Hex-3-enyl acetate

Structural formula
	Structural formula of cis -hex-3-ene acetate
General
Surname	Hex-3-enyl acetate
other names	cis -3-hexen-1-yl acetate; cis -Hex-3-enyl acetate; ( Z ) -Hex-3-enyl acetate;
Molecular formula	C 8 H 14 O 2
Brief description	colorless to yellowish liquid with a fruity odor
External identifiers / databases
EC number	222-960-1
ECHA InfoCard	100.020.873
PubChem	5363388
Wikidata	Q1368869
properties
Molar mass	142.19 g mol −1
Physical state	liquid
density	0.90 g cm −3 (25 ° C)
boiling point	171.6 ° C (1018 h Pa )
solubility	heavy in water (1.11 g l −1 at 20 ° C); very soluble in ethanol ;
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 226
	P: 210-233-303 + 361 + 353-370 + 378-403 + 235-501
Toxicological data	> 5 g kg −1 ( LD 50 , rabbit , transdermal ) ; > 5 g kg −1 ( LD 50 , rat , oral ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Acetic acid hex-3-enyl ester , also 3-hexenyl acetate , is a chemical compound from the group of unsaturated carboxylic acid esters and green leaf fragrances .

Occurrence, properties and use

Strawberry "Mieze Schindler".

The ester is found in the leaves and berries of many plants (such as strawberry, apple, apricot, tea leaves, and tomato). The substance is released from plants - in addition to cis -3-hexenol - after tissue damage to kill fungi ( fungicide ) and bacteria ( bactericide ) and as a defense against herbivorous animals, mostly insects.

The colorless liquid, which smells strongly of green fruits, is used in industry - often mixed with the "leaf alcohol" cis -3-hexenol - as a flavor and fragrance . The odor threshold in humans is 7.8 μg / kg. The flavor is industrially produced by the acid-catalyzed esterification of acetic acid and cis -3-hexenol.

safety instructions

The toxicity of acetic acid hex-3-ene ester in animal experiments with rabbits and rats was low: the LD ₅₀ values dermal and oral were> 5 g / kg body weight. In the US , the FEMA P ADI is 2.9 mg / day.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f Entry on (Z) -Hex-3-enyl acetate in the GESTIS substance database of the IFA , accessed on January 10, 2017(JavaScript required) .
↑ ^a ^b ^c ^d George A. Burdock: Fenaroli's handbook of flavor ingredients. 5th edition, CRC Press, 2005, ISBN 978-0-8493-3034-6 , p. 800.
↑ ^a ^b ^c Food and Cosmetics Toxicology , Vol. 13, 1975, p. 454.
↑ ^a ^b ^c Entry on hex-3-enyl acetate in the ChemIDplus database of the United States National Library of Medicine (NLM) .
↑ Lebensmittel-Lexikon, Waldemar Ternes, ISBN 978-3-89947-165-6 ( limited preview in the Google book search).
↑ Horst Surburg, Johannes Panten: Common fragrance and flavor materials: preparation, properties and uses. 5th edition, Wiley-VCH, 2006, ISBN 978-3-527-31315-0 , p. 21.
↑ John D'Auria: How the formation of green leaf fragrances is controlled. (PDF; 9.9 MB) Max Planck Institute for Chemical Ecology , Jena.
↑ Hans-Dieter Belitz: Textbook of food chemistry. Springer-Verlag, 2008, ISBN 978-3-540-73202-0 , p. 388 ( limited preview in the Google book search).

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f Entry on (Z) -Hex-3-enyl acetate in the GESTIS substance database of the IFA , accessed on January 10, 2017(JavaScript required) .

[fenaroli-2] George A. Burdock: Fenaroli's handbook of flavor ingredients. 5th edition, CRC Press, 2005, ISBN 978-0-8493-3034-6 , p. 800.

[fact-3] Food and Cosmetics Toxicology , Vol. 13, 1975, p. 454.

[chemid-4] Entry on hex-3-enyl acetate in the ChemIDplus database of the United States National Library of Medicine (NLM) .

[5] Lebensmittel-Lexikon, Waldemar Ternes, ISBN 978-3-89947-165-6 ( limited preview in the Google book search).

[6] Horst Surburg, Johannes Panten: Common fragrance and flavor materials: preparation, properties and uses. 5th edition, Wiley-VCH, 2006, ISBN 978-3-527-31315-0 , p. 21.

[dauria-7] John D'Auria: How the formation of green leaf fragrances is controlled. (PDF; 9.9 MB) Max Planck Institute for Chemical Ecology , Jena.

[8] Hans-Dieter Belitz: Textbook of food chemistry. Springer-Verlag, 2008, ISBN 978-3-540-73202-0 , p. 388 ( limited preview in the Google book search).