Premium
Zur Kenntnis der Benzylpenicilloinsäure
Author(s) -
Schneider C. H.,
De Weck A. L.
Publication year - 1967
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19670500734
Subject(s) - chemistry , benzylpenicillin , caproic acid , alkali metal , hydrolysis , molar ratio , alkaline hydrolysis , ethylene diamine , organic chemistry , penicillin , nuclear chemistry , biochemistry , catalysis , antibiotics
The molar penamaldate value of benzylpenicilloic acid and the influence of large amounts of benzylpenicillin on the estimation of penamaldate values and penamaldate stabilities of benzylpenicilloic acid and ε‐(benzylpenicilloyl‐α‐amido)‐caproic acid have been determined. The molar penamaldate values of purified benzylpenicilloate and of benzylpenicillin hydrolyzed in alkali were equal, indicating that benzylpenicillin upon alkaline hydrolysis is converted to penicilloic acid exclusively, with no side reactions occurring to any considerable degree. Benzylpenicilloate mutarotates in neutral solution as well as in alkali, the reaction being unaffected by metal ion complexing with ethylene diamine tetraacetate. ε‐(Benzylpenicilloyl‐α‐amido)‐caproate also mutarotates in alkali; no mutarotation occurs however in neutral solution. Different mechanisms of epimerisation have therefore to be considered for the mutarotations of penicilloates and of α‐amides of penicilloic acid respectively.