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Butylated hydroxytoluene

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particles. The action of BHT in these is akin to the action of many other organic compounds, e.g., quaternary ammonium compounds, phenolics, and detergents, which disrupt viruses by insertion of the chemical into the virus membrane, coat, or other structure, which are established methods of viral disinfection secondary to methods of chemical oxidation and UV irradiation. In addition, there is a report of BHT use, topically against genital herpes lesions, a report of inhibitory activity
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against pseudorabies (in cell culture), and two studies, in veterinary contexts, of use of BHT to attempt to protect against virus exposure (pseudorabies in mouse and swine, and Newcastle in chickens). The relevance of other reports, regarding influenza in mice, is not easily discerned. Notably, this
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Types of Ingredients: Preservatives What They Do: Prevent food spoilage from ; maintain freshness Examples of Uses: Fruit sauces and jellies, beverages, baked goods, cured meats, oils and margarines, cereals, dressings, snack foods, fruits and vegetables Names Found on Product Labels: Ascorbic acid,
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The term disparate here is purely descriptive, and not pejorative—each of the primary research reports that follow is distinct and dissimilar, and so they are as a set, disparate. Moreover, no group of articles constitute a series, reflecting long-term study of BHT in a host-virus pair by the same
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Based on various, disparate primary research reports, BHT has been suggested to have anti-viral activity, and the reports divide into various study types. First, there are studies that describe virus inactivation—where treatment with the chemical results in disrupted or otherwise inactivated virus
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Hence, at present, the results do not present a scientific consensus in favour of the conclusion of the general antiviral potential of BHT when dosed in humans. Moreover, as of March 2020, no guidance from any of the internationally recognized associations of infectious disease specialists had
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Gharbi, Ines; Issaoui, Manel; El Gharbi, Sinda; Gazzeh, Nour-Eddine; Tekeya, Meriem; Mechri, Beligh; Flamini, Guido; Hammami, Mohamed (2017). "Butylated hydroxytoluene (BHT) emitted by fungi naturally occurring in olives during their pre-processing storage for improving olive oil stability".
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Hazardous Substances Data Bank under several categories in catalogues and databases, such as food additive, household product ingredient, industrial additive, personal care product/cosmetic ingredient, pesticide ingredient, plastic/rubber ingredient and medical/veterinary/research.
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series of primary research reports does not support a general conclusion of independent confirmation of the original research results, nor are there critical reviews appearing thereafter, in secondary sources, for the various host-virus systems studied with BHT.
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discussed a possible link between BHT and cancer risk in 1986, and some primary research studies in the 1970s–1990s reported both potential for increased risk and potential for decreased risk in the area of oncology. Because of this uncertainty, the
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As of March 2020, there are no examples in this series presenting primary research that reproduces earlier reported results—the reports generally present research results on distinct host-virus systems, rather than follow-up studies on the same
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Search of Pubmed in March 2020 with the main field search string, "(BHT OR butylated hydroxytoluene) AND antiviral ", see next citation, to pull articles focused on antiviral effects of the agent produced a single review source,
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Jiang G, Lin S, Wen L, Jiang Y, Zhao M, Chen F, Prasad KN, Duan X, Yang B (15 January 2013). "Identification of a novel phenolic compound in litchi (Litchi chinensis Sonn.) pericarp and bioactivity evaluation".
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BHT is used as a preservative ingredient in some foods. With this usage BHT maintains freshness or prevents spoilage; it may be used to decrease the rate at which the texture, color, or flavor of food changes.
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Yehye WA, Rahman NA, Ariffin A, Abd Hamid SB, Alhadi AA, Kadir FA, Yaeghoobi M (28 August 2015). "Understanding the Chemistry Behind the Antioxidant Activities of Butylated Hydroxytoluene (BHT): A Review".
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Williams, GM; Iatropoulos, M. J (1996). "Inhibition of the hepatocarcinogenicity of aflatoxin B1 in rats by low levels of the phenolic antioxidants butylated hydroxyanisole and butylated hydroxytoluene".
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to facilitate their safe storage. Some additive products contain BHT as their primary ingredient, while others contain the chemical merely as a component of their formulation, sometimes alongside
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Grohmann, Caio Vinícius Signorelli; Sinhoreti, Mário Alexandre Coelho; Soares, Eveline Freitas; Oliveira, Robson Ferraz de; Souza, Eduardo José de Carvalho; Geraldeli, Saulo (24 June 2022).
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Chetverikova, L. K; Ki'Ldivatov, I. Iu; Inozemtseva, L. I; Kramskaia, T. A; Filippov, V. K; Frolov, B. A (1989). "Factors of Antiviral Resistance in the Pathogenesis of Influenza in Mice".
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Helmut Fiege, Heinz-Werner Voges, Toshikazu Hamamoto, Sumio Umemura, Tadao Iwata, Hisaya Miki, Yasuhiro Fujita, Hans-Josef Buysch, Dorothea Garbe, Wilfried Paulus "Phenol Derivatives" in
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Pirtle, E. C; Sacks, J. M; Nachman, R. J (1986). "Antiviral effectiveness of butylated hydroxytoluene against pseudorabies (Aujeszky's disease) virus in cell culture, mice, and swine".
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Burton G. W., Ingold K. U. (1981). "Autoxidation of biological molecules. 1. Antioxidant activity of vitamin E and related chain-breaking phenolic antioxidants in vitro".
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citric acid, sodium benzoate, calcium propionate, sodium erythorbate, sodium nitrite, calcium sorbate, potassium sorbate, BHA, BHT, EDTA, tocopherols (Vitamin E)
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Kim, K. S; Moon, H. M; Sapienza, V; Carp, R. I; Pullarkat, R (1978). "Inactivation of cytomegalovirus and Semliki Forest virus by butylated hydroxytoluene".
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Yehye, Wageeh A.; Rahman, Noorsaadah Abdul; Ariffin, Azhar; Abd Hamid, Sharifah Bee; Alhadi, Abeer A.; Kadir, Farkaad A.; Yaeghoobi, Marzieh (2015-08-28).
