Undecenoic acid

Description

Undecylenic acid (C11) or also called 10-undecenoic acid is an organic unsaturated fatty acid derived from castor oil by cracking. Undecylenic acid is an FDA approved active ingredient in medications for skin infections, and relieves itching, burning, and irritation. In technical applications it is used because if its antifungal properties.appearance (25°C) White or very pale yellow crystalline
mass or clear colourless pale
yellow liquid
acid value mg KOH/g 295 - 304
saponification mg KOH/g 295 - 304
iodine value) gI2/100g 132 - 136
congealing point °C 23 - 24
Purity by GC % min. 99%

Chemical Properties

Undecylenic acid is an organic unsaturated fatty acid derived from castor oil. It is the common name of 10-undecenoic acid, (CH₂CH(CH₂)₈COOH). It is used in the manufacture of pharmaceuticals, cosmetics and perfumery, including antidandruff shampoos , antimicrobial powders and as a musk in perfumes and aromas. Undecylenic acid is produced by cracking of castor oil under pressure.

Chemical Properties

10-Undecenoic acid has a characteristic pungent odor.

Chemical Properties

Light-colored liquid; fruity-rosy odor. Almost insoluble in water; miscible with alcohol, chloroform, ether, benzene, and fixed and volatile oils. Combustible.

Occurrence

Reported found as a metabolite in Rhodotorula glutinis var. lusitanica; naturally occurring in the essential oils of Juniperus chinensis, Thujopsis dolabrata and skim milk powder

Uses

10-Undecenoic Acid, is used for the manufacture of pharmaceuticals, cosmetics and perfumery, including antidandruff shampoos, antimicrobial powders and as a musk in perfumes and aromas.

Uses

Undecylenic acid can be used in silicon-based biosensors. Monolayers can be made on bare silicon transducer surfaces with the help of covalent bonds between silicon atom and the double bonds of undecylenic acid. The carboxylic acid groups remain available for the conjugation of biomolecules such as DNA or proteins.

Uses

1. silicon-based biosensors
2. natural fungicide
3. chemical intermediate in fragrance and flavours
4. cosmetics & personal care: highly effective natural antimicrobial and preservative properties
5. undecylenic acids-based diols and polyols
6. additive in cutting fluids (fungicide or as triethanolamine salt as rust inhibiting additive)

Uses

used as antifoaming and surface active agent. As its sulfo – succinate derivative it is used in anti-dandruff shampoos

Definition

ChEBI: An undecenoic acid having its double bond in the 10-position. It is derived from castor oil and is used for the treatment of skin problems.

Preparation

From malonic acid; by pyrolysis of ricinoleic acid or castor oil.

Indications

Undecylenic acid, like zinc undecylenate, is very effective as an external drug for treating moderate dermatophyte infections and yeast dermatitis, but it is not effective for shingles and for candida infections. Synonyms of this drug are benzevrine, micocid, undetin, and others.

General Description

10-Undecenoic acid undergoes copolymerisation with ethylene using the metallocene catalyst system Cp₂ZrCl₂ / methylaluminoxane.

Flammability and Explosibility

Non flammable

Clinical Use

10-Undecenoic acid (Desenex, Cruex) obtained fromthe destructive distillation of castor oil. Undecylenic acidis a viscous yellow liquid. It is almost completely insolublein water but is soluble in alcohol and most organicsolvents.
Undecylenic acid is one of the better fatty acids for useas a fungicide, although cure rates are low. It can be used inconcentrations up to 10% in solutions, ointments, powders,and emulsions for topical administration. The preparationshould never be applied to mucous membranes because it isa severe irritant. Undecylenic acid has been one of theagents traditionally used for athlete’s foot (tinea pedis).Cure rates are low, however.

Synthesis

Undecylenic acid, 10-undecylenic acid (35.4.7), is synthesized by pyrolysis at 400C and low pressure (50 mm) an oxyderivative of oleic acidaricinoleic acidathe glyceride of which is the main ingredient of castor oil.

Purification Methods

Purify the acid by repeated fractional crystallisation from its melt or by distillation in a vacuum. [Beilstein 2 IV 1612.]