Shandong Huashang Chemical Co., Ltd. is a high-tech enterprise specializing in the research and development, manufacturing, and sales of fine chemicals. Headquartered in Jinan, Shandong, China, we are committed to delivering high-quality products to our global partners. Currently, over 90% of our products are exported to developed markets, including North America, Europe, Japan, South Korea, and the Middle East.
Product Description
7-Aminocephalosporanic acid (CAS: 957-68-6), commonly known as 7-ACA, is a critical β-lactam antibiotic intermediate with the molecular formula C??H??N?O?S. It appears as a white to off-white crystalline powder at room temperature, odorless, and slightly hygroscopic. The compound is sparingly soluble in water (409.6 mg/L at 25 °C) and soluble in dilute alkaline solutions (e.g., NaOH, KOH) and polar aprotic solvents like DMSO. It is primarily produced by enzymatic hydrolysis or chemical cleavage of cephalosporin C, featuring a fused β-lactam-dihydrothiazine ring system with reactive amino (7-position) and carboxyl (2-position) groups. As the core mother nucleus for semi-synthetic cephalosporins, it serves as a foundational building block for manufacturing a wide range of clinically vital antibiotics, underpinning modern pharmaceutical production for bacterial infection treatments.
Uses
Cephalosporin Antibiotic Intermediate: Exclusive primary application as the key starting material for synthesizing semi-synthetic cephalosporin antibiotics. Structural modifications at the 7-amino and 3-acetoxymethyl positions yield diverse broad-spectrum antibiotics, including Cefotaxime, Cefazolin, Ceftriaxone, Cefuroxime, and Cefepime, which are widely used in clinical settings to treat severe bacterial infections (e.g., respiratory tract, urinary tract, and sepsis).
Pharmaceutical Research & Development: Utilized as a reference standard and synthetic intermediate in β-lactam antibiotic research, supporting the development of novel cephalosporin derivatives with enhanced potency, extended spectrum, and resistance to β-lactamase enzymes. It also serves as a key tool for studying antibiotic structure-activity relationships (SAR) and mechanisms of bacterial resistance.
Biochemical Reagent: Employed in biochemical assays and microbiological studies as a substrate for β-lactamase inhibition tests and microbial susceptibility screenings. It is also used in cell culture and in vitro antimicrobial activity evaluations, supporting pharmaceutical quality control and biological research applications.
Other Applications: Used in the synthesis of β-lactamase inhibitors and related pharmaceutical fine chemicals. Its unique ring structure and reactive functional groups enable specific chemical transformations (e.g., acylation, alkylation) for producing specialized pharmaceutical intermediates and research reagents.
Molecular Formula & Structure
- Molecular Formula: C??H??N?O?S
- Molecular Weight: 272.28 g/mol (272.0467 g·mol?1, precise value)
- IUPAC Name: (6R,7R)-7-Amino-3-(acetoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- Synonyms: 7-ACA; 7-Aminocephalosporanic acid; 7-Aminocephalosporanic acid; 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[(acetyloxy)methyl]-7-amino-8-oxo-, (6R,7R)-; MFCD00005177; BRN 622637; PubChem Substance ID: 24851470; EC Number: 213-485-0
- EC Number: 213-485-0
- CAS Number: 957-68-6
- SMILES Code: CC(=O)OCC1=C(N2[C@H]([C@@H](N)C2=O)S1)C(=O)O
- Chemical Structure: The molecule features a fused bicyclic system: a four-membered β-lactam ring (azetidinone) fused to a six-membered dihydrothiazine ring. Key functional groups include a primary amino group (-NH?) at the 7-position (β-lactam ring), a carboxyl group (-COOH) at the 2-position (dihydrothiazine ring), and an acetoxymethyl group (-CH?OCOCH?) at the 3-position. The (6R,7R) stereochemistry is critical for biological activity, as it enables binding to bacterial penicillin-binding proteins (PBPs) and inhibiting cell wall synthesis.
Physical & Chemical Properties
- Appearance: White to off-white crystalline powder; odorless; fine crystalline texture; no visible impurities; slightly hygroscopic.
- Melting Point: >300 °C (decomposition before melting); Boiling Point: Not applicable (decomposes at high temperature); Specific Rotation: [α]1?/D +90° (c = 0.5 in KH?PO?/trace NaOH); Thermal Stability: Decomposes above 200 °C, releasing toxic fumes (NO?, SO?).
- Density: 1.65 ± 0.1 g/cm3 (25 °C); Refractive Index: n??/D 1.565 (estimated); Solubility: 409.6 mg/L in water (25 °C); soluble in dilute alkaline solutions (pH > 8), DMSO, and DMF; insoluble in ethanol, methanol, acetone, toluene, and hexane.
- Stability: Stable under dry, cold (2–8 °C) conditions; sensitive to moisture, high temperature (>30 °C), and strong alkaline environments (pH > 9), which cause hydrolysis of the β-lactam ring and degradation. Avoid exposure to direct sunlight and oxidizing agents; incompatible with strong acids, strong bases, and heavy metal ions (e.g., Cu2?, Fe3?) that accelerate decomposition.
- Toxicity: Low acute oral toxicity (LD?? > 5000 mg/kg in rats); may cause skin sensitization and eye irritation (H317, H319); inhalation of dust may cause respiratory irritation or allergic reactions. GHS Labeling: Signal word "Warning"; Hazard statements H317 (May cause an allergic skin reaction), H319 (Causes serious eye irritation); Precautionary statements P261, P264, P272, P280, P302+P352, P305+P351+P338, P333+P313, P337+P313, P501.
Synthesis & Storage
- Synthesis: Industrial production primarily uses two methods: (1) Enzymatic Hydrolysis: Cephalosporin C (from fermentation) is hydrolyzed by genetically engineered CPC acylase under mild conditions (pH 7–8, 25–30 °C), yielding high-purity 7-ACA with high selectivity and low environmental impact. (2) Chemical Cleavage: Cephalosporin C undergoes deacylation via chemical reagents (e.g., nitrosyl chloride, phosphorus pentachloride) under low-temperature (-20 to 0 °C) anhydrous conditions, followed by neutralization and crystallization. The crude product is purified by recrystallization from water/ethanol mixtures to obtain high-purity (≥99.0%) crystalline powder.
- Storage: Store in a cool, dry, well-ventilated warehouse at 2–8 °C; keep containers tightly sealed to prevent moisture absorption and degradation. Packaged in food-grade polyethylene bags (net weight 25 kg/bag) or aluminum foil bags (1 kg/bag) inside fiber drums. Avoid direct sunlight, high temperature (>30 °C), and humid environments; store separately from strong acids, strong bases, oxidizing agents, and food materials. Shelf life: 24 months when unopened and stored properly; use promptly after opening to prevent moisture-induced degradation.
- Safety: Operate in a well-ventilated fume hood; wear nitrile gloves, safety goggles, and dust mask during handling to avoid skin, eye, and respiratory contact. In case of skin contact, rinse with plenty of water for 15 minutes; in case of eye contact, rinse with water for several minutes and seek medical attention. In case of inhalation, move to fresh air and seek medical advice if symptoms persist. Dispose of waste and contaminated containers in accordance with hazardous waste regulations; do not release into the environment.
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