Citronellol

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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 100.012.955
EC Number 247-737-6
KEGG
UNII
Properties
C10H20O
Molar mass 156.27 g·mol−1
Density 0.855 g/cm3
Boiling point 225 °C (437 °F; 498 K)
Viscosity 11.1 mPa s
Hazards
GHS pictograms The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)The environment pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
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
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. 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. ^ 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. 
  10. ^ Cropwatch Report April 2008
  11. ^ Survey and health assessment of chemical substances in massage oils Archived 27 September 2007 at the Wayback Machine.