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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Chromium scavenging ability of silver nanoparticles in human erythrocytes, real samples and their effect on the catalase enzyme.
Rasheed W, et al.
New. J. Chem., 40(4), 3793-3802 (2016)
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)
José Luis Martínez-Hernández et al.
Applied biochemistry and biotechnology, 160(7), 2045-2053 (2009-09-22)
The production of extracellular and mycelia-associated penicillin G acylase (maPGA) with Mucor griseocyanus H/55.1.1 by surface-adhesion fermentation using Opuntia imbricata, a cactus, as a natural immobilization support was studied. Enzyme activity to form 6-aminopencillanic acid (6-APA) from penicillin G was
Global Trade Item Number
| SKU | GTIN |
|---|---|
| A70909-10G | 04061833383506 |
| A70909-50G | 04061833383513 |