Undecylenic acid

Undecylenic acid

Names
IUPAC name Undec-10-enoic acid
Other names 10-Undecenoic acid
Identifiers
CAS Number	112-38-9 Y
ChEBI	CHEBI:35045 Y
ChemSpider	10771160 Y
Jmol 3D model	Interactive image
MeSH	Undecylenic+acid
PubChem	5634
UNII	K3D86KJ24Nk N
InChI InChI=1S/C11H20O2/c1-2-3-4-5-6-7-8-9-10-11(12)13/h2H,1,3-10H2,(H,12,13) Y Key: FRPZMMHWLSIFAZ-UHFFFAOYSA-N Y InChI=1/C11H20O2/c1-2-3-4-5-6-7-8-9-10-11(12)13/h2H,1,3-10H2,(H,12,13) Key: FRPZMMHWLSIFAZ-UHFFFAOYAJ
SMILES C=CCCCCCCCCC(=O)O
Properties
Chemical formula	C11H20O2
Molar mass	184.28 g·mol−1
Density	0.912 g/mL
Melting point	23 °C (73 °F; 296 K)
Boiling point	275 °C (527 °F; 548 K)
Pharmacology
ATC code	D01AE04
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Undecylenic acid is a synthetic unsaturated fatty acid. It is prepared from the natural product, ricinoleic acid, present in castor oil. Undecylenic acid is produced by cracking castor oil at high temperature and pressure. It is the common name of 10-undecenoic acid, abbreviated (CH₂=CH(CH₂)₈COOH), and has two functional groups, a terminal alkene at one end, and a carboxylic acid at the other. It has use in synthetic chemistry and is used in the manufacture of pharmaceuticals, personal hygiene products, cosmetics, and perfumes. It also used as an topical antifungal agent.

Structure and properties

Undecylenic acid is an organic compound, an unsaturated fatty acid. It is the common name of 10-undecenoic acid, (CH₂=CH(CH₂)₈COOH).

Preparation

It is prepared as a pyrolysis product of ricinoleic acid derived from castor oil; specifically, undecylenic acid is produced by the chemical process termed cracking, on naturally derived castor oil, under pressure. Ricinoleic acid is converted during this manufacturing process into the title compound, and heptaldehyde; McLafferty rearrangement, free-radical, and other mechanisms have been proposed for the transformation.

General commercial uses

Undecylenic acid is a fine chemical, and is used in the manufacture of pharmaceuticals, and cosmetics, and as a musk in perfumery; manufactured products include antidandruff shampoos and antimicrobial powders.

Medicinal uses

FDA approval

Undecylenic acid is not approved by the U.S. FDA.

Medicinal uses

Undecylenic acid is an active ingredient in medications for skin infections, and to relieve itching, burning, and irritation associated with skin problems. For example, it is used against fungal skin infections, such as athlete's foot, ringworm, tinea cruris, or other generalized infections by Candida albicans. When used for tinea cruris, it can result in extreme burning. In some case studies of tinae versicolor, pain and burning result from fungicide application.

In an older review of placebo-controlled trials, undecenoic acid was deemed efficacious, alongside presecription azoles (e.g., clotrimazole) and allylamines (e.g., terbinafine), though there were not "sufficient comparative trials to judge relative efficacy."

One of mechanisms underlying its antifungal effects against Candida albicans is its inhibition of morphogenesis. In a study on denture liners, undecylenic acid in the liners was found to inhibit conversion of yeast to the hyphal form (which are associated with active infection), via inhibition of fatty acid biosynthesis. The mechanism of action and effectiveness in fatty acid-type antifungals is dependent on the number of carbon atoms in the chain, with efficacy increasing with the number of atoms in the chain.

Research uses

Undecylenic acid has been used as a linking molecule, because it is a bifunctional compound, in this case, an α,ω- (terminally functionalized) bifunctional agent. For instance, the title compound has been used to prepare silicon-based biosensors, linking silicon transducer surfaces to the terminal double bond of undecylenic acid (forming an Si-C bond), leaving the carboxylic acid groups available for conjugation of biomolecules (e.g., proteins).