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;
3,7-Dimethyl-6-octen-1-ol
Identifiers
106-22-9 YesY
ChEBI CHEBI:50462 YesY
ChEMBL ChEMBL395827 YesY
ChemSpider 13850135 YesY
Jmol 3D model Interactive image
Interactive image
KEGG C09849 YesY
UNII P01OUT964K YesY
  • InChI=1S/C10H20O/c1-9(2)5-4-6-10(3)7-8-11/h5,10-11H,4,6-8H2,1-3H3 YesY
    Key: QMVPMAAFGQKVCJ-UHFFFAOYSA-N YesY
  • 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 156.27 g·mol−1
Density 0.855 g/cm3
Boiling point 225 °C (437 °F; 498 K)
Vapor pressure {{{value}}}
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

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  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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