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Thiazoline

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Thiazoline

Thiazoline
Identifiers
CAS number 504-79-0 YesY
PubChem 120269
Jmol-3D images Image 1
Properties
Molecular formula C3H5NS
Appearance colourless liquid
Boiling point

135-8 °C

 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Thiazoline is a heterocyclic compound containing both sulfur and nitrogen in the ring. Although thiazoline itself is rarely encountered, its derivatives are often bioactive. For example, in a common post-translational modification, cysteine residues are converted into thiazolines.[1]

Synthesis

Thiazolines were first prepared by dialkylation of thioamides.[2] More commonly, they are prepared from derivatives of 2-aminoethanethiol (cysteamine).


Related compounds

Three related classes of C3NS heterocycles are well studied, 1,3-thiazoles (parent: C3H3NS), 1,3-thiazolines (parent: C3H5NS), and 1,3-thiazolidines (parent: C3H7NS). The naming is analogous to the C3N2 heterocycles, imidazoles, imidazolines, and imidazolidines.

Substituted thiazolines

Many molecules contain thiazoline rings, one example being luciferin, the light-emitting molecule in fireflies. The amino acid cysteine is produced industrially from substituted thiazole.[3]

Thiazolines found in nature

In a recent study, thiazolines were identified in nature through an analysis of sesame seed oil. The toasted sesame seed oil was extracted using a Solvent-Assisted Flavor Evaporation technique. The extract was analyzed by GC and GC-MS and a total of 87 components were identified. Amongst these components, 2-ethyl-4-methyl-3-thiazoline and 2-isopropyl-4-methyl-3-thiazoline were identified and confirmed as being present in a natural product for the first time.[4]

References

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