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Revision as of 16:32, 7 August 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (changes to verified and watched fields - updated 'DrugBank_Ref', 'ChEBI_Ref') per Chem/Drugbox validation (report errors or [[user t← Previous edit Latest revision as of 13:18, 26 October 2024 edit undoSmokefoot (talk | contribs)Autopatrolled, Extended confirmed users, Pending changes reviewers, Rollbackers74,495 edits →Preparation: rephrase 
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⚫ {{Use dmy dates|date=March 2021}}
{{Short description|Pair of enantiomers}}
{{distinguish|Citronellal}}

{{chembox {{chembox
| Verifiedfields = changed
| Watchedfields = changed | Watchedfields = changed
| verifiedrevid = 407462954 | verifiedrevid = 443528686
| Name = Citronellol | Name = Citronellol
| ImageFile = Citronellol enantiomers.svg | ImageFile = Citronellol enantiomers.svg
| ImageSize = 200px | ImageSize = 250px
| ImageAlt = Skeletal formula of (+)-citronellol and (−)-citronellol
⚫ | ImageName = Citronellol
| ImageCaption = (+)-Citronellol (left) and (-)-citronellol | ImageCaption = (+)-Citronellol (left) and (−)-citronellol (right)
| ImageFile1 = (+)-Citronellol 3D ball.png
⚫ | IUPACName = 3,7-Dimethyloct-6-en-1-ol
| ImageAlt1 = Ball-and-stick model of the (+)-citronellol molecule
⚫ | OtherNames = (±)-β-Citronellol; <br> 3,7-Dimethyl-6-octen-1-ol
⚫ | ImageCaption1 = ''R''-(+)-Citronellol
| ImageFile2 = (-)-Citronellol 3D ball.png
| ImageAlt2 = Ball-and-stick model of the (−)-citronellol molecule
| ImageCaption2 = ''S''-(−)-Citronellol
⚫ | IUPACName = 3,7-Dimethyloct-6-en-1-ol
⚫ | OtherNames = (±)-β-Citronellol; Cephrol, Corol
| Section1 = {{Chembox Identifiers | Section1 = {{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 13850135 | ChemSpiderID = 13850135
| UNII_Ref = {{fdacite|correct|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = P01OUT964K | UNII = 565OK72VNF
| KEGG_Ref = {{keggcite|changed|kegg}} | UNII1_Ref = {{fdacite|correct|FDA}}
| UNII1 = P01OUT964K
| UNII1_Comment = (''R'')
| UNII2_Ref = {{fdacite|correct|FDA}}
| UNII2 = 8RSY5Y5658
| UNII2_Comment = (''S'')

| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C09849 | KEGG = C09849
| InChI = 1/C10H20O/c1-9(2)5-4-6-10(3)7-8-11/h5,10-11H,4,6-8H2,1-3H3/t10-/m1/s1 | InChI = 1/C10H20O/c1-9(2)5-4-6-10(3)7-8-11/h5,10-11H,4,6-8H2,1-3H3/t10-/m1/s1
Line 30: Line 46:
| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 106-22-9 | CASNo = 106-22-9
| ChEBI_Ref = {{ebicite|changed|EBI}} | CASNo1_Ref = {{cascite|correct|CAS}}
| CASNo1 = 1117-61-9
| CASNo1_Comment =(''R'')
| CASNo2_Ref = {{cascite|correct|CAS}}
| CASNo2 = 7540-51-4
| CASNo2_Comment =(''S'')

| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 50462 | ChEBI = 50462
| PubChem = 8842
| EC_number = 247-737-6
| Beilstein = 1362474
| SMILES = OCC(CC/C=C(/C)C)C | SMILES = OCC(CC/C=C(/C)C)C
}} }}
| Section2 = {{Chembox Properties | Section2 = {{Chembox Properties
| C=10|H=20|O=1 | C=10|H=20|O=1
| MolarMass = 156.27 g/mol | Density = 0.855 g/cm<sup>3</sup>
⚫ | BoilingPtC = 225
| Density = 0.855 g/cm<sup>3</sup>
| Viscosity = 11.1 mPa&nbsp;s
| MeltingPt =
⚫ }}
⚫ | BoilingPtC = 225
| Section3 = {{Chembox Hazards
⚫ }}
| NFPA-H = 1
| NFPA-F = 2
| NFPA-R = 0
| GHSPictograms = {{GHS07}}{{GHS09}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|315|317|319}}
| PPhrases = {{P-phrases|261|264|272|273|280|302+352|305+351+338|321|332+313|333+313|337+313|362|363|391|501}}
}}
}} }}


