Misplaced Pages

:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and 2,4,6-Trichloroanisole: Difference between pages - Misplaced Pages

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
(Difference between pages)
Page 1
Page 2
Content deleted Content addedVisualWikitext
Revision as of 17:01, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 475927888 of page 2,4,6-Trichloroanisole for the Chem/Drugbox validation project (updated: 'CASNo').  Latest revision as of 19:32, 19 August 2024 edit Smokefoot (talk | contribs)Autopatrolled, Extended confirmed users, Pending changes reviewers, Rollbackers74,203 edits →Occurrence: | Add: bibcode, pages, issue, volume, journal, date, title, authors 1-5. | Use this tool. Report bugs. | #UCB_Gadget | Add: bibcode, pmid, pages, issue, volume, journal, date, title, authors 1-7. | Use this tool. Report bugs. | #UCB_Gadget 
Line 1: Line 1:
{{Short description|Chemical primarily responsible for cork taint in wines (TCA)}}
{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
{{chembox {{chembox
| Verifiedimages = changed | Verifiedimages = changed
| Verifiedfields = changed
⚫ | verifiedrevid = 443263598
| Watchedfields = changed
⚫ | Name = '''2,4,6-Trichloroanisole'''
⚫ | verifiedrevid = 477210787
⚫ | ImageFile_Ref = {{chemboximage|changed|??}}
| ImageFile = 2,4,6-Trichloroanisole.svg | Name = 2,4,6-Trichloroanisole
⚫ | ImageFile_Ref = {{chemboximage|correct|??}}
⚫ | ImageSize = 120px
| ImageFile = 2,4,6-TrichloroanisoleImproved.svg
⚫ | ImageName = Chemical structure of 2,4,6-trichloroanisole
⚫ | ImageSize = 150
| IUPACName = 2,4,6-Trichloroanisole
⚫ | ImageAlt = Chemical structure of 2,4,6-trichloroanisole
| OtherNames = TCA
⚫ | ImageFile1 = 2,4,6-Trichloroanisole-3D-balls.png
⚫ | Section1 = {{Chembox Identifiers
| ImageSize1 = 150
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ImageAlt1 = Ball-and-stick model of the 2,4,6-trichloroanisole molecule
| PIN = 1,3,5-Trichloro-2-methoxybenzene <!-- no substitution on anisole for PINs according to Subsection P-63.2.3 of ''Nomenclature of Organic Chemistry – IUPAC Recommendations and Preferred Names 2013 (Blue Book)'' -->
| OtherNames = 2,4,6-Trichloroanisole<br />TCA<br/>2,4,6-Trichloromethoxybenzene
⚫ |Section1={{Chembox Identifiers
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 19333 | ChEBI = 19333
| ChemSpiderID = 6620 | ChemSpiderID = 6620
| EC_number = 201-743-5
| KEGG_Ref = {{keggcite|correct|kegg}} | KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C11510 | KEGG = C11510
| PubChem = 6884
| InChI = 1/C7H5Cl3O/c1-11-7-5(9)2-4(8)3-6(7)10/h2-3H,1H3 | InChI = 1/C7H5Cl3O/c1-11-7-5(9)2-4(8)3-6(7)10/h2-3H,1H3
| SMILES1 = Clc1cc(Cl)cc(Cl)c1OC | SMILES1 = Clc1cc(Cl)cc(Cl)c1OC
Line 24: Line 31:
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = WCVOGSZTONGSQY-UHFFFAOYSA-N | StdInChIKey = WCVOGSZTONGSQY-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = <!-- blanked - oldvalue: 87-40-1 -->
| CASNo = 87-40-1
⚫ | SMILES = COc1c(Cl)cc(Cl)cc1Cl
| UNII_Ref = {{fdacite|correct|FDA}}
⚫ | RTECS = MFCD00000588
| UNII = 31O3X41254
⚫ | SMILES = COc1c(Cl)cc(Cl)cc1Cl
⚫ | RTECS = MFCD00000588
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| C=7 | H=5 | Cl=3 | O=1
