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2,4,6-Trichloroanisole

Names
Preferred IUPAC name 1,3,5-Trichloro-2-methoxybenzene
Other names 2,4,6-Trichloroanisole TCA 2,4,6-Trichloromethoxybenzene
Identifiers
CAS Number	87-40-1
3D model (JSmol)	Interactive image Interactive image
ChEBI	CHEBI:19333
ChemSpider	6620
ECHA InfoCard	100.001.585
EC Number	201-743-5
KEGG	C11510
PubChem CID	6884
RTECS number	MFCD00000588
UNII	31O3X41254
CompTox Dashboard (EPA)	DTXSID9073886
InChI InChI=1S/C7H5Cl3O/c1-11-7-5(9)2-4(8)3-6(7)10/h2-3H,1H3Key: WCVOGSZTONGSQY-UHFFFAOYSA-N InChI=1/C7H5Cl3O/c1-11-7-5(9)2-4(8)3-6(7)10/h2-3H,1H3Key: WCVOGSZTONGSQY-UHFFFAOYAT
SMILES COc1c(Cl)cc(Cl)cc1Cl Clc1cc(Cl)cc(Cl)c1OC
Properties
Chemical formula	C7H5Cl3O
Molar mass	211.47 g·mol
Melting point	60 to 62 °C (140 to 144 °F; 333 to 335 K)
Boiling point	140 °C (284 °F; 413 K) at 28 Torr
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302, H319, H413
Precautionary statements	P264, P270, P273, P280, P301+P312, P305+P351+P338, P330, P337+P313, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). N verify (what is  ?) Infobox references

2,4,6-Trichloroanisole (TCA) is an organic compound with the formula CH₃OC₆H₂Cl₃. It is the symmetric isomer 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 deteriorate the quality" of such products. It is also a component of some drinking waters. It has also been detected in blood samples.

Wine

As of 2000, TCA was considered the primary chemical compound responsible for the phenomenon of cork taint in wines, 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, which refers to a taste described as "medicinal, phenolic, or iodine-like". 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. 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. Species implicated include those of the genera Aspergillus, Penicillium, Actinomycetes, Botrytis (e.g. Botrytis cinerea), Rhizobium, or Streptomyces.

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.

Further reading

• Marsili, R. (2000). "Solid-Phase Microextraction: Food Technology Applications". In Wilson, Ian D. (ed.). Encyclopedia of Separation Science. New Yor, NY: Academic Press. pp. 4178–4190. doi:10.1016/B0-12-226770-2/06791-0. ISBN 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). Retrieved June 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 in cork taint.

See also

• 2,4,6-Tribromoanisole

References

1. ^ Takeuchi, Hiroko; Kato, Hiroyuki & Kurahashi, Takashi (2013-09-16). "2,4,6-Trichloroanisole is a Potent Suppressor of Olfactory Signal Transduction". Proceedings of the National Academy of Sciences. 110 (40): 16235–16240. Bibcode:2013PNAS..11016235T. doi:10.1073/pnas.1300764110. ISSN 1091-6490. PMC 3791788. PMID 24043819.{{cite journal}}: CS1 maint: multiple names: authors list (link)
2. ^ Jackson, Ron S. (2009). "Chapter 3: Olfactory Sensations". Wine tasting: a professional handbook. Food science and technology international series (2nd ed.). Academic Press. ISBN 978-0-12-374181-3.
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.
4. 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. PMID 11706375.{{cite journal}}: CS1 maint: multiple names: authors list (link)
5. Marsili, R. (2000). "Solid-Phase Microextraction: Food Technology Applications". In Wilson, Ian D. (ed.). Encyclopedia of Separation Science. New Yor, NY: Academic Press. pp. 4178–4190. doi:10.1016/B0-12-226770-2/06791-0. ISBN 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.
6. These include Central and South America.
7. ^ Spadone, 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 that 2,4,6-trichlorophenol is "the probable precursor of TCA".
8. Pereira, Helena (2007-01-01), Pereira, Helena (ed.), "Chapter 14 - Wine and cork", Cork, Amsterdam: Elsevier Science B.V., pp. 305–327, ISBN 978-0-444-52967-1, retrieved 2024-01-14
9. ^ 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". Journal of the Institute of Brewing. 121 (3): 411–417. doi:10.1002/jib.230.
10. Crane, Louise (22 March 2019). "Trichloroanisole: Cork taint". Chemistry World. Retrieved 2024-01-14.
11. 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)".
12. 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://ntp.niehs.nih.gov/go/roc15 DOI: https://doi.org/10.22427/NTP-OTHER-1003

• Chlorobenzene derivatives
• Phenol ethers