7-Aminocephalosporanic acid

• CAT Number: I005680
• CAS Number: 957-68-6
• Molecular Formula: C10H12N2O5S
• Molecular Weight: 272.28
• Purity: ≥95%
• Target: Beta-lactamase
• Solubility: 10 mM in DMSO
• Storage: 3 years -20℃ powder
• IUPAC Name: (6R,7R)-3-(acetyloxymethyl)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• InChI: InChI=1S/C10H12N2O5S/c1-4(13)17-2-5-3-18-9-6(11)8(14)12(9)7(5)10(15)16/h6,9H,2-3,11H2,1H3,(H,15,16)/t6-,9-/m1/s1
• InChIKey: HSHGZXNAXBPPDL-HZGVNTEJSA-N
• SMILES: CC(=O)OCC1=C(N2[C@@H]([C@@H](C2=O)N)SC1)C(=O)O

7-Aminocephalosporanic acid (Cat No.:I005680) is a key intermediate in the synthesis of cephalosporin antibiotics, used as a building block for various semi-synthetic derivatives. Structurally derived from cephalosporin C, 7-ACA provides the core beta-lactam ring essential for antibacterial activity. It inhibits bacterial cell wall synthesis, leading to cell death, and has been instrumental in developing broad-spectrum antibiotics effective against both gram-positive and gram-negative bacteria. 7-ACA’s versatility in pharmaceutical synthesis has made it a foundational compound in the production of widely used antibiotics, enhancing therapeutic options for bacterial infections.

Reference

Loder, Bronwen, G. G. F. Newton, and E. P. Abraham. /The Cephalosporin C Nucleus (7-aminocephalosporanic Acid) and Some of Its Derivatives./ Biochem. J. Biochemical Journal 79.2 (1961): 408-16. Web.