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7-ACA

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7-Aminocephalosporanic acid
Names


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	957-68-6^Y
3D model (JSmol)	Interactive image
3DMet	B02205
Abbreviations	7-ACA
Beilstein Reference	622637, 8919572
ChEBI	CHEBI:2255^Y
ChEMBL	ChEMBL1161449^Y
ChemSpider	390087^Y
ECHA InfoCard	100.012.259
EC Number	213-485-0
KEGG	C07756^Y
MeSH	7-Aminocephalosporanic+acid
PubChem CID	483168
UNII	9XI67897RG^Y
CompTox Dashboard (EPA)	DTXSID9045342
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^Y Key: HSHGZXNAXBPPDL-HZGVNTEJSA-N^Y
SMILES O=C2N1/C(=C(\CS[C@@H]1[C@@H]2N)COC(=O)C)C(=O)O
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 (pK_a)	2.59
Basicity (pK_b)	11.41
Hazards
GHS labelling:
Pictograms
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 [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references

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

References[edit]

^ 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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