Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C11H22O2 |
| Molecular Weight | 186.2912 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCCCCCCCC(O)=O
InChI
InChIKey=ZDPHROOEEOARMN-UHFFFAOYSA-N
InChI=1S/C11H22O2/c1-2-3-4-5-6-7-8-9-10-11(12)13/h2-10H2,1H3,(H,12,13)
| Molecular Formula | C11H22O2 |
| Molecular Weight | 186.2912 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Undecanoic acid (UDA) is a fatty acid with significant antimycotic activity. Undecanoic acid is a straight-chain, eleven-carbon saturated medium-chain fatty acid found in body fluids; the most fungitoxic of the C7:0 - C18:0 fatty acid series. It has a role as a human metabolite and an antifungal agent. It is a straight-chain saturated fatty acid and a medium-chain fatty acid. It is a conjugate acid of an undecanoate. It derives from a hydride of an undecane. Undecanoic acid inhibited the production of exocellular lipase and keratinase but stimulated the production of exocellular phospholipase A in T. rubrum undecanoic acid-resistant mutant (udar). At its minimum inhibitory concentration, undecanoic acid inhibits biosynthesis of phosphatidyl serine, phosphatidyl ethanolamine and polyphosphoinositol but does not inhibit the synthesis of phosphatidyl glycerol, phosphatidyl choline, phosphatidyl inositol and phosphatidic acid in Trichophyton rubrum. At higher concentration, however UDA inhibits biosynthesis of all phosphatides present in this dermatophyte. UDA also affects catabolism of these phosphatides. This inhibitory effect of UDA may be partially responsible for its toxic action on T. rubrum.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Localized surface plasmon-enhanced fluorescence spectroscopy for highly-sensitive real-time detection of DNA hybridization. | 2010-08-15 |
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| Testosterone undecanoate in the treatment of male hypogonadism. | 2010-08 |
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| A novel PDMS micro membrane biosensor based on the analysis of surface stress. | 2010-07-15 |
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| Randomized cross-over clinical trial of injectable vs. implantable depot testosterone for maintenance of testosterone replacement therapy in androgen deficient men. | 2010-07 |
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| Effects of chronic testosterone administration on myocardial ischemia, lipid metabolism and insulin resistance in elderly male diabetic patients with coronary artery disease. | 2010-06-25 |
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| Effects of testosterone and estrogen replacement on memory function. | 2010-06-18 |
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| Enhanced production of longer side-chain polyhydroxyalkanoic acid with omega-aromatic group substitution in phaZ-disrupted Pseudomonas fluorescens BM07 mutant through unrelated carbon source cometabolism and salicylic acid beta-oxidation inhibition. | 2010-06 |
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| Liquid-phase microextraction with solidification of the organic floating drop for the preconcentration and determination of mercury traces by electrothermal atomic absorption spectrometry. | 2010-04 |
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| Aqueous normal phase retention of nucleotides on silica hydride-based columns: method development strategies for analytes relevant in clinical analysis. | 2010-03 |
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| The effects of sacral acupuncture on acetic acid-induced bladder irritation in conscious rats. | 2010-03 |
|
| Transformation of some 3alpha-substituted steroids by Aspergillus tamarii KITA reveals stereochemical restriction of steroid binding orientation in the minor hydroxylation pathway. | 2010-02-15 |
|
| Transcriptional profiling reveals the expression of novel genes in response to various stimuli in the human dermatophyte Trichophyton rubrum. | 2010-02-08 |
|
| Treatment of municipal solid waste leachate using a submerged anaerobic membrane bioreactor at mesophilic and psychrophilic temperatures: analysis of recalcitrants in the permeate using GC-MS. | 2010-02 |
|
| Timetable of effects of testosterone administration to hypogonadal men on variables of sex and mood. | 2009-12 |
|
| Androgens and sexual function: a placebo-controlled, randomized, double-blind study of testosterone vs. dehydroepiandrosterone in men with sexual dysfunction and androgen deficiency. | 2009-12 |
|
| Emission of volatile organic compounds after herbivory from Trifolium pratense (L.) under laboratory and field conditions. | 2009-11 |
|
| Production and characterization of homopolymer poly(3-hydroxyvalerate) (PHV) accumulated by wild type and recombinant Aeromonas hydrophila strain 4AK4. | 2009-09 |
|
| Quantification of testosterone undecanoate in human hair by liquid chromatography-tandem mass spectrometry. | 2009-08 |
|
| The effects of arbuscular mycorrhizal fungi on direct and indirect defense metabolites of Plantago lanceolata L. | 2009-07 |
|
| Thermodynamics of surfactants, block copolymers and their mixtures in water: the role of the isothermal calorimetry. | 2009-06-29 |
|
| Medium-chain fatty acids and glutathione derivatives as inhibitors of S-nitrosoglutathione reduction mediated by alcohol dehydrogenase 3. | 2009-06-15 |
|
| Floral and insect-induced volatile formation in Arabidopsis lyrata ssp. petraea, a perennial, outcrossing relative of A. thaliana. | 2009-06 |
|
| 10-undecanhydroxamic acid, a hydroxamate derivative of the undecanoic acid, has strong antimicrobial activity through a mechanism that limits iron availability. | 2009-05 |
|
| Body fat content and testosterone pharmacokinetics determine gonadotropin suppression after intramuscular injections of testosterone preparations in normal men. | 2009-04-04 |
