7-ACA

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 ;
3D model (JSmol)	Interactive image;
3DMet	B02205;
Abbreviations	7-ACA
Beilstein Reference	622637, 8919572
ChEBI	CHEBI:2255 ;
ChEMBL	ChEMBL1161449 ;
ChemSpider	390087 ;
ECHA InfoCard	100.012.259
EC Number	213-485-0;
KEGG	C07756 ;
MeSH	7-Aminocephalosporanic acid
PubChem CID	483168;
UNII	9XI67897RG ;
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 Key: HSHGZXNAXBPPDL-HZGVNTEJSA-N ;
	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)
log P	-1.87
Acidity (pKa)	2.59
Basicity (pKb)	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). verify (what is ?) Infobox references

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]

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.^[4]

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.
^ "7-Aminocephalosporanic Acid (7-ACA) Market". Markets Glob Market Research. Retrieved 30 August 2024.

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[chemblink-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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See also

References