Undecylic acid

Undecylic acid
Names
IUPAC name
Undecanoic acid
Other names
Hendecanoic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.604 Edit this at Wikidata
EC Number
  • 203-964-2
KEGG
UNII
  • InChI=1S/C11H22O2/c1-2-3-4-5-6-7-8-9-10-11(12)13/h2-10H2,1H3,(H,12,13) checkY
    Key: ZDPHROOEEOARMN-UHFFFAOYSA-N checkY
  • O=C(O)CCCCCCCCCC
Properties
C11H22O2
Molar mass 186.29 g/mol
Appearance Colourless crystals
Density 0.89 g/cm3
Melting point 28.6 °C (83.5 °F; 301.8 K)
Boiling point 284 °C (543 °F; 557 K)
Viscosity mPa·s
Structure
D
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Corrosive
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability (yellow): no hazard codeSpecial hazards (white): no code
3
2
Flash point 113 °C (235 °F; 386 K)
Related compounds
Related fatty acids
 Decanoic acid, Lauric acid
Related compounds
 Undecanol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkYX markN ?)

Undecylic acid (systematically named undecanoic acid) is a carboxylic acid with chemical formula CH3(CH2)9COOH. It is often used as an antifungal agent, to treat ringworm and athlete's foot, for example. Like decanoic acid, it has a distinctive, unpleasant odor.

It is a natural human metabolite, found in trace amounts in human breast milk and infant formulas.

Uses

Undecanoic acid is employed as a chemical intermediate used in producing synthetic lubricants, plasticizers, industrial coatings, and fragrance compounds.

It is often used as an antifungal agent, to treat ringworm and athlete's foot among others.

Its therapeutic efficacy was first recognized in the 1940s in treating superficial fungal diseases affecting military troops stationed in highly humid environments, such as Southeast Asia.

See also

References

  1. 1 2 Voicu, Raluca; Boukherroub, Rabah; Bartzoka, Vasiliki; Ward, Tim; Wojtyk, James T. C.; Wayner, Danial D. M. (2004-12-21). "Formation, characterization, and chemistry of undecanoic acid-terminated silicon surfaces: patterning and immobilization of DNA". Langmuir: The ACS Journal of Surfaces and Colloids. 20 (26): 11713–11720. doi:10.1021/la047886v. ISSN 0743-7463. PMID 15595802.
  2. ↑ "CAS 112-37-8: Undecanoic acid | CymitQuimica". cymitquimica.com.
  3. ↑ "10 Undecenoic Acid - an overview | ScienceDirect Topics".