Asparagusic acid
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Asparagusic acid
| Asparagusic acid[1] | |
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1,2-Dithiolane-4-carboxylic acid |
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| Identifiers | |
| CAS number | 2224-02-4  |
| PubChem | 16682 |
| ChemSpider | 15819 |
| KEGG | C01892 |
| ChEBI | CHEBI:18091 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C4H6O2S2 |
| Molar mass | 150.22 g mol−1 |
| Appearance | Colorless solid |
| Density | 1.50cg/cm3 |
| Melting point |
75.7–76.5 °C[2] |
| Boiling point |
323.9 °C @ 760mmHg |
| Hazards | |
| Flash point | 149.7 °C |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox 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.[3] Biosynthetic studies revealed that asparagusic acid is derived from isobutyric acid.[4] This colorless solid has a melting point (m.p.) of 75.7–76.5 °C.[2] The corresponding dithiol (m.p. 59.5–60.5 °C) is also known;[5] it is called dihydroasparagusic acid or dimercaptoisobutyric acid.
Isolation
From 40 kg of "asparagus aroma concentrate," Jansen obtained 32 g of a compound he identified as 3,3’-dimercaptoisobutyric acid.[6]
References
- ^ Yanagawa, H.; Kato, T.; Sagami, H.; Kitahara, Y. (1973). "Convenient procedure for the synthesis of asparagusic acids". Synthesis 10 (10): 607–608. doi:10.1055/s-1973-22265.
- ^ a b Foss, Olav; Tjomsland, Olav (1958). "Crystal and molecular structure of 1,2-dithiolane-4-carboxylic acid". Acta Chemica Scandinavica 12: 1810–18. doi:10.3891/acta.chem.scand.12-1810.
- ^ S.C. Mitchell (2001). "Food Idiosyncrasies: Beetroot and Asparagus". Drug Metabolism and Disposition 29 (4 Pt 2): 539–534. PMID 11259347. http://dmd.aspetjournals.org/content/29/4/539.full. Retrieved january 18, 2010.
- ^ R. J. Parry, A. E. Mizusawa, I. C. Chiu, M. V. Naidu, and M. Ricciardone (1985). "Biosynthesis of Sulfur Compounds. Investigations of the Biosynthesis of Asparagusic Acid". Journal of the American Chemical Society 107 (8): 2512–2521. doi:10.1021/ja00294a051.
- ^ R. Singh, G. M. Whitesides (1990). "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 (3): 1190–1197. doi:10.1021/ja00159a046.
- ^ Jansen, E. F. (1948). "The Isolation and Identification of 2,2’-Dithiolisobutyric Acid from Asparagus". Journal of Biological Chemistry 176 (2): 657–664. PMID 18889921.
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