Name | Lecithins |
Synonyms | SPC Lecithin Lecithins LECITHIN POWDER LECITHIN,GRANULAR,NF LECITHIN,GRANULAR,FCC LECITHIN,ENZYME-MODIFIED Polyene phosphatidylcholine L-Alpha-Phosphatidyl Choline Polyene Phosphatidyl choline l-α-phosphatidylcholine solution PHOSPHATIDYLCHOLINE(LECITHIN)(RG) l-α-phosphatidylcholine, hydrogenated [(2R)-2,3-diacetoxypropoxy]-(2-trimethylammonioethyl)phosphinate |
CAS | 8002-43-5 |
EINECS | 232-307-2 |
InChI | InChI=1/C12H24NO7P/c1-10(14)18-8-12(20-11(2)15)9-19-21(16,17)7-6-13(3,4)5/h12H,6-9H2,1-5H3/t12-/m1/s1 |
InChIKey | FWMYJLDHIVCJCT-VSZGHEPYSA-N |
Molecular Formula | C42H80NO8P |
Molar Mass | 758.06 |
Density | d424 1.0305 |
Melting Point | >145°C (dec.) |
Flash Point | 57°C |
Water Solubility | NEGLIGIBLE |
Solubility | chloroform: 0.1g/mL, slightly hazy, slightly yellow to deep orange |
Appearance | solution |
Color | Pale Brown to Yellow |
Merck | 14,5429 |
BRN | 5209585 |
Storage Condition | -20°C |
Stability | Stable, but light, heat, moisture and air-sensitive. Incompatible with strong oxidizing agents. |
Physical and Chemical Properties | Lecithin has broad and narrow sense, narrow sense of lecithin refers to phosphatidylcholine, broadly refers to PC, PE, PI (phosphatidylinositol, phosphatidyl inositol), PS (serine phospholipids, phosphatidyl serines), including phospholipids. Phosphatidylcholine in the brain, nerve tissue, liver, adrenal gland and red blood cell content is more, the content of egg yolk (about 8%-10%), so called lecithin. Lecithin has two kinds of isomers, α and β, depending on the position where phosphoric acid is attached to glycerol. Lecithin in nature is α-type. Almost saturated fatty acids are attached at the carbon position, while unsaturated fatty acids such as oleic acid, linoleic acid, linolenic acid and arachidonic acid are usually attached at the β position. The nitrogen-containing organic base in lecithin in combination with phosphoric acid is choline. In the lecithin molecule, the β carbon atom of the glycerol moiety is a chiral carbon atom, and thus there are both D-type and L-type configurations. Naturally occurring is the L-type. This product is composed of several parts of phospholipid molecules, unsaturated fatty acids, choline and inositol. Pure lecithin is a water-absorbing white wax that changes to a yellow or brown translucent waxy mass in the air due to oxidation of unsaturated fatty acids. The acetone precipitation of lecithin in granular or powder. Soluble in petroleum ether, chloroform, ether, benzene and ethanol, insoluble in acetone, insoluble in water. It is hygroscopic, easy to oxidize, and gradually darkened in air. Lecithin is hydrolyzed in the human body to glycerol, unsaturated fatty acids, choline and phosphoric acid, in which the phosphate group is hydrophilic and the fatty acid group is lipophilic. These two groups make lecithin emulsifiable. The physiological role of lecithin: the main component of the cell membrane, can promote the cell to absorb nutrients to eliminate toxic waste. It can assist the absorption of fat-soluble vitamins A, D, E and K and increase the utilization rate of these vitamins by 100%. Supplementing enough lecithin can enhance the vitality of cells, enhance the immunity and disease resistance of human body. Powerful emulsifier, it can make the blood cholesterol and neutral fat into very small particles, in order to facilitate the absorption and metabolism of tissues, thereby preventing the deposition of cholesterol in blood vessels, prevent cholesterol deposition caused by atherosclerosis, high blood pressure and heart disease. More typically compatible molecules, involved in the composition of various lipoproteins. It is an indispensable substance for the catalysis of various lipid-dependent enzymes. It is related to the mechanism of action of hormones. It plays an important role in the transmission of nerve excitation. Sun runguang et al. studied lecithin-porphyrin metal complexes (Now called complex coordination compounds, referred to as complexes) conductivity. The results show that: when the general electrode and lecithin-porphyrin metal complexes (such as Ni