КИСЛОТА лауриновая

Описание

Lauric acid, also known as dodecanoic acid, is a saturated fatty acid with a 12-carbon atom chain, thus falling into the medium chain fatty acids, is a white crystalline carboxylic acid with a faint odor of bay oil or soap. It has been found at high levels in coconut oil. Lauric acid induces the activation of NF-κB and the expression of COX-2, inducible nitric oxide synthase (iNOS), and IL-1α in RAW 264.7 cells when used at a concentration of 25 μM.

Физические свойства

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.

Химические свойства

Like many other fatty acids, lauric acid is inexpensive, has a long shelf-life, and is non-toxic and safe to handle. It is mainly used for the production of soaps and cosmetics. For these purposes, lauric acid is neutralized with sodium hydroxide to give sodium laurate, which is a soap. Most commonly, sodium laurate is obtained by saponification of various oils, such as coconut oil. These precursors give mixtures of sodium laurate and other soaps.

Вхождение

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 %).

Использование

Given its foaming properties, the derivatives of lauric acid (h-dodecanoic acid) are widely used as a base in the manufacture of soaps, detergents, and lauryl alcohol. Lauric acid is a common constituent of vegetable fats, especially coconut oil and laurel oil. It may have a synergistic effect in a formula to help fight against mircoorganisms. It is a mild irritant but not a sensitizer, and some sources cite it as comedogenic.

Определение

ChEBI: Lauric acid is 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. It has a role as a plant metabolite, an antibacterial agent and an algal metabolite. It is a straight-chain saturated fatty acid and a medium-chain fatty acid. It is a conjugate acid of a dodecanoate. It derives from a hydride of a dodecane.

Методы производства

Lauric acid is a fatty carboxylic acid isolated from vegetable and animal fats or oils. For example, coconut oil and palm kernel oil both contain high proportions of lauric acid. Isolation from natural fats and oils involves hydrolysis, separation of the fatty acids, hydrogenation to convert unsaturated fatty acids to saturated acids, and finally distillation of the specific fatty acid of interest.

Общее описание

White solid with a slight odor of bay oil.

Реакции воздуха и воды

Insoluble in water.

Угроза здоровью

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.

Пожароопасность

Behavior in Fire: May cause dust explosion.

Фармацевтические приложения

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.

Безопасность

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

Канцерогенность

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.

хранилище

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.

Методы очистки

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.]

Несовместимости

Lauric acid is incompatible with strong bases, reducing agents, and oxidizing agents.

Регуляторный статус

GRAS listed. Lauric acid is listed as a food additive in the EAFUS list compiled by the FDA. Reported in the EPA TSCA Inventory.