2,4,6-Trichloroanisole

Chemical primarily responsible for cork taint in wines (TCA) changed changed changed 477210787 2,4,6-Trichloroanisole correct ?? 2,4,6-TrichloroanisoleImproved.svg 150 Chemical structure of 2,4,6-trichloroanisole 2,4,6-Trichloroanisole-3D-balls.png 150 Ball-and-stick model of the 2,4,6-trichloroanisole molecule 1,3,5-Trichloro-2-methoxybenzene 2,4,6-TrichloroanisoleTCA2,4,6-Trichloromethoxybenzene correct chemspider correct EBI 19333 6620 201-743-5 correct kegg C11510 6884 1/C7H5Cl3O/c1-11-7-5(9)2-4(8)3-6(7)10/h2-3H,1H3 Clc1cc(Cl)cc(Cl)c1OC WCVOGSZTONGSQY-UHFFFAOYAT correct chemspider 1S/C7H5Cl3O/c1-11-7-5(9)2-4(8)3-6(7)10/h2-3H,1H3 correct chemspider WCVOGSZTONGSQY-UHFFFAOYSA-N correct CAS 87-40-1 correct FDA 31O3X41254 COc1c(Cl)cc(Cl)cc1Cl MFCD00000588 7 5 3 1 60 to 62 140 at 28 Torr 07 Warning 302 319 413 264 270 273 280 301+312 305+351+338 330 337+313 501 2,4,6-Trichloroanisole (TCA) is an organic compound with the formula CH3OC6H2Cl3. It is one of several isomers of trichloroanisole. It is a colorless solid. Occurrence 2,4,6-Trichloroanisole represents one of the strongest of off-flavors, substances "generated naturally in foods/beverages [that considerably] deteriorate the quality" of such products. 10.1073/pnas.1300764110 1091-6490 Takeuchi, Hiroko; Kato, Hiroyuki & Kurahashi, Takashi 2,4,6-Trichloroanisole is a Potent Suppressor of Olfactory Signal Transduction Proceedings of the National Academy of Sciences 2013-09-16 110 40 16235–16240 24043819 3791788 2013PNAS..11016235T free June 2023Jackson Ron S. Wine tasting: a professional handbook 2009 Academic Press 978-0-12-374181-3 2nd Food science and technology international series En Chapter 3: Olfactory Sensations It is also a component of some drinking waters. 10.1016/0043-1354(95)00173-5 Taste and odour threshold concentrations of potential potable water contaminants 1996 Young W.F. Horth H. Crane R. Ogden T. Arnott M. Water Research 30 2 331–340 1996WatRe..30..331Y It has also been detected in blood samples.10.1007/s002440010298 Identification of Hydroxylated PCB Metabolites and Other Phenolic Halogenated Pollutants in Human Blood Plasma 2002 Hovander, t. Malmberg, m. Athanasia L. Malmberg T. Athanasiadou M. Athanassiadis I. Rahm S. Bergman A. Wehler E. K. Archives of Environmental Contamination and Toxicology 42 1 105–117 11706375 2002ArECT..42..105H Wine As of 2000, TCA was considered the primary chemical compound responsible for the phenomenon of cork taint in wines, Marsili, R. 2000 Solid-Phase Microextraction: Food Technology Applications Encyclopedia of Separation Science Wilson, Ian D. New York, NY Academic Press https://www.sciencedirect.com/science/article/abs/pii/B0122267702067910 10.1016/B0-12-226770-2/06791-0 4178–4190 9780122267703 Over the last two decades, the incidence of mouldy and musty off-flavours in cork-sealed wines has increased significantly. 2,4,6-Trichloroanisole (TCA) has been identified as the primary chemical responsible for cork taint. The human olfactometry threshold for TCA is 4–10 ng L−1 in white wine and 50 ng L−1 in red wine. In the case of wine, a worldwide loss of roughly US$1 billion per year is attributed to cork taint. and it has an unpleasant earthy, musty and moldy smell. Coffee TCA has also been suggested as cause of the "Rio defect" in coffees from Brazil and other parts of the world,These include Central and South America. June 2023 which refers to a taste described as "medicinal, phenolic, or iodine-like". Spadone, Jean Claude; Takeoka, Gary & Liardon, Remy Analytical Investigation of Rio Off-Flavor in Green Coffee Journal