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Lecithin ( ; from the
Ancient Greek Ancient Greek (, ; ) includes the forms of the Greek language used in ancient Greece and the classical antiquity, ancient world from around 1500 BC to 300 BC. It is often roughly divided into the following periods: Mycenaean Greek (), Greek ...
"
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 bec ...
") is a generic term to designate any group of yellow-brownish fatty substances occurring in animal and plant tissues which are amphiphilic – they attract both water and fatty substances (and so are both hydrophilic and
lipophilic Lipophilicity (from Greek language, Greek λίπος "fat" and :wikt:φίλος, φίλος "friendly") is the ability of a chemical compound to dissolve in fats, oils, lipids, and non-polar solvents such as hexane or toluene. Such compounds are c ...
), and are used for smoothing food textures, emulsifying, homogenizing 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 in eukaryotic cells. They are a type of lipid, of which its composition affects membrane structure and properties. T ...
s including phosphatidylcholine, phosphatidylethanolamine, phosphatidylinositol, phosphatidylserine, and phosphatidic acid. Lecithin was first isolated in 1845 by the French chemist and pharmacist Théodore Gobley. In 1850, he named the phosphatidylcholine . Gobley originally isolated lecithin from
egg 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 bec ...
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 whi ...
, human lungs,
bile Bile (from Latin ''bilis''), also known as gall, is a yellow-green/misty green fluid produced by the liver of most vertebrates that aids the digestion of lipids in the small intestine. In humans, bile is primarily composed of water, is pro ...
,
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 cooking, c ...
, and
brain The brain is an organ (biology), organ that serves as the center of the nervous system in all vertebrate and most invertebrate animals. It consists of nervous tissue and is typically located in the head (cephalization), usually near organs for ...
s of humans, sheep and chicken. Lecithin can easily be extracted chemically using solvents such as
hexane Hexane () or ''n''-hexane is an organic compound, a straight-chain alkane with six carbon atoms and the molecular formula C6H14. Hexane is a colorless liquid, odorless when pure, and with a boiling point of approximately . It is widely used as ...
,
ethanol Ethanol (also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound with the chemical formula . It is an Alcohol (chemistry), alcohol, with its formula also written as , or EtOH, where Et is the ps ...
,
acetone Acetone (2-propanone or dimethyl ketone) is an organic compound with the chemical formula, formula . It is the simplest and smallest ketone (). It is a colorless, highly Volatile organic compound, volatile, and flammable liquid with a charact ...
,
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 an ether; the term is used only figurativ ...
or
benzene Benzene is an Organic compound, organic chemical compound with the Chemical formula#Molecular formula, molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar hexagonal Ring (chemistry), ring with one hyd ...
; 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. Soy is a staple crop, the world's most grown legume, and an important animal feed. Soy is a key source o ...
s, milk, rapeseed, cottonseed, and sunflower oil. It has low
solubility In chemistry, solubility is the ability of a chemical substance, substance, the solute, to form a solution (chemistry), solution with another substance, the solvent. Insolubility is the opposite property, the inability of the solute to form su ...
in water, but is an excellent
emulsifier 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. Althou ...
. In aqueous solution, its
phospholipid Phospholipids are a class of lipids whose molecule has a hydrophilic "head" containing a phosphate group and two hydrophobic "tails" derived from fatty acids, joined by an alcohol residue (usually a glycerol molecule). Marine phospholipids typ ...
s can form either liposomes, bilayer sheets, micelles, or lamellar structures, depending on hydration and temperature. This results in a type of
surfactant Surfactants are chemical compounds that decrease the surface tension or interfacial tension between two liquids, a liquid and a gas, or a liquid and a solid. The word ''surfactant'' is a Blend word, blend of "surface-active agent", coined in ...
that usually is classified as amphipathic. Lecithin is sold as a
food additive Food additives are substances added to food to preserve flavor or enhance taste, appearance, or other sensory qualities. Some additives, such as vinegar ( pickling), salt ( salting), smoke ( smoking) and sugar ( crystallization), have been used f ...
and
dietary supplement A dietary supplement is a manufactured product intended to supplement a person's diet by taking a pill (pharmacy), pill, capsule (pharmacy), capsule, tablet (pharmacy), tablet, powder, or liquid. A supplement can provide nutrients eithe ...
. 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
phospholipid Phospholipids are a class of lipids whose molecule has a hydrophilic "head" containing a phosphate group and two hydrophobic "tails" derived from fatty acids, joined by an alcohol residue (usually a glycerol molecule). Marine phospholipids typ ...
s in oil. 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. Because of the EU requirement to declare additions of allergens in foods, in addition to regulations regarding
genetically modified crops Genetically modified crops (GM crops) are plants used in agriculture, the DNA of which has been modified using genetic engineering methods. Plant genomes can be engineered by physical methods or by use of '' Agrobacterium'' for the delivery of ...
, 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, phosphatidylinositol, phosphatidylethanolamine, phosphatidylserine, and phosphatidic acid. 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. There are four major classes, termed A, B, C, and D, which are distinguished by the type of reaction which they catalyze: *Phospholipase ...
. Such phospholipids are called lysophospholipids. The most commonly used phospholipase is phospholipase A2, which removes the
fatty acid In chemistry, in particular in biochemistry, a fatty acid is a carboxylic acid with an aliphatic chain, which is either saturated and unsaturated compounds#Organic chemistry, saturated or unsaturated. Most naturally occurring fatty acids have an ...
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 gasses, solids, liquids, enzymes, or isotopes, or a suspension) is divided during a phase transition, into a number of smaller quantities (fractions) in which t ...
. During this process, lecithin is mixed with an alcohol, usually
ethanol Ethanol (also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound with the chemical formula . It is an Alcohol (chemistry), alcohol, with its formula also written as , or EtOH, where Et is the ps ...
. 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 residue (biochemistry), residues. Proteins perform a vast array of functions within organisms, including Enzyme catalysis, catalysing metab ...
or
DNA Deoxyribonucleic acid (; DNA) is a polymer composed of two polynucleotide chains that coil around each other to form a double helix. The polymer carries genetic instructions for the development, functioning, growth and reproduction of al ...
from the original GM crop 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 various methods of genetic engineering. G ...
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 continent located entirely in the Northern Hemisphere and mostly in the Eastern Hemisphere. It is bordered by the Arctic Ocean to the north, the Atlantic Ocean to the west, the Mediterranean Sea to the south, and Asia to the east ...
to use a meticulous, but essential system of identity preservation (IP).


Properties and applications

Lecithins have emulsification and
lubricant A lubricant (sometimes shortened to lube) is a substance that helps to reduce friction between surfaces in mutual contact, which ultimately reduces the heat generated when the surfaces move. It may also have the function of transmitting forces, ...
properties, and are a
surfactant Surfactants are chemical compounds that decrease the surface tension or interfacial tension between two liquids, a liquid and a gas, or a liquid and a solid. The word ''surfactant'' is a Blend word, blend of "surface-active agent", coined in ...
. They can be completely metabolized (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% phosphatidylinositols * 19–21% phosphatidylcholine * 8–20% phosphatidylethanolamine * 5–11% other phosphatides including phosphatidylserine * 5% free
carbohydrate A carbohydrate () is a biomolecule composed of carbon (C), hydrogen (H), and oxygen (O) atoms. The typical hydrogen-to-oxygen atomic ratio is 2:1, analogous to that of water, and is represented by the empirical formula (where ''m'' and ''n'' ...
s * 2–5%
sterol A sterol is any organic compound with a Skeletal formula, skeleton closely related to Cholestanol, cholestan-3-ol. The simplest sterol is gonan-3-ol, which has a formula of , and is derived from that of gonane by replacement of a hydrogen atom on ...
s * 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 is a medical industry that discovers, develops, produces, and markets pharmaceutical goods such as medications and medical devices. Medications are then administered to (or self-administered by) patients for curing ...
, 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 Animal feed is food given to domestic animals, especially livestock, in the course of animal husbandry. There are two basic types: fodder and forage. Used alone, the word ''feed'' more often refers to fodder. Animal feed is an important input ...
, it enriches fat and protein and improves pelletization. * In the
paint Paint is a material or mixture that, when applied to a solid material and allowed to dry, adds a film-like layer. As art, this is used to create an image or images known as a painting. Paint can be made in many colors and types. Most paints are ...
industry, it forms protective coatings for surfaces with painting and printing ink, 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(OH) ...
inhibitor, is a colour intensifying agent,
catalyst Catalysis () is the increase in rate of a chemical reaction due to an added substance known as a catalyst (). Catalysts are not consumed by the reaction and remain unchanged after it. If the reaction is rapid and the catalyst recycles quick ...
, conditioning aid modifier, and dispersing aid; it is a good stabilizing and suspending agent, emulsifier, and wetting agent, helps in maintaining uniform mixture of several
pigment A pigment is a powder used to add or alter color or change visual appearance. Pigments are completely or nearly solubility, insoluble and reactivity (chemistry), chemically unreactive in water or another medium; in contrast, dyes are colored sub ...
s, helps in grinding of metal oxide pigments, is a spreading and mixing aid, prevents hard settling of pigments, eliminates
foam Foams are two-phase materials science, material systems where a gas is dispersed in a second, non-gaseous material, specifically, in which gas cells are enclosed by a distinct liquid or solid material. Note, this source focuses only on liquid ...
in water-based paints, and helps in fast dispersion of
latex Latex is an emulsion (stable dispersion) of polymer microparticles in water. Latices are found in nature, but synthetic latices are common as well. In nature, latex is found as a wikt:milky, milky fluid, which is present in 10% of all floweri ...
-based paints. * Lecithin also may be used as a release agent for
