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HomeProduct name list6-Aminopenicillanic acid

6-Aminopenicillanic acid

Synonym(s):(+)-6-Aminopenicillanic acid;(2S,5R,6R)-6-Amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid;6-aminopenicillanic acid;6-APA

  • CAS NO.:551-16-6
  • Empirical Formula: C8H12N2O3S
  • Molecular Weight: 216.26
  • MDL number: MFCD00005176
  • EINECS: 208-993-4
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-08-21 22:41:43
6-Aminopenicillanic acid Structural

What is 6-Aminopenicillanic acid?

Description

A broad range of affordable semisynthetic penicillins and chephalosporins has been made possible by the use of the intermediate 6-aminopenicillanic acid (6-APA).

Chemical properties

WHITE TO CREAM FINE POWDER

The Uses of 6-Aminopenicillanic acid

(+)-6-Aminopenicillanic Acid is the core structure in penicillins, obtained from the fermentation brew of the Penicillium mold. (+)-6-Aminopenicillanic Acid is used as the main starting block for the preparation of numerous semisynthetic penicillins.

The Uses of 6-Aminopenicillanic acid

6-Aminopenicillanic acid is the basic unit in penicillin?s, which is obtained from the fermentation brew of the Penicillium mold. It acts as a starting material for the preparation of many semisynthetic penicillins. Further, it serves as apharmaceutical intermediate. In addition to this, it is used in antibiotics research and experimental application.

Definition

ChEBI: A penicillanic acid compound having a (6R)-amino substituent. The active nucleus common to all penicillins, it may be substituted at the 6-amino position to form the semisynthetic penicillins, resulting in a variety of antibacterial and ph rmacologic characteristics.

General Description

Chemical structure: ?-lactam

Flammability and Explosibility

Non flammable

Safety Profile

Questionable carcinogen with experimental tumorigenic data. When heated to decomposition it emits very toxic fumes of NOx and SOx.

Purification Methods

This acid crystallises from water. [Kleppe & Stroninger J Biol Chem 254 4856 1979,Beilstein 27 III/IV 2858.]

Properties of 6-Aminopenicillanic acid

Melting point: 198-200 °C (dec.)(lit.)
Boiling point: 460.2±45.0 °C(Predicted)
alpha  276.3 º (c=1.2, 0.1N HCl 22 ºC)
Density  1.3418 (rough estimate)
refractive index  1.6300 (estimate)
storage temp.  2-8°C
solubility  2.46g/l
pka pKa 2.3 (Uncertain)
form  Fine Powder
color  White to cream
PH 3.4 (100g/l, H2O)
optical activity [α]22/D +276.3°, c = 1.2 in 0.1 M HCl
Water Solubility  Soluble in water and hydrochoric acid.
Merck  14,458
BRN  15080
Stability: Light sensitive
CAS DataBase Reference 551-16-6(CAS DataBase Reference)
EPA Substance Registry System 6-Aminopenicillanic acid (551-16-6)

Safety information for 6-Aminopenicillanic acid

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H319:Serious eye damage/eye irritation
Precautionary Statement Codes P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P337+P313:IF eye irritation persists: Get medical advice/attention.

Computed Descriptors for 6-Aminopenicillanic acid

InChIKey NGHVIOIJCVXTGV-SDKNWNMFSA-N

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