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). 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)-CH3CH=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)-CH3CH2−CH=S+−O−. Vapors from this volatile liquid induce tearing.
Related compounds
Propanethial S-oxide forms a stable dimer, trans-3,4-diethyl-1,2-dithietane 1,1-dioxide. A structurally related lachrymatory compound, syn-butanethial S-oxide, (Z)-CH3CH2CH2−CH=S+−O−, has been found in Allium siculum, a relative of the onion. It is produced via an analogous reaction. A non-Allium analogue is syn-phenylmethanethial S-oxide (Z)-Ph−CH=S+−O− from Petiveria alliacea. It too undergoes a similar biosynthetic route.
References




