Thietane

Thietane
Structural formula of thietane	Ball-and-stick model of the thietane molecule
Names
	Preferred IUPAC name Thietane
	Systematic IUPAC name Thiacyclobutane
	Other names Trimethylene sulfide
Identifiers
CAS Number	287-27-4 [chemspider];
3D model (JSmol)	Interactive image;
Beilstein Reference	102383
ChEBI	CHEBI:87565;
ChemSpider	8895 ;
ECHA InfoCard	100.005.469
EC Number	206-015-0;
PubChem CID	9251;
UNII	1O7C19QQDB;
UN number	1993
CompTox Dashboard (EPA)	DTXSID7059773 ;
	InChI InChI=1S/C3H6S/c1-2-4-3-1/h1-3H2 Key: XSROQCDVUIHRSI-UHFFFAOYSA-N ;
	SMILES C1CSC1;
Properties
Chemical formula	C3H6S
Molar mass	74.14 g·mol−1
Appearance	Colourless liquid
Odor	Sulfurous
Density	1.028 g cm−3
Boiling point	94 to 95 °C (201 to 203 °F; 367 to 368 K)
Hazards
GHS pictograms
GHS Signal word	Danger
GHS hazard statements	H225, H302
GHS precautionary statements	P210
NFPA 704 (fire diamond)	4 2 1
Flash point	-11(9) °C
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

Thietane is a heterocyclic compound containing a saturated four-membered ring with three carbon atoms and one sulfur atom.[1][2]

Thietane, and its derivative 2-propylthietane, are strong-smelling mouse alarm pheromones and predator scent analogues.[3][4] Both the mouse and human olfactory receptors MOR244-3 and OR2T11, respectively, were found to respond to thietane in the presence of copper.[5]

References

Leśniak, S; Lewkowski, J; Kudelska, W; Zając, A (2008). "Thietanes and Thietes: Monocyclic". Comprehensive Heterocyclic Chemistry III. 2.07: 389–428. doi:10.1016/B978-008044992-0.00207-8.
Block, E; DeWang, M (1996). "Thietanes and Thietes: Monocyclic". Comprehensive Heterocyclic Chemistry II. 1.24: 773–802. doi:10.1016/B978-008096518-5.00024-1.
Sievert, Thorbjörn; Laska, Matthias (2016). "Behavioral responses of CD-1 mice to six predator odor components". Chem. Senses. 41 (5): 399–406. doi:10.1093/chemse/bjw015. PMID 26892309.
Brechbuhl, J; Moine, F; Klaey, M; Nenniger-Tosato, M; Hurni, N; Sporkert, F; Giroud, C; Broillet, MC (2013). "Mouse alarm pheromone shares structural similarity with predator scents". Proc. Natl. Acad. Sci. U.S.A. 110 (12): 4762–4767. doi:10.1073/pnas.1214249110. PMC 3607058. PMID 23487748.
Li, Shengju; Ahmed, Lucky; Zhang, Ruina; Pan, Yi; Matsunami, Hiroaki; Burger, Jessica L; Block, Eric; Batista, Victor S; Zhuang, Hanyi (2016). "Smelling sulfur: Copper and silver regulate the response of human odorant receptor OR2T11 to low molecular weight thiols". Journal of the American Chemical Society. in press: 13281–13288. doi:10.1021/jacs.6b06983. PMID 27659093.

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[1] Leśniak, S; Lewkowski, J; Kudelska, W; Zając, A (2008). "Thietanes and Thietes: Monocyclic". Comprehensive Heterocyclic Chemistry III. 2.07: 389–428. doi:10.1016/B978-008044992-0.00207-8.

[2] Block, E; DeWang, M (1996). "Thietanes and Thietes: Monocyclic". Comprehensive Heterocyclic Chemistry II. 1.24: 773–802. doi:10.1016/B978-008096518-5.00024-1.

[3] Sievert, Thorbjörn; Laska, Matthias (2016). "Behavioral responses of CD-1 mice to six predator odor components". Chem. Senses. 41 (5): 399–406. doi:10.1093/chemse/bjw015. PMID 26892309.

[4] Brechbuhl, J; Moine, F; Klaey, M; Nenniger-Tosato, M; Hurni, N; Sporkert, F; Giroud, C; Broillet, MC (2013). "Mouse alarm pheromone shares structural similarity with predator scents". Proc. Natl. Acad. Sci. U.S.A. 110 (12): 4762–4767. doi:10.1073/pnas.1214249110. PMC 3607058. PMID 23487748.

[5] Li, Shengju; Ahmed, Lucky; Zhang, Ruina; Pan, Yi; Matsunami, Hiroaki; Burger, Jessica L; Block, Eric; Batista, Victor S; Zhuang, Hanyi (2016). "Smelling sulfur: Copper and silver regulate the response of human odorant receptor OR2T11 to low molecular weight thiols". Journal of the American Chemical Society. in press: 13281–13288. doi:10.1021/jacs.6b06983. PMID 27659093.