Names | |
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Preferred IUPAC name Ethyl butanoate | |
Other names Butanoic acid ethyl ester Ethyl butyrate Butyric acid ethyl ester Ethyl n-butanoate Ethyl n-butyrate Butyric ether UN 1180 | |
Identifiers | |
3D model (JSmol) | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.003.007 |
EC Number |
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PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties [1] | |
C6H12O2 | |
Molar mass | 116.160 g·mol−1 |
Appearance | Colorless liquid with fruity odor (typically pineapple) |
Density | 0.879 g/cm3 |
Melting point | −93 °C (−135 °F; 180 K) |
Boiling point | 120–121 °C (248–250 °F; 393–394 K) |
Soluble in 150 parts | |
Vapor pressure | 1510 Pa (11.3 mmHg) |
−77.7×10−6 cm3/mol | |
Hazards | |
GHS labelling: | |
Warning | |
H226 | |
P210, P233, P240, P241, P242, P243, P280, P303+P361+P353, P370+P378, P403+P235, P501 | |
NFPA 704 (fire diamond) | |
Flash point | 26 °C; 78 °F; 299 K c.c. |
463 °C (865 °F; 736 K) | |
Lethal dose or concentration (LD, LC): | |
LD50 (median dose) | 1350 mg/kg (oral, rat) [1] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Ethyl butyrate, also known as ethyl butanoate, or butyric ether, is an ester with the chemical formula CH3CH2CH2COOCH2CH3. It is soluble in propylene glycol, paraffin oil, and kerosene. It has a fruity odor, similar to pineapple, and is a key ingredient used as a flavor enhancer in processed orange juices. [1] It also occurs naturally in many fruits, albeit at lower concentrations. [2]
It is commonly used as artificial flavoring resembling orange juice [3] and is hence used in nearly all orange juices sold in the US, including those sold as "fresh" or “concentrated". [4] It is also used in alcoholic beverages (e.g. martinis, daiquiris etc.), as a solvent in perfumery products, and as a plasticizer for cellulose.
Ethyl butyrate is one of the most common chemicals used in flavors and fragrances. It can be used in a variety of flavors: orange (most common), cherry, pineapple, mango, guava, bubblegum, peach, apricot, fig, and plum. Ethyl butyrate is synthesised in Jamaican rum upon the estrification of butyric acid from muck and ethanol during the distillation process. This gives Jamaican rum its pleasant flavour. In industrial use, it is also one of the cheapest chemicals, which only adds to its popularity.
It can be synthesized by reacting ethanol and butyric acid. This is a condensation reaction, 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). [5]
This section needs additional citations for verification .(January 2017) |
Property | Value |
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Critical temperature (Tc) | 296 °C (569 K) |
Critical pressure (pc) | 3.10 MPa (30.64 bar) |
Critical density (ρc) | 2.38 mol.l−1 |
Refractive index (n) at 20 °C | 1.390 - 1.394 |
Ethanol is an organic compound with the chemical formula CH3CH2OH. It is an alcohol, with its formula also written as C2H5OH, C2H6O or EtOH, where Et stands for ethyl. Ethanol is a volatile, flammable, colorless liquid with a characteristic wine-like odor and pungent taste. It is a psychoactive recreational drug, and the active ingredient in alcoholic drinks.
Tequila is a distilled beverage made from the blue agave plant, primarily in the area surrounding the city of Tequila 65 km (40 mi) northwest of Guadalajara, and in the Jaliscan Highlands of the central western Mexican state of Jalisco.
Orange juice is a liquid extract of the 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. As well as variations in oranges used, some varieties include differing amounts of juice vesicles, known as "pulp" in American English, and "(juicy) bits" in British English. These vesicles contain the juice of the orange and can be left in or removed during the manufacturing process. How juicy these vesicles are depend upon many factors, such as species, variety, and season. In American English, the beverage name is often abbreviated as "OJ".
Grenadine is a commonly used nonalcoholic bar syrup characterized by its deep red color. It is a popular cocktail ingredient renowned for its flavor as well as its ability to give a reddish or pink tint to mixed drinks. Grenadine was traditionally made from pomegranate but is more often encountered as a commercial imitation with few to no actual fruit components.
Butyric acid, 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 unpleasant odor. Isobutyric acid is an isomer. Salts and esters of butyric acid are known as butyrates or butanoates. The acid does not occur widely in nature, but its esters are widespread. It is a common industrial chemical and an important component in the mammalian gut.
