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Lecithin (, from the Greek ''lekithos'' "
yolk Among animals which produce eggs, the yolk (; also known as the vitellus) is the nutrient-bearing portion of the egg whose primary function is to supply food for the development of the embryo. Some types of egg contain no yolk, for example ...
") is a generic term to designate any group of yellow-brownish fatty substances occurring in animal and plant tissues which are
amphiphilic An amphiphile (from the Greek αμφις amphis, both, and φιλíα philia, love, friendship), or amphipath, is a chemical compound possessing both hydrophilic (''water-loving'', polar) and lipophilic (''fat-loving'') properties. Such a compo ...
– they attract both water and fatty substances (and so are both
hydrophilic A hydrophile is a molecule or other molecular entity that is attracted to water molecules and tends to be dissolved by water.Liddell, H.G. & Scott, R. (1940). ''A Greek-English Lexicon'' Oxford: Clarendon Press. In contrast, hydrophobes are ...
and
lipophilic Lipophilicity (from Greek λίπος "fat" and φίλος "friendly"), refers to the ability of a chemical compound to dissolve in fats, oils, lipids, and non-polar solvents such as hexane or toluene. Such non-polar solvents are themselves lipo ...
), and are used for smoothing food textures, emulsifying,
homogenizing Homogeneity and heterogeneity are concepts often used in the sciences and statistics relating to the uniformity of a substance or organism. A material or image that is homogeneous is uniform in composition or character (i.e. color, shape, s ...
liquid mixtures, and repelling sticking materials. Lecithins are mixtures of
glycerophospholipid Glycerophospholipids or phosphoglycerides are glycerol-based phospholipids. They are the main component of biological membranes. Two major classes are known: those for bacteria and eukaryotes and a separate family for archaea. Structures The t ...
s including
phosphatidylcholine Phosphatidylcholines (PC) are a class of phospholipids that incorporate choline as a headgroup. They are a major component of biological membranes and can be easily obtained from a variety of readily available sources, such as egg yolk or soybea ...
,
phosphatidylethanolamine Phosphatidylethanolamine (PE) is a class of phospholipids found in biological membranes. They are synthesized by the addition of cytidine diphosphate- ethanolamine to diglycerides, releasing cytidine monophosphate. ''S''-Adenosyl methionine can ...
,
phosphatidylinositol Phosphatidylinositol (or Inositol Phospholipid) consists of a family of lipids as illustrated on the right, where red is x, blue is y, and black is z, in the context of independent variation, a class of the phosphatidylglycerides. In such molecul ...
,
phosphatidylserine Phosphatidylserine (abbreviated Ptd-L-Ser or PS) is a phospholipid and is a component of the cell membrane. It plays a key role in cell cycle signaling, specifically in relation to apoptosis. It is a key pathway for viruses to enter cells via ap ...
, and
phosphatidic acid Phosphatidic acids are anionic phospholipids important to cell signaling and direct activation of lipid-gated ion channels. Hydrolysis of phosphatidic acid gives rise to one molecule each of glycerol and phosphoric acid and two molecules of fatty ac ...
. Lecithin was first isolated in 1845 by the French chemist and pharmacist Théodore Gobley. In 1850, he named the phosphatidylcholine ''lécithine''. Gobley originally isolated lecithin from egg yolk – λέκιθος ''(lekithos)'' is "egg yolk" in
Ancient Greek Ancient Greek includes the forms of the Greek language used in ancient Greece and the ancient world from around 1500 BC to 300 BC. It is often roughly divided into the following periods: Mycenaean Greek (), Dark Ages (), the Archaic p ...
– and established the complete chemical formula of phosphatidylcholine in 1874; in between, he demonstrated the presence of lecithin in a variety of biological materials, including
venous blood Venous blood is deoxygenated blood which travels from the peripheral blood vessels, through the venous system into the right atrium of the heart. Deoxygenated blood is then pumped by the right ventricle to the lungs via the pulmonary artery wh ...
, human lungs, bile,
roe Roe ( ) or hard roe is the fully ripe internal egg masses in the ovaries, or the released external egg masses, of fish and certain marine animals such as shrimp, scallop, sea urchins and squid. As a seafood, roe is used both as a cooked in ...
, and
brains A brain is an organ that serves as the center of the nervous system in all vertebrate and most invertebrate animals. It is located in the head, usually close to the sensory organs for senses such as vision. It is the most complex organ in a v ...
of humans, sheep and chicken. Lecithin can easily be extracted chemically using solvents such as
hexane Hexane () is an organic compound, a straight-chain alkane with six carbon atoms and has the molecular formula C6H14. It is a colorless liquid, odorless when pure, and with boiling points approximately . It is widely used as a cheap, relatively ...
,
ethanol Ethanol (abbr. EtOH; also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound. It is an alcohol with the chemical formula . Its formula can be also written as or (an ethyl group linked to a ...
,
acetone Acetone (2-propanone or dimethyl ketone), is an organic compound with the formula . It is the simplest and smallest ketone (). It is a colorless, highly volatile and flammable liquid with a characteristic pungent odour. Acetone is miscib ...
,
petroleum ether Petroleum ether is the petroleum fraction consisting of aliphatic hydrocarbons and boiling in the range 35–60 °C, and commonly used as a laboratory solvent. Despite the name, petroleum ether is not classified as an ether; the term is used ...
or
benzene Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms ...
; or extraction can be done mechanically. Common sources include egg yolk, marine foods,
soybean The soybean, soy bean, or soya bean (''Glycine max'') is a species of legume native to East Asia, widely grown for its edible bean, which has numerous uses. Traditional unfermented food uses of soybeans include soy milk, from which tofu a ...
s, milk,
rapeseed Rapeseed (''Brassica napus ''subsp.'' napus''), also known as rape, or oilseed rape, is a bright-yellow flowering member of the family Brassicaceae (mustard or cabbage family), cultivated mainly for its oil-rich seed, which naturally contains a ...
,
cottonseed Cottonseed is the seed of the cotton plant. Composition The mature seeds are brown ovoids weighing about a tenth of a gram. By weight, they are 60% cotyledon, 32% coat and 8% embryonic root and shoot. These are 20% protein, 20% oil and 3.5% sta ...
, and sunflower oil. It has low
solubility In chemistry, solubility is the ability of a substance, the solute, to form a solution with another substance, the solvent. Insolubility is the opposite property, the inability of the solute to form such a solution. The extent of the solub ...
in water, but is an excellent emulsifier. In aqueous solution, its phospholipids can form either
liposome A liposome is a small artificial Vesicle (biology and chemistry), vesicle, spherical in shape, having at least one lipid bilayer. Due to their hydrophobicity and/or hydrophilicity, biocompatibility, particle size and many other properties, lipo ...
s, bilayer sheets,
micelle A micelle () or micella () (plural micelles or micellae, respectively) is an aggregate (or supramolecular assembly) of surfactant amphipathic lipid molecules dispersed in a liquid, forming a colloidal suspension (also known as associated coll ...
s, or
lamellar structure In materials science, lamellar structures or microstructures are composed of fine, alternating layers of different materials in the form of lamellae. They are often observed in cases where a phase transition front moves quickly, leaving behind ...
s, depending on hydration and temperature. This results in a type of surfactant that usually is classified as
amphipathic An amphiphile (from the Greek αμφις amphis, both, and φιλíα philia, love, friendship), or amphipath, is a chemical compound possessing both hydrophilic (''water-loving'', polar) and lipophilic (''fat-loving'') properties. Such a compoun ...
. Lecithin is sold as a food additive and dietary supplement. In cooking, it is sometimes used as an emulsifier and to prevent sticking, for example in non-stick cooking spray.


Production

Commercial lecithin, as used by food manufacturers, is a mixture of phospholipids in
oil An oil is any nonpolar chemical substance that is composed primarily of hydrocarbons and is hydrophobic (does not mix with water) & lipophilic (mixes with other oils). Oils are usually flammable and surface active. Most oils are unsaturated ...
. The lecithin can be obtained by water degumming the extracted oil of seeds. It is a mixture of various phospholipids, and the composition depends on the origin of the lecithin. A major source of lecithin is
soybean oil Soybean oil (British English: soyabean oil) is a vegetable oil extracted from the seeds of the soybean (''Glycine max''). It is one of the most widely consumed cooking oils and the second most consumed vegetable oil. As a drying oil, processed s ...
. Because of the EU requirement to declare additions of allergens in foods, in addition to regulations regarding genetically modified crops, a gradual shift to other sources of lecithin (such as sunflower lecithin) is taking place. The main phospholipids in lecithin from soy and sunflower are
phosphatidylcholine Phosphatidylcholines (PC) are a class of phospholipids that incorporate choline as a headgroup. They are a major component of biological membranes and can be easily obtained from a variety of readily available sources, such as egg yolk or soybea ...
,
phosphatidylinositol Phosphatidylinositol (or Inositol Phospholipid) consists of a family of lipids as illustrated on the right, where red is x, blue is y, and black is z, in the context of independent variation, a class of the phosphatidylglycerides. In such molecul ...
,
phosphatidylethanolamine Phosphatidylethanolamine (PE) is a class of phospholipids found in biological membranes. They are synthesized by the addition of cytidine diphosphate- ethanolamine to diglycerides, releasing cytidine monophosphate. ''S''-Adenosyl methionine can ...
,
phosphatidylserine Phosphatidylserine (abbreviated Ptd-L-Ser or PS) is a phospholipid and is a component of the cell membrane. It plays a key role in cell cycle signaling, specifically in relation to apoptosis. It is a key pathway for viruses to enter cells via ap ...
, and
phosphatidic acid Phosphatidic acids are anionic phospholipids important to cell signaling and direct activation of lipid-gated ion channels. Hydrolysis of phosphatidic acid gives rise to one molecule each of glycerol and phosphoric acid and two molecules of fatty ac ...
. They are often abbreviated to PC, PI, PE, PS and PA, respectively. Purified phospholipids are produced by companies commercially.


Hydrolysed lecithin

To modify the performance of lecithin to make it suitable for the product to which it is added, it may be hydrolysed enzymatically. In hydrolysed lecithins, a portion of the phospholipids have one fatty acid removed by
phospholipase A phospholipase is an enzyme that hydrolyzes phospholipids into fatty acids and other lipophilic substances. Acids trigger the release of bound calcium from cellular stores and the consequent increase in free cytosolic Ca2+, an essential step in ...
. Such phospholipids are called lysophospholipids. The most commonly used phospholipase is phospholipase A2, which removes the
fatty acid In chemistry, particularly in biochemistry, a fatty acid is a carboxylic acid with an aliphatic chain, which is either saturated or unsaturated. Most naturally occurring fatty acids have an unbranched chain of an even number of carbon atoms, ...
at the C2 position of glycerol. Lecithins may also be modified by a process called
fractionation Fractionation is a separation process in which a certain quantity of a mixture (of gases, solids, liquids, enzymes, or isotopes, or a suspension) is divided during a phase transition, into a number of smaller quantities (fractions) in which the ...
. During this process, lecithin is mixed with an alcohol, usually
ethanol Ethanol (abbr. EtOH; also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound. It is an alcohol with the chemical formula . Its formula can be also written as or (an ethyl group linked to a ...
. Some phospholipids, such as phosphatidylcholine, have good solubility in ethanol, whereas most other phospholipids do not dissolve well in ethanol. The ethanol is separated from the lecithin sludge, after which the ethanol is removed by evaporation to obtain a phosphatidylcholine-enriched lecithin fraction.


Genetically modified crops as a source of lecithin

As described above, lecithin is highly processed. Therefore, genetically modified (GM)
protein Proteins are large biomolecules and macromolecules that comprise one or more long chains of amino acid residues. Proteins perform a vast array of functions within organisms, including catalysing metabolic reactions, DNA replication, res ...
or DNA from the original
GM crop GM or Gm may refer to: Companies * General Motors, US automobile manufacturing company which was founded in 1908 ** Motors Liquidation Company, the US automobile manufacturing company known as General Motors Corporation from 1916 to 2009 * ...
from which it is derived often is undetectable – in other words, it is not substantially different from lecithin derived from non-GM crops. Nonetheless, consumer concerns about
genetically modified food Genetically modified foods (GM foods), also known as genetically engineered foods (GE foods), or bioengineered foods are foods produced from organisms that have had changes introduced into their DNA using the methods of genetic engineering. Gene ...
have extended to highly purified derivatives from GM food, such as lecithin. This concern led to policy and regulatory changes in the EU in 2000, when Commission Regulation ( EC) 50/2000 was passed which required labelling of food containing additives derived from GMOs, including lecithin. Because it is nearly impossible to detect the origin of derivatives such as lecithin, the European regulations require those who wish to sell lecithin in
Europe Europe is a large peninsula conventionally considered a continent in its own right because of its great physical size and the weight of its history and traditions. Europe is also considered a subcontinent of Eurasia and it is located entirel ...
to use a meticulous, but essential system of identity preservation (IP).


