Nitrocefin
Title: Nitrocefin
CAS Registry Number: 41906-86-9
CAS Name: (6R,7R)-3-[(1E)-2-(2,4-Dinitrophenyl)ethenyl]-8-oxo-7-[(2-thienylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Additional Names: 3-(2,4-dinitrostyryl)-(6R,7R)-7-(2-thienylacetamido)-ceph-3-em-4-carboxylic acid, E-isomer; 87/312
Molecular Formula: C21H16N4O8S2
Molecular Weight: 516.50
Percent Composition: C 48.83%, H 3.12%, N 10.85%, O 24.78%, S 12.42%
Literature References: Chromogenic cephalosporin. Prepd (not claimed): C. H. O'Callaghan et al., US 3830700 (1974 to Glaxo). Characterization and use in detection of b-lactamases: idem et al., Antimicrob. Agents Chemother. 1, 283 (1972). Synthesis: N. C. M. Barendse et al., Synthesis 1998, 145. Improved synthesis: M. Lee et al., J. Org. Chem. 70, 367 (2005). Review of commercially available nitrocefin-based b-lactamase tests: A. T. Meszaros et al., Am. Clin. Lab. 14, 20-22 (1995).
Properties: Orange solid, mp 103-113° (dec) (O'Callaghan, 1974); also reported as crystals from methanol, mp 167-169° (dec) (Lee). [a]D20 -224° (c = 1.0 in dioxane). Absorption max (ethanol): 231, 289, 386 nm (e 24300, 10300, 18000). Absorption max (0.1M pH 6 phosphate buffer): 233, 290, 391 nm (e 22200, 12200, 17400). Undergoes a color change from yellow to pink or red upon exposure to b-lactamases.
Melting point: mp 103-113° (dec); mp 167-169° (dec) (Lee)
Optical Rotation: [a]D20 -224° (c = 1.0 in dioxane)
Absorption maximum: Absorption max (ethanol): 231, 289, 386 nm (e 24300, 10300, 18000); Absorption max (0.1M pH 6 phosphate buffer): 233, 290, 391 nm (e 22200, 12200, 17400)
Use: In determn of b-lactamase activity in biological samples.

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