7-Aminocephalosporanic acidCAS# 957-68-6 |
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Quality Control & MSDS
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| Cas No. | 957-68-6 | SDF | Download SDF |
| PubChem ID | 441328 | Appearance | Powder |
| Formula | C10H12N2O5S | M.Wt | 272.28 |
| Type of Compound | N/A | Storage | Desiccate at -20°C |
| Synonyms | 7-ACA | ||
| Solubility | DMSO : < 1 mg/mL (insoluble or slightly soluble) H2O : < 0.1 mg/mL (insoluble) | ||
| Chemical Name | (6R,7R)-3-(acetyloxymethyl)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid | ||
| SMILES | CC(=O)OCC1=C(N2[C@H](SC1)[C@H](N)C2=O)C(O)=O | ||
| Standard InChIKey | HSHGZXNAXBPPDL-HZGVNTEJSA-N | ||
| Standard InChI | InChI=1S/C10H12N2O5S/c1-4(13)17-2-5-3-18-9-6(11)8(14)12(9)7(5)10(15)16/h6,9H,2-3,11H2,1H3,(H,15,16)/t6-,9-/m1/s1 | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | 7-Aminocephalosporanic acid is the core chemical structure for the synthesis of cephalosporin antibiotics, is a potent β-lactamase inhibitor. |
7-Aminocephalosporanic acid Dilution Calculator
7-Aminocephalosporanic acid Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 3.6727 mL | 18.3634 mL | 36.7269 mL | 73.4538 mL | 91.8172 mL |
| 5 mM | 0.7345 mL | 3.6727 mL | 7.3454 mL | 14.6908 mL | 18.3634 mL |
| 10 mM | 0.3673 mL | 1.8363 mL | 3.6727 mL | 7.3454 mL | 9.1817 mL |
| 50 mM | 0.0735 mL | 0.3673 mL | 0.7345 mL | 1.4691 mL | 1.8363 mL |
| 100 mM | 0.0367 mL | 0.1836 mL | 0.3673 mL | 0.7345 mL | 0.9182 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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7-Aminocephalosporanic acid is used for synthesis of cephalosporin antibiotics and intermediates.
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Possibilities to acylate 7-aminocephalosporanic acid to obtain some cephalosporins.[Pubmed:24741808]
Rev Med Chir Soc Med Nat Iasi. 2014 Jan-Mar;118(1):244-9.
AIM: Acylation of 7-Aminocephalosporanic acid with an adequate acyl chloride in order to obtain cefotaxime sodium salt. MATERIAL AND METHODS: Cefotaxime sodium salt was synthesized by acylating 7-amino cephalosporanic acid with 2-[2'-chloracetamidothiazole-4-yl]-2-(syn)-methoxy-imino acetic chloride in four steps. The melting point was determined, and IR spectral analysis and elemental analysis were performed to confirm cefotaxime structure. The quantitative determination was performed. RESULTS: The reaction conditions were established. The yield of the synthesis phases (73-80%) and actual yield (45-47%) were very good. The structure of the obtained cefotaxime sodium salt was confirmed by the IR spectral analysis and by elemental analysis (C, H, N). The melting point was 163 degrees C. The purity of the synthesized cefotaxime sodium salt was 98.9%. CONCLUSIONS: Cefotaxime sodium salt was synthesized by acylation of 7-Aminocephalosporanic acid with 2-[2'-chloracetamidothiazole-4-yl]-2-(syn)-methoxy-imino acetic chloride, in aqueous solution, then transformed into sodium salt with sodium 2-ethylhexanoate. The method proved to be very good, yields were good, it is reproducible and simple, and does not involve high risks, so it is also safe.
Penicillin acylase-catalyzed synthesis of N-bromoacetyl-7-aminocephalosporanic acid, the key intermediate for the production of cefathiamidine.[Pubmed:27917366]
Bioresour Bioprocess. 2016;3(1):49.
