基本情報
- 標準SMILES
Cc1cc(Cc2cc(C)cc(C(C)(C)C)c2O)c(O)c(C(C)(C)C)c1- InChIKey
KGRVJHAUYBGFFP-UHFFFAOYSA-N- 分子式
- C23H32O2
- 平均分子量
- 340.5 g/mol
- 単同位体質量
- 340.24023026
名称と識別子
- 優先名称
- 2,2'-Methylenebis(4-methyl-6-tert-butylphenol)
- IUPAC
- 2-tert-butyl-6-[(3-tert-butyl-2-hydroxy-5-methylphenyl)methyl]-4-methylphenol
- 現地名
- 2,2'-メチレンビス(6-tert-ブチル-p-クレゾール)
- 英語名
- 2,2'-Methylenebis(4-methyl-6-tert-butylphenol)
- 分子式
- C23H32O2
- 分子量
- 340.5
名称と別名
名称をさらに表示
データベース識別子
- CAS
119-47-1- PubChem CID
- 8398
- DTXSID
DTXSID4020870- ChEMBL
CHEMBL460648- ChEBI
CHEBI:172336- UNII
- KVM0X4X57B
- EC Number
- 204-327-1
- Nikkaji
- J36.831H
物性
構造計算による物性
- XLogP
- 7.2
- 極性表面積
- 40.5 Ų
- 水素結合供与体数
- 2
- 水素結合受容体数
- 2
- 回転可能結合数
- 4
- 重原子数
- 25
- 形式電荷
- 0
- 複雑度
- 390
実験および物理化学的性質
Solubility
Soluble in oxygen and aromatic solvents.
Water solubility = 0.02 mg/l.
Physical Description
Liquid; Dry Powder; Other Solid; Dry Powder
Off-white solid; [HSDB]
Kovats Retention Index
2398
2365.3
物理化学的性質
- 融点
- 123 · 123-127 °C(lit.)
- 沸点
- 187 ℃ · 187℃
- 比重(密度)
- 1.04 g/cm3 · 1.04g/cm3
- 蒸気圧
- 1 hPa · <1 hPa
- 屈折率
- 1.448 · 1.4480 (estimate)
- 闪点
- 195 °C · 195°C(383°F)
- 貯蔵温度
- 30 °C · Store below +30°C.
- 溶解性
- 0.007 mg/l · 0.007mg/l 実質的に不溶
- 外見
- 白からオフホワイトの固体。
- 酸解離定数(Pka)
- 11.32 · 11.32±0.48(Predicted)
- 色
- ホワイトからオフホワイト
- PH
- 4 · 4-7 (H2O, 20℃)(aqueous suspension)
- 水溶解度
- 7 μg/L · 7μg/L at 20℃
- Henry's Law Constant
- 1.2 · 1.2×106 mol/(m3Pa) at 25℃, HSDB (2015)
- 化粧品成分の機能
- 抗酸化物質
- InChI
- 1S/C23H32O2/c1-14-9-16(20(24)18(11-14)22(3,4)5)13-17-10-15(2)12-19(21(17)25)23(6,7)8/h9-12,24-25H,13H2,1-8H3
- InChIKey
- KGRVJHAUYBGFFP-UHFFFAOYSA-N
- SMILES
- Cc1cc(Cc2cc(C)cc(c2O)C(C)(C)C)c(O)c(c1)C(C)(C)C
- LogP
- 6.25 at · 6.25 at 20℃
- CAS データベース
- 119 · 119-47-1(CAS DataBase Reference)
- NISTの化学物質情報
- 2 · Phenol, 2,2'-methylenebis[6-(1,1-dimethylethyl)-4-methyl-(119-47-1)
- EPAの化学物質情報
- 2 · 2,2'-Methylenebis(6-tert-butyl-p-cresol) (119-47-1)
安全と法規制
GHS分類
GHS Classification
Danger
H360F: May damage fertility [Danger Reproductive toxicity]
P203, P280, P318, P405, and P501 (click each P-code to see the statement)
This chemical does not meet GHS hazard criteria for 15.4% (153 of 995) of reports.
