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CAS Number: 25013-16-5
121-00-6 (2-tert)
88-32-4 (3-tert)
E number: E320
EC Number: 246-563-8
MDL number: MFCD01779059
PROPERTIES
Chemical formula: 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)
Solubility in water: 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
APPLICATIONS
The primary use for Butylated hydroxyanisole is as an antioxidant and preservative in food, food packaging, animal feed, cosmetics, rubber, and petroleum products.
Butylated hydroxyanisole also is commonly used in medicines, such as cholecalciferol (Vitamin D3), isotretinoin, lovastatin, and simvastatin, among others.
Butylated hydroxyanisole is a volatile monohydric phenolic compound mainly used as an antioxidant and preservative in the food industry.
Butylated hydroxyanisole is used to preserve the flavor and color of oils due its ability to restrict the oxidation of short chain fatty acids.
Butylated hydroxyanisole is used primarily as an antioxidant and preservative in food, food packaging, animal feed, and cosmetics, and in rubber and petroleum products.
Food-grade Butylated hydroxyanisole contains over 85% 3-BHA and less than 15% 2-BHA, while cosmetic-grade Butylated hydroxyanisole contains 90% 3-BHA and 8% 2-BHA.
Since 1947, Butylated hydroxyanisole has been added to edible fats and fat-containing foods for its antioxidant properties.
Butylated hydroxyanisole is also used in foods cooked or fried in animal oils, because of its high thermal stability and its ability to remain active in baked and fried foods.
Butylated hydroxyanisole is added to butter, lard, meats, cereals, baked goods, sweets, beer, vegetable oils, potato chips, snack foods, nuts and nut products, dehydrated potatoes, and flavoring agents.
Butylated hydroxyanisole is used in sausage, poultry and meat products, dry mixes for beverages and desserts, glazed fruits, chewing gum, active dry yeast, defoaming agents for beet sugar and yeast, and emulsion stabilizers for shortening.
Butylated hydroxyanisole stabilizes the petroleum wax coatings of food packaging.
Butylated hydroxyanisole is considered by the U.S. Food and Drug Administration (FDA) to be generally recognized as safe when the antioxidant content does not exceed 0.02% by weight of the
food’s total fat or oil content.
Butylated hydroxyanisole is one of the primary antioxidants used in feeds, because it retards the oxidation of vitamin A, fats, and vegetable oils.
Butylated hydroxyanisole is an effective stabilizer for essential oils, paraffin, and polyethylenes.
Also, Butylated hydroxyanisole is used as an antioxidizing agent in a biomaterial made from polyurethane and polyethylene oxide used to make mainline catheters.
Butylated hydroxyanisole is used as a preservative and antioxidant in pharmaceutical preparations and cosmetic formulations containing fats and oils.
A 1981 FDA survey found that Butylated hydroxyanisole was used in 3,217 of 21,279 cosmetic formulations; the majority (88%) of the reported concentrations did not exceed 0.1%.
In that survey, use of Butylated hydroxyanisole was highest in lipstick formulations (1,256 products), followed by eye-shadow products.
For industrial use, Butylated hydroxyanisole has largely been replaced by tert-butylhydroquinone.
Butylated hydroxyanisole is mainly used as a synthetic antioxidant in food and cosmetics.
Butylated hydroxyanisole is being extensively studied for potential toxicity.
Also, Butylated hydroxyanisole is used to preserve the flavor and color of oils due its ability to restrict the oxidation of short chain fatty acids.
Butylated Hydroxyanisole (BHA) is an effective antioxidant used in lipid-containing foods to prevent or delay oxidation.
Butylated Hydroxyanisole preserves foods and extends shelf life.
At room temperature, it forms a white or yellowish waxy solid with faint aromatic odor.
For optimal effectiveness, Butylated Hydroxyanisole is typically mixed with the lipid component of a bakery formula prior to mixing the dough or batter.
In some cases, a Butylated Hydroxyanisole emulsion is sprayed topically after the product has been baked.
Incorporating Butylated Hydroxyanisole at 0.02% concentration in pastry and crackers can extend the product shelf life up to 33 days.
