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Merck
CN

A1005

(+)-6-Aminopenicillanic acid

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:
551-16-6
Molecular Weight:
216.26
EC Number:
208-993-4
UNSPSC Code:
12352200
MDL number:
MFCD00005176
Beilstein/REAXYS Number:
15080

Key Documents

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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

SMILES string

CC1(C)S[C@@H]2[C@H](N)C(=O)N2[C@H]1C(O)=O

mp

198-200 °C (dec.) (lit.)

mode of action

cell wall synthesis | interferes

storage temp.

2-8°C

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General description

Chemical structure: β-lactam

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H319

Hazard Classifications

Eye Irrit. 2

Storage Class

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
127H3424
094H3467
087F3530
085H3465
045H2501

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Zhiqiang Chen et al.
Journal of hazardous materials, 185(2-3), 905-913 (2010-10-26)
A full-scale test was conducted with an up-flow anaerobic sludge blanket (UASB) pre-treating pharmaceutical wastewater containing 6-aminopenicillanic acid (6-APA) and amoxicillin. The aim of the study is to investigate the performance of UASB in the condition of a high chemical
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
Yangyang Jiang et al.
Applied biochemistry and biotechnology, 144(2), 145-159 (2008-05-06)
A dodecane/thermosensitive polymer/water three-liquid-phase system was introduced for enzymatic hydrolysis of penicillin G (Pen G) for 6-aminopenicillanic acid (6-APA). The enzyme was covalently attached to the terminal of PEO-PPO-PEO polymer (L63), which would be transferred into a polymer coacervate phase
Chunqiu Tian et al.
Se pu = Chinese journal of chromatography, 29(11), 1128-1132 (2012-03-08)
A high performance capillary electrophoresis (HPCE) method was developed for the simultaneous determination of penicillin intermediate and penicillins in milk, including 6-amino-penicillanic acid (6-APA), penicillin G (PEN), ampicillin (AMP) and amoxicillin (AMO). The main parameters including the ion concentration and
Faridoon et al.
Bioorganic & medicinal chemistry letters, 22(7), 2555-2559 (2012-03-01)
Purple acid phosphatases (PAPs) are binuclear metallohydrolases that have a multitude of biological functions and are found in fungi, bacteria, plants and animals. In mammals, PAP activity is linked with bone resorption and over-expression can lead to bone disorders such
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