Undecylenic acid is an organic compound with the formula CH2=CH(CH2)8CO2H. It is an unsaturatedfatty acid. It is a colorless oil. Undecylenic acid is mainly used for the production of Nylon-11 and in the treatment of fungal infections of the skin, but it is also a precursor in the manufacture of many pharmaceuticals, personal hygiene products, cosmetics, and perfumes.[1]Salts and esters of undecylenic acid are known as undecylenates.
Undecylenic acid is prepared by pyrolysis of ricinoleic acid, which is derived from castor oil. Specifically, the methylester of ricinoleic acid is cracked to yield both undecylenic acid and heptanal. The process is conducted at 500–600 °C in the presence of steam.[1][2] The methyl ester is then hydrolyzed.
Pyrolyse von Ricinolsäuremethylester
General commercial usesedit
Undecylenic acid is converted to 11-aminoundecanoic acid on an industrial scale. This aminocarboxylic acid is the precursor to Nylon-11.[1]
Undecylenic acid is reduced to undecylene aldehyde, which is valued in perfumery. The acid is first converted to the acid chloride, which allows selective reduction.[3]
Medical usesedit
This article needs more reliable medical references for verification or relies too heavily on primary sources. Please review the contents of the article and add the appropriate references if you can. Unsourced or poorly sourced material may be challenged and removed. Find sources: "Undecylenic acid" – news · newspapers · books · scholar · JSTOR(July 2015)
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 fungal skin infections, such as athlete's foot, ringworm, tinea cruris,[4] or other generalized infections by Candida albicans.[5] When used for tinea cruris, it can result in extreme burning.[medical citation needed] 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., clotrimazole) and allylamines (e.g., terbinafine[6]). Undecylenic acid is also a precursor to antidandruff shampoos and antimicrobial powders.[7]
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 hyphal form (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]
U.S. FDA approvaledit
Undecylenic acid is approved by the U.S. FDA for topical route and is listed in the Code of Federal Regulations.[4]
Research usesedit
Undecylenic acid has been used as a linking molecule, because it is a bifunctional compound. Specifically it is an α,ω- (terminally functionalized) 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 carboxylic acid groups available for conjugation of biomolecules (e.g., proteins).[8][non-primary source needed]
^ abPublisher FDA CFR Title 21, Volume 5, Chapter 1, Subchapter D, Part 333, Subpart C, Sec. (§333.210)
^Shi, Dongmei; Zhao, Yaxin; Yan, Hongxia; Fu, Hongjun; Shen, Yongnian; Lu, Guixia; Mei, Huan; Qiu, Ying; Li, Dongmei; Liu, Weida (1 May 2016). "Antifungal effects of undecylenic acid on the biofilm formation of Candida albicans". International Journal of Clinical Pharmacology and Therapeutics. 54 (5): 343–353. doi:10.5414/CP202460. PMID 26902505.
^Crawford, F; Hollis, S (18 July 2007). "Topical treatments for fungal infections of the skin and nails of the foot". The Cochrane Database of Systematic Reviews. 2007 (3): CD001434. doi:10.1002/14651858.CD001434.pub2. PMC7073424. PMID 17636672.
^(PDF). USITC. Archived from the original (PDF) on 2006-09-24. Retrieved 2007-01-02. - see page 2 of link.[verification needed]
^A. Moraillon; A. C. Gouget-Laemmel; F. Ozanam & J.-N. Chazalviel (2008). "Amidation of Monolayers on Silicon in Physiological Buffers: A Quantitative IR Study". J. Phys. Chem. C. 112 (18): 7158–7167. doi:10.1021/jp7119922.
