6-Aminopenicillanic acid

6-Aminopenicillanic acid Basic information
Product Name:6-Aminopenicillanic acid
Synonyms:6-AMINO-3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLO[3.2.0]HEPTANE-2-CARBOXYLIC ACID;(+)-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;(2S,5R,6R)-6-AMINO-3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLO-[3.2.0]HEPTANE-2-CARBOXYLIC ACID;aminopenicillanicacid
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 (Antibiotics for Research and Experimental Use);Biochemistry;Used as pharmaceutical intermediates;API;Organic acids
Mol File:551-16-6.mol
6-Aminopenicillanic acid Structure
6-Aminopenicillanic acid 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
form Fine Powder
pkapKa 2.3 (Uncertain)
color White to cream
PH3.4 (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
InChIKeyNGHVIOIJCVXTGV-SDKNWNMFSA-N
LogP-3.87 at 22.5℃
CAS DataBase Reference551-16-6(CAS DataBase Reference)
EPA Substance Registry System6-Aminopenicillanic acid (551-16-6)
Safety Information
Hazard Codes Xn
Risk Statements 42/43
Safety Statements 22-36/37-45-37-24-36
WGK Germany 2
RTECS XH8225000
10
TSCA Yes
HS Code 29349990
MSDS Information
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6-Aminopenicillanic acid English
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6-Aminopenicillanic acid Usage And Synthesis
Chemical PropertiesWHITE TO CREAM FINE POWDER
Uses6-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.
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.
DefinitionChEBI: 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 DescriptionChemical structure: ?-lactam
Flammability and ExplosibilityNonflammable
Safety ProfileQuestionable carcinogen with experimental tumorigenic data. When heated to decomposition it emits very toxic fumes of NOx and SOx.
Purification MethodsThis acid crystallises from water. [Kleppe & Stroninger J Biol Chem 254 4856 1979,Beilstein 27 III/IV 2858.]
acyl-CoA-6-aminopenicillanic acid acyltransferase 7-(2,2-DIMETHYL-5-OXO-4-PHENYL-IMIDAZOLIDIN-1-YL)-3,3-DIMETHYL-6-OXO-2-THIA-5-AZABICYCLO[3.2.0]HEPTANE-4-CARBOXYLIC ACID PIPERACILLIN SODIUM IMP. H (EP): 6-AMINOPENICILLANIC ACID MM(CRM STANDARD) 6α-[(Butylthio)acetyl]aminopenicillanic acid Ethyl 2-(Chlorosulfonyl)acetate Bis[6α-(phenylacetyl)aminopenicillanic acid]calcium salt EC 2.6.1.2 BENZYLPENICILLIN POTASSIUM IMP. A (EP): 6-AMINOPENICILLANIC ACID MM(CRM STANDARD) Cloxacillin-13C4 SodiuM Salt FLUCLOXACILLIN SODIUM IMP. C (EP): 6-AMINOPENICILLANIC ACID MM(CRM STANDARD) OXACILLIN SODIUM DICLOXACILLIN SODIUM IMP. C (EP): 6-AMINOPENICILLANIC ACID MM(CRM STANDARD) 6-((biotinyl-N-epsilon-aminocaproyl-N-cystamine-N'-carbonyl)methylsulfonyl)aminopenicillanic acid S,S-dioxide 6-(biotinyl-N-epsilon-aminocaproyl-N-cystamine-N'-glutaryl)aminopenicillanic acid Mecillinam CARBOXYLIC ACID 2-(2-Aminothiazol-4-yl)glyoxylic acid Nafcillin sodium salt monohydrate

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