Undecylenic acid

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Undecylenic acid
Undecylenic acid.png
Names
IUPAC name
Undec-10-enoic acid
Other names
10-Undecenoic acid
Identifiers
112-38-9 YesY
ChEBI CHEBI:35045 YesY
ChemSpider 10771160 YesY
Jmol 3D model Interactive image
MeSH Undecylenic+acid
PubChem 5634
UNII K3D86KJ24Nk N
  • InChI=1S/C11H20O2/c1-2-3-4-5-6-7-8-9-10-11(12)13/h2H,1,3-10H2,(H,12,13) YesY
    Key: FRPZMMHWLSIFAZ-UHFFFAOYSA-N YesY
  • 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
  • C=CCCCCCCCCC(=O)O
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
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 YesYN ?)
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.[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 an topical antifungal agent.

Structure and properties

Lua error in package.lua at line 80: module 'strict' not found. 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][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

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

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FDA approval

Undecylenic acid is not approved by the U.S. FDA.[4][needs update]

Medicinal uses

Lua error in package.lua at line 80: module 'strict' not found. 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 presecription 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

  1. ↑ Lua error in package.lua at line 80: module 'strict' not found.[better source needed][needs update]
  2. ↑ 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]
  3. ↑ Lua error in package.lua at line 80: module 'strict' not found. - see page 2 of link.[verification needed]
  4. ↑ 4.0 4.1 Lua error in package.lua at line 80: module 'strict' not found.[needs update]
  5. ↑ 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.
  6. ↑ Lua error in package.lua at line 80: module 'strict' not found.[non-primary source needed]
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