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Citronellol

Pair of enantiomers From Wikipedia, the free encyclopedia

Citronellol

Not to be confused with Citronellal.

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 widespread, but particularly abundant in the oils of rose (18–55%) and Pelargonium geraniums.[1]

Quick Facts Names, Identifiers ...
Citronellol
Thumb
(+)-Citronellol (left) and (−)-citronellol (right)
Thumb
R-(+)-Citronellol
Thumb
S-(−)-Citronellol
Names
IUPAC name
3,7-Dimethyloct-6-en-1-ol
Other names
(±)-β-Citronellol; Cephrol, Corol
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:
GHS07: Exclamation markGHS09: Environmental hazard
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)
ThumbHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 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 fuelInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
2
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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Preparation

Several million kilograms of citronellol are produced annually. It is mainly obtained by partial hydrogenation of geraniol or nerol over copper chromite catalyst.[2] Hydrogenation of both C=C bonds using a nickel catalyst gives tetrahydrogeraniol, yet another commercial fragrance.[3]

Homogeneous catalysts have been investigated for the production of enantiomers.[4][5]

Uses

Citronellol is used in perfumes and as a fragrance in cleaning products. In many applications, one of the enantiomers is preferred. It is a component of citronella oil, an insect repellant.[2]

Citronellol is used as a raw material for the production of rose oxide.[2][6] It is also a precursor to many commercial and potential fragrances such as citronellol acetate, citronellyl oxyacetaldehyde, citronellyl methyl acetal, and ethyl citronellyl oxalate.[2]

Health and safety

The United States FDA considers citronellol as generally recognized as safe (GRAS) for food use.[7] Citronellol is subject to restrictions on its use in perfumery,[8] as some people may become sensitised to it, but the degree to which citronellol can cause an allergic reaction in humans is disputed.[9][10]

In terms of dermal safety, citronellol has been evaluated as an insect repellent.[11]

See also

References

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