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フェニル酢酸エチル
フェニル酢酸エチル · エチルフェニルアセテート · 2-フェニル酢酸エチル · 酢酸フェネチル,フェニル酢酸エチル · エチル=フェニルアセタート · エチルフェニルアセタート · エチルα-トルイル酸 · ベンゼン酢酸エチル
識別子と物理属性
| CAS No. | 101-97-3 |
|---|---|
| 分子式 | C10H12O2 |
| 平均分子量 | 164.2 g/mol |
| 単同位体質量 | 164.08372962 g/mol |
| SMILES | CCOC(=O)Cc1ccccc1 |
| InChIKey | DULCUDSUACXJJC-UHFFFAOYSA-N |
| PubChem CID | 7590 |
| ChEMBL | CHEMBL3183476 |
| ChEBI | CHEBI:180411 |
| EC No. | 202-993-8 |
| DTXSID | DTXSID6044353 |
| 現地名 | フェニル酢酸エチル |
化学・物理的性質
| XLogP | 2.3 |
|---|---|
| 極性表面積 | 26.3 |
| 水素結合供与体数 | 0 |
| 水素結合受容体数 | 2 |
| 回転可能結合数 | 4 |
| 重原子数 | 12 |
| 形式電荷 | 0 |
| 複雑度 | 137 |
| 物質分類 | Other Classes -> Esters, Other |
| 化粧品 | TonicSolvent |
| SpringerMaterials Properties | Boiling point |
| 香料 | Fragrance Ingredient (Ethyl phenylacetate) -> IFRA transparency List |
| LogP（分配係数） | log Kow = 2.28 |
| 臭い | Sweet, honey odorPleasant odorジプロピレングリコール中10.00%。スイートフローラルハニーローズバルサムココア |
| 味 | Taste characteristics at 10 ppm: sweet, fruity, honey, cocoa, apple and woodyFloral, Fruit, Honey, Rose |
| 食品添加物 | FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food |
| 密度 | 1.0333 g/cu cm at 20 °C1.027-1.0321.03 g/mL at 25 °C(lit.) |
| 香味料 | EU Flavoring substances |
| Color/Form | LiquidColorless liquid |
| 溶解度 | In water, 1,478 mg/L at 25 °CSoluble in waterVery soluble in ethyl ether, ethanolSoluble in fixed oilsinsol in glycerin, propylene glycolSoluble in 8 parts of 60% alcoholInsoluble in water glyceryl, propylene glycolsoluble in oilsクロロホルム（微量）、酢酸エチル（微量）不溶性 |
| 融点 | -29 °C |
| 沸点 | 229 °C(lit.) |
| 蒸気圧 | 22.7Pa at 20℃ |
| FEMA | 2452 | ETHYL PHENYLACETATE |
| 屈折率 | n20/D 1.497(lit.) |
| 引火点 | 172 °F |
| 貯蔵条件 | Store below +30°C. |
| 色 | 無色 |
| においのタイプ | 花柄 |
| 由来生物 | synthetic |
| Merck | 14,3840 |
| JECFA Number | 1009 |
| BRN | 509140 |
| 誘電率 | 5.4(21℃) |
| 主な用途 | フレーバーそして香料 |
| 化粧品成分の機能 | 香料 |
| InChI | 1S/C10H12O2/c1-2-12-10(11)8-9-6-4-3-5-7-9/h3-7H,2,8H2,1H3 |
| InChIKey | DULCUDSUACXJJC-UHFFFAOYSA-N |
| SMILES | CCOC(=O)Cc1ccccc1 |
| LogP（分配係数） | 2.36 at 22℃ |
| CAS データベース | 101-97-3(CAS DataBase Reference) |
| NISTの化学物質情報 | Benzeneacetic acid, ethyl ester(101-97-3) |
| EPAの化学物質情報 | Benzeneacetic acid, ethyl ester (101-97-3) |
化学的特性
Ethyl Phenylacetate is a volatile aroma component of fruit and honey. It is a clear colourless to pale yellowish liquid with a pleasant, strong, sweet odor reminiscent of honey and a bittersweet flavor. Small amounts are used in flower perfumes and in fruit flavors.
