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Citronellal





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Not to be confused with CitronellolorCitronella.

Citronellalorrhodinal (C10H18O) is a monoterpenoid aldehyde, the main component in the mixture of terpenoid chemical compounds that give citronella oil its distinctive lemon scent.

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)
  • Interactive image

    • Beilstein Reference

    		 1209447 1720789
    ChEBI
    ChEMBL
    ChemSpider
    ECHA InfoCard 100.003.070 Edit this at Wikidata
    EC Number
    • 203-376-6

    Gmelin Reference

    		 1521962
    KEGG

    PubChem CID
    UNII

    CompTox Dashboard (EPA)

    • 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

    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 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

    edit

    See also

    edit

    References

    edit
    1. ^ Citronellal, The Merck Index, 12th Edition
  • ^ a b c Record of Citronellal in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 13 March 2020.
  • ^ 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.
  • ^ 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.
  • ^ 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)
  • ^ The British Pharmacopoeia Secretariat (2009). "Index, BP 2009" (PDF). Archived from the original (PDF) on 11 April 2009. Retrieved 31 March 2010.

    • Retrieved from "https://en.wikipedia.org/w/index.php?title=Citronellal&oldid=1183995646"
      



    Last edited on 7 November 2023, at 18:47  





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    ●This page was last edited on 7 November 2023, at 18:47 (UTC).
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