Thialdine is a basic heterocyclic chemical compound with the molecular formula C6H13NS2.
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| IUPAC name 2,4,6-Trimethyl-1,3,5-dithiazinane | |
| Other names Dihydro-2,4,6-trimethyl-4H-1,3,5-dithiazine | |
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3D model (JSmol) |
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| ChemSpider | |
| ECHA InfoCard | 100.010.295 |
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| Properties | |
| C6H13NS2 | |
| Molar mass | 163.30 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
Preparation
Thialdine was first synthesized by Justus von Liebig and Friedrich Wöhler in 1847 by passing hydrogen sulfide through a solution of acetaldehyde ammonia trimer, with thialdine crystallizing from the solution.[1]
Preparation of thialdine
Acetaldehyde ammonia trimer is the cyclic trimer formed in the condensation reaction of acetaldehyde with ammonia:
- 3 CH3CHO + 3 NH3 → (CH3CHNH)3 + 3 H2O
The aldehyde ammonia does not need to be isolated as an intermediate.
The configuration of the three methyl groups in thialdine can differ, so that multiple cis-trans isomers are possible. However, X-ray diffraction has shown that in practice thialdine occurs in the all-cis configuration.[2]
All-cis-thialidine
Uses
Thialdine is used as a flavoring agent in foods. It is included in the list of flavoring substances authorized in the European Union[3] and is considered generally recognized as safe (GRAS) in the United States.[4] The FEMA number of thialdine is 4018. Thialdine has a roasted meat smell and is therefore used as a flavoring in meat.[5]
Salts of thialdine have been used as an antioxidant additive in lubricating oils.[6]
Thialdine and similar compounds have been proposed as rubber vulcanization accelerators.[7]