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Revision as of 16:30, 7 August 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'DrugBank_Ref', 'ChEBI_Ref') per Chem/Drugbox validation (report errors or [[user← Previous edit		Latest revision as of 13:17, 15 November 2024 edit undoSylveon soulmate (talk | contribs)10 editsm →Uses: fix broken link to vitamin K
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			{{Use dmy dates|date=March 2021}}
			{{dist|Geraniol}}
	{{chembox		{{chembox
			| Watchedfields = changed
	| verifiedrevid = 443526975
			| verifiedrevid = 443528330
	| Reference = <ref>'''Citral''', '']'', 12th Edition.</ref>
			| Reference = <ref>'''Citral''', '']'', 12th Edition.</ref>
	| Name = Citral
			| Name = Citral
	| ImageFile = Geranial1.png
			| ImageFile = Geranial 2.svg
	| ImageSize = 200px
			| ImageAlt = Skeletal formula of geranial
	| ImageName = Geranial
			| ImageCaption = Geranial
	| ImageFile1 = Neral1.png
			| ImageFile1 = Geranial 3D ball.png
	| ImageSize1 = 200px
			| ImageAlt1 = Ball-and-stick model of the geranial molecule
	| ImageName1 = Neral
			| ImageFile2 = Neral_svg.svg
	| IUPACName = 3,7-dimethylocta-2,6-dienal
			| ImageAlt2 = Skeletal formula of neral
	| OtherNames = citral<br />geranial<br />neral<br />geranialdehyde
			| ImageCaption2 = Neral
	| Section1 = {{Chembox Identifiers
			| ImageFile3 = Neral-3D-balls.png
	| ChEBI_Ref = {{ebicite|correct|EBI}}
			| ImageAlt3 = Ball-and-stick model of the neral molecule
			| IUPACName = 3,7-dimethylocta-2,6-dienal
			| OtherNames = citral<br />geranialdehyde
			|Section1={{Chembox Identifiers
			| IUPHAR_ligand = 6327
			| ChEBI_Ref = {{ebicite|correct|EBI}}
	| ChEBI = 16980		| ChEBI = 16980
	| SMILES = O=CC=C(C)CCC=C(C)C		| SMILES = O=CC=C(C)CCC=C(C)C
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 553578		| ChemSpiderID = 553578
	| PubChem = 638011		| PubChem = 638011
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	| ChEMBL_Ref = {{ebicite|correct|EBI}}		| ChEMBL_Ref = {{ebicite|correct|EBI}}
	| ChEMBL = 1080997		| ChEMBL = 1080997
			| 3DMet = B00306
			| EC_number = 226-394-6
			| UNNumber = 2810
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}		| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChI = 1S/C10H16O/c1-9(2)5-4-6-10(3)7-8-11/h5,7-8H,4,6H2,1-3H3/b10-7+		| StdInChI = 1S/C10H16O/c1-9(2)5-4-6-10(3)7-8-11/h5,7-8H,4,6H2,1-3H3/b10-7+
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	| CASNo_Ref = {{cascite|correct|CAS}}		| CASNo_Ref = {{cascite|correct|CAS}}
	| CASNo = 5392-40-5		| CASNo = 5392-40-5
	| RTECS = RG5075000		| RTECS = RG5075000
	| KEGG_Ref = {{keggcite|correct|kegg}}		| KEGG_Ref = {{keggcite|correct|kegg}}
	| KEGG = C01499		| KEGG = C01499
	}}		}}
	| Section2 = {{Chembox Properties		|Section2={{Chembox Properties
	| Formula = C<sub>10</sub>H<sub>16</sub>O		| Formula = C<sub>10</sub>H<sub>16</sub>O