of Agricultural and Food Chemistry 10.1021/jf00091a050 1990 38 226–233 Note, at best, this source states that 2,4,6-trichlorophenol is "the probable precursor of TCA". In investigation of the mechanism of its role in producing off-flavor effects, it was found to "attenuate olfactory transduction by suppressing cyclic nucleotide-gated channels, without evoking odorant responses." Formation TCA is formed by the methylation of 2,4,6-trichlorophenol.Pereira Helena Chapter 14 - Wine and cork 2007-01-01 https://www.sciencedirect.com/science/article/pii/B9780444529671500169 Cork 305–327 Pereira Helena 2024-01-14 Amsterdam Elsevier Science B.V. 978-0-444-52967-1 More generally, it may be produced when naturally occurring airborne fungi and bacteria are presented with chlorinated phenolic compounds, which they then convert into chlorinated anisole derivatives.Cravero Maria Carla Bonello Federica Pazo Alvarez Maria del Carmen Tsolakis Christos Borsa Daniela 24 June 2015 The sensory evaluation of 2,4,6-trichloroanisole in wines: The sensory evaluation of 2,4,6-trichloroanisole in wines https://onlinelibrary.wiley.com/doi/10.1002/jib.230 Journal of the Institute of Brewing en 121 3 411–417 10.1002/jib.230 free Species implicated include those of the genera Aspergillus, Penicillium, Actinomycetes, Botrytis (e.g. Botrytis cinerea), Rhizobium, or Streptomyces.Crane Louise Trichloroanisole: Cork taint https://www.chemistryworld.com/podcasts/trichloroanisole-cork-taint/3010280.article 2024-01-14 Chemistry World en 22 March 2019With regard to circumstantial evidence, Spodone, et al., op. cit., note that Rio off-flavor is associated with "beans heavily infested with various fungi (Aspergilli, Fusaria, Penicillia, Rhizopus, etc.) and bacteria (Lactobacilli, Streptrococci)". The chlorophenol precursor, 2,4,6-trichlorophenol, is used as a fungicide; more generally, related compounds can originate as contaminants found in some pesticides and wood preservatives, or as by-products of the chlorine bleaching process used to sterilize or bleach wood, paper, and other materials.NTP (National Toxicology Program). 2021. "2,4,6-Trichlorophenol", Report on Carcinogens, Fifteenth Edition. Research Triangle Park, NC: U.S. Department of Health and Human Services, Public Health Service nih.gov DOI: https://doi.org/10.22427/NTP-OTHER-1003 Further reading Marsili, R. 2000 Solid-Phase Microextraction: Food Technology Applications Encyclopedia of Separation Science Wilson, Ian D. New York, NY Academic Press https://www.sciencedirect.com/science/article/abs/pii/B0122267702067910 10.1016/B0-12-226770-2/06791-0 4178–4190 9780122267703 Over the last two decades, the incidence of mouldy and musty off-flavours in cork-sealed wines has increased significantly. 2,4,6-Trichloroanisole (TCA) has been identified as the primary chemical responsible for cork taint. The human olfactometry threshold for TCA is 4–10 ng L−1 in white wine and 50 ng L−1 in red wine. In the case of wine, a worldwide loss of roughly US$1 billion per year is attributed to cork taint. Science Direct Staff June 2023 2-4-6-Trichloroanisole Science Direct citation sample/listing https://www.sciencedirect.com/topics/chemistry/2-4-6-trichloroanisole June 26, 2023 Buser, H.R.; Zanier, C. & Tanner, H. Identification of 2,4,6-Trichloroanisole as a Potent Compound Causing Cork Taint in Wine. Journal of Agricultural and Food Chemistry 10.1021/jf00110a037 1982 30 2 359–362 An early primary research report on the role of TCA in cork taint. See also 2,4,6-Tribromoanisole References Category:Chlorobenzene derivatives Category:Phenol ethers