Citronellol
Skeletal formula of (+)-citronellol and (−)-citronellol (+)-Citronellol (left) and (−)-citronellol (right)
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Ball-and-stick model of the (+)-citronellol molecule (+)-Citronellol
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Ball-and-stick model of the (-)-citronellol molecule (-)-Citronellol
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Names | |
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IUPAC name
3,7-Dimethyloct-6-en-1-ol
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Other names
(±)-β-Citronellol;
3,7-Dimethyl-6-octen-1-ol |
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Identifiers | |
106-22-9 | |
ChEBI | CHEBI:50462 |
ChEMBL | ChEMBL395827 |
ChemSpider | 13850135 |
Jmol 3D model | Interactive image Interactive image |
KEGG | C09849 |
UNII | P01OUT964K |
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Properties | |
C10H20O | |
Molar mass | 156.27 g·mol−1 |
Density | 0.855 g/cm3 |
Boiling point | 225 °C (437 °F; 498 K) |
Vapor pressure | {{{value}}} |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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verify (what is ?) | |
Infobox references | |
Citronellol, or dihydrogeraniol, is a natural acyclic monoterpenoid. Both enantiomers occur in nature. (+)-Citronellol, which is found in citronella oils, including Cymbopogon nardus (50%), is the more common isomer. (−)-Citronellol is found in the oils of rose (18-55%) and Pelargonium geraniums.[1]
Preparation
Citronellol can be prepared by hydrogenation of geraniol or nerol.[2][3]
Uses
Citronellol is used in perfumes and insect repellents,[4] and as a mite attractant.[5] Citronellol is a good mosquito repellent at short distances, but protection greatly lessens when the subject is slightly further from the source.[6] When complexed with β-cyclodextrin, it has on average a 1.5 hour protection duration against mosquitoes.[7]
Citronellol is used as a raw material for the production of rose oxide.[8]
Health and safety
The United States FDA considers citronellol as generally recognized as safe (GRAS) for food use.[5] Citronellol is subject to restrictions on its use in perfumery,[9] as some people may become sensitised to it, but the degree to which citronellol can cause an allergic reaction in humans is disputed.[10][11]
See also
References
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- ↑ http://www.ifraorg.org/en-us/standards_restricted/s3/p3
- ↑ Cropwatch Report April 2008
- ↑ Survey and health assessment of chemical substances in massage oils