危険有害性情報
Regulatory Information
Chemical: Phenol, 2,2â²-methylenebis[6-(1,1-dimethylethyl)-4-methyl-
Hazard Traits - Reproductive Toxicity;Authoritative List - EC Annex VI CMRs - Cat. 1B;Report - if used as a fragrance or flavor ingredient
Phenol, 2,2'-methylenebis[6-(1,1-dimethylethyl)-4-methyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Phenol, 2,2'-methylenebis[6-(1,1-dimethylethyl)-4-methyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
Status: Active Update: 10-10-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/13380
Substance: 6,6'-di-tert-butyl-2,2'-methylenedi-p-cresol;EC: 204-327-1;Date of inclusion: >17-Jan-2022;Reason for inclusion: Toxic for reproduction (Article 57c)
Methylene bis methyl butyl phenol: Does not have an individual approval but may be used under an appropriate group standard
Hazards Summary
Chronic high dose oral studies with rodents caused functional changes in the nervous system and liver and morphological changes to testes; [HSDB] A moderate eye irritant, based on animal studies; Although acute oral LD50 is more than 5,000 mg/kg, male reproductive effects were observed in sperm and histopathological changes to testes in test groups of 42.3 mg/kg and higher (NOAEL male reproductive toxicity = 12.2 mg/kg/day); [eChemPortal: SIDSUNEP] An eye irritant; [MSDSonline]
Hazard Classes and Categories
Repr. 1B (25.2%);Repr. 2 (46.2%);Aquatic Chronic 4 (47.4%)
Reproductive toxicity - category 1B
Reproductive toxicity - Category 1B;Specific target organ toxicity - Repeated exposure - Category 2 (reproductive organs (male));Hazardous to the aquatic environment (Long-term) - Category 4
Repr. 1B
安全と保護具
Disposal Methods
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
毒性情報
Interactions
WHEN ADDED TO THE DIET FOR 4 MONTHS BEFORE TOPICAL APPLICATION OF BENZO[A]PYRENE & THEN UNTIL DEVELOPMENT OF MALIGNANCY BY THE INDUCED PAPILLOMAS, EXTRACTS FROM POLYETHYENE OR POLYPROPYLENE PRODUCTS, CONTAINING LOW AMOUNTS OF BIS(2-HYDROXY-3-TERT-BUTYL-5- METHYLPHENYL)METHANE, HAD AN INHIBITORY EFFECT ON THE CARCINOGENIC PROCESS.
Environmental Fate
TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 59800(SRC), determined from an experimental log Kow(2) and a recommended regression-derived equation(3), indicates that bis(2-hydroxy-3-tert-butyl-5-methylphenyl)methane will have no mobility in soil(SRC). Volatilization of bis(2-hydroxy-3-tert-butyl-5-methylphenyl)methane may not be important from moist soil surfaces(SRC) given an estimated Henry's Law constant of 7.9X10-12 atm-cu m/mole(4,SRC), or from dry soil surfaces(SRC) based on an estimated vapor pressure of 2.5X10-9 mm Hg(5,SRC). Based on a MITI biodegradation test, bis(2-hydroxy-3-tert-butyl-5-methylphenyl)methane will not biodegrade in soil(2).
AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 59800(SRC), determined from an experimental log Kow(2) and a recommended regression-derived equation(3), indicates that bis(2-hydroxy-3-tert-butyl-5-methylphenyl)methane will adsorb to suspended solids and sediment(SRC) in the water. Bis(2-hydroxy-3-tert-butyl-5-methylphenyl)methane should not volatilize from water surfaces based on an estimated Henry's Law constant of 7.9X10-12 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Experimental BCF values of 23-37 and 60-125 at 1 and 0.1 mg/L(2), suggest that bis(2-hydroxy-3-tert-butyl-5-methylphenyl)methane will bioconcentrate in aquatic organisms(SRC) according to a recommended classification scheme(5). Based on a MITI biodegradation test, bis(2-hydroxy-3-tert-butyl-5-methylphenyl)methane will not biodegrade in water(2).
ATMOSPHERIC FATE: According to a suggested classification scheme(1), an estimated vapor pressure of 2.5X10-9 mm Hg at 25 °C(2,SRC) indicates that bis(2-hydroxy-3-tert-butyl-5-methylphenyl)methane will exist in the particulate phase in the ambient atmosphere. Particulate-phase bis(2-hydroxy-3-tert-butyl-5-methylphenyl)methane may be physically removed from the air by wet and dry deposition(SRC).
Adverse Effects
Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.;Reproductive Toxin - A chemical that is toxic to the reproductive system, including defects in the progeny and injury to male or female reproductive function. Reproductive toxicity includes developmental effects. See Guidelines for Reproductive Toxicity Risk Assessment.
Soil Adsorption/Mobility
The Koc of bis(2-hydroxy-3-tert-butyl-5-methylphenyl)methane is estimated as approximately 59800(SRC), using an experimental log Kow of 6.25(1) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this estimated Koc value suggests that bis(2-hydroxy-3-tert-butyl-5-methylphenyl)methane will be immobile in soil and strongly adsorbed to suspended solids and sediment in water(SRC).
TSCA Test Submissions
2,2'-Bis(6-t-butyl-p-cresyl)methane (CAS # 119-47-1) was evaluated for dermal sensitization in humans. The test substance (25% concentration) was applied to the back of 25 adult males for a course of five (5) 48-hour exposures with 1-day rest periods. The test substance was applied to the same site which had been previously irritated by treatment with 5% sodium lauryl sulfate for 1-day. Two weeks after the last exposure, a challenge patch test of .5 g (10% concentration) of test substance was applied at a naive site under an occlusive dressing. The test substance was not irritating or allergic.
Artificial Pollution Sources
Bis(2-hydroxy-3-tert-butyl-5-methylphenyl)methane's production and use as a stabilizer used in styrenic and olefin polymers and polyoxymethylene homo and copolymers(1), and as an antioxidant(2) may result in its release to the environment through various waste streams(SRC).