plastic Plastics are a wide range of synthetic polymers, synthetic or Semisynthesis, semisynthetic materials composed primarily of Polymer, polymers. Their defining characteristic, Plasticity (physics), plasticity, allows them to be Injection moulding ...
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 a
food additive Food additives are substances added to food to preserve flavor or enhance taste, appearance, or other sensory qualities. Some additives, such as vinegar ( pickling), salt ( salting), smoke ( smoking) and sugar ( crystallization), have been used f ...
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 cocoa beans that can be a liquid, solid, or paste, either by itself or to flavoring, flavor other foods. Cocoa beans are the processed seeds of the cacao tree (''Theobroma cacao''); unprocesse ...
, 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 In nutrition science, nutrition, biology, and chemistry, fat usually means any ester of fatty acids, or a mixture of such chemical compound, compounds, most commonly those that occur in living beings or in food. The term often refers specif ...
content of more than 75%, it stabilizes emulsions, reduces spattering (splashing and scattering of oil droplets) during
frying Frying is the cooking of food in cooking oil, oil or another fat. Similar to sautéing, pan-fried foods are generally turned over once or twice during cooking to make sure that the food is evenly cooked, using tongs or a spatula, whilst sautéed ...
, improves texture of spreads and flavor release. In
dough Dough is a malleable, sometimes elastic paste made from flour (which itself is made from grains or from leguminous or chestnut crops). Dough is typically made by mixing flour with a small amount of water or other liquid and sometimes includes ...
s and
baking Baking is a method of preparing food that uses dry heat, typically in an oven, but it can also be done in hot ashes, or on hot Baking stone, stones. Bread is the most commonly baked item, but many other types of food can also be baked. Heat is ...
, it reduces fat and egg requirements, helps even out distribution of ingredients in dough, stabilizes
fermentation Fermentation is a type of anaerobic metabolism which harnesses the redox potential of the reactants to make adenosine triphosphate (ATP) and organic end products. Organic molecules, such as glucose or other sugars, are catabolized and reduce ...
, increases volume, protects
yeast Yeasts are eukaryotic, single-celled microorganisms classified as members of the fungus kingdom (biology), kingdom. The first yeast originated hundreds of millions of years ago, and at least 1,500 species are currently recognized. They are est ...
cells in dough when frozen, and acts as a releasing agent to prevent sticking and simplify cleaning. It improves wetting properties of hydrophilic powders (such as low-fat proteins) and
lipophilic Lipophilicity (from Greek language, Greek λίπος "fat" and :wikt:φίλος, φίλος "friendly") is the ability of a chemical compound to dissolve in fats, oils, lipids, and non-polar solvents such as hexane or toluene. Such compounds are c ...
powders (such as cocoa powder), controls dust, and helps complete dispersion in water. Lecithin keeps cocoa and
cocoa butter Cocoa butter, also called theobroma oil, is a pale-yellow, edible Vegetable oil, fat extracted from the cocoa bean (''Theobroma cacao''). It is used to make chocolate, as well as some ointments, toiletries, and pharmaceuticals. Cocoa butter h ...
in a candy bar from separating. It can be used as a component of cooking sprays to prevent sticking and as a releasing agent. In the EU Lecithin is designated at
food additive Food additives are substances added to food to preserve flavor or enhance taste, appearance, or other sensory qualities. Some additives, such as vinegar ( pickling), salt ( salting), smoke ( smoking) and sugar ( crystallization), have been used f ...
E322.


