Asparagusic acid
From Wikipedia, the free encyclopedia
| Asparagusic acid | |
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| 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 |
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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.
[edit] Isolation
From 40 kg of "asparagus aroma concentrate," Jansen obtained 32 g of a compound he identified as 3,3’-dimercaptoisobutyric acid.
see thiol
[edit] References
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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).
