Undecenoic acid

Absorption

Undecylenic acid may be absorbed through the skin .

Toxicity

Acute oral LD50 in rat and mouse are 2500 mg/kg and 8150 mg/kg, respectively . Acute dermal LD50 in guinea pig and rat are 50 mg/kg and 2000 mg/kg, respectively . There are no data available on the carcinogenicity, mutagenicity, teratogenicity and developmental toxicity of undecylenate .
Oral overdosage may lead to gastrointestinal disturbances, and may affect central nervous system (excitement, somnolence, muscle contraction or spasticity, headache, dizziness), and metabolism (loss of appetite). Prolonged or repeated exposure to undecylenate may cause anorexia or weight loss .

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

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

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.

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

The Uses of Undecenoic acid

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.

The Uses of Undecenoic acid

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

The Uses of Undecenoic acid

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)

The Uses of Undecenoic acid

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.

Background

Undecylenate, or undecylenic acid, is an unsaturated fatty acid with a terminal double bond that is derived from castor oil. Undecylenic acid is also found naturally in the human sweat. It is used as a precursor in the manufacture of aromatic chemicals, polymers or modified silicones . Undecylenic acid was first isolated from the products of distillation of castor oil in 1877 via pyrolysis of ricinoleic acid, and has been polymerized for vinyl production . It it suggested that many organic fatty acids exert fungicidal or fungistatic actions. Undecylenic acid also possesses antifungal properties, but is never used on its own for antifungal purposes. Salts of undecylenate are found in topical over-the-counter or mixture products as antifungal agents. Zinc undecylenate is an example of a topical antifungal agent that treats skin infections such as athlete’s foot and relieves itching, burning, and irritation associated with the skin condition. Due to its bifunctional properties, undecylenate is also used as a linking molecule to conjugate other biomolecules such as proteins. It serves as an acid moiety for anabolic steroid boldenone.

Indications

Indicated for the treatment of fungal infections as a salt form. No therapeutic indications on its own.

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

Pharmacokinetics

Zinc undecylendate acts as a fungistatic agent but fungicidal activity may be observed with chronic exposure in high concentrations . It is effective against Candida albicans . It is proposed that undecylenic acid exerts antimicrobial actions via interacting with nonspecific components in the cell membrane .

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 400??C and low pressure (50 mm) an oxyderivative of oleic acid?aricinoleic acid?athe glyceride of which is the main ingredient of castor oil.

Metabolism

No information regarding metabolism.

Purification Methods

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