Butylated hydroxytoluene: Difference between revisions

{{redirect|E321|the Italian electric locomotive|FS Class E.321}}

{{Chembox

| Watchedfields = changed

| verifiedrevid = 443492116

| ImageFile = 2,6-bis(1,1-dimethylethyl)-4-methylphenol.svg

| ImageSize = 160px

| ImageAlt = Skeletal formula of butylated hydroxytoluene

| ImageFile1 = Butylated hydroxytoluene 3D ball.png

| ImageSize1 = 180

| ImageAlt1 = Ball-and-stick model of the butylated hydroxytoluene molecule

| PIN = 2,6-Di-''tert''-butyl-4-methylphenol

| OtherNames = {{ubl

| 2,6-Di-''tert''-butyl-''p''-cresol

| 2,6-DI-tert-butyl-4-methylphenol

| 3,5-Di-''tert''-butyl-4-hydroxytoluene

| DBPC

| BHT

| E321

| AO-29

| Avox BHT

| Antioxidant 264

| Additin RC 7110

| Dibutylated hydroxytoluene

| 4-Methyl-2,6-di-tert-butyl phenol

| 3,5-(Dimethylethyl)-4-hydroxytoluene

}}

| Section1 = {{Chembox Identifiers

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChEBI_Ref = {{ebicite|correct|EBI}}

| PubChem = 31404

| EINECS = 204-881-4

| RTECS = GO7875000

| Section2 = {{Chembox Properties

| C=15 | H=24 | O=1

| MolarMassUnit = g/mol

| Appearance = White to yellow powder

| Odor = Slight, [[phenol]]ic

| Density = 1.048 g/cm³

| Solubility = 1.1{{nbsp}}mg/L (20{{nbsp}}°C)<ref>{{cite web | author = KEMI Anställd [KEMI Staff] | date = 1994 | title = Teknisk beskrivning av ämnet—2,6-Bis(tert-butyl)-4-metylfenol 1994 [Information on substances—2,6-Bis(tert-butyl)-4-methylphenol 1994] | language = sv,en | location = Sundyberg, SE | publisher = KEMI [Swedish Chemicals Agency] | url = http://apps.kemi.se/flodessok/floden/kemamne/BHT.htm | archive-url = https://web.archive.org/web/20110811153038/http://apps.kemi.se/flodessok/floden/kemamne/BHT.htm | archive-date = 11 August 2011 | access-date = 14 March 2020 | quote = Vattenlöslighet: 1,1 mg/L (20 °C) [Water solubility: 1.1 mg/L (20&nbsp;°C)]}}{{better source needed|date = March 2020}}<!--ANY COMPENDIUM/DATABASE NOT CITING THE SOURCE OF THE DATA PRESENTED IS NOT, FROM A PHYSICOCHEMICAL PERSPECTIVE, RELIABLE. THERE ARE MANY WAYS TO DETERMINE PHYSICAL PARAMETERS, AND NOT ALL ARE CREATED EQUAL, AS EARLY WORK ON LFER, pKa AND ClogP PREDICTION, ETC., HAVE MADE CLEAR. THIS 1.1 mg/L RAISES THE QUESTION OF HOW DETERMINED.--></ref>

| MeltingPtC = 70

| MeltingPt_ref = <ref name=inchem>{{cite web|url=http://www.inchem.org/documents/icsc/icsc/eics0841.htm|title=ICSC 0841 - BUTYLATED HYDROXYTOLUENE|website=www.inchem.org|date = March 1999}}</ref>

| BoilingPtC = 265

| BoilingPt_ref =<ref name=inchem />

| pKa =

| VaporPressure = 0.01{{nbsp}}mmHg (20{{nbsp}}°C)<ref name=PGCH />

| LogP = 5.32<ref name="chemsrc">{{cite web|url=https://www.chemsrc.com/en/cas/128-37-0_1067745.html|title=2,6-di-tert-butyl-4-methylphenol|website=www.chemsrc.com}}</ref>

