Chemistry:Syn-Propanethial-S-oxide

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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
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).
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Infobox references
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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). The chemical is released from onions, Allium cepa, as they are sliced.

Onion release

The release from onions 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. Isoalliin is specifically converted to 1-propenesulfenic acid (E)-CH
3CH=CH–S–OH by allinase. This product is rearranged by lachrymatory factor synthase (LFS, EC 5.3.99.12) to give syn-propanethial S-oxide (Z)-CH
3CH
2–CH=S+
–O-
.[3] Vapors from this volatile liquid induce tearing.[4]

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.[5]

A structurally related lachrymatory compound, syn-butanethial S-oxide, (Z)-CH
3CH
2CH
2–CH=S+
–O-
, has been found in Allium siculum, a relative of the onion. It is produced via an analogous reaction.[6]

A non-Allium analogue is syn-phenylmethanethial S-oxide (Z)-Ph–CH=S+
–O-
 from Petiveria alliacea. It too undergoes a similar biosynthetic route.[7]

References

  1. ↑ IUPAC Chemical Nomenclature and Structure Representation Division (2013). "P-74.2.2.1.8". in Favre, Henri A.; Powell, Warren H.. Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. IUPAC–RSC. ISBN 978-0-85404-182-4. https://pubs.rsc.org/en/Content/eBook/978-0-85404-182-4. 
  2. ↑ Zwanenburg, B. (2004). "Thioaldehyde and Thioketone S-Oxides and S-Imides (Sulfines and Derivatives)". in Padwa, A.. Heteroatom Analogues of Aldehydes and Ketones. Science of Synthesis. 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. https://books.google.com/books?id=6AB89RHV9ucC. 
  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. http://www.sciam.com/article.cfm?id=what-is-the-chemical-proc. 
  5. ↑ 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. doi:10.1021/ja00527a074. Bibcode: 1980JAChS.102.2490B. 
  6. ↑ 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. 
  7. ↑ Musah, RA; He, Q; Kubec, R (November 2009). "Discovery and characterization of a novel lachrymatory factor synthase in Petiveria alliacea and its influence on alliinase-mediated formation of biologically active organosulfur compounds.". Plant physiology 151 (3): 1294-303. doi:10.1104/pp.109.142539. PMID 19692535. 



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