Isopentyl acetate

Structural formula
General
Surname	Isopentyl acetate
other names	Acetic acid (3-methylbutyl) ester; 3-methylbutyl acetate; Isoamyl acetate; i -amylacetate; Pear oil; Pear ether; i -pentyl acetate; 3-methyl-1-butyl acetate; ISOAMYL ACETATE ( INCI ) ;
Molecular formula	C 7 H 14 O 2
Brief description	Not very volatile, colorless liquid with a fruity / banana-like odor
External identifiers / databases
EC number	204-662-3
ECHA InfoCard	100.004.240
PubChem	31276
Wikidata	Q221307
properties
Molar mass	130.19 g mol −1
Physical state	liquid
density	0.87 g cm −3
Melting point	−79 ° C
boiling point	142 ° C
Vapor pressure	5.3 h Pa (20 ° C); 10 hPa (30 ° C); 33 hPa (50 ° C);
solubility	slightly soluble in water (2.12 g l −1 at 19.4 ° C)
Refractive index	1,400 (20 ° C)
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 226
	EUH: 066
	P: 210
Toxicological data	> 5000 mg kg −1 ( LD 50 , rabbit , transdermal ) ; 16.600 mg · kg -1 ( LD 50 , rat , orally ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Isopentyl acetate is a chemical compound from the group of carboxylic acid esters , more precisely pentyl acetate .

Occurrence

Isopentyl acetate is one of the main components of banana flavor and an important flavoring agent in beer . It has also been detected as a flavoring substance in a variety of other fruits and other foods, especially fermented drinks. Bees release the compound before an attack, so it's an alarm pheromone.

Extraction and presentation

Isopentyl acetate ( 2 ) can be obtained by esterifying isoamyl alcohol ( 1 ) with acetic acid:

This acid-catalyzed equilibrium reaction can be shifted to the side of the ester 2 in that the water formed is removed from the reaction mixture.

properties

Isopentyl acetate is a slightly volatile, flammable, colorless liquid with a fruity odor that is sparingly soluble in water.

Safety-related parameters

Isopentyl acetate forms highly flammable vapor-air mixtures. The compound has a flash point of 35 ° C. The explosion range is between 1% by volume (53 g / m ³ ) as the lower explosion limit (LEL) and 9% by volume (485 g / m ³ ) as the upper explosion limit (UEL). The lower explosion point is 33 ° C. The ignition temperature is 380 ° C. The substance therefore falls into temperature class T2.

use

Isopentyl acetate is used as a banana aroma because of its banana smell. In the past, the Hefner candle was used as a light standard, using iso-amyl acetate = isopentyl acetate or a mixture of pentyl ester of acetic acid as fuel. In addition, because of its strong smell, it is also used for leak testing of military gas protective masks.

Individual evidence

↑ Entry on ISOAMYL ACETATE in the CosIng database of the EU Commission, accessed on March 21, 2020.
↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ ^o ^p ^q ^r Entry for CAS no. 123-92-2 in the GESTIS substance database of the IFA , accessed on September 21, 2018(JavaScript required) .
↑ Data sheet Isoamyl acetate, natural, ≥97%, FCC, FG from Sigma-Aldrich , accessed on September 20, 2015 ( PDF ).
^ Marshall J. Myers, Phillip Issenberg, Emily L. Wick: l-Leucine as a precursor of isoamyl alcohol and isoamyl acetate, volatile aroma constituents of banana fruit discs. In: Phytochemistry. 9, 1970, p. 1693, doi : 10.1016 / S0031-9422 (00) 85580-6 .
↑ Prof. Dr. Werner Back: Microbiology of Food Volume 5: Beverages . Behr's Verlag DE, 2008, ISBN 978-3-89947-956-0 , p. 144 ( limited preview in Google Book search).
↑ Entry on isopentyl acetate. In: Römpp Online . Georg Thieme Verlag, accessed on September 21, 2015.
↑ ^a ^b Jeff Potter: Cooking for Geeks Inspiration & Innovation for the Kitchen; [Recipes and Scientific Adventures] . O'Reilly Germany, 2011, ISBN 978-3-86899-125-3 , pp. 96 ( limited preview in Google Book search).
^ Hermann Sahm, Garabed Antranikian, Klaus-Peter Stahmann, Ralf Takors: Industrial microbiology . Springer-Verlag, 2014, ISBN 978-3-8274-3040-3 , pp. 265 ( limited preview in Google Book search).
^ ^A ^b E. Brandes, W. Möller: Safety-related parameters - Volume 1: Flammable liquids and gases , Wirtschaftsverlag NW - Verlag für neue Wissenschaft GmbH, Bremerhaven 2003.
↑ H. Lux, Modern Lighting, accessed on November 28, 2018.
^ Occupational Safety and Health Administration: Fit Testing Procedures (Mandatory). - 1910.134 App A | Occupational Safety and Health Administration , accessed January 17, 2020.

[CosIng-1] Entry on ISOAMYL ACETATE in the CosIng database of the EU Commission, accessed on March 21, 2020.

[GESTIS-2] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ ^o ^p ^q ^r Entry for CAS no. 123-92-2 in the GESTIS substance database of the IFA , accessed on September 21, 2018(JavaScript required) .

[Sigma-3] Data sheet Isoamyl acetate, natural, ≥97%, FCC, FG from Sigma-Aldrich , accessed on September 20, 2015 ( PDF ).

[DOI10.1016/S0031-9422(00)85580-6-4] Marshall J. Myers, Phillip Issenberg, Emily L. Wick: l-Leucine as a precursor of isoamyl alcohol and isoamyl acetate, volatile aroma constituents of banana fruit discs. In: Phytochemistry. 9, 1970, p. 1693, doi : 10.1016 / S0031-9422 (00) 85580-6 .

[Back-5] Prof. Dr. Werner Back: Microbiology of Food Volume 5: Beverages . Behr's Verlag DE, 2008, ISBN 978-3-89947-956-0 , p. 144 ( limited preview in Google Book search).

[RömppOnline-6] Entry on isopentyl acetate. In: Römpp Online . Georg Thieme Verlag, accessed on September 21, 2015.

[Potter-7] Jeff Potter: Cooking for Geeks Inspiration & Innovation for the Kitchen; [Recipes and Scientific Adventures] . O'Reilly Germany, 2011, ISBN 978-3-86899-125-3 , pp. 96 ( limited preview in Google Book search).

[indmb-8] Hermann Sahm, Garabed Antranikian, Klaus-Peter Stahmann, Ralf Takors: Industrial microbiology . Springer-Verlag, 2014, ISBN 978-3-8274-3040-3 , pp. 265 ( limited preview in Google Book search).

[Brandes-9] A ^b E. Brandes, W. Möller: Safety-related parameters - Volume 1: Flammable liquids and gases , Wirtschaftsverlag NW - Verlag für neue Wissenschaft GmbH, Bremerhaven 2003.

[10] H. Lux, Modern Lighting, accessed on November 28, 2018.

[osha.gov-11] Occupational Safety and Health Administration: Fit Testing Procedures (Mandatory). - 1910.134 App A | Occupational Safety and Health Administration , accessed January 17, 2020.