Sceleranecic acid

Sauroxine saururine, 753, 7S4 Saussufea Cappa saussurine, 782 Sceleranecic acid, 605 Sceleratlne, 602, 605 Schcenocaulon officinale, 700 Scopine, 64, 66, 88, 107 -scopine, 89 ncr-0-scopine, 89 Scopolamine, see Hyoscine ... 

Related in structure to sceleranecic acid (sceleranecic dilactone) is sceleratinic acid (sceleratinic dilactone), C10H13CIO4, found by de Waal and Louw (129) in Senecio scderatus but apparently not a portion of an alkaloid. It was also obtained by de Waal et al. (132) by treatment of the potassium salt of sceleranecic acid with thionyl chloride or phosphorus pentachloride. On neutralization of sceleratinic dilactone (v ax. cm. ) with alkali, the compound behaved similarly to sceleranecic lactone, from which it was concluded that the two compounds possess the same dilactone structure. Moreover, oxidation of sceleratinic acid, potassium salt, yielded the same C8H12O4 monolactonic acid, m.p. 100°, on lead tetraacetate oxidation. A by-product of the treatment of sceleranecic acid, potassium salt, with thionyl chloride followed by alkali was a dicarboxylic acid, CxoHjgOg, m.p. 192°, which was also obtainable fix>m... 

The general structure CXLIII of the Cio necic acids envisaged as two units advanced originally by Kropman and Warren 174) has been found in 12 acids shown in Chart IV. The structures of sceleranecic acid (CXLa)... 

Sceleranecic acid was obtained by de Waal and Pretorius (25) from sceleratine by hydrolysis or hydrogenolysis. The compound had no free carboxyl group but was a dilactone one lactone ring was very stable. The first lactone was opened by treatment with sodium hydroxide in the cold. The second ring was opened only by refluxing with sodium hydroxide. 

Catalytic hydrogenation returned the unchanged sceleranecic acid. A more stable form of the dilactone was also obtained. It was less soluble in water, melted at 213°, but was similar otherwise. 

With the foregoing information, partial structures of the necic acid corresponding to sceleranecic dilactone and of the C8H12O4 oxidation product may be written as CXCVIII and CXCIX, respectively. Structure CXCVIII satisfies the 8- and y -lactone formation, especially the... 

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