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The European Union restricts the use of BHT in mouthwash to 0.001% concentration, in toothpaste to 0.01% concentration, and to 0.8% in other cosmetics.
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Richards, J. T; Katz, M. E; Kern, E. R (1985). "Topical butylated hydroxytoluene treatment of genital herpes simplex virus infections of guinea pigs".
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Chetverikova LK, Inozemtseva LI (1996). "Role of Lipid Peroxidation in the Pathogenesis of Influenza and Search for Antiviral Protective Agents".
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that BHT was noncarcinogenic in an animal model, societal concerns over its broad use have been expressed. BHT has also been postulated as an
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drug, but as of December 2022, use of BHT as a drug is not supported by the scientific literature and it has not been approved by any
746: 2091: 2066:"Scientific Opinion on the re-evaluation of butylated hydroxytoluene BHT (E 321) as a food additive | European Food Safety Authority" 1519: 1200: 1329:§ 137.350(a)(4) allows BHT up to 0.0033% by weight in "enriched rice", while 9 CFR § 381.147](f)(1) allows up to 0.01% in 904: 3028: 2988:"Traitements locaux, antiviraux ou non, dans la prise en charge de l'herpès oro-facial et gĂ©nital (grossesse et nouveau-nĂ© exclus)" 1553: 1170: 2399:(1985). "Modification of aflatoxin B1 binding to DNA in vivo in rats fed phenolic antioxidants, ethoxyquin and a dithiothione". 1344:
Some food companies have voluntarily eliminated BHT from their products or have announced that they were going to phase it out.
1207: 3701: 3439: 2044: 2114: 2513: 3168: 2235: 1214: 2377:(Report). Vol. 40. World Health Organization: International Agency For Research On Cancer. 1986. pp. 161–206. 3696: 3706: 2650: 2549:
Snipes W, Person S, Keith A, Cupp J (4 April 1975). "Butylated Hydroxytoluene Inactivated Lipid-Containing Viruses".
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reaction by converting peroxy radicals to hydroperoxides. It effects this function by donating a hydrogen atom:
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Brugh, M (1977). "Butylated hydroxytoluene protects chickens exposed to Newcastle disease virus".
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BHT is primarily used as an antioxidant food additive. In the United States, it is classified as
1135: 2748:"Persistence of Coronaviruses on Inanimate Surfaces and Their Inactivation With Biocidal Agents" 3229: 2371: 1018: 1739:"Production of Natural Butylated Hydroxytoluene as an Antioxidant by Freshwater Phytoplankton" 1738: 230: 3737: 3732: 3425: 2318:"New restrictions for Butylated Hydroxytoluene (BHT) and Acid Yellow 3 apply as of July 2023" 676: 646: 578: 2092:"Food Additives & Ingredients > Overview of Food Ingredients, Additives & Colors" 30: 2881: 2558: 2003:, National Cancer Institute, CARCINOGENESIS Technical Report Series No. 150, 1979, 128 pp 1753: 1002: 363: 52: 1177: 8: 3154: 2335: 1631: 1384: 1353: 1042: 146: 136: 2885: 2562: 1757: 1458:
Please help update this article to reflect recent events or newly available information.
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in fluids (e.g. fuels, oils) and other materials, and the regulations overseen by the
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Mandell, Douglas, and Bennett's Principles and Practice of Infectious Diseases
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study from 1979 in rats and mice. It is approved for use in the U.S. by the
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European Society of Clinical Microbiology and Infectious Diseases (ESCMID)
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research team (the pair by Chetverikova et al. being the nearest to this).
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InChI=1S/C15H24O/c1-10-8-11(14(2,3)4)13(16)12(9-10)15(5,6)7/h8-9,16H,1-7H3
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Franklin, R. A (1976). "Butylated hydroxytoluene in sarcoma-prone dogs".
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InChI=1/C15H24O/c1-10-8-11(14(2,3)4)13(16)12(9-10)15(5,6)7/h8-9,16H,1-7H3
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Bioassay of Butylated Hydroxytoluene (BHT) for Possible Carcinogenicity
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advocated use of BHT products as an antiviral therapy or prophylactic.
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US Dept of Health & Human Services. Household Products Database.
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and other solvents and laboratory chemicals. It is added to certain
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Except where otherwise noted, data are given for materials in their
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Fujisawa, Seiichiro; Kadoma, Yoshinori; Yokoe, Ichiro (July 2004).
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Cook, Nigel; Knight, Angus; Richards, Gary P. (1 July 2016).
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puts BHT in its "caution" column and recommends avoiding it.
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See for instance, this and the following two references:
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Kampf G, Todt D, Pfaender S, Steinmann E (March 2020).
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BHT is also used as an antioxidant in products such as
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by hydroxymethylation or aminomethylation followed by
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National Institute for Occupational Safety and Health
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Rutala, William A.; Weber, David J. (January 2015).
