Citronellal

Not to be confused with Citronellol or Citronella.

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
CAS Number
3D model (JSmol)
Beilstein Reference
 1209447 1720789
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.070
EC Number
  • 203-376-6
Gmelin Reference
 1521962
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C10H18O/c1-9(2)5-4-6-10(3)7-8-11/h5,8,10H,4,6-7H2,1-3H3 checkY
    Key: NEHNMFOYXAPHSD-UHFFFAOYSA-N checkY
  • InChI=1/C10H18O/c1-9(2)5-4-6-10(3)7-8-11/h5,8,10H,4,6-7H2,1-3H3
    Key: NEHNMFOYXAPHSD-UHFFFAOYAH
SMILES
  • C/C(C)=C/CCC(C)CC=O
  • O=CCC(CC/C=C(/C)C)C
Properties
Chemical formula
 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 labelling:
Pictograms
 GHS07: Exclamation mark GHS09: Environmental hazard[2]
Signal word
 Warning
Hazard statements
 H315, H317, H411[2]
Precautionary statements
 P262, P273, P280, P302+P352[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).
checkY verify (what is checkY☒N ?)
Infobox references

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. ^ a b c 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. S2CID 85112045.
  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).{{cite journal}}: CS1 maint: multiple names: authors list (link) CS1 maint: numeric names: authors list (link)
  6. ^ The British Pharmacopoeia Secretariat (2009). "Index, BP 2009" (PDF). Archived from the original (PDF) on 11 April 2009. Retrieved 31 March 2010.
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