Butylated hydroxytoluene

Last updated
Butylated hydroxytoluene
2,6-bis(1,1-dimethylethyl)-4-methylphenol.svg
Butylated hydroxytoluene 3D ball.png
Names
Preferred IUPAC name
2,6-Di-tert-butyl-4-methylphenol
Other names
  • 2,6-Di-tert-butyl-p-cresol
  • 2,6-DI-tert-butyl-4-methylphenol
  • 3,5-Di-tert-butyl-4-hydroxytoluene
  • 2,6 ditertiary-butyl-4-methyl phenol
  • 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
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.439 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 204-881-4
E number E321 (antioxidants, ...)
KEGG
PubChem CID
RTECS number
  • GO7875000
UNII
  • 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 Yes check.svgY
    Key: NLZUEZXRPGMBCV-UHFFFAOYSA-N Yes check.svgY
  • 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
    Key: NLZUEZXRPGMBCV-UHFFFAOYAU
  • CC(C)(C)c1cc(C)cc(c1O)C(C)(C)C
Properties
C15H24O
Molar mass 220.356 g/mol
AppearanceWhite to yellow powder
Odor Slight, phenolic
Density 1.048 g/cm3
Melting point 70 °C (158 °F; 343 K) [1]
Boiling point 265 °C (509 °F; 538 K) [1]
1.1 mg/L (20 °C) [2]
log P 5.32 [3]
Vapor pressure 0.01 mmHg (20 °C) [4]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Flammable
GHS labelling:
GHS-pictogram-pollu.svg
Warning
H410
P273, P391, P501
NFPA 704 (fire diamond)
NFPA 704.svgHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
1
0
Flash point 127 °C (261 °F; 400 K) [1]
Lethal dose or concentration (LD, LC):
> 2,000 mg/kg (dermal, rat) [5]
NIOSH (US health exposure limits):
PEL (Permissible)
None [4]
REL (Recommended)
TWA 10 mg/m3 [4]
IDLH (Immediate danger)
N.D. [4]
Safety data sheet (SDS) [6]
Related compounds
Related compounds
 Butylated hydroxyanisole
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Butylated hydroxytoluene (BHT), also known as dibutylhydroxytoluene, is a lipophilic organic compound, chemically a derivative of phenol, that is useful for its antioxidant properties. [7] 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 U.S. F.D.A.—which considers BHT to be "generally recognized as safe"—allow small amounts to be 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 drug regulatory agency for use as an antiviral.[ citation needed ]

Contents

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. [8] The fruit lychee also produces BHT in its pericarp. [9] Several fungi (for example Aspergillus conicus ) living in olives produce BHT. [10]

Production

Industrial production

The chemical synthesis of BHT in industry has involved the reaction of p-cresol (4-methylphenol) with isobutylene (2-methylpropene), catalyzed by sulfuric acid: [11]

CH3(C6H4)OH + 2 CH2=C(CH3)2 → ((CH3)3C)2CH3C6H2OH

Alternatively, BHT has been prepared from 2,6-di-tert-butylphenol by hydroxymethylation or aminomethylation followed by hydrogenolysis.[ citation needed ]

Reactions

The species behaves as a synthetic 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. [12] [13] The electron-donating alkyl groups on the ortho and para positions of BHT increase the electron density of the phenolic hydroxyl moiety through the inductive effect and the hyperconjugation effect, [14] reduce the bond dissociation energy of the phenolic hydroxyl group, and enhance its reactivity to lipid free radicals. Meanwhile, the phenoxy radical generated by BHT is stabilized due to the delocalization of unpaired electrons around the aromatic ring [14] [15] and the steric hindrance effect of ortho tert-butyl groups. [16] [17] Isobutene is one of the possible degradation products formed by BHT oxidation with computational studies suggesting that there are two possible mechanism that can lead to isobutene formation with the OH addition pathways at the C2 site of BHT more likely to result in isobutene formation than pathways of H abstracts from the t-butyl group. [18]

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. [19]

Food additive

BHT is primarily used as an antioxidant food additive. [20] 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. [21] [ page needed ] It is approved for use in the U.S. by the Food and Drug Administration: For example, 21 CFR § 137.350(a)(4) allows BHT up to 0.0033% by weight in "enriched rice", [22] while 9 CFR § 381.147](f)(1) allows up to 0.01% in poultry "by fat content". [23] It is permitted in the European Union under E321. [24]

