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Asparagusic acid

Asparagusic acid


IUPAC name	1,2-dithiolane-4-carboxylic acid
Other names	?
Identifiers
CAS number	2224-02-4
SMILES	O=C(O)C1CSSC1
Properties
Molecular formula	C₄H₆O₂S₂
Molar mass	150.21 g mol⁻¹
Related Compounds
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

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

The references in this article would be clearer with a different or consistent style of citation, footnoting, or external linking.

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).

Categories: Carboxylic acids | Organosulfur compounds | Thiols