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{{distinguish|Citronellol|Citronella (disambiguation){{!}}Citronella}}
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{{Use dmy dates|date=March 2021}}
{{chembox
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| Watchedfields = changed
| verifiedrevid = 407462822
| verifiedrevid = 443528634
| Reference=<ref>'''Citronellal''', ''[[The Merck Index]], 12th Edition</ref>
| Reference =<ref>'''Citronellal''', ''[[The Merck Index]], 12th Edition</ref>
| Name = Citronellal
| Name = Citronellal
| ImageFile_Ref = {{chemboximage|correct|??}}
| ImageFile_Ref = {{chemboximage|correct|??}}
| ImageFile = Citronellal-2D-skeletal.png
| ImageFile = Structural formula of (RS)-Citronellal.svg
| ImageSize = 200px
| ImageSize = 150
| ImageAlt = Skeletal formula of (+)-citronellal
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| ImageName = Citronellal
| ImageFile1 = (+)-Citronellal 3D ball.png
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| IUPACName = 3,7-dimethyloct-6-en-1-al
| ImageAlt1 = Ball-and-stick model of the (+)-citronellal molecule
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| Section1 = {{Chembox Identifiers
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| ImageCaption1 = (+)-Citronellal
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ImageFile2 = (-)-Citronellal 3D ball.png
| ImageAlt2 = Ball-and-stick model of the (-)-citronellal molecule
| ImageCaption2 = (-)-Citronellal
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| IUPACName = 3,7-dimethyloct-6-enal
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|Section1={{Chembox Identifiers
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 7506
| ChemSpiderID = 7506
| PubChem = 7794
| PubChem = 7794
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = QB99VZZ7GZ
| UNII = QB99VZZ7GZ
| KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C17384
| KEGG = C17384
| Beilstein = 1209447 1720789
| Gmelin = 1521962
| InChI = 1/C10H18O/c1-9(2)5-4-6-10(3)7-8-11/h5,8,10H,4,6-7H2,1-3H3
| InChI = 1/C10H18O/c1-9(2)5-4-6-10(3)7-8-11/h5,8,10H,4,6-7H2,1-3H3
| InChIKey = NEHNMFOYXAPHSD-UHFFFAOYAH
| InChIKey = NEHNMFOYXAPHSD-UHFFFAOYAH
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| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 106-23-0
| CASNo = 106-23-0
| EINECS = 203-376-6
| EINECS = 203-376-6
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 47856
| ChEBI = 47856
| SMILES = C/C(C)=C/CCC(C)CC=O
| SMILES = C/C(C)=C/CCC(C)CC=O
}}
}}
| Section2 = {{Chembox Properties
|Section2={{Chembox Properties
| Formula = C<sub>10</sub>H<sub>18</sub>O
| Formula = C<sub>10</sub>H<sub>18</sub>O
| MolarMass = 154.25 g/mol
| MolarMass = 154.25 g/mol
| Density = 0.855 g/cm<sup>3</sup>
| Density = 0.855 g/cm<sup>3</sup>
| BoilingPtC = 201 to 207
| MeltingPt =
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}}
| BoilingPt = 201-207 °C
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|Section3={{Chembox Hazards
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}}
| GHSPictograms = {{GHS exclamation mark}} {{GHS environment}}<ref name="GESTIS">{{GESTIS|ZVG=491257 |CAS=123-72-8 |Name=Citronellal |Date=13 March 2020 }}</ref>
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| Section3 = {{Chembox Related
| GHSSignalWord = Warning
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| Function = alkenals
| HPhrases = {{H-phrases|315|317|411}}<ref name=GESTIS/>
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| OtherFunctn = [[Citral]]<br />
| PPhrases = {{P-phrases|262|273|280|302+352}}<ref name=GESTIS/>
}}
|Section4={{Chembox Related
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| OtherFunction_label = alkenals
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| OtherFunction = [[Citral]]<br />
[[Methacrolein]]<br />
[[Methacrolein]]<br />
[[trans-2-Methyl-2-butenal|''trans''-2-Methyl-2-butenal]]
[[trans-2-Methyl-2-butenal|''trans''-2-Methyl-2-butenal]]
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}}
}}


'''Citronellal''' or '''rhodinal''' or '''3,7-dimethyloct-6-en-1-al''' ([[Carbon|C]]<sub>10</sub>[[Hydrogen|H]]<sub>18</sub>[[Oxygen|O]]) is a [[terpenoid|monoterpenoid]], the main component in the mixture of terpenoid [[chemical compound]]s that give [[citronella oil]] its distinctive lemon scent.
'''Citronellal''' or '''rhodinal''' ([[Carbon|C]]<sub>10</sub>[[Hydrogen|H]]<sub>18</sub>[[Oxygen|O]]) is a mono[[terpenoid]] [[aldehyde]], the main component in the mixture of terpenoid [[chemical compound]]s that give [[citronella oil]] its distinctive lemon scent.


