Ingredientes10-Undecenoic acid — also widely known as undecylenic acid — is an organic, monounsaturated fatty acid. 10-Undecenoic acid is defined as a chemical compound with the molecular formula C₁₁H₂₀O₂ and a molecular weight of 184.27, also known by synonyms such as undecylenic acid and 10-Hendecenoic acid. Its linear structural formula is CH₂=CH(CH₂)₈COOH, and its empirical formula is C₁₁H₂₀O₂. It is characterized by the absence of stereocenters, making stereoisomerism impossible.
Chemically, undecenoic acid is an unsaturated fatty acid with the molecular formula C₁₁H₂₀O₂. It features a double bond between the 10th and 11th carbon atoms, which is a critical aspect of its biological activity. Undecylenic acid (10-undecenoic acid) is a monounsaturated fatty acid (aliphatic monocarboxylic acid) with a slightly sweaty smell, which is of particular importance in medicine as an antimycotic due to its fungicidal effect. The fatty acid with the molecular formula C₁₁H₂O₂ and the linear formula H₂C=CH(CH₂)₈-COOH, is insoluble in water, soluble in ethyl alcohol, chloroform, ether and benzene. 10-Undecenoic acid has a characteristic pungent odor and appears as a light-colored liquid with a fruity-rosy quality.
Undecylenic acid is an 11-carbon monounsaturated fatty acid (MUFA) derived from the distillation of castor oil via pyrolysis, and is also naturally found in human sweat. It is a component of the excretion of human sweat glands. It has been reported as a metabolite in Rhodotorula glutinis var. lusitanica and is naturally occurring in the essential oils of Juniperus chinensis, Thujopsis dolabrata, and skim milk powder. It is also a physiological chemical contained in human sweat, tears, and hair.
Undecylenic acid is prepared by pyrolysis of ricinoleic acid, which is derived from castor oil. Specifically, the methyl ester of ricinoleic acid is cracked to yield both undecylenic acid and heptanal. This synthesis is carried out by pyrolysis at 400°C and low pressure (50 mmHg) of ricinoleic acid — an oxyderivative of oleic acid — the glyceride of which is the main ingredient of castor oil. 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 an unsaturated fatty acid antifungal agent available as an ointment, powder, or liquid, whose therapeutic efficacy was first recognized in the 1940s in treating superficial fungal diseases affecting military troops. Shapiro and Rothman reported their research on undecylenic acid in the treatment of dermatomycosis in 1945, when the United States was engaged in World War II, as cutaneous diseases including fungous infections were a major cause of disability.
During World War II, fungal infections plagued soldiers stationed in humid, challenging environments. The search for a potent, reliable antifungal led scientists to castor oil, a humble plant extract with untapped potential; through chemical work, researchers isolated undecylenic acid, unlocking a new era in topical antifungal care. In controlled field studies, active fungal infections developed in only 1.07% of 281 men who used undecylenic acid-undecylenate powder on one foot, compared with 8.85% in untreated men. These observations suggested that the use of undecylenic acid powder afforded a meaningful degree of protection against fungus infections.
The strongest undecylenic acid powder tested in military studies contained 10% zinc undecylenate in talc. The post-war (1956) standard US military foot powder, fungicidal, contained either undecylenic acid 2% and zinc undecylenate 20%, or a combination of calcium propionate, zinc caprylate, and zinc propionate.
Undecylenic acid was used effectively in World War II as a topical antifungal for foot fungus in soldiers wearing boots under demanding conditions. Due to its effectiveness against fungus, it was subsequently chosen as one of the first-line treatments against the occurrence of fungal candida overgrowth and related diseases that appeared after the introduction of antibiotics in the 1940s. Undecylenic acid was first discovered in 1877. What began as a wartime remedy soon made its way into everyday medicine cabinets, marking a turning point for natural antifungal treatments. Soldiers relied on it to combat athlete's foot and ringworm, conditions that could sideline entire units.
Undecylenic acid and undecylenate salts (e.g., calcium undecylenate, copper undecylenate, zinc undecylenate) are topical antifungal agents. The drugs are usually used in combination, with the combined potency labeled in terms of total undecylenate, although they can also be used individually. The combination containing zinc undecylenate and undecylenic acid is sometimes referred to as zincundecate.
Undecylenic acid and derivatives are available over the counter (OTC) in the form of powder, solution, spray, cream, ointment, and soap. They are currently used as systemic antifungal agents, dosed orally either as the free fatty acid, typically in an oil-based soft gel capsule, or as a salt.
