CAS 551-16-6

6-Aminopenicillanic acid

Description:

6-Aminopenicillanic acid (6-APA) is a crucial intermediate in the synthesis of penicillin antibiotics. It is a beta-lactam compound characterized by a bicyclic structure that includes a thiazolidine ring and a beta-lactam ring. The presence of an amino group at the 6-position is essential for its biological activity, as it allows for the modification of the molecule to create various penicillin derivatives. 6-APA is typically a white to off-white crystalline powder that is soluble in water and exhibits a pH-dependent solubility profile. It is stable under acidic conditions but can hydrolyze in alkaline environments. The compound plays a significant role in pharmaceutical applications, particularly in the development of semi-synthetic penicillins, which are designed to enhance antibacterial efficacy and broaden the spectrum of activity against resistant bacterial strains. Due to its importance in antibiotic production, 6-APA is a key focus in medicinal chemistry and pharmaceutical research.

Formula: C₈H₁₂N₂O₃S

InChI: 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: InChIKey=NGHVIOIJCVXTGV-ALEPSDHESA-N

SMILES: C(O)(=O)[C@@H]1N2[C@@]([C@H](N)C2=O)(SC1(C)C)[H]

Synonyms:

• (2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-amino-3,3-dimethyl-7-oxo-
• 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-amino-3,3-dimethyl-7-oxo-, (2S,5R,6R)-
• 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-amino-3,3-dimethyl-7-oxo-, [2S-(2alpha,5alpha,6beta)]-
• 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-amino-3,3-dimethyl-7-oxo-, [2S-(2α,5α,6β)]-
• 6-Amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• 6-Aminopencillanic acid
• 6-Aminopenicillansaure
• 6-Apa
• 6-Aps
• 6β-Aminopenicillanic acid
• Acide 6-aminopenicillanique
• Acido 6-Aminopenicilanico
• Aminopenicillanic Acid
• Nsc 50071
• Penicillanic Acid, 6-Amino-
• Phenacyl 6-aminopenicillinate

6-Aminopenicillanic Acid

CAS: 551-16-6

Formula: C₈H₁₂N₂O₃S

Purity: >98.0%(HPLC)

Color and Shape: White to Light yellow to Dark green powder to crystal

Molecular weight: 216.26

Ref: 3B-A0800

Amoxicillin EP Impurity A (Piperacillin EP Impurity H, Sulbactam EP Impurity B)

CAS: 551-16-6

Formula: C8H12N2O3S

Purity: +90%

Molecular weight: 216.26

Ref: ZB-AMXL-A

FLUCLOXACILLIN IMPURITY C CRS

CAS: 551-16-6

FLUCLOXACILLIN IMPURITY C CRS

Formula: C₈H₁₂N₂O₃S

Molecular weight: 216.2575

Ref: 41-Y0000889

Amoxicillin Related Compound A ((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

Nucleic acids and their salts, whether or not chemically defined; other heterocyclic compounds, nesoi

Formula: C₈H₁₂N₂O₃S

Color and Shape: White Cream Powder

Molecular weight: 216.05686

Ref: 45-1031514

6-Aminopenicillanic acid

CAS: 551-16-6

Formula: C₈H₁₂N₂O₃S

Purity: 95%

Color and Shape: Solid

Molecular weight: 216.2575

Ref: IN-DA0034BO

Amoxicillin EP Impurity A (Sulbactam EP Impurity B, Piperacillin EP Impurity H, Amoxicillin USP Related Compound A)

CAS: 551-16-6

Formula: C₈H₁₂N₂O₃S

Color and Shape: White To Off-White Solid

Molecular weight: 216.26

Ref: 4Z-A-233

6-Aminopenicillanic acid

CAS: 551-16-6

Compound PDK0270, with CAS No. 551-16-6, is a fragment molecule that serves as an important scaffold for molecular linking, expansion, and modification. Compound PDK0270 provides a structural basis and research tool for the design and screening of novel drug candidates, and is commonly used in drug discovery, drug synthesis, and related research.

Formula: C₈H₁₂N₂O₃S

Color and Shape: Off White Powder Solid Powder

Molecular weight: 216.257

Ref: TM-PDK0270

6-Aminopenicillanic acid

CAS: 551-16-6

Formula: C₈H₁₂N₂O₃S

Purity: 97.0 - 103.0 %

Color and Shape: White to off-white powder

Molecular weight: 216.26

Ref: 7W-GA3817

(2S,5R,6R)-6-Amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid (6-Aminopenicillanic Acid)

Controlled Product

CAS: 551-16-6

Formula: C₈H₁₂N₂O₃S

Color and Shape: Neat

Molecular weight: 216.26

Ref: 86-MM0026.04

(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

(2S,5R,6R)-(+)-6-Amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

Formula: C₈H₁₂N₂O₃S

Purity: 95%

Color and Shape: white solid

Molecular weight: 216.26g/mol

Ref: 54-OR28860

Amoxicillin (2R)-Piperazine-2,5-dione

CAS: 551-16-6

Formula: C₁₆H₁₉N₃O₅S

Molecular weight: 365.40

Ref: 4Z-A-2337

Ampicillin EP Impurity A

CAS: 551-16-6

Formula: C₈H₁₂N₂O₃S

Molecular weight: 216.3

Ref: ST-EA-CP-A59030

Amoxicillin EP Impurity A

CAS: 551-16-6

Formula: C₈H₁₂N₂O₃S

Molecular weight: 216.26

Ref: ST-EA-CP-A20001

(+)-6-Aminopenicillanic Acid

CAS: 551-16-6

Impurity Ampicillin EP Impurity A ; Amoxicillin USP Related Compound A
Applications (+)-6-Aminopenicillanic Acid (Amoxicillin EP Impurity A) 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.
References Zel'tser, I.Z. et al.: Gig. Truda Prof. Zabol., 5, 59 (1983); Hamilton-Miller, J.M.T.: Int. J. Antimicrob. Agents, 31, 189 (2008); Novikova, N.D. et al.: Mikol. Fitopatol., 7, 101 (1973);

Formula: C₈H₁₂N₂O₃S

Color and Shape: Off-White

Molecular weight: 216.26

Ref: TR-A618895

(2S,5R,6R)-6-Amino-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid

CAS: 551-16-6

Formula: C₈H₁₂N₂O₃S

Purity: 95.0%

Color and Shape: Solid, Beige powder

Molecular weight: 216.26

Ref: 10-F057763

(+)-6-Aminopenicillanic Acid-d3

Controlled Product

CAS: 551-16-6

Formula: C₈D₃H₉N₂O₃S

Color and Shape: Neat

Molecular weight: 219.276

Ref: TR-A618897

6-Aminopenicillanic acid

CAS: 551-16-6

6-Aminopenicillanic acid, also known as 6-APA, is a penicillin antibiotic that inhibits bacterial cell wall synthesis and protein synthesis by interfering with the formation of peptidoglycan cross-links in bacterial cell walls. 6-APA has been shown to have low potency against many strains of bacteria. It is used in wastewater treatment and has been shown to inhibit nitrogen atoms from entering the environment. The enzyme activity of 6-APA is increased when it reacts with complex enzymes. This compound binds to penicillin-binding proteins on the surface of bacterial cells and inhibits their growth. The antimicrobial properties of 6-APA are due to its ability to inhibit cell wall synthesis, protein synthesis and other metabolic reactions.

Formula: C₈H₁₂N₂O₃S

Purity: Min. 95%

Color and Shape: White Powder

Molecular weight: 216.26 g/mol

Ref: 3D-FA36389