Citronellal

Citronellal^[1]
	; (+)-Citronellal
	; (-)-Citronellal
Names
	IUPAC name 3,7-dimethyloct-6-en-1-al
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 ;
	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)
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).
	verify (what is ?)
	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 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]

References

↑ Citronellal, The Merck Index, 12th Edition
↑ Mahalwal, Vijender S.; Ali, Mohd. (2003). "Volatile constituents ofCymbopogon 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).
↑ 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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[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).

[ib29-5] The British Pharmacopoeia Secretariat (2009). "Index, BP 2009" (PDF). Archived from the original (PDF) on 11 April 2009. Retrieved 31 March 2010.

Names

(+)-Citronellal
(-)-Citronellal
IUPAC name 3,7-dimethyloct-6-en-1-al
Identifiers
CAS Number	106-23-0^Y
3D model (JSmol)	Interactive image Interactive image
ChEBI	CHEBI:47856^Y
ChEMBL	ChEMBL447944^Y
ChemSpider	7506^Y
ECHA InfoCard	100.003.070
EC Number	203-376-6
KEGG	C17384^Y
PubChem CID	7794
UNII	QB99VZZ7GZ^Y
InChI InChI=1S/C10H18O/c1-9(2)5-4-6-10(3)7-8-11/h5,8,10H,4,6-7H2,1-3H3^Y Key: NEHNMFOYXAPHSD-UHFFFAOYSA-N^Y 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)
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).
Y verify (what is ^YN ?)
Infobox references

Citronellal

Compendial status

See also

References