Propanthialoxide

Structural formula
	Structural formula of the syn form
General
Surname	Propanthialoxide
other names	1-sulfinyl propane; Propanthial S -oxide; Thiopropanal S oxide;
Molecular formula	C 3 H 6 OS
External identifiers / databases
PubChem	441491
Wikidata	Q3044968
properties
Molar mass	90.14 g mol −1
safety instructions
GHS hazard labeling ; no classification available
GHS hazard labeling ; no classification available
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Propanthialoxide (more precisely Propanthial- S -oxide ) is a chemical compound and the only known naturally occurring thiocarbonyl - S -oxide. It occurs in two isomeric forms.

Natural origin

Onions

The compound is the onion tear irritant released from isoalliin by the enzyme alliinase ( Allium cepa ), of which approx. 95% is in the ( Z ) form.

If the onion injured arises from Isoalliin in the first step by cleavage of the Alaninfragmentes by the alliinase and the enzyme co-factor pyridoxal phosphate , the 1-Propensulfensäure represented by tautomeric hydrogen rearrangement to the so-called lachrymatory factor (engl. Lacrimatory factor , LF), the syn-propanethial-s-oxide in two isomeric forms ( syn- and anti - , wherein the) syn -form is the main product. This is very reactive and can hydrolyze to propionaldehyde , sulfuric acid and hydrogen sulfide , but can also enter into cycloadditions with itself to form four- and five-membered rings. At the higher temperatures of steam distillation at 100 ° C and of course when boiling or frying, dipropyl disulfide is formed in addition to propionaldehyde .

properties

Propanthialoxide hydrolyzes easily with water, releasing propionaldehyde , sulfuric acid and hydrogen sulfide .

Individual evidence

↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
↑ ^a ^b Gerhard Eisenbrand, Alfred Hagen Meyer, Peter Schreier: RÖMPP Lexikon Lebensmittelchemie, 2nd edition, 2006 . Georg Thieme, 2014, p. 2006 ( limited preview in Google Book Search).
↑ Wolfgang Legrum: Fragrances, Between Stench and Scent: Occurrence, Properties and Use of Fragrances and Their Mixtures . Springer-Verlag, 2011, p. 90 ( limited preview in Google Book search).

[NV-1] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[Gerhard_Eisenbrand,_Alfred_Hagen_Meyer,_Peter_Schreier-2] Gerhard Eisenbrand, Alfred Hagen Meyer, Peter Schreier: RÖMPP Lexikon Lebensmittelchemie, 2nd edition, 2006 . Georg Thieme, 2014, p. 2006 ( limited preview in Google Book Search).

[Wolfgang_Legrum-3] Wolfgang Legrum: Fragrances, Between Stench and Scent: Occurrence, Properties and Use of Fragrances and Their Mixtures . Springer-Verlag, 2011, p. 90 ( limited preview in Google Book search).