Citronellol

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;
Identifiers
3D model (JSmol)
1362474
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.069
EC Number
  • 247-737-6
KEGG
UNII
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 pictograms GHS07: HarmfulGHS09: Environmental hazard
GHS Signal word Warning
H315, H317, H319
P261, P264, P272, P273, P280, P302+352, P305+351+338, P321, P332+313, P333+313, P337+313, P362, P363, P391, P501
NFPA 704 (fire diamond)
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 fuelHealth code 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial 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).
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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[edit]

Citronellol can be prepared by hydrogenation of geraniol or nerol.[2][3]

Uses[edit]

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[edit]

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[edit]

References[edit]

  1. ^ Lawless, J. (1995). The Illustrated Encyclopedia of Essential Oils. ISBN 978-1-85230-661-8.
  2. ^ 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.
  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. ^ a b "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. ^ Alsters, Paul L.; Jary, Walther; Aubry, Jean-Marie (2010). ""Dark" Singlet Oxygenation of β-Citronellol: A Key Step in the Manufacture of Rose Oxide". Organic Process Research & Development. 14: 259–262. doi:10.1021/op900076g.
  9. ^ "Archived copy". Archived from the original on 6 January 2012. Retrieved 19 July 2012.CS1 maint: archived copy as title (link)
  10. ^ Cropwatch Report April 2008
  11. ^ Survey and health assessment of chemical substances in massage oils Archived 27 September 2007 at the Wayback Machine