syn-Propanethial-S-oxide

Source: Wikipedia, the free encyclopedia.
syn-Propanethial S-oxide
Names
IUPAC name
(Z)-propylidene-λ4-sulfanone[1]
Other names
Thiopropanal S-oxide
1-Sulfinylpropane
Identifiers
3D model (
JSmol
)
ChemSpider
UNII
  • 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
  • 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).
checkY verify (what is checkY☒N ?)

syn-Propanethial S-oxide (or (Z)-propanethial S-oxide), a member of a class of

enzymes called alliinases, which then break down amino acid sulfoxides, generating sulfenic acids. A specific sulfenic acid, 1-propenesulfenic acid, formed when onions are cut, is rapidly rearranged by a second enzyme, called the lachrymatory factor synthase or LFS, giving syn-propanethial S-oxide.[3] The gas diffuses through the air and, on contact with the eye, it stimulates sensory neurons creating a stinging, painful sensation. Tears are released from the tear glands to dilute and flush out the irritant.[4] A structurally related lachrymatory compound, syn-butanethial S-oxide, C4H8OS, has been found in another genus Allium plant, Allium siculum.[5]

See also

References

  1. ISBN 978-0-85404-182-4
    .
  2. ISBN 978-1-58890-204-7
    .
  3. 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. PMID 20047275
    .
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