| Section7 = {{Chembox Hazards

| ExternalSDS = <ref>{{cite web |url=http://ptcl.chem.ox.ac.uk/MSDS/DI/2,6-di-t-butyl-p-cresol.html |title=Safety data for 2,6-di-tert-butyl-p-cresol |website=ptcl.chem.ox.ac.uk |access-date=17 January 2022 |archive-url=https://web.archive.org/web/20020621043339/http://ptcl.chem.ox.ac.uk/MSDS/DI/2,6-di-t-butyl-p-cresol.html |archive-date=21 June 2002 }}</ref>

| NFPA-H = 2 | NFPA-F = 1 | NFPA-R = 0 | NFPA-S =

| MainHazards = Flammable

| FlashPtC = 127

| FlashPt_ref = <ref name=inchem />

| GHSPictograms = {{GHS09}}

| GHSSignalWord = Warning

| HPhrases = {{H-phrases|410}}

| PPhrases = {{P-phrases|273|391|501}}

| PEL = None<ref name=PGCH>{{PGCH|0246}}</ref>

| IDLH = N.D.<ref name=PGCH />

| REL = TWA 10{{nbsp}}mg/m³<ref name=PGCH />

| LD50 = > 2,000{{nbsp}}mg/kg (dermal, rat)<ref name=GESTIS>{{GESTIS|ZVG=14260}}</ref>

| Section8 = {{Chembox Related

| OtherCompounds = [[Butylated hydroxyanisole]]

'''Butylated hydroxytoluene''' ('''BHT'''), also known as '''dibutylhydroxytoluene''', is a [[lipophilic]] [[organic compound]], chemically a derivative of [[phenol]], that is useful for its [[antioxidant]] properties.<ref>{{cite journal |vauthors=Yehye WA, Rahman NA, Ariffin A, Abd Hamid SB, Alhadi AA, Kadir FA, Yaeghoobi M | date = 28 August 2015 | title = Understanding the Chemistry Behind the Antioxidant Activities of Butylated Hydroxytoluene (BHT): A Review | journal = Eur. J. Med. Chem. | volume = 101 | pages = 295–312 | doi = 10.1016/j.ejmech.2015.06.026 | pmid = 26150290 }}</ref> BHT is widely used to prevent [[free radical]]-mediated [[oxidation]] in fluids (e.g. fuels, oils) and other materials, and the regulations overseen by the [[United States Food and Drug Administration|U.S. F.D.A.]]—which considers BHT to be "[[generally recognized as safe]]"—allow small amounts to be [[food additive|added to foods]]. Despite this, and the earlier determination by the [[National Cancer Institute]] that BHT was noncarcinogenic in an animal model, societal concerns over its broad use have been expressed. BHT has also been postulated as an [[antiviral]] 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 [[Regulation of therapeutic goods|drug regulatory agency]] for use as an antiviral.{{Citation needed|date=May 2023}}