2591: 2433: 1909: 2986: 2844: 2840: 2838: 2679: 3077:"ESCMID—Search—Website Search—Search in Category" 3016:DOI, DERM-04-2002-129-4-C2-0151-9638-101019-ART18 3719: 2806: 1834:European Journal of Lipid Science and Technology 1794: 1063:of BHT in industry has involved the reaction of 326: 3111:. Infectious Diseases Society of America (IDSA) 2835: 2395:Kensler, TW; Egner, PA; Trush, MA; Bueding, E; 727: 700: 145: 3102: 3045: 2112: 1863:Ullmann's Encyclopedia of Industrial Chemistry 3433: 3162: 2364: 2336:"SCOGS (Select Committee on GRAS Substances)" 1506:determined that BHT was noncarcinogenic in a 3142:CDC – NIOSH Pocket Guide to Chemical Hazards 2017:"CFR - Code of Federal Regulations Title 21" 1985:"CFR - Code of Federal Regulations Title 21" 1961:. US National Library of Medicine. Haz-Map. 1690:Institute for Occupational Safety and Health 1650:"Safety data for 2,6-di-tert-butyl-p-cresol" 1186:introducing citations to additional sources 3137:Chemistry of BHA and BHT Food Preservatives 2720: 2626: 1873:Article Online Posting Date: June 15, 2000. 3440: 3426: 3169: 3155: 2993:Annales de Dermatologie et de VĂ©nĂ©rĂ©ologie 2985:Chosidow O, Lebrun-Vignes B (April 2002). 2354:"CFR—Code of Federal Regulations Title 21" 1857: 1855: 1134:Alternatively, BHT has been prepared from 954:properties. BHT is widely used to prevent 395: 251: 229: 2776: 2766: 2697: 2640: 2542: 2278: 1520:Center for Science in the Public Interest 362: 2917:Vestnik Akademii Meditsinskikh Nauk SSSR 2469: 2305:. Scientific American. 19 December 2013. 2207: 1885:Journal of the American Chemical Society 1677: 1675: 1626: 1624: 1622: 1607:NIOSH Pocket Guide to Chemical Hazards. 1479:, BHT has low acute toxicity (e.g., the 1176:Relevant discussion may be found on the 1054: 2847:American Journal of Veterinary Research 2315: 2295: 2217:, Synapse Information Resources, 2004. 2148:European Journal of Medicinal Chemistry 1852: 1730: 1028:sp.) are capable of producing BHT as a 391: 3720: 2384:from the original on 5 September 2015. 1996: 1994: 1736: 1632:"ICSC 0841 - BUTYLATED HYDROXYTOLUENE" 1602: 1600: 1598: 1596: 1575: 770:127 Â°C (261 Â°F; 400 K) 553:265 Â°C (509 Â°F; 538 K) 242: 3421: 3150: 2871: 2723:"Why Soap Works - The New York Times" 2137: 2135: 1672: 1619: 989: 543:70 Â°C (158 Â°F; 343 K) 423:Key: NLZUEZXRPGMBCV-UHFFFAOYSA-N 209: 189: 1438: 1153: 121:3,5-(Dimethylethyl)-4-hydroxytoluene 2506: 2188: 2115:"The Food Babe: Enemy of Chemicals" 2113:Hamblin, James (11 February 2015). 2106: 1991: 1593: 1249:The species behaves as a synthetic 433:Key: NLZUEZXRPGMBCV-UHFFFAOYAU 317: 301: 13: 2642:10.1016/B978-1-4557-4801-3.00301-5 2594:The Journal of Infectious Diseases 2132: 1583:"2,6-di-tert-butyl-4-methylphenol" 1570:Vattenlöslighet: 1,1 mg/L (20 °C) 1280:• + ArO• → nonradical products 723: 14: 3769: 3130: 1928:10.1016/j.chemphyslip.2004.03.005 1434: 118:4-Methyl-2,6-di-tert-butyl phenol 3447: 3103:IDSA Web Tools (12 March 2020). 3046:ISID Web Tools (12 March 2020). 2303:"BHA and BHT: A Case for Fresh?" 1766:10.1111/j.1529-8817.2008.00596.x 1443: 1308: 1169:relies largely or entirely on a 1158: 1074:(2-methylpropene), catalyzed by 1046:) living in olives produce BHT. 894: 652: 481: 84:2,6-DI-tert-butyl-4-methylphenol 38: 29: 3293:2,4-Dimethyl-6-tert-butylphenol 3176: 3095: 3069: 3039: 3021: 2968: 2958: 2931: 2908: 2865: 2800: 2739: 2714: 2673: 2620: 2585: 2532: 2463: 2427: 2388: 2346: 2328: 2316:Slavova, Siana (23 June 2023). 2309: 2246: 2228: 2182: 2084: 2058: 2027: 2009: 1977: 1942: 1916:Chemistry and Physics of Lipids 1903: 1876: 1824: 1737:Babu B, Wu JT (December 2008). 1496:US Food and Drug Administration 1403:. BHT is also used to prevent 1295: 890:(at 25 Â°C , 100 kPa). 2372:Butylated hydroxytoluene (BHT) 1810:10.1016/j.foodchem.2012.08.089 1788: 1694: 1642: 1545: 1347: 1013:Cylindrospermopsis raciborskii 616:Occupational safety and health 487: 475: 454:CC(C)(C)c1cc(C)cc(c1O)C(C)(C)C 1: 3064:There are 0 results for 'BHT' 2721:Ferris Jabr (13 March 2020). 2514:"Two Preservatives to Avoid?" 2484:10.1016/s0140-6736(76)91766-9 2005:National Institutes of Health 1865:, Wiley-VCH, Weinheim, 2002. 