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Ethyl-2,3-epoxy-3-phenylbutyrat
ALDEHYDE C-16 · STRAWBERRY ALDEHYDE · ETHYL 2,3-EPOXY-3-PHENYLBUTYRATE · FEMA 2444 · Strawberry · ETHYL METHYL PHENYL GLYCIDATE · Oxiranecarboxylic acid, 3-methyl-3-phenyl-, ethyl ester, trans- · Fraeseol
Identifikatoren & physikalische Daten
| CAS No. | 19464-95-0 |
|---|---|
| Summenformel | C12H14O3 |
| Durchschnittliche Molmasse | 206,24 g/mol |
| Monoisotopische Masse | 206,0942943 g/mol |
| SMILES | CCOC(=O)C1OC1(C)c1ccccc1 |
| InChIKey | LQKRYVGRPXFFAV-UHFFFAOYSA-N |
| PubChem CID | 6501 |
| ChEMBL | CHEMBL1890407 |
| ChEBI | CHEBI:173581 |
| EC No. | 201-061-8 |
| DTXSID | DTXSID8020591 |
| Lokaler Name | Ethyl-2,3-epoxy-3-phenylbutyrat |
Chemische & physikalische Eigenschaften
| XLogP | 1,9 |
|---|---|
| Polarare Oberfläche (TPSA) | 38,8 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 4 |
| Schwere Atome | 15 |
| Formalladung | 0 |
| Komplexität | 245 |
| Stoffklassen | Other Classes -> Esters, Other |
| Kosmetika | Viscosity controlling |
| SpringerMaterials Properties | Surface tension |
| Duftstoffe | Fragrance Ingredient (Ethyl methylphenylglycidate) -> IFRA transparency List |
| Geruch | ON DILUTION, STRONG FRUITY ODORFRUITY, BERRY AROMA |
| Geschmack | CHARACTERISTIC SLIGHTLY ACID TASTE REMINISCENT OF STRAWBERRYAPPLE, BERRY TASTE |
| Lebensmittelzusatzstoffe | FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food |
| Dichte | 1.104 to 1.123 at 68 °F (NTP, 1992)1.0442 @ 20 °C1.086-1.0961.087 g/mL at 25 °C(lit.) |
| Aromastoffe | EU Flavoring substances |
| Color/Form | COLORLESS TO PALE-YELLOW LIQUID |
| Löslichkeit | Insoluble (<1 mg/ml at 68 °F) (NTP, 1992)SOL IN 3 VOLUMES OF 60% ALCOHOL1:3 & MORE IN 70% ALCOHOL1:2 IN 80% ALCINSOL IN WATERSOL IN MOST ORGANIC SOLVENTSInsoluble in water, glycerolSoluble in propylene glycol, fixed oilsSoluble (in ethanol) |
| Flammpunkt | greater than 200 °F (NTP, 1992)134 °C>230 °F |
| Siedepunkt | 272-275 °C(lit.) |
| Brechungsindex | n20/D 1.505(lit.) |
| FEMA | 2444 | ETHYL METHYLPHENYLGLYCIDATE |
| Lagerbedingungen | 2-8°C |
| Aggregatzustand | clear liquid |
| Farbe | Colorless to Light orange to Yellow |
| Geruch | at 100.00 %. sweet fruity strawberry floral honey fatty |
| Geruchsart | fruity |
| Biologische Quelle | synthetic |
| JECFA Number | 1577 |
| BRN | 12299 |
| Hauptanwendungen | flavors and fragrances |
| Kosmetik-Inhaltsstoffe Funktionen | VISCOSITY CONTROLLINGPERFUMING |
| InChI | 1S/C12H14O3/c1-3-14-11(13)10-12(2,15-10)9-7-5-4-6-8-9/h4-8,10H,3H2,1-2H3 |
| InChIKey | LQKRYVGRPXFFAV-UHFFFAOYSA-N |
| SMILES | CCOC(=O)C1OC1(C)c2ccccc2 |
| LogP (Verteilungskoeffizient) | 2.43 |
| CAS Datenbank | 77-83-8(CAS DataBase Reference) |
| NIST chemische Informationen | Glycidic acid, 3-methyl-3-phenyl, ethyl ester(77-83-8) |
| EPA chemische Informationen | Ethyl methylphenylglycidate (77-83-8) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 1.1% (22 of 1918) of reports.WarningH317 (79%): May cause an allergic skin reaction [Warning Sensitization, Skin]P261, P272, P273, P280, P302+P352, P321, P333+P317, P362+P364, P391, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 1918 reports by companies from 15 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Chemical: Oxiranecarboxylic acid, 3-methyl-3-phenyl-, ethyl esterCommission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)2-Oxiranecarboxylic acid, 3-methyl-3-phenyl-, ethyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Oxiranecarboxylic acid, 3-methyl-3-phenyl-, ethyl ester 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)REACH registered substance: Ethyl 2,3-epoxy-3-phenylbutyrate (EC: 201-061-8)Oxiranecarboxylic acid, 3-methyl-3-phenyl-, ethyl ester: Does not have an individual approval but may be used under an appropriate group standard |
| Brandgefahren | This chemical is probably combustible. (NTP, 1992) |
| Gefahrenübersicht | A mutagenCauses somnolence and change in liver enzymes in high-dose rat feeding studies[RTECS] Acceptable daily intake = 0-0.5 mg/kg bw[JECFA] Caused no skin irritation or sensitization in 25 human volunteers (1% in petrolatum)Effects in 16 week feeding study with rats at 10000 ppm include testicular atrophyObservations in two year feeding study with rats include hindquarter paralysis and histopathological changes to sciatic nerveNo histopathological organ changes or evidence of carcinogenicity in long term feeding studies[HSDB] |
| FDA-Anforderungen | CODE OF FEDERAL REGULATIONS TITLE 21, SECTION 182.60....APPROVED BY THE FDA FOR FOOD USE (CODE OF FEDERAL REGULATIONS TITLE 21, SECTION 121.1164). |
Anwendungen & Verwendung
Occurrence
Has apparently not been reported to occur in nature.
Verwenden
Ethyl 3-methyl-3-phenylglycidate is a synthetic flavoring agent that is a glycidic acid ester. It is a colorless to pale yellow liquid with a strong fruit odor suggestive of strawberries. It is unstable to alkali and moderately stable to weak organic acids. It should be stored in glass, tin, or aluminum containers. It is soluble in fixed oils and in propylene glycol. It is used in flavors for strawberry note and has application in candy, beverages, and ice cream at 6–20 ppm. It is also termed aldehyde c-16.
Herstellung & Synthese
synthetische
By reaction of acetophenone and the ethyl ester of monochloroacetic acid in the presence of an alkaline condensing agent.