syn-Propanethial-S-oxide

*syn*-Propanethial S-oxide
Names
	IUPAC name (Z)-propylidene-λ4-sulfanone
	Other names Thiopropanal S-oxide ; 1-Sulfinylpropane
Identifiers
CAS Number	32157-29-2 ;
3D model (JSmol)	Interactive image;
ChemSpider	390214 ;
PubChem CID	441491;
UNII	94Z73U61UH ;
CompTox Dashboard (EPA)	DTXSID50954029 ;
	InChI InChI=1S/C3H6OS/c1-2-3-5-4/h3H,2H2,1H3 Key: BAZSXBOAXJLRNH-UHFFFAOYSA-N ; 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). verify (what is ?) 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). The chemical is released from onions, Allium cepa, as they are sliced. The release is due to the breaking open of the onion cells and their releasing 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] Vapors from this volatile liquid induces tearing.^[4]

Related compounds

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

References

^ 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.
^ 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.
^ Block, E. (2010). Garlic and Other Alliums: The Lore and the Science. Royal Society of Chemistry. p. 132. ISBN 978-0-85404-190-9.
^ 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.
^ 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.

[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.

[Sciam-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.

[1]

[2]

[3]

[4]

[5]

Related compounds

See also

References