1538: 1049: 1040:. Several fungi (for example 1006:, as well as three different 946:, chemically a derivative of 810:(US health exposure limits): 3364:Automatic transmission fluid 3298:Dinonylnaphthylsulfonic acid 3250:Racing fuel (Tetraethyllead) 2821:10.1016/0166-3542(85)90042-7 2699:10.4315/0362-028X.JFP-15-570 2449:10.1016/0304-3835(96)04228-0 2160:10.1016/j.ejmech.2015.06.026 2040:Food and Drug Administration 1716:10.1016/j.ejmech.2015.06.026 1500:generally recognized as safe 1426: 1380:, where BHT is known as the 1323:Food and Drug Administration 1315:generally recognized as safe 1273:• + ArOH → ROOH + ArO• 1149: 970:"—allow small amounts to be 968:generally recognized as safe 966:—which considers BHT to be " 7: 778:or concentration (LD, LC): 10: 3774: 3288:Dimethyl methylphosphonate 2768:10.1016/j.jhin.2020.01.022 2686:Journal of Food Protection 2271:10.1590/0103-6440202204242 2191:"Butylated Hydroxytoluene" 1475:Like many closely related 1197:"Butylated hydroxytoluene" 115:Dibutylated hydroxytoluene 15: 3684: 3635: 3455: 3387: 3346: 3258: 3187: 2919:(in Russian) (11): 63–8. 2215:Handbook of Preservatives 1686:GESTIS Substance Database 1515:World Health Organization 1504:National Cancer Institute 1494:of >9 g/kg). The 1452:This section needs to be 1319:National Cancer Institute 1036:also produces BHT in its 986:for use as an antiviral. 976:National Cancer Institute 950:, that is useful for its 884: 867: 804: 774: 633: 613: 608: 462: 442: 407: 129: 67: 51: 46: 37: 28: 24:Butylated hydroxytoluene 3648:Butylated hydroxytoluene 3643:Butylated hydroxyanisole 3273:Butylated hydroxytoluene 2940:Vestn Ross Akad Med Nauk 2259:Brazilian Dental Journal 2213:Michael Ash, Irene Ash, 2195:pubchem.ncbi.nlm.nih.gov 1871:10.1002/14356007.a19_313 1421:butylated hydroxyanisole 1417:polymerisation inhibitor 929:Butylated hydroxytoluene 879:Butylated hydroxyanisole 691:Precautionary statements 3379:Windshield washer fluid 3323:Methyl tert-butyl ether 3303:2,6-Di-tert-butylphenol 3215:Lead Replacement Petrol 2606:10.1093/infdis/138.1.91 1552:KEMI Anställd (1994). 1485:2,6-di-tert-butylphenol 510:White to yellow powder 91:-butyl-4-hydroxytoluene 3230:Compressed natural gas 3048:"You searched for BHT" 2894:10.1126/science.897670 2571:10.1126/science.163494 2413:10.1093/carcin/6.5.759 2021:www.accessdata.fda.gov 1958:.US EPA. InertFinder. 1846:10.1002/ejlt.201600343 1070:(4-methylphenol) with 1019:Microcystis aeruginosa 984:drug regulatory agency 734: 1407:formation in organic 1300:BHT is listed by the 1055:Industrial production 937:dibutylhydroxytoluene 733: 61:-butyl-4-methylphenol 3753:Tert-butyl compounds 3033:www.ncbi.nlm.nih.gov 2098:. 20 February 2020. 1746:Journal of Phycology 1182:improve this article 1003:Botryococcus braunii 800:mg/kg (dermal, rat) 716:(fire diamond) 53:Preferred IUPAC name 2886:1977Sci...197.1291B 2563:1975Sci...188...64S 1897:10.1021/ja00411a035 1758:2008JPcgy..44.1447B 1477:phenol antioxidants 1354:metalworking fluids 1043:Aspergillus conicus 560:Solubility in water 502: g/mol 287:(antioxidants, ...) 25: 3758:E-number additives 3662:1,2-Diaminopropane 3463:6-Hydroxymelatonin 3283:1,2-Dichloroethane 2809:Antiviral Research 2727:The New York Times 2070:www.efsa.europa.eu 1967:2015-09-05 at the 1954:2015-09-05 at the 1654:ptcl.chem.ox.ac.uk 1513:Nevertheless, the 1498:classifies BHT as 1378:petroleum industry 1325:: For example, 21 1317:(GRAS) based on a 1061:chemical synthesis 990:Natural occurrence 917:Infobox references 868:Related compounds 849:(Immediate danger) 735: 23: 3748:Food antioxidants 3743:Fuel antioxidants 3715: 3714: 3636:Fuel antioxidants 3527: 3478:Alpha-lipoic acid 3471: 3456:Food antioxidants 3415: 3414: 3338:Tetranitromethane 3318:Metal deactivator 3278:1,2-Dibromoethane 3092:Search for "bht". 2999:(4–C2): 635–645. 2518:Berkeley Wellness 1891:(21): 6472–6477. 