Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C11H19O2.Na |
| Molecular Weight | 206.2571 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].[O-]C(=O)CCCCCCCCC=C
InChI
InChIKey=DKYPZNSPQXLRRQ-UHFFFAOYSA-M
InChI=1S/C11H20O2.Na/c1-2-3-4-5-6-7-8-9-10-11(12)13;/h2H,1,3-10H2,(H,12,13);/q;+1/p-1
| Molecular Formula | Na |
| Molecular Weight | 22.9898 |
| Charge | 1 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C11H19O2 |
| Molecular Weight | 183.2674 |
| Charge | -1 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator's Comment: description was created based on several sources, including
http://www.altmedrev.com/publications/7/1/68.pdf |
https://www.ncbi.nlm.nih.gov/pubmed/10991877
Curator's Comment: description was created based on several sources, including
http://www.altmedrev.com/publications/7/1/68.pdf |
https://www.ncbi.nlm.nih.gov/pubmed/10991877
Undecylenic acid is unsaturated fatty acid, which naturally occurs in sweat, and is commercially produced by the vacuum distillation of castor bean oil. It is recognized as GRASE by FDA, and is marketed over the counter to treat skin infections and to relieve itching. Undecylenic acid acts by inhibition of morphogenesis from yeast to hyphae forms.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: map00061 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Curative | CRUEX Approved UseFor the cure of most tinea pedis (athlete's foot) and tinea corporis (ringworm). |
|||
| Curative | CRUEX Approved UseFor the cure of most tinea pedis (athlete's foot) and tinea corporis (ringworm). |
|||
| Primary | Unknown Approved UseUnknown |
|||
| Primary | CRUEX Approved UseItching, burning, redness, irritation, scaling, soreness and discomfort which may accompany these conditions |
Doses
| Dose | Population | Adverse events |
|---|---|---|
2.2 g 3 times / day multiple, oral Dose: 2.2 g, 3 times / day Route: oral Route: multiple Dose: 2.2 g, 3 times / day Co-administed with:: nicotinic acid(50 mgm. morning and night) Sources: |
unhealthy, 56 years n = 1 Health Status: unhealthy Condition: psoriasis Age Group: 56 years Sex: M Population Size: 1 Sources: |
Disc. AE: Toxic labyrinthitis... AEs leading to discontinuation/dose reduction: Toxic labyrinthitis (1 patient) Sources: |
1 g 3 times / day multiple, oral Dose: 1 g, 3 times / day Route: oral Route: multiple Dose: 1 g, 3 times / day Sources: |
unhealthy, 8-14 years n = 4 Health Status: unhealthy Condition: psoriasis | NEURODERMATITIS Age Group: 8-14 years Population Size: 4 Sources: |
|
10 g 3 times / day multiple, oral Highest studied dose Dose: 10 g, 3 times / day Route: oral Route: multiple Dose: 10 g, 3 times / day Sources: |
unhealthy, adult Health Status: unhealthy Condition: psoriasis Age Group: adult Sources: |
|
2 % 1 times / day multiple, topical Dose: 2 %, 1 times / day Route: topical Route: multiple Dose: 2 %, 1 times / day Co-administed with:: zinc undecylenate(0.2) Sources: |
unhealthy n = 29 Health Status: unhealthy Condition: TINEA PEDIS Population Size: 29 Sources: |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Toxic labyrinthitis | 1 patient Disc. AE |
2.2 g 3 times / day multiple, oral Dose: 2.2 g, 3 times / day Route: oral Route: multiple Dose: 2.2 g, 3 times / day Co-administed with:: nicotinic acid(50 mgm. morning and night) Sources: |
unhealthy, 56 years n = 1 Health Status: unhealthy Condition: psoriasis Age Group: 56 years Sex: M Population Size: 1 Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Screening for new compounds with antiherpes activity. | 1984 Oct |
|
| Formation, characterization, and chemistry of undecanoic acid-terminated silicon surfaces: patterning and immobilization of DNA. | 2004 Dec 21 |
|
| Surface functionalization of silicon nanoparticles produced by laser-driven pyrolysis of silane followed by HF-HNO3 etching. | 2004 May 25 |
|
| Synthesis, stereochemistry and biological activity of some novel long alkyl chain substituted thiazolidin-4-ones and thiazan-4-one from 10-undecenoic acid hydrazide. | 2005 Feb |
|
| Kinetic control of the photochemical reactivity of hydrogen-terminated silicon with bifunctional molecules. | 2005 May 24 |
|
| Simple methods for the direct assembly, functionalization, and patterning of acid-terminated monolayers on Si111. | 2005 Nov 8 |
|
| Silicon nanoparticles: applications in cell biology and medicine. | 2006 |
|
| Synthesis and HPLC evaluation of carboxylic acid phases on a hydride surface. | 2006 Apr |
|
| EDC-mediated DNA attachment to nanocrystalline CVD diamond films. | 2006 Aug 15 |
|
| 3,3,5-Trimethylcyclohexanols and derived esters: green synthetic procedures, odour evaluation and in vitro skin cytotoxicity assays. | 2006 Dec |
|
| Self-assembled thermo- and pH responsive micelles of poly(10-undecenoic acid-b-N-isopropylacrylamide) for drug delivery. | 2006 Dec 1 |
|
| Well-defined carboxyl-terminated alkyl monolayers grafted onto H-Si(111): packing density from a combined AFM and quantitative IR study. | 2006 Jan 3 |
|
| Controlling electroosmotic flow in poly(dimethylsiloxane) separation channels by means of prepolymer additives. | 2006 Jul 1 |
|
| Simple fluorimetric liquid chromatographic method for the analysis of undecylenic acid and zinc undecylenate in pharmaceutical preparations. | 2006 Jun 30 |
|
| UV photodissociation spectroscopy of oxidized undecylenic acid films. | 2006 Mar 16 |
|