| Formula = C<sub>7</sub>H<sub>5</sub>Cl<sub>3</sub>O
| Density =
| MolarMass = 211.47 g/mol
| Density = | MeltingPtC = 60 to 62
| BoilingPtC = 140
| MeltingPt = 60-62 °C
| BoilingPt = 140 °C at 28 torr | BoilingPt_notes = at 28 Torr
}} }}
| Section7 = {{Chembox Hazards |Section7={{Chembox Hazards
| RPhrases = {{R22}} {{R36}} | GHSPictograms = {{GHS07}}
| GHSSignalWord = Warning
| SPhrases = {{S26}}
| HPhrases = {{H-phrases|302|319|413}}
| PPhrases = {{P-phrases|264|270|273|280|301+312|305+351+338|330|337+313|501}}
}} }}
}} }}
'''2,4,6-Trichloroanisole''' ('''TCA''') is an ] with the formula {{chem2|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.<ref name = TakeuchiPNAS2013>{{Cite journal| doi = 10.1073/pnas.1300764110| issn = 1091-6490| author = Takeuchi, Hiroko; Kato, Hiroyuki & Kurahashi, Takashi | title = 2,4,6-Trichloroanisole is a Potent Suppressor of Olfactory Signal Transduction| journal = Proceedings of the National Academy of Sciences| date = 2013-09-16| volume=110| issue = 40| pages = 16235–16240| pmid=24043819| pmc=3791788| bibcode = 2013PNAS..11016235T| doi-access = free}}{{primary source inline|date = June 2023}}</ref><ref name=":0">{{Cite book |last=Jackson |first=Ron S. |title=Wine tasting: a professional handbook |date=2009 |publisher=Academic Press |isbn=978-0-12-374181-3 |edition=2nd |series=Food science and technology international series |language=En |chapter=Chapter 3: Olfactory Sensations}}</ref> It is also a component of some drinking waters.<ref>{{cite journal|doi= 10.1016/0043-1354(95)00173-5|title= Taste and odour threshold concentrations of potential potable water contaminants|date= 1996|last1= Young|first1= W.F.|last2= Horth|first2= H.|last3= Crane|first3= R.|last4= Ogden|first4= T.|last5= Arnott|first5= M.|journal= Water Research|volume= 30|issue= 2|pages= 331–340|bibcode= 1996WatRe..30..331Y}}</ref> It has also been detected in blood samples.<ref>{{cite journal |doi=10.1007/s002440010298 |title=Identification of Hydroxylated PCB Metabolites and Other Phenolic Halogenated Pollutants in Human Blood Plasma |date=2002 |last1=Hovander, t. Malmberg, m. Athanasia |first1=L. |last2=Malmberg |first2=T. |last3=Athanasiadou |first3=M. |last4=Athanassiadis |first4=I. |last5=Rahm |first5=S. |last6=Bergman |first6=A. |last7=Wehler |first7=E. K. |journal=Archives of Environmental Contamination and Toxicology |volume=42 |issue=1 |pages=105–117 |pmid=11706375 |bibcode=2002ArECT..42..105H }}</ref>
===Wine===
As of 2000, TCA was considered the primary chemical compound responsible for the phenomenon of ] in wines,<ref>{{cite book | author = Marsili, R. | date = 2000 | chapter = Solid-Phase Microextraction: Food Technology Applications | title = Encyclopedia of Separation Science | editor = Wilson, Ian D. | location = New Yor, NY | publisher = Academic Press | chapter-url = https://www.sciencedirect.com/science/article/abs/pii/B0122267702067910 | doi = 10.1016/B0-12-226770-2/06791-0 | pages = 4178–4190 | isbn = 9780122267703 | quote = 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.}}</ref><ref name = TakeuchiPNAS2013/> and it has an unpleasant earthy, musty and moldy smell.<ref name=":0" />