porphyrin, Mg porphyrin) electrode composed of the primary battery, the electromotive force is 1-2 times of the general electrode composed of the electromotive force of the primary battery. Small angle X-ray scattering (SAXS) method was used to study the structural changes of lecithin-porphyrin metal complexes, when the electrodes are made of chloroform and secondary distilled water in different proportions, the molecules of the porphyrin metal complexes interact with the lecithin molecules, so that the porphyrin metal complexes are embedded between the lecithin molecules, A substance in the liquid crystal state is formed. These liquid crystalline substances are coated on the surface of the electrode to form a liquid crystalline film layer, which has a high order. Due to the existence of the liquid crystal film, the potential of the original conductive glass and the conductive liquid is changed, which is beneficial to the electron transfer of the porphyrin metal complex, and the conductivity of the lecithin-porphyrin metal complex electrode is increased, thus, the electrode potential is changed, and the electromotive force is significantly improved compared with the electromotive force generated by the conductive glass electrode which is not coated with such a liquid crystal substance. |
Use | Used as health food raw materials, emulsifier, quality improver Raw materials of emulsifier and Liposome for injection |
WGK Germany | 3 |
RTECS | OG7565000 |
FLUKA BRAND F CODES | 1-8-10 |
TSCA | Yes |
HS Code | 29239000 |
Toxicity | LD50 oral in rat: > 8mL/kg |
shade, hermetically sealed, stored in a cool and dry place.
EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
The third nutrient | lecithin, also known as phosphatidylcholine, is composed of glycerol, fatty acids (two molecules), phosphoric acid and choline water loss condensation of lipid, the fatty acid chain in the molecule is saturated and unsaturated two, non-polar hydrophobic tail; Phosphate choline part is a dipole ion, is a polar hydrophilic head, known as protein, vitamin after the "third nutrient". It is the material basis of life, is the basic raw material of cell membrane structure, exists in every cell, more concentrated in the liver, brain, heart, kidney and immune system, synthesized by the liver in the human body, food mainly exists in soybean, egg yolk. Lecithin in English means "egg yolk". Lecithin is an important anti-aging material, and protein interaction, the formation of lipoprotein, not only can improve the quality of food, but also improve the cardiovascular and cerebrovascular and nervous system function of health care. It can regulate blood lipids to prevent vascular sclerosis, protect the liver, prevent Alzheimer's disease, brain intelligence, prevent and dissolve the formation of gallstones, improve the activity of cell superoxide dismutase (SOD), strengthen the ability of cells to scavenge free radicals, Reduce the production of lipid peroxide, and can separate and disintegrate endotoxin, because of its hydrophilicity, can enhance the function of hemoglobin to make the skin smooth and soft, the inositol contained in it is the basic element of skin and hair health care, can promote blood circulation, promote hair regeneration, inhibit hair whitening, worthy of anti-aging guard. |
stability and storage conditions | lecithin is the trade name or common name of a naturally occurring mixture of phospholipids, is a natural Amphoteric Surfactant, it is widely distributed in animals and plants, can be found in all biological organisms, especially in egg yolk, soybean, peanut, rapeseed oil, sunflower, corn, milk, animal viscera, brain, bone marrow, muscle and blood. However, the largest industrial source of lecithin is the most important by-product in the production of refined soybean oil, commonly known as soybean phospholipid, which is the most widely used plant lecithin in commerce. Usually, a small amount of water is added to the crude soybean oil, the crude phospholipid was prepared by heating, stirring, centrifugation, and vacuum drying. Commercial lecithins typically contain about 40% of soybean