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| 融点 | 69-73 °C(lit.) | | 沸点 | 265 °C(lit.) | | 比重(密度) | 1.048 | | 蒸気密度 | 7.6 (vs air) | | 蒸気圧 | <0.01 mm Hg ( 20 °C) | | 屈折率 | 1.4859 | | FEMA | 2184 | BUTYLATED HYDROXYTOLUENE | | 闪点 | 127 °C | | 貯蔵温度 | 2-8°C | | 溶解性 | methanol: 0.1 g/mL, clear, colorless | | 外見 | Crystals | | 酸解離定数(Pka) | pKa 14(H2O
t = 25
c = 0.002 to 0.01) (Uncertain) | | 色 | white | | 臭い (Odor) | faint characteristic odor | | においのタイプ | phenolic | | 水溶解度 | insoluble | | Merck | 14,1548 | | BRN | 1911640 | | 暴露限界値 | ACGIH: TWA 2 mg/m3
NIOSH: TWA 10 mg/m3 | | 安定性： | Stable, but light-sensitive. Incompatible with acid chlorides, acid anhydrides, brass, copper, copper alloys, steel, bases, oxidizing agents. Combustible. | | InChIKey | NLZUEZXRPGMBCV-UHFFFAOYSA-N | | LogP | 5.2 | | CAS データベース | 128-37-0(CAS DataBase Reference) | | IARC | 3 (Vol. 40, Sup 7) 1987 | | NISTの化学物質情報 | Butylated hydroxytoluene(128-37-0) | | EPAの化学物質情報 | 2,6-Di-tert-butyl-p-cresol (128-37-0) |
| | ブチルヒドロキシトルエン Usage And Synthesis |
| 外観 | 白色〜わずかにうすい黄色, 結晶又は粒状 | | 定義 | BHTは、ジブチルヒドロキシトルエンの表示名称である。本品は、次の化学式で表されるトルエン誘導体である。 | | 溶解性 | エタノール及びアセトンに溶け、水にほとんど溶けない。 | | 解説 | C15H24O(220.36)．2,6-ジ-t-ブチル-4-メチルフェノールは，略称BHT．p-クレゾールに2-メチルプロペンを硫酸存在下に反応させると得られる．融点71 ℃，沸点265 ℃．d420"1.048．nD75"1.4895．水，アルカリに不溶，有機溶媒に可溶．食品，石油製品の酸化防止剤，香料，化粧品の添加剤，各種プラスチックの可塑剤に用いられる．食品衛生法により食品への使用が認められている．LD50 1700～1970 mg/kg(ラット，経口)．森北出版「化学辞典（第2版） | | 用途 | ゴム老化防止剤、酸化防止剤。 | | 用途 | 有機ゴム薬品、老化防止剤、芳香族系有機薬品、食品添加物、酸化防止剤、香料中間体、化粧品原料 | | 用途 | ジブチルヒドロキシトルエン定量用標準品。 | | 化粧品の成分用途 | 酸化防止剤、香料 | | 効能 | 酸化防止剤 | | 主な用途／役割 | ゴム系樹脂成分の接着剤の老化防止剤、ホットメルト系接着剤の酸化防止剤として使用される。 | | 説明 | The antioxidant butylated hydroxytoluene is contained
in food, adhesive glues, industrial oils and greases, including cutting fluids. Sensitization seems
very rare. | | 説明 | Butylated Hydroxytoluene is a synthetic antioxidant. It scavenges peroxide, 2,2-diphenyl-1-picrylhydrazyl (DPPH; ), superoxide, and ABTS radicals in cell-free assays, as well as inhibits lipid peroxidation of linoleic acid (Item Nos. 90150 | 90150.1 | 21909) in vitro when used at a concentration of 45 μg/ml. Butylated Hydroxytoluene (0.025-3.2 mM) reduces freeze-thaw-induced malondialdehyde (MDA) production and increases sperm viability in boar spermatozoa preparations. Formulations containing BHT have been used as antioxidant cosmetic and food additives. | | 化学的特性 | BHA 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. Butylated Hydroxytoluene has a very faint, musty, occasional cresylictype
odor. BHA and Butylated Hydroxytoluene are extensively used in foods as antioxidants. Most fats, oils and fat-containing foods are naturally susceptible
to rapid rancification and other oxidative reactions that produce compounds having objectionable taste and odor, making foods containing
them unpalatable. Lipid oxidation is autocatalytic and proceeds as a complex of chain reactions, the nature and speed of which vary with
the substrate, temperature, light, availability of oxygen and presence or absence of oxidation catalysts. Antioxidants like BHT act as “chain
breaks” in the autooxidation processes under the usual conditions of processing, storage and use of fat-containing foods (Burdock, 1997). | | 化学的特性 | Butylated hydroxytoluene occurs as a white or pale yellow crystalline solid or powder with a faint characteristic phenolic odor. | | 化学的特性 | white crystalline solid | | 化学的特性 | Butylated Hydroxytoluene is a white to pale yellow crystalline solid
