HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Methylphenylacetat
Methyl 2-phenylacetate · Methylphenylacetat · PHENYLACETIC ACID METHYL ESTER · Methyl benzeneacetate · FEMA 2733 · 2-phenylpropanoate · Mephaneine · METHYL A-TOLUATE
Identifikatoren & physikalische Daten
| CAS No. | 101-41-7 |
|---|---|
| Summenformel | C9H10O2 |
| Durchschnittliche Molmasse | 150,17 g/mol |
| Monoisotopische Masse | 150,06807956 g/mol |
| SMILES | COC(=O)Cc1ccccc1 |
| InChIKey | CRZQGDNQQAALAY-UHFFFAOYSA-N |
| PubChem CID | 7559 |
| ChEMBL | CHEMBL3189123 |
| ChEBI | CHEBI:167404 |
| EC No. | 202-940-9 |
| DTXSID | DTXSID1044352 |
| Lokaler Name | Methylphenylacetat |
Chemische & physikalische Eigenschaften
| XLogP | 1,8 |
|---|---|
| Polarare Oberfläche (TPSA) | 26,3 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 3 |
| Schwere Atome | 11 |
| Formalladung | 0 |
| Komplexität | 126 |
| Stoffklassen | Other Classes -> Esters, Other |
| SpringerMaterials Properties | Diamagnetic susceptibility |
| Duftstoffe | Fragrance Ingredient (Methyl phenylacetate) -> IFRA transparency List |
| LogP (Verteilungskoeffizient) | log Kow = 1.821.83 |
| Geruch | Honey, jasmine odor |
| Geschmack | Honey, JasmineTaste threshold: Taste characteristics at 30 ppm: Floral, honey, spice, waxy and sweet |
| Lebensmittelzusatzstoffe | FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food |
| Dichte | 1.062 g/mL1.061-1.0671.066 g/mL at 20 °C (lit.) |
| Aromastoffe | EU Flavoring substances |
| Color/Form | Colorless liquid |
| Löslichkeit | Soluble in most organic solvents1:6 in 60% alcoholinsoluble in water, glycerin and propylene glycol.Insoluble in water, glyceryl, propylene glycolsoluble in oils1 mL in 6 mL 60% ethanol (in ethanol)Chloroform (Slightly), Methanol (Slightly)Miscible with water. |
| Siedepunkt | 215 °C215.00 to 217.00 °C. @ 760.00 mm Hg218 °C (lit.) |
| Schmelzpunkt | 107-115 °C |
| Dampfdruck | 16.9-75Pa at 20℃ |
| FEMA | 2733 | METHYL PHENYLACETATE |
| Brechungsindex | n20/D 1.503(lit.) |
| Flammpunkt | 195 °F |
| Lagerbedingungen | Store below +30°C. |
| Farbe | Colourless |
| Wichte | 1.07 |
| Geruch | at 10.00 % in dipropylene glycol. sweet floral honey spice waxy almond |
| Geruchsart | honey |
| Biologische Quelle | synthetic |
| Merck | 14,7268 |
| JECFA Number | 1008 |
| BRN | 878795 |
| Stabilität | Stable. Combustible. Incompatible with strong oxidizing agents, strong bases. |
| InChI | 1S/C9H10O2/c1-11-9(10)7-8-5-3-2-4-6-8/h2-6H,7H2,1H3 |
| InChIKey | CRZQGDNQQAALAY-UHFFFAOYSA-N |
| SMILES | COC(=O)Cc1ccccc1 |
| LogP (Verteilungskoeffizient) | 1.91-2.09 at 21.9-25℃ |
| CAS Datenbank | 101-41-7(CAS DataBase Reference) |
| NIST chemische Informationen | Benzeneacetic acid, methyl ester(101-41-7) |
| EPA chemische Informationen | Methyl phenylacetate (101-41-7) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 99.8% (1661 of 1664) of all reports.Not ClassifiedAggregated GHS information provided per 1664 reports by companies from 3 notifications to the ECHA C&L Inventory.WarningH227: Combustible liquid [Warning Flammable liquids]P210, P280, P370+P378, P403, and P501 (click each P-code to see the statement) |
|---|---|
| Regulatorische Informationen | Chemical: Benzeneacetic acid, methyl esterCommission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)Status: Active Update: 03-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/16699Benzeneacetic acid, methyl ester: Does not have an individual approval but may be used under an appropriate group standard |
| Weitere Sicherheitsinformationen | IMAP assessments - Benzeneacetic acid, methyl ester: Human health tier I assessment |
| Brandpotenzial | Combustible liquid. |
| Gefahrenübersicht | A mild skin irritant[RTECS] Safe when used as a flavoring agent in food[JECFA] May cause irritation[Alfa Aesar MSDS] See Phenylacetic acid. |
| FDA-Anforderungen | Methyl 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. |
| Other Hazardous Reactions | Conditions to avoid: Heat, flames and sparks. |
| Hazard Classes and Categories | Not Classified |
| Skin, Eye, and Respiratory Irritations | A skin irritant. |
| Hazardous Reactivities and Incompatibilities | Incompatible materials: Strong oxidizing agents, Strong bases |
| Firefighting Hazards | Carbon oxides |
| Brandbekämpfungsverfahren | Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.Wear self-contained breathing apparatus for firefighting if necessary. Use water spray to cool unopened containers. |
| Lagerbedingungen | Keep container tightly closed in a dry and well-ventilated place. Storage class (TRGS 510): Combustible liquids |