Properties and applications

Lecithins have
emulsification An emulsion is a mixture of two or more liquids that are normally immiscible (unmixable or unblendable) owing to liquid-liquid phase separation. Emulsions are part of a more general class of two-phase systems of matter called colloids. Altho ...
and lubricant properties, and are a surfactant. They can be completely
metabolized Metabolism (, from el, μεταβολή ''metabolē'', "change") is the set of life-sustaining chemical reactions in organisms. The three main functions of metabolism are: the conversion of the energy in food to energy available to run cell ...
(see inositol) by humans, so are well tolerated by humans and nontoxic when ingested. The major components of commercial soybean-derived lecithin are: * 33–35% soybean oil * 20–21%
phosphatidylinositol Phosphatidylinositol (or Inositol Phospholipid) consists of a family of lipids as illustrated on the right, where red is x, blue is y, and black is z, in the context of independent variation, a class of the phosphatidylglycerides. In such molecul ...
s * 19–21%
phosphatidylcholine Phosphatidylcholines (PC) are a class of phospholipids that incorporate choline as a headgroup. They are a major component of biological membranes and can be easily obtained from a variety of readily available sources, such as egg yolk or soybea ...
* 8–20%
phosphatidylethanolamine Phosphatidylethanolamine (PE) is a class of phospholipids found in biological membranes. They are synthesized by the addition of cytidine diphosphate- ethanolamine to diglycerides, releasing cytidine monophosphate. ''S''-Adenosyl methionine can ...
* 5–11% other phosphatides * 5% free
carbohydrate In organic chemistry, a carbohydrate () is a biomolecule consisting of carbon (C), hydrogen (H) and oxygen (O) atoms, usually with a hydrogen–oxygen atom ratio of 2:1 (as in water) and thus with the empirical formula (where ''m'' may or m ...
s * 2–5% sterols * 1% moisture Lecithin is used for applications in human food, animal feed, pharmaceuticals, paints, and other industrial applications. Applications include: * In the
pharmaceutical industry The pharmaceutical industry discovers, develops, produces, and markets drugs or pharmaceutical drugs for use as medications to be administered to patients (or self-administered), with the aim to cure them, vaccinate them, or alleviate symptoms. ...
, it acts as a wetting agent, stabilizing agent and a choline enrichment carrier, helps in emulsification and encapsulation, and is a good dispersing agent. It can be used in manufacture of intravenous fat infusions and for therapeutic use. * In animal feed, it enriches fat and protein and improves pelletization. * In the paint industry, it forms protective coatings for surfaces with painting and
printing ink Ink is a gel, sol, or solution that contains at least one colorant, such as a dye or pigment, and is used to color a surface to produce an image, text, or design. Ink is used for drawing or writing with a pen, brush, reed pen, or quill. Thicker ...
, helps as a
rust Rust is an iron oxide, a usually reddish-brown oxide formed by the reaction of iron and oxygen in the catalytic presence of water or air moisture. Rust consists of hydrous iron(III) oxides (Fe2O3·nH2O) and iron(III) oxide-hydroxide (FeO( ...
inhibitor, is a colour intensifying agent,
catalyst Catalysis () is the process of increasing the rate of a chemical reaction by adding a substance known as a catalyst (). Catalysts are not consumed in the reaction and remain unchanged after it. If the reaction is rapid and the catalyst recyc ...
, conditioning aid modifier, and dispersing aid; it is a good stabilizing and suspending agent, emulsifier, and
wetting agent Surfactants are chemical compounds that decrease the surface tension between two liquids, between a gas and a liquid, or interfacial tension between a liquid and a solid. Surfactants may act as detergents, wetting agents, emulsifiers, foaming ...
, helps in maintaining uniform mixture of several
pigment A pigment is a colored material that is completely or nearly insoluble in water. In contrast, dyes are typically soluble, at least at some stage in their use. Generally dyes are often organic compounds whereas pigments are often inorganic compou ...
s, helps in grinding of
metal oxide An oxide () is a chemical compound that contains at least one oxygen atom and one other element in its chemical formula. "Oxide" itself is the dianion of oxygen, an O2– (molecular) ion. with oxygen in the oxidation state of −2. Most of the E ...
pigments, is a spreading and mixing aid, prevents hard settling of pigments, eliminates
foam Foams are materials formed by trapping pockets of gas in a liquid or solid. A bath sponge and the head on a glass of beer are examples of foams. In most foams, the volume of gas is large, with thin films of liquid or solid separating the ...
in water-based paints, and helps in fast dispersion of
latex Latex is an emulsion (stable dispersion) of polymer microparticles in water. Latexes are found in nature, but synthetic latexes are common as well. In nature, latex is found as a milky fluid found in 10% of all flowering plants (angiosperms ...
-based paints. * Lecithin also may be used as a
release agent A release agent (also mold release agent, release coating, or mold release coating) is a chemical used to prevent other materials from bonding to surfaces. It can provide a solution in processes involving mold release, die-cast release, plastic r ...
for
plastic Plastics are a wide range of synthetic or semi-synthetic materials that use polymers as a main ingredient. Their plasticity makes it possible for plastics to be moulded, extruded or pressed into solid objects of various shapes. This adaptab ...
s, an anti-sludge additive in motor lubricants, an anti-gumming agent in gasoline, and an emulsifier, spreading agent, and antioxidant in textile, rubber, and other industries.