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. [25]

Some food companies have voluntarily eliminated BHT from their products or have announced that they were going to phase it out. [26]

Antioxidant

BHT is also used as an antioxidant in products such as metalworking fluids, cosmetics, pharmaceuticals, rubber, transformer oils, and embalming fluid. [27] [28] In the petroleum industry, where BHT is known as the fuel additive AO-29, it is used in hydraulic fluids, turbine and gear oils, and jet fuels. [27] [29] [ page needed ] BHT is also used to prevent peroxide formation in organic ethers and other solvents and laboratory chemicals. [30] It is added to certain monomers as a polymerisation inhibitor to facilitate their safe storage. [31] 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). [32]

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. [33]

Health effects

Like many closely related phenol antioxidants, BHT has low acute toxicity [5] (e.g., the desmethyl analog of BHT, 2,6-di-tert-butylphenol, has an LD50 of >9 g/kg [11] ). The US Food and Drug Administration classifies BHT as generally recognized as safe (GRAS) food preservative when used in an approved manner. [34] [35] In 1979, the National Cancer Institute determined that BHT was noncarcinogenic in a mouse model. [21] [ needs update ]

Nevertheless, the World Health Organization discussed a possible link between BHT and cancer risk in 1986, [36] [ page needed ][ verification needed ][ needs update ] 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. [37] [38] [39] [ non-primary source needed ] Because of this uncertainty, the Center for Science in the Public Interest puts BHT in its "caution" column and recommends avoiding it. [40]

Based on various, disparate primary research reports, BHT has been suggested to have anti-viral activity, [41] 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. [42] [43] [ non-primary source needed ] 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, [44] [45] [46] which are established methods of viral disinfection secondary to methods of chemical oxidation and UV irradiation. [47] [ citation needed ] In addition, there is a report of BHT use, topically against genital herpes lesions, [48] [ non-primary source needed ] a report of inhibitory activity in vitro against pseudorabies (in cell culture), [49] [ non-primary source needed ] 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). [49] [50] [ non-primary source needed ] The relevance of other reports, regarding influenza in mice, is not easily discerned. [51] [52] [ non-primary source needed ] Notably, this series of primary research reports does not support a general conclusion of independent confirmation of the original research results, [53] nor are there critical reviews appearing thereafter, in secondary sources, for the various host-virus systems studied with BHT. [54] [55]

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. [56] [57] [58]

Related Research Articles

Antioxidants are compounds that inhibit oxidation, a chemical reaction that can produce free radicals. Autoxidation leads to degradation of organic compounds, including living matter. Antioxidants are frequently added to industrial products, such as polymers, fuels, and lubricants, to extend their usable lifetimes. Foods are also treated with antioxidants to forestall spoilage, in particular the rancidification of oils and fats. In cells, antioxidants such as glutathione, mycothiol, or bacillithiol, and enzyme systems like superoxide dismutase, can prevent damage from oxidative stress.

A preservative is a substance or a chemical that is added to products such as food products, beverages, pharmaceutical drugs, paints, biological samples, cosmetics, wood, and many other products to prevent decomposition by microbial growth or by undesirable chemical changes. In general, preservation is implemented in two modes, chemical and physical. Chemical preservation entails adding chemical compounds to the product. Physical preservation entails processes such as refrigeration or drying. Preservative food additives reduce the risk of foodborne infections, decrease microbial spoilage, and preserve fresh attributes and nutritional quality. Some physical techniques for food preservation include dehydration, UV-C radiation, freeze-drying, and refrigeration. Chemical preservation and physical preservation techniques are sometimes combined.

<span class="mw-page-title-main">Butylated hydroxyanisole</span> Chemical compound

Butylated hydroxyanisole (BHA) is a synthetic, waxy, solid petrochemical. Its antioxidant properties have caused it to be widely used as a preservative in food, food packaging, animal feed, cosmetics, pharmaceuticals, rubber, and petroleum products. BHA has been used in food since around 1947.

Rancidification is the process of complete or incomplete autoxidation or hydrolysis of fats and oils when exposed to air, light, moisture, or bacterial action, producing short-chain aldehydes, ketones and free fatty acids.

