Ethyl butyrate, also known as ethyl butanoate, or butyric ether, is an
ester
In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides ar ...
with the chemical formula CH
3CH
2CH
2COOCH
2CH
3. It is soluble in
propylene glycol
Propylene glycol (IUPAC nomenclature, IUPAC name: propane-1,2-diol) is a viscous, colorless liquid, which is nearly odorless but possesses a faintly sweet taste. Its chemical formula is CH3CH(OH)CH2OH.
Containing two Alcohol (chemistry), alcoho ...
,
paraffin oil, and
kerosene
Kerosene, paraffin, or lamp oil is a combustible hydrocarbon liquid which is derived from petroleum. It is widely used as a fuel in aviation as well as households. Its name derives from el, κηρός (''keros'') meaning "wax", and was regi ...
. It has a fruity odor, similar to
pineapple
The pineapple (''Ananas comosus'') is a tropical plant with an edible fruit; it is the most economically significant plant in the family Bromeliaceae. The pineapple is indigenous to South America, where it has been cultivated for many centuri ...
, and is a key ingredient used as a flavor enhancer in processed orange juices.
[ It also occurs naturally in many fruits, albeit at lower concentrations.]
Uses
It is commonly used as artificial flavor
A flavoring (or flavouring), also known as flavor (or flavour) or flavorant, is a food additive used to improve the taste or smell of food. It changes the perceptual impression of food as determined primarily by the chemoreceptors of the gustat ...
ing resembling orange juice
Orange juice is a liquid extract of the orange (fruit), orange tree fruit, produced by squeezing or reaming oranges. It comes in several different varieties, including blood orange, navel oranges, valencia orange, clementine, and tangerine. A ...
and is hence used in nearly all orange juices sold, including those sold as "fresh
Fresh or FRESH may refer to:
People
*DJ Fresh (born 1977), UK-based drum and bass artist
*DJ Fresh (producer), US-based R&B producer born Marqus Brown
Arts, entertainment, and media Films
* ''Fresh'' (1994 film), a crime film
* ''Fresh'' (200 ...
" or “concentrated". It is also used in alcoholic beverages (e.g. martinis, daiquiris etc.), as a solvent in perfume
Perfume (, ; french: parfum) is a mixture of fragrant essential oils or aroma compounds (fragrances), fixatives and solvents, usually in liquid form, used to give the human body, animals, food, objects, and living-spaces an agreeable scent. Th ...
ry products, and as a plasticizer
A plasticizer ( UK: plasticiser) is a substance that is added to a material to make it softer and more flexible, to increase its plasticity, to decrease its viscosity, and/or to decrease friction during its handling in manufacture.
Plasticiz ...
for cellulose
Cellulose is an organic compound with the formula , a polysaccharide consisting of a linear chain of several hundred to many thousands of β(1→4) linked D-glucose units. Cellulose is an important structural component of the primary cell wall ...
.
Ethyl butyrate is one of the most common chemicals used in flavor
Flavor or flavour is either the sensory perception of taste or smell, or a flavoring in food that produces such perception.
Flavor or flavour may also refer to:
Science
*Flavors (programming language), an early object-oriented extension to Lis ...
s and fragrance
An aroma compound, also known as an odorant, aroma, fragrance or flavoring, is a chemical compound that has a smell or odor. For an individual chemical or class of chemical compounds to impart a smell or fragrance, it must be sufficiently vol ...
s. It can be used in a variety of flavors: orange (most common), cherry, pineapple, mango, guava, bubblegum, peach, apricot, fig, and plum. In industrial use, it is also one of the cheapest chemicals, which only adds to its popularity.
Production
It can be synthesized by reacting ethanol
Ethanol (abbr. EtOH; also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound. It is an Alcohol (chemistry), alcohol with the chemical formula . Its formula can be also written as or (an ethyl ...
and butyric acid
Butyric acid (; from grc, βούτῡρον, meaning "butter"), also known under the systematic name butanoic acid, is a straight-chain alkyl carboxylic acid with the chemical formula CH3CH2CH2CO2H. It is an oily, colorless liquid with an unple ...
. This is a condensation reaction
In organic chemistry, a condensation reaction is a type of chemical reaction in which two molecules are combined to form a single molecule, usually with the loss of a small molecule such as water. If water is lost, the reaction is also known as a ...
, meaning water is produced in the reaction as a byproduct. Ethyl butyrate from natural sources can be distinguished from synthetic ethyl butyrate by Stable Isotope Ratio Analysis (SIRA).
Table of physical properties
See also
* Butyric acid
Butyric acid (; from grc, βούτῡρον, meaning "butter"), also known under the systematic name butanoic acid, is a straight-chain alkyl carboxylic acid with the chemical formula CH3CH2CH2CO2H. It is an oily, colorless liquid with an unple ...
* Butyrate
The conjugate acids are in :Carboxylic acids.
{{Commons category, Carboxylate ions, Carboxylate anions
Carbon compounds
Oxyanions ...
s
* Methyl butyrate
Methyl butyrate, also known under the systematic name methyl butanoate, is the methyl ester of butyric acid. Like most esters, it has a fruity odor, in this case resembling apples or pineapples. At room temperature, it is a colorless liquid with ...
References
External links
MSDS sheet
Sorption of ethyl butyrate and octanal constituents of orange essence by polymeric adsorbents
Biosynthesis of ethyl butyrate using immobilized lipase: a statistical approach
{{Authority control
Ethyl esters
Butyrate esters
Ester solvents
Flavors
Plasticizers
Sweet-smelling chemicals