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4-Methylbenzaldehyde
p-トルアルデヒド · 4-メチルベンゼンカルボアルデヒド · 1-メチル-4-ホルミルベンゼン · 4-メチルベンズアルデヒド · 1-ホルミル-4-メチルベンゼン · トリルアルデヒド · p-メチルベンズアルデヒド · p-トルイルアルデヒド
識別子と物理属性
| CAS No. | 104-87-0 |
|---|---|
| 分子式 | C8H8O |
| 平均分子量 | 120.15 g/mol |
| 単同位体質量 | 120.05751488 g/mol |
| SMILES | Cc1ccc(C=O)cc1 |
| InChIKey | FXLOVSHXALFLKQ-UHFFFAOYSA-N |
| PubChem CID | 7725 |
| ChEMBL | CHEMBL190927 |
| ChEBI | CHEBI:28617 |
| EC No. | 203-246-9 |
| DTXSID | DTXSID9041520 |
| 現地名 | p-トルアルデヒド |
化学・物理的性質
| XLogP | 2.1 |
|---|---|
| 極性表面積 | 17.1 |
| 水素結合供与体数 | 0 |
| 水素結合受容体数 | 1 |
| 回転可能結合数 | 1 |
| 重原子数 | 9 |
| 形式電荷 | 0 |
| 複雑度 | 90.7 |
| 物質分類 | Other Classes -> Benzaldehydes |
| SpringerMaterials Properties | 13C nuclear magnetic resonance spectrum |
| 香料 | Fragrance Ingredient (p-Tolualdehyde) -> IFRA transparency List |
| 臭い | Floral odorジプロピレングリコール中5.00%。フルーティーチェリーディープフェノール |
| 密度 | 1.0194 g/cu cm at 17 °C1.019 g/mL at 25 °C (lit.) |
| 香味料 | EU Flavoring substances |
| Color/Form | COLORLESS LIQUID |
| 溶解度 | Miscible with ethanol, ethyl ether, acetonevery soluble in chloroformIn water, 2.27X10+3 mg/L at 25 °C2.27 mg/mL at 25 °C水: 可溶0.25 g/L at 25°C0.25g/L（25℃） |
| 沸点 | 204 °CBP: 106 °C at 10 mm Hg204.00 °C. @ 760.00 mm Hg204-205 °C (lit.) 82-85 °C/11 mmHg (lit.) |
| Decomposition | When heated to decomposition it emits acrid smoke and irritating vapors. |
| 融点 | -6 °C |
| 蒸気圧 | 0.25 [mmHg]2.5X10-1 mm Hg at 25 °C0.33 hPa (25 °C) |
| FEMA | 3068 | TOLUALDEHYDES (MIXED O,M,P) |
| 屈折率 | n20/D 1.545(lit.) |
| 引火点 | 176 °F |
| 貯蔵条件 | Store below +30°C. |
| 外観・状態 | 液体 |
| 色 | 無色透明～黄色 |
| においのタイプ | フルーティーな |
| 由来生物 | synthetic |
| 爆発限界 | 0.9-5.6%(V) |
| BRN | 385772 |
| ヘンリー定数 | 5.3×10-1 mol/(m3Pa) at 25℃, Brockbank (2013) |
| 化粧品成分の機能 | 香料 |
| InChI | 1S/C8H8O/c1-7-2-4-8(6-9)5-3-7/h2-6H,1H3 |
| InChIKey | FXLOVSHXALFLKQ-UHFFFAOYSA-N |
| SMILES | [H]C(=O)c1ccc(C)cc1 |
| LogP（分配係数） | 2.25 |
| CAS データベース | 104-87-0(CAS DataBase Reference) |
| NISTの化学物質情報 | Benzaldehyde, 4-methyl-(104-87-0) |
| EPAの化学物質情報 | 4-Methylbenzaldehyde (104-87-0) |
化学的特性
Clear colorless to pale yellow liquid. Soluble in alcohol and oils. Sweet-herbaceous, Bitter-almond-like moderately tenacious odor. Not as pungent as Benzaldehyde, but more herbaceous-warm. Intensely sweet, warm-fruity and Bitteralmond-like taste in concentrations lower than 500 ppm.