'''Citronellol''', or dihydrogeraniol, is a natural acyclic ]. Both ]s occur in nature. (+)-Citronellol, which is found in ]s, including '']'' (50%), is the more common isomer. (−)-Citronellol is found in the oils of ] (18-55%) and '']'' geraniums.<ref>Lawless, J., ''The Illustrated Encyclopedia of Essential Oils'' ISBN 1-85230-661-0</ref> '''Citronellol''', or dihydrogeraniol, is a natural acyclic mono]. Both ]s occur in nature. (+)-Citronellol, which is found in ]s, including '']'' (50%), is the more common isomer. (−)-Citronellol is widespread, but particularly abundant in the oils of ] (18–55%) and '']'' geraniums.<ref>{{cite book | last= Lawless |first=J. | title = The Illustrated Encyclopedia of Essential Oils | isbn = 978-1-85230-661-8| year = 1995 }}</ref>


==Preparation==
Citronellol is used in perfumes and insect repellents,<ref>{{cite journal | author = Taylor WG, Schreck CE. | title = Chiral-phase capillary gas chromatography and mosquito repellent activity of some oxazolidine derivatives of (+)- and (-)-citronellol | journal = J Pharm Sci. | year = 1985 | volume = 74 | issue = 5 | pages = 534–539 | doi = 10.1002/jps.2600740508 | pmid = 2862274}}</ref> and as a mite attractant.<ref name = usepa></ref> It is also a raw material for the production of ]. The United States FDA considers citronellol as ] (GRAS) for food use.<ref name = usepa/> Citronellol should be avoided by people with perfume allergy.<ref></ref>
Several million kilograms of citronellol are produced annually. It is mainly obtained by partial ] of ] or ] over ] catalyst.<ref name=KO>{{cite book |doi=10.1002/0471238961.2005181602120504.a01.pub2|chapter=Terpenoids |title=Kirk-Othmer Encyclopedia of Chemical Technology |year=2006 |last1=Sell |first1=Charles S. |isbn=0471238961 }}</ref> Hydrogenation of both C=C bonds using a nickel catalyst gives tetrahydro], yet another commercial fragrance.<ref>{{cite book |doi=10.1002/14356007.t11_t01 |chapter=Flavors and Fragrances, 2. Aliphatic Compounds |title=Ullmann's Encyclopedia of Industrial Chemistry |date=2015 |last1=Panten |first1=Johannes |last2=Surburg |first2=Horst |pages=1–55 |isbn=978-3-527-30673-2 }}</ref>

] have been investigated for the production of ]s.<ref>{{cite book | first= Robert H. |last=Morris | chapter = Ruthenium and Osmium | title = The Handbook of Homogeneous Hydrogenation | editor1-first = J. G. |editor1-last=De Vries |editor2-first= C. J. |editor2-last=Elsevier | year = 2007 | publisher = Wiley-VCH | location = Weinheim | isbn = 978-3-527-31161-3}}</ref><ref>{{Cite journal | doi = 10.1016/0957-4166(95)00015-H | title = Catalytic Synthesis of (''R'')- and (''S'')-citronellol by homogeneous hydrogenation over amidophosphinephosphinite and diaminodiphosphine rhodium complexes | year = 1995 | last1 = Ait Ali | first1 = M. | last2 = Allaoud | first2 = S. | last3 = Karim | first3 = A. | last4 = Roucoux | first4 = A. | last5 = Mortreux | first5 = A. | journal = Tetrahedron: Asymmetry | volume = 6 | issue = 2 | pages = 369}}</ref>

==Uses==
Citronellol is used in perfumes and as a fragrance in cleaning products. In many applications, one of the enantiomers is preferred. It is a component of citronella oil, an insect repellant.<ref name=KO/>

Citronellol is used as a raw material for the production of ].<ref name=KO/><ref>{{cite journal | title="Dark" Singlet Oxygenation of β-Citronellol: A Key Step in the Manufacture of Rose Oxide | journal=Organic Process Research & Development | doi=10.1021/op900076g | volume=14 | year=2010 | pages=259–262 | last1 = Alsters | first1 = Paul L. | last2 = Jary | first2 = Walther | last3 = Aubry | first3 = Jean-Marie}}</ref> It is also a precursor to many commercial and potential fragrances such as citronellol acetate, citronellyl oxyacetaldehyde, citronellyl methyl acetal, and ethyl citronellyl oxalate.<ref name=KO/>