	| MolarMass = 152.24 g/mol		| MolarMass = 152.24 g/mol
	| Appearance = Pale yellow liquid		| Appearance = Pale yellow liquid
	| Odor = Lemon like		| Odor = Lemon like
	| Density = 0.893 g/cm³		| Density = 0.893 g/cm<sup>3</sup>
	| Vapor Pressure = 0.22 mmHg (20 °C)		| VaporPressure = 0.22{{nbsp}}mmHg (20{{nbsp}}°C)
			| Solubility =
	| Vapor Density = 5.2 (Air=1)
	| Solubility =		| MeltingPt =
			| BoilingPtC = 229
	| MeltingPt =
			| pKa =
	| BoilingPtC = 229
			| MagSus = {{val|−98.9e−6|u=cm<sup>3</sup>/mol}}
	| pKa =
	}}		}}
	| Section3 = {{Chembox Structure		|Section3={{Chembox Structure
	| Dipole =		| Dipole =
	}}		}}
	| Section7 = {{Chembox Hazards		|Section7={{Chembox Hazards
	| NFPA-H = 0 | NFPA-F = 1 | NFPA-R = 0 | NFPA-O =		| NFPA-H = 0 | NFPA-F = 1 | NFPA-R = 0 | NFPA-S =
	| RPhrases = {{R36}}, {{R37}}, {{R38}}		| GHSPictograms = {{GHS07}}
			| GHSSignalWord = Warning
	| SPhrases =
			| HPhrases = {{H-phrases|315|317}}
	| FlashPt = 91 °C
			| PPhrases = {{P-phrases|261|264|272|280|302+352|321|332+313|333+313|362|363|501}}
			| FlashPtC = 91
	}}		}}
	| Section8 = {{Chembox Related		|Section8={{Chembox Related
	| Function = alkenals		| OtherFunction_label = alkenals
			| OtherFunction = {{ubl
	| OtherFunctn = ]<br />
			| ]
	]<br />
			| ]
	]
			| ]
	| OtherCpds =
			}}
			| OtherCompounds =
	}}		}}
	}}		}}
			'''Citral''' is an acyclic monoterpene aldehyde. Being a ], it is made of two ]s. Citral is a collective term which covers two geometric isomers that have their own separate names; the ] is named '''geranial''' (''trans''-citral; α-citral<ref name="Waghulde2020">{{cite journal |last1=Waghulde |first1=S. |last2=Parmar |first2=P. |last3=Mule |first3=J. |last4=Pashte |first4=D. |last5=Patil |first5=B. |last6=Modhale |first6=N. |last7=Gorde |first7=N. |last8=Kharche |first8=A. |last9=Kale |first9=M. |date=2020 |title=Lead Finding from Plant Cymbopogon Citratus with Immunomodulator Potentials through in Silico Methods |journal=Chemistry Proceedings |language=en |volume=3 |issue=1 |pages=77 |doi=10.3390/ecsoc-24-08302 |issn=2673-4583 |doi-access=free }}</ref>) or citral A. The ''Z''-isomer is named '''neral''' (''cis''-citral; β-citral<ref name="Waghulde2020" />) or citral B. These ]s occur as a mixture, often not in equal proportions; e.g. in essential oil of ], the neral to geranial ratio is 0.61.<ref name=Zachariah>{{cite book |last1=Zachariah |first1=T. J. |last2=Parthasarathy |first2=V. A. |last3=Chempakam |first3=B. |title=Chemistry of spices |page=76 |date=2008 |publisher=CABI |oclc=1120264204 |isbn=9781845934057 |location=Wallingford}}</ref>
	'''Citral''', or '''3,7-dimethyl-2,6-octadienal''' or '''lemonal''', is either of, or a mixture of, a pair of ]s with the molecular formula ]<sub>10</sub>]<sub>16</sub>]. The two compounds are double bond ]s. The ] is known as '''geranial''' or citral A. The ] is known as '''neral''' or citral B.