== Natural occurrence ==

[[Phytoplankton]], including the [[green algae]] ''[[Botryococcus braunii]]'', as well as three different [[cyanobacteria]] (''[[Cylindrospermopsis raciborskii]]'', ''[[Microcystis aeruginosa]]'' and ''[[Oscillatoria]]'' sp.) are capable of producing BHT as a [[natural product]].<ref name="BHTalgae">{{cite journal |vauthors=Babu B, Wu JT |title=Production of Natural Butylated Hydroxytoluene as an Antioxidant by Freshwater Phytoplankton |journal=Journal of Phycology |volume=44 |issue=6 |pages=1447–1454 |date=December 2008 |url= http://ntur.lib.ntu.edu.tw/bitstream/246246/162863/1/22.pdf |doi=10.1111/j.1529-8817.2008.00596.x|pmid=27039859 |bibcode=2008JPcgy..44.1447B |s2cid=26084768 }}</ref> The fruit [[lychee]] also produces BHT in its [[pericarp]].<!-- For this to appear, it needs to be clear which of the preceding sets of isolations this detail applies to: Confirmation was made via [[gas chromatography–mass spectrometry]] analysis.--><ref>{{cite journal |last1=Jiang |first1=G |last2=Lin |first2=S |last3=Wen |first3=L |last4=Jiang |first4=Y |last5=Zhao |first5=M |last6=Chen |first6=F |last7=Prasad |first7=KN |last8=Duan |first8=X |last9=Yang |first9=B |title=Identification of a novel phenolic compound in litchi (Litchi chinensis Sonn.) pericarp and bioactivity evaluation. |journal=Food Chemistry |date=15 January 2013 |volume=136 |issue=2 |pages=563–8 |name-list-style=vanc |doi=10.1016/j.foodchem.2012.08.089 |pmid=23122098}}</ref> Several fungi (for example ''[[Aspergillus conicus]]'') living in olives produce BHT.<ref>{{cite journal|title = Butylated hydroxytoluene (BHT) emitted by fungi naturally occurring in olives during their pre-processing storage for improving olive oil stability|first1= Ines|last1= Gharbi|first2= Manel|last2= Issaoui|first3=Sinda|last3= El Gharbi|first4 =Nour-Eddine |last4=Gazzeh|first5= Meriem|last5= Tekeya|first6 =Beligh|last6 = Mechri|first7= Guido|last7= Flamini|first8 =Mohamed |last8=Hammami|journal = European Journal of Lipid Science and Technology |volume = 119|issue = 11|date = 2017|page= 1600343|doi = 10.1002/ejlt.201600343}}</ref>

== Production ==

===Industrial production===

The [[chemical synthesis]] of BHT in industry has involved the reaction of [[p-Cresol|''p''-cresol]] (4-methylphenol) with [[isobutylene]] (2-methylpropene), catalyzed by [[sulfuric acid]]:

<ref name=Ullmann>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 ''Ullmann's Encyclopedia of Industrial Chemistry'', Wiley-VCH, Weinheim, 2002. {{doi|10.1002/14356007.a19_313}}

Alternatively, BHT has been prepared from [[2,6-Di-tert-butylphenol|2,6-di-''tert''-butylphenol]] by hydroxymethylation or aminomethylation followed by [[hydrogenolysis]].{{citation needed|date = March 2020}}

== Reactions ==

{{one source|section|date = March 2020}}

The species behaves as a synthetic [[structural analog|analog]] of [[vitamin E]], primarily acting as a terminating agent that suppresses [[autoxidation]], a process whereby unsaturated (usually) organic compounds are attacked by atmospheric oxygen. BHT stops this [[autocatalytic]] reaction by converting peroxy radicals to hydroperoxides. It effects this function by donating a hydrogen atom:

:RO₂• + ArOH → ROOH + ArO•

:RO₂• + ArO• → nonradical products

where R is [[alkyl]] or [[aryl]], and where ArOH is BHT or related phenolic antioxidants. Each BHT consumes two peroxy radicals.<ref>{{cite journal | author = Burton G. W., Ingold K. U. | year = 1981 | title = Autoxidation of biological molecules. 1. Antioxidant activity of vitamin E and related chain-breaking phenolic antioxidants in vitro | journal = Journal of the American Chemical Society | volume = 103 | issue = 21| pages = 6472–6477 | doi = 10.1021/ja00411a035 }}</ref><ref>{{Cite journal |last1=Fujisawa |first1=Seiichiro |last2=Kadoma |first2=Yoshinori |last3=Yokoe |first3=Ichiro |date=July 2004 |title=Radical-scavenging activity of butylated hydroxytoluene (BHT) and its metabolites |url=https://linkinghub.elsevier.com/retrieve/pii/S0009308404000349 |journal=Chemistry and Physics of Lipids |language=en |volume=130 |issue=2 |pages=189–195 |doi=10.1016/j.chemphyslip.2004.03.005|pmid=15172835 }}</ref>

