| Revision as of 12:28, 10 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 468365098 of page Tert-Butylhydroquinone for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 16:14, 11 September 2024 edit Citation bot (talk | contribs)Bots5,391,720 edits Added bibcode. | Use this bot. Report bugs. | Suggested by Abductive | Category:E-number additives | #UCB_Category 151/313 |
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{{distinguish|tbqh}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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| Verifiedfields = changed |
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| Verifiedfields = changed |
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| Watchedfields = changed |
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| Watchedfields = changed |
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| verifiedrevid = 414695654 |
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| verifiedrevid = 470602935 |
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| Name = ''tert''-Butylhydroquinone |
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| Name = ''tert''-Butylhydroquinone |
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| ImageFile = Tert-butylhydroquinone.png |
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| ImageFile = tert-Butylhydroquinone-Skeletal.svg |
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| ImageSize = 200px |
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| ImageSize = 200px |
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| ImageName = Chemical structure of ''tert''-butylhydroquinone |
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| ImageName = Chemical structure of ''tert''-butylhydroquinone |
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| IUPACName = 2-(1,1-Dimethylethyl)-1,4-benzenediol |
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| PIN = 2-''tert''-Butylbenzene-1,4-diol |
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| OtherNames = TBHQ(i) |
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| OtherNames = TBHQ(i) |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| DrugBank_Ref = {{drugbankcite|changed|drugbank}} |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = DB07726 |
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| DrugBank = DB07726 |
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| SMILES = Oc1ccc(O)cc1C(C)(C)C |
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| SMILES = Oc1ccc(O)cc1C(C)(C)C |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 15235 |
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| ChemSpiderID = 15235 |
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| PubChem = 16043 |
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| PubChem = 16043 |
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| InChI = 1/C10H14O2/c1-10(2,3)8-6-7(11)4-5-9(8)12/h4-6,11-12H,1-3H3 |
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| InChI = 1/C10H14O2/c1-10(2,3)8-6-7(11)4-5-9(8)12/h4-6,11-12H,1-3H3 |
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| InChIKey = BGNXCDMCOKJUMV-UHFFFAOYAP |
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| InChIKey = BGNXCDMCOKJUMV-UHFFFAOYAP |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = 242080 |
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| ChEMBL = 242080| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI = 78886 |
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| EINECS = 217-752-2 |
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| UNII = C12674942B |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C10H14O2/c1-10(2,3)8-6-7(11)4-5-9(8)12/h4-6,11-12H,1-3H3 |
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| StdInChI = 1S/C10H14O2/c1-10(2,3)8-6-7(11)4-5-9(8)12/h4-6,11-12H,1-3H3 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 1948-33-0 |
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| CASNo = 1948-33-0 |
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| RTECS = |
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| RTECS = |
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}} |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=10|H=14|O=2 |
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| C=10|H=14|O=2 |
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| Appearance = Tan powder |
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| Appearance = Tan powder |
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| Density = 1.050 g/mL |
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| Density = 1.050 g/mL |
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| Solubility = Slightly Soluble |
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| Solubility = Slightly soluble |
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| MeltingPtCL = 127 |
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| MeltingPtC = 127 to 129 |
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| BoilingPtC = 273 |
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| MeltingPtCH = 129 |
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| pKa = 10.80±0.18 |
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| BoilingPtC = 273 |
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| ⚫ |
| pKa = 10.80±0.18 |
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}} |
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}} |
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| Section3 = {{Chembox Structure |
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|Section3={{Chembox Structure |
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| Dipole = |
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| Dipole = |
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| Section7 = {{Chembox Hazards |
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|Section7={{Chembox Hazards |
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| ExternalMSDS = |
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| ExternalSDS = |
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| MainHazards = Harmful |
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| MainHazards = Harmful |
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| FlashPt = 171 °C |
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| FlashPtC = 171 |
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| RPhrases = {{R22}} |
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| GHSPictograms = {{GHS07}}{{GHS09}} |
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| GHSSignalWord = Warning |
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| SPhrases = {{S26}} {{S27}} {{S28}} |
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| HPhrases = {{H-phrases|302|312|315|317|319|335|400}} |
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| PPhrases = {{P-phrases|261|264|270|271|272|273|280|301+312|302+352|304+340|305+351+338|312|321|322|330|332+313|333+313|337+313|362|363|391|403+233|405|501}} |
