6-methyl-5-hepten-2-one

Structural formula
General
Surname	6-methyl-5-hepten-2-one
other names	6-methylhept-5-en-2-one; Methyl isohexenyl ketone;
Molecular formula	C 8 H 14 O
Brief description	colorless liquid with a lemon-like odor
External identifiers / databases
EC number	203-816-7
ECHA InfoCard	100.003.470
PubChem	9862
Wikidata	Q3209146
properties
Molar mass	126.20 g mol −1
Physical state	liquid
density	0.85 g cm −3
Melting point	−67 ° C
boiling point	173 ° C
Vapor pressure	1 hPa (20 ° C)
solubility	sparingly soluble in water (3.02 g l −1 at 20 ° C); soluble in methanol and chloroform ;
Refractive index	1.439 (20 ° C)
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 226
	P: 210
Toxicological data	3500 mg kg −1 ( LD 50 , rat , oral ) ; > 5000 mg kg −1 ( LD 50 , 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

6-Methyl-5-hepten-2-one is a chemical compound from the group of ketones .

Occurrence

6-Methyl-5-hepten-2-one is one of the most important volatile flavors in tomatoes . The compound was originally identified in lemongrass but has been detected in the essential oils of palmarosa, lemons, verbena, geraniums, and others. It was also found in fruits (such as apples, apricots, sweet and sour cherries), but also in many other plant products (such as blueberries, cranberries, potatoes, ginger, cocoa, tea, star fruit, rice and others). Some species of bees release the compound, while others respond to the substance.

Extraction and presentation

6-Methyl-5-hepten-2-one can be obtained from lemongrass oil or citral in aqueous solution with potassium carbonate and subsequent distillation and vacuum fractionation or from acetoacetate and methyl-buten-3-ol-2 with aluminum alcoholate by Carroll's reaction followed by pyrolysis of the ester be won. Other synthetic methods are also known.

properties

6-methyl-5-hepten-2-one is a colorless liquid with a lemon-like odor that is sparingly soluble in water.

use

6-methyl-5-hepten-2-one can be used in the synthesis of thyrsiferyl 23-acetate, which acts as an antileukemic trigger of apoptosis . It is also used as a flavoring agent.

safety instructions

The vapors of 6-methyl-5-hepten-2-one can form an explosive mixture with air ( flash point 50 ° C, ignition temperature 250 ° C).

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m Entry on 6-methyl-5-hepten-2-one in the GESTIS substance database of the IFA , accessed on December 4, 2018(JavaScript required) .
↑ ^a ^b Data sheet 6-Methyl-5-hepten-2-one, 98% from AlfaAesar, accessed on December 4, 2018 ( PDF )(JavaScript required) .
↑ ^a ^b Data sheet 6-Methyl-5-hepten-2-one, natural, ≥98%, FCC from Sigma-Aldrich , accessed on December 4, 2018 ( PDF ).
^ Sandrine Mathieu, Valeriano Dal Cin et al. a .: Flavor compounds in tomato fruits: identification of loci and potential pathways affecting volatile composition. In: Journal of Experimental Botany. 60, 2009, p. 325, doi : 10.1093 / jxb / ern294 .
↑ ^a ^b ^c George A. Burdock: Fenaroli's Handbook of Flavor Ingredients . CRC Press, 2016, ISBN 978-1-4200-9086-4 , pp. 1284 ( limited preview in Google Book search).
^ Rainer Radtke: The Kleptoparasitic Neotropical Bee Lestrimelitta limao Behavior and chemical communication during raids on nests of other stingless bees . diplom.de, 1997, ISBN 3-8324-0545-3 , p. 88 ( limited preview in Google Book search).
↑ E. Breitmaier: Terpene flavors, fragrances, pharmaceuticals, pheromones . Springer-Verlag, 2013, ISBN 978-3-322-94727-7 , pp. 127 ( limited preview in Google Book search).
↑ Günther Ohloff: Fragrances and the sense of smell - The molecular world of fragrances . Springer-Verlag, 2013, ISBN 978-3-662-09768-7 , pp. 110 ( limited preview in Google Book search).
↑ Takashi NISHIDA, Yoshin TAMAI and a .: New Industrial Synthesis of 6-Methyl-5-hepten-2-one by Phase Transfer Reaction. In: Journal of Japan Oil Chemists' Society. 33, 1984, p. 606, doi : 10.5650 / jos1956.33.606 .

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m Entry on 6-methyl-5-hepten-2-one in the GESTIS substance database of the IFA , accessed on December 4, 2018(JavaScript required) .

[Alfa-2] Data sheet 6-Methyl-5-hepten-2-one, 98% from AlfaAesar, accessed on December 4, 2018 ( PDF )(JavaScript required) .

[Sigma-3] Data sheet 6-Methyl-5-hepten-2-one, natural, ≥98%, FCC from Sigma-Aldrich , accessed on December 4, 2018 ( PDF ).

[DOI10.1093/jxb/ern294-4] Sandrine Mathieu, Valeriano Dal Cin et al. a .: Flavor compounds in tomato fruits: identification of loci and potential pathways affecting volatile composition. In: Journal of Experimental Botany. 60, 2009, p. 325, doi : 10.1093 / jxb / ern294 .

[George_A._Burdock-5] George A. Burdock: Fenaroli's Handbook of Flavor Ingredients . CRC Press, 2016, ISBN 978-1-4200-9086-4 , pp. 1284 ( limited preview in Google Book search).

[Rainer_Radtke-6] Rainer Radtke: The Kleptoparasitic Neotropical Bee Lestrimelitta limao Behavior and chemical communication during raids on nests of other stingless bees . diplom.de, 1997, ISBN 3-8324-0545-3 , p. 88 ( limited preview in Google Book search).

[7] E. Breitmaier: Terpene flavors, fragrances, pharmaceuticals, pheromones . Springer-Verlag, 2013, ISBN 978-3-322-94727-7 , pp. 127 ( limited preview in Google Book search).

[Günther_Ohloff-8] Günther Ohloff: Fragrances and the sense of smell - The molecular world of fragrances . Springer-Verlag, 2013, ISBN 978-3-662-09768-7 , pp. 110 ( limited preview in Google Book search).

[DOI10.5650/jos1956.33.606-9] Takashi NISHIDA, Yoshin TAMAI and a .: New Industrial Synthesis of 6-Methyl-5-hepten-2-one by Phase Transfer Reaction. In: Journal of Japan Oil Chemists' Society. 33, 1984, p. 606, doi : 10.5650 / jos1956.33.606 .