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CAS Number: 112-37-8
CHEBI:32368
CHEMBL108030
ChemSpider: 7888
ECHA Information Card: 100.003.604
EC Number: 203-964-2
Molecular Weight: 184.28
Undecylic acid (systematically called undecanoic acid) is a carboxylic acid with the chemical formula CH3(CH2)9COOH.
Undecylic acid is often used as an antifungal agent, for example to treat ringworm and athlete's foot.
Like Decanoic acid, Undecylic acid has a distinctive, unpleasant odor.
Undecanoic acid is a white crystalline solid.
It is insoluble in water.
Specific gravity 0.85.
Therefore, it floats on water.
Undecanoic acid is a straight-chain, eleven-carbon saturated medium-chain fatty acid found in body fluids; It is the most fungicidal of the C7:0 - C18:0 fatty acid series.
Undecylic acid acts as a human metabolite and an antifungal agent.
Undecylic acid is a straight-chain saturated fatty acid and a medium-chain fatty acid.
Undecylic acid is the conjugate acid of an undecanoate. It is derived from the hydride of an undecane.
Undecanoic acid is a natural product found in Diplotaxis harra, Blumea aromatica and other organisms with available data.
Definition of Undecylic acid
Undecanoic acid, also known as N-undecylic acid or N-undecanoate, belongs to the class of organic compounds known as medium chain fatty acids.
These are fatty acids with aliphatic tails containing 4 to 12 carbon atoms.
Undecanoic acid is a very hydrophobic molecule, practically insoluble (in water) and relatively neutral.
Undecanoic acid is a potentially toxic compound.
Applications of Undecylic acid
Live User Guide
Combinations of tricyclodecan-9-yl-xanthogenate with undecanoic acid and D 609 with myristic acid (C14) were tested in a rodent tumor model.
Undecanoic acid inhibits conidial germination of UDA-sensitive wild-type Trichophyton rubrum and UDA-resistant mutant strains at the minimum UDA inhibitory concentrations for these two strains at 30 ug/ml and 120 ug/ml, respectively.
Properties of undecylic acid
Chemical formula: C11H22O2
Molar mass1: 86.29 g/mol
Appearance: Colorless crystals
Density: 0.89 g/cm3
Melting point: 28.6 °C (83.5 °F; 301.8 K)
Boiling point: 284 °C (543 °F; 557 K)
Calculated Properties of Undecylic acid
Molecular Weight: 186.29
XLogP3: 3.7
Number of Hydrogen Bond Donors: 1
Number of Hydrogen Bond Acceptors: 2
Number of Rotatable Ties: 9
Full Mass: 186.161979940
Monoisotopic Mass: 186.161979940
Topological Polar Surface Area: 37.3 Å ²
Heavy Atom Count: 13
Net Load: 0
Complexity: 121
Isotope Atomic Number: 0
Number of Atom Stereocenters Defined: 0
Undefined Atom Stereocenter Count: 0
Defined Number of Bond Stereocenters: 0
Undefined Bond Stereocenter Number:0
Number of Covalently Bonded Units: 1
Compound Canonicalized: Yes
Chemical Formula: C11H22O2
Average Molecular Weight: 186.2912
Monoisotopic Molecular Weight: 186.161979948
IUPAC Name: undecanoic acid
Traditional Name: undecanoic acid
CAS Registry Number: 112-37-8
InChI Identifier
InChI=1S/C11H22O2/c1-2-3-4-5-6-7-8-9-10-11(12)13/h2-10H2,1H3,(H,12,13)
InChI Switch: ZDPHROOEEOARMN-UHFFFAOYSA-N
Chemical Taxonomy of Undecylic Acid
Definition
It belongs to the class of organic compounds known as medium chain fatty acids.
These are fatty acids with aliphatic tails containing 4 to 12 carbon atoms.
