Undecylenic acid

Structural formula
General
Surname	Undecylenic acid
other names	Undec-10-enoic acid; Undecenoic acid; Hendecenoic acid (outdated);
Molecular formula	C 11 H 20 O 2
Brief description	Liquid, colorless mass with a rancid odor
External identifiers / databases
EC number	203-965-8
ECHA InfoCard	100.003.605
PubChem	5634
Wikidata	Q420346
Drug information
ATC code	D01 AE04
properties
Molar mass	184.28g mol −1
Physical state	firmly
density	0.91 g cm −3 (20 ° C)
Melting point	24.5 ° C ° C
boiling point	275 ° C
solubility	low in water (74 mg l −1 at 20 ° C)
Refractive index	1.4486 (24 ° C)
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances Caution
H and P phrases	H: 315-319-412
	P: 273-280-302 + 352-305 + 351 + 338
	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.

[MERCK-1] Data sheet 10-undecenoic acid (PDF) from Merck , accessed on April 25, 2011.

[ALFA-2] Data sheet undecylenic acid at AlfaAesar, accessed on March 30, 2010 ( PDF )(JavaScript required) .

[CRC90_3_516-3] 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.

[GESTIS-4] Entry on 10-undecenoic acid in the GESTIS substance database of the IFA , accessed on July 23, 2016(JavaScript required) .

[5] Undecenoic acid at PlantFA Database, accessed November 29, 2017.