View source for Syn-Propanethial-S-oxide

{{DISPLAYTITLE:''syn''-Propanethial-''S''-oxide}}
{{chembox
| verifiedrevid = 450633847
| Name = ''syn''-Propanethial ''S''-oxide
| ImageFile = Syn-Propanethial S-oxide Structural Formula V1.svg
| ImageSize = 150px
| ImageFile1 = Syn-propanethial-S-oxide-3D-balls.png
| ImageSize1 = 150px
| IUPACName = (''Z'')-propylidene-λ<sup>4</sup>-sulfanone<ref>{{BlueBook2013|rec=74.2.2.1.8}}</ref>
| OtherNames = Thiopropanal ''S''-oxide <br /> 1-Sulfinylpropane
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 32157-29-2
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 94Z73U61UH
| PubChem = 441491
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 390214
| SMILES = O=S=C/CC
| InChI = 1/C3H6OS/c1-2-3-5-4/h3H,2H2,1H3
| InChIKey = BAZSXBOAXJLRNH-UHFFFAOYAF
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C3H6OS/c1-2-3-5-4/h3H,2H2,1H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = BAZSXBOAXJLRNH-UHFFFAOYSA-N
}}
|Section2={{Chembox Properties
| C=3 | H=6 | O=1 | S=1
| Appearance =
| Density =
| MeltingPt =
| BoilingPt =
| Solubility =
}}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
}}
}}
'''''syn''-Propanethial ''S''-oxide''' (or '''(''Z'')-propanethial ''S''-oxide'''), a member of a class of [[organosulfur]] compounds known as [[thiocarbonyl]] ''S''-oxides (formerly "[[sulfine]]s"),<ref>{{ cite book | author = Zwanenburg, B. |editor=Padwa, A. |year=2004 |chapter=Thioaldehyde and Thioketone ''S''-Oxides and ''S''-Imides (Sulfines and Derivatives) |title=Heteroatom Analogues of Aldehydes and Ketones |series=Science of Synthesis |volume=27 |pages=135–176 |isbn=978-1-58890-204-7}}</ref> 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 [[alliinase]]s, which then break down [[amino acid]] [[sulfoxide]]s, generating [[sulfenic acid]]s. 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.<ref>{{ cite book |author=Block, E. |title=Garlic and Other Alliums: The Lore and the Science |url=https://books.google.com/books?id=6AB89RHV9ucC |publisher=Royal Society of Chemistry |year=2010 |isbn=978-0-85404-190-9 |page=132 }}</ref> Vapors from this volatile liquid induces tearing.<ref name="Sciam">{{ cite web |last=Scott |first=T. |title=What is the chemical process that causes my eyes to tear when I peel an onion?  |work=Ask the Experts: Chemistry |date=1999-10-21 |publisher=[[Scientific American]] |url=http://www.sciam.com/article.cfm?id=what-is-the-chemical-proc |access-date=2012-04-03 }}
</ref>
==Related compounds==
A structurally related lachrymatory compound, ''syn''-butanethial ''S''-oxide, C<sub>4</sub>H<sub>8</sub>OS, has been found in another genus ''Allium'' plant, ''[[Allium siculum]]''.<ref>{{ cite journal |author1=Kubec, R. |author2=Cody, R. B. |author3=Dane, A. J. |author4=Musah, R. A. |author5=Schraml, J. |author6=Vattekkatte, A. |author7=Block, E. |title=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= Journal of Agricultural and Food Chemistry |year=2010 |volume=58 |issue=2 |pages=1121–1128 |pmid=20047275 |doi=10.1021/jf903733e}}</ref>
==See also==
* [[Allicin]]
==References==
{{reflist}}
{{Allium}}
{{Transient receptor potential channel modulators}}
{{DEFAULTSORT:Propanethial-S-oxide, syn-}}
[[Category:Organosulfur compounds]]
[[Category:Lachrymatory agents]]
[[Category:Pungent flavors]]
[[Category:Onions]]
[[Category:Sulfoxides]]