== Applications ==

BHT is listed by the [[NIH]] 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.<ref>US Dept of Health & Human Services. Household Products Database. [http://hpd.nlm.nih.gov/] {{Webarchive|url=https://web.archive.org/web/20150905052301/http://hpd.nlm.nih.gov/|date=2015-09-05}}.US EPA. InertFinder. [http://iaspub.epa.gov/apex/pesticides/f?p=175:1:]. US National Library of Medicine. Haz-Map. [http://hazmap.nlm.nih.gov/index.php] {{Webarchive|url=https://web.archive.org/web/20150905065151/http://hazmap.nlm.nih.gov/index.php|date=2015-09-05}}. US National Library of Medicine. Hazardous Substances Data Bank. [http://toxnet.nlm.nih.gov/cgi-bin/sis/htmlgen?HSDB].</ref>

=== Food additive ===

BHT is primarily used as an antioxidant food additive.<ref>{{Cite web|url=https://www.accessdata.fda.gov/scripts/cdrh/cfdocs/cfcfr/CFRSearch.cfm?fr=172.115|title=CFR - Code of Federal Regulations Title 21}}</ref> In the United States, it is classified as [[generally recognized as safe]] (GRAS) based on a [[National Cancer Institute]] study from 1979 in rats and mice.<ref name=NTP>[https://ntp.niehs.nih.gov/go/tr150abs Bioassay of Butylated Hydroxytoluene (BHT) for Possible Carcinogenicity], National Cancer Institute, CARCINOGENESIS Technical Report Series No. 150, 1979, 128 pp [[National Institutes of Health]]{{page needed|date=March 2020}}</ref>{{page needed|date=March 2020}} It is approved for use in the U.S. by the [[Food and Drug Administration]]: For example, 21 [[Code of Federal Regulations|CFR]] §&nbsp;137.350(a)(4) allows BHT up to 0.0033% by weight in "enriched rice",<ref>{{cite web|url=https://www.accessdata.fda.gov/scripts/cdrh/cfdocs/cfcfr/CFRSearch.cfm?fr=137.350|title=CFR - Code of Federal Regulations Title 21|website=www.accessdata.fda.gov}}</ref> while 9 CFR §&nbsp;381.147](f)(1) allows up to 0.01% in [[poultry]] "by fat content".<ref>{{Cite web |url=https://www.fda.gov/Food/FoodSafety/RetailFoodProtection/FoodCode/FoodCode2001/ucm092716.htm |title=9 CFR 3, Part 381.147 (Restrictions on the Use of Substances in Poultry Processing) |website=[[Food and Drug Administration]] |access-date=2019-12-16 |archive-url=https://web.archive.org/web/20090709085417/http://www.fda.gov/Food/FoodSafety/RetailFoodProtection/FoodCode/FoodCode2001/ucm092716.htm |archive-date=2009-07-09 }}</ref> It is permitted in the European Union under [[E number|E321]].<ref>{{cite web|title = Scientific Opinion on the re-evaluation of butylated hydroxytoluene BHT (E 321) as a food additive {{!}} European Food Safety Authority|url = http://www.efsa.europa.eu/en/efsajournal/pub/2588|website = www.efsa.europa.eu|access-date = 4 October 2015 |date = 7 March 2012}}</ref>

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.<ref>{{cite web |url=https://www.fda.gov/food/ingredientspackaginglabeling/foodadditivesingredients/ucm094211.htm#types |title=Food Additives & Ingredients > Overview of Food Ingredients, Additives & Colors |quote=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, citric acid, sodium benzoate, calcium propionate, sodium erythorbate, sodium nitrite, calcium sorbate, potassium sorbate, BHA, BHT, EDTA, tocopherols (Vitamin E)[.] |website=www.fda.gov|date=20 February 2020 }}</ref>

Some food companies have voluntarily eliminated BHT from their products or have announced that they were going to phase it out.<ref name=atl>{{cite journal|author=Hamblin, James|title=The Food Babe: Enemy of Chemicals|journal=The Atlantic|date=11 February 2015|url=https://www.theatlantic.com/health/archive/2015/02/the-food-babe-enemy-of-chemicals/385301/|access-date=12 September 2015}}</ref>

