レシチン (卵由来)

外観

白色〜うすい黄褐色又はだいだい色, 結晶性粉末又は塊

定義

本品は、リン酸(*)のコリンエステルにステアリン酸(*)、パルミチン酸(*)及びオレイン酸(*)からなるジグリセリドの混合物が結合した天然物である。参照表示名称：リン酸, ステアリン酸, パルミチン酸, オレイン酸

溶解性

メタノール,エタノール,ベンゼン,エーテル,石油エーテル,クロロホルムに可溶、アセトン, 酢酸エチルに不溶。水と安定な乳濁液をつくる。

解説

ホスファチジルコリン，1,2-diacyl-sn-glycerol 3-phosphorylcholine．レシチン(lecithin)ともいう．動物，植物，酵母，かび類に広く分布している代表的なグリセロリン脂質．ほ乳動物組織では，全リン脂質の50％ 近くを占め，生体膜の主要構成成分である．卵黄ではグリセロリン脂質の約70％ がホスファチジルコリンであり，残りの大部分がホスファチジルエタノールアミンである．生物体から抽出された全リン脂質混合物からアセトン不溶のリン脂質をとり，塩化カドミウムなどの金属塩との複合体の溶解度差を利用した精製法か，あるいはアルミナやシリカゲルのカラムクロマトグラフィーにより精製する．天然物はL-α-体で，白または微黄色の樹脂状あるいはろう状物質である．炭素数16～23の飽和あるいは不飽和脂肪酸を含むが，一般にグリセロールの1位に飽和脂肪酸，2位に不飽和脂肪酸が結合しているものが多い．不飽和脂肪酸の多い天然のものは，酸化を受けやすく不安定である．E. Baerらによる全合成法や酵素反応を利用した調製法も報告されている．メタノール，エタノール，ベンゼン，エーテル，石油エーテル，クロロホルムに可溶，アセトン，酢酸エチルに不溶．水溶液中に懸濁させると脂質二重膜の小胞を形成する．大豆からとったホスファチジルコリン(soya lecithin)などは，食用かつ消化しうる界面活性剤，食品や医薬品の乳化剤，高脂血症の治療薬として用いられている．生体内では，ジグリセリドとCDP-コリンの反応，またはホスファチジルエタノールアミンのメチル化により生合成される．

用途

界面活性剤。

用途

phospholipaseの酵素基質。レシチンを用いた各種研究用。

用途

生体膜や再構成の研究用。

化粧品の成分用途

皮膚コンディショニング剤、乳化剤

使用上の注意

不活性ガス封入

説明

Food-grade lecithin is obtained from soybeans and other plant sources. It is a complex mixture of acetone-insoluble phosphatides that consists chiefly of phosphatidyl choline, phosphatidyl etha nolamine, and phosphatidyl inositol, combined with various amounts of other substances such as triglycerides, fatty acids, and carbohydrates. Refined grades of lecithin may contain any of these components in varying proportions and combinations depending on the type of fractionation used. In its oil-free form, the prepon-derance of triglycerides and fatty acids is removed and the product contains 90% or more of phosphatides representing all or certain fractions of the total phosphatide complex. The consistency of both natural grades and refined grades of lecithin may vary from plastic to fluid, depending upon free fatty acid and oil content, and upon the presence or absence of other diluents. Its color varies from light yellow to brown, depending on the source, on crop variations, and on whether it is bleached or unbleached. It is odorless or has a characteristic, slight nutlike odor and a bland taste. Edible diluents, such as cocoa butter and vegetable oils, often replace soybean oil to improve functional and flavor characteris tics. Lecithin is only partially soluble in water, but it readily hydrates to form emulsions. The oil-free phosphatides are soluble in fatty acids, but are practically insoluble in fixed oils. When all phosphatide fractions are present, lecithin is partially soluble in alcohol and practically insoluble in acetone.

化学的特性

Lecithins vary greatly in their physical form, from viscous semiliquids to powders, depending upon the free fatty acid content. They may also vary in color from brown to light yellow, depending upon whether they are bleached or unbleached or on the degree of purity. When they are exposed to air, rapid oxidation occurs, also resulting in a dark yellow or brown color.
Lecithins have practically no odor. Those derived from vegetable sources have a bland or nutlike taste, similar to that of soybean oil.

天然物の起源

Lecithin is found in foods such as eggs, beef liver, and peanuts. Commercial sources are available

使用

lecithin (hydrogenated) is an emulsifier.

