cis -3-hexenol

Structural formula
General
Surname	cis -3-hexenol
other names	( Z ) -3-hexen-1-ol ( IUPAC ) Leaf alcohol cis -hex-3-en-1-ol
Molecular formula	C 6 H 12 O
Brief description	colorless liquid with a pleasant odor
External identifiers / databases
CAS number 928-96-1 EC number 213-192-8 ECHA InfoCard 100.011.994 PubChem 5281167 ChemSpider 21105914 Wikidata Q300850
properties
Molar mass	100.16 g mol −1
Physical state	liquid
density	0.847 g cm −3
Melting point	−61 ° C
boiling point	156.5 ° C
solubility	soluble in water (19.3 g l −1 at 20 ° C) easily soluble in ethanol
Refractive index	1.4380 (20 ° C)
safety instructions
GHS labeling of hazardous substances Caution H and P phrases H: 226-319 P: 210-280-264-337 + 313
Toxicological data	7 g kg −1 ( LD 50 ,  mouse ,  oral ) 4.7 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 . Refractive index: Na-D line , 20 ° C

cis -3-hexenol or leaf alcohol is a naturally occurring chemical compound from the group of unsaturated alcohols . The oily liquid smells strongly of freshly cut grass and is one of the green leaf fragrances .

Occurrence

Grape with berries of a white grape variety

cis -3-Hexenol occurs in the blossoms and leaves of various flowers (e.g. tulips), fruits (e.g. apples, bananas, grapes, pineapples) and in the leaves of the tea plant . The ester with acetic acid , hex-3-enyl acetate , is also found in many plants.

Extraction and synthesis

cis -3-Hexenol is obtained by extraction from plants and fruits or is produced synthetically.

The synthesis takes place from alkoxyphenols by hydrogenation , ring opening by ozonolysis and subsequent reduction to alcohol.

Preparation of cis -3-hexenol

properties

cis -3-Hexenol is a colorless, oily liquid that dissolves little in water, but dissolves well in ethanol. The scent is already perceived at a concentration of 70  ppb ; a clear odor of green fruits occurs from around 30  ppm . The oral toxicity is low: in animal experiments with mice and rats, LD ₅₀ values ​​of 4.7 g / kg (rat) and 7 g / kg (mouse) were determined.

use

cis -3-hexenol is used as a fragrance in tea, perfume (e.g. from the scent of violets) and foods and as a starting material for the synthesis of 2- trans -6- cis -nonadien-1-ol, 2- trans -6- cis -Nonadien-1-al and hex-3-enyl acetate used.

In many plants - in addition to hex-3-enyl acetate - the substance is released after tissue damage to kill fungi ( fungicide ) and bacteria ( bactericide ) and as a defense against herbivorous animals, mostly insects.

Individual evidence

1. ↑ ^{a b c d e} Entry on cis-Hex-3-en-1-ol in the GESTIS substance database of the IFA , accessed on January 10, 2017(JavaScript required) .
2. ↑ ^{a b c d e} David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-284.
3. ↑ Data sheet Cis-3-Hexenol (PDF) from Merck , accessed on January 18, 2011.
4. ↑ ^{a b} Food and Cosmetics Toxicology . Vol. 7, 1969, p. 451.
5. ↑ ^{a b c} Entry on cis-3-hexenol in the ChemIDplus database of the United States National Library of Medicine (NLM) .
6. ↑ ^{a b} Food and Cosmetics Toxicology. Vol. 12, 1974, p. 909.
7. ↑ ^{a b} John D'Auria: The world of natural substances: Investigations of ester compounds and acyltransferases on the model system Arabidopsis thaliana. (PDF; 9.9 MB) In: Max Planck Institute for Chemical Ecology , Jena: Activity Report 2008 .
8. ↑ ^{a b c} George A. Burdock: Fenaroli's handbook of flavor ingredients. 5th edition, CRC Press, 2005, ISBN 978-0-8493-3034-6 , pp. 797-798.
9. ↑ US Patent 3962354 .
10. ↑ chemistryworld.de .