Environmental Bioconcentration
An estimated BCF value of 33100 was calculated for bis(2-hydroxy-3-tert-butyl-5-methylphenyl)methane(SRC), using an experimental log Kow of 6.25(1) and a recommended regression-derived equation(2). Bioconcentration factors of 23-37 and 60-125 were obtained during an 8 week bioconcentration study using carp and bis(2-hydroxy-3-tert-butyl-5-methylphenyl)methane concentrations of 1 and 0.1 mg/l, respectively(1). According to a recommended classification scheme(3), the experimental BCF values suggest that bioconcentration in aquatic organisms will be moderate to high(SRC).
Volatilization from Water/Soil
The Henry's Law constant for bis(2-hydroxy-3-tert-butyl-5-methylphenyl)methane is estimated as 7.9X10-12 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This value indicates that bis(2-hydroxy-3-tert-butyl-5-methylphenyl)methane will be essentially nonvolatile from water surfaces(2,SRC). Bis(2-hydroxy-3-tert-butyl-5-methylphenyl)methane's vapor pressure, 2.5X10-9 mm Hg(3,SRC) and Henry's Law constant(1,SRC) indicate that volatilization from dry and moist soil should not occur(SRC).
Non-Human Toxicity Excerpts
BIS(2-HYDROXY-3-TERT- BUTYL-5-METHYLPHENYL)METHANE PRODUCED LITTLE CHANGE IN LIVER LIPIDS IN MALE RATS GIVEN 1.135 MMOL% FOR 1 WK.
THE ACUTE, ORAL LD50 VALUES OF BISALKOFEN BP IN RATS AND MICE WERE 5000 & 11000 MG/KG, RESPECTIVELY. IN CHRONIC EXPERIMENTS, BISALKOFEN BP (50 MG/KG/DAY, FOR 10 MONTHS) INDUCED FUNCTIONAL CHANGES IN THE NERVOUS SYSTEM & LIVER, & MORPHOLOGICAL CHANGES IN THE TESTES. SMALLER CHRONIC DOSES OR SHORTER TREATMENT (4 MONTHS) WERE WITHOUT EFFECTS.
法規制情報
Regulatory Information
Chemical: Phenol, 2,2â²-methylenebis[6-(1,1-dimethylethyl)-4-methyl-
Hazard Traits - Reproductive Toxicity;Authoritative List - EC Annex VI CMRs - Cat. 1B;Report - if used as a fragrance or flavor ingredient
Phenol, 2,2'-methylenebis[6-(1,1-dimethylethyl)-4-methyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Phenol, 2,2'-methylenebis[6-(1,1-dimethylethyl)-4-methyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
Status: Active Update: 10-10-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/13380
Substance: 6,6'-di-tert-butyl-2,2'-methylenedi-p-cresol;EC: 204-327-1;Date of inclusion: >17-Jan-2022;Reason for inclusion: Toxic for reproduction (Article 57c)
Methylene bis methyl butyl phenol: Does not have an individual approval but may be used under an appropriate group standard
安全データ
- wgk
- 1
- tsca
- TSCA listed
- rtecs
- PA3500000
- 毒性
- LD50 orally in Rabbit: 4880 mg/kg LD50 dermal Rabbit > 2000 mg/kg
- hs_code
- 29072900
- risk_code
- 36-62-53
- 化審法
- (4)-100
- hazard_code
- Xi,Xn
- safety_code
- 26-36-60-36/37
- 自然発火温度
- 350 °C
- Hazard Classifications
- Repr. 1B
- ストレージクラス
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- 有毒物質データの
- 119-47-1(Hazardous Substances Data)
化学と産業
用途と製造
Uses
Used as an antioxidant and stabilizer for polymers (ABS, polypropylene, polyacetal, rubber, latex, and adhesives); [HSDB]
Plastic Composites Manufacturing [Category: Industry]
Stabilizer used in styrenic and olefin polymers and polyoxymethylene homo and copolymers.
Antioxidant (ABS, polypropylene, polyacetal, rubber, latex, adhesives).
Plastics -> Typical concentration range in plastic materials -> 0.5%
Use Classification
Fragrance Ingredients
Plastics -> Antioxidants
Plastics -> Polymer Type -> Polyolefin-I; ABS
Cosmetics -> Antioxidant
General Manufacturing Information
All Other Basic Organic Chemical Manufacturing;Wood Product Manufacturing;Machinery Manufacturing;Not Known or Reasonably Ascertainable;Adhesive Manufacturing;Fabricated Metal Product Manufacturing;Plastics Material and Resin Manufacturing;Computer and Electronic Product Manufacturing;Electrical Equipment, Appliance, and Component Manufacturing;Transportation Equipment Manufacturing;Synthetic Rubber Manufacturing;Rubber Product Manufacturing
Phenol, 2,2'-methylenebis[6-(1,1-dimethylethyl)-4-methyl-: ACTIVE
応用分野
用途酸化防止剤。
使用LOWINOX® 22M46 stabilizer is a non-discoloring antioxidant based on a sterically hindered alkylated bis-phenol.
一般的な説明2,2′-Methylenebis(6-tert-butyl-4-methylphenol) is a phenolic antioxidant commonly used in increasing the oxidation stability in rubber and plastic industries.
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