Skip to Content
MilliporeSigma
All Photos(2)

Key Documents

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

Sign Into View Organizational & Contract Pricing

Select a Size

50 ML
$154.00

$154.00


Estimated to ship onMarch 17, 2025


Request a Bulk Order

Select a Size

Change View
50 ML
$154.00

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

$154.00


Estimated to ship onMarch 17, 2025


Request a Bulk Order

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

Looking for similar products? Visit Product Comparison Guide

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


  • Choose from one of the most recent versions:

    Certificates of Analysis (COA)

    Lot/Batch Number

    Don't see the Right Version?

    If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

    Already Own This Product?

    Find documentation for the products that you have recently purchased in the Document Library.

    Visit the Document Library

    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)
    Anand Pai et al.
    Proceedings of the National Academy of Sciences of the United States of America, 109(48), 19810-19815 (2012-11-13)
    Bacteria secrete a variety of public good exoproducts into their environment. These exoproducts are typically produced under the control of quorum sensing (QS), a signaling mechanism by which bacteria sense and respond to changes in their density. QS seems to
    6-aminopenicillanic acid.
    Rolinson GN.
    Chemotherapy, 2(1), 52-59 (1961)
    Teresa Jackowska et al.
    Medycyna wieku rozwojowego, 12(2 Pt 2), 705-712 (2009-05-08)
    the basis of urinary tract infection (UTI) diagnosis in children is based on positive results of microbiological tests. The selection of an antimicrobial drug for empirical treatment and prophylaxis of UTI is determined by the susceptibility of bacterial strains isolated
    Ye-Wang Zhang et al.
    Applied microbiology and biotechnology, 88(1), 49-55 (2010-06-23)
    A one-pot, two-step enzymatic synthesis of amoxicillin from penicillin G, using penicillin acylase, is presented. Immobilized penicillin acylase from Kluyvera citrophila was selected as the biocatalyst for its good pH stability and selectivity. Hydrolysis of penicillin G and synthesis of

    Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

    Contact Technical Service