Asparagusic acid

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Asparagusic acid[1]
Asparagusic acid Asparagusic acid
Identifiers
CAS number 2224-02-4 YesY
PubChem 16682
ChemSpider 15819 YesY
KEGG C01892 YesY
ChEBI CHEBI:18091 YesY
Jmol-3D images Image 1
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]
Hazards
Flash point 149.7 °C (301.5 °F; 422.8 K)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY (verify) (what is: YesY/N?)
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[edit]

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[edit]

  1. ^ 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. ^ 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 (4 Pt 2): 539–534. PMID 11259347. Retrieved January 18, 2010. 
  4. ^ 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. 
  5. ^ 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. 
  6. ^ 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.