Similarly, soda cracker biscuits contain Butylated Hydroxyanisole up to 0.02% (based on lipid content).
One limitation with Butylated Hydroxyanisole is its incompatibility with ferric salts.
Butylhydroxyanisole (Butylated hydroxyanisole) is an antioxidant used as a food additive preservative.
Butylhydroxyanisole mediates liver toxicity, retardation in reproductive organ development and learning, and sleep deficit.
Additionally, Butylhydroxyanisole exerts neurotoxic effects and leads to disruption of the brain and nerve development.
Butylhydroxyanisole is a ferroptosis inducer.
BHA is widely used in:
-Baked goods
-Cereals
-Beverages
-Ice creams
-Edible fats and oils
-Food packaging
-Beverage ingredients
-Food ingredients
-Food preservatives
-Personal care ingredients
-Pharmaceutical chemicals
DESCRIPTION
Butylated hydroxyanisole (BHA) is an antioxidant consisting of a mixture of two isomeric organic compounds, 2-tert-butyl-4-hydroxyanisole and 3-tert-butyl-4-hydroxyanisole.
Butylated hydroxyanisole is prepared from 4-methoxyphenol and isobutylene.
Additionally, Butylated hydroxyanisole is a waxy solid used as a food additive with the E number E320.
The primary use for Butylated hydroxyanisole is as an antioxidant and preservative in food, food packaging, animal feed, cosmetics, rubber, and petroleum products.
Butylated hydroxyanisole also is commonly used in medicines, such as cholecalciferol (Vitamin D3), isotretinoin, lovastatin, and simvastatin, among others.
Butylated hydroxyanisole is an antioxidant which exists at room temperature as a white or slightly yellow, waxy solid with a faint characteristic odor.
Moreover, Butylated hydroxyanisole in commercial use consists of a mixture of 3-tert-butyl-4-hydroxyanisole (3-BHA) and 2-tert-butyl-4-hydroxyanisole (2-BHA).
Butylated hydroxyanisole is insoluble in water, but is soluble in fats, oils, propylene glycol, petroleum ether, chloroform, and 50% alcohol.
Butylated hydroxyanisole is a volatile monohydric phenolic compound mainly used as an antioxidant and preservative in the food industry.
Butylated hydroxyanisole is used to preserve the flavor and color of oils due its ability to restrict the oxidation of short chain fatty acids.
Butylated hydroxyanisole (C11H16O2), also known as BHA, is a food antioxidant that is available dissolved in propylene glycol.
Butylated hydroxyanisole comes as a white crystalline powder or a yellowish-white waxy solid.
Butylated hydroxyanisole is used in a wide range of cosmetics, foods, and pharmaceuticals.
When used in food products, it delays oxidative rancidity of fats and oils, and prevents loss of activity of oil-soluble vitamins.
Butylated hydroxyanisole may be found in pharmaceutical gels, creams and liquid or gelatin capsules, tablets and other pharmaceutical dosage forms.
Animals studies have shown tumors in rats and mice forestomachs at levels much higher than that consumed by humans.
Overall, the evidence does not support the occurrence of tumors when butylated hydroxyanisole is ingested at much lower levels.
Butylated hydroxyanisole retards rancidity in fats, oils, and oil-containing foods.
While some studies indicate it is safe, other studies demonstrate that it causes cancer in rats, mice, and hamsters.
Those cancers are controversial because they occur in the forestomach, an organ that humans do not have.
However, a chemical that causes cancer in at least one organ in three different species indicates that it might be carcinogenic in humans.
That is why the U.S. Department of Health and Human Services considers Butylated hydroxyanisole to be "reasonably anticipated to be a human carcinogen."
Nevertheless, the Food and Drug Administration still permits BHA to be used in foods.
This synthetic chemical can be replaced by safer chemicals (e.g., vitamin E), safer processes (e.g., packing foods under nitrogen instead of air), or can simply be left out (many brands of oily foods, such as potato chips, don't use any antioxidant).
