Lecithin
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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 – 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 n ...
and lipophilic), and are used for smoothing food textures,
emulsifying 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. Although ...
, homogenizing liquid mixtures, and repelling sticking materials. Lecithins are mixtures of glycerophospholipids including phosphatidylcholine, phosphatidylethanolamine,
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, and phosphatidic acid. 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 pe ...
– 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, human lungs,
bile Bile (from Latin ''bilis''), or gall, is a dark-green-to-yellowish-brown fluid produced by the liver of most vertebrates that aids the digestion of lipids in the small intestine. In humans, bile is produced continuously by the liver (liver bi ...
, roe, 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 i ...
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, relative ...
,
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 miscibl ...
,
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 ...
s, milk, rapeseed, cottonseed, 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 solubi ...
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. Althoug ...
. 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,
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 behin ...
s, depending on hydration and temperature. This results in a type of
surfactant 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, emulsion#Emulsifiers , ...
that usually is classified as amphipathic. Lecithin is sold as a food additive and
dietary supplement A dietary supplement is a manufactured product intended to supplement one's diet by taking a pill, capsule, tablet, powder, or liquid. A supplement can provide nutrients either extracted from food sources or that are synthetic in order ...
. 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 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, processe ...
. 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 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, 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. 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, f ...
at the C2 position of glycerol. Lecithins may also be modified by a process called fractionation. 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 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 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 Continent#Subcontinents, subcontinent of Eurasia ...
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, t ...
properties, and are a
surfactant 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, emulsion#Emulsifiers , ...
. 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 Toxicity is the degree to which a chemical substance or a particular mixture of substances can damage an organism. Toxicity can refer to the effect on a whole organism, such as an animal, bacterium, or plant, as well as the effect on a subst ...
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 * 8–20% phosphatidylethanolamine * 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 o ...
s * 2–5%
sterol Sterol is an organic compound with formula , whose molecule is derived from that of gonane by replacement of a hydrogen atom in position 3 by a hydroxyl group. It is therefore an alcohol of gonane. More generally, any compounds that contain the go ...
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, 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 to ...
, it enriches fat and protein and improves pelletization. * In the paint 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( ...
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, 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 pigments, is a spreading and mixing aid, prevents hard settling of pigments, eliminates foam 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 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 adapta ...
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 ci ...
, 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
dough Dough is a thick, malleable, sometimes elastic paste 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 yeast or other leavenin ...
s and baking, it reduces fat and egg requirements, helps even out distribution of ingredients in dough, stabilizes
fermentation Fermentation is a metabolic process that produces chemical changes in organic substrates through the action of enzymes. In biochemistry, it is narrowly defined as the extraction of energy from carbohydrates in the absence of oxygen. In food p ...
, increases volume, protects
yeast Yeasts are eukaryotic, single-celled microorganisms classified as members of the fungus kingdom. The first yeast originated hundreds of millions of years ago, and at least 1,500 species are currently recognized. They are estimated to constit ...
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 n ...
powders (such as low-fat proteins) and lipophilic powders (such as cocoa powder), controls dust, and helps complete dispersion in water. Lecithin keeps
cocoa Cocoa may refer to: Chocolate * Chocolate * ''Theobroma cacao'', the cocoa tree * Cocoa bean, seed of ''Theobroma cacao'' * Chocolate liquor, or cocoa liquor, pure, liquid chocolate extracted from the cocoa bean, including both cocoa butter an ...
and
cocoa butter Cocoa butter, also called theobroma oil, is a pale-yellow, edible fat extracted from the cocoa bean. It is used to make chocolate, as well as some ointments, toiletries, and pharmaceuticals. Cocoa butter has a cocoa flavor and aroma. Its melt ...
in a
candy bar A candy bar is a type of candy that is in the shape of a bar. The most common type of candy bar is the chocolate bar, including both bars made of solid chocolate and combination candy bars, which are candy bars that combine chocolate with othe ...
from separating. It can be used as a component of
cooking spray Cooking spray is a spray form of an oil as a lubricant, lecithin as an emulsifier, and a propellant such as food-grade alcohol, nitrous oxide, carbon dioxide or propane. Cooking spray is applied to frying pans and other cookware to prevent fo ...
s to prevent sticking and as a releasing agent. Lecithin is approved by the
United States The United States of America (U.S.A. or USA), commonly known as the United States (U.S. or US) or America, is a country Continental United States, primarily located in North America. It consists of 50 U.S. state, states, a Washington, D.C., ...
Food and Drug Administration The United States Food and Drug Administration (FDA or US FDA) is a federal agency of the Department of Health and Human Services. The FDA is responsible for protecting and promoting public health through the control and supervision of food ...
for
human Humans (''Homo sapiens'') are the most abundant and widespread species of primate, characterized by bipedalism and exceptional cognitive skills due to a large and complex brain. This has enabled the development of advanced tools, cultu ...
consumption with the status " generally recognized as safe". Lecithin is admitted by the EU as a food additive, designated as E322.


Dietary supplement

Because it contains phosphatidylcholines, lecithin is a source of choline, an essential nutrient. There is no 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 Dementia is a disorder which manifests as a set of related symptoms, which usually surfaces when the brain is damaged by injury or disease. The symptoms involve progressive impairments in memory, thinking, and behavior, which negatively affe ...
.


Religious restrictions

Soy-derived lecithin is considered by some to be ''
kitniyot ''Kitniyot'' ( he, קִטְנִיּוֹת, ''qitniyyot'') is a Hebrew word meaning legumes. During the Passover holiday, however, the word ''kitniyot'' (or ''kitniyos'' in some dialects) takes on a broader meaning to include grains and seeds suc ...
'' and prohibited on
Passover Passover, also called Pesach (; ), is a major Jewish holiday that celebrates the Biblical story of the Israelites escape from slavery in Egypt, which occurs on the 15th day of the Hebrew month of Nisan, the first month of Aviv, or spring. ...
for
Ashkenazi Jews Ashkenazi Jews ( ; he, יְהוּדֵי אַשְׁכְּנַז, translit=Yehudei Ashkenaz, ; yi, אַשכּנזישע ייִדן, Ashkenazishe Yidn), also known as Ashkenazic Jews or ''Ashkenazim'',, Ashkenazi Hebrew pronunciation: , singu ...
when many grain-based foods are forbidden, but not at other times. This does not necessarily affect
Sephardi Jews Sephardic (or Sephardi) Jews (, ; lad, Djudíos Sefardíes), also ''Sepharadim'' , Modern Hebrew: ''Sfaradim'', Tiberian: Səp̄āraddîm, also , ''Ye'hude Sepharad'', lit. "The Jews of Spain", es, Judíos sefardíes (or ), pt, Judeus sefa ...
, who do not have the same restrictions on rice and ''kitniyot'' during Passover.
Muslim Muslims ( ar, المسلمون, , ) are people who adhere to Islam, a monotheistic religion belonging to the Abrahamic tradition. They consider the Quran, the foundational religious text of Islam, to be the verbatim word of the God of Abrah ...
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 this source is 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