Ethyl butyrate

Names
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

CAS Number

* 105-54-4 Y

3D model (JSmol)

* Interactive image

ChEBI |

* CHEBI:88764 Y

ChEMBL |

* ChEMBL44800 Y

ChemSpider |

* 7475 Y

ECHA InfoCard | 100.003.007
EC Number |

* 203-306-4

PubChem CID

* 7762

UNII |

* UFD2LZ005D Y

CompTox Dashboard (EPA)

* DTXSID6040111

InChI

* InChI=1S/C6H12O2/c1-3-5-6(7)8-4-2/h3-5H2,1-2H3 Y

Key: OBNCKNCVKJNDBV-UHFFFAOYSA-N Y

* InChI=1/C6H12O2/c1-3-5-6(7)8-4-2/h3-5H2,1-2H3

Key: OBNCKNCVKJNDBV-UHFFFAOYAO

SMILES

* CCCC(=O)OCC

Properties[1]

Chemical formula

| 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)

Solubility in water

| Soluble in 150 parts
Vapor pressure | 1510 Pa (11.3 mmHg)

Magnetic susceptibility (χ)

| −77.7×10−6 cm3/mol
Hazards
GHS labelling:

Pictograms

Signal word

| Warning

Hazard statements

| H226

Precautionary statements

| 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.

Autoignition
temperature

| 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).

Y verify (what is YN ?)

Infobox references

Chemical compound

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]

## Uses

[edit]

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.

## Production

[edit]

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]

## Table of physical properties

[edit]

This section needs additional citations for verification. Please help improve this article by adding citations to reliable sources in this section. Unsourced material may be challenged and removed. (January 2017) (Learn how and when to remove this message)

|

Property  | Value

|

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

## See also

[edit]

* Butyric acid
* Butyrates
* Methyl butyrate

## References

[edit]

1. ^ a b c Merck Index, 12th Edition, 3822
2. ^ Schieberle, H.-D. Belitz, W. Grosch, P. (2009). Food chemistry (4th rev. and extended ed.). Berlin: Springer. ISBN 9783540699330.`{{cite book}}`: CS1 maint: multiple names: authors list (link)
3. ^ Andrea Walker (12 May 2009). "Ask an Academic: Orange Juice". The New Yorker.
4. ^ Hamilton, Alissa. Squeezed. Yale University.
5. ^ Ashurst, P.R.; Dennis, M.J. (1998). Analytical methods of food authentication (1st ed.). London: Blackie Academic & Professional. ISBN 9780751404265. Retrieved 27 January 2016.

## External links

[edit]

* MSDS sheet
* Sorption of ethyl butyrate and octanal constituents of orange essence by polymeric adsorbents Archived 2009-05-01 at the Wayback Machine
* Biosynthesis of ethyl butyrate using immobilized lipase: a statistical approach Archived 2009-05-01 at the Wayback Machine

* v
* t
* e

Esters

Methyl esters|

* Methyl formate
* Methyl acetate
* Methyl propionate
* Methyl butyrate
* Methyl pentanoate
* Methyl hexanoate
* Methyl benzoate

Ethyl esters|

* Ethyl formate
* Ethyl acetate
* Ethyl propionate
* Ethyl butyrate
* Ethyl pentanoate
* Ethyl hexanoate
* Ethyl heptanoate
* Ethyl octanoate
* Ethyl decanoate
* Ethyl palmitate
* Ethyl benzoate

Propyl esters|

* Propyl acetate
* Propyl propanoate
* Propyl benzoate
* Isopropyl acetate
* Isopropyl palmitate

Butyl esters|

* Butyl acetate
* Butyl butyrate
* Isobutyl acetate
* sec-Butyl acetate
* tert-Butyl acetate

Amyl esters|

* Amyl acetate
* Pentyl propanoate
* Pentyl butyrate
* Pentyl pentanoate
* Pentyl hexanoate
* Isoamyl formate
* Isoamyl acetate
* Sec-Amyl acetate

Hexyl esters|

* Hexyl acetate

Phenyl esters|

* Phenyl acetate

Heptyl esters|

* Heptyl acetate
* Heptyl butyrate

Benzyl esters|

* Benzyl acetate
* Benzyl benzoate

Authority control databases: National |

* Germany

|

*[CID]: Compound ID
*[EPA]: U.S. Environmental Protection Agency
*[H226]: H226: Flammable liquid and vapour
*[P210]: P210: Keep away from heat, hot surfaces, sparks, open flames and other ignition sources. No smoking.
*[P233]: P233: Keep container tightly closed.
*[P240]: P240: Ground and bond container and receiving equipment.
*[P241]: P241: Use explosion-proof electrical/ventilating/light/.../equipment.
*[P242]: P242: Use only non-sparking tools.
*[P243]: P243: Take precautionary measures to prevent static discharges.
*[P280]: P280: Wear protective gloves/protective clothing/eye protection/face protection.
*[P303+P361+P353]: P303+P361+P353: IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water [or shower].
*[P370+P378]: P370+P378: In case of fire: Use ... to extinguish.
*[P403+P235]: P403+P235: Store in a well ventilated place. Keep cool.
*[P501]: P501: Dispose of contents/container to ...
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