安全性と法規制
| GHS 分類 | WarningH302 (99.8%): Harmful if swallowed [Warning Acute toxicity, oral]P264, P264+P265, P270, P280, P301+P317, P305+P351+P338, P330, P337+P317, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 1818 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.H227: Combustible liquid [Warning Flammable liquids] |
|---|---|
| 規制情報 | Chemical: Benzaldehyde, 4-methyl-Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)Benzaldehyde, 4-methyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzaldehyde, 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: 30-01-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/220544-Methylbenzaldehyde: Does not have an individual approval but may be used under an appropriate group standard |
| 有害性の概要 | A skin, eye, and respiratory tract irritantDilute solutions of tolualdehydes did not induce skin sensitization in volunteers[HSDB] An irritant[MSDSonline] |
| TSCA 要件 | Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329. Effective date 9/30/91Reporting date: 11/27/91.Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Benzaldehyde, 4-methyl- is included on this list. Effective date 9/30/91Sunset date: 6/30/98. |
| Hazard Classes and Categories | Acute Tox. 4 (99.8%)Flammable liquids - Category 4 |
| Skin, Eye, and Respiratory Irritations | The low molecular weight aldehydes, the halogenated aliphatic aldehydes, and the unsaturated aldehydes are particularly irritating. /Aldehydes/ |
| 処分方法 | SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air qualitypotential migration in soil or watereffects on animal, aquatic, and plant lifeand conformance with environmental and public health regulations. |
| Preventive Measures | SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place. |
| 体内負荷 | p-Methylbenzaldehyde was detected in expired air at an average concentration of 6.5 ng/L from 28 human subjects(1). 5.6% of expired air samples from 54 human subjects contained 4-methylbenzaldehyde at a mean concentration of 3.3 ng/L(2). |
| 生態毒性値 | EC50Species: Tetrahymena pyriformis (Ciliate, GL-C strain)Conditions: freshwater, staticConcentration: 134510 ug/L for 48 hr (95% confidence limit: 95820-164650 ug/L)Effect: decreased population growth |
| 環境中動態 | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 62(SRC), determined from a water solubility of 2,270 mg/L(2) and a regression-derived equation(3), indicates that 4-methylbenzaldehyde is expected to have high mobility in soil(SRC). Volatilization of 4-methylbenzaldehyde from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.7X10-5 atm-cu m/mole(SRC), derived from its vapor pressure, 0.25 mm Hg(4), and its water solubility(2). 4-Methylbenzaldehyde is expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). Based on limited information, 4-methylbenzaldehyde is expected to biodegrade in soil(SRC). A Pseudomonas strain was able to utilize 4-methylbenzaldehyde as the sole carbon source(5)a yeast strain grown with both this compound and either sucrose or pyruvate biodegraded 4-methylbenzaldehyde to the respective aromatic carbinol or alcohol(6).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 62(SRC), determined from a water solubility of 2,270 mg/L(2) and a regression-derived equation(3), indicates that 4-methylbenzaldehyde is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 1.7X10-5 atm-cu m/mole(SRC), derived from its vapor pressure, 0.25 mm Hg(4), and its water solubility(2). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 2.4 and 21 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 8(SRC), from its water solubility(2) and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Based on limited data, biodegradation of 4-methylbenzaldehyde will take place in water(SRC). A Pseudomonas strain was able to utilize 4-methylbenzaldehyde as the sole carbon source(6)a yeast strain grown with both this compound and either sucrose or pyruvate biodegraded 4-methylbenzaldehyde to the respective aromatic carbinol or alcohol(7).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 4-methylbenzaldehyde, which has a vapor pressure of 0.25 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 4-methylbenzaldehyde is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC)the half-life for this reaction in air is estimated to be 21 hrs(SRC), calculated from its rate constant of 1.8X10-11 cu cm/molecule-sec at 25 °C(3). The reactivity of 4-methylbenzaldehyde (1 ppm) with NOx (0.5 ppm) in light was measured in a smog chamber as 1.78 ppb/min(4). 4-Methylbenzaldehyde contains chromophores that absorb at wavelengths >290 nm(5) and therefore may be susceptible to direct photolysis by sunlight(SRC). |
| 食品調査値 | 4-Methylbenzaldehyde is a constituent of coffee aroma(1), roasted filberts(2), roasted earth almonds (Cyperus esculentus L.)(3). 4-Methylbenzaldehyde was detected in a Spanish type paprika oleoresin at 1.3 mg/kg(4). |
| Plant Concentrations | 4-Methylbenzaldehyde was detected in raw earth almonds (Cyperus esculentus L.)(1). |
