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{{chembox |
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{{chembox |
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| verifiedrevid = 419091773 |
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| verifiedrevid = 470619622 |
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| Name = |
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|ImageFile=Undecylenic acid.png |
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| ImageFile = Undecylenic acid.svg |
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|ImageSize=200px |
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| ImageClass = skin-invert-image |
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|IUPACName=undec-10-enoic acid |
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| PIN = Undec-10-enoic acid |
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|OtherNames= |
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| OtherNames = 10-Undecenoic acid |
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|Section1= {{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| Section1 = {{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 10771160 |
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| ChemSpiderID = 10771160 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII_Ref = {{fdacite|changed|FDA}} |
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| UNII = K3D86KJ24N |
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| UNII = K3D86KJ24N |
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| InChI = 1/C11H20O2/c1-2-3-4-5-6-7-8-9-10-11(12)13/h2H,1,3-10H2,(H,12,13) |
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| InChI = 1/C11H20O2/c1-2-3-4-5-6-7-8-9-10-11(12)13/h2H,1,3-10H2,(H,12,13) |
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| StdInChIKey = FRPZMMHWLSIFAZ-UHFFFAOYSA-N |
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| StdInChIKey = FRPZMMHWLSIFAZ-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo=112-38-9 |
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| CASNo = 112-38-9 |
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| PubChem=5634 |
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| PubChem = 5634 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 35045 |
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| ChEBI = 35045 |
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| SMILES=C=CCCCCCCCCC(=O)O |
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| SMILES=C=CCCCCCCCCC(=O)O |
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| MeSHName=Undecylenic+acid |
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| MeSHName=Undecylenic+acid |
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|Section2= {{Chembox Properties |
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| Section2 = {{Chembox Properties |
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| C = 11 |
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| C=11 | H=20 | O=2 |
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| H = 20 |
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| Appearance = |
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| O = 2 |
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| Density = 0.912 g/mL |
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| MeltingPtC = 23 |
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| Appearance= |
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| BoilingPtC = 275 |
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|Section3= {{Chembox Hazards |
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| FlashPt= |
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| Section6 = {{Chembox Pharmacology |
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| Autoignition= |
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| ATCCode_prefix = D01 |
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| ATCCode_suffix = AE04 |
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| Section7 = {{Chembox Hazards |
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'''Undecylenic acid''' is an ] with the formula CH<sub>2</sub>=CH(CH<sub>2</sub>)<sub>8</sub>CO<sub>2</sub>H. It is an ] ]. It is a colorless oil. Undecylenic acid is mainly used for the production of ] and in the treatment of fungal infections of the skin, but it is also a precursor in the manufacture of many ], personal hygiene products, ], and perfumes.<ref name=Ullmann/> ] and ]s of undecylenic acid are known as '''undecylenates'''. |
