Asparagusic acid

Asparagusic acid^[1]

Names
IUPAC name 1,2-Dithiolane-4-carboxylic acid
Identifiers
CAS Number	2224-02-4
ChEBI	CHEBI:18091
ChemSpider	15819
Jmol interactive 3D	Image
KEGG	C01892
PubChem	16682
InChI InChI=1S/C4H6O2S2/c5-4(6)3-1-7-8-2-3/h3H,1-2H2,(H,5,6) Key: AYGMEFRECNWRJC-UHFFFAOYSA-N InChI=1/C4H6O2S2/c5-4(6)3-1-7-8-2-3/h3H,1-2H2,(H,5,6) Key: AYGMEFRECNWRJC-UHFFFAOYAA
SMILES O=C(O)C1CSSC1
Properties
Chemical formula	C4H6O2S2
Molar mass	150.21 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	323.9 °C (615.0 °F; 597.0 K) at 760mmHg
Hazards
Flash point	149.7 °C (301.5 °F; 422.8 K)
Except where otherwise noted, data are 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

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. 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.