	== Occurrence ==		== Occurrence ==
			Citral is present in the ]s of several plants, including ] (90–98%), '']'' (90%), '']'' (70–85%), ] (65–85%), ] (70–80%), '']'' (66.5%), '']'' (about 65%), '']'' (about 62%), ] (36%), ] (30–35%), ] (26%), ] (11%), ] (6–9%), ] (2–5%), and ].<ref>{{cite book|last1=Fenaroli |first1=G. |last2=Furia |first2=T.E. |last3=Bellanca |first3=N. |title=Handbook of Flavor Ingredients |isbn=0-87819-532-7}}</ref><ref>{{cite book|last1=Lawless |first1=J. |title=The Illustrated Encyclopedia of Essential Oils |date=2 November 1995 |publisher=Element |isbn=1-85230-661-0}}</ref><ref>{{Cite web |url=http://www.aromaticplantproject.com/articles_archive/lemon_citrus_scented_oils.html |title=The Aromatic Plant Project |access-date=1 June 2008 |archive-date=24 November 2019 |archive-url=https://web.archive.org/web/20191124031814/http://www.aromaticplantproject.com/articles_archive/lemon_citrus_scented_oils.html |url-status=dead }}</ref> Further, in the lipid fraction (essential oil) of Australian ginger (51–71%)<ref name=Zachariah /> Of the many sources of citral, the Australian myrtaceous tree, lemon myrtle, '']'' F. Muell. (of the family ]), is considered superior.<ref name=Southwell2021>{{cite journal |last1=Southwell |first1=Ian |title=''Backhousia citriodora'' F. Muell. (Lemon Myrtle), an Unrivalled Source of Citral |journal=Foods |date=9 July 2021 |volume=10 |issue=7 |pages=1596 |doi=10.3390/foods10071596 |pmid=34359465 |pmc=8305781 |doi-access=free }}</ref>
	Citral is present in the oils of several plants, including ] (90-98%), '']'' (90%), '']'' (70-85%), ] (65-85%), ] (70-80%), '']'' (66.5%), '']'' (about 65%), '']'' (about 62%), ] (36%), ] (30-35%), ] (26%), ] (11%), ] (6-9%), ] (2-5%), and ].<ref>Fenaroli, G., Furia, T.E., Bellanca, N., ''Handbook of Flavor Ingredients'', ISBN 0878195327</ref><ref>Lawless, J., ''The Illustrated Encyclopedia of Essential Oils'', ISBN 1-85230-661-0</ref><ref></ref>
	== Uses ==		== Uses ==
			Citral is a precursor in the industrial production of ], ], ].
			Citral is also precursor to ], ] and ].
	Geranial has a strong lemon odor. Neral's lemon odor is less intense, but sweeter. Citral is therefore an ] used in perfumery for its citrus effect. Citral is also used as a flavor and for fortifying lemon oil. It also has strong ] qualities,<ref>{{cite journal | author = Onawunmi, G.O. |year=1989 | title=Evaluation of the antimicrobial activity of citral |journal=Lett. Appl. Microbial. | volume=9 |pages=105–108 | doi = 10.1111/j.1472-765X.1989.tb00301.x}}</ref> and pheromonal effects in insects.<ref>{{cite journal | author = Kuwahara, Y., Suzuki, H., Matsumoto, K. & Wada, Y. |year=1983 |title=Pheromone study on acarid mites. XI. Function of mite body as geometrical isomerization and reduction of citral (the alarm pheromone) Carpoglyphus lactis |journal=Appl. Entomol. Zool. |volume=18 |pages=30–39}}</ref><ref>{{cite journal | author = Robacker, D.C. & Hendry, L.B. |year=1977 |title=Neral and geranial: components of the sex pheromone of the parasitic wasp, Itoplectis conquisitor | journal=J. Chem. Ecol. |volume=3 |pages=563–577 | doi = 10.1007/BF00989077}}</ref>
			===Fragrances===
	Citral is used in the synthesis of ], ], and methylionone, and to mask the smell of smoke.