Undecylenic acid can effectively control skin fungal infection, though the precise mechanism of its fungal inhibition has required investigation. Hyphal growth of Candida albicans and biofilm formation have been well recognized as important virulence factors for the initiation of skin infection and the later development of disseminated infection.
Inhibition of morphogenesis: In terms of the mechanism underlying its antifungal effects against Candida albicans, undecylenic acid inhibits morphogenesis. In a study on denture liners, undecylenic acid in the liners was found to inhibit conversion of yeast to the hyphal form (which are associated with active infection), via inhibition of fatty acid biosynthesis.
Chain-length optimum: The mechanism of action and effectiveness in fatty acid-type antifungals is dependent on the number of carbon atoms in the chain, with efficacy increasing with chain length. The optimum appears to be 11 carbon atoms, as with longer fatty acids the effect is limited by lower solubility in water, which results in reduced bioavailability.
Biofilm suppression and virulence factor downregulation: In laboratory investigation of undecylenic acid's antifungal mechanisms via virulence factors of C. albicans during biofilm formation, undecylenic acid inhibited biofilm formation effectively at concentrations above 3 mM. In the presence of this compound, the morphological transition from yeast to filamentous phase was abolished at concentrations above 4 mM. The cell surface was crumpled and cells displayed an atrophic appearance under scanning electron microscopy even at low concentrations. Drug treatment also decreased the transcriptions of hydrolytic enzymes such as secreted aspartic protease, lipase, and phospholipase. Hyphal formation-related genes, like HWP1, were significantly reduced at the transcriptional level in drug-treated biofilm conditions. The down-regulated profile of these genes led to a poorly organized biofilm in the undecylenic acid-treated environment.
Membrane disruption: The presence of the double bond imparts unique chemical properties that influence undecenoic acid's interaction with microbial cell membranes. The primary mechanism of action of undecenoic acid is its ability to disrupt the integrity of microbial cell membranes.
Germ-tube inhibition: 10 μM undecylenic acid (UDA) caused a sevenfold reduction in germ tube appearance. This concentration of UDA had no effect on the growth rate, indicating that morphogenesis, not growth, was being inhibited.
Undecylenic acid inhibits the formation of fungal biofilm — an extracellular matrix that protects and helps fungal cells survive — and branching filaments (hyphae) that grow and spread, forming a fungal network. The formation of biofilm and hyphae are associated with active fungal infections and virulence. Undecylenic acid may also curb fungal growth by inhibiting the fungal enzyme involved in fat metabolism.
While the role of fatty acids in cell structure and metabolism is well established, the potential of fatty acids as antimicrobial agents, particularly in topical applications, is less well understood. A wide range of fatty acids has been found to exert broad-spectrum activity against a range of common gram-positive and gram-negative pathogenic bacteria. There are several advantages to utilizing fatty acids in the treatment of microbial pathogens: they do not appear to quickly develop resistance, and several are naturally occurring skin components in the human innate immune response to pathogens, and as such, they have extremely low toxicity risks.
A novel formulation of undecylenic acid compounded with L-Arginine, called GS-1, induced concentration-dependent tumor cell death, with undecylenic acid being the cytotoxic component. GS-1-mediated cell death was caspase-dependent with a reduction in mitochondrial membrane potential, suggesting a pro-apoptotic mechanism of action. GS-1 was found to localize intracellularly to lipid droplets. In contrast to previous studies where lipid droplets have been shown to be protective against fatty acid-induced cell death, lipid droplets could not protect against GS-1-induced cytotoxicity. A role for Fatty Acid Transport Protein 2 (FATP2) in the uptake of this compound was identified.
Regulatory status: Undecylenic acid and its salts of calcium, copper, and zinc — for a total undecylenate concentration of 10–25% — have received FDA approval as antifungals in its Final Monograph. All drugs listed are approved for the treatment of athlete's foot and the relief of its symptoms. The drugs contained within the FDA's Final Monograph are considered Generally Recognized As Safe and Effective (GRASE) for the treatment of athlete's foot.
Double-blind clinical trial (Chretien et al., 1980): One hundred fifty-one patients with tinea pedis participated in a double-blind study to assess the efficacy and safety of a powder containing undecylenic acid 2% and zinc undecylenate 20% versus a placebo powder. Patients were assigned to apply twice-daily applications of either active powder or placebo for a period of 4 weeks. Trichophyton rubrum or Trichophyton mentagrophytes were isolated from pre-treatment cultures of 85 patients. Of these, 88% treated with active powder had negative cultures after 4 weeks compared with 17% of those treated with placebo powder (p < 0.001). Of those treated with active powder, 80% were KOH-negative after 4 weeks compared with 49% of those treated with placebo powder (p = 0.001). Erythema and scaling were significantly improved by therapy with active powder, as were subjective evaluations of itching and burning.
