Citronellol
Structural formula | |||||||||||||||||||
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( R ) -Citronellol (left) and ( S ) -Citronellol (right) | |||||||||||||||||||
General | |||||||||||||||||||
Surname | Citronellol | ||||||||||||||||||
other names |
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Molecular formula | C 10 H 20 O | ||||||||||||||||||
Brief description |
colorless liquid with a rose-like odor |
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External identifiers / databases | |||||||||||||||||||
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properties | |||||||||||||||||||
Molar mass | 156.27 g mol −1 | ||||||||||||||||||
Physical state |
liquid |
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density |
0.86 g cm −3 |
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Melting point |
<-20 ° C |
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boiling point |
224-224.5 ° C |
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Vapor pressure |
<1 h Pa (20 ° C) |
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solubility |
practically insoluble in water |
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Refractive index |
1.462 (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 |
Citronellol , 3,7-dimethyloct-6-en-1-ol, is an acyclic terpinol with the empirical formula C 10 H 20 O and is an isomer of rhodinol . The compound contains a stereocenter so that two enantiomers exist. They appear as colorless to light yellow liquids that differ in terms of smell. ( R ) -Citronellol has the smell of citronell oil , ( S ) -Citronellol smells like geranium oil .
Occurrence
Both enantiomers occur in nature. ( S ) -Citronellol is a natural component of rose and geranium oils . ( R ) -Citronellol occurs in citronella oils made from lemongrass .
Presentation and extraction
An early synthesis starts from citral from which by means of platinum catalysis is reduced.
properties
It is a liquid that boils at 109–111 ° C at a pressure of 13 hPa. Their density is 0.86 grams per cubic centimeter. It is insoluble in water and can be mixed with alcohol . The flash point is 107 ° C, the ignition temperature 240 ° C. The partial oxidation of the primary alcohol ( R ) -citronellol leads to the terpene ( R ) - Citronellal , an aldehyde .
use
Citronellol is used as a fragrance in deodorant products, detergents and mosquito repellants. It is since 1954 a fragrant decisive part of the Czech aftershave Pitralon F - voda po holení produced in unchanged composition until today.
safety instructions
Citronellol is irritant and dangerous for the environment. The oral LD 50 value for a rat is 3450 milligrams per kilogram of body weight.
See also
Individual evidence
- ↑ a b c d e f g h Entry on citronellol in the GESTIS substance database of the IFA , accessed on January 10, 2017(JavaScript required) .
- ↑ a b Entry on Citronellole. In: Römpp Online . Georg Thieme Verlag, accessed on June 17, 2014.
- ↑ Citronellol data sheet from Sigma-Aldrich , accessed on March 23, 2011 ( PDF ).
- ↑ Citronellol data sheet (PDF) from Merck , accessed on March 4, 2010.
- ↑ G. Ohloff: Fragrances: Signals of the Emotional World , Helvetica Chimica Acta, 2004, ISBN 978-3-90639030-7 , p. 53.
- ↑ a b alles-zur-allergologie.de: Citronellol .
- ^ Adams, R., and Garvey, BS: Selective reduction of citral by means of platinum-oxide platinum black and a promoter in J. Am. Chem. Soc. 48 (1926) 477-482.
- ↑ Juliane Daphi-Weber, Heike Raddatz, Rainer Müller: Investigation of Fragrances - Controlled Fragrances , pp. 94–95, in Volume V of the series HighChem hautnah - News from food chemistry (published by the Society of German Chemists ) 2010, ISBN 978- 3-936028-64-5 .
Web links
- Joint FAO / WHO Expert Committee on Food Additives (JECFA), Monograph for Citronellol
- EPA factsheet