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BUTYLATED HYDROXYTOLUENE

CAS Number: 128-37-0 
EC Number: 204-881-4
E number: E321 
MDL number: MFCD00011644


PROPERTIES

Chemical formula: C15H24O
Molar mass: 220.356 g/mol
Appearance: White to yellow powder
Odor: Slight, phenolic
Density: 1.048 g/cm3
Melting point: 70 °C (158 °F; 343 K) 
Boiling point: 265 °C (509 °F; 538 K) 
Solubility in water: 1.1 mg/L (20 °C)
log P: 5.32
Vapor pressure: 0.01 mmHg (20 °C)


APPLICATIONS

Butylated hydroxytoluene 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.

As antioxidant in pharmaceuticals, cosmetics and  oil& fat in food.
Delay or prevent oxidative rancidity of oil and fat and loss of fat-soluble vitamins.
Butylated hydroxytoluene Can be used alone or in combination with synergists such as citric acid and phosphoric acid.
Butylated hydroxytoluene has antiviral activity and can be used for treatment of lip surface simple cell rash.

Butylated hydroxytoluene is used in food, cosmetics and industrial fluids to prevent oxidation and free radical formation.
Butylated hydroxytoluene (butylated hydroxytoluene) is a lab-made chemical that is added to foods as a preservative. People also use it as medicine.
Also, Butylated hydroxytoluene is used to treat genital herpes and acquired immunodeficiency syndrome (AIDS).
Some people apply Butylated hydroxytoluene directly to the skin for cold sores.

Butylated hydroxytoluene is an antioxidant. 
Butylated hydroxytoluene may damage the protective outer layer of viral cells. 
This may keep the viruses from multiplying and/or doing more damage.

Butylated hydroxytoluene is a synthetic phenolic compound mainly used as an antioxidant and preservative in the food industry. 
Butylated hydroxytoluene is used to prevent the lipid oxidation in oils and fat-containing foods.

Butylated hydroxytoluene is used in: 

-Beverage ingredients
-Food ingredients
-Food preservatives
-Personal care ingredients
-Skin care ingredients


Food additive

Butylated hydroxytoluene is primarily used as an antioxidant food additive.
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.
Butylated hydroxytoluene 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", while 9 CFR § 381.147](f) allows up to 0.01% in poultry "by fat content". 
Butylated hydroxytoluene is permitted in the European Union under E321.

Butylated hydroxytoluene is used as a preservative ingredient in some foods. 
With this usage Butylated hydroxytoluene maintains freshness or prevents spoilage; it may be used to decrease the rate at which the texture, color, or flavor of food changes.
Some food companies have voluntarily eliminated Butylated hydroxytoluene from their products or have announced that they were going to phase it out.

Butylated hydroxytoluene is a synthetic phenolic compound mainly used as an antioxidant and preservative in the food industry. 
Butylated hydroxytoluene is used to prevent the lipid oxidation in oils and fat-containing foods.
Butylated hydroxytoluene, a cresol derivative, is an additive used as an antioxidant in foods, such as packet cake mixes, potato crisps, salted peanuts, and dehydrated mashed potatoes. 

Butylated hydroxytoluene (BHT) is a man-made chemical commonly used as a preservative in processed foods. 
Similar to the synthetic preservative butylated hydroxyanisole (BHA) with which it is often used, Butylated hydroxytoluene is an antioxidant that is soluble in oils and animal fats (it actually has greater solubility than does BHA). 
Both BHA and Butylated hydroxytoluene are used to extend shelf life of processed foods by reducing the occurrence of oxidation and rancidity. 
Instead of being added directly to the food itself, Butylated hydroxytoluene is usually added to the packaging material from where it vaporizes into the food during storage. 

Since it may be classified as an incidental food additive when used in this manner, it does not legally need to be listed with other ingredients on the food label.
Processed foods most likely to contain Butylated hydroxytoluene include chewing gum, active dry yeast, frozen convenience foods, prepared cereal products, prepared snacks, dried and processed meat, potato flakes, enriched rice products and shortening. 
Butylated hydroxytoluene is also a chemical preservative used in animal feeds and drugs; therefore eatomg non-organic meats and dairy products may be another way in which exposure occurs. 
In addition to its use in food preservation, BHA is also used in the manufacture of rubber, tires and petroleum and is an ingredient in some cosmetics.

While Butylated hydroxytoluene is on the Federal Drug Administrations Generally Recognized as Safe (GRAS) list of food additives, it carries with it risk of toxicity. 
Although not been enough research has been conducted involving humans to establish whether or not Butylated hydroxytoluene is a carcinogen (chemical capable of causing cancer), limited evidence in animals suggests that BHT is carcinogenic. 
Some of Butylated hydroxytoluene's potential carcinogenicity may come from its ability to cause toxic disruption of cell signaling, a process where chemical information is transferred from one cell to another or between different structures within the same cell. 

Proper cellular communication is not only important for optimal functioning of the bodys systems, but researchers now believe that poor communication between cells may be one of the causes of overgrowth of cells, a condition which eventually leads to cancer.
Butylated hydroxytoluene has been found to have other some adverse effects in animals including inhibiting normal growth patterns and causing reversible liver enlargement. 
At high levels in animals, Butylated hydroxytoluene has caused significant brain and behavioral changes. 

Since Butylated hydroxytoluene has been found to inhibit the enzymes that white blood cells (phagocytes) use to destroy bacteria, Butylated hydroxytoluene disrupts the proper functioning of the immune system. 
Additionally, Butylated hydroxytoluene seems to be capable of uncoupling a critical cellular energy-producing process known as phosphorylation with the result being a diminished supply of cellular energy available to power the cells, and therefore, the body.

