Thialdine

Thialdine
Names
	IUPAC name 2,4,6-Trimethyl-1,3,5-dithiazinane
	Other names Dihydro-2,4,6-trimethyl-4H-1,3,5-dithiazine
Identifiers
CAS Number	86241-90-9; (all-cis): 638-17-5;
3D model (JSmol)	Interactive image; (all-cis): Interactive image;
ChEBI	CHEBI:179054;
ChemSpider	12001;
ECHA InfoCard	100.010.295
EC Number	211-323-3;
PubChem CID	12518;
UNII	ZKG651IE9G;
CompTox Dashboard (EPA)	DTXSID10862338 ;
	InChI InChI=1S/C6H13NS2/c1-4-7-5(2)9-6(3)8-4/h4-7H,1-3H3 Key: FBMVFHKKLDGLJA-UHFFFAOYSA-N;
	SMILES CC1NC(SC(S1)C)C; (all-cis): C[C@H]1N[C@@H](C)S[C@@H](C)S1;
Properties
Chemical formula	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]

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]

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.
^ 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" (PDF). Food Technology. 55 (12).{{cite journal}}: CS1 maint: multiple names: authors list (link)
^ 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.

[1] 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.

[2] 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.

[3] Lijst van aromastoffen als bedoeld in Verordening 2232/96, tot opname van die lijst in bijlage I bij Verordening 1334/2008. (number 15.109)

[4] 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" (PDF). Food Technology. 55 (12).{{cite journal}}: CS1 maint: multiple names: authors list (link)

[5] The Good Scents Company: Thialdine

[6] Hydrocarbon oil additive, U.S. Patent 2712526, July 5, 1955, Exxon Research Engineering Co.

[7] Rubber vulcanization accelerator, U.S. Patent 1664481, April 3, 1928, Rubber Service Lab Co.

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