Introduction：Basic information about 6-Aminopenicillanic acid CAS 551-16-6, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
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-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 |
| 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 |
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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 |
| pka | pKa 2.3 (Uncertain) |
| form | Fine Powder |
| color | White to cream |
| PH | 3.4 (100g/l, H2O) |
| Optical Rotation | [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 |
| 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 |
| InChIKey | NGHVIOIJCVXTGV-SDKNWNMFSA-N |
| SMILES | CC1(C)S[C@@H]2[C@H](N)C(=O)N2[C@H]1C(O)=O |
| LogP | -3.87 at 22.5℃ |
| CAS DataBase Reference | 551-16-6(CAS DataBase Reference) |
| EPA Substance Registry System | 6-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 |
| F | 10 |
| TSCA | TSCA listed |
| HS Code | 29349990 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Eye Irrit. 2 |
6-Aminopenicillanic acid 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. |
| Uses | 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 phrmacologic 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.] |
6-Aminopenicillanic acid Preparation Products And Raw materials
| Raw materials | Ammonium bicarbonate-->Ampicillin-->Penicillin G potassium salt-->Bis(2-dimethylaminoethyl) ether-->Ampicillin |
| Preparation Products | Imipenem-->Penicillin G-->Piperacillin-->Oxacillin sodium monohydrate-->CARBENICILLIN-->Flucloxacillin sodium-->[2S-(2alpha,5alpha,6alpha)]-6-bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid-->(2S-cis)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid-->(3S)-6,6-DIBROMO-2,2-DIMETHYLPENAM-3-CARBOXYLIC ACID 1,1-DIOXIDE-->methicillin-->4-Thiazolecarboxylic acid-->6β-Phthalimidopenicillanic Acid |
