The isolation of shikimic acid from Eucalyptus citriodora Hook

Australian Journal of Chemistry
1957.0

Abstract

Young leaves of Eucalyptus citriodora Hook. (10 kg) were frozen in liquid air immediately on picking, pulped, and extracted with 95 per cent. ethanol to give an approx. 50 per cent. ethanolic solution, which was passed through a cation-exchange resin "Zeocarb 225" to remove bases and amino acids. Following the method of Anet and Reynolds (1955), acids were collected on an anion-exchange resin "Amberlite IR-4B" and displaced with 0.1N hydrochloric acid onto a series of four columns of "Amberlite IRA-400". Paper chromatography using methyl ethyl ketone : cineole : formic acid (85 per cent.) : water (50 : 50 : 20 : 16 v/v) together with the sequence of emergence from the columns indicated the presence of quinic acid, glutaric acid, succinic acid, malic acid, citric acid, phosphoric acid, hydrochloric acid, and small amounts of unknown acids. Fractions containing acid R₁ were evaporated to yield 3 g of product, which crystallized from water (m.p. 183 °C, [α]₁₅ -178° (c, 0.04 in water)). Elemental analysis (Found: C, 48.1; H, 5.8%. Calc. for C₇H₁₀O₅: C, 48.3; H, 5.8%) and equivalent weight (175) were consistent with shikimic acid. The product showed no depressed melting point (183-186 °C) when mixed with authentic shikimic acid (m.p. 183-187 °C), and their infra-red spectra ("Nujol" mull) were identical (authentic shikimic acid has m.p. 184 °C, [α]₁₀ -176° (c, 0.02 in ethanol), equiv. wt. 174 (Grewe and Lorenzen 1953)). The presence of comparatively large quantities of shikimic acid and quinic acid in rapidly developing leaves is of interest in connection with their probable incorporation into phenylalanine, tryptophan, and lignin (e.g., Davis 1953).

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