N. Vasilyeva, A. S. Kazachenko, Y. Malyar, B. Kuznetsov
{"title":"Sulfation of Betulin with Chlorosulfonic Acid in Pyridine","authors":"N. Vasilyeva, A. S. Kazachenko, Y. Malyar, B. Kuznetsov","doi":"10.17516/1998-2836-0197","DOIUrl":null,"url":null,"abstract":"It was found that when betulin is sulfated with chlorosulfonic acid in pyridine medium, 3,28-disulfate of betulin is formed in a stable salt form. Under optimal synthesis conditions: temperature 70 °C, duration 2 hours, molar ratio betulin / chlorosulfonic acid 4.0, betulin is completely converted into betulin 3.28-disulfate. The structure and composition of betulin 3,28-disulfate were confirmed by elemental analysis, IR, Raman and 13C NMR spectroscopy. Betulin 3,28-disulfate was isolated both in the form of an unstable H + -form and in a stable forms of sodium and pyridinium salts. Sodium salt of 3,28-disulfate is a needle-like crystals collected in cobweb-like aggregates. The sodium salt of 3,28-disulfate has mycellar properties, the critical concentration of mycellar formation is 0.23 mmol / L.","PeriodicalId":16999,"journal":{"name":"Journal of Siberian Federal University. Chemistry","volume":"7 1","pages":""},"PeriodicalIF":0.5000,"publicationDate":"2020-09-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"5","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Siberian Federal University. Chemistry","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.17516/1998-2836-0197","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 5
Abstract
It was found that when betulin is sulfated with chlorosulfonic acid in pyridine medium, 3,28-disulfate of betulin is formed in a stable salt form. Under optimal synthesis conditions: temperature 70 °C, duration 2 hours, molar ratio betulin / chlorosulfonic acid 4.0, betulin is completely converted into betulin 3.28-disulfate. The structure and composition of betulin 3,28-disulfate were confirmed by elemental analysis, IR, Raman and 13C NMR spectroscopy. Betulin 3,28-disulfate was isolated both in the form of an unstable H + -form and in a stable forms of sodium and pyridinium salts. Sodium salt of 3,28-disulfate is a needle-like crystals collected in cobweb-like aggregates. The sodium salt of 3,28-disulfate has mycellar properties, the critical concentration of mycellar formation is 0.23 mmol / L.
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