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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 of UNDECYLENIC ACID

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

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

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
Application of linear solvation energy relationships to polymeric pseudostationary phases in micellar electrokinetic chromatography.
2001 Apr
Convenient formation of 4-hydroxyalk-2-en-1-one functionality via A knoevenagel-type carbon chain elongation reaction of aldehyde with 1-arylsulfinylalkan-2-one.
2001 Feb 23
Antioxidant and cyclooxygenase activities of fatty acids found in food.
2002 Apr 10
Mutations in erg4 affect the sensitivity of Saccharomyces cerevisiae to medium-chain fatty acids.
2002 Apr 15
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
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
Synthesis and HPLC evaluation of carboxylic acid phases on a hydride surface.
2006 Apr
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
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
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
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 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
Oxidation-triggered release of fluorescent molecules or drugs from mesoporous Si microparticles.
2008 Nov 25
Polymerizable vesicles based on a single-tailed fatty acid surfactant: a simple route to robust nanocontainers.
2009 Feb 3
Electrochemical behavior of gold colloidal alkyl modified silicon surfaces.
2009 Nov
Stimulatory effect of undecylenic acid on mouse osteoblast differentiation.
2010 Apr
Simultaneous biosynthesis of two copolymers in Pseudomonas putida GPo1 using a two-stage continuous culture system.
2010 Jun 14
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 15:09:42 GMT 2023
Edited
by admin
on Fri Dec 15 15:09:42 GMT 2023
Record UNII
K3D86KJ24N
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
UNDECYLENIC ACID
EP   II   INCI   JAN   MI   USP   USP-RS   VANDF   WHO-DD  
INCI  
Official Name English
10-Undecenoic acid
FHFI  
Systematic Name English
UNDECENOIC ACID
MART.  
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
VANDF  
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)
Created by admin on Fri Dec 15 15:09:42 GMT 2023 , Edited by admin on Fri Dec 15 15:09:42 GMT 2023
WHO-VATC QD01AE54
Created by admin on Fri Dec 15 15:09:42 GMT 2023 , Edited by admin on Fri Dec 15 15:09:42 GMT 2023
DSLD 3453 (Number of products:1)
Created by admin on Fri Dec 15 15:09:42 GMT 2023 , Edited by admin on Fri Dec 15 15:09:42 GMT 2023
WHO-VATC QD01AE04
Created by admin on Fri Dec 15 15:09:42 GMT 2023 , Edited by admin on Fri Dec 15 15:09:42 GMT 2023
JECFA EVALUATION 10-UNDECENOIC ACID
Created by admin on Fri Dec 15 15:09:42 GMT 2023 , Edited by admin on Fri Dec 15 15:09:42 GMT 2023
WHO-ATC D01AE04
Created by admin on Fri Dec 15 15:09:42 GMT 2023 , Edited by admin on Fri Dec 15 15:09:42 GMT 2023
CFR 21 CFR 333.210
Created by admin on Fri Dec 15 15:09:42 GMT 2023 , Edited by admin on Fri Dec 15 15:09:42 GMT 2023
WHO-ATC D01AE54
