Asparagusic acid

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Reference= [cite journal | author=Yanagawa, H.; Kato, T.; Sagami, H.; Kitahara, Y. |journal = Synthesis |title =Convenient procedure for the synthesis of asparagusic acids |year =1973 |volume = 10 |pages=607–608 | doi=10.1055/s-1973-22265]
Name = Asparagusic acid
ImageFileL1 = Asparagusic-acid.png ImageSizeL1 = 100px
ImageNameL1 = Asparagusic acid
ImageFileR1 = Asparagusic-acid-3D-balls.png ImageSizeR1 = 100px
ImageNameR1 = Asparagusic acid
IUPACName = 1,2-Dithiolane-4-carboxylic acid
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SMILES = O=C(O)C1CSSC1
CASNo = 2224-02-4
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C=4|H=6|O=2|S=2
Appearance = Colorless solid
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MeltingPt = 75.7-76.5 °Ccite journal | title=Crystal and molecular structure of 1,2-dithiolane-4-carboxylic acid |author=Foss, Olav; Tjomsland, Olav |journal=Acta Chemica Scandinavica |year=1958 |volume=12 |pages=1810–18 | doi=10.3891/acta.chem.scand.12-1810]
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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. [cite journal| author=S.C. Mitchell |title=Food Idiosyncrasies: Beetroot and Asparagus |journal=Drug Metabolism and Disposition |volume=29 |pages=539–534 |year=2001] Biosynthetic studies revealed that asparagusic acid is derived from isobutyric acid. [cite journal | author = R. J. Parry, A. E. Mizusawa, I. C. Chiu, M. V. Naidu, and M. Ricciardone |title=Biosynthesis of Sulfur Compounds. Investigations of the Biosynthesis of Asparagusic Acid| journal=Journal of the American Chemical Society volume=107 | pages=2512–2521 |year=1985 | doi = 10.1021/ja00294a051 | volume = 107] 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; [cite journal | author=R. Singh, G. M. Whitesides |title=Comparisons of Rate Constants for Thiolate-Disulfide Interchange in Water and in Polar Aprotic Solvents Using Dynamic 'H NMR Line Shape Analysis |journal=J. Am. Chem. Soc. |volume=112 |pages=1190–1197 |year=1990 | doi=10.1021/ja00159a046] 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. [cite journal| author=Jansen, E. F. |title=The Isolation and Identification of 2,2’-Dithiolisobutyric Acid from Asparagus| journal=Journal of Biological Chemistry |volume=176 |pages=657–664 |year=1948]

References