191140

7-Aminocephalosporanic acid

98%

• Synonym(s): 7-ACA
• Empirical Formula (Hill Notation): C₁₀H₁₂N₂O₅S
• CAS Number: 957-68-6
• Molecular Weight: 272.28
• Beilstein/REAXYS Number: 622637
• EC Number: 213-485-0
• MDL number: MFCD00005177
• UNSPSC Code: 12352106
• PubChem Substance ID: 24851470
• NACRES: NA.22

Properties

• Quality Level: 200
• assay: 98%
• form: powder
• optical activity: [α]19/D +90°, c = 0.5 in KH₂PO₄/trace NaOH
• reaction suitability: reaction type: solution phase peptide synthesis
• mp: >300 °C (lit.)
• antibiotic activity spectrum: Gram-positive bacteria
• application(s): peptide synthesis
• mode of action: cell wall synthesis | interferes
• storage temp.: 2-8°C
• SMILES string: [H][C@]12SCC(COC(C)=O)=C(N1C(=O)[C@H]2N)C(O)=O
• 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
• InChI key: HSHGZXNAXBPPDL-HZGVNTEJSA-N

Description

General description

Chemical structure: ß-lactam

Application

7-Aminocephalosporanic acid (7-ACA) can be used as a starting material to synthesize:

• Cefotaxime by acylation reaction with S-benzothiazol-2-yl(2-amino-4-thiazolyl)(methoxyimino)thioacetate (MAEM) in the presence of triethylamine.[1]
• Cefpodoxime proxetil, a third-generation antibiotic via cefotaxime intermediate.[1]
• Sodium 3′-substituted cephalosporanate sulfone derivatives as potential inhibitors of β-lactamase.[2]

Potent inhibitor of bacterial (S. aureus) β-lactamase.[3]

Safety Information

• pictograms: GHS08
• signalword: Danger
• hcodes: H317,H334
• pcodes: P261 - P272 - P280 - P284 - P302 + P352 - P333 + P313
• Hazard Classifications: Resp. Sens. 1 - Skin Sens. 1
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: dust mask type N95 (US), Eyeshields, Faceshields, Gloves