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]
Quick Facts Names, Identifiers ...
7-Aminocephalosporanic acid
Partially condensed, stereo, skeletal formula of 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
Abbreviations
7-ACA
622637, 8919572
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.012.259
EC Number
KEGG
MeSH 7-Aminocephalosporanic+acid
UNII
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
O=C2N1/C(=C(\CS[C@@H]1[C@@H]2N)COC(=O)C)C(=O)O
Properties
C 10 H 12 N 2 O 5 S
Molar mass 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
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).
Close
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]
