25013-16-5 Usage
Uses
Used in Food Industry:
Butylated hydroxyanisole is used as an antioxidant and preservative for preventing food from becoming rancid. It imparts stability to fats and oils and should be added before oxidation has started. It may protect the fat-soluble vitamins A, D, and E and is used singly or in combination with other antioxidants. BHA is particularly effective in controlling the oxidation of short-chain fatty acids, such as those found in coconut and palm kernel oils used in cereal and confectionary products.
Used in Cosmetics Industry:
Butylated hydroxyanisole is used as an antioxidant and preservative in cosmetics, providing stability and preventing rancidity.
Used in Pharmaceutical Industry:
BHA serves as an antioxidant and preservative in the pharmaceutical industry, ensuring the stability and shelf life of various products.
Used in Animal Feed Industry:
Butylated hydroxyanisole is used in animal feed as an antioxidant to prevent rancidity and maintain the quality of the feed.
Used in Petroleum Products:
BHA is used as an antioxidant in petroleum products to protect against oxidative degumming.
Used in Rubber Industry:
Butylated hydroxyanisole is employed as an antioxidant in the rubber industry to prevent the oxidation and degradation of rubber materials.
Chemical Properties:
BHA is a white or light yellow waxy solid with an aromatic odor. It has a Log Kow value of 5.3, indicating a high potential for bioaccumulation in aquatic organisms. The detection threshold for BHA is 3 ppm.
Production Methods
Prepared by the reaction of p-methoxyphenol with isobutene.
Air & Water Reactions
Insoluble in water.
Reactivity Profile
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.
Hazard
Toxic by ingestion. Use in foods restricted;
consult FDA regulations.
Fire Hazard
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.
Contact allergens
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
Synthesis
Several 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.
Carcinogenicity
Butylated hydroxyanisole (BHA) is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.
Environmental Fate
The metabolites of BHA can bind to cellular macromolecules,
such as proteins and DNA, and cause toxicity.
storage
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.
Shipping
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
Toxicity evaluation
BHA is a white or slightly yellow, waxy solid with a characteristic
odor. It is insoluble in water, but soluble in fats, oils,
and solvents like petroleum ether, chloroform, and alcohol.
Its octanol/water partition coefficient is 3.50; vapor pressure is
2.48×10-3 mm Hg at 25°C; and Henry’s law constant is
1.17×10-6 atm-m3 mol-1.
BHA is released into the environment through waste
streams. It has low soil mobility and volatilizes slowly from
water. It may bioconcentrate in aquatic organisms, adsorb to
sediment, and be subject to direct photolysis.
Incompatibilities
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.
Waste Disposal
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.
Check Digit Verification of cas no
The CAS Registry Mumber 25013-16-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,5,0,1 and 3 respectively; the second part has 2 digits, 1 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 25013-16:
(7*2)+(6*5)+(5*0)+(4*1)+(3*3)+(2*1)+(1*6)=65
65 % 10 = 5
So 25013-16-5 is a valid CAS Registry Number.
InChI:InChI=1/C11H16O2/c1-3-4-6-9-7-5-8-10(13-2)11(9)12/h5,7-8,12H,3-4,6H2,1-2H3