|
| Production, characterization and determination of the real catalytic properties of the putative 'succinate dehydrogenase' from Wolinella succinogenes. | 2009-03 |
|
| Aqueous normal-phase retention of nucleotides on silica hydride columns. | 2009-02-13 |
|
| Peak energy turnover in lactating European hares: the role of fat reserves. | 2009-01 |
|
| The compatibility of hepatocytes with chemically modified porous silicon with reference to in vitro biosensors. | 2009-01 |
|
| Decline of plasma 5alpha-dihydrotestosterone (DHT) levels upon testosterone administration to elderly men with subnormal plasma testosterone and high DHT levels. | 2008-10 |
|
| Effects of testosterone undecanoate administered alone or in combination with letrozole or dutasteride in female to male transsexuals. | 2008-10 |
|
| A single amino acid substitution in one of the lipases of Aspergillus nidulans confers resistance to the antimycotic drug undecanoic acid. | 2008-10 |
|
| Piezoelectric biosensors assisted with electroacoustic impedance spectroscopy: a tool for accurate quantitative molecular recognition analysis. | 2008-08-06 |
|
| Hair analysis of anabolic steroids in connection with doping control-results from horse samples. | 2008-07 |
|
| Surface plasmon resonance-enhanced fluorescence implementation of a single-step competition assay: demonstration of fatty acid measurement using an anti-fatty acid monoclonal antibody and a Cy5-labeled fatty acid. | 2008-06-15 |
|
| Covalent assembly and micropatterning of functionalized multiwalled carbon nanotubes to monolayer-modified Si(111) surfaces. | 2008-06-01 |
|
| Dimethandrolone (7alpha,11beta-dimethyl-19-nortestosterone) and 11beta-methyl-19-nortestosterone are not converted to aromatic A-ring products in the presence of recombinant human aromatase. | 2008-06 |
|
| Increased terpenoid accumulation in cotton (Gossypium hirsutum) foliage is a general wound response. | 2008-04 |
|
| Effects of oral testosterone treatment on myocardial perfusion and vascular function in men with low plasma testosterone and coronary heart disease. | 2008-03-01 |
|
| Parenteral oestrogen in the treatment of prostate cancer: a systematic review. | 2008-02-26 |
|
| Effect of the organic loading rate on the performance of anaerobic acidogenic fermentation of two-phase olive mill solid residue. | 2008 |
|
| Swinging effect of salicylic acid on the accumulation of polyhydroxyalkanoic acid (PHA) in Pseudomonas aeruginosa BM114 synthesizing both MCLandSCL-PHA. | 2007-12 |
|
| Changes in aortic endothelium ultrastructure in male rats following castration, replacement with testosterone and administration of 5alpha-reductase inhibitor. | 2007-11 |
|
| A dose-response study of testosterone on sexual dysfunction and features of the metabolic syndrome using testosterone gel and parenteral testosterone undecanoate. | 2007-10-06 |
|
| Analysis of Trichophyton rubrum gene expression in response to cytotoxic drugs. | 2007-06 |
|
| Probing protein adsorption onto mercaptoundecanoic acid stabilized gold nanoparticles and surfaces by quartz crystal microbalance and zeta-potential measurements. | 2007-05-22 |
|
| More than eight years' hands-on experience with the novel long-acting parenteral testosterone undecanoate. | 2007-05 |
|
| Testosterone depot injection in male hypogonadism: a critical appraisal. | 2007 |
|
| Methanogenic and sulphate reducing bacterial population levels in a full-scale anaerobic reactor treating pulp and paper industry wastewater using fluorescence in situ hybridisation. | 2007 |
|
| Silicon nanoparticles: applications in cell biology and medicine. | 2006 |
|
| Medium chain length fatty acids stimulate triacylglycerol synthesis in tissue culture cells. | 1992-01-22 |
Sample Use Guides
The combinations of tricyclodecan-9-yl-xanthogenate (D 609) with undecanoic acid (C11) and D 609 with myristic acid (C14) were tested in 3 rodent tumor models in vivo. In L 1210 mouse lymphoid leukemia growing in CD2F1 mice the combination of D 609/C11 given intraperitoneally in a concentration of 100 mg/kg for more than 1 day effected a significant difference in the survival curves between the control and therapeutic groups in 1 out of 2 experiments.
Route of Administration:
Intraperitoneal
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 19:04:52 GMT 2025
by
admin
on
Mon Mar 31 19:04:52 GMT 2025
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| Record UNII |
138ON3IIQG
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| Record Status |
Validated (UNII)
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| Record Version |
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| Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C514
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JECFA EVALUATION |
UNDECANOIC ACID
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7885
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32368
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100000139984
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UNDECYLIC ACID
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112-37-8
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32369
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DTXSID8021690
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C016173
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138ON3IIQG
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CHEMBL108030
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8180
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C152801
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203-964-2
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11
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SUB89027
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