=== Antioxidant ===

BHT is also used as an antioxidant in products such as [[metalworking fluids]], [[cosmetics]], [[pharmaceuticals]], [[rubber]], [[transformer oil]]s, and [[embalming]] fluid.<ref name=":0">{{Cite journal |last1=Yehye |first1=Wageeh A. |last2=Rahman |first2=Noorsaadah Abdul |last3=Ariffin |first3=Azhar |last4=Abd Hamid |first4=Sharifah Bee |last5=Alhadi |first5=Abeer A. |last6= Kadir |first6=Farkaad A. |last7=Yaeghoobi |first7=Marzieh |date=2015-08-28 |title=Understanding the chemistry behind the antioxidant activities of butylated hydroxytoluene (BHT): a review |url= https://pubmed.ncbi.nlm.nih.gov/26150290/ |journal=European Journal of Medicinal Chemistry |volume=101 |pages=295–312 |doi=10.1016/j.ejmech.2015.06.026 |issn=1768-3254 |pmid=26150290}}</ref><ref>{{Cite web |last=PubChem |title=Butylated Hydroxytoluene |url=https://pubchem.ncbi.nlm.nih.gov/compound/31404 |access-date=2023-09-01 |website=pubchem.ncbi.nlm.nih.gov |language=en}}</ref> In the [[petroleum industry]], where BHT is known as the [[List of gasoline additives|fuel additive]] [[Antioxidant#Industrial uses|AO-29]], it is used in [[hydraulic fluid]]s, [[turbine]] and [[gear]] oils, and [[jet fuel]]s.<ref name=":0" /><ref name=Handbook>Michael Ash, Irene Ash, ''Handbook of Preservatives'', Synapse Information Resources, 2004. {{ISBN|1-890595-66-7}}.{{page needed|date = March 2020}}</ref>{{page needed|date = March 2020}} BHT is also used to prevent [[Organic peroxide|peroxide]] formation in organic [[ether]]s and other solvents and laboratory chemicals.<ref>{{Cite web|url=https://www.sigmaaldrich.com/chemistry/solvents/learning-center/stabilizer-systems.html|title=Solvents|website = Millipore Sigma}}</ref> It is added to certain [[monomers]] as a [[polymerisation inhibitor]] to facilitate their safe storage.<ref>{{Cite journal |last1=Grohmann |first1=Caio Vinícius Signorelli |last2=Sinhoreti |first2=Mário Alexandre Coelho |last3=Soares |first3=Eveline Freitas |last4=Oliveira |first4=Robson Ferraz de |last5=Souza |first5=Eduardo José de Carvalho |last6=Geraldeli |first6=Saulo |date=24 June 2022 |title=Effect of a polymerization inhibitor on the chemomechanical properties and consistency of experimental resin compo |journal=Brazilian Dental Journal |volume=33 |issue=3 |pages=92–98 |doi=10.1590/0103-6440202204242 |pmid=35766722 |pmc=9645198 }}</ref> Some additive products contain BHT as their primary ingredient, while others contain the chemical merely as a component of their formulation, sometimes alongside [[butylated hydroxyanisole]] (BHA).<ref name="sciam13">{{cite news |title=BHA and BHT: A Case for Fresh? |url=https://www.scientificamerican.com/article/bha-and-bht-a-case-for-fresh/ |publisher=Scientific American |date=19 December 2013}}</ref>

=== Cosmetics ===

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.<ref>{{cite web |last1=Slavova |first1=Siana |title=New restrictions for Butylated Hydroxytoluene (BHT) and Acid Yellow 3 apply as of July 2023 |url=https://www.obelis.net/news/new-restrictions-bht-acid-yellow-3-cosmetic-products/ |website=Obelis Group |language=en |date=23 June 2023}}</ref>

== Health effects ==

{{update | section | date = March 2020}}

Like many closely related [[phenol antioxidant]]s, BHT has low acute toxicity<ref name=GESTIS/> (e.g., the [[desmethyl]] analog of BHT, [[2,6-di-tert-butylphenol]], has an {{LD50}} of >9&nbsp;g/kg<ref name=Ullmann />). The [[US Food and Drug Administration]] classifies BHT as [[generally recognized as safe]] (GRAS) food preservative when used in an approved manner.<ref>{{cite web|url=https://www.accessdata.fda.gov/scripts/fdcc/?set=SCOGS|title=SCOGS (Select Committee on GRAS Substances)|work=FDA.gov}}</ref><ref>{{cite web|url=https://www.accessdata.fda.gov/scripts/cdrh/cfdocs/cfCFR/CFRSearch.cfm?fr=172.115|title=CFR—Code of Federal Regulations Title 21|work=FDA.gov}}</ref> In 1979, the [[National Cancer Institute]] determined that BHT was noncarcinogenic in a [[mouse model]].<ref name=NTP />{{update after|2020|3}}