===Coffee===
TCA has also been suggested as cause of the "Rio defect" in coffees from ] and other parts of the world,<ref>These include Central and South America.{{fact|date = June 2023}}</ref> which refers to a taste described as "medicinal, phenolic, or iodine-like".<ref name = SpadoneJAFC1990/> In investigation of the mechanism of its role in producing off-flavor effects, it was found to "attenuate olfactory transduction by suppressing ], without evoking odorant responses."<ref name = TakeuchiPNAS2013/>

==Formation==
TCA is formed by the methylation of ].<ref>{{Citation |last=Pereira |first=Helena |title=Chapter 14 - Wine and cork |date=2007-01-01 |url=https://www.sciencedirect.com/science/article/pii/B9780444529671500169 |work=Cork |pages=305–327 |editor-last=Pereira |editor-first=Helena |access-date=2024-01-14 |place=Amsterdam |publisher=Elsevier Science B.V. |isbn=978-0-444-52967-1}}</ref><ref name = SpadoneJAFC1990>{{Cite journal | author = Spadone, Jean Claude; Takeoka, Gary & Liardon, Remy| title = Analytical Investigation of Rio Off-Flavor in Green Coffee| journal = Journal of Agricultural and Food Chemistry| doi = 10.1021/jf00091a050 | year = 1990| volume = 38| pages = 226–233}} Note, at best, this source states that ] is "the probable precursor of TCA".</ref> More generally, it may be produced when naturally occurring airborne ] and ] are presented with ] ], which they then convert into chlorinated anisole ].<ref name=":1">{{Cite journal |last=Cravero |first=Maria Carla |last2=Bonello |first2=Federica |last3=Pazo Alvarez |first3=Maria del Carmen |last4=Tsolakis |first4=Christos |last5=Borsa |first5=Daniela |date=24 June 2015 |title=The sensory evaluation of 2,4,6-trichloroanisole in wines: The sensory evaluation of 2,4,6-trichloroanisole in wines |url=https://onlinelibrary.wiley.com/doi/10.1002/jib.230 |journal=Journal of the Institute of Brewing |language=en |volume=121 |issue=3 |pages=411–417 |doi=10.1002/jib.230}}</ref> Species implicated include those of the genera '']'', '']'', '']'', '']'' (e.g. '']''), '']'', or '']''.<ref>{{Cite web |last=Crane |first=Louise |title=Trichloroanisole: Cork taint |url=https://www.chemistryworld.com/podcasts/trichloroanisole-cork-taint/3010280.article |access-date=2024-01-14 |website=Chemistry World |language=en |publication-date=22 March 2019}}</ref><ref>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)".</ref><ref name=":1" />

The ] precursor, ], is used as a ]; more generally, related compounds can originate as contaminants found in some ]s and wood ]s, or as by-products of the ] process used to ] or ] wood, paper, and other materials.<ref>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. <nowiki>https://ntp.niehs.nih.gov/go/roc15</nowiki>

DOI: <nowiki>https://doi.org/10.22427/NTP-OTHER-1003</nowiki></ref>

==Further reading==
* {{cite book | author = Marsili, R. | date = 2000 | chapter = Solid-Phase Microextraction: Food Technology Applications | title = Encyclopedia of Separation Science | editor = Wilson, Ian D. | location = New Yor, NY | publisher = Academic Press | chapter-url = https://www.sciencedirect.com/science/article/abs/pii/B0122267702067910 | doi = 10.1016/B0-12-226770-2/06791-0 | pages = 4178–4190 | isbn = 9780122267703 | quote = 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.}}
* {{cite web | author = Science Direct Staff | date = June 2023 | title = 2-4-6-Trichloroanisole | format = ''Science Direct'' citation sample/listing | url = https://www.sciencedirect.com/topics/chemistry/2-4-6-trichloroanisole | access-date = June 26, 2023}}
* {{cite journal | author = Buser, H.R.; Zanier, C. & Tanner, H.| title = Identification of 2,4,6-Trichloroanisole as a Potent Compound Causing Cork Taint in Wine. | journal = Journal of Agricultural and Food Chemistry| doi = 10.1021/jf00110a037| year = 1982 | volume = 30 | issue = 2 | pages = 359–362}} An early primary research report on the role of TCA in ].

== See also ==
* ]

==References==
{{Reflist}}

{{DEFAULTSORT:Trichloroanisole, 2,4,6-}}
]
]