| Effluent Concentrations | Operation of a four-stroke outboard motor resulted in the exhaust emission of 2.8 mg/10 min of 4-methylbenzaldehyde into the water(1). 4-Methylbenzaldehyde was emitted from a fireplace burning jack pine, cedar, red oak, and green ash wood at concns of 0.114-0.475 g/kg(2). 4-Methylbenzaldehyde was emitted from non-catalyst and catalyst automobiles at 7.7 and 1.7 ug/km, respectively(3). Heavy-duty diesel trucks emitted 2.3 ug 4-methylbenzaldehyde/km(3). 4-Methylbenzaldehyde was identified in rush hour traffic air samples taken at the Oakland-San Francisco Bay Bridge toll plaza 4/23/2001, 5-7 pm, 4/24/2001, 6-10 am, and 3-7 pm at concns of 0.018-0.023 ug/cu m(4). 4-Methylbenzaldehyde was found in highway tunnels in Tuscaroralight duty trucks emitted 0.023 mg/km traveled or 0.305 mg/L fuel used, heavy duty trucks emitted 0.335 mg/km traveled or 0.962 mg/L fuel used(5). 4-Methylbenzaldehyde emissions from an automobile running on Swedish environmental classified diesel fuel were 0.6 mg/km and the same automobile running on European program emissions fuel were also 0.6 mg/km(6).3-Methylbenzaldehyde/4-methylbenzaldehyde was measured in the emissions of burnt wood at 12 and 27 mg/kg of pine and eucalyptus, but was not detected in the emissions of burnt oak(1). |
| Soil Adsorption/Mobility | The Koc of 4-methylbenzaldehyde is estimated as 62(SRC), using a water solubility of 2,270 mg/L(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 4-methylbenzaldehyde is expected to have high mobility in soil. |
| TSCA Test Submissions | P-Tolualdehyde (CAS # 104-87-0) was evaluated for acute oral toxicity. The test substance was administered to 10 rats (sex and strain not indicated) at a dosage range of 200-3200 mg/kg. No unusual clinical signs were observed, except for evidence of slight toxicity. Mortality data were not provided, except for time of death (within 1 day). The LD50 was determined to be 1600 mg/kg.P-Tolualdehyde (CAS # 104-87-0) was evaluated for acute inhalation toxicity by exposing 6 rats (sex and strain not indicated) to a single six-hour inhalation exposure of 373 and 444 ppm. No mortality occurred. The rats gained weight normally and there were no unusual clinical signs other than irritation.P-Tolualdehyde (CAS # 104-87-0) was evaluated for subchronic oral toxicity. The test substance was administered by gavage to 5/rats/dose (sex and strain not indicated) at dosage levels of 100 or 1000 mg/kg/day for a total of 12 doses over 17 days. Feed consumption and weight gain were normal. Hematology, clinical chemistry, liver and kidney weights, and gross and histopathological findings were normal.P-Tolualdehyde (CAS # 104-87-0) was evaluated for subchronic dermal toxicity. The test substance was administered (dosage not indicated) to the clipped backs of guinea pigs (number, sex, and strain not indicated) and repeated applications produced a slight exacerbation of the irritation response seen from a single application.For more TSCA Test Submissions (Complete) data for 4-METHYLBENZALDEHYDE (8 total), please visit the HSDB record page. |
| Natural Pollution Sources | 4-Methylbenzaldehyde was detected in raw earth almonds (Cyperus esculentus L.)(1). |
| Atmospheric Concentrations | URBAN/SUBURBAN: 4-Methylbenzaldehyde, analyzed in Athens, Greece, June to December 2000, was detected at Patission Street at concns of 1.2-5.9 ug/cu m(1). 4-Methylbenzaldehyde was detected at average concns of 0.032-0.131 ug/cu m in Rio de Janeiro, Brazil Oct 1999 to Nov 2000(2). 4-Methylbenzaldehyde was analyzed but not detected in samples taken at the top of an 11 story building on the campus of Hong Kong University Science and Technology(3).RURAL/REMOTE: 4-Methylbenzaldehyde was identified in forest air collected in the Southern Black Forest, Germany, at unreported concentrations(1).SOURCE DOMINATED: 4-Methylbenzaldehyde was analyzed but not detected in kitchen exhaust(1). |
| Human Toxicity Excerpts | /SIGNS AND SYMPTOMS/ The mucus membranes of the nasal and oral passages and the upper respiratory tract are affected, producing a burning sensation, ... bronchial constriction, choking, and coughing. The eyes tear, and a burning sensation is noted on the skin of the face. /Aldehydes//SIGNS AND SYMPTOMS/ No evidence of skin sensitization was found in volunteers treated with dilute solutions. /Tolualdehydes/ |
| Artificial Pollution Sources | 4-Methylbenzaldehyde's production and use in perfumes, as a pharmaceutical and dyestuff intermediate, and as a flavoring agent(1) may result in its release to the environment through various waste streams(SRC). Exhaust from outboard motors(2), automobiles and trucks(3), and emissions from fireplaces(4) contain 4-methylbenzaldehyde. |
| F | 9-23 |
| 水環境危害等級（WGK） | 1 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | CU7034500 |
| 輸送番号（UN） | NA 1993 / PGIII |
| 毒性 | LD50 orally in Rabbit: 1600 mg/kg |
| 税関コード | 29122900 |
| 危険文句（R） | 22-36/37/38-36/38 |
| 化審法 | (3)-2659 |
| 消防法 | 危-4-3-III |
| 危険表示 | Xn |
| 安全措置（S） | 26-36-37/39 |
| 自然発火温度 | 395 °C DIN 51794 |
| 危険等級 | Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2 |
| 貯蔵分類 | 10 - Combustible liquids |
| 有害物質データ | 104-87-0(Hazardous Substances Data) |
用途
用途
香水、医薬品、染料中間体、香味剤
使用
p-Tolualdehyde is made by the Vilsmeier reaction employing toluene and dimethylformamide or the Guttermann–Koch reaction employing toluene and carbon monoxide.
一般的な説明
p-Tolualdehyde (4-Methylbenzaldehyde) is an aromatic aldehyde. It has been generated as major oxygenated product during the UV light irradiated oxygenation of p-xylene, via photoinduced electron transfer mechanism. It undergoes condensation reaction with diiron μ-ethylidyne complex to afford μ-vinylcarbyne complex (92% yield).
製法・合成法
純化方法
Steam distil the aldehyde, dry it with CaSO4, then fractionally distil it. [Beilstein 7 IV 672.]