General Description
White solid with a slight odor of bay oil.
Reactivity Profile
LAURIC ACID(143-07-7) is a carboxylic acid. Carboxylic acids donate hydrogen ions if a base is present to accept them. They react in this way with all bases, both organic (for example, the amines) and inorganic. Their reactions with bases, called "neutralizations", are accompanied by the evolution of substantial amounts of heat. Neutralization between an acid and a base produces water plus a salt. Carboxylic acids in aqueous solution and liquid or molten carboxylic acids can react with active metals to form gaseous hydrogen and a metal salt. Such reactions occur in principle for solid carboxylic acids as well, but are slow if the solid acid remains dry. Even "insoluble" carboxylic acids may absorb enough water from the air and dissolve sufficiently in LAURIC ACID(143-07-7) to corrode or dissolve iron, steel, and aluminum parts and containers. Carboxylic acids, like other acids, react with cyanide salts to generate gaseous hydrogen cyanide. The reaction is slower for dry, solid carboxylic acids. Insoluble carboxylic acids react with solutions of cyanides to cause the release of gaseous hydrogen cyanide. Flammable and/or toxic gases and heat are generated by the reaction of carboxylic acids with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. Carboxylic acids, especially in aqueous solution, also react with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat. Their reaction with carbonates and bicarbonates generates a harmless gas (carbon dioxide) but still heat. Like other organic compounds, carboxylic acids can be oxidized by strong oxidizing agents and reduced by strong reducing agents. These reactions generate heat. A wide variety of products is possible. Like other acids, carboxylic acids may initiate polymerization reactions; like other acids, they often catalyze (increase the rate of) chemical reactions. This compound can react with oxidizing materials.
Air & Water Reactions
Insoluble in water.
Health Hazard
May be harmful by inhalation, ingestion or skin absorption. Vapor or mist is irritating to eyes, mucous membrane and upper respiratory tract. Causes eye and skin irritation.
Fire Hazard
Behavior in Fire: May cause dust explosion.
Description
Lauric acid (143-07-7), the saturated fatty acid with a 12-carbon atom chain, thus falling into the medium chain fatty acids, is a white, powdery solid with a faint odor of bay oil or soap.
Physical properties
Lauric acid occurs as a white crystalline powder with a slight odor of bay oil or a fatty odor. It is a common constituent of most diets; large doses may produce gastrointestinal upset.
Occurrence
Lauric acid, as a component of triglycerides, comprises about half of the fatty acid content in coconut oil, laurel oil, and in palm kernel oil (not to be confused with palm oil) , Otherwise it is relatively uncommon. It is also found in human breast milk ( 6.2 % of total fat), cow's milk (2.9%), and goat's milk (3.1 %).
Definition
ChEBI: A straight-chain, twelve-carbon medium-chain saturated fatty acid with strong bactericidal properties; the main fatty acid in coconut oil and palm kernel oil.
Aroma threshold values
Aroma characteristics at 1.0%: fatty, creamy, cheeselike, candle waxy with egglike richness
Taste threshold values
Taste characteristics at 5 ppm: waxy,fatty and oily, tallowlike, creamy and dairylike with a coating mouthfeel
Pharmaceutical Applications
pharmaceutical applications it has also been examined for use as an
enhancer for topical penetration and transdermal absorption,
rectal absorption, buccal delivery,(14) and intestinal absorption.
It is also useful for stabilizing oil-in-water emulsions.
Lauric acid has also been evaluated for use in aerosol formulations.
Biochem/physiol Actions
Substrate for CYP 4A11
Safety
Lauric acid is widely used in cosmetic preparations, in the
manufacture of food-grade additives, and in pharmaceutical
formulations. General exposure to lauric acid occurs through the
consumption of food and through dermal contact with cosmetics,
soaps, and detergent products. Lauric acid is toxic when
administered intravenously.
Occupational exposure may cause local irritation of eyes, nose,
throat, and respiratory tract, although lauric acid is considered
safe and nonirritating for use in cosmetics. No toxicological
effects were observed when lauric acid was administered to rats at
35% of the diet for 2 years. Acute exposure tests in rabbits
indicate mild irritation. After subcutaneous injection into mice,
lauric acid was shown to be noncarcinogenic.
LD50 (mouse, IV): 0.13 g/kg
LD50 (rat, oral): 12 g/kg
Synthesis
Produced from synthetic lauryl alcohol
in vitro
previous study showed that lauric acid could induce apoptosis in both caco-2 and iec-6 cells when compared to butyrate. moreover, lauric acid reduced gsh availability and generated ros in caco-2 cells. mechanistic study indicated that lauric acid reduced caco-2 and iec-6 cells in g0/g1and arrested cells in the s and g2/m phases. in addition, it was found that butyrate protected iec-6 cells from ros-induced damage, while lauric acid induced higher levels of ros when compared with butyrate [1].
in vivo
mouse in vivo study found that both epicutaneous application and intradermal injection of lauric acid could decrease the number of p. acnes colonized in mouse ears effectively, thus relieving p. acnes-induced granulomatous inflammation and ear swelling [2].
Carcinogenicity
Lauric acid was not carcinogenic
in the BALB/c:CFW mouse after repeated subcutaneous
injections. Lauric acid applied twice weekly for 20
weeks did not promote tumors in mice initiated with 9,10-
dimethyl-1,2-benzanthracene. After more extended
application (daily, 6 days/week, for 31 weeks), lauric acid
caused an increase in skin papillomas, but no histologically
malignant tumors were found. Lauric acid was not
carcinogenic in rats after exposure in the diet to 35% lauric
acid for 2 years.
storage
Lauric acid is stable at normal temperatures and should be stored in
a cool, dry place. Avoid sources of ignition and contact with
incompatible materials.
Purification Methods
Distil the acid in a vacuum. Also crystallise it from absolute EtOH, or from acetone at -25o. Alternatively, purify it via its methyl ester (b 140.0o/15mm), as described for capric acid. It has also been purified by zone melting. [cf Beilstein 1 III 2913.]
Incompatibilities
Lauric acid is incompatible with strong bases, reducing agents, and
oxidizing agents.
Regulatory Status
GRAS listed. Lauric acid is listed as a food additive in the EAFUS list
compiled by the FDA. Reported in the EPA TSCA Inventory.
References
[1] fauser jk,matthews gm,cummins ag,howarth gs. induction of apoptosis by the medium-chain length fatty acid lauric acid in colon cancer cells due to induction of oxidative stress. chemotherapy.2013;59(3):214-24.
[2] nakatsuji t,kao mc,fang jy,zouboulis cc,zhang l,gallo rl,huang cm. antimicrobial property of lauric acid against propionibacterium acnes: its therapeutic potential for inflammatory acne vulgaris. j invest dermatol.2009 oct;129(10):2480-8.
[3] kate l. feltrin et al. acute oral administration of lauric acid reduces energy intake in healthy males. e-spen journal. 2014 april; 9 (2): e69–e75