Abstract
IN the course of investigations on the constitution of the quaternary base chaksine, C11H21O3N3OH, isolated from Cassia absus, Linn.1, pyrolytic degradation of its iodide has been studied. On pyrolysis with silver or copper filings, at 310–320° C., in a nitrogen atmosphere, it gave ammonia, carbon dioxide and an oily product of deep red colour and soluble in ether, with a strong caraway-like smell, in about 10 per cent yield. This product on boiling with 20 per cent methanolic potassium hydroxide for 12 hr. yielded an acid soluble in petrol-ether (60°–80° C.) (melting point, 116°C. dec.) and an oily phenolic fraction soluble in petrol-ether. On using electrolytic copper in place of silver or copper filings in this degradation, the resulting ether-soluble oily product gave on hydrolysis, under the conditions described above, no acid soluble in petroleum ether but a much larger yield of the acid melting at 195° C. (dec.), which was identified as phthalic acid, finally through its anhydride. Accounting as it does for 8 out of 11 or possibly 12 carbon atoms of chaksine1, this finding marks a significant stage in the elucidation of its constitution.
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Siddiqui, S., and Ahmad, Z., Proc. Ind. Acad. Sci., 2A, 421 (1935). Puri, V. N., Sharma, V. N., and Siddiqui, S., J. Sci. and Ind. Res. (India), 4 (11), 701 (1946). Kapur, Gaind, Narang and Ray, J. Ind. Chem. Soc., 17, 281 (1940).
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SIDDIQUI, S., HAHN, G., SHARMA, V. et al. Constitution of Chaksine. Nature 178, 373 (1956). https://doi.org/10.1038/178373a0
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DOI: https://doi.org/10.1038/178373a0
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