Citronellal is a major [[isolate]] in distilled oils from the plants ''[[Cymbopogon]]'',<ref>{{cite journal | doi = 10.1002/ffj.1144 | title = Volatile constituents ofCymbopogon nardus (Linn.) Rendle | year = 2003 | last1 = Mahalwal | first1 = Vijender S. | last2 = Ali | first2 = Mohd. | journal = Flavour and Fragrance Journal | volume = 18 | pages = 73}}</ref> [[Corymbia citriodora|lemon-scented gum]], and [[Leptospermum petersonii|lemon-scented teatree]].
Citronellal is a main [[chemical isolate|isolate]] in distilled oils from the plants ''[[Cymbopogon]]'' (excepting C. citratus, culinary lemongrass),<ref>{{cite journal | doi = 10.1002/ffj.1144 | title = Volatile constituents of Cymbopogon nardus (Linn.) Rendle | year = 2003 | last1 = Mahalwal | first1 = Vijender S. | last2 = Ali | first2 = Mohd. | journal = Flavour and Fragrance Journal | volume = 18 | pages = 73–76| doi-access = free }}</ref> [[Corymbia citriodora|lemon-scented gum]], and [[Leptospermum petersonii|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.<ref>{{cite journal | author = Jeong-Kyu KIM, Chang-Soo KANG, Jong-Kwon LEE, Young-Ran KIM, Hye-Yun HAN, Hwa Kyung YUN | title = Evaluation of Repellency Effect of Two Natural Aroma Mosquito Repellent Compounds, Citronella and Citronellal | journal = Entomological Research | volume = 35 | issue = 2 | pages = 117–120 | year = 2005 | doi = 10.1111/j.1748-5967.2005.tb00146.x}}</ref> Research shows that citronellal has strong antifungal qualities.<ref>{{cite journal | author = Kazuhiko NAKAHARA, Najeeb S. ALZOREKY1 , Tadashi YOSHIHASHI, Huong T. T. NGUYEN and Gassinee TRAKOONTIVAKORN | title = Chemical Composition and Antifungal Activity of Essential Oil from Cymbopogon nardus (Citronella Grass)'' | journal = JARQ | year = 2003 | volume = 37 | issue = 4}}</ref>
Citronellal has insect repellent properties, and research shows high repellent effectiveness against mosquitoes.<ref>{{cite journal |author1=Jeong-Kyu KIM |author2=Chang-Soo KANG |author3=Jong-Kwon LEE |author4=Young-Ran KIM |author5=Hye-Yun HAN |author6=Hwa Kyung YUN | title = Evaluation of Repellency Effect of Two Natural Aroma Mosquito Repellent Compounds, Citronella and Citronellal | journal = Entomological Research | volume = 35 | issue = 2 | pages = 117–120 | year = 2005 | doi = 10.1111/j.1748-5967.2005.tb00146.x|s2cid=85112045 }}</ref> Another research shows that citronellal has strong antifungal qualities.<ref>{{cite journal | author = Kazuhiko NAKAHARA, Najeeb S. ALZOREKY1, Tadashi YOSHIHASHI, Huong T. T. NGUYEN and Gassinee TRAKOONTIVAKORN | title = Chemical Composition and Antifungal Activity of Essential Oil from Cymbopogon nardus (Citronella Grass) | journal = JARQ | year = 2003 | volume = 37 | issue = 4}}</ref>


== Compendial status ==
== Compendial status ==
* [[British Pharmacopoeia]]<ref name=ib29>{{cite web|last=The British Pharmacopoeia Secretariat|title=Index, BP 2009|year=2009|url=http://www.pharmacopoeia.co.uk/pdf/2009_index.pdf|accessdate=31 March 2010|url-status=dead|archiveurl=https://web.archive.org/web/20090411071437/http://www.pharmacopoeia.co.uk/pdf/2009_index.pdf|archivedate=11 April 2009}}</ref>
* [[British Pharmacopoeia]] <ref name=ib29>{{cite web
| last = The British Pharmacopoeia Secretariat
| first =
| authorlink =
| coauthors =
| title = Index, BP 2009
| work =
| publisher =
| year = 2009
| url = http://www.pharmacopoeia.co.uk/pdf/2009_index.pdf
| format =
| doi =
| accessdate = 31 March 2010}}</ref>
{{Expand section|date=March 2010}}


==See also==
==See also==

* [[Citral]]
* [[Citral]]
* [[Citronellol]]
* [[Citronellol]]
* [[Geraniol]]
* [[Citronella oil]]
* [[Citronella oil]]
* [[Hydroxycitronellal]]
* [[Perfume allergy]]
* [[Perfume allergy]]


==References==
==References==
{{reflist}}
{{reflist}}

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{{Use dmy dates|date=January 2011}}


[[Category:Flavors]]
[[Category:Flavors]]
[[Category:Aldehydes]]
[[Category:Alkenals]]
[[Category:Monoterpenes]]
[[Category:Monoterpenes]]

[[de:Citronellal]]
[[eo:Citronelalo]]
[[hu:Citronellál]]
[[nl:Citronellal]]
[[ja:シトロネラール]]
[[pl:Cytronelal]]
[[pt:Citronelal]]
[[ru:Цитронеллаль]]
[[fi:Sitronellaali]]
[[zh:香茅醛]]
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