UNDECYLENIC ACID MONOETHANOLAMINE

US Approved OTC

First approved in 1945

Details

Stereochemistry	ACHIRAL
Molecular Formula	C11H20O2.C2H7NO
Molecular Weight	245.3584
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of UNDECYLENIC ACID MONOETHANOLAMINE

Structure Search

SMILES

NCCO.OC(=O)CCCCCCCCC=C

InChI

InChIKey=GPOFRJKTYRFQLJ-UHFFFAOYSA-N

InChI=1S/C11H20O2.C2H7NO/c1-2-3-4-5-6-7-8-9-10-11(12)13;3-1-2-4/h2H,1,3-10H2,(H,12,13);4H,1-3H2

HIDE SMILES / InChI

Molecular Formula	C11H20O2
Molecular Weight	184.2753
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C2H7NO
Molecular Weight	61.0831
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.fda.gov/ohrms/dockets/ac/04/briefing/4036B1_06_OTC%20Monograph%20Topical.htm
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
Fatty acid biosynthesis 8 Target ID: map00061 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10991877	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Tinea pedis 28 Sources: https://www.drugs.com/otc/511317/undecylenic-acid.html	Curative	Approved 8583	CRUEX Approved Use For the cure of most tinea pedis (athlete's foot) and tinea corporis (ringworm).
Tinea corporis 19 Sources: https://www.drugs.com/otc/511317/undecylenic-acid.html	Curative	Approved 8583	CRUEX Approved Use For the cure of most tinea pedis (athlete's foot) and tinea corporis (ringworm).
Herpes labialis 8 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9207352	Primary	Phase III 665	Unknown Approved Use Unknown
Itching 52 Sources: https://www.drugs.com/otc/511317/undecylenic-acid.html	Primary	Approved 8583	CRUEX Approved Use Itching, 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 Sources: https://pubmed.ncbi.nlm.nih.gov/15412274	unhealthy, 56 years Health Status: unhealthy Age Group: 56 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/15412274	Disc. AE: Toxic labyrinthitis... AEs leading to discontinuation/dose reduction: Toxic labyrinthitis (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/15412274
1 g 3 times / day multiple, oral Dose: 1 g, 3 times / day Route: oral Route: multiple Dose: 1 g, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/18123174	unhealthy, 8-14 years Health Status: unhealthy Age Group: 8-14 years Sources: https://pubmed.ncbi.nlm.nih.gov/18123174	Sources: https://pubmed.ncbi.nlm.nih.gov/18123174
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: https://pubmed.ncbi.nlm.nih.gov/18123174	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://pubmed.ncbi.nlm.nih.gov/18123174	Sources: https://pubmed.ncbi.nlm.nih.gov/18123174
2 % 1 times / day multiple, topical Dose: 2 %, 1 times / day Route: topical Route: multiple Dose: 2 %, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/832943	unhealthy Health Status: unhealthy Sources: https://pubmed.ncbi.nlm.nih.gov/832943	Sources: https://pubmed.ncbi.nlm.nih.gov/832943

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 Sources: https://pubmed.ncbi.nlm.nih.gov/15412274	unhealthy, 56 years Health Status: unhealthy Age Group: 56 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/15412274

