Undecylenic acid
| |
| Names | |
|---|---|
| IUPAC name
Undec-10-enoic acid
| |
| Other names
10-Undecenoic acid
| |
| Identifiers | |
3D model (JSmol)
|
|
| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.003.605 |
| MeSH | Undecylenic+acid |
PubChem CID
|
|
| UNII | |
CompTox Dashboard (EPA)
|
|
| |
| |
| Properties | |
| C11H20O2 | |
| Molar mass | 184.279 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).
| |
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.[not verified in body] 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
| This section needs additional citations for verification. (July 2015) |
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][better source needed] [needs update] 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][non-primary source needed]
General commercial uses
| This section needs additional citations for verification. (July 2015) |
Undecylenic acid is a fine chemical,[citation needed] and is used in the manufacture of pharmaceuticals,[citation needed] and cosmetics,[citation needed] and as a musk in perfumery;[citation needed] manufactured products include antidandruff shampoos and antimicrobial powders.[3][verification needed]
Medicinal uses
| This section needs additional citations for verification. (July 2015) |
 |
FDA approval
Undecylenic acid is not approved by the U.S. FDA.[4][needs update]
Medicinal uses
 | The factual accuracy of part of this article is disputed. The dispute is about the fact that apart from the cited Cochrane study, all other information appearing is unverifiable and so suspect, even after removal of the most ludicrous of content appearing prior to 6 July 2015. (July 2015) |
Undecylenic acid is an active ingredient in medications for skin infections,[citation needed] and to relieve itching, burning, and irritation associated with skin problems.[citation needed] 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.[citation needed] When used for tinea cruris, it can result in extreme burning.[citation needed] In some case studies of tinae versicolor, pain and burning result from fungicide application.[citation needed]
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.[citation needed] 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.[citation needed] 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.[citation needed]
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][non-primary source needed]
References
- ^ Lemuel P. Ereaux & Gibson E. Craig (1949). "Undecylenic Acid in Psoriasis". Can. Med. Assoc. J. 61 (4): 361–364. PMC 1591667. PMID 18140580.[better source needed][needs update]
- ^ Das, G., Trivedi, R.K. & Vasishtha, A.K., 1989, "Heptaldehyde and undecylenic acid from castor oil," J. Am. Oil Chem. Soc., 66:938–941.[non-primary source needed]
- ^ "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.[verification needed]
- ^ a b "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.[needs update]
- ^ 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 [1], 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.
{{cite journal}}: CS1 maint: multiple names: authors list (link)[non-primary source needed]