Sulfation of Betulin with Chlorosulfonic Acid in Pyridine

IF 0.5 Q4 CHEMISTRY, MULTIDISCIPLINARY Journal of Siberian Federal University. Chemistry Pub Date : 2020-09-01 DOI:10.17516/1998-2836-0197
N. Vasilyeva, A. S. Kazachenko, Y. Malyar, B. Kuznetsov
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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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吡啶中白桦林与氯磺酸的磺化反应
结果表明,在吡啶介质中,用氯磺酸对桦木素进行磺化处理,可形成以稳定盐形态存在的3,28-二硫酸盐。在最佳合成条件下:温度70℃,持续时间2小时,桦木素/氯磺酸的摩尔比为4.0,桦木素完全转化为桦木素3.28-二硫酸盐。通过元素分析、红外光谱、拉曼光谱和13C核磁共振光谱等手段,确定了桦木素3,28-二磺酸盐的结构和组成。桦木素3,28-二硫酸酯既以不稳定的H +形式分离,又以稳定的钠盐和吡啶盐形式分离。3,28-二硫酸钠是一种针状晶体,呈蛛网状聚集。3,28-二硫酸钠具有mycellar特性,mycellar形成的临界浓度为0.23 mmol / L。
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CiteScore
1.10
自引率
0.00%
发文量
13
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