			Citral has a strong lemon (citrus) scent and is used as an ] in perfumery. It is used to fortify lemon oil. (Nerol, another perfumery compound, has a less intense but sweeter lemon note.) The aldehydes citronellal and citral are considered key components responsible for the lemon note with citral preferred.<ref name=Southwell2021/>
			It also has pheromonal effects in ] and ].<ref>{{cite journal |last1=Kuwahara |first1=Yasumasa |last2=Suzuki |first2=Hiroshi |last3=Matsumoto |first3=Katsuhiko |last4=Wada |first4=Yoshitake |title=Pheromone Study on Acarid Mites. XI. Function of Mite Body as Geometrical Isomerization and Reduction of Citral (the Alarm Pheromone) |journal=Applied Entomology and Zoology |date=1983 |volume=18 |issue=1 |pages=30–39 |doi=10.1303/aez.18.30 |doi-access=free }}</ref><ref>{{cite journal |author1=Robacker, D.C. |author2=Hendry, L.B. |year=1977 |title=Neral and geranial: components of the sex pheromone of the parasitic wasp, Itoplectis conquisitor | journal=Journal of Chemical Ecology |volume=3 |pages=563–577 | doi = 10.1007/BF00989077 | issue = 5|s2cid=11568355 }}</ref>
	==Health and safety information==
	Citral should be avoided by people with ].<ref></ref>
			The herb '']'' has shown promising insecticidal and antifungal activity against storage pests.<ref name="Dubey et al 1997">{{cite journal |last1=Dubey |first1=N. K. |last2=Takeya |first2=Koichi |last3=Itokawa |first3=Hideji |title=Citral: A cytotoxic principle isolated from the essential oil of Cymbopogon citratus against P388 leukaemia cells |journal=Current Science |date=1997 |volume=73 |issue=1 |pages=22–24 |jstor=24098141 }}</ref>
	== Compendial status ==
	* ] <ref name=ib29>{{cite web
			=== Food additive ===
	| last = The British Pharmacopoeia Secretariat
			Citral is commonly used as a food additive ingredient.<ref>{{cite journal |last1=Liao |first1=Pei-Chun |last2=Yang |first2=Tsung-Shi |last3=Chou |first3=Ju-Ching |last4=Chen |first4=Jie |last5=Lee |first5=Shu-Ching |last6=Kuo |first6=Yueh-Hsiung |last7=Ho |first7=Chen-Lung |last8=Chao |first8=Louis Kuo-Ping |title=Anti-inflammatory activity of neral and geranial isolated from fruits of ''Litsea cubeba'' Lour |journal=Journal of Functional Foods |date=1 December 2015 |volume=19 |pages=248–258 |doi=10.1016/j.jff.2015.09.034 |doi-access=free }}</ref>
	| first =
	| authorlink =
			It has been tested (2016) in vitro against the food-borne pathogen '']''.<ref>{{cite journal |last1=Shi |first1=Chao |last2=Song |first2=Kaikuo |last3=Zhang |first3=Xiaorong |last4=Sun |first4=Yi |last5=Sui |first5=Yue |last6=Chen |first6=Yifei |last7=Jia |first7=Zhenyu |last8=Sun |first8=Huihui |last9=Sun |first9=Zheng |last10=Xia |first10=Xiaodong |title=Antimicrobial Activity and Possible Mechanism of Action of Citral against ''Cronobacter sakazakii'' |journal=PLOS ONE |date=14 July 2016 |volume=11 |issue=7 |pages=e0159006 |doi=10.1371/journal.pone.0159006 |pmid=27415761 |pmc=4945043 |bibcode=2016PLoSO..1159006S |doi-access=free }}</ref>
	| 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 ==
	* ]
	* ]
	* ]		* ]
	* ]		* ]
			* ]
	* ]		* ]
	* ]		* ]
	== References ==		== References ==
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	== External links ==		== External links ==
	*		* {{Webarchive|url=https://web.archive.org/web/20070818041949/http://physchem.ox.ac.uk/MSDS/CI/citral.html |date=18 August 2007 }}
	{{Use dmy dates|date=January 2011}}
	]
	]		]
	]		]
	]		]
			]
	]
	]
	]
	]
	]
	]
	]
	]
	]
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	]