定義

ChEBI: A glycerophosphocholine compound having O-acyl substituents at both the 1- and 2-positions of the glycerol. It is a major constituent of cell membranes.

調製方法

Lecithins are essential components of cell membranes and, in principle, may be obtained from a wide variety of living matter. In practice, however, lecithins are usually obtained from vegetable products such as soybean, peanut, cottonseed, sunflower, rapeseed, corn, or groundnut oils. Soybean lecithin is the most commercially important vegetable lecithin. Lecithin obtained from eggs is also commercially important and was the first lecithin to be discovered.
Vegetable lecithins are obtained as a by-product in the vegetable oil refining process. Polar lipids are extracted with hexane and, after removal of the solvent, a crude vegetable oil is obtained. Lecithin is then removed from the crude oil by water extraction. Following drying, the lecithin may be further purified.
With egg lecithin, a different manufacturing process must be used since the lecithin in egg yolks is more tightly bound to proteins than in vegetable sources. Egg lecithin is thus obtained by solvent extraction from liquid egg yolks using acetone or from freeze-dried egg yolks using ethanol (95%).
Synthetic lecithins may also be produced.

応用例（製薬）

Lecithins are used in a wide variety of pharmaceutical applications. They are also used in cosmetics and food products.
Lecithins are mainly used in pharmaceutical products as dispersing, emulsifying, and stabilizing agents, and are included in intramuscular and intravenous injections, parenteral nutrition formulations, and topical products such as creams and ointments.
Lecithins are also used in suppository bases, to reduce the brittleness of suppositories, and have been investigated for their absorption-enhancing properties in an intranasal insulin formulation. Lecithins are also commonly used as a component of enteral and parenteral nutrition formulations.
There is evidence that phosphatidylcholine (a major component of lecithin) is important as a nutritional supplement to fetal and infant development. Furthermore, choline is a required component of FDA-approved infant formulas. Other studies have indicated that lecithin can protect against alcohol cirrhosis of the liver, lower serum cholesterol levels, and improve mental and physical performance.
Liposomes in which lecithin is included as a component of the bilayer have been used to encapsulate drug substances; their potential as novel delivery systems has been investigated. This application generally requires purified lecithins combined in specific proportions.
Therapeutically, lecithin and derivatives have been used as a pulmonary surfactant in the treatment of neonatal respiratory distress syndrome.

副作用

Lecithin may be safe when used as a supplement at a maximum dose of 30 grams per day for up to 6 weeks. It may have side effects, including diarrhoea, nausea, stomach pain or a feeling of fullness. When applied to the skin: Lecithin is probably safe for most adults. When used medicinally or as a drug carrier, no related serious adverse reactions have been reported.

安全性

Lecithin is a component of cell membranes and is therefore consumed as a normal part of the diet. Although excessive consumption may be harmful, it is highly biocompatible and oral doses of up to 80 g daily have been used therapeutically in the treatment of tardive dyskinesia. When used in topical formulations, lecithin is generally regarded as a nonirritant and nonsensitizing material. The Cosmetic Ingredients Review Expert Panel (CIR) has reviewed lecithin and issued a tentative report revising the safe concentration of the material from 1.95% to 15.0% in rinse-off and leave-in products. They note, however, that there are insufficient data to rule on products that are likely to be inhaled.

貯蔵

Lecithins decompose at extreme pH. They are also hygroscopic and subject to microbial degradation. When heated, lecithins oxidize, darken, and decompose. Temperatures of 160–180°C will cause degradation within 24 hours.
Fluid or waxy lecithin grades should be stored at room temperature or above; temperatures below 10°C may cause separation.
All lecithin grades should be stored in well-closed containers protected from light and oxidation. Purified solid lecithins should be stored in tightly closed containers at subfreezing temperatures.

純化方法

Lecithin from hen egg white is purified by solvent extraction and chromatography on alumina. It is suspended in H2O and kept frozen until required [Lee & Hunt J Am Chem Soc 106 7411 1984, Singleton et al. J Am Oil Chem Soc 42 53 1965]. For purification of commercial egg lecithin, see Pangborn [J Biol Chem 188 471 1951].

不和合性

Incompatible with esterases owing to hydrolysis.

規制状況(Regulatory Status)

GRAS listed. Accepted for use as a food additive in Europe. Included in the FDA Inactive Ingredients Database (inhalations; IM and IV injections; otic preparations; oral capsules, suspensions and tablets; rectal, topical, and vaginal preparations). Included in nonparenteral and parenteral medicines licensed in the UK. Included in the Canadian List of Acceptable Non-medicinal Ingredients.