Chemistry:Thialdine
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| IUPAC name
2,4,6-Trimethyl-1,3,5-dithiazinane
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| Other names
Dihydro-2,4,6-trimethyl-4H-1,3,5-dithiazine
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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). | |
| Infobox references | |
Thialdine is a basic heterocyclic chemical compound with the molecular formula C6H13NS2.
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]
Acetaldehyde ammonia trimer is the cyclic trimer formed in the condensation reaction of acetaldehyde with ammonia:
- 3 CH
3CHO + 3 NH
3 → (CH
3CHNH)
3 + 3 H
2O
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]
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]
References
- ↑ Wöhler, Liebig (1847). "Ueber das Thialdin und Selenaldin, zwei künstlich darstellbare organische Basen". Annalen der Chemie und Pharmacie 61: 1. doi:10.1002/jlac.18470610102. https://zenodo.org/record/2179823/files/article.pdf.
- ↑ Day, Cynthia S.; Hansen, Thomsen J.; Keefer, Larry K. (1982). "Stereochemistry of thialdine". Journal of Heterocyclic Chemistry 19 (6): 1301–1304. doi:10.1002/jhet.5570190608.
- ↑ Lijst van aromastoffen als bedoeld in Verordening 2232/96, tot opname van die lijst in bijlage I bij Verordening 1334/2008. (number 15.109)
- ↑ R.L. Smith, J. Doull, V.J. Feron, J.I. Goodman, I.C. Munro, P.M. Newberne, P.S. Portoghese, W.J. Waddell, B.M. Wagner, T.B. Adams, and M.M. McGowen (December 2001). "GRAS Flavoring Substances 20". Food Technology 55 (12). https://www.femaflavor.org/sites/default/files/20.%20GRAS%20Substances%20%283964-4023%29.pdf.
- ↑ The Good Scents Company: Thialdine
- ↑ Hydrocarbon oil additive, U.S. Patent 2712526, July 5, 1955, Exxon Research Engineering Co.
- ↑ Rubber vulcanization accelerator, U.S. Patent 1664481, April 3, 1928, Rubber Service Lab Co.
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