Antioxidant used in foods, cosmetics, petroleum products, etc. 
It may inhibit some neoplasms and facilitate others.


Antioxidant

Butylated hydroxytoluene is also used as an antioxidant in products such as metalworking fluids, cosmetics, pharmaceuticals, rubber, transformer oils, and embalming fluid. 
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. 

Butylated hydroxytoluene is also used to prevent peroxide formation in organic ethers and other solvents and laboratory chemicals.
It is added to certain monomers as a polymerisation inhibitor to facilitate their safe storage.
Some additive products contain Butylated hydroxytoluene as their primary ingredient, while others contain the chemical merely as a component of their formulation, sometimes alongside butylated hydroxyanisole (BHA).


Use in cosmetics

BHA (butylated hydroxyanisole) and BHT (butylated hydroxytoluene) are closely related synthetic antioxidants used as preservatives in lipsticks and moisturizers, among other cosmetics. 
BHA (butylated hydroxyanisole) and BHT (butylated hydroxytoluene) are also widely used as food preservatives.


DESCRIPTION

Butylated hydroxytoluene (BHT), also known as dibutylhydroxytoluene, is a lipophilic organic compound, chemically a derivative of phenol, that is useful for its antioxidant properties.
Butylated hydroxytoluene 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 Butylated hydroxytoluene 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 Butylated hydroxytoluene was noncarcinogenic in an animal model, societal concerns over its broad use have been expressed. 
Butylated hydroxytoluene has also been postulated as an antiviral drug, but as of March 2020, use of Butylated hydroxytoluene 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.

Butylated Hydroxytoluene is an organic chemical composed of 4-methylphenol modified with tert-butyl groups at positions 2 and 6. 
Butylated hydroxytoluene (BHT) inhibits autoxidation of unsaturated organic compounds.
Moreover, Butylated hydroxytoluene is a white crystalline solid. 
Butylated hydroxytoluene is a natural product found in Betula pendula, Polysiphonia stricta, and other organisms with data available.

Butylated hydroxytoluene, a cresol derivative, is an additive used as an antioxidant in foods, such as packet cake mixes, potato crisps, salted peanuts, and dehydrated mashed potatoes. 
Butylated hydroxytoluene, commonly known as BHT, is an organic compound that is used in the food, cosmetic, and pharmaceutical industry as an antioxidant. 
Butylated Hydroxytoluene is a substituted derivative of phenol. 

Butylated Hydroxytoluene helps to prevent the formation of free radicals and oxidation. 
When used in food products, it delays oxidative rancidity of fats and oils, and prevents loss of activity of oil-soluble vitamins. 
Butylated Hydroxytoluene may be found in pharmaceutical gels, creams and liquid or gelatin capsules, tablets and other pharmaceutical dosage forms. 
The ability of oral BHT to lead to cancer is a controversial topic, but most food industries have replaced it with butylated hydroxyanisole (BHA). 
A large review from 2002 concluded that Butylated Hydroxytoluene is safe for use on the skin in cosmetics.


NATURAL OCCURENCE 

Phytoplankton, including the green algae Botryococcus braunii, as well as three different cyanobacteria (Cylindrospermopsis raciborskii, Microcystis aeruginosa and Oscillatoria sp.) are capable of producing Butylated hydroxytoluene as a natural product. 
The fruit lychee also produces Butylated hydroxytoluene in its pericarp.
Several fungi (example Aspergillus conicus) living in olives produce Butylated hydroxytoluene.


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: 

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.


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. 
Butylated hydroxytoluene stops this autocatalytic reaction by converting peroxy radicals to hydroperoxides. 
Butylated hydroxytoluene 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.


HEALTH EFFECTS

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

Nevertheless, the World Health Organization discussed a possible link between Butylated hydroxytoluene 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 Center for Science in the Public Interest puts Butylated hydroxytoluene in its "caution" column and recommends avoiding it.

Based on various, disparate primary research reports, Butylated hydroxytoluene 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 particles. 

The action of Butylated hydroxytoluene 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 Butylated hydroxytoluene use, topically against genital herpes lesions, a report of inhibitory activity in vitro 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 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 Butylated hydroxytoluene.

Hence, at present, the results do not present a scientific consensus in favour of the conclusion of the general antiviral potential of Butylated hydroxytoluene 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 Butylated hydroxytoluene products as an antiviral therapy or prophylactic.


Why Butylated Hydroxytoluene (BHT) is Restricted?

-Butylated hydroxytoluene is very toxic to aquatic life and is also a skin and eye irritant.1
-Butylated hydroxytoluene can be transferred from the plastic packaging to the fabric which can react with the nitrogen oxide in the air and in alkaline conditions can form nitrobenzenes. This reaction can cause phenolic yellowing. 
Although this can occur with all colors, it is most visible with white and pastel colors. 
Darker colors may appear duller in appearance.
-The solvent in the adhesive tape used to seal the packaging can leach the Butylated hydroxytoluene out of the packaging film and onto the garment.


SYNONYMS

2,6-Di-tert-butyl-p-cresol
3,5-Di-tert-butyl-4-hydroxytoluene
DBPC
BHT
E321
AO-29
Avox BHT
Additin RC 7110
Dibutylated hydroxytoluene
4-Methyl-2,6-di-tert-butyl phenol
3,5-(Dimethylethyl)-4-hydroxytoluene
Phenol, 2,6-bis(1,1-dimethylethyl)-4-methyl-
p-Cresol, 2,6-di-tert-butyl-
Advastab 401
Antioxidant DBPC 
Antioxidant KB 
Antioxidant 29 
Antioxidant 30 
Antioxidant 4K
AO 29
AO 4K

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