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MilliporeSigma

A70909

Sigma-Aldrich

(+)-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
Beilstein/REAXYS Number:
15080
EC Number:
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22

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

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General description

(+)-6-Aminopenicillanic acid is the core moiety of different penicillins.[1] It can be prepared from the benzylpenicillin silyl ester via cleavage of the amide bond.[2] The coating of (+)-6-aminopenicillanic acid on silver nanoparticles (6APA-AgNPs), imparts them with an ability to detect chromium (IV) in human erythrocytes.[3]
Chemical structure: ß-lactam

Application

(+)-6-Aminopenicillanic acid can be used as a starting material for the synthesis of (6S,7S)-cephalosporins,[4] and organotin polyamine esters by reacting with organotin dihalides via interfacial polycondensation.[5]
It reacts with higher amino acid Schiff bases to form the corresponding β-lactam derivatives.4

pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Eye Irrit. 2

Storage Class

11 - Combustible Solids

wgk_germany

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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Syntheses of (6S)-cephalosporins from 6-aminopenicillanic acid
Fekner T, et al.
Tetrahedron, 56(33), 6053-6074 (2000)
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)
6-aminopenicillanic acid.
Rolinson GN.
Chemotherapy, 2(1), 52-59 (1961)
Acute generalized exanthematous pustulosis (AGEP) induced by terbinafine and two different antibiotics: four recurrences.
Nolwenn Coquart et al.
European journal of dermatology : EJD, 20(5), 638-639 (2010-07-16)

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