Asparagusic acid

Asparagusic acid, S₂(CH₂)₂CHCO₂H is an organosulfur carboxylic acid present in the vegetable asparagus and may be the metabolic precursor to other odorous thiol compounds. Biosynthetic studies revealed that asparagusic acid is derived from the amino acid valine. This colorless solid has a m.p. of 75.7-76.5 °C. The corresponding dithiol (m.p. 59.5-60.5 °C) is also known; it is called dihydroasparagusic acid or dimercaptoisobutyric acid.

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Isolation

From 40 kg of "asparagus aroma concentrate," Jansen obtained 32 g of a compound he identified as 3,3’-dimercaptoisobutyric acid.

see thiol

References

• Jansen, E. F. "The Isolation and Identification of 2,2’-Dithiolisobutyric Acid from Asparagus" Journal of Biological Chemistry 176: 657-664 (1948).
• Yanagawa, H.; Kato, T.; Sagami, H.; Kitahara, Y. Synthesis 1973, p. 607ff
• R. J. Parry, A. E. Mizusawa, I. C. Chiu, M. V. Naidu, and M. Ricciardone "Biosynthesis of Sulfur Compounds. Investigations of the Biosynthesis of Asparagusic Acid" Journal of the American Chemical Society 107: 2512-2521 (1985).
• R. Singh, G. M. Whitesides "Comparisons of Rate Constants for Thiolate-Disulfide Interchange in Water and in Polar Aprotic Solvents Using Dynamic 'H NMR Line Shape Analysis" J. Am. Chem. Soc. 112: 1190-1197 (1990) (synthesis of the dihydro compound).
• S.C. Mitchell "Food Idiosyncrasies: Beetroot and Asparagus" Drug Metabolism and Disposition 29: 539-534 (2001).