Names | |
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Preferred IUPAC name 2-tert-Butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol (mixture) | |
Other names
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Identifiers | |
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3D model (JSmol) | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.042.315 |
E number | E320 (antioxidants, ...) |
PubChem CID | |
UNII |
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CompTox Dashboard (EPA) | |
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Properties | |
C11H16O2 | |
Molar mass | 180.247 g/mol |
Appearance | Waxy solid |
Density | 1.0587 g/cm3 at 20 °C |
Melting point | 48 to 55 °C (118 to 131 °F; 321 to 328 K) |
Boiling point | 264 to 270 °C (507 to 518 °F; 537 to 543 K) |
Insoluble in water | |
Solubility | Freely soluble in ethanol, methanol, propylene glycol; soluble in fats and oils |
Refractive index (nD) | 1.5303 at 589.3 nm [2] |
Related compounds | |
Related compounds | Butylated hydroxytoluene |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
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. [3] BHA has been used in food since around 1947. [4]
BHA consists of a mixture of two isomeric organic compounds, 2-tert-butyl-4-hydroxyanisole and 3-tert-butyl-4-hydroxyanisole. It is prepared from 4-methoxyphenol and isobutylene.
The conjugated aromatic ring of BHA is able to stabilize free radicals, sequestering them. By acting as free radical scavengers, further free radical reactions are prevented.
Since 1947, BHA has been added to edible fats and fat-containing foods for its antioxidant properties as it prevents rancidification of food which creates objectionable odors. [5] It has been assigned the E number E320. It is often combined with a similar chemical, butylated hydroxytoluene (BHT). [4]
BHA also is commonly used in medicines, such as cholecalciferol (vitamin D3), isotretinoin, lovastatin, and simvastatin, among others.
The U.S. National Institutes of Health report that BHA is reasonably anticipated to be a human carcinogen based on evidence of carcinogenicity in experimental animals. In particular, when administered in high doses as part of their diet, BHA causes papillomas and squamous cell carcinomas of the forestomach in rats and Syrian golden hamsters. [6] In mice, there is no carcinogenic effect; [6] in fact, there is evidence of a protective effect against the carcinogenicity of other chemicals. [5]
When examining human population statistics, the usual low intake levels of BHA show no significant association with an increased risk of cancer. [7] The state of California has, however, listed BHA as a carcinogen. [8]
The European Commission has conducted an evaluation of literature. They noted the lack of potential for the compound to induce carcinogenic effects in humans; studies showing carcinogenic effects in hamsters are not relevant to humans (which lack a forestomach). Also noted is that endocrine disruption, if any, is only likely to be present at levels vastly exceeding the intake as a food. [9]
The International Agency for Research on Cancer (IARC) – Summaries & Evaluations stated butylated hydroxyanisole was tested for carcinogenicity in two experiments in rats and in two experiments in hamsters by administration in the diet, inducing benign and malignant tumours of the forestomach. [10]
One of its metabolites is TBHQ (t-butylhydroquinone), a preservative made infamous by food writer Michael Pollan. [4]
Aspartame is an artificial non-saccharide sweetener 200 times sweeter than sucrose and is commonly used as a sugar substitute in foods and beverages. It is a methyl ester of the aspartic acid/phenylalanine dipeptide with brand names NutraSweet, Equal, and Canderel. Aspartame was approved by the US Food and Drug Administration (FDA) in 1974, and then again in 1981, after approval was revoked in 1980.
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 useable lifetimes. Food 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.
Food preservation includes processes that make food more resistant to microorganism growth and slow the oxidation of fats. This slows down the decomposition and rancidification process. Food preservation may also include processes that inhibit visual deterioration, such as the enzymatic browning reaction in apples after they are cut during food preparation. By preserving food, food waste can be reduced, which is an important way to decrease production costs and increase the efficiency of food systems, improve food security and nutrition and contribute towards environmental sustainability. For instance, it can reduce the environmental impact of food production.
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.
Butylated hydroxytoluene (BHT), also known as dibutylhydroxytoluene, is a lipophilic organic compound, chemically a derivative of phenol, that is useful for its antioxidant properties. BHT is widely used to prevent free radical-mediated oxidation in fluids 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.
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.
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.
The International Agency for Research on Cancer is an intergovernmental agency forming part of the World Health Organization of the United Nations. Its role is to conduct and coordinate research into the causes of cancer. It also collects and publishes surveillance data regarding the occurrence of cancer worldwide.
Caffeic acid is an organic compound that is classified as a hydroxycinnamic acid. This yellow solid consists of both phenolic and acrylic functional groups. It is found in all plants because it is an intermediate in the biosynthesis of lignin, one of the principal components of woody plant biomass and its residues.
Ethoxyquin (EMQ) is a quinoline-based antioxidant used as a food preservative in certain countries and originally to control scald on pears after harvest. It is used as a preservative in some pet foods to slow the development of rancidity of fats. Ethoxyquin is also used in some spices to prevent color loss due to oxidation of the natural carotenoid pigments.
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.
Gum base is the non-nutritive, non-digestible, water-insoluble masticatory delivery system used to carry sweeteners, flavors, and any other substances in chewing gum and bubble gum. It provides all the basic textural and masticatory properties of gum.
Vinyl bromide is a simple vinyl halide. It is a colorless liquid. It is produced from ethylene dibromide. It is mainly used as a comonomer to confer fire retardant properties to acrylate polymers.
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.
A co-carcinogen is a chemical that promotes the effects of a carcinogen in the production of cancer. Usually, the term is used to refer to chemicals that are not carcinogenic on their own, such that an equivalent amount of the chemical is insufficient to initiate carcinogenesis. A chemical can be co-carcinogenic with other chemicals or with nonchemical carcinogens, such as UV radiation.
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.
PhIP (2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine) is one of the most abundant heterocyclic amines (HCAs) in cooked meat. PhIP is formed at high temperatures from the reaction between creatine or creatinine, amino acids, and sugar. PhIP formation increases with the temperature and duration of cooking and also depends on the method of cooking and the variety of meat being cooked. The U.S. Department of Health and Human Services National Toxicology Program has declared PhIP as "reasonably anticipated to be a human carcinogen". International Agency for Research on Cancer (IARC), part of World Health Organization, has classified PhIP as IARC Group 2B carcinogen. There is sufficient evidence in experimental animals, as well as in vitro models, for the carcinogenicity of PhIP.
Camlin Fine Sciences Ltd., formerly known as Camlin Fine Chemicals, is an Indian corporation that manufactures chemicals to improve the shelf life of food and other products, aromatic compounds, and performance chemicals. CFS has emerged as the largest producer of food antioxidants such as tert-Butylhydroquinone (TBHQ) and Butylated hydroxyanisole (BHA). It is also one of the world's leading Vanillin producers.