Undecylenic acid
 | |
| Names | |
|---|---|
| IUPAC name
Undec-10-enoic acid | |
| Other names
10-Undecenoic acid | |
| Identifiers | |
112-38-9  | |
| ChEBI | CHEBI:35045 |
| ChemSpider | 10771160 |
| Jmol 3D model | Interactive image |
| MeSH | Undecylenic+acid |
| PubChem | 5634 |
| UNII | K3D86KJ24Nk  |
| |
| |
| Properties | |
| 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 | |
| D01AE04 (WHO) | |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| verify (what is ?) | |
| 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 a 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.[1] 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. [2]
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.[3]
Medicinal uses
FDA approval
Undecylenic acid is not approved by the U.S. FDA.[4]
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,[4] 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 prescription azoles (e.g., clotrimazole) and allylamines (e.g., terbinafine), though there were not "sufficient comparative trials to judge relative efficacy."[5]
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).[6]
References
- ↑ Lemuel P. Ereaux & Gibson E. Craig (1949). "Undecylenic Acid in Psoriasis". Can. Med. Assoc. J. 61 (4): 361–364. PMC: 1591667. PMID 18140580.
- ↑ Das, G., Trivedi, R.K. & Vasishtha, A.K., 1989, "Heptaldehyde and undecylenic acid from castor oil," J. Am. Oil Chem. Soc., 66:938–941.
- ↑ "United States International Trade Commission Memorandum" (PDF). USITC. Archived from the original (PDF) on 2006-09-24. Retrieved 2007-01-02. - see page 2 of link.
- 1 2 "Ingredient List P-Z" (PDF). FDA (see page 65 of this link). Archived from the original (PDF) on 2006-10-16. Retrieved 2006-12-28.
- ↑ Crawford F., Hart R., Bell-Syer S., Torgerson D., Young P. & Russell I., 2000, "Topical treatments for fungal infections of the skin and nails of the foot," Cochrane Database Syst Rev. 2000(2):CD001434, see , accessed 6 July 2015.
- ↑ A. Moraillon, A. C. Gouget-Laemmel, F. Ozanam, and J.-N. Chazalviel (2008). "Amidation of Monolayers on Silicon in Physiological Buffers: A Quantitative IR Study". J. Phys. Chem. C 112 (18): 7158–7167. doi:10.1021/jp7119922.