<span class="mw-page-title-main">Isobutylene</span> Unsaturated hydrocarbon compound (H2C=C(CH3)2)

Isobutylene is a hydrocarbon with the chemical formula (CH3)2C=CH2. It is a four-carbon branched alkene (olefin), one of the four isomers of butylene. It is a colorless flammable gas, and is of considerable industrial value.

In industrial chemistry, a stabilizer or stabiliser is a chemical that is used to prevent degradation. Above all, heat and light stabilizers are added to plastic and rubber materials because they ensure safe processing and protect products against aging and weathering. In particular polyvinyl chloride would not be possible without stabilizers.

2,4-Dimethyl-6-<i>tert</i>-butylphenol Chemical compound

2,4-Dimethyl-6-tert-butylphenol is the organic compound with the formula Me2(tert-Bu)C6H2OH (Me = methyl, tert-Bu = tertiary butyl). It is a colorless oil that is classified as an alkylated phenol.

2,6-Di-<i>tert</i>-butylphenol Chemical compound

2,6-Di-tert-butylphenol is an organic compound with the structural formula 2,6-((CH3)3C)2C6H3OH. This colorless solid alkylated phenol and its derivatives are used industrially as UV stabilizers and antioxidants for hydrocarbon-based products ranging from petrochemicals to plastics. Illustrative of its usefulness, it prevents gumming in aviation fuels.

<span class="mw-page-title-main">Propyl gallate</span> Chemical compound

Propyl gallate, or propyl 3,4,5-trihydroxybenzoate, is an ester formed by the condensation of gallic acid and propanol. Since 1948, this antioxidant has been added to foods containing oils and fats to prevent oxidation. As a food additive, it is used under the E number E310.

<i>tert</i>-Butylhydroquinone Chemical compound

tert-Butylhydroquinone is a synthetic aromatic organic compound which is a type of phenol. It is a derivative of hydroquinone, substituted with a tert-butyl group.

<span class="mw-page-title-main">Octyl gallate</span> Chemical compound

Octyl gallate is the ester of 1-octanol and gallic acid. As a food additive, it is used under the E number E311 as an antioxidant and preservative.

Warmed-over flavor is an unpleasant characteristic usually associated with meat which has been cooked and then refrigerated. The deterioration of meat flavor is most noticeable upon reheating. As cooking and subsequent refrigeration is the case with most convenience foods containing meat, it is a significant challenge to the processed food industry. The flavor is variously described as "rancid," "stale," and like "cardboard," and even compared to "damp dog hair." Warmed-over flavor is caused by the oxidative decomposition of lipids in the meat into chemicals which have an unpleasant taste or odor. This decomposition process begins after cooking or processing and is aided by the release of naturally occurring iron in the meat.

<span class="mw-page-title-main">Naturally occurring phenols</span> Group of chemical compounds

In biochemistry, naturally occurring phenols are natural products containing at least one phenol functional group. Phenolic compounds are produced by plants and microorganisms. Organisms sometimes synthesize phenolic compounds in response to ecological pressures such as pathogen and insect attack, UV radiation and wounding. As they are present in food consumed in human diets and in plants used in traditional medicine of several cultures, their role in human health and disease is a subject of research. Some phenols are germicidal and are used in formulating disinfectants.

2,4,6-Tri-<i>tert</i>-butylphenol Chemical compound

2,4,6-Tri-tert-butylphenol (2,4,6-TTBP) is a phenol symmetrically substituted with three tert-butyl groups and thus strongly sterically hindered. 2,4,6-TTBP is a readily oxidizable aromatic compound and a weak acid. It oxidizes to give the deep-blue 2,4,6-tri-tert-butylphenoxy radical. 2,4,6-TTBP is related to 2,6-di-tert-butylphenol, which is widely used as an antioxidant in industrial applications. These compounds are colorless solids.

Tris(2,4-di-<i>tert</i>-butylphenyl)phosphite Chemical compound

Tris(2,4-di-tert-butylphenyl)phosphite is an organophosphorus compound with the formula [(C4H9)2C6H3O]3P. This white solid is a widely used stabilizer in polymers where it functions as a secondary antioxidant. It also reduces discoloration (yellowing) of plastics. The compound is a phosphite ester formed by the reaction of 2,4-di-tert-butylphenol with phosphorus trichloride. It is an approved food contact materials in the US.

