ChemicalBook > Product Catalog > Chemical Reagents > Organic reagents > Phenols > Butylated hydroxyanisole
Butylated hydroxyanisole Chemical Properties
- Melting point:58-60 °C(lit.)
- Boiling point:264-270°C
- Density 0.9976 (rough estimate)
- vapor density 6.2 (vs air)
- refractive index 1.4910 (estimate)
- FEMA 2183 | BUTYLATED HYDROXYANISOLE
- Flash point:>230 °F
- storage temp. 2-8°C
- solubility Practically insoluble in water; soluble in methanol; freely soluble in ≥50% aqueous ethanol, propylene glycol, chloroform, ether, hexane, cottonseed oil, peanut oil, soybean oil, glyceryl monooleate, and lard, and in solutions of alkali hydroxides.
- form Crystalline Flakes or Crystals
- color White to pale yellow
- Water Solubility <0.1 g/100 mL at 18.5 ºC
- Merck 14,1547
- Stability:Stable, combustible. Incompatible with oxidizing agents, ferric salts. Degrades on long exposure to sunlight.
- IARC2B (Vol. 40, Sup 7) 1987
- EPA Substance Registry SystemButylated hydroxyanisole (25013-16-5)
- Hazard Codes Xn
- Risk Statements 22-40-36/37/38-51/53
- Safety Statements 36/37-36/37/39-26-61-29
- RIDADR 2811
- WGK Germany 2
- RTECS SL1945000
- Autoignition Temperature599 °F
- TSCA Yes
- HS Code 29093090
- Hazardous Substances Data25013-16-5(Hazardous Substances Data)
- ToxicityLD50 in mice, rats (mg/kg): 2000, 2200 orally (Lehman)
Butylated hydroxyanisole Usage And Synthesis
- DescriptionButylated hydroxyanisole (BHA) is an antioxidant widely used in food. Because it is contained in pastry, it can induce sensitization in caterers.
- Chemical PropertiesBHA and BHT (butylated hydroxytoluene) are monohydric phenolic antioxidants that, prior to their introduction and acceptance in the food industry, were used to protect petroleum against oxidative degumming. Chemically, BHA is a mixture of two isomers, 3-tertiary-butyl-4-hydroxyanisole (90%) and 2-tertiary-butyl-4-hydroxyanisole (10%). Both BHA and BHT assert a good carry-through effect, although BHA is slightly better than BHT in this respect. BHT is, however, more effective in suppressing oxidation of animal fats than vegetable oils. Among its multiple applications, BHA is particularly useful in protecting the flavors and color of essential oils and is considered the most effective of all food-approved antioxidants for this application. BHA is particularly effective in controlling the oxidation of short-chain fatty acids, such as those found in coconut and palm kernel oils that are used typically in cereal and confectionary products.
- Chemical Propertieswhite or light yellow waxy solid with an
- Chemical PropertiesLog Kow 5. 3. Values above 3.0 are likely to bioaccumulate in aquatic organisms
- Chemical PropertiesButylated hydroxyanisole occurs as a white or almost white crystalline powder or a yellowish-white waxy solid with a faint, characteristic aromatic odor.
- OccurrenceBHA is not known to occur as a natural product.
- UsesBHA (butylated hydroxy anisole) is a preservative with anti-oxidant capabilities, not to be confused with beta hydroxy acids (BHAs).
- UsesButylated Hydroxyanisole (BHA) is an antioxidant that imparts stability to fats and oils and should be added before oxidation has started. It is a mixture of 3-tert-butyl-4-hydroxyanisole and 2-tertbutyl-4-hydroxyanisole. In direct addition, the fat or oil is heated to 60–70°C and the BHA is added slowly under vigorous agitation. The maximum concentration is 0.02% based on the weight of the fat or oil. It may protect the fat-soluble vitamins A, D, and E. It is used singly or in combination with other antioxidants. It is used in cereals, edible fat, vegetable oil, confectionary products, and rice.
- UsesButylated Hydroxyanisole is an antioxidant consisting of a mixture of two isomers of tert-butyl-4-hydroxyanisole. Butylated Hydroxyanisole is used in food preservation as it antioxidant properties pre vent food from becoming rancid. Butylated Hydroxyanisoleas is also used in animal feed, petroleum products, and cosmetics.
- UsesAntioxidant and preservative, especially in foods, cosmetics, pharmaceuticals; also rubber and petroleum products.
- DefinitionA mixture of 2- and 3-tert-4-methoxyphenol.
- Production MethodsPrepared by the reaction of p-methoxyphenol with isobutene.
- Aroma threshold valuesDetection: 3 ppm
- General DescriptionWhite, beige or slightly yellow waxy solid with an aromatic odor and a slightly bitter burning taste.
- Air & Water ReactionsInsoluble in water.
- Reactivity ProfileButylated hydroxyanisole degrades with prolonged exposure to sunlight. Exhibits antioxidant properties and synergism with acids, BHT, propyl gallate, hydroquinone, methionine, lecithin and thiodipropionic acid. Butylated hydroxyanisole exhibits antioxidant properties as a scavenger of free radicals. Butylated hydroxyanisole is incompatible with oxidizing agents and ferric salts.