==Health and safety==
The United States FDA considers citronellol as ] (GRAS) for food use.<ref name = usepa>{{cite web|url=http://www.epa.gov/pesticides/biopesticides/ingredients/factsheets/factsheet_167004.htm|title=Redirect|work=epa.gov|accessdate=29 July 2015}}</ref> Citronellol is subject to restrictions on its use in perfumery,<ref>{{cite web |url=http://www.ifraorg.org/en-us/standards_restricted/s3/p3 |title=Standards Restricted - IFRA International Fragrance Association |accessdate=19 July 2012 |url-status=dead |archiveurl=https://web.archive.org/web/20120106222844/http://www.ifraorg.org/en-us/standards_restricted/s3/p3 |archivedate=6 January 2012 }}</ref> as some people may become sensitised to it, but the degree to which citronellol can cause an allergic reaction in humans is disputed.<ref>{{Cite web |url=http://www.leffingwell.com/Cropwatch%20Claims%20Victory%20Over%2026%20Allergens.pdf |title=Cropwatch Report April 2008 |access-date=19 July 2012 |archive-url=https://web.archive.org/web/20140210163144/http://www.leffingwell.com/Cropwatch%20Claims%20Victory%20Over%2026%20Allergens.pdf |archive-date=10 February 2014 |url-status=dead }}</ref><ref> {{webarchive|url=https://web.archive.org/web/20070927205013/http://www2.mst.dk/common/Udgivramme/Frame.asp?pg=http%3A%2F%2Fwww2.mst.dk%2Fudgiv%2Fpublications%2F2006%2F87-7052-278-2%2Fhtml%2Fkap07_eng.htm |date=27 September 2007 }}</ref>

In terms of dermal safety, citronellol has been evaluated as an insect repellent.<ref>{{cite journal | last1= Taylor |first1=W. G. |last2=Schreck |first2=C. E. | title = Chiral-phase capillary gas chromatography and mosquito repellent activity of some oxazolidine derivatives of (+)- and (−)-citronellol | journal = Journal of Pharmaceutical Sciences| year = 1985 | volume = 74 | issue = 5 | pages = 534–539 | doi = 10.1002/jps.2600740508 | pmid = 2862274| url = https://zenodo.org/record/1229253}}</ref> <!--very niche and as a mite attractant.<ref name = usepa>{{cite web|url=http://www.epa.gov/pesticides/biopesticides/ingredients/factsheets/factsheet_167004.htm|title=Redirect|work=epa.gov|accessdate=29 July 2015}}</ref> Citronellol is a good mosquito repellent at short distances, but protection greatly lessens when the subject is slightly further from the source.<ref>{{Cite journal | doi = 10.1016/j.actatropica.2013.03.011 | title = Reduction of mosquito biting-pressure: Spatial repellents or mosquito traps? A field comparison of seven commercially available products in Israel | year = 2013 | last1 = Revay | first1 = Edita E. | last2 = Kline | first2 = Daniel L. | last3 = Xue | first3 = Rui-De | last4 = Qualls | first4 = Whitney A. | last5 = Bernier | first5 = Ulrich R. | last6 = Kravchenko | first6 = Vasiliy D. | last7 = Ghattas | first7 = Nina | last8 = Pstygo | first8 = Irina | last9 = Müller | first9 = Günter C. | journal = Acta Tropica | volume = 127 | pages = 63–68 | pmid = 23545129 | issue = 1}}</ref> When complexed with β-], it has on average a 90-minute protection duration against mosquitoes.<ref>{{cite journal | doi = 10.1007/s10847-011-9985-7 | title = Investigation of inclusion complexes of citronella oil, citronellal and citronellol with β-cyclodextrin for mosquito repellent | year = 2011 | last1 = Songkro | first1 = Sarunyoo | last2 = Hayook | first2 = Narissara | last3 = Jaisawang | first3 = Jittarat | last4 = Maneenuan | first4 = Duangkhae | last5 = Chuchome | first5 = Thitima | last6 = Kaewnopparat | first6 = Nattha | journal = Journal of Inclusion Phenomena and Macrocyclic Chemistry | volume = 72 | issue = 3–4 | pages = 339| s2cid = 93566912 }}</ref>-->


==See also== ==See also==
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* ] * ]
* ] * ]
* ] * '']''
* ] * ] (allergy)


== References== ==References==
{{Reflist}} {{Reflist}}
⚫ {{Use dmy dates|date=January 2011}}


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