6-Aminopenicillanic Acid

Description

6-aminopenicillanic acid is 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 pharmacologic characteristics.

It has a role as an allergen. 6-Aminopenicillanic Acid derives from a penicillanic acid. It is a conjugate base of a 6-aminopenicillanate. It is a tautomer of a 6-aminopenicillanic acid zwitterion.

6 aminopenicillanic acid Basic information

Product Name:	6-Aminopenicillanic acid
Synonyms:	6-AMINO-2,2-DIMETHYL-5-OXOPERHYDROAZETO[2,1-B][1,3]THIAZOLE-3-CARBOXYLIC ACID;6-AMINO-3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLO[3.2.0]HEPTANE-2-CARBOXYLIC ACID;6-APA;(+)-6-AMINOPENICILLANIC ACID; 6-AMINOPENICILLANIC ACID; 6-AMINO PENICILLINIC ACID; 7-AMINO-3,3-DIMETHYL-6-OXO-2-THIA-5-AZABICYCLO[3.2.0]HEPTANE-4-CARBOXYLIC ACID; (25,5R,6R)-6-AMINO-3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLO[3.2.0]HEPTANE-2-CARBOXYLIC ACID
CAS:	551-16-6
MF:	C8H12N2O3S
MW:	216.26
EINECS:	208-993-4
Product Categories:	Chemical Intermediate; Antibiotics for Research and Experimental Use; beta-Lactams ;Biochemistry; API; Organic acids
Mol File:	551-16-6.mol

6 aminopenicillanic acid Chemical Structure

6-Aminopenicillanic acid

6 apa Chemical Properties

Melting point	198-200 °C (dec.)(lit.)
alpha	276.3 º (c=1.2, 0.1N HCl 22 ºC)
Boiling point	460.2±45.0 °C(Predicted)
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
InChIKey	NGHVIOIJCVXTGV-SDKNWNMFSA-N
CAS DataBase Reference	551-16-6(CAS DataBase Reference)
EPA Substance Registry System	6-Aminopenicillanic acid (551-16-6)

Penin Usage And Synthesis

Chemical Properties	WHITE TO CREAM FINE POWDER
Uses	(+)-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.
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.
Safety Profile	Questionable carcinogen with experimental tumorigenic data. When heated to decomposition it emits very toxic fumes of NOx and SOx.