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}} |
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| Section8 = {{Chembox Related |
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|Section8={{Chembox Related |
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| OtherCpds = ] (BHA)<br />] (TBC) |
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| OtherCompounds = ] (BHA)<br />] (TBC) |
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'''''tert''-Butylhydroquinone'''{{DISPLAYTITLE:''tert''-Butylhydroquinone}} ('''TBHQ''', '''tertiary butylhydroquinone''') is a synthetic ] ] which is a type of ]. It is a derivative of ], substituted with a ''tert''-] group. |
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== Applications == |
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=== Food preservative === |
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In foods, TBHQ is used as a ] for unsaturated ]s and many edible animal fats. It does not cause discoloration even in the presence of iron, and does not change flavor or odor of the material to which it is added.<ref name=OBrien/> It can be combined with other preservatives such as ] (BHA). As a ], its ] is '''E319'''. It is added to a wide range of foods. Its primary advantage is extending storage life.<ref name=OBrien>''Fats and oils: formulating and processing for applications'', Richard D. O'Brien, page 168</ref> |
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===Other=== |
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In perfumery, it is used as a fixative to lower the evaporation rate and improve stability. |
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It is used industrially as a ] to inhibit autopolymerization of ]s. |
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It is used as an antioxidant in biodiesel.<ref name=Almeida>{{Cite journal | doi = 10.1016/j.fuel.2011.06.056| title = Behaviour of the antioxidant tert-butylhydroquinone on the storage stability and corrosive character of biodiesel| journal = Fuel| volume = 90| issue = 11| pages = 3480–3484| year = 2011| last1 = Almeida| first1 = Eduardo S.| last2 = Portela| first2 = Flaysner M.| last3 = Sousa| first3 = Raquel M.F.| last4 = Daniel| first4 = Daniela| last5 = Terrones| first5 = Manuel G.H.| last6 = Richter| first6 = Eduardo M.| last7 = Muñoz| first7 = Rodrigo A.A.| doi-access = free| bibcode = 2011Fuel...90.3480A}}</ref> |
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It is also added to ]es, ]s, ]s, and oil-field additives. |
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==Safety and regulation== |
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The ] (EFSA) and the ] (FDA)<ref>. ]. Retrieved June 11, 2016.</ref> have evaluated TBHQ and determined that it is safe to consume at the concentration allowed in foods.<ref name="EFSA">. ], 12 July 2004</ref> The FDA<ref name="CFR"></ref> and European Union<ref name="EFSA" /> both set an upper limit of 0.02% (200mg/kg) of the oil or fat content in foods. At very high doses, it has some negative health effects on lab animals, such as producing precursors to stomach tumors and damage to DNA.<ref> - safety summary from The International Programme on Chemical Safety</ref> |
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A number of studies have shown that prolonged exposure to very high doses of TBHQ may be carcinogenic,<ref>{{cite journal |vauthors=Gharavi N, El-Kadi A |title=tert-Butylhydroquinone is a novel aryl hydrocarbon receptor ligand |journal=Drug Metab Dispos |volume=33 |issue=3 |pages=365–72 |year=2005 |pmid=15608132 |doi=10.1124/dmd.104.002253|s2cid=5963778 }}</ref> especially for stomach tumors.<ref name=mctt>{{Cite journal | last1 = Hirose| first1 = Masao|last2 = Yada| first2 = Hideaki| last3 = Hakoi| first3 = Kazuo| last4 = Takahashi|first4 = Satoru| last5 = Ito| first5 = Nobuyuki| title = Modification of carcinogenesis by -tocopherol, t-butylhydro-quinone, propyl gallate and butylated hydroxytoluene in a rat multi-organ carcinogenesis model|journal = ]| volume = 14| issue = 1| pages = 2359–2364| publisher = ]| doi = 10.1093/carcin/14.11.2359|pmid=8242867|display-authors=etal| year = 1993}}</ref> Other studies, however, have shown opposite effects including inhibition against ]-induced carcinogenesis (by depression of metabolic activation) for TBHQ and other phenolic antioxidants (TBHQ was one of several, and not the most potent).<ref>{{cite journal |vauthors=Hirose M, Takahashi S, Ogawa K, Futakuchi M, Shirai T, Shibutani M, Uneyama C, Toyoda K, Iwata H |title=Chemoprevention of heterocyclic amine-induced carcinogenesis by phenolic compounds in rats |journal=Cancer Lett |volume=143 |issue=2 |pages=173–8 |year=1999 |pmid=10503899 |doi=10.1016/S0304-3835(99)00120-2}}</ref> The EFSA considers TBHQ to be noncarcinogenic.<ref name=EFSA/> A 1986 review of scientific literature concerning the toxicity of TBHQ determined that a wide margin of safety exists between the levels of intake by humans and the doses that produce adverse effects in animal studies.<ref>{{Cite journal | last1 = Vanesch | first1 = G | title = Toxicology of tert-butylhydroquinone (TBHQ) | journal = ] | volume = 24 | issue = 10–11 | year = 1986 | pmid = 3542758 | doi = 10.1016/0278-6915(86)90289-9 | pages = 1063–5 }}</ref> |
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In addition, TBHQ has been identified by ] as having potential immunotoxic effects.<ref>{{Cite journal|last1=Naidenko|first1=Olga V.|last2=Andrews|first2=David Q.|last3=Temkin|first3=Alexis M.|last4=Stoiber|first4=Tasha|last5=Uche|first5=Uloma Igara|last6=Evans|first6=Sydney|last7=Perrone-Gray|first7=Sean|date=2021-03-24|title=Investigating Molecular Mechanisms of Immunotoxicity and the Utility of ToxCast for Immunotoxicity Screening of Chemicals Added to Food|journal=International Journal of Environmental Research and Public Health|language=en|volume=18|issue=7|pages=3332|doi=10.3390/ijerph18073332|pmid=33804855|pmc=8036665|issn=1660-4601|doi-access=free}}</ref> |
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There have been reports of vision disturbances in individuals exposed to this chemical.<ref>{{multiref|1={{Cite web|url=https://toxnet.nlm.nih.gov/cgi-bin/sis/search/a?dbs+hsdb:@term+@DOCNO+838|title=T-BUTYLHYDROQUINONE - National Library of Medicine HSDB Database|website=toxnet.nlm.nih.gov|access-date=2019-11-21}}|2=O'Donoghue, J.L. (ed.). Neurotoxicity of Industrial and Commercial Chemicals. Volume I. Boca Raton, FL: CRC Press, Inc., 1985., p. 129 – HSDB cites this source.}}</ref> |
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==References== |
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{{reflist|30em}} |
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{{DEFAULTSORT:Butylhydroquinone, Tert-}} |
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