Nevertheless, the [[World Health Organization]] discussed a possible link between BHT and cancer risk in 1986,<ref name = "WHOReport1986">{{cite report | year = 1986 | title = Butylated hydroxytoluene (BHT) | url = https://monographs.iarc.fr/ENG/Monographs/vol1-42/mono40.pdf | archive-url = https://web.archive.org/web/20150905203436/http://monographs.iarc.fr/ENG/Monographs/vol1-42/mono40.pdf | archive-date = 5 September 2015 | url-status = live | publisher = World Health Organization: International Agency For Research On Cancer | volume = 40 | pages = 161–206}}{{page needed|date=March 2020}}</ref>{{page needed|date=March 2020}}<!--PAGE RANGES of 1-2 pages are requested by the guidance; 45 pages are too long to allow veritication, reasonably and readily.-->{{verification needed|date = March 2020}}{{update after|2020|3}} 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.<ref>{{Cite journal | pmid = 3924431| year = 1985| last1 = Kensler| first1 = TW| title = Modification of aflatoxin B1 binding to DNA in vivo in rats fed phenolic antioxidants, ethoxyquin and a dithiothione| journal = Carcinogenesis| volume = 6| issue = 5| pages = 759–763| last2 = Egner| first2 = PA| last3 = Trush| first3 = MA| last4 = Bueding| first4 = E| last5 = Groopman| first5 = JD|author-link5=John Groopman| doi=10.1093/carcin/6.5.759}}</ref><ref>{{Cite journal | pmid = 8640745| year = 1996| last1 = Williams| first1 = GM| title = Inhibition of the hepatocarcinogenicity of aflatoxin B1 in rats by low levels of the phenolic antioxidants butylated hydroxyanisole and butylated hydroxytoluene| journal = Cancer Letters| volume = 104| issue = 1| pages = 49–53| last2 = Iatropoulos| first2 = M. J| doi=10.1016/0304-3835(96)04228-0}}</ref><ref>{{Cite journal | pmid = 73719| year = 1976| last1 = Franklin| first1 = R. A| title = Butylated hydroxytoluene in sarcoma-prone dogs| journal = Lancet| volume = 1| issue = 7972| page = 1296 | doi = 10.1016/s0140-6736(76)91766-9 | s2cid = 54366594}}</ref>{{primary source inline|date=March 2020}} Because of this uncertainty, the [[Center for Science in the Public Interest]] puts BHT in its "caution" column and recommends avoiding it.<ref name=ucb>{{cite web|title=Two Preservatives to Avoid?|url=http://www.berkeleywellness.com/healthy-eating/food-safety/article/two-preservatives-avoid|website=Berkeley Wellness|publisher=University of California Berkeley|access-date=12 September 2015|date=February 1, 2011}}</ref>

