A70909
(+)-6-Aminopenicillanic acid
96%
Synonym(s):
(2S,5R,6R)-6-Amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-APA
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About This Item
Empirical Formula (Hill Notation):
C8H12N2O3S
CAS Number:
Molecular Weight:
216.26
UNSPSC Code:
12352005
NACRES:
NA.22
PubChem Substance ID:
EC Number:
208-993-4
Beilstein/REAXYS Number:
15080
MDL number:
Assay:
96%
Form:
powder
Quality Level
assay
96%
form
powder
optical activity
[α]22/D +276.3°, c = 1.2 in 0.1 M HCl
mp
198-200 °C (dec.) (lit.)
antibiotic activity spectrum
Gram-positive bacteria
mode of action
cell wall synthesis | interferes
storage temp.
2-8°C
SMILES string
CC1(C)S[C@@H]2[C@H](N)C(=O)N2[C@H]1C(O)=O
InChI
1S/C8H12N2O3S/c1-8(2)4(7(12)13)10-5(11)3(9)6(10)14-8/h3-4,6H,9H2,1-2H3,(H,12,13)/t3-,4+,6-/m1/s1
InChI key
NGHVIOIJCVXTGV-ALEPSDHESA-N
General description
(+)-6-Aminopenicillanic acid is the core moiety of different penicillins. It can be prepared from the benzylpenicillin silyl ester via cleavage of the amide bond. The coating of (+)-6-aminopenicillanic acid on silver nanoparticles (6APA-AgNPs), imparts them with an ability to detect chromium (IV) in human erythrocytes.
Chemical structure: β-lactam
Application
(+)-6-Aminopenicillanic acid can be used as a starting material for the synthesis of (6S,7S)-cephalosporins, and organotin polyamine esters by reacting with organotin dihalides via interfacial polycondensation.
It reacts with higher amino acid Schiff bases to form the corresponding β-lactam derivatives.4
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signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2
Storage Class
11 - Combustible Solids
wgk
WGK 2
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Faceshields, Gloves
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Organotin polyamine esters from reaction of 6-aminopenicillanic acid and organotin dihalides
Carraher Jr CE, et al.
J. Polym. Mater., 29(4), 387-387 (2012)
6-aminopenicillanic acid.
Rolinson GN.
Chemotherapy, 2(1), 52-59 (1961)
An efficient nonenzymatic conversion of benzylpenicillin to 6-aminopenicillanic acid.
Weissenburger HWO and Van Der Hoeven MG.
Rec. Trav. Chim., 89(10), 1081-1084 (1970)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| A70909-50G | 04061833383513 |
| A70909-10G | 04061833383506 |