Citronellol

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Citronellol

(+)-Citronellol (left) and (-)-citronellol
IUPAC name

3,7-Dimethyloct-6-en-1-ol

Other names

(±)-β-Citronellol;
3,7-Dimethyl-6-octen-1-ol

Identifiers
CAS number 106-22-9 YesY
ChemSpider 13850135 YesY
UNII P01OUT964K YesY
KEGG C09849 YesY
ChEBI CHEBI:50462 YesY
ChEMBL CHEMBL395827 YesY
Jmol-3D images {{#if:OCC[C@@H](CC/C=C(/C)C)CC\C(C)=C\CCC(C)CCO|Image 1
Image 2
Properties
Molecular formula C10H20O
Molar mass 156.27 g mol−1
Density 0.855 g/cm3
Boiling point 225 °C; 437 °F; 498 K
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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.

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,[8] as some people may become sensitised to it, but the degree to which citronellol can cause an allergic reaction in humans is disputed.[9][10]

See also

References

  1. ↑ Lawless, J. The Illustrated Encyclopedia of Essential Oils. ISBN 1-85230-661-0. 
  2. ↑ Robert H. Morris (2007). "Ruthenium and Osmium". In J. G. de Vries and C. J. Elsevier. The Handbook of Homogeneous Hydrogenation. Weinheim: WILEY-VCH. ISBN 978-3-527-31161-3. 
  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. 
  4. ↑ 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. 
  5. ↑ 5.0 5.1 US EPA Citronellol Fact Sheet
  6. ↑ Revay, Edita E.; Kline, Daniel L.; Xue, Rui-De; Qualls, Whitney A.; Bernier, Ulrich R.; Kravchenko, Vasiliy D.; Ghattas, Nina; Pstygo, Irina et al. (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. 
  7. ↑ 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. 
  8. ↑ http://www.ifraorg.org/en-us/standards_restricted/s3/p3
  9. ↑ Cropwatch Report April 2008
  10. ↑ Survey and health assessment of chemical substances in massage oils
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