2,4,6-Trichloroanisole
Names | |
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Preferred IUPAC name
1,3,5-Trichloro-2-methoxybenzene | |
Other names
2,4,6-Trichloroanisole
TCA 2,4,6-Trichloromethoxybenzene | |
Identifiers | |
3D model (
JSmol ) |
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ChEBI | |
ChemSpider | |
ECHA InfoCard
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100.001.585 |
EC Number |
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KEGG | |
PubChem CID
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RTECS number
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C7H5Cl3O | |
Molar mass | 211.47 g·mol−1 |
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: | |
Warning | |
H302, H319, H413 | |
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 [77 °F], 100 kPa).
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2,4,6-Trichloroanisole (TCA) is a chemical compound that represents one of the strongest of off-flavors, substances "generated naturally in foods/beverages [that considerably] deteriorate the quality" of such products.[1][2] As of 2000, TCA was considered the primary chemical compound responsible for the phenomenon of cork taint in wines,[3][1] and it has an unpleasant earthy, musty and moldy smell.[2]
Chemically, TCA is a
The
TCA has also been suggested as cause of the "Rio defect" in coffees from Brazil and other parts of the world,[10] which refers to a taste described as "medicinal, phenolic, or iodine-like".[5] 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."[1]
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. 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
References
- ^ PMID 24043819.]
{{cite journal}}
: CS1 maint: multiple names: authors list (link)[non-primary source needed - ^ ISBN 978-0-12-374181-3.
- 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.
- ISBN 978-0-444-52967-1, retrieved 2024-01-14
- ^ 2,4,6-trichlorophenolis "the probable precursor of TCA".
- ^ doi:10.1002/jib.230.
- ^ Crane, Louise (22 March 2019). "Trichloroanisole: Cork taint". Chemistry World. Retrieved 2024-01-14.
- ^ 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://ntp.niehs.nih.gov/go/roc15 DOI: https://doi.org/10.22427/NTP-OTHER-1003
- ^ These include Central and South America.[citation needed]