7-ACA

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7-Aminocephalosporanic acid
Partially condensed, stereo, skeletal formula of 7-aminocephalosporanic acid
7-ACA-3D-balls.png
Names
Systematic IUPAC name
3-(Acetyloxymethyl)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Other names
7-Aminocephalosporinic acid
Identifiers
957-68-6 YesY
3D model (Jmol) Interactive image
3DMet B02139
Abbreviations 7-ACA
622637, 8919572
ChEBI CHEBI:2255 N
ChEMBL ChEMBL1161449 N
ChemSpider 390087 YesY
ECHA InfoCard 100.012.259
EC Number 213-485-0
KEGG C07756 N
MeSH 7-Aminocephalosporanic+acid
PubChem 483168
Properties
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 pictograms The health hazard pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word Danger
H317, H334
P261, P280, P342+311
Harmful Xn
R-phrases R42/43[1]
S-phrases S22 S36/37[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

7-ACA (7-aminocephalosporanic acid) is the core chemical structure for the synthesis of cephalosporin antibiotics and intermediates. It can be obtained by chemoenzymatic hydrolysis of cephalosporin C.[2][3]

See also[edit]

References[edit]

  1. ^ 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. 
  2. ^ 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.