2,4,6-Trichloroanisole (TCA) is anorganic compound with the formulaCH3OC6H2Cl3. It is one of several isomers of trichloroanisole. It is a colorless solid.
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.[1][2] It is also a component of some drinking waters.[3] It has also been detected in blood samples.[4]
As of 2000, TCA was considered the primary chemical compound responsible for the phenomenon ofcork taint in wines,[5][1] and it has an unpleasant earthy, musty and moldy smell.[2]
TCA has also been suggested as cause of the "Rio defect" in coffees fromBrazil and other parts of the world,[6] which refers to a taste described as "medicinal, phenolic, or iodine-like".[7] In investigation of the mechanism of its role in producing off-flavor effects, it was found to "attenuate olfactory transduction by suppressingcyclic nucleotide-gated channels, without evoking odorant responses."[1]
Marsili, R. (2000)."Solid-Phase Microextraction: Food Technology Applications". In Wilson, Ian D. (ed.).Encyclopedia of Separation Science. New York, NY: Academic Press. pp. 4178–4190.doi:10.1016/B0-12-226770-2/06791-0.ISBN9780122267703.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). RetrievedJune 26, 2023.
Buser, H.R.; Zanier, C. & Tanner, H. (1982). "Identification of 2,4,6-Trichloroanisole as a Potent Compound Causing Cork Taint in Wine".Journal of Agricultural and Food Chemistry.30 (2):359–362.doi:10.1021/jf00110a037.{{cite journal}}: CS1 maint: multiple names: authors list (link) An early primary research report on the role of TCA incork taint.
^abJackson, Ron S. (2009). "Chapter 3: Olfactory Sensations".Wine tasting: a professional handbook. Food science and technology international series (2nd ed.). Academic Press.ISBN978-0-12-374181-3.
^Young, W.F.; Horth, H.; Crane, R.; Ogden, T.; Arnott, M. (1996). "Taste and odour threshold concentrations of potential potable water contaminants".Water Research.30 (2):331–340.Bibcode:1996WatRe..30..331Y.doi:10.1016/0043-1354(95)00173-5.
^Hovander, t. Malmberg, m. Athanasia, L.; Malmberg, T.; Athanasiadou, M.; Athanassiadis, I.; Rahm, S.; Bergman, A.; Wehler, E. K. (2002). "Identification of Hydroxylated PCB Metabolites and Other Phenolic Halogenated Pollutants in Human Blood Plasma".Archives of Environmental Contamination and Toxicology.42 (1):105–117.Bibcode:2002ArECT..42..105H.doi:10.1007/s002440010298.PMID11706375.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^Marsili, R. (2000)."Solid-Phase Microextraction: Food Technology Applications". In Wilson, Ian D. (ed.).Encyclopedia of Separation Science. New York, NY: Academic Press. pp. 4178–4190.doi:10.1016/B0-12-226770-2/06791-0.ISBN9780122267703.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.
^abSpadone, Jean Claude; Takeoka, Gary & Liardon, Remy (1990). "Analytical Investigation of Rio Off-Flavor in Green Coffee".Journal of Agricultural and Food Chemistry.38:226–233.doi:10.1021/jf00091a050.{{cite journal}}: CS1 maint: multiple names: authors list (link) Note, at best, this source states that2,4,6-trichlorophenol is "the probable precursor of TCA".
^With 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)".
^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. [https://web.archive.org/web/20220118142253/https://ntp.niehs.nih.gov/whatwestudy/assessments/cancer/roc/index.html?utm_source=direct&utm_medium=prod&utm_campaign=ntpgolinks&utm_term=roc15 nih.gov]DOI: https://doi.org/10.22427/NTP-OTHER-1003
