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]

Not to be confused with Citronellal.
Citronellol

(+)-Citronellol (left) and (−)-citronellol (right)

(+)-Citronellol

(−)-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
  • InChI=1S/C10H20O/c1-9(2)5-4-6-10(3)7-8-11/h5,10-11H,4,6-8H2,1-3H3 Y
    Key: QMVPMAAFGQKVCJ-UHFFFAOYSA-N Y
  • InChI=1/C10H20O/c1-9(2)5-4-6-10(3)7-8-11/h5,10-11H,4,6-8H2,1-3H3/t10-/m1/s1
    Key: QMVPMAAFGQKVCJ-SNVBAGLBBU
  • InChI=1/C10H20O/c1-9(2)5-4-6-10(3)7-8-11/h5,10-11H,4,6-8H2,1-3H3
    Key: QMVPMAAFGQKVCJ-UHFFFAOYAO
  • OCC[C@@H](CC/C=C(/C)C)C
  • C\C(C)=C\CCC(C)CCO
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 labelling:
Warning
H315, H317, H319
P261, P264, P272, P273, P280, P302+P352, P305+P351+P338, P321, P332+P313, P333+P313, P337+P313, P362, P363, P391, P501
NFPA 704 (fire diamond)
1
2
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references

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 90-minute 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. (1995). The Illustrated Encyclopedia of Essential Oils. ISBN 978-1-85230-661-8.
  2. Morris, Robert H. (2007). "Ruthenium and Osmium". In De Vries, J. G.; Elsevier, C. J. (eds.). 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, W. G.; Schreck, C. E. (1985). "Chiral-phase capillary gas chromatography and mosquito repellent activity of some oxazolidine derivatives of (+)- and (−)-citronellol". Journal of Pharmaceutical Sciences. 74 (5): 534–539. doi:10.1002/jps.2600740508. PMID 2862274.
  5. "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): 63–68. 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. S2CID 93566912.
  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.{{cite web}}: CS1 maint: archived copy as title (link)
  10. "Cropwatch Report April 2008" (PDF). Archived from the original (PDF) on 10 February 2014. Retrieved 19 July 2012.
  11. Survey and health assessment of chemical substances in massage oils Archived 27 September 2007 at the Wayback Machine
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