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;
Beilstein Reference	1209447 1720789
ChEBI	CHEBI:47856 ;
ChEMBL	ChEMBL447944 ;
ChemSpider	7506 ;
ECHA InfoCard	100.003.070
EC Number	203-376-6;
Gmelin Reference	1521962
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 labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H317, H411
Precautionary statements	P262, P273, P280, P302+P352
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 (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 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

British Pharmacopoeia^[6]

References

^ 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.

[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: 73–76. 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)

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

[1]

[2]

[3]

[4]

[5]

[6]

Names

(+)-Citronellal
(-)-Citronellal
IUPAC name 3,7-dimethyloct-6-enal
Identifiers
CAS Number	106-23-0^Y
3D model (JSmol)	Interactive image Interactive image
Beilstein Reference	1209447 1720789
ChEBI	CHEBI:47856^Y
ChEMBL	ChEMBL447944^Y
ChemSpider	7506^Y
ECHA InfoCard	100.003.070
EC Number	203-376-6
Gmelin Reference	1521962
KEGG	C17384^Y
PubChem CID	7794
UNII	QB99VZZ7GZ^Y
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^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)
Hazards
GHS labelling:
Pictograms	^[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). Y verify (what is ^YN ?) Infobox references

Citronellal

Compendial status

See also

References