3-octanone

Structural formula
General
Surname	3-octanone
other names	Ethyl pentyl ketone; Amyl ethyl ketone; Octan-3-one; EAK; Ethyl n -amylketon;
Molecular formula	C 8 H 16 O
Brief description	colorless liquid with a mild fruity odor
External identifiers / databases
EC number	203-423-0
ECHA InfoCard	100.003.113
PubChem	246728
Wikidata	Q18349104
properties
Molar mass	128.21 g mol −1
Physical state	liquid
density	0.82 g cm −3
Melting point	−23 ° C
boiling point	169 ° C
Vapor pressure	2.11 mbar (20 ° C)
solubility	sparingly soluble in water (4.5 g l −1 at 20 ° C); soluble in ethanol; soluble in most common solvents;
Refractive index	1.415 (20 ° C)
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 226
	P: 210-370 + 378
Toxicological data	> 3500 mg kg −1 ( LD 50 , rat , oral ) ; > 5000 mg kg −1 ( LD 50 , mouse / rabbit , transdermal ) ;
	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

3-Octanone is a chemical compound from the group of dialkyl ketones .

Occurrence

lavender

3-Octanone occurs naturally in various plants such as lavender , rosemary, and nectarines . The compound is also produced by fungi and is therefore classified as a secondary indicator in the room air for mold infestation . Certain ants such as the red garden ant ( Myrmica rubra ) also synthesize 3-octanone.

Extraction and presentation

3-Octanone can be obtained by heating propionic acid and caproic acid over thorium (IV) oxide or by oxidizing ethyl amyl ketone carbinol .

properties

3-Octanone is a slightly volatile, flammable, colorless liquid with a mild fruity odor that is sparingly soluble in water. It decomposes when heated, producing, among other things, carbon monoxide and carbon dioxide .

use

3-octanone is used as a flavoring agent.

safety instructions

The vapors of 3-octanone can form an explosive mixture with air ( flash point 53 ° C, ignition temperature 330 ° C).

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l Entry on 3-octanone in the GESTIS substance database of the IFA , accessed on January 9, 2019(JavaScript required) .
↑ ^a ^b Giovanni Fenaroli: Fenaroli's Handbook of Flavor Ingredients: . Taylor & Francis, 1971, ISBN 978-0-87819-533-6 , pp. 917 ( limited preview in Google Book search).
↑ ^a ^b Data sheet 3-octanone (PDF) from Merck , accessed on May 3, 2015.
^ Opdyke, DLJ (ed.): Monographs on Fragrance Raw Materials . Pergamon Press, New York 1979, p. 346.
↑ Koedam, A .: Freshly Distilled Oil of the Leaves of Rasmarinus Officianalis L Contained 3-Octanone. In: Journal of Nature Research C . 33, 1978, pp. 144-145 ( online ).
↑ Takeoka GR: Nectarine volatiles: vacuum steam distillation versus headspace sampling . In: J Agric Food Chem . 36, No. 3, 1988, pp. 553-560. doi : 10.1021 / jf00081a037 .
^ AL Sunesson, CA Nilsson, B. Andersson, G. Blomquist: Volatile metabolites produced by two fungal species cultivated on building materials. In: Ann Occup Hyg. 40, 1996, pp. 397-410, PMID 8806212 .
↑ Jasmine Wallner: mold Beagle and laboratory analysis: . vdf Hochschulverlag AG, 2013, ISBN 978-3-7281-3459-2 , p. 37 ( limited preview in Google Book search).
↑ Gerhard Andreas Wiesmüller, Thomas Eikmann, Birger Heinzow, Guido Fischer, Caroline Lord, Thomas Gabrio, Regine Szewzyk: health hazard mold in the interior: . Hüthig Jehle Rehm, 2013, ISBN 978-3-609-16464-9 , pp. 302 ( limited preview in Google Book search).
↑ M.-C. Cammaerts-Tricot: Production and perception of attractive pheromones by differently aged workers of Myrmica rubra (Hymenoptera Formicidae). In: Insectes Sociaux. 21, 1974, p. 235, doi : 10.1007 / BF02226916 .
^ Entry on 3-octanone in the Hazardous Substances Data Bank , accessed May 3, 2015.
^ Ashford RD: Ashford's Dictionary of Industrial Chemicals . Wavelength Publications Ltd, London, England 1994, p. 389.
^ Code of Federal Regulations Title 21

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l Entry on 3-octanone in the GESTIS substance database of the IFA , accessed on January 9, 2019(JavaScript required) .

[Giovanni_Fenaroli-2] Giovanni Fenaroli: Fenaroli's Handbook of Flavor Ingredients: . Taylor & Francis, 1971, ISBN 978-0-87819-533-6 , pp. 917 ( limited preview in Google Book search).

[Merck-3] Data sheet 3-octanone (PDF) from Merck , accessed on May 3, 2015.

[4] Opdyke, DLJ (ed.): Monographs on Fragrance Raw Materials . Pergamon Press, New York 1979, p. 346.

[5] Koedam, A .: Freshly Distilled Oil of the Leaves of Rasmarinus Officianalis L Contained 3-Octanone. In: Journal of Nature Research C . 33, 1978, pp. 144-145 ( online ).

[6] Takeoka GR: Nectarine volatiles: vacuum steam distillation versus headspace sampling . In: J Agric Food Chem . 36, No. 3, 1988, pp. 553-560. doi : 10.1021 / jf00081a037 .

[PMID8806212-7] AL Sunesson, CA Nilsson, B. Andersson, G. Blomquist: Volatile metabolites produced by two fungal species cultivated on building materials. In: Ann Occup Hyg. 40, 1996, pp. 397-410, PMID 8806212 .

[Jasmin_Wallner-8] Jasmine Wallner: mold Beagle and laboratory analysis: . vdf Hochschulverlag AG, 2013, ISBN 978-3-7281-3459-2 , p. 37 ( limited preview in Google Book search).

[Gerhard_Andreas_Wiesmüller,_Thomas_Eikmann,_Birger_Heinzow,_Guido_Fischer,_Caroline_Herr,_Thomas_Gabrio,_Regine_Szewzyk-9] Gerhard Andreas Wiesmüller, Thomas Eikmann, Birger Heinzow, Guido Fischer, Caroline Lord, Thomas Gabrio, Regine Szewzyk: health hazard mold in the interior: . Hüthig Jehle Rehm, 2013, ISBN 978-3-609-16464-9 , pp. 302 ( limited preview in Google Book search).

[DOI10.1007/BF02226916-10] M.-C. Cammaerts-Tricot: Production and perception of attractive pheromones by differently aged workers of Myrmica rubra (Hymenoptera Formicidae). In: Insectes Sociaux. 21, 1974, p. 235, doi : 10.1007 / BF02226916 .

[HSDB-11] Entry on 3-octanone in the Hazardous Substances Data Bank , accessed May 3, 2015.

[12] Ashford RD: Ashford's Dictionary of Industrial Chemicals . Wavelength Publications Ltd, London, England 1994, p. 389.

[13] Code of Federal Regulations Title 21