酸性紅94
酸性紅94 | |
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IUPAC名 4,5,6,7-Tetrachloro-3′,6′-dihydroxy-2′,4′,5′,7′-tetraiodo-3H-spiro[[2]benzofuran-1,9′-xanthen]-3-one | |
別名 | C.I. 45440 C.I.酸性紅94 孟加拉紅 孟加拉玫瑰紅 溶劑紅141 |
識別 | |
CAS號 | 4159-77-7 ![]() |
PubChem | 69439 |
ChemSpider | 62647 |
SMILES |
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性質 | |
化學式 | C20H4Cl4I4O5 |
摩爾質量 | 973.67 g·mol−1 |
藥理學 | |
ATC代碼 | S01JA02(S01) |
危險性 | |
GHS危險性符號![]() | |
GHS提示詞 | 警告 |
H-術語 | H315, H319, H335 |
P-術語 | P261, P264, P271, P280, P302+352, P304+340, P305+351+338, P312, P321, P332+313, P337+313, P362, P403+233, P405 |
若非註明,所有數據均出自標準狀態(25 ℃,100 kPa)下。 |
![Rose bengal solid and in water](http://images.weserv.nl/?url=//upload.wikimedia.org/wikipedia/commons/thumb/0/05/%D0%91%D0%B5%D0%BD%D0%B3%D0%B0%D0%BB%D1%8C%D1%81%D0%BA%D0%B0%D1%8F_%D1%80%D0%BE%D0%B7%D0%B0.jpg/220px-%D0%91%D0%B5%D0%BD%D0%B3%D0%B0%D0%BB%D1%8C%D1%81%D0%BA%D0%B0%D1%8F_%D1%80%D0%BE%D0%B7%D0%B0.jpg)
酸性紅94(4,5,6,7-四氯-2',4',5',7'-四碘螢光素)是一種有機化合物,化學式為C20H4Cl4I4O5。它可以四氯鄰苯二甲酸酐和間苯二酚為原料反應製得。[1]它和碘甲烷在碳酸鉀存在下於DMF中反應,可以得到6'-O-甲基酸性紅94。[2]
化學上的應用
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線態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]環加成反應。
衍生物和鹽類
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音波下治療癌症。[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]
![](http://images.weserv.nl/?url=//upload.wikimedia.org/wikipedia/commons/thumb/c/c7/Rose_bengal_sodium_salt_structure.png/220px-Rose_bengal_sodium_salt_structure.png)
參考文獻
- ^ 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. (原始內容存檔於2022-07-04) (英語).
- ^ 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 (英語).
- ^ 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]. (原始內容存檔於2020-09-28).