Description
Hendecanoic acid (also known as undecanoic acid, undecylenic acid and undecylic acid) is a naturally occurring carboxylic acid. Its chemical formula is CH3(CH2)9COOH. It may participate in the control of triacylglycerol synthesis, and is found in breast milk and infant formula. It is known as an antifungal agent, used for the treatment of some types of fungal infections including ringworm and athlete’s foot. One of its mechanism of action is through inhibition of the morphogenesis of Candida albicans. It may also interfere with the fatty acid biosynthesis process of fungi. It is manufactured by the vacuum distillation of castor bean oil through the pyrolysis of ricinoleic acid. However, it has been generally replaced by new generation of anti-fungal medicine.
References
http://www.altmedrev.com/publications/7/1/68.pdf
https://pubchem.ncbi.nlm.nih.gov/compound/undecanoic_acid#section=Top
http://www.mayoclinic.org/drugs-supplements/undecylenic-acid-topical-route/description/drg-20066601
https://en.wikipedia.org/wiki/Undecylic_acid
Description
Undecanoic acid is a saturated fatty acid containing eleven carbons (C11:0). It is cytotoxic to certain filamentous fungi and is used to study fungal mechanisms of resistance. Undecanoic acid is also used to acylate larger molecules.
Chemical Properties
Undecanoic acid has a faint fatty, aldehydic odor.
Chemical Properties
white to pale yellowish low melting solid
Occurrence
Occurs naturally in butter and in the oil of Artemisisa frigida Willd.; also reported found in the oils of
Chamaecyparis pisifera Engl., wild thyme, Thymus marschollianus and coconut. Also reported found in apple, banana, sour cherry,
lemon and mandarin peel oil, grapefruit juice, guava, grapes, papaya, many cheeses, milk powder, chicken and beef fat, cooked mutton,
cured pork, beer, cognac, rum, whiskies, white wine, tea, coconut milk, beans, licorice, mango, mushrooms, rice, sake, wort,
loquat, scallop and maté.
Uses
Undecanoic Acid is a saturated fatty acid. It may be used to activate orphan G protein-coupled receptor GPR40.
Uses
Undecanoic acid was used in the formation of cycloamylose crystals.
Uses
Intermediates of Liquid Crystals
Preparation
Hendecanoic acid can be produced by reduction of Undecylenic acid,
which is generally obtained from Castor oil.
Definition
ChEBI: A straight-chain, eleven-carbon saturated medium-chain fatty acid found in body fluids; the most fungitoxic of the C7:0 - C18:0 fatty acid series.
Aroma threshold values
Detection: 10 ppb
Taste threshold values
Taste characteristics at 20 ppm: waxy, creamy, cheese-like with a fatty dairy mouthfeel.
General Description
White crystalline solid. Insoluble in water. Specific gravity 0.85. Hence floats on water.
Air & Water Reactions
Dust explosion is possible. [USCG, 1999]. Insoluble in water.
Reactivity Profile
A weak carboxylic acid. Neutralizes bases with the evolution of substantial amounts of heat to produce water plus a salt. Reacts with solutions of cyanides to cause the release of gaseous hydrogen cyanide. Can generate flammable and/or toxic gases and heat by reaction with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. Reacts in with aqueous solutions of nitrites and thiosulfates (to give H2S and SO3) and dithionites (to give SO2) and heat. Reaction with solutions of carbonates and bicarbonates generate a harmless gas (carbon dioxide) but still heat. Can be oxidized by strong oxidizing agents and reduced by strong reducing agents. These reactions generate heat. May initiate polymerization reactions. May serve as a catalyst.
Health Hazard
May be harmful by inhalation, ingestion or skin absorption. Material is irritating to mucous membrane and upper respiratory tract. Causes eye and skin irritation.
Fire Hazard
Special Hazards of Combustion Products: Dust explosion is possible.
References
[1] ANA GRACI BRITO-MADURRO. Undecanoic acid resistance in filamentous fungi: identification and linkage mapping of the Aspergillus nidulans udaA gene.[J]. Journal of General and Applied Microbiology, 2005, 51 1: 47-49. DOI:
10.2323/jgam.51.47[2] FERNANDA G PAIO. Analysis of Trichophyton rubrum gene expression in response to cytotoxic drugs.[J]. Fems Microbiology Letters, 2007, 271 2: 180-186. DOI:
10.1111/j.1574-6968.2007.00710.x[3] ELENA BOGATCHEVA. Chemical modification of capuramycins to enhance antibacterial activity.[J]. Journal of Antimicrobial Chemotherapy, 2011, 66 3: 578-587. DOI:
10.1093/jac/dkq495
