UNDECYLENIC ACID

US Approved OTC

First approved in 1945

Details

Stereochemistry	ACHIRAL
Molecular Formula	C11H20O2
Molecular Weight	184.2753
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)CCCCCCCCC=C

InChI

InChIKey=FRPZMMHWLSIFAZ-UHFFFAOYSA-N

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

HIDE SMILES / InChI

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 8297

Conditions

Condition	Modality	Highest Phase	Product
Tinea pedis 28 Sources: https://www.drugs.com/otc/511317/undecylenic-acid.html	Curative	Approved 8429	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 8429	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 656	Unknown Approved Use Unknown
Itching 54 Sources: https://www.drugs.com/otc/511317/undecylenic-acid.html	Primary	Approved 8429	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 Co-administed with:: nicotinic acid(50 mgm. morning and night) Sources: https://pubmed.ncbi.nlm.nih.gov/15412274	unhealthy, 56 years n = 1 Health Status: unhealthy Condition: psoriasis Age Group: 56 years Sex: M Population Size: 1 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 n = 4 Health Status: unhealthy Condition: psoriasis \| NEURODERMATITIS Age Group: 8-14 years Population Size: 4 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 Condition: psoriasis 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 Co-administed with:: zinc undecylenate(0.2) Sources: https://pubmed.ncbi.nlm.nih.gov/832943	unhealthy n = 29 Health Status: unhealthy Condition: TINEA PEDIS Population Size: 29 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 Co-administed with:: nicotinic acid(50 mgm. morning and night) Sources: https://pubmed.ncbi.nlm.nih.gov/15412274	unhealthy, 56 years n = 1 Health Status: unhealthy Condition: psoriasis Age Group: 56 years Sex: M Population Size: 1 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
AEchem Scientific Corp., USA	AE038145	http://www.aechemsc.com/info_products/AE038145.php
Aaron Chemicals	AR003VYX	http://www.aaronchem.com/112-38-9
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	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
Acros Organics	AC154490025	https://www.fishersci.com/shop/products/undecylenic-acid-99-acros-organics/AC154490025
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
BLD Pharm	BD17568	http://www.bldpharm.com/products/112-38-9.html
BioSynth	W-200840	https://www.biosynth.com/en/products/chemical-intermediates/basic-intermediates/products/W-200840.html
CSNpharm	CSN12487	https://www.csnpharm.com/products/10-undecenoic-acid.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
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
LGC Standards	DRE-C17896710	https://www.lgcstandards.com/US/en/p/DRE-C17896710
Lab Network	LN00236754	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00236754
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	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
Sigma-Aldrich	1705505_USP	https://www.sigmaaldrich.com/catalog/product/usp/1705505?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
abcr GmbH	AB125429	http://www.abcr.com/shop/en/AB125429
iChemical	EBD50537	http://www.ichemical.com/products/112-38-9.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
mcule	MCULE-7928135942	https://mcule.com/MCULE-7928135942/

