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Details

Stereochemistry ACHIRAL
Molecular Formula 2C11H19O2.Zn
Molecular Weight 431.944
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ZINC UNDECYLENATE

SMILES

[Zn++].[O-]C(=O)CCCCCCCCC=C.[O-]C(=O)CCCCCCCCC=C

InChI

InChIKey=YMCOHQVWOBMDCZ-UHFFFAOYSA-L
InChI=1S/2C11H20O2.Zn/c2*1-2-3-4-5-6-7-8-9-10-11(12)13;/h2*2H,1,3-10H2,(H,12,13);/q;;+2/p-2

HIDE SMILES / InChI

Molecular Formula Zn
Molecular Weight 65.409
Charge 2
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
Antioxidant and cyclooxygenase activities of fatty acids found in food.
2002 Apr 10
Enzymatic synthesis of hydrophilic undecylenic acid sugar esters and their biodegradability.
2003 Jan
X-ray studies of self-assembled organic monolayers grown on hydrogen-terminated Si(111).
2004 Jul 20
3,3,5-Trimethylcyclohexanols and derived esters: green synthetic procedures, odour evaluation and in vitro skin cytotoxicity assays.
2006 Dec
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
Oxidation-triggered release of fluorescent molecules or drugs from mesoporous Si microparticles.
2008 Nov 25
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
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
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
Bioconjugate functionalization of thermally carbonized porous silicon using a radical coupling reaction.
2010 Dec 7
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 15:01:08 GMT 2023
Edited
by admin
on Fri Dec 15 15:01:08 GMT 2023
Record UNII
388VZ25DUR
Record Status Validated (UNII)
Record Version
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Name Type Language
ZINC UNDECYLENATE
EP   INCI   JAN   USP   VANDF   WHO-DD  
INCI  
Official Name English
ZINC UNDECYLENATE [JAN]
Common Name English
UNDECYLENIC ACID ZINC SALT
MI  
Common Name English
ZINC UNDECYLENATE [VANDF]
Common Name English
ZINC UNDECENOATE [MART.]
Common Name English
NSC-402438
Code English
ZINC UNDECYLENATE [INCI]
Common Name English
ZINC UNDECENOATE
MART.  
Systematic Name English
Zinc undecylenate [WHO-DD]
Common Name English
ZINC UNDECYLENATE [USP MONOGRAPH]
Common Name English
10-UNDECENOIC ACID, ZINC (2+) SALT
Common Name English
UNDECYLENIC ACID ZINC SALT [MI]
Common Name English
ZINC UNDECYLENATE [EP MONOGRAPH]
Common Name English
UNDECYLENATE ZINC
VANDF  
Common Name English
Zinc 10-undecenoate
Systematic Name English
UNDECYLENATE ZINC [VANDF]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C514
Created by admin on Fri Dec 15 15:01:08 GMT 2023 , Edited by admin on Fri Dec 15 15:01:08 GMT 2023
CFR 21 CFR 333.210
Created by admin on Fri Dec 15 15:01:08 GMT 2023 , Edited by admin on Fri Dec 15 15:01:08 GMT 2023
Code System Code Type Description
SMS_ID
100000089534
Created by admin on Fri Dec 15 15:01:08 GMT 2023 , Edited by admin on Fri Dec 15 15:01:08 GMT 2023
PRIMARY
EVMPD
SUB15763MIG
Created by admin on Fri Dec 15 15:01:08 GMT 2023 , Edited by admin on Fri Dec 15 15:01:08 GMT 2023
PRIMARY
NSC
402438
Created by admin on Fri Dec 15 15:01:08 GMT 2023 , Edited by admin on Fri Dec 15 15:01:08 GMT 2023
PRIMARY
ECHA (EC/EINECS)
209-155-0
Created by admin on Fri Dec 15 15:01:08 GMT 2023 , Edited by admin on Fri Dec 15 15:01:08 GMT 2023
PRIMARY
NCI_THESAURUS
C29552
Created by admin on Fri Dec 15 15:01:08 GMT 2023 , Edited by admin on Fri Dec 15 15:01:08 GMT 2023
PRIMARY
RXCUI
89748
Created by admin on Fri Dec 15 15:01:08 GMT 2023 , Edited by admin on Fri Dec 15 15:01:08 GMT 2023
PRIMARY RxNorm
PUBCHEM
11179
Created by admin on Fri Dec 15 15:01:08 GMT 2023 , Edited by admin on Fri Dec 15 15:01:08 GMT 2023
PRIMARY
FDA UNII
388VZ25DUR
Created by admin on Fri Dec 15 15:01:08 GMT 2023 , Edited by admin on Fri Dec 15 15:01:08 GMT 2023
PRIMARY
DRUG BANK
DBSALT001529
Created by admin on Fri Dec 15 15:01:08 GMT 2023 , Edited by admin on Fri Dec 15 15:01:08 GMT 2023
PRIMARY
MERCK INDEX
m11303
Created by admin on Fri Dec 15 15:01:08 GMT 2023 , Edited by admin on Fri Dec 15 15:01:08 GMT 2023
PRIMARY Merck Index
DAILYMED
388VZ25DUR
Created by admin on Fri Dec 15 15:01:08 GMT 2023 , Edited by admin on Fri Dec 15 15:01:08 GMT 2023
PRIMARY
RS_ITEM_NUM
1724780
Created by admin on Fri Dec 15 15:01:08 GMT 2023 , Edited by admin on Fri Dec 15 15:01:08 GMT 2023
PRIMARY
CAS
557-08-4
Created by admin on Fri Dec 15 15:01:08 GMT 2023 , Edited by admin on Fri Dec 15 15:01:08 GMT 2023
PRIMARY
EPA CompTox
DTXSID90890497
Created by admin on Fri Dec 15 15:01:08 GMT 2023 , Edited by admin on Fri Dec 15 15:01:08 GMT 2023
PRIMARY
DRUG CENTRAL
4457
Created by admin on Fri Dec 15 15:01:08 GMT 2023 , Edited by admin on Fri Dec 15 15:01:08 GMT 2023
PRIMARY
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PARENT -> SALT/SOLVATE
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ACTIVE MOIETY