出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2016/12/17 23:46:23」(JST)
Names | |
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IUPAC name
Undec-10-enoic acid
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Other names
10-Undecenoic acid
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Identifiers | |
CAS Number
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112-38-9 Y |
3D model (Jmol) | Interactive image |
ChEBI | CHEBI:35045 Y |
ChemSpider | 10771160 Y |
ECHA InfoCard | 100.003.605 |
MeSH | Undecylenic+acid |
PubChem | 5634 |
UNII | K3D86KJ24Nk N |
InChI
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SMILES
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Properties | |
Chemical formula
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C11H20O2 |
Molar mass | 184.28 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
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D01AE04 (WHO) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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N verify (what is YN ?) | |
Infobox references | |
Undecylenic acid is an organic compound unsaturated 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, but it is also a precursor in the manufacture of pharmaceuticals, personal hygiene products, cosmetics, and perfumes.[1] salts and esters of undecylenic acid are known as undecylenates.
It is prepared by pyrolysis of ricinoleic acid, which is derived from castor oil. Specifically, the methyl ester of ricinoleic acid 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.
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]
This article needs more 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. (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,[5] or other generalized infections by Candida albicans.[medical citation needed] When used for tinea cruris, it can result in extreme burning.[medical citation needed] In some case studies of tinae versicolor, pain and burning result from fungicide application.
In an older 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."[6][needs update]
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.
Undecylenic acid is approved by the U.S. FDA for topical route and lists in Inactive Ingredient Database.[5][needs update]
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).[7]
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Antifungals (D01 and J02)
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