安全性と法規制
| GHS 分類 | This chemical does not meet GHS hazard criteria for 99.8% (1778 of 1782) of all reports.Not ClassifiedAggregated GHS information provided per 1782 reports by companies from 4 notifications to the ECHA C&L Inventory. |
|---|---|
| 規制情報 | Chemical: Benzeneacetic acid, ethyl esterCommission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)Status: Active Update: 24-07-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/16453Benzeneacetic acid, ethyl ester: Non hazardous |
| その他の安全情報 | IMAP assessments - Benzeneacetic acid, ethyl ester: Human health tier I assessment |
| 火災の可能性 | Combustible liquid |
| 有害性の概要 | Safe when used as a flavoring agent in food[JECFA] May cause irritation[Sigma-Aldrich MSDS] See Phenylacetic acid. |
| FDA 要件 | Ethyl phenylacetate is a food additive permitted for direct addition to food for human consumption as a synthetic flavoring substance and adjuvant in accordance with the following conditions: a) they are used in the minimum quantity required to produce their intended effect, and otherwise in accordance with all the principles of good manufacturing practice, and b) they consist of one or more of the following, used alone or in combination with flavoring substances and adjuvants generally recognized as safe in food, prior-sanctioned for such use, or regulated by an appropriate section in this part. |
| NFPA Hazard Classification | 1 - Materials that, under emergency conditions, can cause significant irritation.1 - Materials that must be preheated before ignition can occur. Materials require considerable preheating, under all ambient temperature conditions, before ignition and combustion can occur.0 - Materials that in themselves are normally stable, even under fire conditions. |
| Hazard Classes and Categories | Not Classified |
| Skin, Eye, and Respiratory Irritations | In a human patch pretest the skin irritation potential of the test material was determined. No irritation was found.Four female albino rabbits were exposed to 0.1 mL of the test article in the left eye. ... Slight signs of irritation were observed on the treated eyes. All effects were fully reversible within 72 hours. Ethyl phenyl acetate shall not be classified as eye irritating. |
| Hazardous Reactivities and Incompatibilities | Incompatible materials: Strong oxidizing agents, Strong bases |
| Firefighting Hazards | Carbon oxides |
| 消火手順 | Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.Wear self contained breathing apparatus for fire fighting if necessary. |
| 保管条件 | Keep container tightly closed in a dry and well-ventilated place. Containers which are opened must be carefully resealed and kept upright to prevent leakage. |
| 清掃方法 | ACCIDENTAL RELEASE MEASURESPersonal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid breathing vapours, mist or gas. Do not let product enter drains. Soak up with inert absorbent material and dispose of as hazardous waste. Keep in suitable, closed containers for disposal. |
| 処分方法 | SRP: 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 air, soil or watereffects on animal, aquatic and plant lifeand conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.Product: Offer surplus and non-recyclable solutions to a licensed disposal company. Contaminated packaging: Dispose of as unused product. |
| Preventive Measures | ACCIDENTAL RELEASE MEASURESPersonal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid breathing vapours, mist or gas. Do not let product enter drains.Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. |
| Personal Protective Equipment (PPE) | Eye/face protection: Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).Skin protection: Handle with gloves.Body Protection: Impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.Respiratory protection: Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator with multipurpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU). |
| 体内負荷 | Ethyl phenyl acetate was detected in human expired air, collected from 28 healthy individuals, with concentrations ranging between approximately 0.3 to 1.05 ng/L of expired air, and a geometric mean of approximately 0.65 ng/L of expired air(1). Ethyl phenyl acetate was detected in human expired air, collected from 54 healthy individuals, with concentrations ranging between approximately 0.038 to 0.349 ng/L of expired air, and a geometric mean of approximately 0.115 ng/L of expired air(2). |