1704:Eur. J. Med. Chem 1560:on 11 August 2011 1473: 1472: 1247: 1246: 1232: 935:), also known as 925:Chemical compound 923: 922: 874:Related compounds 859:Safety data sheet 677:Hazard statements 376:CompTox Dashboard 171:Interactive image 3765: 3560:-Acetylserotonin 3525: 3469: 3442: 3435: 3428: 3419: 3418: 3402:MTBE controversy 3171: 3164: 3157: 3148: 3147: 3124: 3123: 3121:No results found 3118: 3116: 3105:"Search Results" 3099: 3093: 3091: 3089: 3087: 3073: 3067: 3066: 3061: 3059: 3043: 3037: 3036: 3025: 3019: 3018: 3013: 3011: 2990: 2972: 2966: 2962: 2956: 2955: 2935: 2929: 2928: 2912: 2906: 2905: 2880:(4310): 1291–2. 2869: 2863: 2862: 2842: 2833: 2832: 2804: 2798: 2797: 2795: 2793: 2780: 2770: 2752: 2743: 2737: 2736: 2734: 2733: 2718: 2712: 2711: 2701: 2677: 2671: 2670: 2668: 2667: 2644: 2635:: 3294–3309.e4. 2624: 2618: 2617: 2589: 2583: 2582: 2546: 2540: 2536: 2530: 2529: 2527: 2525: 2510: 2504: 2503: 2467: 2461: 2460: 2431: 2425: 2424: 2392: 2386: 2385: 2383: 2376: 2368: 2362: 2361: 2350: 2344: 2343: 2332: 2326: 2325: 2313: 2307: 2306: 2299: 2293: 2292: 2282: 2250: 2244: 2243: 2232: 2226: 2211: 2205: 2204: 2202: 2201: 2186: 2180: 2179: 2139: 2130: 2129: 2127: 2125: 2110: 2104: 2103: 2088: 2082: 2081: 2079: 2077: 2062: 2056: 2055: 2053: 2052: 2043:. Archived from 2031: 2025: 2024: 2013: 2007: 1998: 1989: 1988: 1981: 1975: 1946: 1940: 1939: 1907: 1901: 1900: 1880: 1874: 1859: 1850: 1849: 1828: 1822: 1821: 1792: 1786: 1785: 1752:(6): 1447–1454. 1743: 1734: 1728: 1727: 1698: 1692: 1679: 1670: 1669: 1667: 1665: 1656:. Archived from 1646: 1640: 1639: 1628: 1617: 1616: 1604: 1591: 1590: 1579: 1573: 1572: 1567: 1565: 1549: 1468: 1465: 1459: 1447: 1446: 1439: 1389:hydraulic fluids 1387:, it is used in 1370:transformer oils 1242: 1239: 1233: 1231: 1190: 1162: 1154: 997:, including the 944:organic compound 907: 901: 898: 897: 839: 799: 755: 748: 741: 726: 706: 702: 698: 684: 656: 603: 599: 572: 568: 501: 489: 483: 477: 470:Chemical formula 400: 399: 384: 382: 366: 330: 319: 305: 281: 263: 255: 244: 233: 213: 193: 173: 149: 42: 33: 26: 22: 3773: 3772: 3768: 3767: 3766: 3764: 3763: 3762: 3728:Natural phenols 3718: 3717: 3716: 3711: 3680: 3676:Ethylenediamine 3667:2,4-Dimethyl-6- 3631: 3551:-Acetylcysteine 3451: 3446: 3416: 3411: 3407:Pay at the pump 3383: 3342: 3313:Ethylenediamine 3254: 3195:Gasoline/petrol 3183: 3175: 3133: 3128: 3127: 3114: 3112: 3100: 3096: 3085: 3083: 3075: 3074: 3070: 3057: 3055: 3044: 3040: 3027: 3026: 3022: 3009: 3007: 2973: 2969: 2963: 2959: 2936: 2932: 2913: 2909: 2870: 2866: 2843: 2836: 2805: 2801: 2791: 2789: 2755:J. Hosp. Infect 2750: 2744: 2740: 2731: 2729: 2719: 2715: 2678: 2674: 2665: 2663: 2653: 2625: 2621: 2590: 2586: 2557:(4183): 64–66. 2547: 2543: 2537: 2533: 2523: 2521: 2512: 2511: 2507: 2468: 2464: 2432: 2428: 2393: 2389: 2381: 2374: 2370: 2369: 2365: 2352: 2351: 2347: 2334: 2333: 2329: 2314: 2310: 2301: 2300: 2296: 2251: 2247: 2240:Millipore Sigma 2234: 2233: 2229: 2212: 2208: 2199: 2197: 2187: 2183: 2140: 2133: 2123: 2121: 2111: 2107: 2090: 2089: 2085: 2075: 2073: 2064: 2063: 2059: 2050: 2048: 2033: 2032: 2028: 2015: 2014: 2010: 1999: 1992: 1983: 1982: 1978: 1969:Wayback Machine 1956:Wayback Machine 1947: 1943: 1908: 1904: 1881: 1877: 1860: 1853: 1840:(11): 1600343. 1829: 1825: 1793: 1789: 1741: 1735: 1731: 1699: 1695: 1680: 1673: 1663: 1661: 1660:on 21 June 2002 1648: 1647: 1643: 1630: 1629: 1620: 1605: 1594: 1587:www.chemsrc.com 1581: 1580: 1576: 1563: 1561: 1550: 1546: 1541: 1492: 1483:analog of BHT, 1469: 1463: 1460: 1457: 1448: 1444: 1437: 1429: 1362:pharmaceuticals 1350: 1311: 1298: 1279: 1272: 1243: 1237: 1234: 1191: 1189: 1175: 1163: 1152: 1129: 1125: 1121: 1117: 1113: 1109: 1105: 1101: 1097: 1093: 1089: 1085: 1057: 1052: 1030:natural product 992: 926: 919: 914: 913: 912:  ?) 903: 899: 895: 891: 875: 850: 837: 833: 820: 797: 793: 787: 760: 759: 758: 757: 750: 743: 736: 732: 724: 693: 679: 665: 649: 626: 601: 597: 570: 566: 562: 499: 486: 480: 472: 458: 455: 450: 449: 438: 435: 434: 431: 425: 424: 421: 415: 414: 403: 385: 378: 369: 349: 333: 320: 308: 273: 236: 216: 196: 176: 163: 152: 139: 125: 124: 112:Additin RC 7110 109:Antioxidant 264 63: 62: 21: 12: 11: 5: 3771: 3761: 3760: 3755: 3750: 3745: 3740: 3735: 3730: 3713: 3712: 3710: 3709: 3704: 3699: 3694: 3688: 3686: 3682: 3681: 3679: 3678: 3673: 3664: 3659: 3650: 3645: 3639: 3637: 3633: 3632: 3630: 3629: 3624: 3618: 3613: 3603: 3593: 3588: 3583: 