Citronellol

Not to be confused with Citronellal.
Citronellol
Skeletal formula of (+)-citronellol and (−)-citronellol
(+)-Citronellol (left) and (−)-citronellol (right)
Ball-and-stick model of the (+)-citronellol molecule
(+)-Citronellol
Ball-and-stick model of the (-)-citronellol molecule
(-)-Citronellol
Names
IUPAC name
3,7-Dimethyloct-6-en-1-ol
Other names
(±)-β-Citronellol;
3,7-Dimethyl-6-octen-1-ol
Identifiers
106-22-9 YesY
3D model (Jmol) Interactive image
Interactive image
ChEBI CHEBI:50462 YesY
ChEMBL ChEMBL395827 YesY
ChemSpider 13850135 YesY
ECHA InfoCard 100.012.955
KEGG C09849 YesY
UNII P01OUT964K YesY
Properties
C10H20O
Molar mass 156.27 g·mol−1
Density 0.855 g/cm3
Boiling point 225 °C (437 °F; 498 K)
Hazards
NFPA 704
Flammability code 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g., diesel fuel Health code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentine Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
2
1
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY verify (what is YesYN ?)
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

  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. 1 2 "Redirect". epa.gov. Retrieved 29 July 2015.
  6. ↑ 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.
  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. ↑ ""Dark" Singlet Oxygenation of β-Citronellol: A Key Step in the Manufacture of Rose Oxide". Organic Process Research & Development.
  9. ↑ http://www.ifraorg.org/en-us/standards_restricted/s3/p3
  10. ↑ Cropwatch Report April 2008
  11. ↑ Survey and health assessment of chemical substances in massage oils
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