Undecenoic acid

Undecenoic acid
Compound Structure:
Synonyms: undecylenic acid ;10-UNDECENOIC ACID; Undec-10-enoic acid; 112-38-9 ;Undecenoic acid
Compound ID: NMPC-1584
PubChem ID:

5634

Molecular Formula: C11H20O2
Canonical SMILES: C=CCCCCCCCCC(=O)O
InChIKey: FRPZMMHWLSIFAZ-UHFFFAOYSA-N
About the compound:

10-undecenoic acid is an undecenoic acid having its double bond in the 10-position. It is derived from castor oil and is used for the treatment of skin problems. It has a role as a plant metabolite and an antifungal drug. It is a conjugate acid of a 10-undecenoate. Undecylenate, or undecylenic acid, is an unsaturated fatty acid with a terminal double bond that is derived from castor oil. Undecylenic acid is also found naturally in the human sweat. It is used as a precursor in the manufacture of aromatic chemicals, polymers or modified silicones. Undecylenic acid was first isolated from the products of distillation of castor oil in 1877 via pyrolysis of ricinoleic acid, and has been polymerized for vinyl production. It it suggested that many organic fatty acids exert fungicidal or fungistatic actions. Undecylenic acid also possesses antifungal properties, but is never used on its own for antifungal purposes. Salts of undecylenate are found in topical over-the-counter or mixture products as antifungal agents. Zinc undecylenate 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 its bifunctional properties, undecylenate is also used as a linking molecule to conjugate other biomolecules such as proteins. It serves as an acid moiety for anabolic steroid boldenone.

GHS Hazard Statements

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H412 (96.19%): Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

Properties:

Chemical and Physical Properties

Computed Properties

Property Name

Property Value

Molecular Weight

184.27 g/mol

XLogP3

3.9

Hydrogen Bond Donor Count

1

Hydrogen Bond Acceptor Count

2

Rotatable Bond Count

9

Exact Mass

184.146329876 g/mol

Monoisotopic Mass

184.146329876 g/mol

Topological Polar Surface Area

37.3Ų

Heavy Atom Count

13

Formal Charge

0

Complexity

141

Isotope Atom Count

0

Defined Atom Stereocenter Count

0

Undefined Atom Stereocenter Count

0

Defined Bond Stereocenter Count

0

Undefined Bond Stereocenter Count

0

Covalently-Bonded Unit Count

1

Compound Is Canonicalized

Yes

Physical Description

colourless to pale yellow liquid

Boiling Point

Decomposes at 275°C

Melting Point

24.5 °C

Density

0.910 - 0.917

Solubility 

insoluble in water; soluble in alcohol and ether

Source:PubChem

Source Species: Prosopis africana
Download SDF