Kingdom: Organic compounds
Superclass: Lipids and lipid-like molecules
Class: Oil Nobles
Subclass: Fatty acids and their conjugates
Direct Parent: Medium chain fatty acids
Alternative Parents
straight chain fatty acids
Monocarboxylic acids and their derivatives
Carboxylic acids
organic oxides
hydrocarbon derivatives
carbonyl compounds
substitutions
medium chain fatty acid
straight chain fatty acid
Monocarboxylic acid or derivatives
carboxylic acid
carboxylic acid derivative
organic oxygen compound
organic oxide
hydrocarbon derivative
organoxygen compound
carbonyl group
aliphatic acyclic compound
Molecular Framework: Aliphatic acyclic compounds
External Identifiers of Undecylic Acid
medium chain fatty acid (CHEBI:32368)
straight chain saturated fatty acid (CHEBI:32368)
Straight chain fatty acids (C17715)
Straight chain fatty acids (LMFA01010011)
Physical properties of Undecylic Acid
Condition: Solid
Experimental Molecular Properties of Undecylic Acid
Melting Point: 28.6 °C
Boiling Point: Not Available
Solubility in Water: 0.052 mg/mL
DailyP: 4.42
IUPHAR/BPS :5533
KEGG Number: C17715
PubChem Client ID: 8180
UNII: 138ON3IIQG
CAS Number: 112-37-8
FEMA Number: 3247
Color Index Number: 42650
Beilstein: 1762631
EC Number: 203-964-2
Council of Europe no.: 689
MDL number: MFCD00004442
PubChem Item ID: 8180
Flavis number: 8.039
Predicted Molecular Properties of Undecylic Acid
Solubility in Water: 0.023 g/L
logP: 10(4.49) g/L
logP: 10(4.03) g/L
logS: 10(-3,9) g/L
pKa (Strongest Acidic): 4.95
Physiological Load: -1
Number of Hydrogen Acceptors: 2
Number of Hydrogen Donors: 1
Pole Surface Area: 37.3 Ų
Number of Rotatable Ties: 9
Refraction: 54.08 m³ mol ⁻ ¹
Polarizability: 23.73 ų
Number of Rings: 0
Bioavailability: Yes
Rule of Five: Yes
Ghose Filter: Yes
Veber Rule: Yes
MDDR-like Rule: No
Chemical name: Undecanoic acid
JECFA number: 108
CAS number: 112-37-8
FEMA number: 3245
COE number: 696
Molecular weight: 186.29
Chemical formula: C11H22O2
Physical form/odor: colorless crystals/pale oily, aldehyde odor
Solubility: Insoluble in water; very soluble in alcohol, chloroform, acetone
Boiling point (°C): 284°
Test min %: 99%
Acid value max: 295-301
Index of refraction: 1.4355 (30°)
Specific gravity: 0.9948 (20°/20°)
Other requirements: Melting point: 33-38°
Undecylic Acid Properties
min. Purity Feature: 98% (GC)
Spectrum:GCMS, FT-IR, GC
Physical Form (at 20°C): Off-white solid
Melting Point: 28-31°C
Boiling Point: 248-250°C
Flash Point: 113°C
Long-Term Storage: Store in a cool, dry place for a long time.
Physical and Chemical Properties of Undecylic Acid
MELTING POINT : 29.3degC
BOILING POINT : 284.0degC
FRACTURE INDEX: 1.4202 at 70degC
DENSITY :d4-25 0.9905
SOLUBILITY: soluble in alcohol, chloroform and ether.
Only use undecylic acid on the skin.
Clean the area to be treated and dry thoroughly.
Apply Undecylic acid to the affected skin, usually twice a day or as directed by your doctor or product package.
The dosage and duration of treatment depend on the type of infection being treated.
Apply enough medicine to cover the affected area and some of the surrounding skin.
Wash your hands after applying undecylic acid.
Do not wrap, cover, or bandage the area with undecylic acid.
Do not apply undecylic acid to the eyes, nose, mouth, or vagina.
If this occurs, rinse with plenty of water.
If irritation occurs, contact your doctor immediately.
Use it regularly to get the most out of undecylic acid.
Remember to use it at the same times every day.
Continue to use undecylic acid for the period specified by your doctor or product package, even if symptoms disappear after starting this product.
Stopping this medication too soon may allow the fungus to continue to grow, which can cause the infection to return.
Tell your doctor if your condition persists or worsens after 2 to 4 weeks, or if you think you may have a serious medical problem.
