10-Undecylenic acid

Undecylenic acid (an antifungal fatty acid) is a weak sensitizer. One case of contact allergy from undecylenic acid in Desenex ointment has been reported (Gelfarb and Leider 1960). 

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Undecylenic acid (or 10-undecenoic acid) (I), a comparatively inexpensive commercial product obtained from castor oil, reacts with bromine in dry carbon tetrachloride to give 10 11-dibromoundecoic acid (II), which upon heating with a concentrated solution of potassium hydroxide yields 10-niidecynoic acid (III) ... 

The main advantage of this ointment is its low price. This combination has now been replaced by more active modern antimycotics. Long ago, the antimycotic effect of aUphatic carboxyUc acids with an increasing number of C-atoms was discovered. The optimum is 11 C-atoms and CH2=CH(CH2)gCOOH, undecylenic acid [112-38-9] C22H2QO2, is used in several ointments. 

H-C-H 1 1 H-C-H 1 I H-C-H I Pyrolysis High heat Undecylenic acid, heptaldehyde... 

Pyrolytic Decomposition. The pyrolytic decomposition at 350—460°C of castor oil or the methyl ester of ricinoleic acid spHts the ricinoleate molecule at the hydroxyl group forming heptaldehyde and undecylenic acids. Heptaldehyde, used in the manufacture of synthetic flavors and fragrances (see Elavors and spices Perfumes) may also be converted to heptanoic acid by various oxidation techniques and to heptyl alcohol by catalytic hydrogenation. When heptaldehyde reacts with benzaldehyde, amyl cinnamic aldehyde is produced (see Cinnamic acid, cinnamaldehyde, and cinnamyl... 

The use of a catalyst such as cadmium oxide increases the yield of dibasic acids to about 51% of theoretical. The composition of the mixed acids is about 75% C-11 and 25% C-12 dibasic acids (73). Reaction of undecylenic acid with carbon monoxide using a triphenylphosphine—rhodium complex as catalyst gives 11-formylundecanoic acid, which, upon reaction with oxygen in the presence of Co(II) salts, gives 1,12-dodecanedioic acid in 70% yield (74). 

Cracking of the ester at about 500°C leads to the formation of the undecylenic acid ester together with such products as heptyl alcohol, heptanoic acid and heptaldehyde. Undecylenic acid may then be obtained by hydrolysis of the ester. Treatment of the acid by HBr in the presence of a peroxide leads to w-bromoundecanoic acid together with the 10-isomer, which is removed. Treatment of the w-bromo derivative with ammonia leads to w-aminoundecanoic acid, which has a melting point of 50°C (Figure 18.8). 

The sulfosuccinate monoester based on undecylenic acid monoethanolamide and its antimicrobial properties was described shortly before [12]. In comparison of shampoos containing different antidandruff agents, this sulfosuccinate s performance was favorably evaluated [13]. It was neutral with respect to lipid replacement on scalp and forehead after application of the respective shampoo. This undecylenic acid-based sulfosuccinate was also found to reduce dandruff formation in another investigation [14]. 

Undecylenic acid monoethanolamide, if fungicidal properties are desired... 

C7H14O 111-71-7) see Undecylenic acid [3a/ -(3aa,4a,SP,6aa)]-4-[2-(2-heptyl-l,3-dioxolan-2-yl)ethyl]hexahydro-5-hydroxy-2//-cyclopenta[6]furan-2-one... 

PHAs from Undecylenic acid Ontene Nonene Decene... 

The most widespread are dermatophytic fungal infections, which include skin, hair, and nails. Most infections can be cured by using topical drugs, such as tolnaftate, undecylenic acid, haloprogin, clotrimazole, and miconazole. Griseofulvin is used orally for deep infections, in particular for infections of the nail bed. Currently, ketoconazole is widely used for treating chronic dermatophytes. 

Vndecylenic acid 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— ricinoleic acid—the glyceride of which is the main ingredient of castor oil [59,60]. 

Undecylenic acid, like zinc undecylenate, is very effective as an external drag 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. 

Contraindications Flypersensifivify to undecylenic acid or any component of its formulation... 

Undecenoic acid (undecylenic acid, commercial grade) may be obtained from the Eastman Kodak Company. The pure grade acid is also used with good results. However, for general purposes, no difficulty is encountered in preparing 10-undecynoic acid from the commercial grade acid if the final fractionation by vacuum distillation is carried out carefully. 

CH2 = CH(CH2)8CH20H, C11H22O, Mr 170.29, bp2.ikv 133°C, d 0.8495, 1.4500, was tentatively identified, e.g., in the wax gourd (Benincasa hispida, Cogn.) [13], and is a colorless liquid with a fatty-green, slightly citrus-like odor. It can be synthesized from 10-undecylenic acid and is used to give flower perfumes a fresh note. 

Undecylenic acid, 12-25% (powder, solution) apply to affected areas twice daily Blis-To-Sol, Elon Dual Defense Anti-Fungal ... 

This is an antifungal solution for topical use containing 25% undecylenic acid and 3% chloroxylenol as its active... 

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