2-sec-butyl-4,5-dihydrothiazole

Lehman-McKeeman L., Caudill D., Rodriguez P. and Eddy C. (1998). 2-sec-butyl-4,5-dihydrothiazole is a ligand for mouse urinary protein and rat alpha 2p-globulin physiological and toxicological relevance. Toxicol Appl Pharmacol 149, 32-40. 

Fig. 1.3 Illustration of the mass spectra for the GC-MS TIC compound eluting at retention time of 23.4 min (2-sec-butyl-4,5-dihydrothiazole). A high resolution MS spectrum, B low resolution MS spectrum...

Zidek, L., Stone, M. J., Lato, S. M., Pagel, M. D., Miao, Z., Ellington, A. D. and Novotny, M. V. (1999) NMR mapping of the recombinant mouse major urinary protein I binding site occupied by the pheromone 2-sec-butyl-4,5-dihydrothiazole. Biochemistry 38, 9850-61. 

In 1984, 3,4-dehydro-exo-brevicomin (99, Figure 4.50) and 2-sec -butyl-4,5-dihydrothiazole (100) were isolated by Novotny and coworkers from the urine of the male house mouse (Mus musculus) as pheromone components.92 They act, synergistically, in promoting intermale aggression, sex attraction, and estrus synchronization in female mice. It was later found that the natural components are ( R,5S,lR)-99 and (S)-100. Additional achiral compounds 101 and 102 were also identified as possible pheromone components. 

Figure 4.50 Synthesis of (1 R,5S,7R)-3,4-dehydro-exo-brevicomin and (S)-2-sec-butyl-4,5-dihydrothiazole, the mouse pheromone...

Figure 4. MUP-bound ligands. These molecules have all been identified bound to MUPs. They are the two naturally occurring ligands, 2-sec butyl-4,5 dihydrothiazole and 3,4-dehydro-exo-brevicomin, and menadione, the protein-bound ligand observed in urine posts, used as a competitive displacer for behavioural studies.

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