(+)-6-Aminopenicillanic acid


6-APA, (2S,5R,6R)-6-Amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Empirical Formula (Hill Notation):
CAS Number:
Molecular Weight:
Beilstein/REAXYS Number:
EC Number:
MDL number:
PubChem Substance ID:

Quality Level



optical activity

[α]22/D +276.3°, c = 1.2 in 0.1 M HCl


198-200 °C (dec.) (lit.)

Mode of action

cell wall synthesis | interferes

antibiotic activity spectrum

Gram-positive bacteria

storage temp.


SMILES string




InChI key


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General description

Chemical structure: ß-lactam
(+)-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.


It reacts with higher amino acid Schiff bases to form the corresponding β-lactam derivatives.4
(+)-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.


10, 50 g in glass bottle

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. A70909.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves


NONH for all modes of transport

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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)
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)
6-aminopenicillanic acid.
Rolinson GN.
Chemotherapy, 2(1), 52-59 (1961)
David A Harris et al.
Bioorganic & medicinal chemistry letters, 19(14), 3787-3790 (2009-05-12)
We report the first synthesis of a 5S penem, known to bind bacterial type I signal peptidase, from the commercially available and inexpensive 6-aminopenicillanic acid. We report the first in vivo activity of the compound and use structure-activity relationship studies...
Joanna Skiba et al.
European journal of medicinal chemistry, 57, 234-239 (2012-10-18)
We report on the synthesis of ferrocenyl-ampicillin and ferrocenyl-6-aminopenicillinic acid bioconjugates. Title compounds were characterized by (1)H NMR, IR, MS and elemental analysis. These novel ferrocenyl-antibiotic conjugates were also investigated by cyclic voltammetry (CV). Ferrocenyl-ampicillin complexes revealed reversible uncomplicated oxidation...

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