oil. Extraction from egg yolk called egg yolk phospholipid, because the price is more expensive, limited to the use of medicine. The physical state of lecithin varies from a viscous semi-solid to a powder state, depending primarily on the content of free fatty acids. The color varies from brown to bright yellow, depending on whether bleached and purified. Oxidation, discoloration, degradation when heated; Degradation at 160~180 deg C for 24 hours; Degradation at extreme pH value, at the same time with hygroscopicity and microbial degradation. Liquid or waxy lecithin degrades at room temperature or above, and separation occurs below 10 °c. Store in a closed container, protected from light and oxygen; Purified lecithin should be stored in a closed container below freezing point. Soluble in aliphatic hydrocarbons, aromatic hydrocarbons, halogenated hydrocarbons, mineral oils and fatty acids, insoluble in cold vegetable oils, animal oils, polar solvents and water. |
appropriate population | 1, the U. S. Food and Drug Administration (FDA) regulations: in infant formula, must add phospholipids. 2, students, intellectuals and the elderly: lecithin can enhance brain vitality, eliminate brain fatigue, enhance memory, improve learning efficiency. And can repair the damaged brain cells, prevent the occurrence of senile dementia. 3, long-term drinking, nutrition excess and fatty liver patients: Daily taking 10-15 grams of lecithin, 3-5 months later, blood lipid indicators can return to normal levels. 4, diabetic patients: Daily consumption of more than 20 grams of soybean lecithin, the recovery rate of diabetic patients is quite obvious, many patients do not need to inject insulin. Diabetic gangrene and arteriosclerosis and other complications of patients, more effective. 5, gallstone patients: every day to take soy lecithin, not only to prevent the formation of gallstones, but also to varying degrees of decomposition, eliminate the formation of gallstones. 6, beauty of the woman: lecithin is a natural antidote, can break down the body's toxins. By increasing heme, the skin is provided with sufficient water, oxygen and other nutrients, so that the skin becomes smooth and soft 7. Constipation: lecithin can promote gastrointestinal blood circulation and gastrointestinal peristalsis, helps prevent and improve constipation. 8. Smokers should take more lecithin. The content of lecithin in the lungs of smokers is only 1/7 of that of non-smokers. Lecithin is very hydrophilic, Can keep the alveoli moist, so as to improve the body's oxygen intake. Smokers generally dry alveoli, oxygen intake is insufficient, so should add lecithin. 9, children, non-obese pregnant mothers or elderly people with weak body, lecithin and milk, soy milk and juice can be taken at the same time to supplement nutrition. Daily intake of 800~1000 mg. |
identification test | The soluble portion is soluble in water, but readily hydrates to form opacities. Deoiled phospholipids are soluble in fatty acids, but practically insoluble in volatile oils. Phosphorus sample 1G, add anhydrous sodium carbonate 2G, together with ignition. After cooling, the residue was dissolved in a mixture of 5ml of water and 5ml of nitric acid. Add ammonium molybdate solution (TS-22) after 5ml heating to boiling, yellow precipitation should occur. Choline was added to 0.5g of sample with 5ml of 1:1 dilute hydrochloric acid, heated in a water bath for 2H, and filtered. 10 μl of the filtrate was used as a sample solution for paper chromatography, a 1:200 aqueous solution of choline chloride was used as a control solution, and a mixed solution of n-butanol: Water: Acetic acid (4:2:1) was used as a developing solvent. When the developing solvent rises to about 25cm, it is air-dried, sprayed with I) ragendorff reagent for color development, and observed after one day and night, red-orange mottling similar to that of the control should appear. Fatty acid take sample 1G and 0.5mol/L potassium hydroxide ethanol solution 25ml, reflux together 1H, when cooled to ℃, should have potassium soap precipitation. Hydrolysis test 500ml of water at 30-35 °c was placed in an 800ml beaker, and then 50ml of sample was slowly added with constant stirring. Where hydrolyzed lecithin will form a homogeneous emulsion, while the non-hydrolyzed lecithin will form a special substance weighing 50g. The content analysis was the same as "10016, lecithin". |