| 環境中動態 | TERRESTRIAL FATE: Based on a classification scheme(1), Koc values of 78, 110, and 129(2-4) indicate that ethyl phenylacetate is expected to have high mobility in soil(SRC). Volatilization of ethyl phenylacetate from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.88X10-5 atm-cu m/mole(SRC), using a fragment constant estimation method(5). Ethyl phenylacetate has an estimated vapor pressure of 6.24X10-2 mm Hg(SRC), determined from a fragment constant method(6) and exists as a liquid under environmental conditionstherefore, ethyl phenylacetate may volatilize from dry soil. Utilizing the Closed Bottle test, 78% degradation was reached in 28 days(7) indicating that biodegradation is an important environmental fate process in soil(SRC).AQUATIC FATE: Based on a classification scheme(1), Koc values of 78, 110, and 129(2-4) indicate that ethyl phenylacetate is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(5) based upon an estimated Henry's Law constant of 1.88X10-5 atm-cu m/mole(SRC), developed using a fragment constant estimation method(6). Using this Henry's Law constant and an estimation method(7), volatilization half-lives for a model river and model lake are 1.7 days and 23 days, respectively(SRC). According to a classification scheme(8), an estimated BCF of 15(SRC), from its log Kow of 2.28(9) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low. Utilizing the Closed Bottle test, 78% degradation was reached in 28 days(10) indicating that biodegradation is an important environmental fate process in water(SRC).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), ethyl phenylacetate, which has an estimated vapor pressure of 6.24X10-2 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase ethyl phenylacetate 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 6.2 days(SRC), calculated from its rate constant of 5.2X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Ethyl phenylacetate does not contain chromophores that absorb at wavelengths >290 nm(4) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC). |
| 食品調査値 | Ethyl phenylacetate was detected in 3 commercial samples of fermented soybean (Glycine max) curds obtained from a Hong Kong market, at concentrations of 191.2 ug/kg, 296.4 ug/kg, and 150.1 ug/kg(1). It is a constituent of cider, grape wines and port wine(2). |
| 毒性の概要 | IDENTIFICATION AND USE: Ethyl phenyl acetate is a colorless liquid and a flavor ingredient found in food and drinks such as juices and wines. HUMAN STUDIES: In a human patch pretest, no skin irritation was found. There were no instances of contact-sensitization in healthy male volunteers. It was negative in the in vitro study performed to assess the irritation potential in the Human Skin Model Test. ANIMAL STUDIES: Ethyl phenyl acetate was not irritating to the eyes of rabbits. It was not sensitizing in guinea pigs. In a mutagenesis study with the Salmonella strains TA92, TA1535, TA100, TA1537, TA94, TA98 and for some samples TA2637 with and without metabolic activation no mutagenic effects were observed. |
| Plant Concentrations | Ethyl phenylacetate is a volatile aroma component of fruit and honey(1). It is a constituent of grapefruit juice, apple juice, figs, guava, pineapple, and papaya(2).Ethyl phenylacetate occurrence in plants(1).[Table#8418] |
| Ongoing Test Status | EPA has released the Interactive Chemical Safety for Sustainability (iCSS) Dashboard. The iCSS Dashboard provides an interactive tool to explore rapid, automated (or in vitro high-throughput) chemical screening data generated by the Toxicity Forecaster (ToxCast) project and the federal Toxicity Testing in the 21st century (Tox21) collaboration. /The title compound was tested by ToxCast and/or Tox21 assays/[USEPAICSS Dashboard ApplicationAvailable from, as of May 1, 2017: http://actor.epa.gov/dashboard/] |
| Effluent Concentrations | Ethyl phenylacetate was detected in 2 samples of waste water collected from a rural New Jersey publicly owned treatment works facility, at a concentration of 3 ppbit was not detected in samples collected from two NJ POTWs located in industrial areas(1). |
| Soil Adsorption/Mobility | Experimental Koc values for ethyl phenylacetate have been reported to be 78(1), 110(2), and 129 (alfisol soil, 1.25% organic carbon, 69.7%sand, 14.4% silt, and 15.9% clay)(3). According to a classification scheme(4), these Koc values suggest that ethyl phenylacetate is expected to have high mobility in soil(SRC). |
| Natural Pollution Sources | Ethyl phenylacetate is a volatile aroma component of fruit and honey(1). Ethyl phenylacetate is a component of some tissues and essential oils of various plant species and plant parts(2). Ethyl phenyl acetate was detected in human expired air(3). |