| Reinigungsverfahren | ACCIDENTAL RELEASE MEASURES Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Remove all sources of ignition. Beware of vapors accumulating to form explosive concentrations. Vapors can accumulate in low areas. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Contain spillage, and then collect with an electrically protected vacuum cleaner or by wet-brushing and place in container for disposal according to local regulations. Keep in suitable, closed containers for disposal. |
| Entsorgungsverfahren | 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: This combustible material may be burned in a chemical incinerator equipped with an afterburner and scrubber. Offer surplus and non-recyclable solutions to a licensed disposal company. Contaminated packaging: Dispose of as unused product. |
| Preventive Measures | ACCIDENTAL RELEASE MEASURES Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Remove all sources of ignition. Beware of vapors accumulating to form explosive concentrations. Vapors can accumulate in low areas. Prevent further leakage or spillage if safe to do so. Do not let product enter drains.Avoid inhalation of vapor or mist. Keep away from sources of ignition - No smoking. Take measures to prevent the build up of electrostatic charge.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.SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits 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. |
| Personal Protective Equipment (PPE) | Eye/face protection: Safety glasses with side-shields conforming to EN166. 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). |
| Umweltverhalten | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 74(SRC), determined from a log Kow of 1.83(2) and a regression-derived equation(3), indicates that methyl phenylacetate is expected to have high mobility in soil(SRC). Volatilization of methyl phenylacetate from moist soil surfaces may be an important fate process(SRC) given an estimated Henry's Law constant of 1.4X10-5 atm-cu m/mole(SRC), using a fragment constant estimation method(4). Methyl phenylacetate has a vapor pressure of 0.13 mm Hg(5) and exists as a liquid at environmental standard temperature and pressuretherefore, methyl phenylacetate may volatilize from dry soil(SRC). Utilizing the Closed Bottle test, 75% degradation was reached in 28 days(5) indicating that biodegradation is an important environmental fate process in soil(SRC).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 74(SRC), determined from a log Kow of 1.83(2) and a regression-derived equation(3), indicates that methyl phenylacetate is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(4) based upon an estimated Henry's Law constant of 1.4X10-5 atm-cu m/mole(SRC), developed using a fragment constant estimation method(5). Using this Henry's Law constant and an estimation method(4), volatilization half-lives for a model river and model lake are 2 and 28 days, respectively(SRC). According to a classification scheme(6), an estimated BCF of 7.5(SRC), from its log Kow(2) and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Utilizing the Closed Bottle test, 75% degradation was reached in 28 days(7) 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), methyl phenylacetate, which has a vapor pressure of 0.13 mm Hg at 20 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase methyl 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 8.6 days(SRC), calculated from its rate constant of 3.7X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Methyl phenylacetate does not absorb UV light at wavelengths >290 nm(4) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC). |
| Lebensmitteluntersuchungswerte | Methyl phenylacetate is a constituent of cognac and Bourbon vanilla(1). |
| Toxizitätsübersicht | IDENTIFICATION AND USE: Methyl phenyl acetate is used as food and beverage ingredient. It is also the starting material in manufacture of synthetic perfumes. HUMAN STUDIES: There are no data available. ANIMAL STUDIES: Restrained bees were tested with methyl phenylacetate previously identified from Mycobacterium tuberculosis cultures, to determine honeybee capacity for signature volatile detection. Methyl phenylacetate was detectable over eight orders of magnitude. Potential exists for trained honeybees in non-invasive diagnostic tests for TB. |
| Plant Concentrations | Fresh flowers from honeysuckle plants (Lonicera japonica) contained methyl phenylacetate at 42 ug/kghoneysuckle flowers which had been open for 12 and 24 hours prior to collection contained methyl phenylacetate at 74 and 146 ug/kg, respectively(1). Methyl phenylacetate was identified as a volatile compound of potato foliage and tubers of S. tuberosum L. cv. Princess (Solanaceae)(2).Methyl phenylacetate occurrence in plants(1).[Table#8421] |
