Asparagusic acid

Asparagusic acid[1]
Asparagusic acid
Asparagusic acid
Asparagusic acid
Asparagusic acid
Names
Preferred IUPAC name
1,2-Dithiolane-4-carboxylic acid
Other names
1,2-Dithiacyclopentane-4-carboxylic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
UNII
  • InChI=1S/C4H6O2S2/c5-4(6)3-1-7-8-2-3/h3H,1-2H2,(H,5,6) checkY
    Key: AYGMEFRECNWRJC-UHFFFAOYSA-N checkY
  • InChI=1/C4H6O2S2/c5-4(6)3-1-7-8-2-3/h3H,1-2H2,(H,5,6)
    Key: AYGMEFRECNWRJC-UHFFFAOYAA
  • O=C(O)C1CSSC1
Properties
C4H6O2S2
Molar mass 150.21 g·mol−1
Appearance Colorless solid
Density 1.50 g cm−3
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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Asparagusic acid is an organosulfur compound with the molecular formula C4H6O2S2 and systematically named 1,2-dithiolane-4-carboxylic acid. The molecule consists of a heterocyclic disulfide functional group (a 1,2-dithiolane) with a carboxylic acid side chain. It is found in asparagus and is believed to be the metabolic precursor to odorous sulfur compounds responsible for the distinctive smell of urine which has long been associated with eating asparagus.[3][4]

  1. ^ Yanagawa, H.; Kato, T.; Sagami, H.; Kitahara, Y. (1973). "Convenient procedure for the synthesis of asparagusic acids". Synthesis. 1973 (10): 607–608. doi:10.1055/s-1973-22265.
  2. ^ Foss, O.; Tjomsland, O. (1958). "Crystal and molecular structure of 1,2-dithiolane-4-carboxylic acid". Acta Chemica Scandinavica. 12: 1810–1818. doi:10.3891/acta.chem.scand.12-1810.
  3. ^ Mitchell, S. C. (2001). "Food idiosyncrasies: Beetroot and asparagus". Drug Metabolism and Disposition. 29 (4): 539–543. PMID 11259347.
  4. ^ Pelchat, M. L.; Bykowski, C.; Duke, F. F.; Reed, D. R. (2011). "Excretion and perception of a characteristic odor in urine after asparagus ingestion: A psychophysical and genetic study". Chemical Senses. 36 (1): 9–17. doi:10.1093/chemse/bjq081. PMC 3002398. PMID 20876394.