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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
Structure of SODIUM UNDECYLENATE

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

HIDE SMILES / InChI

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

Description
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

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
CRUEX

Approved Use

For the cure of most tinea pedis (athlete's foot) and tinea corporis (ringworm).
Curative
CRUEX

Approved Use

For the cure of most tinea pedis (athlete's foot) and tinea corporis (ringworm).
Primary
Unknown

Approved Use

Unknown
Primary
CRUEX

Approved Use

Itching, burning, redness, irritation, scaling, soreness and discomfort which may accompany these conditions
Doses

Doses

DosePopulationAdverse 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

AEs

AESignificanceDosePopulation
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:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Screening for new compounds with antiherpes activity.
1984 Oct
One-pot sequences of reactions with sol-gel entrapped opposing reagents: an enzyme and metal-complex catalysts.
2002 Dec 4
Determination of undecylenic and sorbic acids in cosmetic preparations by high performance liquid chromatography with electrochemical detection.
2002 Nov 7
Enzymatic synthesis of hydrophilic undecylenic acid sugar esters and their biodegradability.
2003 Jan
Formation, characterization, and chemistry of undecanoic acid-terminated silicon surfaces: patterning and immobilization of DNA.
2004 Dec 21
X-ray studies of self-assembled organic monolayers grown on hydrogen-terminated Si(111).
2004 Jul 20
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
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
Spectra and kinetic studies of the compound I derivative of cytochrome P450 119.
2008 Oct 8
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
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 Fri Dec 15 15:03:21 GMT 2023
Edited
by admin
on Fri Dec 15 15:03:21 GMT 2023
Record UNII
V50TG7E11W
Record Status Validated (UNII)
Record Version
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Name Type Language
SODIUM UNDECYLENATE
INCI   VANDF   WHO-DD  
INCI  
Official Name English
SODIUM UNDECYLENATE [VANDF]
Common Name English
10-HENDECENOIC ACID, SODIUM SALT
Common Name English
NSC-2836
Code English
UNDECYLENIC ACID SODIUM SALT
Common Name English
SODIUM UNDECYLENATE [INCI]
Common Name English
SODIUM UNDEC-10-ENOATE
Systematic Name English
Sodium undecylenate [WHO-DD]
Common Name English
Code System Code Type Description
PUBCHEM
23667258
Created by admin on Fri Dec 15 15:03:21 GMT 2023 , Edited by admin on Fri Dec 15 15:03:21 GMT 2023
PRIMARY
FDA UNII
V50TG7E11W
Created by admin on Fri Dec 15 15:03:21 GMT 2023 , Edited by admin on Fri Dec 15 15:03:21 GMT 2023
PRIMARY
ECHA (EC/EINECS)
222-264-8
Created by admin on Fri Dec 15 15:03:21 GMT 2023 , Edited by admin on Fri Dec 15 15:03:21 GMT 2023
PRIMARY
CAS
3398-33-2
Created by admin on Fri Dec 15 15:03:21 GMT 2023 , Edited by admin on Fri Dec 15 15:03:21 GMT 2023
PRIMARY
EPA CompTox
DTXSID4037039
Created by admin on Fri Dec 15 15:03:21 GMT 2023 , Edited by admin on Fri Dec 15 15:03:21 GMT 2023
PRIMARY
NSC
2836
Created by admin on Fri Dec 15 15:03:21 GMT 2023 , Edited by admin on Fri Dec 15 15:03:21 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE