77-83-8 Usage
Description
Ethyl 3-methyl-3-phenylglycidate, also known as "strawberry aldehyde," is a synthetic flavoring agent that is a glycidic acid ester. It is a clear, colorless to pale yellow liquid with a strong fruit odor suggestive of strawberries. Ethyl 3-methyl-3-phenylglycidate exists as two optically active pairs of cisand trans-isomers, and the commercial product is a racemic mixture of all four isomers, which has a strong, sweetish, strawberry odor.
Uses
Used in Flavor Industry:
Ethyl 3-methyl-3-phenylglycidate is used as an artificial fruit flavor, particularly for strawberry, in the flavor industry. It is added to candy, beverages, and ice cream at concentrations of 6–20 ppm to provide a sweet, ripe, strawberry jam and preserve note.
Used in Fragrance Industry:
Ethyl 3-methyl-3-phenylglycidate is also used in the fragrance industry to provide a sweet, berry, strawberry, fruity, tutti-frutti, and floral nuance to various products.
Used in Strawberry Flavoring:
Ethyl 3-methyl-3-phenylglycidate is used as a key component in creating the characteristic strawberry flavor in various food and beverage products. It is known for its strong fruity odor suggestive of strawberry and its slightly acid taste reminiscent of the fruit.
Used in Research and Development:
Due to its unique chemical properties and strong odor, Ethyl 3-methyl-3-phenylglycidate is also used in research and development for the creation of new flavor compounds and the study of its chemical behavior in different applications.
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.
Air & Water Reactions
Insoluble in water.
Reactivity Profile
Esters, such as Ethyl 3-methyl-3-phenylglycidate, 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.
Fire Hazard
Ethyl 3-methyl-3-phenylglycidate is probably combustible.
Trade name
Strawberry pure (Givaudan)
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.
Check Digit Verification of cas no
The CAS Registry Mumber 77-83-8 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 7 and 7 respectively; the second part has 2 digits, 8 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 77-83:
(4*7)+(3*7)+(2*8)+(1*3)=68
68 % 10 = 8
So 77-83-8 is a valid CAS Registry Number.
InChI:InChI=1/C12H14O3/c1-3-14-11(13)10-12(2,15-10)9-7-5-4-6-8-9/h4-8,10H,3H2,1-2H3/t10-,12-/m1/s1
77-83-8Relevant articles and documents
Enantioselective epoxidation of β,β-disubstituted enamides with a manganese catalyst and aqueous hydrogen peroxide
Clarasó, Carlota,Vicens, Laia,Polo, Alfonso,Costas, Miquel
, p. 2430 - 2435 (2019/03/29)
Enantioselective epoxidation of β,β-disubstituted enamides with aqueous hydrogen peroxide and a novel manganese catalyst is described. Epoxidation is stereospecific and proceeds fast under mild conditions. Amides are disclosed as key functional groups to enable high enantioselectivity.
A versatile synthetic platform based on strained propargyl amines
He, Zhi,Yudin, Andrei K.
supporting information; experimental part, p. 1607 - 1610 (2010/06/16)
"Chemical Equation Presented" Divergent reactivity: Various ethynylaziridines behave as strained propargyl amines and can be directly converted into unprotected α-amino allenes by a highly diastereoselective SN2′ hydride delivery (see scheme). Additional reaction routes involve chemo- and regioselective transformation into either bicyclic aziridine/ enol ethers or highly strained azirine alkynes.
An efficient synthesis of 2-bromo-3-hydroxy esters by reaction of ketones with ethyl dibromoacetate promoted by samarium diiodide
Concellon, Jose M.,Concellon, Carmen,Diaz, Pamela
, p. 2197 - 2200 (2007/10/03)
A simple and efficient samarium diiodide mediated synthesis of 2-bromo-3-hydroxy esters 1 by the reaction of a variety of ketones 2 with ethyl dibromoacetate (3) is described. The relative configuration of the major diastereoisomer obtained was established by NOESY experiments of the corresponding α,β-epoxy esters 4 prepared from 1. Additionally, a mechanism is proposed to explain the results obtained. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.