22252-43-3

Basic information

• Product Name: 7-Amino-3-methyl-3-cephem-4-carboxylic acid
• Synonyms: 7-amino-3-methyl-3-cephem-4-carboxylic;ADCA;7-Aminodezacetoxycephalosporanic acid;7-Amino deacetoxy cefalosporanic acid;7-Amino-3-desacetoxy cephalosporanic acid;6R,7R)-7-Amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid;7-Amino-3-deacetoxycephalosporanic Acid;Deacetoxycephalosporanic Acid
• CAS NO: 22252-43-3
• Molecular Formula: C₈H₁₀N₂O₃S
• Molecular Weight: 214.24
• EINECS: 244-870-1
• Product Categories: Various Metabolites and Impurities;Antibiotics for Research and Experimental Use;beta-Lactams (Antibiotics for Research and Experimental Use);Biochemistry;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Metabolites & Impurities, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 22252-43-3.mol
• Article Data: 16

Chemical Properties

• Melting Point: 234°C (dec.)
• Boiling Point: 517.6 °C at 760 mmHg
• Flash Point: 266.8 °C
• Appearance: off-white powder
• Density: 1.59 g/cm³
• Vapor Pressure: 4.18E-12mmHg at 25°C
• Refractive Index: 104 ° (C=1, 1mol/L HCl)
• Storage Temp.: 2-8°C
• Solubility: Do you have solubility information on this product that you woul
• PKA: 3.04±0.50(Predicted)
• Water Solubility: Soluble in water (partly), 1M ammonium hydroxide (50 mg/ml), and DMSO (Sparingly).
• Stability: Stable. Incompatible with strong oxidizing agents.
• BRN: 5273616
• CAS DataBase Reference: 7-Amino-3-methyl-3-cephem-4-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 7-Amino-3-methyl-3-cephem-4-carboxylic acid(22252-43-3)
• EPA Substance Registry System: 7-Amino-3-methyl-3-cephem-4-carboxylic acid(22252-43-3)

Safety Data

• Hazard Codes: Xn
• Statements: 42/43-36/37/38-20/21/22
• Safety Statements: 36-26
• WGK Germany: 3
• Hazardous Substances Data: 22252-43-3(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Powder

Uses

Different sources of media describe the Uses of 22252-43-3 differently. You can refer to the following data:
1. A metabolite of Cephalexin (C256800).
2. 7-Aminodesacetoxycephalosporanic acid is the Cephalexin metabolite. It is a Potent inhibitor of bacterial cell-wall enzyme. It is used in the synthesis of cephalosporins and for bioconversion studies.

Definition

ChEBI: A cephem monocarboxylic acid derivative having a structure based on cephalosporanic acid, deacetoxylated and carrying a 7beta-amino group.

InChI:InChI=1/C8H10N2O3S/c1-3-2-14-7-4(9)6(11)10(7)5(3)8(12)13/h4,7H,2,9H2,1H3,(H,12,13)/t4-,7-/m0/s1

Upstream product

• 957-68-6 7-Aminocephalosporanic acid 
• 4888-90-8 phenoxymethylpenicillin sulfoxide 
• 983-85-7 Maripen 
• 72005-99-3 (6R)-3-methyl-8-oxo-7t-(2,2,2-trifluoro-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 
• 101-02-0 triphenyl phosphite 
• 75-36-5 acetyl chloride 
• 87-69-4 tartaric acid 
• 855904-39-1 N-ethyl-N-hexadecylaniline 
• 80154-48-9 (6R,7R)-1-aza-3-methyl-7-(m-carboxypentanamido)-8-oxo-5-thiabicyclo<4.2.0>oct-2-ene carboxylic acid 
• 15686-71-2 cefalexin 
• 28180-80-5 (6R,7R)-2,2,2-trichloroethyl 3-methyl-7-phenylacetamidoceph-3-em-4-carboxylate 
• 72005-98-2 (6R)-3-methyl-8-oxo-7t-(2,2,2-trifluoro-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 2,2,2-trichloro-ethyl ester 
• 53982-53-9 acetoxymethyl 6β-phenylacetamidopenicillanate 1-oxide 
• 81244-83-9 acetoxymethyl 6-(phenoxyacetamido)-penicillanate 1-oxide 

