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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;
3,7-Dimethyl-6-octen-1-ol
Identifiers
3D model (Jmol)
ChEBI
ChemSpider
ECHA InfoCard 100.012.955
KEGG
UNII
Properties
C10H20O
Molar mass 156.27 g·mol−1
Density 0.855 g/cm3
Boiling point 225 °C (437 °F; 498 K)
Hazards
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 fuel Health code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentine Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY  (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.

Citronellol can be prepared by hydrogenation of geraniol or nerol.

Citronellol is used in perfumes and insect repellents, and as a mite attractant. Citronellol is a good mosquito repellent at short distances, but protection greatly lessens when the subject is slightly further from the source. When complexed with β-cyclodextrin, it has on average a 1.5 hour protection duration against mosquitoes.

Citronellol is used as a raw material for the production of rose oxide.

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


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Wikipedia

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