Undecylenic acid: Difference between revisions

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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 [[mycosis|fungal skin infections]], such as [[athlete's foot]], [[ringworm]], [[tinea cruris]],<ref name=fda/> or other generalized infections by ''[[Candida albicans]]''.<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=05|pages=343–353|doi=10.5414/CP202460 |pmid=26902505}}</ref> When used for [[tinea cruris]], it can result in extreme burning.{{mcn|date=July 2015}} In some case studies of tinae versicolor, pain and burning result from fungicide application.
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 [[mycosis|fungal skin infections]], such as [[athlete's foot]], [[ringworm]], [[tinea cruris]],<ref name=fda/> or other generalized infections by ''[[Candida albicans]]''.<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=05|pages=343–353|doi=10.5414/CP202460 |pmid=26902505}}</ref> When used for [[tinea cruris]], it can result in extreme burning.{{mcn|date=July 2015}} In some case studies of tinae 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]].<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|issue=3|pages=CD001434|doi=10.1002/14651858.CD001434.pub2|pmid=17636672}}</ref>

In a review of placebo-controlled trials, undecenoic acid was deemed efficacious, alongside prescription azoles (e.g., [[clotrimazole]]) and allylamines (e.g., [[terbinafine]]), though there were not "sufficient comparative trials to judge relative efficacy."<ref>{{cite journal | pmid = 10796792| year = 2000| author1 = Crawford| first1 = F| title = Cochrane Database of Systematic Reviews| journal = The Cochrane database of systematic reviews| issue = 2| pages = CD001434| last2 = Hart| first2 = R| last3 = Bell-Syer| first3 = S| last4 = Torgerson| first4 = D| last5 = Young| first5 = P| last6 = Russell| first6 = I| doi = 10.1002/14651858.CD001434| chapter = Topical treatments for fungal infections of the skin and nails of the foot}}</ref>{{Update inline|reason=Updated version https://www.ncbi.nlm.nih.gov/pubmed/17636672|date=December 2016}}


One of mechanisms underlying its antifungal effects against ''Candida albicans'' is its inhibition of morphogenesis. In a study on denture liners, undecylenic acid in the liners was found to inhibit conversion of yeast to the [[hypha| 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.
One of mechanisms underlying its antifungal effects against ''Candida albicans'' is its inhibition of morphogenesis. In a study on denture liners, undecylenic acid in the liners was found to inhibit conversion of yeast to the [[hypha| 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.

Revision as of 03:20, 24 July 2017

Undecylenic acid
Names
IUPAC name
Undec-10-enoic acid
Other names
10-Undecenoic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.003.605 Edit this at Wikidata
MeSH Undecylenic+acid
UNII
  • InChI=1S/C11H20O2/c1-2-3-4-5-6-7-8-9-10-11(12)13/h2H,1,3-10H2,(H,12,13) checkY
    Key: FRPZMMHWLSIFAZ-UHFFFAOYSA-N checkY
  • InChI=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
  • C=CCCCCCCCCC(=O)O
Properties
C11H20O2
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
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 checkY☒N ?)

Undecylenic acid is an organic compound with the formula CH2=CH(CH2)8CO2H. It is an unsaturated fatty acid and forms a colorless oil at room temperature and pressure. 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.

Preparation

Undecylenic acid is prepared by pyrolysis of ricinoleic acid, which is derived from castor oil. Specifically, the methyl ester of ricinoleic acid is subjected to the chemical process of cracking 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
Pyrolyse von Ricinolsäuremethylester

General commercial uses

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 via its acid chloride to the aldehyde undecylene aldehyde, which is valued in perfumery.[3] Undecylenic acid is also a precursor to antidandruff shampoos and antimicrobial powders.[4]

Medical uses

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,[5] or other generalized infections by Candida albicans.[6] When used for tinea cruris, it can result in extreme burning.

In some case studies of tinae 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.[7]

One of mechanisms underlying its antifungal effects against Candida albicans is its inhibition of 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.

FDA approval

Undecylenic acid is approved by the U.S. FDA for topical route and is listed in the Inactive Ingredient Database.[5][needs update]

Research uses

Undecylenic acid has been used as a linking molecule, because it is a bifunctional compound, in this case, 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]

References

  1. ^ 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
  2. ^ A. Chauvel, G. Lefebvre (1989). "Chapter 2". Petrochemical Processes: Technical and Economic Characteristics. Paris. p. 277. ISBN 2-7108-0563-4.{{cite book}}: CS1 maint: location missing publisher (link)
  3. ^ Christian Kohlpaintner, Markus Schulte, Jürgen Falbe, Peter Lappe, Jürgen Weber. "Aldehydes, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a01_321.pub2. ISBN 978-3527306732.{{cite encyclopedia}}: CS1 maint: multiple names: authors list (link)
  4. ^ "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]
  5. ^ a b "Ingredient List P-Z" (PDF). FDA (see page 65 of this link). Archived from the original (PDF) on 2006-10-16. Retrieved 2006-12-28.[needs update]
  6. ^ 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 (05): 343–353. doi:10.5414/CP202460. PMID 26902505.
  7. ^ 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 (3): CD001434. doi:10.1002/14651858.CD001434.pub2. PMID 17636672.
  8. ^ 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. {{cite journal}}: Unknown parameter |last-author-amp= ignored (|name-list-style= suggested) (help)[non-primary source needed]
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