syn-Propanethial-S-oxide

syn-Propanethial S-oxide
Names
IUPAC name
(Z)-propylidene-λ4-sulfanone[1]
Other names
Thiopropanal S-oxide
1-Sulfinylpropane
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C3H6OS/c1-2-3-5-4/h3H,2H2,1H3 checkY
    Key: BAZSXBOAXJLRNH-UHFFFAOYSA-N checkY
  • InChI=1/C3H6OS/c1-2-3-5-4/h3H,2H2,1H3
    Key: BAZSXBOAXJLRNH-UHFFFAOYAF
SMILES
  • O=S=C/CC
Properties
Chemical formula
 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).
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Infobox references

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).

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 induce tearing.[4]

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

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

Propanethial S-oxide forms a stable 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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