Asparagusic acid
Encyclopedia : A : AS : ASP : Asparagusic acid
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| Systematic name | ? |
| Other names | ? |
| Molecular formula | ? |
| SMILES | ? |
| Molar mass | ?.?? g/mol |
| Appearance | ? |
| CAS number | [?-?-?] |
| 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 | ?° |
| Viscosity | ? cP at ?°C |
| Structure | |
| Molecular shape | ? |
| Coordination geometry | ? |
| Crystal structure | ? |
| Dipole moment | ? D |
| Hazards | |
| MSDS | External MSDS |
| Main hazards | ? |
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| 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 |
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| Other anions | ? |
| Other cations | ? |
| Related ? | ? |
| Related compounds | ? |
| Except where noted otherwise, data are given for materials in their standard state (at 25°C, 100 kPa) [Chemical infoboxInfobox disclaimer and references] | |
Asparagusic acid is 1,2-dithiolane-4-carboxylic acid, S2(CH2)2CHCO2H. It is 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.
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
- 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).
External links
- For a full list of external links to MSDSs, spectroscopic data, commercial chemicals suppliers etc. for this compound, see [Chemical sources].
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