Chemistry:Citronellal

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Citronellal[1]
Skeletal formula of (+)-citronellal
Ball-and-stick model of the (+)-citronellal molecule
(+)-Citronellal
Ball-and-stick model of the (-)-citronellal molecule
(-)-Citronellal
Names
IUPAC name
3,7-dimethyloct-6-enal
Identifiers
3D model (JSmol)
1209447 1720789
ChEBI
ChEMBL
ChemSpider
EC Number
  • 203-376-6
1521962
KEGG
UNII
Properties
C10H18O
Molar mass 154.25 g/mol
Density 0.855 g/cm3
Boiling point 201 to 207 °C (394 to 405 °F; 474 to 480 K)
Hazards
GHS pictograms GHS07: Harmful GHS09: Environmental hazard[2]
GHS Signal word Warning
H315, H317, H411[2]
P262, P273, P280, P302+352[2]
Related compounds
Related alkenals
Citral

Methacrolein
trans-2-Methyl-2-butenal

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
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Citronellal or rhodinal (C10H18O) is a monoterpenoid aldehyde, the main component in the mixture of terpenoid chemical compounds that give citronella oil its distinctive lemon scent.

Citronellal is a main isolate in distilled oils from the plants Cymbopogon (excepting C. citratus, culinary lemongrass),[3] lemon-scented gum, and lemon-scented teatree. The (S)-(−)-enantiomer of citronellal makes up to 80% of the oil from kaffir lime leaves and is the compound responsible for its characteristic aroma.

Citronellal has insect repellent properties, and research shows high repellent effectiveness against mosquitoes.[4] Another research shows that citronellal has strong antifungal qualities.[5]

Compendial status

  • British Pharmacopoeia[6]

See also

References

  1. Citronellal, The Merck Index, 12th Edition
  2. 2.0 2.1 2.2 Record of Citronellal in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 13 March 2020.
  3. Mahalwal, Vijender S.; Ali, Mohd. (2003). "Volatile constituents of Cymbopogon nardus (Linn.) Rendle". Flavour and Fragrance Journal 18: 73–76. doi:10.1002/ffj.1144. 
  4. Jeong-Kyu KIM; Chang-Soo KANG; Jong-Kwon LEE; Young-Ran KIM; Hye-Yun HAN; Hwa Kyung YUN (2005). "Evaluation of Repellency Effect of Two Natural Aroma Mosquito Repellent Compounds, Citronella and Citronellal". Entomological Research 35 (2): 117–120. doi:10.1111/j.1748-5967.2005.tb00146.x. 
  5. Kazuhiko NAKAHARA, Najeeb S. ALZOREKY1, Tadashi YOSHIHASHI, Huong T. T. NGUYEN and Gassinee TRAKOONTIVAKORN (2003). "Chemical Composition and Antifungal Activity of Essential Oil from Cymbopogon nardus (Citronella Grass)". JARQ 37 (4). 
  6. The British Pharmacopoeia Secretariat (2009). "Index, BP 2009". Archived from the original on 11 April 2009. https://web.archive.org/web/20090411071437/http://www.pharmacopoeia.co.uk/pdf/2009_index.pdf. Retrieved 31 March 2010.