Citronellal: Difference between revisions
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{{distinguish|Citronellol|Citronella (disambiguation){{!}}Citronella}} |
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{{chembox |
{{chembox |
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| verifiedrevid = |
| verifiedrevid = 443528634 |
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| Reference =<ref>'''Citronellal''', ''[[The Merck Index]], 12th Edition</ref> |
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| Name = Citronellal |
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| ImageFile_Ref = {{chemboximage|correct|??}} |
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| ImageFile = Citronellal |
| ImageFile = Structural formula of (RS)-Citronellal.svg |
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| ImageSize = 150 |
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| ImageAlt = Skeletal formula of (+)-citronellal |
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| ImageFile1 = (+)-Citronellal 3D ball.png |
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| ImageAlt1 = Ball-and-stick model of the (+)-citronellal molecule |
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| ImageFile2 = (-)-Citronellal 3D ball.png |
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| ImageAlt2 = Ball-and-stick model of the (-)-citronellal molecule |
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| ImageCaption2 = (-)-Citronellal |
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| ChemSpiderID = 7506 |
| ChemSpiderID = 7506 |
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| PubChem = 7794 |
| PubChem = 7794 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = QB99VZZ7GZ |
| UNII = QB99VZZ7GZ |
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| KEGG_Ref = {{keggcite| |
| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = C17384 |
| KEGG = C17384 |
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| Beilstein = 1209447 1720789 |
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| Gmelin = 1521962 |
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| 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 |
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| InChIKey = NEHNMFOYXAPHSD-UHFFFAOYAH |
| InChIKey = NEHNMFOYXAPHSD-UHFFFAOYAH |
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| CASNo_Ref = {{cascite|correct|CAS}} |
| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 106-23-0 |
| CASNo = 106-23-0 |
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| EINECS = 203-376-6 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 47856 |
| ChEBI = 47856 |
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| SMILES = C/C(C)=C/CCC(C)CC=O |
| SMILES = C/C(C)=C/CCC(C)CC=O |
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|Section2={{Chembox Properties |
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| Formula = C<sub>10</sub>H<sub>18</sub>O |
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| MolarMass = 154.25 g/mol |
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| Density = 0.855 g/cm<sup>3</sup> |
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| BoilingPtC = 201 to 207 |
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| MeltingPt = |
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| BoilingPt = 201-207 °C |
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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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| GHSSignalWord = Warning |
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| HPhrases = {{H-phrases|315|317|411}}<ref name=GESTIS/> |
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| PPhrases = {{P-phrases|262|273|280|302+352}}<ref name=GESTIS/> |
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}} |
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|Section4={{Chembox Related |
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[[Methacrolein]]<br /> |
[[Methacrolein]]<br /> |
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[[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 |
'''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. |
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Citronellal is a |
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. |
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Citronellal has insect repellent properties, and research shows high repellent effectiveness against mosquitoes.<ref>{{cite journal | |
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> |
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== Compendial status == |
== Compendial status == |
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* [[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> |
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* [[British Pharmacopoeia]] <ref name=ib29>{{cite web |
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| last = The British Pharmacopoeia Secretariat |
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| first = |
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| authorlink = |
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| coauthors = |
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| title = Index, BP 2009 |
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| work = |
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| publisher = |
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| year = 2009 |
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| url = http://www.pharmacopoeia.co.uk/pdf/2009_index.pdf |
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| doi = |
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| accessdate = 31 March 2010}}</ref> |
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{{Expand section|date=March 2010}} |
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==See also== |
==See also== |
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* [[Citral]] |
* [[Citral]] |
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* [[Citronellol]] |
* [[Citronellol]] |
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* [[Geraniol]] |
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* [[Citronella oil]] |
* [[Citronella oil]] |
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* [[Hydroxycitronellal]] |
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* [[Perfume allergy]] |
* [[Perfume allergy]] |
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==References== |
==References== |
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{{reflist}} |
{{reflist}} |
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[[Category:Flavors]] |
[[Category:Flavors]] |
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[[Category: |
[[Category:Alkenals]] |
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[[Category:Monoterpenes]] |
[[Category:Monoterpenes]] |
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[[de:Citronellal]] |
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[[eo:Citronelalo]] |
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[[hu:Citronellál]] |
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[[nl:Citronellal]] |
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[[ja:シトロネラール]] |
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[[pl:Cytronelal]] |
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[[pt:Citronelal]] |
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[[ru:Цитронеллаль]] |
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[[fi:Sitronellaali]] |
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[[zh:香茅醛]] |