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.
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.
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
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.
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.
Preparation
From malonic acid; by pyrolysis of ricinoleic acid or castor oil.
General Description
10-Undecenoic acid undergoes copolymerisation with ethylene using the metallocene catalyst system Cp2ZrCl2 / methylaluminoxane.
Flammability and Explosibility
Nonflammable
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.
Purification Methods
Purify the acid by repeated fractional crystallisation from its melt or by distillation in a vacuum. [Beilstein 2 IV 1612.]