Controlled clinical trial (topical powder): One hundred and four patients with mycologically confirmed tinea pedis took part in a controlled clinical trial to determine the efficacy of undecylenic acid powder preparations in the treatment of their fungal infections. Clinical and mycological cures were obtained in 53% of those subjects treated with undecylenic acid powders, compared with 7% of those treated with the talc vehicle or left untreated. Undecylenic acid in a powder vehicle appears to be a safe and effective agent in the treatment of tinea pedis.
Comparative efficacy: Undecylenic acid's therapeutic efficacy was first recognized in the 1940s in treating superficial fungal diseases affecting military troops; however, it has little efficacy compared with newer agents. The advantages of these compounds are that they are safe, inexpensive, and rarely cause local irritation. Undecylenic acid is generally used for mild to moderate cases, and persistent or severe infections may require additional or systemic treatments.
Limitations noted in sources: Undecylenic acid and derivatives are not effective for scalp or nails. Per OTC label guidance, for athlete's foot and ringworm, the product should be used daily for 4 weeks; if the condition persists longer, a doctor should be consulted, and this product is not effective on the scalp or nails.
A study at the Medical University of South Carolina tested 10 resilient denture liners; 2 were found to inhibit the switch from the yeast form to hyphae, and a third stimulated this switch. The inhibitor was determined to be undecylenic acid. Denture liners are easily colonized by Candida spp. In an attempt to prevent biofilm colonization, manufacturers have incorporated undecylenic acid (UDA) into denture liners. In this in vitro study, the effects of UDA released from denture liners on Candida biofilms were investigated. The concentrations of UDA released from commercial liners were determined by GC-MS. Minimum inhibitory concentration (MIC) and minimum fungistatic concentration (MFC) tests were performed for C. albicans and C. glabrata. Biofilms were evaluated by cell counts, metabolic activity, structure, and secretion of proteinase or phospholipase. The concentrations of UDA released were within the MIC and MFC ranges.
Evidence strength: Evidence for undecylenic acid against Candida albicans is primarily in vitro and in dental materials science. Currently, undecylenic acid is primarily known for its antifungal properties and is the active ingredient for many topical antifungal treatments. The antifungal effects of undecylenic acid have been extensively investigated in Candida albicans, where studies have shown that undecylenic acid can inhibit biofilm formation. No published large-scale randomized controlled trials in humans on systemic candida overgrowth treatment were identified in the search.
In an animal model of skin infection, topical GS-1 (a novel ammonium carboxylate salt of undecylenic acid) successfully eradicated MRSA from infected, abraded skin after 6 days of treatment with no signs of toxicity. Repeated topical GS-1 exposure in humans caused no irritation or sensitization. These results support GS-1 as a potential novel topical antibacterial for the treatment of impetigo and other skin infections. Evidence is from a single preclinical and early human safety study. No large-scale human clinical trial results were identified in available sources.
A novel formulation of undecylenic acid compounded with L-Arginine (GS-1) induced concentration-dependent tumor cell death, with undecylenic acid being the cytotoxic component. In contrast to previous studies where lipid droplets have been shown to be protective against fatty acid-induced cell death, lipid droplets could not protect against GS-1-induced cytotoxicity. A role for Fatty Acid Transport Protein 2 (FATP2) was found in the uptake of this compound. Collectively, this study demonstrates that GS-1 has effective pro-apoptotic antitumor activity in vitro. These data demonstrate that GS-1 has effective antitumor activity in vitro and lay the foundation for exploring other novel applications for undecylenic acid. Evidence strength: This is exclusively in vitro (cell culture) evidence. No human or animal trials of undecylenic acid as a cancer treatment have been reported in the sources identified.
10-undecylenic acid is an OTC antifungal therapy and a nutritional supplement. It is an unsaturated medium-chain fatty acid (MCFA) derivative, and its 11-mer sodium salt, uC11, was hypothesized to improve intestinal permeation similarly to the established enhancer sodium caprate (C10), but without the toxicity of the parent saturated MCFA. Rat jejunal and colonic in situ intestinal instillations of 100 mM sodium undecylenate with FITC-dextran 4000 solutions yielded comparable regional enhancement ratios to sodium caprate. Mini-tablets of uC11 delivered more of the marker compound than C10 mini-tablets in both regions, as reflected by a statistically higher AUC, and with no evidence of membrane perturbation. The unsaturated bond in uC11 therefore confers a reduction in lipophilicity and cytotoxicity compared to the saturated C11 analog, and the resulting permeation enhancement is on a par with or superior to that of C10. Evidence strength: These are preclinical animal and cell-culture data. No human clinical trials of sodium undecylenate as a standalone intestinal permeation enhancer were found in available sources.
