Syn-Propanethial-S-oxide

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syn-Propanethial S-oxide
Syn-Propanethial S-oxide Structural Formula V1.svg
Syn-propanethial-S-oxide-3D-balls.png
Names
IUPAC name
(Z)-propylidene-λ4-sulfanone [1]
Other names
Thiopropanal S-oxide
1-Sulfinylpropane
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C3H6OS/c1-2-3-5-4/h3H,2H2,1H3 Yes check.svgY
    Key: BAZSXBOAXJLRNH-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C3H6OS/c1-2-3-5-4/h3H,2H2,1H3
    Key: BAZSXBOAXJLRNH-UHFFFAOYAF
  • O=S=C/CC
Properties
C3H6OS
Molar mass 90.14 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

syn-Propanethial S-oxide (or (Z)-propanethial S-oxide), a member of a class of organosulfur compounds known as thiocarbonyl S-oxides (formerly "sulfines"), [2] is a volatile liquid that acts as a lachrymatory agent (triggers tearing and stinging on contact with the eyes).

Contents

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. [3] Vapors from this volatile liquid induces tearing. [4]

A structurally related lachrymatory compound, syn-butanethial S-oxide, C4H8OS, has been found in another genus Allium plant, Allium siculum . [5]

Structure of trans-3,4-diethyl-1,2-dithietane 1,1-dioxide Trans-3,4-diethyl-1,2-dithietane 1,1-dioxide.svg
Structure of trans-3,4-diethyl-1,2-dithietane 1,1-dioxide

Propanethial S-oxide forms a stable thiosultone dimer, trans-3,4-diethyl-1,2-dithietane 1,1-dioxide. [6]

References

  1. ↑ IUPAC Chemical Nomenclature and Structure Representation Division (2013). "P-74.2.2.1.8". In Favre, Henri A.; Powell, Warren H. (eds.). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. IUPAC–RSC. ISBN   978-0-85404-182-4.
  2. ↑ Zwanenburg, B. (2004). "Thioaldehyde and Thioketone S-Oxides and S-Imides (Sulfines and Derivatives)". In Padwa, A. (ed.). Heteroatom Analogues of Aldehydes and Ketones. Science of Synthesis. Vol. 27. pp. 135–176. ISBN   978-1-58890-204-7.
  3. ↑ Block, E. (2010). Garlic and Other Alliums: The Lore and the Science. Royal Society of Chemistry. p. 132. ISBN   978-0-85404-190-9.
  4. ↑ Scott, T. (1999-10-21). "What is the chemical process that causes my eyes to tear when I peel an onion?". Ask the Experts: Chemistry. Scientific American . Retrieved 2012-04-03.
  5. ↑ Kubec, R.; Cody, R. B.; Dane, A. J.; Musah, R. A.; Schraml, J.; Vattekkatte, A.; Block, E. (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. 58 (2): 1121–1128. doi:10.1021/jf903733e. PMID   20047275.
  6. ↑ Block, E; Bazzi, AA; Revelle, LK (1980). "The chemistry of sulfines. 6. Dimer of the onion lachrymatory factor: the first stable 1,2-dithietane derivative". J. Am. Chem. Soc. 102 (7): 2490–2491. Bibcode:1980JAChS.102.2490B. doi:10.1021/ja00527a074.
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