Diethyl ether, or simply ether, is an organic compound in the ether class with the formula C4H10O, (CH3CH2)2O or (C2H5)2O, sometimes abbreviated as Et2O. It is a colourless, highly volatile, sweet-smelling, extremely flammable liquid. It is commonly used as a solvent in laboratories and as a starting fluid for some engines. It was formerly used as a general anesthetic, until non-flammable drugs were developed, such as halothane. It has been used as a recreational drug to cause intoxication.
Ethyl acetate is the organic compound with the formula CH3CO2CH2CH3, simplified to C4H8O2. This colorless liquid has a characteristic sweet smell and is used in glues, nail polish removers, and in the decaffeination process of tea and coffee. Ethyl acetate is the ester of ethanol and acetic acid; it is manufactured on a large scale for use as a solvent.
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 low solubility in water, upon which it floats to form an oily layer. Although it is flammable, it has a relatively low vapor pressure, so it can be safely handled at room temperature without special safety precautions.
Ethyl formate is an ester formed when ethanol reacts with formic acid. Ethyl formate has the characteristic smell of rum and is partially responsible for the flavor of raspberries, occurring naturally in some plant oils, fruits, and juices. Ethyl formate does not occur naturally in the animal kingdom.
The garden strawberry is a widely grown hybrid species of the genus Fragaria, collectively known as the strawberries, which are cultivated worldwide for their fruit. The fruit is widely appreciated for its characteristic aroma, bright red color, juicy texture, and sweetness. It is consumed in large quantities, either fresh or in such prepared foods as jam, juice, pies, ice cream, milkshakes, and chocolates. Artificial strawberry flavorings and aromas are also widely used in products such as candy, soap, lip gloss, perfume, and many others.
An extract (essence) is a substance made by extracting a part of a raw material, often by using a solvent such as ethanol, oil or water. Extracts may be sold as tinctures, absolutes or in powder form.
Dimethyl dicarbonate (DMDC) is a colorless liquid with a pungent odor at high concentration at room temperature. It is primarily used as a beverage preservative, processing aid, or sterilant being highly active against typical beverage spoiling microorganisms like yeast, bacteria, or mould.
Butyl butyrate, or butyl butanoate, is an organic compound that is an ester formed by the condensation of butyric acid and n-butanol. It is a clear, colorless liquid that is insoluble in water, but miscible with ethanol and diethyl ether. Its refractive index is 1.406 at 20 °C.
The bioconversion of biomass to mixed alcohol fuels can be accomplished using the MixAlco process. Through bioconversion of biomass to a mixed alcohol fuel, more energy from the biomass will end up as liquid fuels than in converting biomass to ethanol by yeast fermentation.
Fermentation is a metabolic process that produces chemical changes in organic substances through the action of enzymes. In biochemistry, it is broadly defined as the extraction of energy from carbohydrates in the absence of oxygen. In food production, it may more broadly refer to any process in which the activity of microorganisms brings about a desirable change to a foodstuff or beverage. The science of fermentation is known as zymology.
Methyl anthranilate, also known as MA, methyl 2-aminobenzoate, or carbomethoxyaniline, is an ester of anthranilic acid. Its chemical formula is C8H9NO2. It has a strong and fruity grape smell, and one of its key uses is as a flavoring agent.
The process of fermentation in winemaking turns grape juice into an alcoholic beverage. During fermentation, yeasts transform sugars present in the juice into ethanol and carbon dioxide. In winemaking, the temperature and speed of fermentation are important considerations as well as the levels of oxygen present in the must at the start of the fermentation. The risk of stuck fermentation and the development of several wine faults can also occur during this stage, which can last anywhere from 5 to 14 days for primary fermentation and potentially another 5 to 10 days for a secondary fermentation. Fermentation may be done in stainless steel tanks, which is common with many white wines like Riesling, in an open wooden vat, inside a wine barrel and inside the wine bottle itself as in the production of many sparkling wines.
This glossary of winemaking terms lists some of terms and definitions involved in making wine, fruit wine, and mead.
Ethyl octanoate, also known as ethyl caprylate, is a fatty acid ester formed from caprylic acid and ethanol. A colorless liquid at room temperature, it has the semi-developed formula of CH3(CH2)6COOCH2CH3, and is used in food industries as a flavoring and in the perfume industry as a scent additive. It is present in many fruits and alcoholic beverages, and has a strong odor of fruit and flowers. It is used in the creation of synthetic fruity scents.
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