. （原始内容存档于2022-07-04）（英语）.
^ Ludvíková, Lucie; Friš, Pavel; Heger, Dominik; Šebej, Peter; Wirz, Jakob; Klán, Petr. Photochemistry of rose bengal in water and acetonitrile: a comprehensive kinetic analysis. Physical Chemistry Chemical Physics. 2016, 18 (24): 16266–16273. Bibcode:2016PCCP...1816266L. ISSN 1463-9076. PMID 27253480. doi:10.1039/C6CP01710J （英语）.
^ Kim, Y; Valentina Rubio; Jianjun Qi; Rongmin Xia; Zheng-Zheng Shi; Leif Peterson; Ching-Hsuan Tung; Brian E. O'Neill. Cancer treatment using an optically inert rose bengal derivative combined with pulsed focused ultrasound. AIP Conference Proceedings. 2012, 1481 (1): 175. Bibcode:2012AIPC.1481..175K. doi:10.1063/1.4757330. Published as Kim, YS; Rubio, V; Qi, J; Xia, R; Shi, ZZ; Peterson, L; Tung, CH; O'Neill, BE. Cancer treatment using an optically inert Rose Bengal derivative combined with pulsed focused ultrasound. J Control Release. 2011, 156 (3): 315–22. PMC 3230682 . PMID 21871506. doi:10.1016/j.jconrel.2011.08.016.
^ Rose Bengal Sodium Salt. Sigma-Aldrich. Sigma Aldrich Co. [12 November 2013]. （原始内容存档于2020-09-28）.

外部链接[编辑]

醫學主題詞表（MeSH）：Rose+Bengal
Absorption and extinction data （页面存档备份，存于互联网档案馆）

[1] Singer, Jamie; Wachter, Eric A.; Scott, Timothy; Lutz, Marlon; Babiak, Kevin; Damireddi, Sahadeva Reddy; Durrwachter, J. Robert. Process for the synthesis of rose bengal and related xanthenes. 2014 US 20140343296 A1.

[2] Nicolas Pietrancosta, Albane Kessler, Franck-Cyril Favre-Besse, Nicolas Triballeau, Thomas Quentin, Bruno Giros, Salah El Mestikawy, Francine C. Acher. Rose Bengal analogs and vesicular glutamate transporters (VGLUTs). Bioorganic & Medicinal Chemistry. 2010-09, 18 (18): 6922–6933 [2023-02-28]. doi:10.1016/j.bmc.2010.06.069. （原始内容存档于2022-07-04）（英语）.

[3] Ludvíková, Lucie; Friš, Pavel; Heger, Dominik; Šebej, Peter; Wirz, Jakob; Klán, Petr. Photochemistry of rose bengal in water and acetonitrile: a comprehensive kinetic analysis. Physical Chemistry Chemical Physics. 2016, 18 (24): 16266–16273. Bibcode:2016PCCP...1816266L. ISSN 1463-9076. PMID 27253480. doi:10.1039/C6CP01710J （英语）.

[4] Kim, Y; Valentina Rubio; Jianjun Qi; Rongmin Xia; Zheng-Zheng Shi; Leif Peterson; Ching-Hsuan Tung; Brian E. O'Neill. Cancer treatment using an optically inert rose bengal derivative combined with pulsed focused ultrasound. AIP Conference Proceedings. 2012, 1481 (1): 175. Bibcode:2012AIPC.1481..175K. doi:10.1063/1.4757330. Published as Kim, YS; Rubio, V; Qi, J; Xia, R; Shi, ZZ; Peterson, L; Tung, CH; O'Neill, BE. Cancer treatment using an optically inert Rose Bengal derivative combined with pulsed focused ultrasound. J Control Release. 2011, 156 (3): 315–22. PMC 3230682 . PMID 21871506. doi:10.1016/j.jconrel.2011.08.016.

[5] Rose Bengal Sodium Salt. Sigma-Aldrich. Sigma Aldrich Co. [12 November 2013]. （原始内容存档于2020-09-28）.

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