BACKGROUND: Enzymatic approaches have become promising alternatives to chemical methods for the production of semi-synthetic beta-lactam antibiotics. In this work, enzymatic synthesis of N-bromoacetyl-7-Aminocephalosporanic acid (N-bromoacetyl-7-ACA), the key intermediate for the production of cefathiamidine, was reported for the first time. RESULTS: Of the immobilized penicillin acylases (PAs) tested, PGA-750 was the best biocatalyst. Optimization of the biocatalytic process was conducted. The optimal acyl donor, molar ratio of acyl donor to 7-ACA, pH, temperature, 7-ACA concentration, and enzyme dosage were methyl bromoacetate, 3, 7.5, 20 degrees C, 50 mmol/L and 4 U/mL, respectively. Under the optimal conditions, enzymatic N-acylation of 7-ACA with methyl bromoacetate afforded the desired product with the yield of 85% in 2 h, where the synthesis/hydrolysis (S/H) ratio was approximately 1.5. The immobilized enzyme PGA-750 exhibited good operational stability, and the relative yields of approximately 90% and 63% were achieved, respectively, when it was reused in 7th and 11th batch. CONCLUSIONS: An enzymatic approach to N-bromoacetyl-7-ACA, the key intermediate for the industrial production of cefathiamidine, has been developed successfully in a fully aqueous medium. The present work may open up a novel opportunity for the production of cefathiamidine through a simple and green process.Graphical abstractEnzymatic synthesis of N-bromoacetyl-7-ACA, the key intermediate for the production of cefathiamidine, was reported for the first time.
Identification and Characterization of a New 7-Aminocephalosporanic Acid Deacetylase from Thermophilic Bacterium Alicyclobacillus tengchongensis.[Pubmed:26527640]
J Bacteriol. 2015 Nov 2;198(2):311-20.
UNLABELLED: Deacetylation of 7-Aminocephalosporanic acid (7-ACA) at position C-3 provides valuable starting material for producing semisynthetic beta-lactam antibiotics. However, few enzymes have been characterized in this process before now. Comparative analysis of the genome of the thermophilic bacterium Alicyclobacillus tengchongensis revealed a hypothetical protein (EstD1) with typical esterase features. The EstD1 protein was functionally cloned, expressed, and purified from Escherichia coli BL21(DE3). It indeed displayed esterase activity, with optimal activity at around 65 degrees C and pH 8.5, with a preference for esters with short-chain acyl esters (C2 to C4). Sequence alignment revealed that EstD1 is an SGNH hydrolase with the putative catalytic triad Ser15, Asp191, and His194, which belongs to carbohydrate esterase family 12. EstD1 can hydrolyze acetate at the C-3 position of 7-Aminocephalosporanic acid (7-ACA) to form deacetyl-7-ACA, which is an important starting material for producing semisynthetic beta-lactam antibiotics. EstD1 retained more than 50% of its initial activity when incubated at pH values ranging from 4 to 11 at 65 degrees C for 1 h. To the best of our knowledge, this enzyme is a new SGNH hydrolase identified from thermophiles that is able to hydrolyze 7-ACA. IMPORTANCE: Deacetyl cephalosporins are highly valuable building blocks for the industrial production of various kinds of semisynthetic beta-lactam antibiotics. These compounds are derived mainly from 7-ACA, which is obtained by chemical or enzymatic processes from cephalosporin C. Enzymatic transformation of 7-ACA is the main method because of the adverse effects chemical deacylation brought to the environment. SGNH hydrolases are widely distributed in plants. However, the tools for identifying and characterizing SGNH hydrolases from bacteria, especially from thermophiles, are rather limited. Here, our work demonstrates that EstD1 belongs to the SGNH family and can hydrolyze acetate at the C-3 position of 7-ACA. Moreover, this study can enrich our understanding of the functions of these enzymes from this family.
Characterization of cross-linked immobilized arylesterase from Gluconobacter oxydans 621H with activity toward cephalosporin C and 7-aminocephalosporanic acid.[Pubmed:26443058]
Biotechnol Prog. 2016 Jan-Feb;32(1):36-42.
Cross-linked enzyme aggregates (CLEAs) were prepared from several precipitant agents using glutaraldehyde as a cross-linking agent with and without BSA, finally choosing a 40% saturation of ammonium sulfate and 25 mM of glutaraldehyde. The CLEAs obtained under optimum conditions were biochemically characterized. The immobilized enzyme showed higher thermal activity and a broader range of pH and organic solvent tolerance than the free enzyme. Arylesterase from Gluconobacter oxydans showed activity toward cephalosporin C and 7-Aminocephalosporanic acid. The CLEAs had a Kcat/KM of 0.9 M(-1) /S(-1) for 7-ACA (7-Aminocephalosporanic acid) and 0.1 M(-1) /S(-1) for CPC (cephalosporin c), whereas free enzyme did not show a typical Michaelis-Menten kinetics.
