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Citronellal

From Wikipedia, the free encyclopedia
Not to be confused withCitronellol orCitronella.

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
ECHA InfoCard100.003.070Edit this at Wikidata
EC Number
  • 203-376-6
1521962
KEGG
UNII
  • 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
  • C/C(C)=C/CCC(C)CC=O
  • O=CCC(CC/C=C(/C)C)C
Properties
C10H18O
Molar mass154.25 g/mol
Density0.855 g/cm3
Boiling point201 to 207 °C (394 to 405 °F; 474 to 480 K)
Hazards
GHS labelling:
GHS07: Exclamation markGHS09: Environmental hazard[2]
Warning
H315,H317,H411[2]
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 theirstandard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Chemical compound

Citronellal orrhodinal (C10H18O) is a monoterpenoidaldehyde, the main component in the mixture of terpenoidchemical compounds that givecitronella oil its distinctive lemon scent.

Citronellal is a mainisolate in distilled oils from the plantsCymbopogon (excepting C. citratus, culinary lemongrass),[3]lemon-scented gum, andlemon-scented teatree. The (S)-(−)-enantiomer of citronellal makes up to 80% of the oil fromkaffir 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

[edit]

See also

[edit]

References

[edit]
  1. ^Citronellal,The Merck Index, 12th Edition
  2. ^abcRecord ofCitronellal in theGESTIS Substance Database of theInstitute 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 fromthe original(PDF) on 11 April 2009. Retrieved31 March 2010.
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