Based on various, disparate primary research reports, BHT has been suggested to have anti-viral activity,<ref>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 research team (the pair by Chetverikova et al. being the nearest to this).</ref> 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 particles.<ref name=CuppSci75>{{Cite journal |vauthors=Snipes W, Person S, Keith A, Cupp J | date = 4 April 1975 | title = Butylated Hydroxytoluene Inactivated Lipid-Containing Viruses | journal = Science | volume = 188 | issue = 4183 | pages = 64–66 | doi = 10.1126/science.163494 | pmid = 163494 | bibcode = 1975Sci...188...64S }}</ref><ref>{{Cite journal | pmid =210237| year =1978| last1 =Kim| first1 =K. S| title =Inactivation of cytomegalovirus and Semliki Forest virus by butylated hydroxytoluene| journal =The Journal of Infectious Diseases| volume =138| issue =1| pages =91–4| last2 =Moon| first2 =H. M| last3 =Sapienza| first3 =V| last4 =Carp| first4 =R. I| last5 =Pullarkat| first5 =R| doi=10.1093/infdis/138.1.91}}</ref>{{primary source inline|date=March 2020}} 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,<ref>{{cite journal|url=https://www.sciencedirect.com/science/article/pii/B9781455748013003015 |title=Disinfection, Sterilization, and Control of Hospital Waste |journal=Mandell, Douglas, and Bennett's Principles and Practice of Infectious Diseases |date= January 2015|pages=3294–3309.e4 |access-date=2020-03-13 |doi=10.1016/B978-1-4557-4801-3.00301-5|last1=Rutala |first1=William A. |last2= Weber |first2=David J. |isbn=9781455748013 |s2cid=79423095 |doi-access=free }}</ref><ref>{{cite journal|first1 = Nigel|last1= Cook|first2 = Angus|last2= Knight|first3= Gary P. |last3= Richards |title=Persistence and Elimination of Human Norovirus in Food and on Food Contact Surfaces: A Critical Review |journal=Journal of Food Protection |volume=79 |issue=7 |doi-access= free |pages= 1273–94 |date= 1 July 2016 |pmid=27357051 |doi=10.4315/0362-028X.JFP-15-570 }}</ref><ref>{{cite news|author=Ferris Jabr |url=https://www.nytimes.com/2020/03/13/health/soap-coronavirus-handwashing-germs.html |title=Why Soap Works - The New York Times |newspaper=The New York Times |date= 13 March 2020|access-date=2020-03-13}}</ref> which are established methods of viral disinfection secondary to methods of chemical oxidation and UV irradiation.<ref>{{cite journal |vauthors=Kampf G, Todt D, Pfaender S, Steinmann E | date = March 2020 | title = Persistence of Coronaviruses on Inanimate Surfaces and Their Inactivation With Biocidal Agents | journal = J. Hosp. Infect. | volume = 104 | issue = 3 | pages = 246–251 | doi = 10.1016/j.jhin.2020.01.022 | pmid = 32035997 | url = https://www.journalofhospitalinfection.com/article/S0195-6701(20)30046-3/pdf | format = PDF | access-date = 14 March 2020 | doi-access = free | pmc = 7132493 }}</ref>{{citation needed| date = March 2020}} In addition, there is a report of BHT use, topically against genital herpes lesions,<ref>{{Cite journal | pmid =2998276| year =1985| last1 =Richards| first1 =J. T| title =Topical butylated hydroxytoluene treatment of genital herpes simplex virus infections of guinea pigs| journal =Antiviral Research| volume =5| issue =5| pages =281–90| last2 =Katz| first2 =M. E| last3 =Kern| first3 =E. R| doi=10.1016/0166-3542(85)90042-7}}</ref>{{primary source inline|date=March 2020}} a report of inhibitory activity ''in vitro'' against pseudorabies (in cell culture),<ref name=PirtleSacks1986>{{Cite journal | pmid =3021025| year =1986| last1 =Pirtle| first1 =E. C| title =Antiviral effectiveness of butylated hydroxytoluene against pseudorabies (Aujeszky's disease) virus in cell culture, mice, and swine| journal =American Journal of Veterinary Research| volume =47| issue =9| pages =1892–5| last2 =Sacks| first2 = J. M| last3 =Nachman| first3 =R. J}}</ref>{{primary source inline|date=March 2020}} 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).<ref name=PirtleSacks1986/><ref>{{cite journal | doi = 10.1126/science.897670 | pmid = 897670 | title = Butylated hydroxytoluene protects chickens exposed to Newcastle disease virus | journal = Science | volume = 197 | issue = 4310 | pages = 1291–2 | year = 1977 | last1 = Brugh | first1 = M | bibcode = 1977Sci...197.1291B }}</ref>{{primary source inline|date=March 2020}} The relevance of other reports, regarding influenza in mice, is not easily discerned.<ref>{{Cite journal | pmid = 2623936 | language = ru| year = 1989| last1 = Chetverikova| first1 = L. K| title = Factors of Antiviral Resistance in the Pathogenesis of Influenza in Mice| journal = Vestnik Akademii Meditsinskikh Nauk SSSR| issue = 11| pages = 63–8| last2 = Ki'Ldivatov| first2 = I. Iu| last3 = Inozemtseva| first3 = L. I| last4 = Kramskaia| first4 = T. A| last5 = Filippov| first5 = V. K| last6 = Frolov| first6 = B. A}}</ref><ref>{{Cite journal | author = Chetverikova LK, Inozemtseva LI | title = Role of Lipid Peroxidation in the Pathogenesis of Influenza and Search for Antiviral Protective Agents | journal = Vestn Ross Akad Med Nauk | date = 1996 | volume = 3 | issue = 3 | pages = 37–40 | language = ru| pmid = 8672960 }}</ref>{{primary source inline|date=March 2020}} Notably, this series of primary research reports does not support a general conclusion of independent confirmation of the original research results,<ref>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 systems.</ref> nor are there critical reviews appearing thereafter, in secondary sources, for the various host-virus systems studied with BHT.<ref>Search of Pubmed in March 2020 with the main field search string, "(BHT OR butylated hydroxytoluene) AND antiviral [TIAB]", see next citation, to pull articles focused on antiviral effects of the agent produced a single review source, {{PMID|12122334}}, which is a review of the use of topical agents in treatment of herpes facialis and genitalis; this 18-year old review mentioning BHT in this topical application is irrelevant to its value as a general antiviral, and to its utility as an orally bioavailable agent in humans. See {{cite journal |vauthors=Chosidow O, Lebrun-Vignes B | date = April 2002 | title = Traitements locaux, antiviraux ou non, dans la prise en charge de l'herpès oro-facial et génital (grossesse et nouveau-né exclus) | trans-title = Local treatments using antiviral and non-antiviral drugs for herpes facialis and genitalis (excluding pregnant females and neonates at risk) | journal = Annales de Dermatologie et de Vénéréologie | volume = 129 | issue = 4–C2 | pages = 635–645 | pmid = 12122334 | url = https://www.em-consulte.com/en/article/153873 | access-date = 12 March 2020 | url-access = subscription | quote = DOI, DERM-04-2002-129-4-C2-0151-9638-101019-ART18 }}</ref><ref>{{cite web|url=https://pubmed.ncbi.nlm.nih.gov/?term=(BHT+OR+butylated+hydroxytoluene)+AND+antiviral+%5BTIAB%5D|title=(BHT OR butylated hydroxytoluene) AND antiviral [TIAB] - PubMed - NCBI|website=www.ncbi.nlm.nih.gov}}</ref>

