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Syn-Propanethial-S-oxide

Syn-Propanethial-S-oxide

1-Sulfinylpropane

syn-Propanethial S-oxide (or (Z)-propanethial S-oxide), a member of a class of organosulfur compounds known as thiocarbonyl S-oxides (formerly "sulfines"), is a volatile liquid that acts as a lachrymatory agent (triggers tearing and stinging on contact with the eyes).

Onion release

The chemical is released from onions, Allium cepa, as they are sliced. The release is due to the breaking open of the onion cells, which releases enzymes called alliinases. Alliinases then break down amino acid sulfoxides, generating sulfenic acids. A specific sulfenic acid, allicin or 1-propenesulfenic acid, is rapidly rearranged by another enzyme, the lachrymatory factor synthase (LFS), to give syn-propanethial S-oxide. Vapors from this volatile liquid induce tearing.

References

References

  1. {{BlueBook2013
  2. Zwanenburg, B.. (2004). "Heteroatom Analogues of Aldehydes and Ketones".
  3. Block, E.. (2010). "Garlic and Other Alliums: The Lore and the Science". Royal Society of Chemistry.
  4. (2010). "Applications of DART Mass Spectrometry in Allium Chemistry. (''Z'')-Butanethial ''S''-Oxide and 1-Butenyl Thiosulfinates and their ''S''-(''E'')-1-Butenylcysteine ''S''-Oxide Precursor from ''Allium siculum''". Journal of Agricultural and Food Chemistry.
  5. Block, E. (1980). "The chemistry of sulfines. 6. Dimer of the onion lachrymatory factor: the first stable 1,2-dithietane derivative". J. Am. Chem. Soc..
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organosulfur-compounds lachrymatory-agents pungent-flavors onions sulfoxides
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