or powder. | | 天然物の起源 | Not reported found naturally. | | 使用 | Because they prevent rancidity, antioxidants are of great interest to the food industry. For example, butylated hydroxytoluene (BHT), butylated hydroxyanisole (BHA), and EDTA are frequently used to preserve various foods, such as cheese or fried products. Butylated hydroxytoluene is a powerful inhibitor of lipid peroxidation, yet large doses of it can induce oxidative DNA damage and cancer development in the rat forestomach. | | 使用 | Antioxidant 264 as general antioxidants is used widely in polymer materials, petroleum products and food processing industries. Antioxidant 264 is commonly used rubber antioxidant, heat, oxygen aging have some protective effect, but also can inhibit copper harm. This product does not change color, not pollution. Antioxidants 264 high solubility in oil, no precipitation, less volatile, non-toxic and non-corrosive. | | 使用 | Butylated Hydroxytoluene (BHT) is an antioxidant that functions similarly to butylated hydroxyanisole (BHA) but is less stable at high temperatures. It is also termed 2,6-di-tert-butyl-para-cresol. See Butylated Hydroxyanisole. | | 使用 | Butylated Hydroxytoluene is also known as butylated hydroxy toluene. It is an anti-oxidant that also has preservative and masking capabilities. | | 使用 | Antioxidant for food, animal feed, petroleum products, synthetic rubbers, plastics, animal and vegetable oils, soaps. Antiskinning agent in paints and inks. | | 製造方法 | Butylated Hydroxytoluene is produced commercially by the alkylation of para-cresol with isobutylene. Butylated Hydroxytoluene is also produced by several western
European manufacturers, production/processing plants in Germany, France, the Netherlands, United Kingdom and Spain. | | 定義 | ChEBI: A member of the class of phenols that is 4-methylphenol substituted by tert-butyl groups at positions 2 and 6. | | 調製方法 | Prepared by the reaction of p-cresol with isobutene. | | 一般的な説明 | White crystalline solid. | | 空気と水の反応 | Insoluble in water. | | 反応プロフィール | Phenols, such as 2,6-Di-tert-butyl-4-methylphenol, do not behave as organic alcohols, as one might guess from the presence of a hydroxyl (-OH) group in their structure. Instead, they react as weak organic acids. Phenols and cresols are much weaker as acids than common carboxylic acids (phenol has Ka = 1.3 x 10^[-10]). These materials are incompatible with strong reducing substances such as hydrides, nitrides, alkali metals, and sulfides. Flammable gas (H2) is often generated, and the heat of the reaction may ignite the gas. Heat is also generated by the acid-base reaction between phenols and bases. Such heating may initiate polymerization of the organic compound. Phenols are sulfonated very readily (for example, by concentrated sulfuric acid at room temperature). The reactions generate heat. Phenols are also nitrated very rapidly, even by dilute nitric acid. Nitrated phenols often explode when heated. Many of them form metal salts that tend toward detonation by rather mild shock. May react with oxidizing materials. | | 健康ハザード | 2,6-Di-tert-butyl-p-cresol or Butylated Hydroxytoluene is of relatively low acute toxicity in
animals, and there is no evidence of either
acute or chronic effects among exposed
workers. | | 火災危険 | 2,6-Di-tert-butyl-4-methylphenol is combustible. | | 燃焼性と爆発性 | Non flammable | | 応用例（製薬） | Butylated hydroxytoluene is used as an antioxidant in
cosmetics, foods, and pharmaceuticals. It is mainly used to
delay or prevent the oxidative rancidity of fats and oils and to
prevent loss of activity of oil-soluble vitamins.
Butylated hydroxytoluene is also used at 0.5–1.0% w/w
concentration in natural or synthetic rubber to provide enhanced
color stability.
Butylated hydroxytoluene has some antiviral activity and has
been used therapeutically to treat herpes simplex labialis. | | 接触アレルゲン | This antioxidant is contained in food, adhesive glues,
industrial oils, and greases, including cutting fluids.
