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7-ACA

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7-Aminocephalosporanic acid
Partially condensed, stereo, skeletal formula of 7-aminocephalosporanic acid
Names
IUPAC name 3--7β-amino-3,4-didehydrocepham-4-carboxylic acid
Systematic IUPAC name (6R,7R)-3--7-amino-8-oxo-5-thia-1-azabicyclooct-2-ene-2-carboxylic acid
Other names 7-Aminocephalosporinic acid
Identifiers
CAS Number
3D model (JSmol)
3DMet
Abbreviations 7-ACA
Beilstein Reference 622637, 8919572
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.012.259 Edit this at Wikidata
EC Number
  • 213-485-0
KEGG
MeSH 7-Aminocephalosporanic+acid
PubChem CID
UNII
CompTox Dashboard (EPA)
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/s1Key: HSHGZXNAXBPPDL-HZGVNTEJSA-N
SMILES
  • O=C2N1/C(=C(\CS12N)COC(=O)C)C(=O)O
Properties
Chemical formula C10H12N2O5S
Molar mass 272.27 g·mol
Melting point 300 °C (572 °F; 573 K)
log P -1.87
Acidity (pKa) 2.59
Basicity (pKb) 11.41
Hazards
GHS labelling:
Pictograms GHS08: Health hazard
Signal word Danger
Hazard statements H317, H334
Precautionary statements P261, P280, P342+P311
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) 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.

The production of 7-ACA (7-aminocephalosporanic acid) is predominantly segmented into two methods which is Enzymatic Hydrolysis and Chemical Cracking. These processes are essential for the synthesis of various cephalosporin antibiotics.

See also

References

  1. 7-ACA at Chemblink
  2. 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.
  3. 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.
  4. "7-Aminocephalosporanic Acid (7-ACA) Market". Markets Glob Market Research. Retrieved 30 August 2024.
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