Citronellal

Citronellal[1]
	; (+)-Citronellal
	; (-)-Citronellal
Names
	IUPAC name 3,7-dimethyloct-6-enal
Identifiers
CAS Number	106-23-0 ;
3D model (JSmol)	Interactive image; Interactive image;
ChEBI	CHEBI:47856 ;
ChEMBL	ChEMBL447944 ;
ChemSpider	7506 ;
ECHA InfoCard	100.003.070
EC Number	203-376-6;
KEGG	C17384 ;
PubChem CID	7794;
UNII	QB99VZZ7GZ ;
CompTox Dashboard (EPA)	DTXSID3041790 ;
	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/cm3
Boiling point	201 to 207 °C (394 to 405 °F; 474 to 480 K)
Hazards
GHS pictograms	[2]
GHS Signal word	Warning
GHS hazard statements	H315, H317, H411[2]
GHS precautionary statements	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

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 major isolate in distilled oils from the plants Cymbopogon,[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]

References

Citronellal, The Merck Index, 12th Edition
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. 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.
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).CS1 maint: multiple 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.

[1] Citronellal, The Merck Index, 12th Edition

[GESTIS-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. 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).CS1 maint: multiple names: authors list (link)

[ib29-6] The British Pharmacopoeia Secretariat (2009). "Index, BP 2009" (PDF). Archived from the original (PDF) on 11 April 2009. Retrieved 31 March 2010.

Citronellal

Compendial status

See also

References