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Citronellol

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Title: Citronellol  
Author: World Heritage Encyclopedia
Language: English
Subject: Citronella oil, Rose oil, Nerol, Monarda citriodora, Myrcene
Collection: Alcohols, Alkenes, Flavors, Monoterpenes, Perfume Ingredients
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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
 Y
ChEBI  Y
ChEMBL  Y
ChemSpider  Y
Jmol-3D images Image
Image
KEGG  Y
UNII  Y
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
2
1
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 Y  (: Y/N?)

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]

Contents

  • Preparation 1
  • Uses 2
  • Health and safety 3
  • See also 4
  • References 5

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.

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,[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]

See also

References

  1. ^ Lawless, J. The Illustrated Encyclopedia of Essential Oils.  
  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.  
  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.  
  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.  
  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.  
  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.  
  8. ^ http://www.ifraorg.org/en-us/standards_restricted/s3/p3
  9. ^ Cropwatch Report April 2008
  10. ^ Survey and health assessment of chemical substances in massage oils
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