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'''Undecylenic acid''' is an ] ] ] derived from ]. It is the common name of the '''10-undecenoic acid''', (CH<sub>2</sub>CH(CH<sub>2</sub>)<sub>8</sub>COOH). It is used in the manufacture of ], ] and perfumery, including antidandruff shampoos, antimicrobial powders and as a musk in perfumes and aromas.<ref>{{cite web | title=United States International Trade Commission Memorandum | url=http://www.usitc.gov/tata/hts/other/rel_doc/bill_reports/106c/hr-3762.pdf | format=PDF | publisher=USITC | accessdate=2007-01-02 |archiveurl = http://web.archive.org/web/20060924201130/http://www.usitc.gov/tata/hts/other/rel_doc/bill_reports/106c/hr-3762.pdf <!-- Bot retrieved archive --> |archivedate = 2006-09-24}} - see page 2 of link</ref> Undecylenic acid is produced by ] of castor oil under pressure.<ref>{{cite journal | title=Undecylenic Acid in Psoriasis | journal =CMAJ | pmid = 18140580 | accessdate=2007-01-05 | year=1992 | last1=Katz | first1=G | last2=Watt | first2=JA | volume=37 | issue=3 | pages=173–8 | pmc=1591667}} - see page 2/362 of link</ref> |
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==Medicinal uses== |
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==Preparation== |
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Undecylenic acid is prepared by ] of ], which is derived from ]. Specifically, the ] ] of ricinoleic acid is ] to yield both undecylenic acid and ]. The process is conducted at 500–600 °C in the presence of steam.<ref name=Ullmann>David J. Anneken, Sabine Both, Ralf Christoph, Georg Fieg, Udo Steinberner, Alfred Westfechtel "Fatty Acids" in ''Ullmann's Encyclopedia of Industrial Chemistry'', 2006, Wiley-VCH, Weinheim. {{doi|10.1002/14356007.a10_245.pub2}}</ref><ref>{{Cite book | author = A. Chauvel, G. Lefebvre| title = Petrochemical Processes: Technical and Economic Characteristics | chapter = Chapter 2 | page = 277 | location = Paris | date = 1989 | isbn = 2-7108-0563-4}}</ref> The methyl ester is then ]. |
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Undecylenic acid is a natural fungicide and is FDA approved in over-the-counter medications for skin disorders. It is the active ingredient in medications for skin infections, and relieves itching, burning, and irritation. For example, it is used against ], such as ], ], jock itch or '']''.<ref>{{cite web | title=Ingredient List P-Z | url=http://www.fda.gov/cder/Offices/OTC/Ingredient_List_P-Z.pdf | format=PDF | publisher=FDA | accessdate=2007-01-02 |archiveurl = http://web.archive.org/web/20061016115347/http://www.fda.gov/cder/Offices/OTC/Ingredient_List_P-Z.pdf <!-- Bot retrieved archive --> |archivedate = 2006-10-16}} - see page 65 of this link</ref> When used for jock itch, it can result in extreme burning, as the skin is rather sensitive. |
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It is also used in the treatment of ].<ref>{{cite web | title=Undecylenic Acid in Psoriasis | url=http://www.pubmedcentral.nih.gov/picrender.fcgi?artid=1591667&blobtype=pdf | format=PDF | publisher=CMAJ | accessdate=2007-01-05}} - see page 4/364 of link</ref> |
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Undecylenic acid has antiviral properties that are effective on skin infections such as ].<ref>{{cite journal | title=Effect of undecylenic acid as a topical microbicide against genital herpes infection in mice and guinea pigs | format= | journal = Antiviral Res | year = 1999 | volume = 40 | issue = 3 | pages = 139–44 | pmid = 10027648 | accessdate=2007-01-18 | doi=10.1016/S0166-3542(98)00055-2 | author=Bourne, N | last2=Ireland | first2=J | last3=Stanberry | first3=LR | last4=Bernstein | first4=DI}}</ref> |
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The mechanism of action is unknown.<ref name="urlantifung">{{cite web |url=http://faculty.swosu.edu/scott.long/phcl/antifung.htm |title=Anti-Fungals |work= |accessdate=2008-07-09}}</ref> |
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==Other uses== |
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==General commercial uses== |
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Undecylenic acid is converted to ] on an industrial scale. This aminocarboxylic acid is the precursor to Nylon-11.<ref name=Ullmann/> |
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Undecylenic acid can be used in silicon-based biosensors. Monolayers can be made on bare silicon transducer surfaces with the help of covalent bonds between silicon atom and the double bonds of undecylenic acid. The ] groups remain available for the ] of biomolecules such as DNA or proteins.<ref>{{cite journal | doi = 10.1021/jp7119922 | author = A. Moraillon, A. C. Gouget-Laemmel, F. Ozanam, and J.-N. Chazalviel | title = Amidation of Monolayers on Silicon in Physiological Buffers: A Quantitative IR Study | journal = J. Phys. Chem. C | year = 2008 | volume = 112 | issue = 18 | pages = 7158–7167}}</ref> |
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Undecylenic acid is reduced to undecylene aldehyde, which is valued in perfumery. The acid is first converted to the ], which allows selective reduction.<ref>{{Ullmann | author = Christian Kohlpaintner, Markus Schulte, Jürgen Falbe, Peter Lappe, Jürgen Weber | title = Aldehydes, Aliphatic | doi = 10.1002/14356007.a01_321.pub2}}</ref> |
