cis -3-hexenol
Structural formula | |||||||||||||||||||
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General | |||||||||||||||||||
Surname | cis -3-hexenol | ||||||||||||||||||
other names |
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Molecular formula | C 6 H 12 O | ||||||||||||||||||
Brief description |
colorless liquid with a pleasant odor |
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properties | |||||||||||||||||||
Molar mass | 100.16 g mol −1 | ||||||||||||||||||
Physical state |
liquid |
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density |
0.847 g cm −3 |
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Melting point |
−61 ° C |
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boiling point |
156.5 ° C |
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solubility |
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Refractive index |
1.4380 (20 ° C) |
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safety instructions | |||||||||||||||||||
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Toxicological data | |||||||||||||||||||
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
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.
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
- ↑ 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) .
- ↑ 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.
- ↑ Data sheet Cis-3-Hexenol (PDF) from Merck , accessed on January 18, 2011.
- ↑ a b Food and Cosmetics Toxicology . Vol. 7, 1969, p. 451.
- ↑ a b c Entry on cis-3-hexenol in the ChemIDplus database of the United States National Library of Medicine (NLM) .
- ↑ a b Food and Cosmetics Toxicology. Vol. 12, 1974, p. 909.
- ↑ 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 .
- ↑ 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.
- ↑ US Patent 3962354 .
- ↑ chemistryworld.de .