Pentaerythritol tetrakis(3,5-di-<i>tert</i>-butyl-4-hydroxyhydrocinnamate) Chemical compound

Pentaerythritol tetrakis(3,5-di-tert-butyl-4-hydroxyhydrocinnamate) is a chemical compound composed of four sterically hindered phenols linked through a pentaerythritol core. It is used as primary antioxidant for stabilizing polymers, particularly polyethylene and polypropylene.

2-<i>tert</i>-Butylphenol Organic aromatic compound

2-tert-Butyl phenol is an organic compound with the formula (CH3)3CC6H4OH. It is one of three isomeric tert-butyl phenols. It is a colorless oil that dissolves in basic water. It can be prepared by acid-catalyzed alkylation of phenol with isobutene.

Octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate is a hindered phenolic antioxidant commonly used as a polymer stabiliser.

Tris(3,5-di-<i>tert</i>-butyl-4-hydroxybenzyl) isocyanurate Chemical compound

Tris(3,5-di-tert-butyl-4-hydroxybenzyl) isocyanurate is a chemical compound used as a polymer stabilizer in plastics. Like other hindered phenols it acts as a primary antioxidant. More than 1000 tonnes per year are used in the EU.

References

  1. 1 2 3 "ICSC 0841 - BUTYLATED HYDROXYTOLUENE". www.inchem.org. March 1999.
  2. ↑ KEMI Anställd [KEMI Staff] (1994). "Teknisk beskrivning av ämnet—2,6-Bis(tert-butyl)-4-metylfenol 1994 [Information on substances—2,6-Bis(tert-butyl)-4-methylphenol 1994]" (in Swedish and English). Sundyberg, SE: KEMI [Swedish Chemicals Agency]. Archived from the original on 11 August 2011. Retrieved 14 March 2020. Vattenlöslighet: 1,1 mg/L (20 °C) [Water solubility: 1.1 mg/L (20 °C)][ better source needed ]
  3. ↑ "2,6-di-tert-butyl-4-methylphenol". www.chemsrc.com.
  4. 1 2 3 4 NIOSH Pocket Guide to Chemical Hazards. "#0246". National Institute for Occupational Safety and Health (NIOSH).
  5. 1 2 Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  6. ↑ "Safety data for 2,6-di-tert-butyl-p-cresol". ptcl.chem.ox.ac.uk. Archived from the original on 21 June 2002. Retrieved 17 January 2022.
  7. ↑ 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". Eur. J. Med. Chem. 101: 295–312. doi:10.1016/j.ejmech.2015.06.026. PMID   26150290.
  8. ↑ Babu B, Wu JT (December 2008). "Production of Natural Butylated Hydroxytoluene as an Antioxidant by Freshwater Phytoplankton" (PDF). Journal of Phycology. 44 (6): 1447–1454. Bibcode:2008JPcgy..44.1447B. doi:10.1111/j.1529-8817.2008.00596.x. PMID   27039859. S2CID   26084768.
  9. ↑ 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". Food Chemistry. 136 (2): 563–8. doi:10.1016/j.foodchem.2012.08.089. PMID   23122098.
  10. ↑ 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". European Journal of Lipid Science and Technology. 119 (11): 1600343. doi:10.1002/ejlt.201600343.
  11. 1 2 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 Article Online Posting Date: June 15, 2000.
  12. ↑ 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". Journal of the American Chemical Society. 103 (21): 6472–6477. doi:10.1021/ja00411a035.
  13. ↑ Fujisawa, Seiichiro; Kadoma, Yoshinori; Yokoe, Ichiro (July 2004). "Radical-scavenging activity of butylated hydroxytoluene (BHT) and its metabolites". Chemistry and Physics of Lipids. 130 (2): 189–195. doi:10.1016/j.chemphyslip.2004.03.005. PMID   15172835.
  14. 1 2 Huang, Mou-Tuan; Ho, Chi-Tang; Lee, Chang Y., eds. (1992-10-01). "Thermal Degradation of Phenolic Antioxidants". Phenolic Compounds in Food and Their Effects on Health II: Antioxidants and Cancer Prevention. ACS Symposium Series. Vol. 507. Washington, DC: American Chemical Society. pp. 200–218. doi:10.1021/bk-1992-0507.ch015. ISBN   978-0-8412-2476-6.
