Description
Ethyl 2-methylbutyrate is the ethyl ester form of the 2-methylbutyrate with pleasant sweet aroma. It is a naturally occurring ester which is found in apple, wine, orange, strawberry, cheese, milk, mango, cognac, etc. It is a highly valuable flavoring agent used in flavoring in foods and beverages as well as fragrance in perfume and perfumed products. It is generally prepared through the esterification between alcohol and 2-methylbutyrate.
References
Dimick, Paul S., Jonathan C. Hoskin, and Terry E. Acree. "Review of apple flavor—State of the art∗." Critical Reviews in Food Science & Nutrition 18.4 (1983): 387-409.
Konczal, J. B., et al. "Apple juice flavor compound sorption by sealant films."Journal of food science 57.4 (1992): 967-970.
Djojoputro, Hiannie, and Suryadi Ismadji. "Density and viscosity of binary mixtures of ethyl-2-methylbutyrate and ethyl hexanoate with methanol, ethanol, and 1-propanol at (293.15, 303.15, and 313.15) K." Journal of Chemical & Engineering Data 50.4 (2005): 1343-1347.
Chemical Properties
clear colorless liquid
Chemical Properties
Ethyl 2-methylbutyrate has a powerful, green-fruity, apple-like odor.
Chemical Properties
Ethyl 2-Methylbutyrate is a liquid with
a green, fruity odor reminiscent of apples. It is found, for example, in citrus fruits
and wild berries and is used in fruit flavor compositions.
Occurrence
Reported found in nature; the ethyl l-methylbutyrate has been identified in strawberry juice; because of the
presence of the asymmetric carbon, the compound should exhibit optically active forms as well as the racemic form; however,
only the d-form and the racemic form are known. Reported found in apple juice, orange and grapefruit juice, bilberry, pineapple,
strawberry, cheeses, milk, cognac, rum, whiskey, cider, mango, mountain papaya, spineless monkey orange (Strychnos madagasc.),
Chinese quince and German chamomile oil.
Uses
Ethyl 2-Methylbutyrate-d9 is deuterium labelled ethyl 2-methylbutyrate, which is an ester that has a sweet, apple-like aroma. Ethyl 2-methylbutyrate is naturally found in apples, cherries and orange juice.
Preparation
The racemic form can be prepared catalytically by several methods: from butene and Ni(CO)4 under nitrogen in ethyl
alcohol/acetic acid solution, or from ethylene and CO under pressure using HBF4 and HF as catalysts.
Definition
ChEBI: Ethyl 2-methylbutyrate is a fatty acid ethyl ester obtained by the formal condensation of 2-methylbutyric acid with ethanol. It is a constituent of the aroma of wines, strawberries, blueberries, and apples. It has a role as a flavouring agent, a plant metabolite, a human metabolite and a fragrance. It is a volatile organic compound and a fatty acid ethyl ester. It is functionally related to an ethanol and a 2-methylbutyric acid.
Aroma threshold values
Detection: 0.01 to 0.1 ppb
Taste threshold values
Taste characteristics at 40 ppm: fruity, green, berry, strawberry, fresh apple, pineapple and raspberry
General Description
A colorless oily liquid with a fruity odor. Insoluble in water and less dense than water. Flash point 73°F. Contact may irritate skin, eyes and mucous membranes.
Air & Water Reactions
Highly flammable. Insoluble in water.
Reactivity Profile
ETHYL-2-METHYL BUTYRATE is an ester. Esters 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.
Health Hazard
Inhalation or contact with material may irritate or burn skin and eyes. Fire may produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.
Flammability and Explosibility
Non flammable
Safety Profile
Combustible liquid.
When heated to decomposition it emits
acrid smoke and irritating fumes.
Solubility in organics
Very slightly soluble
in water, soluble in alcohol and Propylene
glycol, miscible with perfume and flavor oils.