| Human Toxicity Excerpts | /HUMAN EXPOSURE STUDIES/ In a pre-test for a human maximization study, a patch was applied under occlusion to normal sites on the backs of 5 subjects for 48 hours. No skin irritation effects were observed. On the basis of these results the substance was considered to be non irritating to the skin. Conclusions: In a human patch pretest the skin irritation potential of the test material was determined. No irritation was found./HUMAN EXPOSURE STUDIES/ A maximization test was conducted to determine the contact-sensitizing potential of the test item. 25 healthy male inmate volunteers were used in a maximization test. In the main test the test item was applied under occlusion to the same sites on the volar forearms of all subjects for five alternate-day 48 hour periods. The patch sites were pre-treated for 24 hours with 5 % aqueous sodium lauryl sulfate under occlusion. Following a ten day rest period, challenge patches of all materials were applied under occlusion to fresh sites for 48 hours. No instances of contact-sensitization from any material on the maximization test were found. Conclusions: There were no instances of contact-sensitization from any material on the maximization test. It is unlikely that these materials would present a danger of contact-sensitization in normal, intended use./ALTERNATIVE and IN VITRO TESTS/ This in vitro study was performed to assess the irritation potential of the test item by means of the Human Skin Model Test. The test item did not prove to be a MTT reducer (test for direct MTT reduction), and it did not change color when mixed with deionized water (test for color interference). Also its intrinsic color was not intensive. Consequently, additional tests with freeze-killed or viable tissues were not necessary. Each three tissues of the human skin model EpiDerm were treated with the test item, the negative or the positive control for 60 minutes. Each 30 uL of the test item, of the negative control (DPBS), and of the positive control (5% SLS) were applied to each tissue and spread to match the surface of the tissue. After treatment with the negative control the absorbance values were well in the required range of the acceptability criterion of mean OD = 0.8 and = 2.8 for the 60 minutes treatment interval, thus assuring the quality of the tissues. Treatment with the positive control induced a sufficient decrease in the relative absorbance as compared to the negative control for the 60 minutes treatment interval, and thus assuring the validity of the test system. After treatment with the test item the mean relative absorbance value decreased to 89.1% compared to the relative absorbance value of the negative control. This value is above the threshold for irritancy of = 50%. Therefore, the test item is not considered to possess an irritant potential. |
| Artificial Pollution Sources | Ethyl phenylacetate's production and use in food flavorings and as a chemical intermediate(1,2) may result in its release to the environment through various waste streams(SRC). Its use in perfumery(1) will result in its direct release to the environment(SRC). Ethyl phenylacetate has been detected in wastewater effluents from publicly-owned water treatment facilities(3). |
| Environmental Biodegradation | AEROBIC: Ethyl phenylacetate passed the 14-day window criteria and reached 78% degradation after 28 days using an activated sludge inoculum in the Closed Bottle Test EU Method C.4-E, and is therefore readily biodegradable(1). |
| 水環境危害等級（WGK） | 2 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | AJ2824000 |
| 毒性 | The acute oral LD50 value in rats was reported as 3.30g/kg(2.52-4.08 g/kg) (Moreno,1973).The acute dermal LD50 in rabbits was reported as > 5g/kg(Moreno, 1973). |
| 税関コード | 29163500 |
| 化審法 | (3)-1730 |
| 消防法 | 危-4-3-III |
| 安全措置（S） | 23-24/25 |
| 貯蔵分類 | 10 - Combustible liquids |
| 有害物質データ | 101-97-3(Hazardous Substances Data) |
用途
用途
有機合成原料。
天然物の起源
Reported found in grapefruit juice, apple juice, figs, guava, pineapple, papaya, cognac, cider, grape wines and port wine.
使用
Ethyl phenylacetate was used to study the solvent-based self-healing of epoxy materials. It is also used as a flavoring agent, flavor animal feeds, In perfumery.
一般的な説明
Ethyl phenylacetate is a less toxic, greener solvent. It is non-mutagenic.
製法・合成法
製造方法
Ethyl phenylacetate is prepared by heating at the boil phenylacetonitrile and sulfuric acid in alcohol solution; by esterification of the acid catalyzed by HCl or H2SO4.
純化方法
Shake the ester with saturated aqueous Na2CO3 (three times), aqueous 50% CaCl2 (twice) and saturated aqueous NaCl (twice). Dry with CaCl2 and distil it under reduced pressure. [Beilstein 9 H 434, 9 IV 1618.]