PubMed

Title	Date	PubMed
Screening for new compounds with antiherpes activity.	1984 Oct	6517562
Antioxidant and cyclooxygenase activities of fatty acids found in food.	2002 Apr 10	11929276
Mutations in erg4 affect the sensitivity of Saccharomyces cerevisiae to medium-chain fatty acids.	2002 Apr 15	12020638
One-pot sequences of reactions with sol-gel entrapped opposing reagents: an enzyme and metal-complex catalysts.	2002 Dec 4	12452722
Undecylenic acid. Monograph.	2002 Feb	11896747
Determination of undecylenic and sorbic acids in cosmetic preparations by high performance liquid chromatography with electrochemical detection.	2002 Nov 7	12408884
Enzymatic synthesis of hydrophilic undecylenic acid sugar esters and their biodegradability.	2003 Jan	12882293
Silicon nanoparticles: applications in cell biology and medicine.	2006	17722279
3,3,5-Trimethylcyclohexanols and derived esters: green synthetic procedures, odour evaluation and in vitro skin cytotoxicity assays.	2006 Dec	18489288
Self-assembled thermo- and pH responsive micelles of poly(10-undecenoic acid-b-N-isopropylacrylamide) for drug delivery.	2006 Dec 1	17097179
Well-defined carboxyl-terminated alkyl monolayers grafted onto H-Si(111): packing density from a combined AFM and quantitative IR study.	2006 Jan 3	16378414
Simple fluorimetric liquid chromatographic method for the analysis of undecylenic acid and zinc undecylenate in pharmaceutical preparations.	2006 Jun 30	16297927
Nanovectors for anticancer agents based on superparamagnetic iron oxide nanoparticles.	2007	18203422
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	16919325
Enzymatic synthesis of arbutin undecylenic acid ester and its inhibitory effect on melanin synthesis.	2007 Jun 1	17418566
Enzymatic synthesis of arbutin undecylenic acid ester and its inhibitory effect on mushroom tyrosinase.	2007 Mar	17195058
Covalent biofunctionalization of silicon nitride surfaces.	2007 May 22	17455968
Cell adhesion properties on photochemically functionalized diamond.	2007 May 8	17407337
Effect of double bonds in the formation of sodium dodecanoate and sodium 10-undecenoate mixed micelles in water.	2007 Oct 11	17880196
Effects of insemination quantity on honey bee queen physiology.	2007 Oct 3	17912357
Determination of nateglinide in human plasma by high-performance liquid chromatography with pre-column derivatization using a coumarin-type fluorescent reagent.	2007 Sep 5	17765074
A new concept in the topical treatment of onychomycosis with cyanoacrylate, undecylenic acid, and hydroquinone.	2008 Apr	19825699
Topographical and functional characterization of the ssDNA probe layer generated through EDC-mediated covalent attachment to nanocrystalline diamond using fluorescence microscopy.	2008 Aug 19	18627188
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	18810249
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	18343554
Genomic analysis of post-mating changes in the honey bee queen (Apis mellifera).	2008 May 19	18489784
Oxidation-triggered release of fluorescent molecules or drugs from mesoporous Si microparticles.	2008 Nov 25	19206408
Spectra and kinetic studies of the compound I derivative of cytochrome P450 119.	2008 Oct 8	18788736
Undecylenic acid: a valuable and physiologically active renewable building block from castor oil.	2009	19650106
Polymerizable vesicles based on a single-tailed fatty acid surfactant: a simple route to robust nanocontainers.	2009 Feb 3	19138066
The compatibility of hepatocytes with chemically modified porous silicon with reference to in vitro biosensors.	2009 Jan	18845334
Porous silicon for photosensitized formation of singlet oxygen in water and in simulated body fluid: two methods of modification by undecylenic acid.	2009 Jun	19504868
Fed-batch production of unsaturated medium-chain-length polyhydroxyalkanoates with controlled composition by Pseudomonas putida KT2440.	2009 Mar	19050862
Electrochemical behavior of gold colloidal alkyl modified silicon surfaces.	2009 Nov	20356117
Stimulatory effect of undecylenic acid on mouse osteoblast differentiation.	2010 Apr	19777559
Capric acid secreted by S. boulardii inhibits C. albicans filamentous growth, adhesion and biofilm formation.	2010 Aug 10	20706577
Simple surface modification of poly(dimethylsiloxane) for DNA hybridization.	2010 Dec 6	21264061
Bioconjugate functionalization of thermally carbonized porous silicon using a radical coupling reaction.	2010 Dec 7	20967329
Rapid approach to biobased telechelics through two one-pot thiol-ene click reactions.	2010 Jun 14	20462176
Simultaneous biosynthesis of two copolymers in Pseudomonas putida GPo1 using a two-stage continuous culture system.	2010 Jun 14	20459087
Production of functionalized polyhydroxyalkanoates by genetically modified Methylobacterium extorquens strains.	2010 Sep 16	20846434

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.

Name

Type

Language

UNDECYLENIC ACID

Official Name

English

10-Undecenoic acid

Systematic Name

English

UNDECENOIC ACID

Systematic Name

English

UNDECENOIC ACID [MART.]

Common Name

English

UNDECYLENIC ACID [USP MONOGRAPH]

Common Name

English

UNDECYLENIC ACID [MI]

Common Name

English

UNDECYLENIC ACID [II]

Common Name

English

UNDECYLENIC ACID [EP MONOGRAPH]

Common Name

English

UNDECYLENIC ACID [USP-RS]

Common Name

English

10-UNDECENOIC ACID [FHFI]

Common Name

English

UNDECYLENIC ACID [VANDF]

Common Name

English

UNDECYLENATE

Common Name

English

UNDECYLENIC ACID [INCI]

Common Name

English

UNDECYLENIC ACID [JAN]

Common Name

English

FEMA NO. 3247

Code

English

NSC-2013

Code

English

UNDECYLENATE [VANDF]

Common Name

English

Undecylenic acid [WHO-DD]

Common Name

English

Classification Tree Code System Code

DSLD

2995 (Number of products:4)