7-ACA
Names | |
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IUPAC name 3-[(Acetyloxy)methyl]-7β-amino-3,4-didehydrocepham-4-carboxylic acid | |
Systematic IUPAC name (6R,7R)-3-[(Acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid | |
Other names 7-Aminocephalosporinic acid | |
Identifiers | |
CAS Number |
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3D model (JSmol) |
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3DMet |
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Abbreviations | 7-ACA |
Beilstein Reference | 622637, 8919572 |
ChEBI |
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ChEMBL |
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ChemSpider |
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ECHA InfoCard | 100.012.259 |
EC Number |
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KEGG |
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MeSH | 7-Aminocephalosporanic+acid |
PubChem CID |
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UNII |
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CompTox Dashboard (EPA) |
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InChI
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Properties | |
Chemical formula | C10H12N2O5S |
Molar mass | 272.27 g·mol−1 |
Melting point | 300 °C (572 °F; 573 K)[1] |
log P | -1.87 |
Acidity (pKa) | 2.59 |
Basicity (pKb) | 11.41 |
Hazards | |
GHS labelling: | |
Danger | |
H317, H334 | |
P261, P280, P342+P311 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references |
Chemical compound
7-ACA (7-aminocephalosporanic acid) is the core chemical structure (a synthon) for the synthesis of cephalosporin antibiotics and intermediates. It can be obtained by chemoenzymatic hydrolysis of cephalosporin C.[2][3]
See also
References
- ^ 7-ACA at Chemblink
- ^ Tan, Qiang; Zhang, Yewang; Song, Qingxun; Wei, Dongzhi (2010). "Single-pot conversion of cephalosporin C to 7-aminocephalosporanic acid in the absence of hydrogen peroxide". World Journal of Microbiology & Biotechnology. 26 (1): 145–152. doi:10.1007/s11274-009-0153-9. S2CID 84749385.
- ^ Tan, Qiang; Song, Qingxun; Wei, Dongzhi (2006). "Single-pot conversion of cephalosporin C to 7-aminocephalosporanic acid using cell-bound and support-bound enzymes". Enzyme and Microbial Technology. 39 (5): 1166–1172. doi:10.1016/j.enzmictec.2006.02.028.
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