2-sec-Butyl-4,5-dihydrothiazole

changed 477344176 2-sec-Butyl-4,5-dihydrothiazole162148 2-sec-Butyl-4,5-dihydrothiazole.svg 180px 2-(Butan-2-yl)-4,5-dihydro-1,3-thiazole SBT 2-(1-methylpropyl)-2-thiazoline 2-sec-butyl-2-thiazoline changed ?? 56367-27-2 correct FDA LE756QG3F5 correct chemspider 1S/C7H13NS/c1-3-6(2)7-8-4-5-9-7/h6H,3-5H2,1-2H3 correct chemspider SAWWKXMIPYUIBW-UHFFFAOYSA-N 162148 correct chemspider 142398 CCC(C)C1=NCCS1 InChI=1S/C7H13NS/c1-3-6(2)7-8-4-5-9-7/h6H,3-5H2,1-2H3 SAWWKXMIPYUIBW-UHFFFAOYSA-N 7 13 1 1 1.06 g/cm3 193 70.5 Dihydrothiazole (thiazoline) 2-sec-Butyl-4,5-dihydrothiazole (also known as SBT) is a thiazoline compound with the molecular formula C7H13NS. A volatile pheromone found in rodents such as mice and rats, SBT is excreted in the urine and promotes aggression amongst males while inducing synchronized estrus in females. 10.1002/pro.426 High resolution X-ray structures of mouse major urinary protein nasal isoform in complex with pheromones 2010 Perez-Miller Samantha Zou Qin Novotny Milos V. Hurley Thomas D. Protein Science 19 8 1469–79 20509168 2923500 Binding to MUP Mouse major urinary proteins (MUPs) are responsible for binding to hydrophobic ligands such as the pheromone SBT. SBT binds within MUP-I's barrel-shaped active site, forming a hydrogen bond with a water molecule within the active site, which in turn is stabilized by forming hydrogen bonds with residue Phe56 and another water molecule; this second water molecule also forms hydrogen bonds to residues in the active site, namely Leu58 and Thr39. SBT also forms van der Waals forces with several of MUP-I's residues, including Ala121, Leu123, Leu134, Leu72, Val100, and Phe108. When bound, MUP safely carries SBT through the aqueous environment; once the protein-ligand complex is excreted in the urine, MUP helps prevent SBT decomposition and controls the slow release of SBT over a prolonged period of time, resulting in the physiological and behavioral responses of animals who come into contact with the pheromone. 10.1110/ps.52201 Structural basis of pheromone binding to mouse major urinary protein (MUP-I) 2001 Timm David E. Baker L.J. Mueller Heather Zidek Lukas Novotny Milos V. Protein Science 10 5 997–1004 11316880 2374202 Synthesis SBT can be produced from 3-(2-aminoethanethio)-4-methylhex-2-enenitrile; 10.1016/S0040-4020(01)88457-X Allenes-41 the addition of thiols to allenyl- and phenylpropynyl- nitrile and the formation of thiazolines and benzothiazoles 1984 Landor S Tetrahedron 40 11 2141 however, it is also possible to synthesize SBT from ethanolamine and 2-methylbutanoic acid, using Lawesson's reagent and microwave irradiation. 10.1016/j.tet.2008.07.027 Straightforward microwave-assisted synthesis of 2-thiazolines using Lawesson's reagent under solvent-free conditions 2008 Seijas Julio A. Vázquez-Tato M. Pilar Crecente-Campo José Tetrahedron 64 39 9280 References Category:Mammalian pheromones Category:Thiazolines Category:Sec-Butyl compounds