Asparagusic acid
From Wikipedia, the free encyclopedia
| Asparagusic acid | |
|---|---|
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| General | |
| Systematic name | 1,2-dithiolane-4-carboxylic acid |
| Other names | ? |
| Molecular formula | C4H6O2S2 |
| SMILES | O=C(O)C1CSSC1 |
| Molar mass | 150.21 g mol−1 |
| Appearance | ? |
| CAS number | [2224-02-4] |
| Properties | |
| Density and phase | ? g/cm3, ? |
| Solubility in water | ? g/100 ml (?°C) |
| Melting point | ?°C (? K) |
| Boiling point | ?°C (? K) |
| Acidity (pKa) | ? |
| Basicity (pKb) | ? |
| Chiral rotation [α]D | ?° |
| Viscosity | ? cP at ?°C |
| Structure | |
| Molecular shape | ? |
| Crystal structure | ? |
| Dipole moment | ? D |
| Hazards | |
| MSDS | External MSDS |
| Main hazards | ? |
| NFPA 704 | |
| Flash point | ?°C |
| R/S statement | R: ? S: ? |
| RTECS number | ? |
| Supplementary data page | |
| Structure and properties |
n, εr, etc. |
| Thermodynamic data |
Phase behaviour Solid, liquid, gas |
| Spectral data | UV, IR, NMR, MS |
| Related compounds | |
| Related carboxylic acids | ? |
| 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
- 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" J. Am. Chem. Soc. 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" Journal of the American Chemical Society 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).
