Asparagusic acid
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| Names | |||
|---|---|---|---|
| IUPAC name
1,2-Dithiolane-4-carboxylic acid | |||
| Identifiers | |||
2224-02-4  | |||
| ChEBI | CHEBI:18091 | ||
| ChemSpider | 15819 | ||
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| Jmol-3D images | Image | ||
| KEGG | C01892 | ||
| PubChem | 16682 | ||
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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 to 76.5 °C (168.3 to 169.7 °F; 348.8 to 349.6 K)[2] | ||
| Boiling point | at 760mmHg | ||
| Hazards | |||
| Flash point | 149.7 °C (301.5 °F; 422.8 K) | ||
| Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | |||
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| Infobox references | |||
Asparagusic acid is the organosulfur with the formula S2(CH2)2CHCO2H. The molecule contains both carboxylic acid and disulfide functional groups. It is present in the vegetable asparagus and may be the metabolic precursor to other odorous thiol compounds.[3]
Isolation and biosynthesis
The material was originally isolated from an aqueous extract of asparagus.[4]
Biosynthetic studies revealed that asparagusic acid is derived from isobutyric acid.[5] 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;[6] it is called dihydroasparagusic acid or dimercaptoisobutyric acid.
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.
- ↑ 2.0 2.1 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. Retrieved January 18, 2010.
- ↑ 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.
- ↑ 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.