| 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/] |
| Soil Adsorption/Mobility | The Koc of methyl phenylacetate is estimated as 74(SRC), using a log Kow of 1.83(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that methyl phenylacetate is expected to have high mobility in soil. |
| Natural Pollution Sources | Methyl phenylacetate is a component of some tissues and essential oils of various plants(1). Methyl phenylacetate was identified as a volatile component of Mycobacterium tuberculosis and Mycobacterium bovis cultures grown in vitro(2). |
| Artificial Pollution Sources | Methyl phenylacetate's production and use as a synthetic food flavoring agent(1) may result in its release to the environment through various waste streams(SRC). Its use in the manufacture of synthetic perfumes(2) may result in its direct release to the environment(SRC). |
| Environmental Biodegradation | AEROBIC: Methyl phenylacetate passed the 10-day window criteria and reached 75% degradation after 28 days using an activated sludge inoculum in the Closed Bottle Test OECD 301D, and is therefore readily biodegradable(1). |
| Environmental Bioconcentration | An estimated BCF of 7.5 was calculated in fish for methyl phenylacetate(SRC), using a log Kow of 1.83(1) and a regression-derived equation(2). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC). |
| Volatilization from Water/Soil | The Henry's Law constant for methyl phenylacetate is estimated as 1.4X10-5 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that methyl phenylacetate is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(3) is estimated as 2 days(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(3) is estimated as 28 days(SRC). Methyl phenylacetate's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). Methyl phenylacetate has a vapor pressure of 0.13 mm Hg(4) and exists as a liquid at environmental standard temperature and pressuretherefore, methyl phenylacetate may volatilize from dry soil(SRC). |
| Non-Human Toxicity Excerpts | /OTHER TOXICITY INFORMATION/ The proboscis extension reflex in honeybees was evaluated for detection of tuberculosis. Restrained bees were tested with methyl phenylacetate, methyl p-anisate, and methyl nicotinate, previously identified from Mycobacterium tuberculosis cultures, to determine honeybee capacity for signature volatile detection. Methyl p-anisate and methyl phenylacetate were detectable over eight orders of magnitude, and honeybees showed proboscis extension response down to 0.1 pg loading of methyl p-anisate on filter paper. Potential exists for trained honeybees in non-invasive diagnostic tests for TB. |
| Wassergefährdungsklasse (WGK) | 2 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29163500 |
| RTECS-Nr. | AJ3175000 |
| R-Sätze (R) | 21-R21 |
| Toxizität | The acute oral LD50 in rats was reported as 2.55 g/kg (1.67-3.43 g/kg) and the acute dermal LD50 in rabbits as 2.4 g/kg (0.15-4.7 g/kg) (Moreno, 1974). |
| Gefahrensymbole | Xn |
| Sicherheitshinweise (S) | 23-24/25 |
| Lagerklasse | 10 - Combustible liquids |
| Gefahrstoffdaten | 101-41-7(Hazardous Substances Data) |
Anwendungen & Verwendung
Occurrence
Reported found in cocoa, coffee, strawberry, pineapple, pepper, hop oil, cognac, peanut, honey, starfruit, Bourbon vanilla, mountain papaya, roasted chicory root and rooibus tea (Aspalathus linearis).
Verwenden
Methyl phenylacetate is utilized for partition coefficient measurement experiments. It is mainly used in the flavor industry and in perfumes to impart honey scents. Further, it acts as a precursor to prepare synthetic perfumes. It acts as an acylating agent and involved in the enantioselective acylation of beta-lactam intermediate using penicillin G amidase.
Herstellung & Synthese
synthetische
Methyl phenylacetate is synthesized from phenylacetonitrile by hydrolysis and esterification. Put methanol into a dry glass-lined reaction pot, stir and cool to below 30°C, add sulfuric acid dropwise, heat up to 90°C after adding, and start adding phenylacetonitrile dropwise, control the temperature at about 95°C, and finish adding in 1.5h. After reacting at 95-100 °C for 6 h, it was cooled to below 40 °C and diluted with water equivalent to about 0.6 times the reaction solution. The acid water was separated by standing, and a saturated sodium carbonate solution was added for neutralization and washing, and the aqueous layer was discarded. It is dehydrated with anhydrous calcium chloride and fractionated under reduced pressure to obtain methyl phenylacetate with a yield of 80%.