7-Amino-3-methyl-3-cephem-4-carboxylic acid Chemical Properties

Melting point:

234°C (dec.)

Boiling point:

517.6±50.0 °C(Predicted)

Density 

1.59±0.1 g/cm3(Predicted)

vapor pressure 

0Pa at 20℃

refractive index 

104 ° (C=1, 1mol/L HCl)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

3.04±0.50(Predicted)

form 

powder

color 

White to Orange to Green

Water Solubility 

Soluble in water (partly), 1M ammonium hydroxide (50 mg/ml), and DMSO (Sparingly).

BRN 

5273616

Stability:

Stable. Incompatible with strong oxidizing agents.

InChI

InChI=1S/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-/m1/s1

InChIKey

NVIAYEIXYQCDAN-CLZZGJSISA-N

SMILES

N12[C@@]([H])([C@H](N)C1=O)SCC(C)=C2C(O)=O

LogP

-3.8--2.8 at 20℃ and pH3.6-7

CAS DataBase Reference

22252-43-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

42/43-36/37/38-20/21/22

Safety Statements 

36-26

WGK Germany 

3

HS Code 

2941901010

Storage Class

11 - Combustible Solids

Hazard Classifications

Aquatic Chronic 3

7-Amino-3-methyl-3-cephem-4-carboxylic acid Usage And Synthesis

Chemical Properties

Off-White Powder

Uses

A metabolite of Cephalexin (C256800).

Uses

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.

Biological Activity

7-ADCA is produced from penicillin G made by Penicillium chrysogenum involving several polluting chemical steps followed by enzymatic deacylation using penicillin acylase .

Synthesis

The existing preparation method usually employs acylase to cleave 7-phenylacetamidocephalosporanic acid, and then obtains 7-ADCA by acidification, dichloromethane extraction to remove impurities, activated charcoal decolorization and crystallization, etc. However, in this process, after obtaining the cleavage solution, the steps of removing impurities and decoloration are more cumbersome, and after decoloration with activated charcoal, in the subsequent reaction process, some of the substances come into contact with oxygen in the air, and are prone to appear color again, and the effect of removing impurities and decolorization is poor.

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