87-40-1
Chemical Structure
Tyrene
Synonym(s): 2,4,6-Trichloroanisole
- CAS. Nr.: 87-40-1
- Formula:C7H5Cl3O
- Molecular Weight:211.47
IUPAC Name: 1,3,5-trichloro-2-methoxybenzene
InChIKey: WCVOGSZTONGSQY-UHFFFAOYSA-N
SMILES: ClC1=CC(Cl)=C(OC)C(Cl)=C1
Biological Activity: Tyrene (2,4,6-Trichloroanisole) is an off-flavor compound, cyclic nucleotide-gated (CNG) channel inhibitor, and olfactory transduction attenuator. Tyrene is formed by microbial O-methylation of 2,4,6-trichlorophenol. Tyrene inhibits channel activity in olfactory receptor cells by partitioning into the plasma membrane lipid bilayer, and also suppresses odorant- and cAMP-induced currents in individual olfactory receptor cells. Tyrene causes cork taint in wine. Tyrene also produces off-flavors in potato chips, dried fruits, coffee, and drinking water[1][2][3].
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Tyrene | Tyrene (2,4,6-Trichloroanisole) is an off-flavor compound, cyclic nucleotide-gated (CNG) channel inhibitor, and olfactory transduction attenuator. Tyrene is formed by microbial O-methylation of 2,4,6-trichlorophenol. Tyrene inhibits channel activity in olfactory receptor cells by partitioning into the plasma membrane lipid bilayer, and also suppresses odorant- and cAMP-induced currents in individual olfactory receptor cells. Tyrene causes cork taint in wine. Tyrene also produces off-flavors in potato chips, dried fruits, coffee, and drinking water. | |||||||||||||||||||||
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2,4,6-Trichloroanisole-d5 | 99.4% | 2,4,6-Trichloroanisole-d5 is the deuterium labeled 2,4,6-Trichloroanisole. | ||||||||||||||||||||
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References
- [1]. Takeuchi H, et al. 2,4,6-trichloroanisole is a potent suppressor of olfactory signal transduction. Proc Natl Acad Sci U S A. 2013 Oct 1;110(40):16235-40. [Content Brief]
- [2]. Taylor MK, et al. Supercritical fluid extraction of 2,4,6-trichloroanisole from cork stoppers. J Agric Food Chem. 2000 Jun;48(6):2208-11. [Content Brief]
- [3]. Alvarez-Rodríguez ML, et al. Cork taint of wines: role of the filamentous fungi isolated from cork in the formation of 2,4,6-trichloroanisole by o methylation of 2,4,6-trichlorophenol. Appl Environ Microbiol. 2002 Dec;68(12):5860-9. [Content Brief]