Product Information of Undecylic Acid
Documentation:
Certificate of analysis
purity: >99%
Storage: Room temperature
Provided as: Clean
Smiles:CCCCCCCCCC(=O)O
Molecular formula: C11H22O2
Molecular weight: 186.29117
Physical state:Solid
Lipid number: C11:0
Biological activity of Undecylic Acid
Definition
Undecanoic acid is a medium chain monocarboxylic acid that appears to play a role in the control of triacylglycerol synthesis.
Density: 0.89 g/mL at 20 °C
Chemical Formula: C11H22O2
IUPAC name: undecanoic acid
InChI Identifier
InChI=1S/C11H22O2/c1-2-3-4-5-6-7-8-9-10-11(12)13/h2-10H2,1H3,(H,12,13)
InChI Switch: ZDPHROOEEOARMN-UHFFFAOYSA-N
Average Molecular Weight: 186.2912
Monoisotopic Molecular Weight: 186.161979948
Structure of Undecylic Acid
Stereochemistry: ACHIRAL
Molecular Formula: C11H22O2
Molecular Weight: 186.2916
Optical Efficiency: NONE
Defined Stereocenters: 0 / 0
E/Z Centers: 0
Load: 0
Definition of Undecylic Acid
Undecanoic acid is a fatty acid with significant antimycotic activity.
Undecanoic acid is a straight-chain, eleven-carbon saturated medium-chain fatty acid found in body fluids; It is the most fungicidal of the C7:0 - C18:0 fatty acid series.
Undecylic acid acts as a human metabolite and an antifungal agent.
It is a straight chain saturated fatty acid and a medium chain fatty acid.
Undecylic acid is the conjugate acid of an undecanoate.
It is derived from the hydride of an undecane.
Undecanoic acid inhibits exocellular lipase and keratinase production, but stimulates exocellular phospholipase A production in the T. rubrum undecanoic acid-resistant mutant (udar).
At the minimum inhibitory concentration of undecylic acid, undecanoic acid inhibits the biosynthesis of phosphatidyl serine, phosphatidyl ethanolamine, and polyphosphoinositol, but does not inhibit the synthesis of phosphatidyl glycerol, phosphatidyl choline, phosphatidyl inositol, and phosphatidic acid in Trichophyton rubrum.
However, at higher concentration, UDA inhibits the biosynthesis of all phosphatide present in this dermatophyte.
UDA also affects the catabolism of these phosphatides.
This inhibitory effect of UDA may be partially responsible for its toxic effect on T. rubrum.
Properties of Undecylic Acid
Name: Undecanoic acid
CAS Registry Number: 112-37-8
Classification: Medium chain fatty acids
Formula: C11H22O2
InChI : InChI=1S/C11H22O2/c1-2-3-4-5-6-7-8-9-10-11(12)13/h2-10H2,1H3,(H,12,13)
InChIKey: ZDPHROOEEOARMN-UHFFFAOYSA-N
splash: splash10-074l-9100000000-471e121b38370a56f539
Source of the Spectrum: PR-1562-0-0
SpectraBase Batch ID: 8T9Hl7A7WjT
What is undecylic acid topical?
Undecylic acid is a fatty acid that works by preventing fungus from growing on the skin.
Undecylic acid topical (for the skin) is used to treat skin infections caused by fungi, such as athlete's foot, jock itch, or ringworm.
Undecylic acid topical may also be used for purposes not listed in this medication guide.
Answer Suggestions
Insulation and Evacuation
No information available.
Fire extinguishing
Extinguishing Media to Avoid: Water may not be effective.
Extinguishing Media: Carbon dioxide, dry chemical, alcohol foam, water spray.
Non-Fire Intervention
Neutralizing Agents for Acids and Caustics: Sodium bicarbonate solution
protective clothing
No information available.
First aid
INHALATION: Get medical attention.
Remove victim to fresh air.
If not breathing, give artificial respiration.
If breathing is difficult, give oxygen.
EYES OR SKIN: Flush with plenty of water for at least 15 minutes.
Ensure adequate rinsing of eyes by separating eyelids with fingers.
