Citronellol
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
- ^ Lawless, J. The Illustrated Encyclopedia of Essential Oils. ISBN 1-85230-661-0.
- ^ Robert H. Morris (2007). "Ruthenium and Osmium". In J. G. de Vries and C. J. Elsevier (ed.). The Handbook of Homogeneous Hydrogenation. Weinheim: WILEY-VCH. ISBN 978-3-527-31161-3.
- ^ Ait Ali, M; Allaoud, S; Karim, A; Roucoux, A; Mortreux, A (1995). "Catalytic Synthesis of (R) and (S) citronellol by homogeneous hydrogenation over amidophosphinephosphinite and diaminodiphosphine rhodium complexes". Tetrahedron: Asymmetry. 6 (2): 369. doi:10.1016/0957-4166(95)00015-H.
- ^ Taylor WG, Schreck CE. (1985). "Chiral-phase capillary gas chromatography and mosquito repellent activity of some oxazolidine derivatives of (+)- and (−)-citronellol". J Pharm Sci. 74 (5): 534–539. doi:10.1002/jps.2600740508. PMID 2862274.
- ^ a b "Redirect". epa.gov. Retrieved 29 July 2015.
- ^ Revay, Edita E.; Kline, Daniel L.; Xue, Rui-De; Qualls, Whitney A.; Bernier, Ulrich R.; Kravchenko, Vasiliy D.; Ghattas, Nina; Pstygo, Irina; Müller, Günter C. (2013). "Reduction of mosquito biting-pressure: Spatial repellents or mosquito traps? A field comparison of seven commercially available products in Israel". Acta Tropica. 127 (1): 63–8. doi:10.1016/j.actatropica.2013.03.011. PMID 23545129.
- ^ Songkro, Sarunyoo; Hayook, Narissara; Jaisawang, Jittarat; Maneenuan, Duangkhae; Chuchome, Thitima; Kaewnopparat, Nattha (2011). "Investigation of inclusion complexes of citronella oil, citronellal and citronellol with β-cyclodextrin for mosquito repellent". Journal of Inclusion Phenomena and Macrocyclic Chemistry. 72 (3–4): 339. doi:10.1007/s10847-011-9985-7.
- ^ ""Dark" Singlet Oxygenation of β-Citronellol: A Key Step in the Manufacture of Rose Oxide". Organic Process Research & Development.
- ^ http://www.ifraorg.org/en-us/standards_restricted/s3/p3
- ^ Cropwatch Report April 2008
- ^ Survey and health assessment of chemical substances in massage oils