Dietary supplement

Lecithin contains dietary precursors to choline, an essential nutrient, which was formerly classified as a B vitamin (vitamin B4). Lecithin is a mixture of fats that contain phospholipids—including phosphatidylcholine, which makes up about 25 to 35 percent of lecithin—and the human body can convert phosphatidylcholine into choline. Further, about 12 percent of phosphatidylcholine is already choline, so that choline makes up some 3 to 4 percent of lecithin. Phosphatidylcholine is approximately 13.7% choline; as such, about 342 mg of choline is present per 10 grams of lecithin. Therefore, 10 grams of lecithin can be a source for the body to produce about the same amount of choline (342 mg) as can be produced by the body from 2 egg yolks. The recommended intake of choline varies depending on age, sex, and physiological conditions, and is roughly 500 mg per day for adults. Lecithin is
generally recognized as safe Generally recognized as safe (GRAS) is a United States Food and Drug Administration (FDA) designation that a chemical or substance added to food is considered safe by experts under the conditions of its intended use. An ingredient with a GRAS d ...
(GRAS) by the FDA. There is no robust, scientifically validated clinical research investigating the safety and effectiveness of high-dose lecithin supplementation in lactating women and their infants. A meta-analysis found no evidence that high doses of lecithin improved milk flow in breast-feeding mothers or infants, though concluded that "higher maternal choline intake was likely to be associated with better child neurocognition and neurodevelopment." 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. An alternative source of lecithin, derived from sunflowers, is available as a dietary supplement for those with concerns about soy-based foods. A 2003 review of randomized trials found no benefit of lecithin in people with
dementia Dementia is a syndrome associated with many neurodegenerative diseases, characterized by a general decline in cognitive abilities that affects a person's ability to perform activities of daily living, everyday activities. This typically invo ...
.


Religious restrictions

Soy-derived lecithin is considered by some to be '' kitniyot'' and prohibited on
Passover Passover, also called Pesach (; ), is a major Jewish holidays, Jewish holiday and one of the Three Pilgrimage Festivals. It celebrates the Exodus of the Israelites from slavery in Biblical Egypt, Egypt. According to the Book of Exodus, God in ...
for
Ashkenazi Jews Ashkenazi Jews ( ; also known as Ashkenazic Jews or Ashkenazim) form a distinct subgroup of the Jewish diaspora, that emerged in the Holy Roman Empire around the end of the first millennium CE. They traditionally speak Yiddish, a language ...
when many grain-based foods are forbidden, but not at other times. This does not necessarily affect
Sephardi Jews Sephardic Jews, also known as Sephardi Jews or Sephardim, and rarely as Iberian Peninsular Jews, are a Jewish diaspora population associated with the historic Jewish communities of the Iberian Peninsula (Spain and Portugal) and their descendant ...
, who do not have the same restrictions on rice and ''kitniyot'' during Passover.
Muslim Muslims () are people who adhere to Islam, a Monotheism, monotheistic religion belonging to the Abrahamic religions, Abrahamic tradition. They consider the Quran, the foundational religious text of Islam, to be the verbatim word of the God ...
s 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 the source is
halal ''Halal'' (; ) is an Arabic word that translates to in English. Although the term ''halal'' is often associated with Islamic dietary laws, particularly meat that is slaughtered according to Islamic guidelines, it also governs ethical practices ...
. 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.
Sunflower lecithin, sourced from the seeds of sunflowers, is entirely plant-based and may be an option for those with religious or cultural concerns regarding food intake.


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 Nootropics Soy products Zwitterionic surfactants E-number additives Neurotransmitter precursors