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  16. ↑ Breese, K.D.; Lamèthe, J.-F.; DeArmitt, C. (2000). "Improving synthetic hindered phenol antioxidants: learning from vitamin E". Polymer Degradation and Stability. 70 (1): 89–96. doi:10.1016/S0141-3910(00)00094-X.
  17. ↑ Ariffin, Azhar; Rahman, Noorsaadah Abdul; Yehye, Wageeh A.; Alhadi, Abeer A.; Kadir, Farkaad A. (2014). "PASS-assisted design, synthesis and antioxidant evaluation of new butylated hydroxytoluene derivatives". European Journal of Medicinal Chemistry. 87: 564–577. doi:10.1016/j.ejmech.2014.10.001. PMID   25299680.
  18. ↑ Zhou, Junwei; Chen, Hongrui; Chen, Jianfa; Wan, Daihong; Zhang, Huikun; Wang, Rong; Xie, Daiqian; Mao, Chengli (2022-05-26). "Mechanisms and Kinetics Studies of Butylated Hydroxytoluene Degradation to Isobutene". The Journal of Physical Chemistry A. 126 (20): 3210–3218. doi:10.1021/acs.jpca.2c01961. ISSN   1089-5639.
  19. ↑ US Dept of Health & Human Services. Household Products Database. Archived 2015-09-05 at the Wayback Machine .US EPA. InertFinder. . US National Library of Medicine. Haz-Map. Archived 2015-09-05 at the Wayback Machine . US National Library of Medicine. Hazardous Substances Data Bank. .
  20. ↑ "CFR - Code of Federal Regulations Title 21".
  21. 1 2 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 ]
  22. ↑ "CFR - Code of Federal Regulations Title 21". www.accessdata.fda.gov.
  23. ↑ "9 CFR 3, Part 381.147 (Restrictions on the Use of Substances in Poultry Processing)". Food and Drug Administration . Archived from the original on 2009-07-09. Retrieved 2019-12-16.
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  25. ↑ "Food Additives & Ingredients > Overview of Food Ingredients, Additives & Colors". www.fda.gov. 20 February 2020. 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)[.]
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  27. 1 2 Yehye, Wageeh A.; Rahman, Noorsaadah Abdul; Ariffin, Azhar; Abd Hamid, Sharifah Bee; Alhadi, Abeer A.; Kadir, Farkaad A.; Yaeghoobi, Marzieh (2015-08-28). "Understanding the chemistry behind the antioxidant activities of butylated hydroxytoluene (BHT): a review". European Journal of Medicinal Chemistry. 101: 295–312. doi:10.1016/j.ejmech.2015.06.026. ISSN   1768-3254. PMID   26150290.
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  33. ↑ Slavova, Siana (23 June 2023). "New restrictions for Butylated Hydroxytoluene (BHT) and Acid Yellow 3 apply as of July 2023". Obelis Group.
  34. ↑ "SCOGS (Select Committee on GRAS Substances)". FDA.gov.
  35. ↑ "CFR—Code of Federal Regulations Title 21". FDA.gov.
  36. ↑ Butylated hydroxytoluene (BHT) (PDF) (Report). Vol. 40. World Health Organization: International Agency For Research On Cancer. 1986. pp. 161–206. Archived (PDF) from the original on 5 September 2015.[ page needed ]
  37. ↑ Kensler, TW; Egner, PA; Trush, MA; Bueding, E; Groopman, JD (1985). "Modification of aflatoxin B1 binding to DNA in vivo in rats fed phenolic antioxidants, ethoxyquin and a dithiothione". Carcinogenesis. 6 (5): 759–763. doi:10.1093/carcin/6.5.759. PMID   3924431.
  38. ↑ 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". Cancer Letters. 104 (1): 49–53. doi:10.1016/0304-3835(96)04228-0. PMID   8640745.
  39. ↑ Franklin, R. A (1976). "Butylated hydroxytoluene in sarcoma-prone dogs". Lancet. 1 (7972): 1296. doi:10.1016/s0140-6736(76)91766-9. PMID   73719. S2CID   54366594.
  40. ↑ "Two Preservatives to Avoid?". Berkeley Wellness. University of California Berkeley. February 1, 2011. Retrieved 12 September 2015.
  41. ↑ 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).