3578: 3573: 3568: 3563: 3554: 3545: 3540: 3535: 3530: 3522: 3520:Hydroxytyrosol 3517: 3512: 3507: 3502: 3497: 3487: 3481: 3475: 3465: 3459: 3457: 3453: 3452: 3445: 3444: 3437: 3430: 3422: 3413: 3412: 3410: 3409: 3404: 3399: 3393: 3391: 3385: 3384: 3382: 3381: 3376: 3371: 3366: 3361: 3356: 3350: 3348: 3344: 3343: 3341: 3340: 3335: 3333:Tetraethyllead 3330: 3325: 3320: 3315: 3310: 3305: 3300: 3295: 3290: 3285: 3280: 3275: 3270: 3264: 3262: 3260:Fuel additives 3256: 3255: 3253: 3252: 3247: 3242: 3237: 3232: 3227: 3222: 3217: 3212: 3207: 3202: 3197: 3191: 3189: 3185: 3184: 3174: 3173: 3166: 3159: 3151: 3145: 3144: 3139: 3132: 3131:External links 3129: 3126: 3125: 3094: 3068: 3038: 3020: 2967: 2957: 2942:(in Russian). 2930: 2907: 2864: 2834: 2799: 2761:(3): 246–251. 2738: 2713: 2692:(7): 1273–94. 2672: 2651: 2619: 2584: 2541: 2531: 2505: 2478:(7972): 1296. 2462: 2437:Cancer Letters 2426: 2407:(5): 759–763. 2401:Carcinogenesis 2387: 2363: 2345: 2327: 2308: 2294: 2245: 2227: 2206: 2181: 2131: 2105: 2083: 2072:. 7 March 2012 2057: 2026: 2008: 1990: 1976: 1941: 1922:(2): 189–195. 1902: 1875: 1851: 1823: 1798:Food Chemistry 1787: 1729: 1693: 1671: 1641: 1636:www.inchem.org 1618: 1592: 1574: 1543: 1542: 1540: 1537: 1490: 1471: 1470: 1451: 1449: 1442: 1436: 1435:Health effects 1433: 1428: 1425: 1376:fluid. In the 1349: 1346: 1310: 1307: 1297: 1294: 1282: 1281: 1277: 1274: 1270: 1245: 1244: 1180:. Please help 1166: 1164: 1157: 1151: 1148: 1144:hydrogenolysis 1132: 1131: 1127: 1123: 1119: 1115: 1111: 1107: 1103: 1099: 1095: 1091: 1087: 1083: 1056: 1053: 1051: 1048: 991: 988: 972:added to foods 924: 921: 920: 915: 893: 892: 888:standard state 885: 882: 881: 876: 873: 870: 869: 865: 864: 862: 855: 854: 851: 845: 842: 841: 834: 828: 825: 824: 821: 815: 812: 811: 802: 801: 794: 785: 783: 780: 779: 772: 771: 768: 762: 761: 751: 744: 737: 722: 721: 720: 719: 717: 708: 707: 694: 689: 686: 685: 680: 675: 672: 671: 666: 661: 658: 657: 650: 645: 642: 641: 631: 630: 627: 624: 621: 620: 611: 610: 606: 605: 594: 592:Vapor pressure 588: 587: 584: 575: 574: 563: 558: 555: 554: 551: 545: 544: 541: 535: 534: 531: 525: 524: 518: 512: 511: 508: 504: 503: 497: 491: 490: 484: 478: 473: 468: 465: 464: 460: 459: 457: 456: 453: 445: 444: 443: 440: 439: 437: 436: 432: 429: 428: 426: 422: 419: 418: 410: 409: 408: 405: 404: 402: 401: 388: 386: 374: 371: 370: 368: 367: 359: 357: 351: 350: 348: 347: 343: 341: 335: 334: 332: 331: 323: 321: 313: 310: 309: 307: 306: 298: 296: 290: 289: 283: 275: 274: 272: 271: 267: 265: 257: 256: 246: 238: 237: 235: 234: 226: 224: 218: 217: 215: 214: 206: 204: 198: 197: 195: 194: 186: 184: 178: 177: 175: 174: 166: 164: 157: 154: 153: 151: 150: 142: 140: 135: 132: 131: 127: 126: 123: 122: 119: 116: 113: 110: 107: 104: 101: 98: 95: 92: 85: 82: 70: 69: 65: 64: 56: 55: 49: 48: 44: 43: 35: 34: 18:FS Class E.321 9: 6: 4: 3: 2: 3770: 3759: 3756: 3754: 3751: 3749: 3746: 3744: 3741: 3739: 3736: 3734: 3731: 3729: 3726: 3725: 3723: 3708: 3705: 3703: 3700: 3698: 3695: 3693: 3690: 3689: 3687: 3683: 3677: 3674: 3672: 3670: 3665: 3663: 3660: 3658: 3656: 3651: 3649: 3646: 3644: 3641: 3640: 3638: 3634: 3628: 3625: 3622: 3619: 3617: 3614: 3611: 3607: 3604: 3601: 3597: 3594: 3592: 3589: 3587: 3584: 3582: 3579: 3577: 3574: 3572: 3569: 3567: 3564: 3561: 3559: 3555: 3552: 3550: 3546: 3544: 3541: 3539: 3536: 3534: 3531: 3529: 3523: 3521: 3518: 3516: 3513: 3511: 3508: 3506: 3503: 3501: 3498: 3495: 3491: 3488: 3485: 3484:Ascorbic acid 3482: 3479: 3476: 3473: 3466: 3464: 3461: 3460: 3458: 3454: 3450: 3443: 3438: 3436: 3431: 3429: 3424: 3423: 3420: 3408: 3405: 3403: 3400: 3398: 3395: 3394: 3392: 3390: 3386: 3380: 3377: 3375: 3372: 3370: 3367: 3365: 3362: 3360: 3357: 3355: 3352: 3351: 3349: 3345: 3339: 3336: 3334: 3331: 3329: 3326: 3324: 3321: 3319: 3316: 3314: 3311: 3309: 3306: 3304: 3301: 3299: 3296: 3294: 3291: 3289: 3286: 3284: 3281: 3279: 3276: 3274: 3271: 3269: 3266: 3265: 3263: 3261: 3257: 3251: 3248: 3246: 3243: 3241: 3238: 3236: 3233: 3231: 3228: 3226: 3223: 3221: 3218: 3216: 3213: 3211: 3208: 3206: 3203: 3201: 3198: 3196: 3193: 3192: 3190: 3186: 3182: 3179: 3172: 3167: 3165: 3160: 3158: 3153: 3152: 3149: 3143: 3140: 3138: 3135: 3134: 3122: 3110: 3109:IDSociety.org 3106: 3098: 3082: 3078: 3072: 3065: 3053: 3049: 3042: 3034: 3030: 3024: 3017: 3006: 3002: 2998: 2994: 2989: 2982: 2978: 2971: 2961: 2953: 2949: 2945: 2941: 2934: 2926: 2922: 2918: 2911: 2903: 2899: 2895: 2891: 2887: 2883: 2879: 2875: 2868: 2860: 2856: 2853:(9): 1892–5. 