Undecylenic acid
Structural formula | ||||||||||||||||
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General | ||||||||||||||||
Surname | Undecylenic acid | |||||||||||||||
other names |
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Molecular formula | C 11 H 20 O 2 | |||||||||||||||
Brief description |
Liquid, colorless mass with a rancid odor |
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properties | ||||||||||||||||
Molar mass | 184.28g mol −1 | |||||||||||||||
Physical state |
firmly |
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density |
0.91 g cm −3 (20 ° C) |
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Melting point |
24.5 ° C ° C |
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boiling point |
275 ° C |
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solubility |
low in water (74 mg l −1 at 20 ° C) |
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Refractive index |
1.4486 (24 ° C) |
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safety instructions | ||||||||||||||||
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As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C |
Undecylenic acid (10-undecenoic acid) is an odd-numbered and monounsaturated fatty acid which, due to its fungicidal effect, is used in medicine as an antimycotic for the treatment of fungal diseases such as B. Candidosis (thrush) is used. It is made by vacuum distillation of castor oil via the pyrolysis of ricinoleic acid. Undecylenic acid is not soluble in water, but it is miscible with alcohols, chloroform, ether and benzene.
The length of eleven carbon atoms of undecylenic acid represents the optimum for the fungicidal effect observed with many fatty acids. This is due to the fact that the effect increases in principle with length, but again due to the low solubility in water and the consequent reduced bioavailability for longer fatty acids decreases.
Undecylenic acid also occurs naturally; it has been found in considerable amounts in the South Asian salt plant Salicornia brachiata .
literature
- NN: Undecylenic acid. Monograph. In: Aging. Med. Rev. 7 (1), 2002, pp. 68-70, PMID 11896747 .
- N. McLain, R. Ascanio, C. Baker et al .: Undecylenic acid inhibits morphogenesis of Candida albicans. In: Antimicrob Agents Chemother. 44 (10), 2000, pp. 2873-2875, PMID 10991877 , PMC 90168 (free full text).
Individual evidence
- ↑ a b c Data sheet 10-undecenoic acid (PDF) from Merck , accessed on April 25, 2011.
- ↑ Data sheet undecylenic acid at AlfaAesar, accessed on March 30, 2010 ( PDF )(JavaScript required) .
- ↑ a b David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-516.
- ↑ a b Entry on 10-undecenoic acid in the GESTIS substance database of the IFA , accessed on July 23, 2016(JavaScript required) .
- ↑ Undecenoic acid at PlantFA Database, accessed November 29, 2017.