Undecylenic acid and its salts of calcium, copper, and zinc are approved at a total undecylenate concentration of 10–25%. Undecylenic acid and undecylenate salts are used individually or in combination in total concentrations of 10–25%. Preparations containing the drugs are applied topically twice daily after cleansing the affected area. The ointment should be used at night. Treatment should usually be continued for 4 weeks when treating athlete's foot or ringworm and for 2 weeks when treating jock itch.
Per OTC labeling, products should not be used on children under 2 years of age unless directed by a doctor.
The advantages of undecylenic acid and tolnaftate-class compounds are that they are safe, inexpensive, and rarely cause local irritation. Topical use of undecylenic acid and derivatives is unlikely to result in overdose. Fatty acids such as undecylenic acid are naturally occurring skin components in the human innate immune response to pathogens, and as such, they have extremely low toxicity risks associated with their use.
Common side effects of undecylenic acid and derivatives include skin irritation, burning, and sensitivity. One of the most commonly reported side effects of undecenoic acid is skin irritation. Users may experience redness, itching, or a burning sensation at the site of application. These symptoms are usually mild and tend to resolve on their own. Undecylenic acid may cause allergic reactions, which can be serious. Users should stop using undecylenic acid and get help right away if symptoms of a serious allergic reaction appear.
In its liquid form, undecylenic acid may cause irritation in the mucous membranes in some people. However, since it is naturally found in small amounts within the body, most people can tolerate it. For those who are sensitive to the potent fatty acid, it can also be administered in salt form (zinc undecylenate).
In a human exposure study of the novel ammonium carboxylate salt formulation GS-1, repeated topical GS-1 exposure in humans caused no irritation or sensitization.
Although topical formulations can eliminate and help stop the spread of fungal infections on cuticles, around nail edges, and under nail tips where reachable with an applicator brush, topical antifungal treatment will not penetrate hard nail surfaces.
There is minimal information on systemic drug interactions with undecenoic acid due to its primary topical application.
Condiciones de salud que 10-Ácido undecenoico puede ayudar a apoyar.
10-Undecenoic Acid (undecylenic acid) is an FDA-recognized over-the-counter antifungal agent approved for treating tinea pedis (athlete's foot). It disrupts fungal cell membranes, inhibiting dermatophyte growth. A double-blind trial (n=151) showed 88% of treated patients achieved negative cultures after 4 weeks versus 17% on placebo. It is available in creams, powders, and solutions at 10–25% concentrations.
Undecylenic acid is an unsaturated C11 fatty acid derived from castor oil with recognized antifungal activity against Candida. It prevents the yeast-to-hyphal morphological transition critical to Candida pathogenesis and disrupts biofilms. It has FDA recognition as an OTC antifungal active ingredient and is a standard component of natural Candida support formulas.
10-Undecenoic acid is another name for undecylenic acid, an FDA-recognized antifungal fatty acid derived from castor oil. It inhibits Candida by disrupting fatty acid biosynthesis and preventing the yeast-to-hyphal morphological switch. It is a standard ingredient in natural Candida cleanse formulations, with in vitro evidence supporting anti-Candida potency.
10-Undecenoic acid (undecylenic acid) is an unsaturated fatty acid derived from castor oil with FDA-approved OTC status for superficial fungal skin infections including tinea pedis, tinea corporis, and tinea cruris. It disrupts fungal cell membranes, inhibiting growth of dermatophytes such as Trichophyton species. In vitro studies confirm activity against multiple dermatophyte species. Its therapeutic efficacy was first recognized in the 1940s for military troops.
10-Undecenoic Acid (undecylenic acid) is a naturally occurring antifungal fatty acid from castor oil with documented in vitro activity against Candida albicans biofilm formation, directly relevant to vulvovaginal candidiasis (VVC). It inhibits fungal cell growth and biofilm formation in laboratory studies. It is used in antifungal topical preparations relevant to vaginal yeast infections.
10-Undecenoic acid (undecylenic acid) is a naturally occurring unsaturated fatty acid with established antifungal properties, included in parasite cleanse and Candida protocols for its ability to disrupt fungal and microbial cell membranes. It is listed in antiparasitic supplement databases.
Sistemas corporales que 10-Ácido undecenoico puede ayudar a apoyar.
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