| Tailor-made olefinic medium-chain-length poly[(R)-3-hydroxyalkanoates] by Pseudomonas putida GPo1: batch versus chemostat production. | 2006 Mar 5 |
|
| Natural treatment of chronic rhinosinusitis. | 2006 Sep |
|
| Grazing angle mirror-backed reflection (GMBR) for infrared analysis of monolayers on silicon. | 2006 Sep 14 |
|
| Nanovectors for anticancer agents based on superparamagnetic iron oxide nanoparticles. | 2007 |
|
| Mechanisms of thermal decomposition of organic monolayers grafted on (111) silicon. | 2007 Jan 30 |
|
| Structure and polymer form of poly-3-hydroxyalkanoates produced by Pseudomonas oleovorans grown with mixture of sodium octanoate/undecylenic acid and sodium octanoate/5-phenylvaleric acid. | 2007 Jan 30 |
|
| Self-assembled monolayers with latent aldehydes for protein immobilization. | 2007 Jan-Feb |
|
| Enzymatic synthesis of arbutin undecylenic acid ester and its inhibitory effect on melanin synthesis. | 2007 Jun 1 |
|
| Enzymatic synthesis of arbutin undecylenic acid ester and its inhibitory effect on mushroom tyrosinase. | 2007 Mar |
|
| Covalent biofunctionalization of silicon nitride surfaces. | 2007 May 22 |
|
| Optimizing biosensing properties on undecylenic Acid-functionalized diamond. | 2007 May 8 |
|
| Cell adhesion properties on photochemically functionalized diamond. | 2007 May 8 |
|
| Effect of double bonds in the formation of sodium dodecanoate and sodium 10-undecenoate mixed micelles in water. | 2007 Oct 11 |
|
| Effects of insemination quantity on honey bee queen physiology. | 2007 Oct 3 |
|
| Determination of nateglinide in human plasma by high-performance liquid chromatography with pre-column derivatization using a coumarin-type fluorescent reagent. | 2007 Sep 5 |
|
| A new concept in the topical treatment of onychomycosis with cyanoacrylate, undecylenic acid, and hydroquinone. | 2008 Apr |
|
| Topographical and functional characterization of the ssDNA probe layer generated through EDC-mediated covalent attachment to nanocrystalline diamond using fluorescence microscopy. | 2008 Aug 19 |
|
| A rapid and sensitive screening system for human type I collagen with the aim of discovering potent anti-aging or anti-fibrotic compounds. | 2008 Dec 31 |
|
| Comparison of the skin sensitizing potential of unsaturated compounds as assessed by the murine local lymph node assay (LLNA) and the guinea pig maximization test (GPMT). | 2008 Jun |
|
| Genomic analysis of post-mating changes in the honey bee queen (Apis mellifera). | 2008 May 19 |
|
| Oxidation-triggered release of fluorescent molecules or drugs from mesoporous Si microparticles. | 2008 Nov 25 |
|
| Spectra and kinetic studies of the compound I derivative of cytochrome P450 119. | 2008 Oct 8 |
|
| Undecylenic acid: a valuable and physiologically active renewable building block from castor oil. | 2009 |
|
| Polymerizable vesicles based on a single-tailed fatty acid surfactant: a simple route to robust nanocontainers. | 2009 Feb 3 |
|
| The compatibility of hepatocytes with chemically modified porous silicon with reference to in vitro biosensors. | 2009 Jan |
|
| Porous silicon for photosensitized formation of singlet oxygen in water and in simulated body fluid: two methods of modification by undecylenic acid. | 2009 Jun |
|
| Fed-batch production of unsaturated medium-chain-length polyhydroxyalkanoates with controlled composition by Pseudomonas putida KT2440. | 2009 Mar |
|
| Electrochemical behavior of gold colloidal alkyl modified silicon surfaces. | 2009 Nov |
|
| Stimulatory effect of undecylenic acid on mouse osteoblast differentiation. | 2010 Apr |
|
| Capric acid secreted by S. boulardii inhibits C. albicans filamentous growth, adhesion and biofilm formation. | 2010 Aug 10 |
|
| Simple surface modification of poly(dimethylsiloxane) for DNA hybridization. | 2010 Dec 6 |
|
| Bioconjugate functionalization of thermally carbonized porous silicon using a radical coupling reaction. | 2010 Dec 7 |
|
| Rapid approach to biobased telechelics through two one-pot thiol-ene click reactions. | 2010 Jun 14 |
|
| Simultaneous biosynthesis of two copolymers in Pseudomonas putida GPo1 using a two-stage continuous culture system. | 2010 Jun 14 |
|
| Production of functionalized polyhydroxyalkanoates by genetically modified Methylobacterium extorquens strains. | 2010 Sep 16 |
Patents
Sample Use Guides
Undecylenic acid antifungal liquid should be applied to affected area topically.
Route of Administration:
Topical
To investigate effect of undecylenic acid on Candida albicans morphogenesis, cells were grown overnight at 30°C on YPD agar and harvested by scraping the cells from the plate and suspending in YPD broth. Two milliliters of cells at 106 cells/ml was distributed into tubes containing liner, approximately 0.5 g of liner per tube. The cultures were incubated at 39°C with agitation for 2 h; planktonic cells were analyzed microscopically to determine the percentage of cells with germ tubes. The presence of Undecylenic acid inhibited the appearance of germ tubes, with 10 μM UDA causing a sevenfold reduction.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:03:21 GMT 2023
by
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on
Fri Dec 15 15:03:21 GMT 2023
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| Record UNII |
V50TG7E11W
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| Record Status |
Validated (UNII)
|
| Record Version |
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PARENT -> SALT/SOLVATE |