2852: 2848: 2841: 2839: 2830: 2826: 2822: 2818: 2815:(5): 281–90. 2814: 2810: 2803: 2788: 2784: 2779: 2774: 2769: 2764: 2760: 2756: 2749: 2742: 2728: 2724: 2717: 2709: 2705: 2700: 2695: 2691: 2687: 2683: 2676: 2662: 2658: 2654: 2652:9781455748013 2648: 2643: 2638: 2634: 2630: 2623: 2615: 2611: 2607: 2603: 2599: 2595: 2588: 2580: 2576: 2572: 2568: 2564: 2560: 2556: 2552: 2545: 2535: 2519: 2515: 2509: 2501: 2497: 2493: 2489: 2485: 2481: 2477: 2473: 2466: 2458: 2454: 2450: 2446: 2442: 2438: 2430: 2422: 2418: 2414: 2410: 2406: 2402: 2398: 2391: 2380: 2373: 2367: 2359: 2355: 2349: 2341: 2337: 2331: 2323: 2319: 2312: 2304: 2298: 2290: 2286: 2281: 2276: 2272: 2268: 2264: 2260: 2256: 2249: 2241: 2237: 2231: 2224: 2223:1-890595-66-7 2220: 2216: 2210: 2196: 2192: 2185: 2177: 2173: 2169: 2165: 2161: 2157: 2153: 2149: 2145: 2138: 2136: 2120: 2116: 2109: 2102: 2097: 2093: 2087: 2071: 2067: 2061: 2047:on 2009-07-09 2046: 2042: 2041: 2036: 2030: 2022: 2018: 2012: 2006: 2002: 1997: 1995: 1986: 1980: 1973: 1970: 1966: 1963: 1960: 1957: 1953: 1950: 1945: 1937: 1933: 1929: 1925: 1921: 1917: 1913: 1906: 1898: 1894: 1890: 1886: 1879: 1872: 1868: 1864: 1858: 1856: 1847: 1843: 1839: 1835: 1827: 1819: 1815: 1811: 1807: 1803: 1799: 1791: 1783: 1779: 1775: 1771: 1767: 1763: 1759: 1755: 1751: 1747: 1740: 1733: 1725: 1721: 1717: 1713: 1709: 1705: 1697: 1691: 1687: 1683: 1678: 1676: 1659: 1655: 1651: 1645: 1638:. March 1999. 1637: 1633: 1627: 1625: 1623: 1614: 1610: 1603: 1601: 1599: 1597: 1588: 1584: 1578: 1571: 1559: 1555: 1548: 1544: 1536: 1532: 1529: 1523: 1521: 1516: 1511: 1509: 1505: 1501: 1497: 1493: 1486: 1482: 1478: 1467: 1455: 1450: 1441: 1440: 1432: 1424: 1422: 1418: 1414: 1410: 1406: 1402: 1398: 1394: 1390: 1386: 1383: 1382:fuel additive 1379: 1375: 1371: 1367: 1363: 1359: 1355: 1345: 1342: 1338: 1336: 1332: 1328: 1324: 1320: 1316: 1309:Food additive 1306: 1303: 1293: 1291: 1287: 1275: 1268: 1267: 1266: 1264: 1263:autocatalytic 1260: 1256: 1252: 1241: 1230: 1227: 1223: 1220: 1216: 1213: 1209: 1206: 1202: 1199: â€“  1198: 1194: 1193:Find sources: 1187: 1183: 1179: 1173: 1172: 1171:single source 1167:This section 1165: 1161: 1156: 1155: 1147: 1145: 1141: 1139: 1081: 1080: 1079: 1077: 1076:sulfuric acid 1073: 1069: 1067: 1062: 1047: 1045: 1044: 1039: 1035: 1031: 1027: 1026: 1021: 1020: 1015: 1014: 1009: 1008:cyanobacteria 1005: 1004: 1000: 996: 995:Phytoplankton 987: 985: 981: 977: 973: 969: 965: 961: 957: 953: 949: 945: 942: 938: 934: 930: 918: 911: 906: 889: 883: 880: 877: 872: 871: 866: 863: 860: 857: 856: 852: 848: 844: 843: 835: 832:(Recommended) 831: 827: 826: 822: 819:(Permissible) 818: 814: 813: 809: 808: 803: 795: 791: 782: 781: 777: 773: 769: 767: 764: 763: 756: 749: 742: 718: 715: 714: 710: 709: 695: 692: 688: 687: 681: 678: 674: 673: 670: 667: 664: 660: 659: 655: 651: 648: 644: 643: 639: 637: 632: 628: 623: 622: 618: 617: 612: 607: 595: 593: 590: 589: 585: 583: 582: 577: 576: 564: 561: 557: 556: 552: 550: 549:Boiling point 547: 546: 542: 540: 539:Melting point 537: 536: 532: 530: 527: 526: 523: 519: 517: 514: 513: 509: 506: 505: 498: 496: 493: 492: 474: 471: 467: 466: 461: 452: 451: 448: 441: 427: 417: 416: 413: 406: 398: 394: 393:DTXSID2020216 390: 389: 387: 377: 373: 372: 365: 361: 360: 358: 356: 353: 352: 345: 344: 342: 340: 337: 336: 329: 325: 324: 322: 316: 312: 311: 304: 300: 299: 297: 295: 292: 291: 288: 284: 282: 277: 276: 269: 268: 266: 264: 259: 258: 254: 250: 247: 245: 243:ECHA InfoCard 240: 239: 232: 228: 227: 225: 223: 220: 219: 212: 208: 207: 205: 203: 200: 199: 192: 188: 187: 185: 183: 180: 179: 172: 168: 167: 165: 161: 156: 155: 148: 144: 143: 141: 138: 134: 133: 128: 120: 117: 114: 111: 108: 105: 102: 99: 96: 93: 90: 86: 83: 80: 76: 72: 71: 66: 60: 54: 50: 45: 41: 36: 32: 27: 19: 3738:Alkylphenols 3733:Antioxidants 3692:Folin method 3685:Measurements 3671:-butylphenol 3668: 3657:-butylphenol 3654: 3647: 3623:(coenzyme Q) 3606:Tocotrienols 3557: 3548: 3449:Antioxidants 3328:Nitromethane 3272: 3268:Butyl rubber 3245:Butanol fuel 3120: 3113:. Retrieved 3108: 3097: 3084:. Retrieved 3080: 3071: 3063: 3056:. Retrieved 3051: 3041: 3032: 3023: 3015: 3008:. Retrieved 2996: 2992: 2970: 2960: 2946:(3): 37–40. 