| Identification | More | [Name]
Ethyl 3-methyl-3-phenylglycidate | [CAS]
77-83-8 | [Synonyms]
3-Methyl-3-phenyl glycidic acid ethyl ester
ALDEHYDE C-16
ETHYL 2,3-EPOXY-3-PHENYLBUTYRATE
ETHYL 3-METHYL-2,3-EPOXY-HYDROCINAMIC ACID
ETHYL 3-METHYL-3-PHENYLGLYCIDATE
ETHYL 3-PHENYL-2,3-EPOXYBUTYRATE
ETHYL-A B-EPOXY-B-METHYLHYDROCINNAMATE
ETHYL BETA-METHYL-BETA-PHENYLGLYCIDATE
ETHYL METHYL PHENYL GLYCIDATE
FEMA 2444
GLYCIDIC ACID, 3-METHYL-3-PHENYL:ETHYL ESTER
STRAWBERRY ALDEHYDE
2,3-epoxy-3-phenyl-butanoicaciethylester
2,3-Epoxy-3-phenylbutyric acid, ethyl ester
3-methyl-3-phenyl-oxiranecarboxylicacid,ethylester
3-methyl-3-phenyl-oxiranecarboxylicacidethylester
3-methyl-3-phenyl-oxiranecarboxylicaciethylester
alpha,beta-Epoxy-beta-methylhydrocinnamic acid, ethyl ester
alpha,beta-epoxy-beta-methylhydrocinnamicacid,ethylester
alpha,beta-epoxy-beta-methyl-hydrocinnamicaciethylester | [EINECS(EC#)]
201-061-8 | [Molecular Formula]
C12H14O3 | [MDL Number]
MFCD00022338 | [Molecular Weight]
206.24 | [MOL File]
77-83-8.mol |
| Chemical Properties | Back Directory | [Appearance]
clear yellow liquid | [Boiling point ]
272-275 °C(lit.) | [density ]
1.087 g/mL at 25 °C(lit.)
| [FEMA ]
2444 | [refractive index ]
n20/D 1.505(lit.)
| [Fp ]
>230 °F
| [storage temp. ]
2-8°C | [form ]
clear liquid | [color ]
Colorless to Light orange to Yellow | [Odor]
at 100.00 %. sweet fruity strawberry floral honey fatty | [Odor Type]
fruity | [JECFA Number]
1577 | [BRN ]
12299 | [LogP]
2.43 | [Uses]
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. | [CAS DataBase Reference]
77-83-8(CAS DataBase Reference) | [NIST Chemistry Reference]
Glycidic acid, 3-methyl-3-phenyl, ethyl ester(77-83-8) | [EPA Substance Registry System]
77-83-8(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R10:Flammable.
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S16:Keep away from sources of ignition-No smoking .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [RIDADR ]
UN 1993 3/PG 3
| [WGK Germany ]
2
| [RTECS ]
MW5250000
| [TSCA ]
Yes | [HS Code ]
29189090 | [Safety Profile]
Mddly toxic by
ingestion. Mutation data reported.
Combustible liquid. When heated to
decomposition it emits acrid smoke and
irritating fumes. See also ALDEHYDES. | [Hazardous Substances Data]
77-83-8(Hazardous Substances Data) | [Toxicity]
LD50 orally in Rabbit: 5470 mg/kg |
| Hazard Information | Back Directory | [General Description]
Clear, colorless to yellowish liquid with a strawberry-like odor. | [Reactivity Profile]
Esters, such as 3-METHYL-3-PHENYLGLYCIDIC ACID ETHYL ESTER(77-83-8), react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides. | [Air & Water Reactions]
Insoluble in water. | [Fire Hazard]
This chemical is probably combustible. | [Chemical Properties]
clear yellow liquid | [Chemical Properties]
Ethyl 3-Methyl-3-phenylglycidate exists as two optically
active pairs of cis- and trans-isomers; each isomer has a characteristic odor
. The commercial product is a racemic mixture of all four isomers and has
a strong, sweetish, strawberry odor. The cis/trans ratio obtained in the Darzens
condensation of acetophenone (R==CH3) and ethyl chloroacetate depends on the
base used in the reaction. | [Chemical Properties]
Ethyl methylphenylglycidate on dilution has a strong fruity odor suggestive of strawberry. It has a characteristic, slightly
acid taste reminiscent of strawberry. | [Chemical Properties]
Perennial, herbaceous plant; grows wild or cultivated in central–southern Europe, North America and Asia. The plant grows 10 to 20 cm (4 to 8 in.) in height and has thick rhizomes; radical leaves with long, small, white flowers blossoming from April to July; and fleshy, ovoidal, red berries covered with numerous achenes. The only part used is the berries. Strawberry has a sweet–sour taste and a characteristic odor. | [Occurrence]
Has apparently not been reported to occur in nature. | [Definition]
ChEBI: Phenylmethylglycidic ester is a carboxylic acid and an epoxide. | [Preparation]
By reaction of acetophenone and the ethyl ester of monochloroacetic acid in the presence of an alkaline condensing agent. | [Composition]
Strawberry aroma has been the subject of extensive investigation. Several components have been identified, of which only 7% appear to be responsible for the aroma. Strawberry aroma varies widely with the strawberry variety. The most valuable part, aroma, is from wild strawberry. | [Aroma threshold values]
Detection: 2 ppm | [Taste threshold values]
Taste characteristics at 1 and 5% sucrose: sweet, ripe, strawberry jam and preserve notes. | [Taste threshold values]
Taste characteristics at 50 ppm: sweet, berry, strawberry, fruity, tutti-frutti and floral nuances | [Trade name]
Strawberry pure (Givaudan) | [Synthesis]
Ethyl 3-methyl-3-phenylglycidate is synthesized by Acetophenone by condensation with Ethyl monochloroacetate in an alkaline solution, using sodium as a condensing agent.
| [Solubility in organics]
Poorly soluble in Propylene glycol, Glycerin and mineral oil, soluble in alcohol, miscible with most perfume and flavor oils.
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