Created by admin on Fri Dec 15 15:09:42 GMT 2023 , Edited by admin on Fri Dec 15 15:09:42 GMT 2023
EPA PESTICIDE CODE 85501
Created by admin on Fri Dec 15 15:09:42 GMT 2023 , Edited by admin on Fri Dec 15 15:09:42 GMT 2023
NCI_THESAURUS C514
Created by admin on Fri Dec 15 15:09:42 GMT 2023 , Edited by admin on Fri Dec 15 15:09:42 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID8035001
Created by admin on Fri Dec 15 15:09:42 GMT 2023 , Edited by admin on Fri Dec 15 15:09:42 GMT 2023
PRIMARY
CAS
112-38-9
Created by admin on Fri Dec 15 15:09:42 GMT 2023 , Edited by admin on Fri Dec 15 15:09:42 GMT 2023
PRIMARY
WIKIPEDIA
UNDECYLENIC ACID
Created by admin on Fri Dec 15 15:09:42 GMT 2023 , Edited by admin on Fri Dec 15 15:09:42 GMT 2023
PRIMARY
RS_ITEM_NUM
1705505
Created by admin on Fri Dec 15 15:09:42 GMT 2023 , Edited by admin on Fri Dec 15 15:09:42 GMT 2023
PRIMARY
ECHA (EC/EINECS)
203-965-8
Created by admin on Fri Dec 15 15:09:42 GMT 2023 , Edited by admin on Fri Dec 15 15:09:42 GMT 2023
PRIMARY
CHEBI
39448
Created by admin on Fri Dec 15 15:09:42 GMT 2023 , Edited by admin on Fri Dec 15 15:09:42 GMT 2023
PRIMARY
SMS_ID
100000091959
Created by admin on Fri Dec 15 15:09:42 GMT 2023 , Edited by admin on Fri Dec 15 15:09:42 GMT 2023
PRIMARY
DAILYMED
K3D86KJ24N
Created by admin on Fri Dec 15 15:09:42 GMT 2023 , Edited by admin on Fri Dec 15 15:09:42 GMT 2023
PRIMARY
FDA UNII
K3D86KJ24N
Created by admin on Fri Dec 15 15:09:42 GMT 2023 , Edited by admin on Fri Dec 15 15:09:42 GMT 2023
PRIMARY
DRUG CENTRAL
3446
Created by admin on Fri Dec 15 15:09:42 GMT 2023 , Edited by admin on Fri Dec 15 15:09:42 GMT 2023
PRIMARY
CHEBI
35045
Created by admin on Fri Dec 15 15:09:42 GMT 2023 , Edited by admin on Fri Dec 15 15:09:42 GMT 2023
PRIMARY
RXCUI
10989
Created by admin on Fri Dec 15 15:09:42 GMT 2023 , Edited by admin on Fri Dec 15 15:09:42 GMT 2023
PRIMARY
EVMPD
SUB15654MIG
Created by admin on Fri Dec 15 15:09:42 GMT 2023 , Edited by admin on Fri Dec 15 15:09:42 GMT 2023
PRIMARY
MESH
C538763
Created by admin on Fri Dec 15 15:09:42 GMT 2023 , Edited by admin on Fri Dec 15 15:09:42 GMT 2023
PRIMARY
RXCUI
314881
Created by admin on Fri Dec 15 15:09:42 GMT 2023 , Edited by admin on Fri Dec 15 15:09:42 GMT 2023
ALTERNATIVE
NCI_THESAURUS
C29530
Created by admin on Fri Dec 15 15:09:42 GMT 2023 , Edited by admin on Fri Dec 15 15:09:42 GMT 2023
PRIMARY
MERCK INDEX
m11303
Created by admin on Fri Dec 15 15:09:42 GMT 2023 , Edited by admin on Fri Dec 15 15:09:42 GMT 2023
PRIMARY Merck Index
JECFA MONOGRAPH
373
Created by admin on Fri Dec 15 15:09:42 GMT 2023 , Edited by admin on Fri Dec 15 15:09:42 GMT 2023
PRIMARY
ChEMBL
CHEMBL1276010
Created by admin on Fri Dec 15 15:09:42 GMT 2023 , Edited by admin on Fri Dec 15 15:09:42 GMT 2023
PRIMARY
NSC
2013
Created by admin on Fri Dec 15 15:09:42 GMT 2023 , Edited by admin on Fri Dec 15 15:09:42 GMT 2023
PRIMARY
DRUG BANK
DB11117
Created by admin on Fri Dec 15 15:09:42 GMT 2023 , Edited by admin on Fri Dec 15 15:09:42 GMT 2023
PRIMARY
PUBCHEM
5634
Created by admin on Fri Dec 15 15:09:42 GMT 2023 , Edited by admin on Fri Dec 15 15:09:42 GMT 2023
PRIMARY
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