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3(2)-tert-Butyl-4-hydroxyanisole

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? (1) ?? : ? ??? ??? 57～65℃??? ??.

??(2) ?? : ? ?? 0.5g? ??? 10mL? ?? ? ? ?? ?? ????? ??.

??(3) ??? : ? ?? 0.5g? ??? 35mL? ??? ???? 1mL ? ?? ??? 50mL? ?? ?????? ??. ?? 0.01N ?? 0.2mL? ??? 35mL, ???? 1mL ? ?? ??? 50mL? ?? ????? ??. ? ?? ?????? 2mL? ??? ? ?? 10?? ??? ?, ????? ??? ???? ?? ????? ??.

??(4) ?? : ? ??? ?????? ?? ??? ?, ? ?? 4.0ppm ????? ??.

??(5) ? : ? ?? 5.0g? ??? ??????? ?? ?????????????? ?? ??? ?, ? ?? 2.0ppm ????? ??.

??(6) ?? : ? ??? ?????? ?? ??? ?, ? ?? 1.0ppm ????? ??.

??(7) ????????? : ? ?? 1g? ????????? ??(1 : 1) 20mL? ??? ???. ?? ? 10mL ? ???????? 1mL? ??? ? ??? ?? ?? ???? ??? ???. ? ?? ????????? ??(1 : 1) 20mL? ??? ? ??? ?? ? ???? ??? ??? ?? ??? 500mL? ??. ? ? 1mL? ????? ?? ???????? 2mL, ????(3→100) 5mL ? ?? ??? 30mL? ??. ?? 4-?????????(1→1,000) 5mL? ??? ??? ?? ?? ?????????(1→100) 1mL? ?? ??? ?? ?? ?? ??? 50mL? ?? 15?? ?? ? ?, ? ?? ?? ????????????? 0.6mL? ?? ?? 50mL? ? ?? ??? ????? ?? ??.

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? (1) ? ??? ?????(1→100) 2～3mL? ????(1→50) 2～3?? ? 2, 6-????????????? ?? ??? ??? ??? ??? ?? ???? ????.

??(2) 「??????????」? ???? (2)? ?? ????.

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? ? ??? ?????? 0.05% ????? ??.

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Butylated hydroxyanisole (BHA) is an antioxidant widely used in food. Because it is contained in pastry, it can induce sensitization in caterers.

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Butylated hydroxyanisole occurs as a white or almost white crystalline powder or a yellowish-white waxy solid with a faint, characteristic aromatic odor.

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BHA is not known to occur as a natural product.

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Butylated 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.

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A mixture of 2- and 3-tert-4-methoxyphenol.

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Prepared by the reaction of p-methoxyphenol with isobutene.

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White, beige or slightly yellow waxy solid with an aromatic odor and a slightly bitter burning taste.

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Insoluble in water.

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Butylated 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.

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Toxic by ingestion. Use in foods restricted; consult FDA regulations.

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Butylated hydroxyanisole is combustible.

Pharmaceutical Applications

Butylated 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.

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BHA is an antioxidant widely used in cosmetics and food. Contained in pastry, it can induce sensitization in caterers.

Safety Profile

Confirmed 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

Safety

Butylated 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

Carcinogenicity

Butylated hydroxyanisole (BHA) is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.

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The metabolites of BHA can bind to cellular macromolecules, such as proteins and DNA, and cause toxicity.

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Exposure 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.

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UN2811 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

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Butylated 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.

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Suggested: Dispose of contents and container to an approved waste disposal plant. All federal, state, and local environmental regulations must be observed.

Regulatory Status

GRAS 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.

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