Citronellol
(+)-Citronellol (left) and (−)-citronellol (right)
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R-(+)-Citronellol
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S-(−)-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; Cephrol, Corol
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Identifiers | |
3D model (
JSmol ) |
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1362474 | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard
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100.003.069 |
EC Number |
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KEGG | |
PubChem CID
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UNII |
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CompTox Dashboard (EPA)
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Properties | |
C10H20O | |
Molar mass | 156.269 g·mol−1 |
Density | 0.855 g/cm3 |
Boiling point | 225 °C (437 °F; 498 K) |
Viscosity | 11.1 mPa s |
Hazards | |
GHS labelling: | |
Warning | |
H315, H317, H319 | |
P261, P264, P272, P273, P280, P302+P352, P305+P351+P338, P321, P332+P313, P333+P313, P337+P313, P362, P363, P391, P501 | |
NFPA 704 (fire diamond) | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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 widespread, but particularly abundant in the oils of rose (18–55%) and Pelargonium geraniums.[1]
Preparation
Several million kilograms of citronellol are produced annually. It is mainly obtained by hydrogenation of geraniol or nerol over copper chromite catalyst.[2] Homogeneous catalysts are used for the production of enantiomers.[3][4]
Uses
Citronellol is used in perfumes and as a fragrance in cleaning products. In many applications, one of the enantiomers is preferred. It is a component of citronella oil, an insect repellant.[2]
Citronellol is used as a raw material for the production of rose oxide.[2][5] It is also a precursor to many commercial and potential fragrances such as citronellol acetate, citronellyl oxyacetaldehyde, citronellyl methyl acetal, and ethyl citronellyl oxalate.[2]
Health and safety
The United States FDA considers citronellol as generally recognized as safe (GRAS) for food use.[6] Citronellol is subject to restrictions on its use in perfumery,[7] as some people may become sensitised to it, but the degree to which citronellol can cause an allergic reaction in humans is disputed.[8][9]
In terms of dermal safety, citronellol has been evaluated as an insect repellent.[10]
See also
References
- ISBN 978-1-85230-661-8.
- ^ ISBN 0471238961.
- ISBN 978-3-527-31161-3.
- .
- .
- ^ "Redirect". epa.gov. Retrieved 29 July 2015.
- ^ "Standards Restricted - IFRA International Fragrance Association". Archived from the original on 6 January 2012. Retrieved 19 July 2012.
- ^ "Cropwatch Report April 2008" (PDF). Archived from the original (PDF) on 10 February 2014. Retrieved 19 July 2012.
- ^ Survey and health assessment of chemical substances in massage oils Archived 27 September 2007 at the Wayback Machine
- PMID 2862274.