content analysis | a sample of phospholipids was purified. About 10g of the sample was washed three times with of acetone each time. Take 5g of insoluble residue, dissolve in 10ml of petroleum ether, add 25ml of acetone, divide the precipitate into two equal parts, put it into two 40ml centrifuge tubes, dilute it to 40ml with acetone after fully stirring, then stirred, cooled in an ice bath for 15min, and then stirred and centrifuged for 5min. The acetone was decanted, stirred, cooled, centrifuged and the acetone decanted. The solid after the second centrifugation can be used to prepare the phospholipid-acetone solution. 5G purified phospholipids, about saturated 16L acetone. The remainder was determined by the method of "acetone insoluble matter" in "10011, hydroxylated lecithin. However, B in the final calculation is the percentage of toluene insolubles in the following quality index analysis. |
toxicity | LD50 oral in rat: > 8mL/kg LD50 oral in rat: > 8mL/kg |
usage limit | GB 2760-96: hydrogenated vegetable oil, cake, candy, gum gum base, all limited to G.MP. FAO/WHO(1984,g/kg): Margarine, meat soup (according to GMP); Shannon cheese 5 (according to the emulsion mixture, alone or with other stabilizers, carrier dosage); Instant milk powder, instant cream powder, formulated baby food, canned baby food, 5; Chocolate and sandwich chocolate 5~10 (lecithin insoluble in acetone, depending on the type of chocolate, total emulsifier 15); Cocoa powder and sugar-containing cocoa powder, cocoa liquor, cocoa oil cake, 10 (lecithin component insoluble in acetone, total emulsifier 15); cream 5 (alone or in combination with other thickeners and modifiers, only for pasteurized cream or UHT cream and Disinfection cream for puffs), grain-based processed foods for children 15 (dry basis). According to Japanese regulations, as an emulsifier can be used for margarine, shortening, accounting for 0.1% ~ 0.5% of the total fat content; Chocolate, milk fat sugar (to give the product gloss, improve chewing feeling, prevent hair, reduce the viscosity of chocolate refining in order to facilitate the production, cut, chocolate dosage 0.3% ~ 0.5%, milk fat sugar dosage 0.2% ~ 0.5%); Bread, biscuits, cake 0.2% ~ 0.5% (mixed with oil and shortening, to prevent aging and antioxidant effect); Noodles, Tongxin (add wheat flour 0.3% ~ 0.5%, can enhance the toughness of the product, even after cooking will not extend deformation); Ice Cream 0.5% (improve taste, prevent lactose crystallization); Soy sauce (added at the time of Koji, can enhance the enzyme power, Improve quality). It can be used as an impregnating agent, a viscosity adjusting agent, a wetting agent, etc. Contains choline and inositol belong to vitamin B group, has excellent nutritional effect. Contained in the brain phospholipids have antioxidant or metal chelation, glycerol phosphate has a sound role in the nervous system. Lecithin has a role in the prevention and treatment of hypertension. GMP is a limitation (FDA,§ 172.484,2000). |
Use | Nutrition Medicine. For the prevention of atherosclerosis, hypertension, heart disease, Alzheimer's disease, gout, diabetes, neurasthenia. Can also be used for the preparation of bacterial culture medium. Phospholipids is a powerful emulsifier, can cholesterol, fat "emulsification" into very fine particles, and even dissolve the formation of "atherosclerotic plaques", thereby reducing blood lipids, reduce the chance of stroke and myocardial infarction and other attacks. As an emulsifier, phospholipids can also help the body absorb fat-soluble vitamins A, D, E, K, etc., for the normal operation of the human body. Note that different preparations have different curative effects. used as health food raw materials, emulsifier, quality improver, injection emulsifier and Liposome raw materials can effectively improve and prevent arteriosclerosis, hypertension, heart disease and stroke, and can enhance cell viability, regulates the nervous system biochemical studies, the major structural phospholipids in the brain. The largest use of soybean hatching phospholipid is as a food additive, and the base is as a feed additive. Also used in medicine, cosmetics, and leather, asphalt emulsifier. |