ORIGIN
Butylated hydroxyanisole was first synthesized in the late 1940s as an effective antioxidant in various foods, cosmetics, packaging and other products.
Butylated hydroxyanisole is an aromatic compound synthesized from the reaction of 4-methoxyphenol and isobutylene.
Use of Butylated hydroxyanisole as an antioxidant in edible fats and foods containing fats dates back to 1947.
Due to its high thermal stability and ability to remain active, it is also used in foods cooked or fried in animal oils as well as in baked.
ANTIOXIDANT PROPERTIES
Since 1947, Butylated hydroxyanisole has been added to edible fats and fat-containing foods for its antioxidant properties as it prevents rancidification of food which creates objectionable odors.
Like butylated hydroxytoluene (BHT), the conjugated aromatic ring of Butylated hydroxyanisole is able to stabilize free radicals, sequestering them.
By acting as free radical scavengers, further free radical reactions are prevented.
REGULATIONS
Food and Drug Administration (FDA)
Butylated hydroxyanisole is generally recognized as safe for use in food when the total of antioxidants is not greater than 0.02% of fat or oil content.
Butylated hydroxyanisole may be used as a food additive permitted for direct addition to food for human consumption as prescribed in 21 CFR 172 and 166.
Moreover, Butylated hydroxyanisole may be used in the manufacture of food packaging materials, with a limit of addition to food of 0.005%.
Butylated hydroxyanisole may be used as an antioxidant in defoaming agents for processed foods, not to exceed 0.1% by weight of defoamer.
RESEARCH
The U.S. National Institutes of Health report that Butylated hydroxyanisole 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, Butylated hydroxyanisole causes papillomas and squamous cell carcinomas of the forestomach in rats and Syrian golden hamsters.
In mice, there is no carcinogenic effect; in fact, there is evidence of a protective effect against the carcinogenicity of other chemicals.
When examining human population statistics, the usual low intake levels of Butylated hydroxyanisole show no significant association with an increased risk of cancer.
The state of California has, however, listed Butylated hydroxyanisole as a carcinogen.
The European Commission has conducted an evaluation of literature.
They noted the lack of potential for Butylated hydroxyanisole 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.
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.
NUTRITION
Similar to other antioxidants, Butylated hydroxyanisole can neutralize free radicals in biological tissues.
So, Butylated hydroxyanisole has a potentially beneficial role in reducing the risk of cardiovascular and other diseases.
Recently, there has been some concern about potential adverse effects of Butylated hydroxyanisole which helped support consumers demand to replace all synthetic antioxidants with natural ones.
CARCINOGENICITY
Butylated hydroxyanisole (BHA) is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals. Cancer Studies in Experimental Animals Dietary exposure to Butylated hydroxyanisole caused benign and malignant tumors of the forestomach (papilloma and squamous-cell carcinoma) in rats of both sexes and in male mice and hamsters.
Since Butylated hydroxyanisole was listed in the Sixth Annual Report on Carcinogens, an additional study in experimental animals has been identified.
Dietary administration of Butylated hydroxyanisole to fish (hermaphroditic Rivulus marmoratus) as larvae caused liver cancer (hepatocellular carcinoma) in the adult fish.
Cancer Studies in Humans
The data available from epidemiological studies are inadequate to evaluate the relationship between human cancer and exposure specifically to Butylated hydroxyanisole.
Since Butylated hydroxyanisole was listed in the Sixth Annual Report on Carcinogens, one epidemiological study of Butylated hydroxyanisole has been identified.
A population-based nested case-control study of stomach cancer in men and women within the Netherlands Cohort Study of dietary intake found no increase in risk at typical levels of dietary intake of Butylated hydroxyanisole.
SYNONYMS
2-tert-Butyl-4-methoxyphenol
3-tert-butyl-4-methoxyphenol
2-tert-Butyl-4-hydroxyanisole
3-tert-butyl-4-hydroxyanisole
BOA
BHA
tert-Butyl-4-hydroxyanisole
(1,1-Dimethylethyl)-4-methoxyphenol
tert-Butyl-4-methoxyphenol
Antioxyne B
