Antibiotics pp 360-365 | Cite as

Tenuazonic Acid

  • Harold T. Shigeura


While investigating the metabolic products of Alternaria tenuis Auct, Rosett et al. (1957) observed that a fraction from the culture filtrate gave a strong orange-red ferric chloride color. The material which was very soluble in organic solvent was ketonic and acidic in nature. Its rotation [α] 5461 19° in methanol was −124°. Analysis of the compound indicated the molecular formula C10H15O2N. On long standing, the rotation of the product slowly became less negative, and the substance eventually crystallized. The purified crystalline substance also corresponded to the formula C10H15O2N and had very similar chemical properties to the original material. However, it was found to be dextrorotatory, [α] 5461 22° + 23°. The name of tenuazonic acid was proposed for the metabolic product and isotenuazonic acid for the isomer. Tenuazonic acid titrated sharply as a monobasic acid, contained no methoxyl group and formed a semicarbazone, m.p. 187–189° and was found to be converted into the iso-acid by boiling with aqueous alkali.


Culture Filtrate Supernatant Fluid Microsomal Protein Cent Inhibition Ehrlich Ascites Carcinoma 
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© Springer-Verlag Berlin Heidelberg 1967

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  • Harold T. Shigeura

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