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY41958	https://www.001chemical.com/chem/112-38-9
3B Scientific (Wuhan) Corp	3B3-020016	http://www.3bsc.com/index/pro_info.php?id=28985
AA Blocks	AA003V75	http://www.aablocks.com/goods/Goods/detail?id=AA003V75
Aaron Chemicals	AR003VYX	http://www.aaronchem.com/112-38-9
abcr GmbH	AB125429	http://www.abcr.com/shop/en/AB125429
AbMole Bioscience	M5355	http://www.abmole.com/products/10-undecenoic-acid.html
Acadechem	ACDS-033249	http://www.acadechemical.com/product/107948
Aceschem	ACS015758	https://www.aceschem.com/catalog/112-38-9.html
Achemica	ACMC-2099el	http://www.achemica.com/prodinfo/?id=90214
Achemtek	0104-015714	http://www.achemtek.com/112-38-9
Acros Organics	AC154490025	https://www.fishersci.com/shop/products/undecylenic-acid-99-acros-organics/AC154490025
Acros Organics	AC154492500	https://www.fishersci.com/shop/products/undecylenic-acid-99-acros-organics-1/AC154492500
Acros Organics	AC154495000	https://www.fishersci.com/shop/products/undecylenic-acid-99-acros-organics-1/AC154495000
AEchem Scientific Corp., USA	AE038145	http://www.aechemsc.com/info_products/AE038145.php
Alfa Aesar	A19122	https://www.alfa.com/en/catalog/A19122/
Ambeed	A997538	https://www.ambeed.com/products/112-38-9.html
Angel Pharmatech	AG234213	http://www.angelpharmatech.com/112-38-9.html
Angene	AGN-PC-0JK7BE	http://www.angenechemical.com/productshow/AGN-PC-0JK7BE.html
Anward	ANW-16459	http://www.anward.com/pro_result/3951
Aurum Pharmatech LLC	NE10319	http://www.Aurumpharmatech.com/Product/ProductDetails/NE10319
Avantor Inc	101096-392	https://us.vwr.com/store/catalog/product.jsp?catalog_number=101096-392
BioSynth	W-200840	https://www.biosynth.com/en/products/chemical-intermediates/basic-intermediates/products/W-200840.html
BLD Pharm	BD17568	http://www.bldpharm.com/products/112-38-9.html
Chem Scene	CS-4383	http://www.chemscene.com/112-38-9.html
ChemMol	49426450	http://www.chemmol.com/chemmol/49426450.html
ChemMol	96707545	http://www.chemmol.com/chemmol/96707545.html
Chemspace	CSSB00000211349	https://chem-space.com/CSSB00000211349
Clearsynth	CS-EB-02200	https://www.clearsynth.com/en/CSEB02200.html
Clearsynth	CS-ER-02192	https://www.clearsynth.com/en/CSER02192.html
CSNpharm	CSN12487	https://www.csnpharm.com/products/10-undecenoic-acid.html
DC Chemicals	DC37167	http://www.dcchemicals.com//product_show-Undecylenic_acid.html
Finetech	FT-0607203	http://www.finetechnology-ind.com/prod/detail/pub/112-38-9.html
Glentham Life Sciences	GK3843	http://www.glentham.com/products/product/GK3843/
Hairui	HR135063	http://www.hairuichem.com/en/product/112-38-9.html
iChemical	EBD50537	http://www.ichemical.com/products/112-38-9.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
Lab Network	LN00236754	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00236754
LGC Standards	DRE-C17896710	https://www.lgcstandards.com/US/en/p/DRE-C17896710
mcule	MCULE-7928135942	https://mcule.com/MCULE-7928135942/
MedChem Express	HY-B0914	https://www.medchemexpress.com/10-Undecenoic-acid.html
Molcore	MC41958	https://www.molcore.com/product/112-38-9
MuseChem	I000468	https://www.musechem.com/product/I000468.html
Oakwood	228026	http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=109025&ExtHyperLink=1
Parchem	7073	http://www.parchem.com/chemical-supplier-distributor/10-undecenoic-acid-008960.aspx
Sigma-Aldrich	124672_ALDRICH	https://www.sigmaaldrich.com/catalog/product/aldrich/124672?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	1705505_USP	https://www.sigmaaldrich.com/catalog/product/usp/1705505?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	27817_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/27817?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	73537_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/73537?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	94192_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/94192?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sinfoo Biotech	S017592	http://www.sinfoobiotech.com/product/1020990
Smolecule	S546392	http://www.smolecule.com/products/s546392
Smolecule	S772627	https://www.smolecule.com/products/s772627
TCI (Tokyo Chemical Industry)	U0007	http://www.tcichemicals.com/eshop/en/us/commodity/U0007/index.html
THE BioTek	bt-284989	https://www.thebiotek.com/product/inhibitors/bt-284989
VladaChem	VL272290-100G	https://www.vladachem.com/product.php?products=112-38-9
VladaChem	VL281404-100G	https://www.vladachem.com/product.php?products=112-38-9

