Structure via PubChem · Public domain (PubChem)
propanethial S-oxide
Sign in to saveAlso known as Thiopropanal S-oxide
'''syn-Propanethial S-oxide (or (Z)-propanethial S-oxide'), a member of a class of organosulfur compounds known as thiocarbonyl S''-oxides (formerly "sulfines"), is a volatile liquid that acts as a lachrymatory agent (triggers tearing and stinging on contact with the eyes).
In the Vinony graph
Within Vinony's link graph, propanethial S-oxide is referenced by 346 other articles, and connects out to Onion, tear gas and hepoxilin.
It sits within the topics Chembox image size set, Lachrymatory agents and Onions.
Its subject is documented across 14 Wikipedia language editions.
Chemical data
- Formula
- C3H6OS
- Molecular weight
- 90.15 g/mol
- IUPAC name
- 1-sulfinylpropane
- SMILES
- CCC=S=O
- InChIKey
- BAZSXBOAXJLRNH-UHFFFAOYSA-N
- XLogP
- 0.2
- Polar surface area
- 18.1 Ų
- H-bond donors
- 0
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Wikidata facts
- Mass
- 90.013936
Show 4 more facts
- chemical formula
- C₃H₆OS
- canonical SMILES
- CCC=S=O
- found in taxon
- Welsh onion
- Commons category
- Propanethial-S-oxide
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
3 sectionsContents
- Onion release
- Related compounds
- 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"), 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. Vapors from this volatile liquid induce tearing.
Excerpted from Wikipedia’s “propanethial S-oxide” article, available under the CC BY-SA 4.0 licence.