2943: 2939: 2933: 2916: 2910: 2877: 2873: 2867: 2850: 2846: 2812: 2808: 2802: 2790:. Retrieved 2758: 2754: 2741: 2730:. Retrieved 2726: 2716: 2689: 2685: 2675: 2664:. Retrieved 2632: 2622: 2597: 2593: 2587: 2554: 2550: 2544: 2534: 2524:12 September 2522:. Retrieved 2517: 2508: 2475: 2471: 2465: 2443:(1): 49–53. 2440: 2436: 2429: 2404: 2400: 2397:Groopman, JD 2390: 2366: 2357: 2348: 2339: 2330: 2322:Obelis Group 2321: 2311: 2297: 2265:(3): 92–98. 2262: 2258: 2248: 2239: 2230: 2214: 2209: 2198:. Retrieved 2194: 2184: 2151: 2147: 2124:12 September 2122:. Retrieved 2119:The Atlantic 2118: 2108: 2099: 2095: 2086: 2074:. Retrieved 2069: 2060: 2049:. Retrieved 2045:the original 2038: 2029: 2020: 2011: 1979: 1944: 1919: 1915: 1905: 1888: 1884: 1878: 1862: 1837: 1833: 1826: 1804:(2): 563–8. 1801: 1797: 1790: 1749: 1745: 1732: 1707: 1703: 1696: 1662:. Retrieved 1658:the original 1653: 1644: 1635: 1586: 1577: 1569: 1562:. Retrieved 1558:the original 1547: 1533: 1527: 1524: 1512: 1474: 1461: 1453: 1430: 1351: 1343: 1339: 1312: 1299: 1296:Applications 1283: 1259:autoxidation 1248: 1235: 1225: 1218: 1211: 1204: 1192: 1168: 1140:-butylphenol 1137: 1133: 1094:)OH + 2 CH 1065: 1058: 1041: 1032:. The fruit 1025:Oscillatoria 1023: 1017: 1011: 1001: 993: 956:free radical 936: 932: 928: 927: 806: 775: 712: 668: 635: 625:Main hazards 614: 580: 339:RTECS number 130:Identifiers 88: 78: 74: 68:Other names 58: 3596:Tocopherols 3581:Resveratrol 3566:Oleocanthal 3515:Glutathione 3510:Polyphenols 3490:Carotenoids 3486:(vitamin C) 3369:Brake fluid 3220:Electricity 3210:Biogasoline 2600:(1): 91–4. 2154:: 295–312. 2096:www.fda.gov 1710:: 295–312. 1508:mouse model 1348:Antioxidant 1284:where R is 1072:isobutylene 999:green algae 964:U.S. F.D.A. 952:antioxidant 790:median dose 776:Lethal dose 766:Flash point 663:Signal word 619:(OHS/OSH): 533:1.048 g/cm 507:Appearance 463:Properties 249:100.004.439 191:CHEBI:34247 3722:Categories 3621:Ubiquinone 3586:Selegiline 3576:Rasagiline 3571:Oleuropein 3543:Mofegiline 3533:Ladostigil 3528:-carnitine 3472:-carnitine 3359:Antifreeze 3188:Fuel types 2732:2020-03-13 2666:2020-03-13 2236:"Solvents" 2200:2023-09-01 2051:2019-12-16 1664:17 January 1539:References 1464:March 2020 1399:oils, and 1238:March 2020 1208:newspapers 1050:Production 958:-mediated 941:lipophilic 796:> 2,000 647:Pictograms 629:Flammable 495:Molar mass 364:1P9D0Z171K 222:ChemSpider 158:3D model ( 137:CAS Number 3627:Uric acid 3610:vitamin E 3600:vitamin E 3538:Melatonin 3505:Edaravone 3494:vitamin A 3397:Fuel card 3354:Motor oil 3205:Biodiesel 2189:PubChem. 2168:1768-3254 2076:4 October 1487:, has an 1481:desmethyl 1427:Cosmetics 1401:jet fuels 1374:embalming 1358:cosmetics 1255:vitamin E 1178:talk page 1150:Reactions 980:antiviral 960:oxidation 638:labelling 346:GO7875000 270:204-881-4 262:EC Number 211:ChEMBL146 3591:Selenium 3500:Curcumin 3374:Gear oil 3235:Hydrogen 3225:Kerosene 3115:12 March 3086:12 March 3058:12 March 3052:ISID.org 3010:12 March 3005:12122334 2981:12122334 2965:systems. 2792:14 March 2787:32035997 2708:27357051 2661:79423095 2500:54366594 2379:Archived 2289:35766722 2176:26150290 1965:Archived 1952:Archived 1936:15172835 1818:23122098 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Index

FS Class E.321
Skeletal formula of butylated hydroxytoluene
Ball-and-stick model of the butylated hydroxytoluene molecule
Preferred IUPAC name
CAS Number
128-37-0
JSmol
Interactive image
ChEBI
CHEBI:34247
ChEMBL
ChEMBL146
ChemSpider
13835296
ECHA InfoCard
100.004.439
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EC Number
E number
(antioxidants, ...)
KEGG
D02413
PubChem
31404
RTECS number
UNII
1P9D0Z171K
CompTox Dashboard
DTXSID2020216
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