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===Medical uses=== |
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{{more medical citations needed|date=July 2015}} |
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Undecylenic acid is an active ingredient in medications for skin infections, and to relieve itching, burning, and irritation associated with skin problems. For example, it is used against ], such as ], ], ],<ref name=fda/> or other generalized infections by '']''.<ref name="pmid26902505">{{cite journal|last1=Shi|first1=Dongmei|last2=Zhao|first2=Yaxin|last3=Yan|first3=Hongxia|last4=Fu|first4=Hongjun|last5=Shen|first5=Yongnian|last6=Lu|first6=Guixia|last7=Mei|first7=Huan|last8=Qiu|first8=Ying|last9=Li|first9=Dongmei|last10=Liu|first10=Weida|title=Antifungal effects of undecylenic acid on the biofilm formation of Candida albicans|journal=International Journal of Clinical Pharmacology and Therapeutics|date=1 May 2016|volume=54|issue=5|pages=343–353|doi=10.5414/CP202460 |pmid=26902505}}</ref> When used for ], it can result in extreme burning.{{medcn|date=July 2015}} In some case studies of tinea versicolor, pain and burning result from fungicide application. In a review of placebo-controlled trials, undecenoic acid was deemed efficacious, alongside prescription azoles (e.g., ]) and allylamines (e.g., ]<ref>{{cite journal|last1=Crawford|first1=F|last2=Hollis|first2=S|title=Topical treatments for fungal infections of the skin and nails of the foot.|journal=The Cochrane Database of Systematic Reviews|date=18 July 2007|volume=2007|issue=3|pages=CD001434|doi=10.1002/14651858.CD001434.pub2|pmid=17636672|pmc=7073424}}</ref>). Undecylenic acid is also a precursor to antidandruff shampoos and antimicrobial powders.<ref>{{cite web | title=United States International Trade Commission Memorandum | url=http://www.usitc.gov/tata/hts/other/rel_doc/bill_reports/106c/hr-3762.pdf | publisher=USITC | access-date=2007-01-02 |archive-url = https://web.archive.org/web/20060924201130/http://www.usitc.gov/tata/hts/other/rel_doc/bill_reports/106c/hr-3762.pdf <!-- Bot retrieved archive --> |archive-date = 2006-09-24}} - see page 2 of link.{{verify source|date=July 2015}}</ref> |
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In terms of the mechanism underlying its antifungal effects against ''Candida albicans'', undecylenic acid inhibits morphogenesis. In a study on denture liners, undecylenic acid in the liners was found to inhibit conversion of yeast to the ] (which are associated with active infection), via inhibition of fatty acid biosynthesis. The mechanism of action and effectiveness in fatty acid-type antifungals is dependent on the number of carbon atoms in the chain, with efficacy increasing with the number of atoms in the chain.{{citation needed|date=November 2023}} |
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===U.S. FDA approval=== |
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Undecylenic acid is approved by the U.S. ] for topical route and is listed in the Code of Federal Regulations.<ref name=fda> CFR Title 21, Volume 5, Chapter 1, Subchapter D, Part 333, Subpart C, Sec. (§333.210)</ref> |
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==Research uses== |
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Undecylenic acid has been used as a linking molecule, because it is a ]. Specifically it is an α,ω- (terminally ]) bifunctional agent. For instance, the title compound has been used to prepare silicon-based biosensors, linking silicon transducer surfaces to the terminal double bond of undecylenic acid (forming an Si-C bond), leaving the ] groups available for ] of biomolecules (e.g., proteins).<ref>{{cite journal | doi = 10.1021/jp7119922 |author1=A. Moraillon |author2=A. C. Gouget-Laemmel |author3=F. Ozanam |author4=J.-N. Chazalviel |name-list-style=amp | title = Amidation of Monolayers on Silicon in Physiological Buffers: A Quantitative IR Study | journal = J. Phys. Chem. C | year = 2008 | volume = 112 | issue = 18 | pages = 7158–7167}}</ref>{{primary source inline|date=July 2015}} |
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== See also == |
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* ] |
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==References== |
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==References== |
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{{reflist}} |
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{{reflist}} |
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{{Antifungals}} |
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{{Antifungals}} |
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McLain N, Ascanio R, Baker C, et al. Undecylenic acid inhibits morphogenesis of |
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Candida albicans. Antimicrob Agents |
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Chemother 2000;44:2873-2875 |
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