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 advocated use of BHT products as an antiviral therapy or prophylactic.<ref>{{cite web|author = ISID Web Tools | date = 12 March 2020 | title=You searched for BHT| work = ISID.org | publisher = International Society for Infectious Diseases (ISID) | url=https://isid.org/search/BHT/|access-date= 12 March 2020| quote = There are 0 results for 'BHT'}}</ref><ref>{{cite web |title=ESCMID—Search—Website Search—Search in Category |website=European Society of Clinical Microbiology and Infectious Diseases (ESCMID) | url=https://www.escmid.org/search/ |access-date= 12 March 2020}} Search for "bht".</ref><ref>See for instance, this and the following two references: {{cite web|author = IDSA Web Tools | date = 12 March 2020 | title=Search Results| work = IDSociety.org | publisher = Infectious Diseases Society of America (IDSA) | url=https://www.idsociety.org/search-results?query=BHT#/score/DESC/0/BHT/|access-date= 12 March 2020| quote = No results found}}</ref>

== References ==

{{reflist}}

== External links ==

* [https://www.thoughtco.com/bha-and-bht-food-preservatives-607393 Chemistry of BHA and BHT Food Preservatives]

* [https://www.cdc.gov/niosh/npg/npgd0246.html CDC – NIOSH Pocket Guide to Chemical Hazards]

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