PubMed

Title	Date	PubMed
Bioconjugate functionalization of thermally carbonized porous silicon using a radical coupling reaction.	2010-12-07	20967329
Simple surface modification of poly(dimethylsiloxane) for DNA hybridization.	2010-12-06	21264061
Production of functionalized polyhydroxyalkanoates by genetically modified Methylobacterium extorquens strains.	2010-09-16	20846434
Capric acid secreted by S. boulardii inhibits C. albicans filamentous growth, adhesion and biofilm formation.	2010-08-10	20706577
Rapid approach to biobased telechelics through two one-pot thiol-ene click reactions.	2010-06-14	20462176
Simultaneous biosynthesis of two copolymers in Pseudomonas putida GPo1 using a two-stage continuous culture system.	2010-06-14	20459087
Stimulatory effect of undecylenic acid on mouse osteoblast differentiation.	2010-04	19777559
Electrochemical behavior of gold colloidal alkyl modified silicon surfaces.	2009-11	20356117
Porous silicon for photosensitized formation of singlet oxygen in water and in simulated body fluid: two methods of modification by undecylenic acid.	2009-06	19504868
Fed-batch production of unsaturated medium-chain-length polyhydroxyalkanoates with controlled composition by Pseudomonas putida KT2440.	2009-03	19050862
Polymerizable vesicles based on a single-tailed fatty acid surfactant: a simple route to robust nanocontainers.	2009-02-03	19138066
The compatibility of hepatocytes with chemically modified porous silicon with reference to in vitro biosensors.	2009-01	18845334
Undecylenic acid: a valuable and physiologically active renewable building block from castor oil.	2009	19650106
A rapid and sensitive screening system for human type I collagen with the aim of discovering potent anti-aging or anti-fibrotic compounds.	2008-12-31	18810249
Oxidation-triggered release of fluorescent molecules or drugs from mesoporous Si microparticles.	2008-11-25	19206408
Spectra and kinetic studies of the compound I derivative of cytochrome P450 119.	2008-10-08	18788736
Topographical and functional characterization of the ssDNA probe layer generated through EDC-mediated covalent attachment to nanocrystalline diamond using fluorescence microscopy.	2008-08-19	18627188
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).	2008-06	18343554
Genomic analysis of post-mating changes in the honey bee queen (Apis mellifera).	2008-05-19	18489784
A new concept in the topical treatment of onychomycosis with cyanoacrylate, undecylenic acid, and hydroquinone.	2008-04	19825699
Effect of double bonds in the formation of sodium dodecanoate and sodium 10-undecenoate mixed micelles in water.	2007-10-11	17880196
Effects of insemination quantity on honey bee queen physiology.	2007-10-03	17912357
Determination of nateglinide in human plasma by high-performance liquid chromatography with pre-column derivatization using a coumarin-type fluorescent reagent.	2007-09-05	17765074
Enzymatic synthesis of arbutin undecylenic acid ester and its inhibitory effect on melanin synthesis.	2007-06-01	17418566
Covalent biofunctionalization of silicon nitride surfaces.	2007-05-22	17455968
Optimizing biosensing properties on undecylenic Acid-functionalized diamond.	2007-05-08	17419656
Cell adhesion properties on photochemically functionalized diamond.	2007-05-08	17407337
Enzymatic synthesis of arbutin undecylenic acid ester and its inhibitory effect on mushroom tyrosinase.	2007-03	17195058
Mechanisms of thermal decomposition of organic monolayers grafted on (111) silicon.	2007-01-30	17241054
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.	2007-01-30	16919325
Self-assembled monolayers with latent aldehydes for protein immobilization.	2007-01-18	17226979
Nanovectors for anticancer agents based on superparamagnetic iron oxide nanoparticles.	2007	18203422
Self-assembled thermo- and pH responsive micelles of poly(10-undecenoic acid-b-N-isopropylacrylamide) for drug delivery.	2006-12-01	17097179
3,3,5-Trimethylcyclohexanols and derived esters: green synthetic procedures, odour evaluation and in vitro skin cytotoxicity assays.	2006-12	18489288
Grazing angle mirror-backed reflection (GMBR) for infrared analysis of monolayers on silicon.	2006-09-14	16956251
Natural treatment of chronic rhinosinusitis.	2006-09	17217321
EDC-mediated DNA attachment to nanocrystalline CVD diamond films.	2006-08-15	16442276
Controlling electroosmotic flow in poly(dimethylsiloxane) separation channels by means of prepolymer additives.	2006-07-01	16808469
Simple fluorimetric liquid chromatographic method for the analysis of undecylenic acid and zinc undecylenate in pharmaceutical preparations.	2006-06-30	16297927
Synthesis and HPLC evaluation of carboxylic acid phases on a hydride surface.	2006-04	16830499
UV photodissociation spectroscopy of oxidized undecylenic acid films.	2006-03-16	16526639
Tailor-made olefinic medium-chain-length poly[(R)-3-hydroxyalkanoates] by Pseudomonas putida GPo1: batch versus chemostat production.	2006-03-05	16255038
Well-defined carboxyl-terminated alkyl monolayers grafted onto H-Si(111): packing density from a combined AFM and quantitative IR study.	2006-01-03	16378414
Silicon nanoparticles: applications in cell biology and medicine.	2006	17722279
Simple methods for the direct assembly, functionalization, and patterning of acid-terminated monolayers on Si111.	2005-11-08	16262318
Kinetic control of the photochemical reactivity of hydrogen-terminated silicon with bifunctional molecules.	2005-05-24	15896044
Synthesis, stereochemistry and biological activity of some novel long alkyl chain substituted thiazolidin-4-ones and thiazan-4-one from 10-undecenoic acid hydrazide.	2005-02	15694652
Formation, characterization, and chemistry of undecanoic acid-terminated silicon surfaces: patterning and immobilization of DNA.	2004-12-21	15595802
Surface functionalization of silicon nanoparticles produced by laser-driven pyrolysis of silane followed by HF-HNO3 etching.	2004-05-25	15969188
Screening for new compounds with antiherpes activity.	1984-10	6517562

Patents

Sample Use Guides

In Vivo Use Guide

Undecylenic acid antifungal liquid should be applied to affected area topically.

Route of Administration: Topical

In Vitro Use Guide

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 `Mon Mar 31 17:54:40 GMT 2025` Edited by `admin` on `Mon Mar 31 17:54:40 GMT 2025`
Record UNII	89FB3I7256
Record Status	`Validated (UNII)`
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Name

Type

Language

MEA-UNDECYLENATE

Preferred Name

English

UNDECYLENIC ACID MONOETHANOLAMINE

Common Name

English

MONOETHANOLAMINE UNDECYLENATE

Common Name

English

ETHANOL, 2-AMINO-, 10-UNDECENOATE (SALT)

Systematic Name

English

10-UNDECENOIC ACID, COMPD. WITH 2-AMINOETHANOL (1:1)

Systematic Name

English

Code System Code Type Description

EPA CompTox

DTXSID20971980