Sensitization seems very rare. | | Biochem/physiol Actions | Butylated hydroxytoluene is a phenolic antioxidant. It has been shown to inhibit lipid peroxidation. It causes lung injury and promotes tumors in mice, but this may be due to a metabolite of Butylated Hydroxytoluene, 6-tert-butyl-2-[2′-(2′-hydroxymethyl)-propyl]-4-methylphenol. Metabolites of Butylated Hydroxytoluene have also been reported to induce DNA strand breaks and internucleosomal DNA fragmentation (a characteristic of apoptosis) in cultured cells. In rats, a single intraperitoneal injection of Butylated Hydroxytoluene (60 mg/kg body mass) results in a significant increase in nuclear DNA methyl transferase activity in the liver, kidneys, heart, spleen, brain and lungs. Incubation of alveolar macrophages with Butylated Hydroxytoluene significantly reduced the level of TNF-α which may explain the mechanism by which this antioxidant reduces inflammation. Preincubation of aspirin-treated platelets with Butylated Hydroxytoluene inhibits the secretion, aggregation, and protein phosphorylation induced by protein kinase C activators. Butylated Hydroxytoluene was also found to inhibit the initiation of hepatocarcinogenesis by aflatoxin B1. | | 応急処置 | If this chemical gets into the eyes, remove anycontact lenses at once and irrigate immediately for at least15 min, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts theskin, remove contaminated clothing and wash immediatelywith soap and water. Seek medical attention immediately. Ifthis chemical has been inhaled, remove from exposure,begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR ifheart action has stopped. Transfer promptly to a medicalfacility. When this chemical has been swallowed, get medical attention. Give large quantities of water and inducevomiting. Do not make an unconscious person vomit. | | 発がん性 | The IARC has determined that there is limited evidence for the carcinogenicity of Butylated Hydroxytoluene in experimental animals.Butylated Hydroxytoluene has given primarily negative results in a large number of in vivo and in vitro genotoxic assays.No significant reproductive effects were observed in three-generation toxicity studies in mice administered up to 0.4% in the diet.6 The 2003 ACGIH threshold limit valuetime- weighted average (TLV-TWA) for 2,6-ditert- butyl-p-cresol is 2mg/m3. | | 環境運命予測 | The metabolites of Butylated Hydroxytoluene can bind to cellular macromolecules,
such as proteins and DNA, and cause toxicity. | | 職業ばく露 | DBPC is used as a food and feed additive, flavor, and packaging material; as an antioxidant in human foods and animal feeds. It is also used as an antioxidant to sta- bilize petroleum fuels, rubber and vinyl plastics. | | 安全性プロファイル | Poison by intraperitoneal andintravenous routes. Moderately toxic by ingestion. Anexperimental teratogen. Other experimental reproductiveeffects. A human skin irritant. A skin and eye irritant.Questionable carcinogen with experimental carcinogenicand. | | 安全性 | Butylated hydroxytoluene is readily absorbed from the gastrointestinal tract and is metabolized and excreted in the urine mainly as glucuronide conjugates of oxidation products. Although there have been some isolated reports of adverse skin reactions, butylated hydroxytoluene is generally regarded as nonirritant and nonsensitizing at the levels employed as an antioxidant.
The WHO has set a temporary estimated acceptable daily intake for butylated hydroxytoluene at up to 125 μg/kg body-weight.
Ingestion of 4 g of butylated hydroxytoluene, although causing severe nausea and vomiting, has been reported to be nonfatal.
LD50 (guinea pig, oral): 10.7 g/kg
LD50 (mouse, IP): 0.14 g/kg
LD50 (mouse, IV): 0.18 g/kg
LD50 (mouse, oral): 0.65 g/kg
LD50 (rat, oral): 0.89 g/kg | | 貯蔵 | Exposure to light, moisture, and heat causes discoloration and a loss of activity. Butylated hydroxytoluene should be stored in a wellclosed container, protected from light, in a cool, dry place. | | 輸送方法 | UN2811 Toxic solids, organic, n.o.s., Hazard
Class: 6.1; Labels: 6.1-Poisonous materials, Technical
Name Required. | | 純化方法 | Dissolve Butylated Hydroxytoluene in n-hexane at room temperature, then cool with rapid stirring, to -60o. The precipitate is separated, redissolved in hexane, and the process is repeated until the mother liquor is no longer coloured. The final product is stored under N2 at 0o [Blanchard J Am Chem Soc 82 2014 1960]. It has also been recrystallised from EtOH, MeOH, *benzene, n-hexane, methylcyclohexane or pet ether (b 60-80o), and is dried in a vacuum. [Beilstein 6 IV 3511.] | | Toxicity evaluation | Butylated Hydroxytoluene is a white crystalline solid. It is insoluble in water and
alkalies; but soluble in most common organic solvents such
as alcohol and ether. Its melting point is 70°C, boiling point
is 265°C, flash point is 127°C, and specific gravity is 1.048
at 20°C. | | 不和合性 | Butylated hydroxytoluene is phenolic and undergoes reactions
characteristic of phenols. It is incompatible with strong oxidizing
agents such as peroxides and permanganates. Contact with
oxidizing agents may cause spontaneous combustion. Iron salts
cause discoloration with loss of activity. Heating with catalytic
amounts of acids causes rapid decomposition with the release of the
flammable gas isobutene. | | 不和合性 | Contact with oxidizers may cause fire
and explosion hazard. | | 規制状況(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, rectal, topical, and vaginal
preparations). Included in nonparenteral medicines licensed in the
UK. Included in the Canadian List of Acceptable Non-medicinal
Ingredients. |
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