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
• Empirical Formula (Hill Notation): C₈H₁₂N₂O₃S
• CAS Number: 551-16-6
• Molecular Weight: 216.26
• Beilstein/REAXYS Number: 15080
• EC Number: 208-993-4
• MDL number: MFCD00005176
• UNSPSC Code: 12352005
• PubChem Substance ID: 24891174
• NACRES: NA.22

Properties

• Quality Level: 200
• 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

Description

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

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H319
• pcodes: P264 - P280 - P305 + P351 + P338 - P337 + P313
• 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