- HazardToxic by ingestion. Use in foods restricted; consult FDA regulations.
- Fire HazardButylated hydroxyanisole is combustible.
- Pharmaceutical ApplicationsButylated hydroxyanisole is an antioxidant with some
antimicrobial properties. It is used in a wide range of cosmetics,
foods, and pharmaceuticals. When used in foods, it is used to delay
or prevent oxidative rancidity of fats and oils and to prevent loss of
activity of oil-soluble vitamins.
Butylated hydroxyanisole is frequently used in combination with other antioxidants, particularly butylated hydroxytoluene and alkyl gallates, and with sequestrants or synergists such as citric acid.
FDA regulations direct that the total content of antioxidant in vegetable oils and direct food additives shall not exceed 0.02% w/w (200 ppm) of fat or oil content or essential (volatile) oil content of food.
USDA regulations require that the total content of antioxidant shall not exceed 0.01% w/w (100 ppm) of any one antioxidant or 0.02% w/w combined total of any antioxidant combination in animal fats.
Japanese regulations allow up to 1 g/kg in animal fats.
- Contact allergensBHA is an antioxidant widely used in cosmetics and food. Contained in pastry, it can induce sensitization in caterers.
- Safety ProfileConfirmed carcinogen with experimental carcinogenic, neoplastigenic, and tumorigenic data. Moderately toxic by ingestion and intraperitoneal routes. Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits acrid and irritating fumes
- SafetyButylated hydroxyanisole is absorbed from the gastrointestinal tract
and is metabolized and excreted in the urine with less than 1%
unchanged within 24 hours of ingestion. Although there have
been some isolated reports of adverse skin reactions to butylated
hydroxyanisole, it is generally regarded as nonirritant and
nonsensitizing at the levels employed as an antioxidant.
Concern over the use of butylated hydroxyanisole has occurred following long-term animal feeding studies. Although previous studies in rats and mice fed butylated hydroxyanisole at several hundred times the US-permitted level in the human diet showed no adverse effects, a study in which rats, hamsters, and mice were fed butylated hydroxyanisole at 1–2% of the diet produced benign and malignant tumors of the forestomach, but in no other sites. However, humans do not have any region of the stomach comparable to the rodent forestomach and studies in animals that also do not have a comparable organ (dogs, monkeys, and guinea pigs) showed no adverse effects. Thus, the weight of evidence does not support any relevance to the human diet where butylated hydroxyanisole is ingested at much lower levels. The WHO acceptable daily intake of butylated hydroxyanisole has been set at 500 μg/kg body-weight.
LD50 (mouse, oral): 1.1–2.0 g/kg
LD50 (rabbit, oral): 2.1 g/kg
LD50 (rat, IP): 0.88 g/kg
LD50 (rat, oral): 2.0 g/kg
- Chemical SynthesisSeveral methods are used for the commercial production of BHA. Methylation of hydroquinone yields an intermediate that gives a mixture of 3-BHA and 2-BHA upon treatment with tert-butyl alcohol and phosphoric acid. Butylation of hydroquinone and subsequent methylation with dimethyl sulfate and sodium hydroxide can also be used to produce a mixture of the two BHA isomers. In addition BHA can be synthesized by the tert-butylation of 4-methoxyphenol over silica or alumina at 150°C.
- CarcinogenicityButylated hydroxyanisole (BHA) is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.
- storageExposure to light causes discoloration and loss of activity. Butylated hydroxyanisole should be stored in a well-closed container, protected from light, in a cool, dry place.
- ShippingUN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1—Poisonous materials, Technical Name Required. UN3077 Environmentally hazardous substances, solid, n.o.s., Hazard class: 9; Labels: 9— Miscellaneous hazardous material, Technical Name Required
- IncompatibilitiesButylated hydroxyanisole is phenolic and undergoes reactions characteristic of phenols. It is incompatible with oxidizing agents and ferric salts. Trace quantities of metals and exposure to light cause discoloration and loss of activity.
- Waste DisposalSuggested: Dispose of contents and container to an approved waste disposal plant. All federal, state, and local environmental regulations must be observed.
- Regulatory StatusGRAS listed. Accepted as a food additive in Europe. Included in the FDA Inactive Ingredients Database (IM and IV injections, nasal sprays, oral capsules and tablets, and sublingual, rectal, topical, and vaginal preparations). Included in nonparenteral medicines licensed in the UK. Included in the Canadian List of Acceptable Nonmedicinal Ingredients.
Butylated hydroxyanisole Preparation Products And Raw materials
- TERT-BUTYL VINYL ETHER tert-Butyldimethylsilyl chloride Trifluoromethanesulfonic acid tert-butyldimethylsilyl ester tert-Butylchlorodiphenylsilane Tosylmethyl isocyanide 1,1,3,3-TETRAMETHYLBUTYL ISOCYANIDE COBALT ETHYLENE DIAMINE CHLORIDE tert-Butanol Butyldiglycol Triclosan 2-Butoxyethanol 4-Methoxyphenol Butylated hydroxyanisole 4-Methylanisole Butyl acetate Guaiacol Anisole Cyhalofop-butyl
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