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Asparagusic acid[1]
Asparagusic acid
Asparagusic acid
IUPAC name
Identifiers
CAS number 2224-02-4
SMILES
Properties
Molecular formula C4H6O2S2
Molar mass 150.22 g mol−1
Appearance Colorless solid
Melting point

75.7-76.5 °C[2]

Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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 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

  1. ^ Yanagawa, H.; Kato, T.; Sagami, H.; Kitahara, Y. (1973). "Convenient procedure for the synthesis of asparagusic acids". Synthesis 10: 607–608. doi:10.1055/s-1973-22265.  
  2. ^ 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.  
  3. ^ S.C. Mitchell (2001). "Food Idiosyncrasies: Beetroot and Asparagus". Drug Metabolism and Disposition 29: 539–534.  
  4. ^ 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: 2512–2521. doi:10.1021/ja00294a051.  
  5. ^ 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: 1190–1197. doi:10.1021/ja00159a046.  
  6. ^ Jansen, E. F. (1948). "The Isolation and Identification of 2,2’-Dithiolisobutyric Acid from Asparagus". Journal of Biological Chemistry 176: 657–664.  
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