  42. ↑ Snipes W, Person S, Keith A, Cupp J (4 April 1975). "Butylated Hydroxytoluene Inactivated Lipid-Containing Viruses". Science. 188 (4183): 64–66. Bibcode:1975Sci...188...64S. doi:10.1126/science.163494. PMID   163494.
  43. ↑ Kim, K. S; Moon, H. M; Sapienza, V; Carp, R. I; Pullarkat, R (1978). "Inactivation of cytomegalovirus and Semliki Forest virus by butylated hydroxytoluene". The Journal of Infectious Diseases. 138 (1): 91–4. doi:10.1093/infdis/138.1.91. PMID   210237.
  44. ↑ Rutala, William A.; Weber, David J. (January 2015). "Disinfection, Sterilization, and Control of Hospital Waste". Mandell, Douglas, and Bennett's Principles and Practice of Infectious Diseases: 3294–3309.e4. doi: 10.1016/B978-1-4557-4801-3.00301-5 . ISBN   9781455748013. S2CID   79423095 . Retrieved 2020-03-13.
  45. ↑ Cook, Nigel; Knight, Angus; Richards, Gary P. (1 July 2016). "Persistence and Elimination of Human Norovirus in Food and on Food Contact Surfaces: A Critical Review". Journal of Food Protection. 79 (7): 1273–94. doi: 10.4315/0362-028X.JFP-15-570 . PMID   27357051.
  46. ↑ Ferris Jabr (13 March 2020). "Why Soap Works - The New York Times". The New York Times. Retrieved 2020-03-13.
  47. ↑ Kampf G, Todt D, Pfaender S, Steinmann E (March 2020). "Persistence of Coronaviruses on Inanimate Surfaces and Their Inactivation With Biocidal Agents" (PDF). J. Hosp. Infect. 104 (3): 246–251. doi: 10.1016/j.jhin.2020.01.022 . PMC   7132493 . PMID   32035997 . Retrieved 14 March 2020.
  48. ↑ Richards, J. T; Katz, M. E; Kern, E. R (1985). "Topical butylated hydroxytoluene treatment of genital herpes simplex virus infections of guinea pigs". Antiviral Research. 5 (5): 281–90. doi:10.1016/0166-3542(85)90042-7. PMID   2998276.
  49. 1 2 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". American Journal of Veterinary Research. 47 (9): 1892–5. PMID   3021025.
  50. ↑ Brugh, M (1977). "Butylated hydroxytoluene protects chickens exposed to Newcastle disease virus". Science. 197 (4310): 1291–2. Bibcode:1977Sci...197.1291B. doi:10.1126/science.897670. PMID   897670.
  51. ↑ 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". Vestnik Akademii Meditsinskikh Nauk SSSR (in Russian) (11): 63–8. PMID   2623936.
  52. ↑ Chetverikova LK, Inozemtseva LI (1996). "Role of Lipid Peroxidation in the Pathogenesis of Influenza and Search for Antiviral Protective Agents". Vestn Ross Akad Med Nauk (in Russian). 3 (3): 37–40. PMID   8672960.
  53. ↑ 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.
  54. ↑ 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 Chosidow O, Lebrun-Vignes B (April 2002). "Traitements locaux, antiviraux ou non, dans la prise en charge de l'herpès oro-facial et génital (grossesse et nouveau-né exclus)" [Local treatments using antiviral and non-antiviral drugs for herpes facialis and genitalis (excluding pregnant females and neonates at risk)]. Annales de Dermatologie et de Vénéréologie. 129 (4–C2): 635–645. PMID   12122334 . Retrieved 12 March 2020. DOI, DERM-04-2002-129-4-C2-0151-9638-101019-ART18
  55. ↑ "(BHT OR butylated hydroxytoluene) AND antiviral [TIAB] - PubMed - NCBI". www.ncbi.nlm.nih.gov.
  56. ↑ ISID Web Tools (12 March 2020). "You searched for BHT". ISID.org. International Society for Infectious Diseases (ISID). Retrieved 12 March 2020. There are 0 results for 'BHT'
  57. ↑ "ESCMID—Search—Website Search—Search in Category". European Society of Clinical Microbiology and Infectious Diseases (ESCMID). Retrieved 12 March 2020. Search for "bht".
  58. ↑ See for instance, this and the following two references: IDSA Web Tools (12 March 2020). "Search Results". IDSociety.org. Infectious Diseases Society of America (IDSA). Retrieved 12 March 2020. No results found
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