Citronellol

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Structural formula
Structural formulas of the citronellol enantiomers
( R ) -Citronellol (left) and ( S ) -Citronellol (right)
General
Surname Citronellol
other names
  • ( R ) -3,7-Dimethyloct-6-en-1-ol
  • ( S ) -3,7-Dimethyloct-6-en-1-ol
  • ( R ) -3,7-dimethyl-6-octen-1-ol
  • ( S ) -3,7-dimethyl-6-octen-1-ol
  • ( R ) -Citronellol
  • ( S ) -Citronellol
  • ( RS ) -Citronellol
  • rac -citronellol
  • (-) - β-Citronellol
  • (+) - β-citronellol
Molecular formula C 10 H 20 O
Brief description

colorless liquid with a rose-like odor

External identifiers / databases
CAS number
  • 106-22-9 [( RS ) -Citronellol]
  • 1117-61-9 [( R ) - (+) - Citronellol]
  • 7540-51-4 [( S ) - (-) - Citronellol]
EC number 203-375-0
ECHA InfoCard 100.003.069
PubChem 8842
ChemSpider 13850135
Wikidata Q27122080
properties
Molar mass 156.27 g mol −1
Physical state

liquid

density

0.86 g cm −3

Melting point

<-20 ° C

boiling point

224-224.5 ° C

Vapor pressure

<1 h Pa (20 ° C)

solubility

practically insoluble in water

Refractive index

1.462 (20 ° C)

safety instructions
GHS labeling of hazardous substances
07 - Warning 09 - Dangerous for the environment

Caution

H and P phrases H: 315-317-319-411
P: 261-273-280-302 + 352-305 + 351 + 338
Toxicological data

3450 mg 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

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

Rose 'Rose de Meaux'.
Lemongrass

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

  1. ↑ 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) .
  2. ↑ a b Entry on Citronellole. In: Römpp Online . Georg Thieme Verlag, accessed on June 17, 2014.
  3. ↑ Citronellol data sheet from Sigma-Aldrich , accessed on March 23, 2011 ( PDF ).
  4. ↑ Citronellol data sheet (PDF) from Merck , accessed on March 4, 2010.
  5. ↑ G. Ohloff: Fragrances: Signals of the Emotional World , Helvetica Chimica Acta, 2004, ISBN 978-3-90639030-7 , p. 53.
  6. ↑ a b alles-zur-allergologie.de: Citronellol .
  7. ^ 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.
  8. ↑ 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 .

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