production method | 1. Method for extraction of sheep brain fresh brain was taken and ground with a wring machine. It was immersed three times in industrial acetone in cold place for 24h each time with frequent stirring. After each impregnation, filter with thread cloth and bamboo cloth, and put the filter residue into the bag for the last time and press it with a press. The filtrate is used for the production of cholesterol. The residue was evaporated to acetone and immersed in ether for three times in the cold place for 24h each time. The ether solution was filtered, the filtrates were combined, and ether was added to the distiller. The residue was dissolved in 95% ethanol, dissolved by heating and then cooled to precipitate. The phospholipids of the brain sink at the bottom, the cholesterol floats on top into a thin film, The lecithin is dissolved in ethanol. The lecithin ethanol solution was distilled to recover ethanol, and the concentrated solution was slowly poured into acetone, precipitated, filtered, washed with acetone, heated to remove acetone and ethanol, and dried under vacuum to obtain phosphatidylcholine. Most of the phosphorus compounds extracted from soybean are phytin and phytate, the main component of phytin and magnesium. But the phospholipid is also the content of soybean in a considerable amount of organic phosphorus compounds, fatty acid glycerides combined with phosphorus and amines in the material, such as lecithin, brain phospholipids. Soybean oil is prepared from soybean, and the quality of the separated soybean oil is dehydrated by a vacuum dryer, and then 25-35% of vegetable oil is added to obtain a commercially available lecithin in the form of sugar. method 1. Taking the brain stem as raw material to extract cholesterol and brain phospholipids, adding 3 times the amount of acetone to impregnate the brain for 20-24H, stirring continuously, filtering, and filtering filtrate to prepare cholesterol. Filter cake vacuum drying, add 2-3 times the amount of ethanol, extraction 4-5 times, filtration, precipitation vacuum drying, preparation of brain phospholipid, filtrate vacuum concentration to concentrate. Preparation of finished lecithin concentrate with half times the amount of ether, standing for 2H, precipitation, filtration, to get a clear liquid, add acetone under rapid stirring, precipitation, filtration, collection of ointment, it was washed twice with acetone and dried under vacuum to obtain a finished lecithin product. Concentrated liquid [diethyl ether] →[2H] clear liquid [acetone] → lecithin finished product method 2, taking sheep brain as raw material to extract cholesterol fresh sheep brain, crushing, acetone (3 times, 2.5 times, 1.5 times the amount) 3 times, each 24H, stirring, filtering and pressing, the filtrate to make cholesterol, filter cake blow dry. Extract, dissolve, concentrate the filter cake with ether (3 times the amount, 2.5 times the amount, 1.5 times the amount) extract 3 times, each time 24H, stir, filter, filtrate, concentrate. Add a small amount of ethanol, heated to dissolve, cold chamber precipitation 24H, collect the precipitate, in the cold place with ethanol immersion 3-4 times, each time 3 times the amount, heating dissolution, cooling, precipitation 24H, pour out the supernatant. The supernatant was concentrated in vacuo to give a concentrate. Filter cake [diethyl ether] → filtrate [concentrated] → concentrate [ethanol] → supernatant [concentrated] → concentrate preparation of finished lecithin concentrate with constant stirring add half the amount of diethyl ether, let it stand for 2H, filter to obtain a clear solution of diethyl ether. Under rapid stirring, the clear solution of diethyl ether is added to acetone to precipitate a precipitate, finished lecithin. Concentrate [ether] → clear solution [acetone] → lecithin finished product method 3. Preparation of paste with yeast as raw material dry yeast powder was sieved through 60-80 mesh, add 3 times the amount of 82%-84% ethanol extraction 18-24H, at 70 ℃ for 3H, constant stirring, let cool to below 30 ℃, filter, filter residue extraction 2 times, pull out ethanol, combined extract, 70 ° C vacuum concentration, concentration time is not more than 24h, the paste. The residue was used to extract ribonucleic acid and yeast polysaccharide. Dry yeast or Geotrichum [ethanol, first 70 ℃, then 30 ℃]→ extract [70 ℃]→ preparation of paste concentrate take paste with 5%-10% of water, add 3-5 times the amount of ether, vigorously stir for 2-3H, stand for 16-20h, discard the middle and lower liquid, the upper ether liquid is placed in -5 ℃ refrigerator for 20-24H, ergosterol crystallization, filtering, filtrate distillation, about 1/2 ether was recovered, and then placed in a -5 ° C. Refrigerator for 18-22H. Anhydrous sodium sulfate was added and filtered to obtain ether filtrate. Paste [H2O, diethyl ether] →[Na2SO4] filtrate [distillation] → concentrate preparation of ethanol supernatant concentrate Add 3-5 times the amount of acetone, stir while adding, place for a moment after adding, the mixture of ether and acetone was poured out, washed with anhydrous acetone for 3-4 times to obtain a precipitate. The precipitate was added with 2 times the amount of anhydrous ethanol, heated to 70 ° C., stirred for 1-2H to dissolve, and allowed to stand in the cold storage. The ethanol supernatant was decanted and precipitated as a crude coagulation product. Preparation of lecithin product ethanol supernatant was distilled, ethanol was recovered, precipitate was obtained, anhydrous ether was added, stirred, dissolved, and the precipitate was allowed to stand for 7 days, the supernatant was absorbed, 1.5 times the amount of acetone was added to precipitate, acetone was poured out, the precipitate was washed for 3-4 times, dissolved with ethanol at 70 ° C., and dried to obtain a finished lecithin product. Ethanol supernatant [distillation] → precipitate [ether] → supernatant [acetone, ethanol] → lecithin product method IV, extract cholesterol and lecithin with brain and spinal cord as raw materials, take fresh or frozen brain or spinal cord, remove membrane and blood stained and other impurities, mince, impregnate with 1.2 times the amount of acetone for 4.5h, stir constantly, filter, this was repeated 5 times, and the filtrate was used to prepare cholesterol. The filter cake was vacuum dried, 2-3 times the amount of ethanol was added, extracted at 35-40 ° C. For 12h, filtered, and extracted once again. The filter cake was vacuum dried to prepare cephalin, and the filtrate was used to prepare lecithin. Preparation of precipitate the filtrate was concentrated to 1/3 volume in vacuo to obtain a concentrated solution, which was cooled overnight, filtered, the filtrate was added with saturated solution of cadmium chloride, precipitated, filtered, the precipitate was collected, and 2 times the amount of ether was added, the ethyl ether was removed by shaking, centrifugation and repeated 8-10 times to collect the precipitate. Filtrate [concentrated] → concentrated solution [cadmium chloride, diethyl ether] → preparation of precipitate concentrate precipitate add 4 times the amount of chloroform, shake, to obtain dissolved liquid (turbid), add 25% ammonia methanol solution, precipitation, centrifugation, Centrifugal liquid vacuum concentration near dry, to obtain concentrate. Precipitate [chloroform] → dissolved solution [ammonia methanol solution] → concentrate preparation of finished lecithin concentrate with anhydrous ether, vacuum concentration, repeated treatment 2 times to remove water, to obtain concentrate, A small amount of ether was added, poured into human acetone, allowed to stand, filtered, and the precipitate was collected and dried under vacuum to obtain a finished lecithin product. Concentrate [anhydrous ether] → concentrate [ether, acetone] → finished lecithin. |
toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |