Undecylenic acid

Undecylenic acid
Names

IUPAC name Undec-10-enoic acid
Other names 10-Undecenoic acid
Identifiers
CAS Number	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 CID	5634
UNII	K3D86KJ24Nk^N
InChI InChI=1S/C11H20O2/c1-2-3-4-5-6-7-8-9-10-11(12)13/h2H,1,3-10H2,(H,12,13)^Y Key: FRPZMMHWLSIFAZ-UHFFFAOYSA-N^Y 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
SMILES C=CCCCCCCCCC(=O)O
Properties
Chemical formula	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	D01AE04 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N (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 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.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 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. 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. Undecylenic acid is reduced via its acid chloride to the aldehyde undecylene aldehyde, which is valued in perfumery. Undecylenic acid is also a precursor to antidandruff shampoos and antimicrobial powders.

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, or other generalized infections by Candida albicans. 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.

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Wikipedia