Food additive

The nontoxicity of lecithin leads to its use with food, as an additive or in food preparation. It is used commercially in foods requiring a natural emulsifier or lubricant. In confectionery, it reduces viscosity, replaces more expensive ingredients, controls sugar crystallization and the flow properties of
chocolate Chocolate is a food made from roasted and ground cacao seed kernels that is available as a liquid, solid, or paste, either on its own or as a flavoring agent in other foods. Cacao has been consumed in some form since at least the Olmec civ ...
, helps in the homogeneous mixing of ingredients, improves shelf life for some products, and can be used as a coating. In emulsions and fat spreads, such as margarines with a high fat content of more than 75%, it stabilizes emulsions, reduces spattering (splashing and scattering of oil droplets) during frying, improves texture of spreads and flavor release. In doughs and baking, it reduces fat and egg requirements, helps even out distribution of ingredients in dough, stabilizes fermentation (food), fermentation, increases volume, protects yeast cells in dough when frozen, and acts as a releasing agent to prevent sticking and simplify cleaning. It improves wetting properties of
hydrophilic A hydrophile is a molecule or other molecular entity that is attracted to water molecules and tends to be dissolved by water.Liddell, H.G. & Scott, R. (1940). ''A Greek-English Lexicon'' Oxford: Clarendon Press. In contrast, hydrophobes are ...
powders (such as low-fat proteins) and
lipophilic Lipophilicity (from Greek λίπος "fat" and φίλος "friendly"), refers to the ability of a chemical compound to dissolve in fats, oils, lipids, and non-polar solvents such as hexane or toluene. Such non-polar solvents are themselves lipo ...
powders (such as cocoa powder), controls dust, and helps complete dispersion in water. Lecithin keeps Cocoa solids, cocoa and cocoa butter in a chocolate bar, candy bar from separating. It can be used as a component of cooking sprays to prevent sticking and as a releasing agent. Lecithin is approved by the United States Food and Drug Administration for human consumption with the status "generally recognized as safe". Lecithin is admitted by the EU as a food additive, designated as E number, E322.


Dietary supplement

Because it contains
phosphatidylcholine Phosphatidylcholines (PC) are a class of phospholipids that incorporate choline as a headgroup. They are a major component of biological membranes and can be easily obtained from a variety of readily available sources, such as egg yolk or soybea ...
s, lecithin is a source of choline, an essential nutrient. There is no evidence-based medicine, clinical evidence on the safety or efficacy of high doses of lecithin to improve milk flow in breast-feeding mothers or infants. Soy lecithin does not contain enough allergenic proteins for most people allergic to soy, although the US FDA only exempts a few soy lecithin products from its mandatory requirements for allergenic source labeling. A 2003 review found no benefit of lecithin in people with dementia.


Religious restrictions

Soy-derived lecithin is considered by some to be ''kitniyot'' and prohibited on Passover for Ashkenazi Jews when many grain-based foods are forbidden, but not at other times. This does not necessarily affect Sephardi Jews, who do not have the same restrictions on rice and ''kitniyot'' during Passover. Muslims are not forbidden to eat lecithin per se; however, since it may be derived from animal as well as plant sources, care must be taken to ensure this source is Halal#Dietary laws, halal. Lecithin derived from plants and egg yolks is permissible, as is that derived from animals slaughtered according to the rules of ''dhabihah''.Islamic Food and Nutrition Council of America FAQ
IFANCA: Consumer FAQ
. Retrieved on July 7, 2010. The practice of consuming Halal products is not widespread among Muslims, the practice is common with Muslims who follow Sharia laws.


See also

*Phytosome


References


External links


Introduction to Lecithin
(University of Erlangen)
FDA Industry guideline for soy lecithin labeling
* * {{Authority control Cholinergics Food emulsifiers Phospholipids Membrane biology Nootropics Soy products Zwitterionic surfactants E-number additives