Downstream Products

• 76273-08-0 7-tosyloxyacetamido-3-deacetoxycephalosporanic acid 
• 73707-50-3 C₁₅H₁₃N₂O₃S₂^(1-)*Na⁽¹⁺⁾ 
• 143407-73-2 Sodium; (6R,7R)-7-{[1-(4-chloro-phenyl)-cyclopentanecarbonyl]-amino}-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylate 
• 130677-47-3 (6R,7R)-7-{2-[(E)-Methoxyimino]-3-[1-phenyl-meth-(E)-ylideneaminooxy]-propionylamino}-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 
• 130677-49-5 (6R,7R)-7-{2-[(E)-Methoxyimino]-3-[1-phenyl-eth-(E)-ylideneaminooxy]-propionylamino}-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 
• 130677-51-9 (6R,7R)-7-{2-[(E)-Methoxyimino]-3-[1-(2-methoxy-phenyl)-meth-(E)-ylideneaminooxy]-propionylamino}-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 
• 130677-57-5 (6R,7R)-7-{3-[1-(4-Chloro-phenyl)-meth-(E)-ylideneaminooxy]-2-[(E)-methoxyimino]-propionylamino}-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 
• 130677-53-1 (6R,7R)-7-{2-[(E)-Methoxyimino]-3-[1-(4-methoxy-phenyl)-meth-(E)-ylideneaminooxy]-propionylamino}-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 
• 130677-55-3 (6R,7R)-7-{2-[(E)-Methoxyimino]-3-[1-(4-methoxy-phenyl)-eth-(E)-ylideneaminooxy]-propionylamino}-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 
• 125186-57-4 (6R,7R)-7-[2-(2-Methoxycarbonyl-phenoxy)-acetylamino]-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 
• 125186-58-5 (6R,7R)-7-[2-Ethyl-2-(2-methoxycarbonyl-phenoxy)-butyrylamino]-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 
• 125205-62-1 (6R,7R)-7-[2-Ethyl-2-(2-methoxycarbonyl-phenoxy)-3-methyl-butyrylamino]-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 
• 125186-59-6 (6R,7R)-7-[2-(2-Methoxycarbonyl-phenoxy)-2-propyl-pentanoylamino]-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 
• 125186-60-9 (6R,7R)-7-[2-(2-Methoxycarbonyl-phenoxy)-2-propyl-hexanoylamino]-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 

Relevant articles and documents

On the substrate preference of glutaryl acylases

The substrate preferences of three acylases - two wild-type enzymes and an evolved variant obtained by directed evolution - which are prototypical enzymes for glutaryl-7-ACA acylase and cephalosporin C acylase subfamilies, have been investigated. A preliminary screening of enzymes' performances on a large set of substrates has been carried out by a colorimetric assay performed in 96-well plates and by a pH-Stat monitoring the hydrolytic activities. Subsequently, kinetic data for selected substrates have been determined, thus elucidating the substrate preference of members of glutaryl-7-ACA acylase vs. cephalosporin C acylase subfamilies. These achievements pave the way to the ability of choosing the best enzyme for the hydrolysis of different compounds of industrial importance.

PROCESS FOR THE PRODUCTION OF CEPHALOSPORINS

The present invention relates to a composition comprising ≥85 wt% of an N-deacylated cephalosporin, a process for making the same and the use of said N-deacylated cephalosporin in the preparation of highly pure semi synthetic cephalosporins.

Glutaryl Acylases: One-Reaction Enzymes or Versatile Enantioselective Biocatalysts?

A significant broad substrate specificity, that crosses over the usual β-lactam derivatives, has been observed with an industrial glutaryl-7-aminocephalosporanic acid acylase (GA). This enzyme possesses significant enantioselective amidase and even esterase activity, with a stereopreference for the S-enantiomer. The easy separation of products from unreacted reagents, possessing different physical-chemical properties, is achieved by solvent extraction, avoiding chromatography or distillation during reaction work-up.