Citronellal

Citronellal^[1]

(+)-Citronellal
(-)-Citronellal
Names
IUPAC name 3,7-dimethyloct-6-en-1-al
Identifiers
CAS Number	106-23-0
ChEBI	CHEBI:47856
ChEMBL	ChEMBL447944
ChemSpider	7506
EC Number	203-376-6
Jmol interactive 3D	Image Image
KEGG	C17384
PubChem	7794
UNII	QB99VZZ7GZ
InChI InChI=1S/C10H18O/c1-9(2)5-4-6-10(3)7-8-11/h5,8,10H,4,6-7H2,1-3H3 Key: NEHNMFOYXAPHSD-UHFFFAOYSA-N 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/cm^3
Boiling point	201 to 207 °C (394 to 405 °F; 474 to 480 K)
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

Citronellal or rhodinal or 3,7-dimethyloct-6-en-1-al (C₁₀H₁₈O) is a monoterpenoid, the main component in the mixture of terpenoid chemical compounds that give citronella oil its distinctive lemon scent.

Citronellal is a major isolate in distilled oils from the plants Cymbopogon,^[2] lemon-scented gum, and lemon-scented teatree. The (–)-(S)-enantiomer of citronellal makes up up to 80% of the leaf 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.^[3] Research shows that citronellal has strong antifungal qualities.^[4]

Compendial status

• British Pharmacopoeia ^[5]

See also

• Citral
• Citronellol
• Geraniol
• Citronella oil
• Hydroxycitronellal
• Perfume allergy

References

1. Citronellal, The Merck Index, 12th Edition
2. Mahalwal, Vijender S.; Ali, Mohd. (2003). "Volatile constituents ofCymbopogon nardus (Linn.) Rendle". Flavour and Fragrance Journal 18: 73. doi:10.1002/ffj.1144.
3. 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.
4. 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).
5. The British Pharmacopoeia Secretariat (2009). "Index, BP 2009" (PDF). Retrieved 31 March 2010.