Physical properties of Undecylic Acid
Chemical Formula: C11H22O2
Flash Point: Greater than 230°F
Melting Point: 83.3°F
Vapor Pressure: data not available
Vapor Density (By Air): no data available
Specific Gravity: 0.891
Boiling Point: 442.2°F at 160mm Hg
Molecular Weight: 186.3
Solubility in Water: no data available
Ionization Potential: data not available
IDLH: data not available
FEATURES
CAS No.: 112-37-8
Formula: C11H22O2
CH3 (CH2)9 COOH
Mole. Weight: 186.3
Purity: 98% by GC Min.
Description: Colorless to pale yellow liquid or crystalline mass
Acid Value: 296 – 304
Saponification Value: 296-304
Iodine Value: 2 max
Freezing Point: 27oC – 29oC
Background of Undecylic Acid
Undecylic acid is an unsaturated fatty acid with a terminal double bond derived from castor oil.
Undecylic acid is also found naturally in human sweat.
Undecylic acid is used as a precursor in the manufacture of aromatic chemicals, polymers or modified silicones.
Undecylic acid was first isolated in 1877 from products obtained from the distillation of castor oil by pyrolysis of ricinoleic acid and polymerized for vinyl production.
It has been suggested that undecylic acid, many organic fatty acids, exert fungicidal or fungistatic effects.
Undecylic acid also has anti-fungal properties, but it is never used alone for anti-fungal purposes.
Undecylic acid salts are available in over-the-counter or blend products as antifungal agents.
Zinc Undecylic acid is an example of a topical antifungal agent that treats skin infections such as athlete's foot and relieves itching, burning, and irritation associated with the skin condition.
Due to the bifunctional properties of undecylic acid, undecylenate is also used as a linker molecule to conjugate other biomolecules such as proteins.
Undecylic acid acts as an acid moiety for the anabolic steroid boldenone.
pharmacodynamics
Undecylic acid acts as a fungistatic agent, but fungicidal activity can be observed at chronic exposure at high concentrations.
Undecylic acid is effective against Candida albicans.
It has been suggested that undecylenic acid exerts antimicrobial effects by interacting with non-specific components in the cell membrane.
Mechanism of Action of Undecylic Acid
Undecylic acid has shown activity against Candida albicans, an opportunistic pathogenic yeast with two cellular morphologies: the round yeast form and the long hyphae filamentous form.
Hyphae formation is associated with active infections and virulence.
One study suggested that undecylic acid at an optimal concentration above 3 mM inhibits biofilm formation of Candida albicans, and at a concentration above 4 mM impairs hyphae growth, the morphological transition from yeast to filamentous phase.
Under drug treatment, genes involved in hyphal formation, such as HWP1, are significantly reduced at the transcriptional level, leading to poor biofilm formation.
Both biofilm and hyphae formation are critical virulence factors for the onset of skin infection and late development of disseminated infection.
Undecylic acid can also inhibit the enzyme involved in lipid metabolism and eliminate germ tube formation by transporting protons across the plasma membrane, thereby changing the cytoplasmic pH 3.
Absorption of Undecylic Acid
Undecylic acid can be absorbed from the skin MSDS.
distribution volume
There is no information about the volume of distribution.
Synonyms of Undecylic Acid
UNDECAOIC ACID
112-37-
hendecanoic acid
undecylic acid
undecanoate
n-Undecanoic acid
n-Undecoic acid
n-Undecylic acid
undecoic acid
1-Decanecarboxylic acid
FEMA No. 3245
undecanoic acid
undecansaeure
UNII-138ON3IIQG
CHEBI:32368
NSC-7885
MFCD00002730
undecanoate; Hendecanoic acid
138ON3IIQG
NSC7885
1-decanecarboxylate
C11:0
Undecanoate [USA]
NSC 7885
EINECS 203-964-2
BRN 1759287AI3-02280
undecansäure
Undecanoic acid, 98%
ACMC-1C9TV
DSSTox_CID_1690
bmse000563
SCHEMBL9266
DSSTox_RID_76286
NCIOpen2_009435
DSSTox_GSID_21690
Alternative Name(s)
1-Decanecarboxylic acid
hendecanoic acid
n-Undecanoic acid
n-Undecoic acid
n-Undecylic acid
undecoic acid
undecylic acid
AI3-02280
BRN 1759287
EINECS 203-964-2
FEMA NO. 3245
NSC 788