McLain N, Ascanio R, Baker C, et al. Undecylenic acid inhibits morphogenesis of Candida albicans. Antimicrob Agents Chemother 2000;44:2873-2875
January 01, 1970
undecylenic, acid, organic, compound, with, formula, 8co2h, unsaturated, fatty, acid, colorless, mainly, used, production, nylon, treatment, fungal, infections, skin, also, precursor, manufacture, many, pharmaceuticals, personal, hygiene, products, cosmetics, . Undecylenic acid is an organic compound with the formula CH2 CH CH2 8CO2H It is an unsaturated fatty acid It is a colorless oil Undecylenic acid is mainly used for the production of Nylon 11 and in the treatment of fungal infections of the skin but it is also a precursor in the manufacture of many pharmaceuticals personal hygiene products cosmetics and perfumes 1 Salts and esters of undecylenic acid are known as undecylenates Undecylenic acid Names Preferred IUPAC name Undec 10 enoic acid Other names 10 Undecenoic acid Identifiers CAS Number 112 38 9 Y 3D model JSmol Interactive image ChEBI CHEBI 35045 Y ChemSpider 10771160 Y ECHA InfoCard 100 003 605 MeSH Undecylenic acid PubChem CID 5634 UNII K3D86KJ24N N CompTox Dashboard EPA DTXSID8035001 InChI InChI 1S C11H20O2 c1 2 3 4 5 6 7 8 9 10 11 12 13 h2H 1 3 10H2 H 12 13 YKey FRPZMMHWLSIFAZ UHFFFAOYSA N YInChI 1 C11H20O2 c1 2 3 4 5 6 7 8 9 10 11 12 13 h2H 1 3 10H2 H 12 13 Key FRPZMMHWLSIFAZ UHFFFAOYAJ SMILES C CCCCCCCCCC O O Properties Chemical formula C 11H 20O 2 Molar mass 184 279 g mol 1 Density 0 912 g mL Melting point 23 C 73 F 296 K Boiling point 275 C 527 F 548 K Pharmacology ATC code D01AE04 WHO Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references Contents 1 Preparation 2 General commercial uses 2 1 Medical uses 2 2 U S FDA approval 3 Research uses 4 See also 5 ReferencesPreparation editUndecylenic acid is prepared by pyrolysis of ricinoleic acid which is derived from castor oil Specifically the methyl ester of ricinoleic acid is cracked to yield both undecylenic acid and heptanal The process is conducted at 500 600 C in the presence of steam 1 2 The methyl ester is then hydrolyzed nbsp Pyrolyse von RicinolsauremethylesterGeneral commercial uses editUndecylenic acid is converted to 11 aminoundecanoic acid on an industrial scale This aminocarboxylic acid is the precursor to Nylon 11 1 Undecylenic acid is reduced to undecylene aldehyde which is valued in perfumery The acid is first converted to the acid chloride which allows selective reduction 3 Medical uses edit This article needs more reliable medical references for verification or relies too heavily on primary sources Please review the contents of the article and add the appropriate references if you can Unsourced or poorly sourced material may be challenged and removed Find sources Undecylenic acid news newspapers books scholar JSTOR July 2015 nbsp 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 fungal skin infections such as athlete s foot ringworm tinea cruris 4 or other generalized infections by Candida albicans 5 When used for tinea cruris it can result in extreme burning medical citation needed 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 clotrimazole and allylamines e g terbinafine 6 Undecylenic acid is also a precursor to antidandruff shampoos and antimicrobial powders 7 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 hyphal form 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 U S FDA approval edit Undecylenic acid is approved by the U S FDA for topical route and is listed in the Code of Federal Regulations 4 Research uses editUndecylenic acid has been used as a linking molecule because it is a bifunctional compound Specifically it is an a w terminally functionalized 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 carboxylic acid groups available for conjugation of biomolecules e g proteins 8 non primary source needed See also editList of unsaturated fatty acidsReferences edit a b c 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 A Chauvel G Lefebvre 1989 Chapter 2 Petrochemical Processes Technical and Economic Characteristics Paris p 277 ISBN 2 7108 0563 4 a href Template Cite book html title Template Cite book cite book a CS1 maint location missing publisher link Christian Kohlpaintner Markus Schulte Jurgen Falbe Peter Lappe Jurgen Weber Aldehydes Aliphatic Ullmann s Encyclopedia of Industrial Chemistry Weinheim Wiley VCH doi 10 1002 14356007 a01 321 pub2 ISBN 978 3527306732 a href Template Cite encyclopedia html title Template Cite encyclopedia cite encyclopedia a CS1 maint multiple names authors list link a b Publisher FDA CFR Title 21 Volume 5 Chapter 1 Subchapter D Part 333 Subpart C Sec 333 210 Shi Dongmei Zhao Yaxin Yan Hongxia Fu Hongjun Shen Yongnian Lu Guixia Mei Huan Qiu Ying Li Dongmei Liu Weida 1 May 2016 Antifungal effects of undecylenic acid on the biofilm formation of Candida albicans International Journal of Clinical Pharmacology and Therapeutics 54 5 343 353 doi 10 5414 CP202460 PMID 26902505 Crawford F Hollis S 18 July 2007 Topical treatments for fungal infections of the skin and nails of the foot The Cochrane Database of Systematic Reviews 2007 3 CD001434 doi 10 1002 14651858 CD001434 pub2 PMC 7073424 PMID 17636672 United States International Trade Commission Memorandum PDF USITC Archived from the original PDF on 2006 09 24 Retrieved 2007 01 02 see page 2 of link verification needed A Moraillon A C Gouget Laemmel F Ozanam amp J N Chazalviel 2008 Amidation of Monolayers on Silicon in Physiological Buffers A Quantitative IR Study J Phys Chem C 112 18 7158 7167 doi 10 1021 jp7119922 McLain N Ascanio R Baker C et al Undecylenic acid inhibits morphogenesis of Candida albicans Antimicrob Agents Chemother 2000 44 2873 2875 Retrieved from https en wikipedia org w index php title Undecylenic acid amp oldid 1221978319, wikipedia, wiki, book, books, library,
