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Lecithin ••

L
ecithin has been around for
decades, and hundreds of uses
have been developed for it. A
mature market. however. has a down-
side. Lecithin producers are currently
dealing with an oversupply while
balancing lecithin's venerable role as
jack-of-all-trades with the more prof-
treble value-added lecithin products
of tomorrow.
A mixture of phospholipids,
lecithin most of len is derived from
soybean oil, although other sources
include egg yolk. and brain and liver
tissues. The principal phospholipids
are phosphatidylcholine (PC), phcs-
phatidylclhanoiamine (PE), and
phosphatidylinositol (PI). For a full
description of lecithin composition
and terminology, take a look at
Michael Pamham's article on page
1168.
According to Pamharn, the differ-
ences in lecithin definitions and spec-
ifications around the world are partly
due to the variety of its uses. Lecithin
is more a part of daily life than we

This section I\'as prepared by INFORM


editor/writer Tom Krawcz.yk.

INFORM. Vol. 7. 00. 11 (November 19(6)


1159

consider the possibilities


realize, from the food we eat to the of the soybean, and less than 3% of fiers, and 20% (for use) in a variety of
roads we drive on. soy oil is lecithin. If lecithin makes up industrial applications," said
Lecithin can be found in food only 0.5% of the bean, why even Lawrence Johnson, director of the
products such as cake mixes. cheese. bother with it? Center for Crops Utilization Research
candy. chewing gum, chocolate. Lecithin is extracted as a co-prod- at Iowa State University.
dehydrated foods, ice cream. instant uct of the vegetable oil relining pro- Lecithin is a surfactant. which can
foods. pasta. bakery products, mar- cess. where phosphorus-containing be used to create an emulsion of two
garine. and whipped topping. compounds are removed to improve or more incompatible substances. An
Lecithin also is used for products oil quality. As soybean processing emulsion is a suspension of small
other than food, such as adhesives, increased. lecithin usually was added droplets of one liquid in another that
adsorbants. animal feed and pet food, back 10 the meal or to animal feeds. is immiscible with the first. Phospho-
catalysts. soaps, cosmetics. paints Some oil processors recognized the lipids' hydrophobic fany acid hydro-
and coatings. waxes and polish. inks potential of lecithin as a mullifunc- carbon tails have an affinity for fats
and dyes, computer printer and pho- tiona I additive for food. feed. and and oils, and phospholipids'
tocopier toners. metal processing. industrial applications. hydrophilic polar head groups have an
explosives. pesticides, fertilizers, "Recovery of lecithin and market- affinity for water.
plastic and rubber molding. concrete ing of its many modified forms have The hydrophilic-lipophilic balance
curing. masonry and asphalt prod- become a part of the economics of (HLB) roughly indicates an emulsifi-
ucts. dust-control agents. magnetic soybean processing," said Frank er's preference for oil or water.
media, leather tanning. lubricants, Orthoefer. an industry consultant. Lecithins can be processed to obtain
oil-spill control. textile manufactur- Soybean oil is removed from soy- an HLB of2 (oil-loving) to 12 (water-
ing, production of plastics, paper pro- bean (flakes) with a solvent. usually loving). Low HLB indicates more effi-
duction and coating, wood preserve- hexane. Filtered soy oil can be cient water-in-oil (w/o) emulsification
lives, and release agents. degummed by adding water and cen- properties, and high HLB indicates
trifuging the mixture to separate the more efficient ojl-i n-water (o/w)
What is lecithin? hydrated gums from the oil. About emulsification.
Soybean oil makes up less than 20% 90% of the phospholipids in oil can be The primary usage of lecithin in
removed by water degumming. food is as an emulsifier. For other
Wet gums require immediate pro- food uses, it softens and retains mois-
cessing, as they are high in moisture ture, reduces viscosity, stabilizes, and
(roughly 50% water) and will begin disperses. In baking, lecithin com-
decomposing within an hour or two. plexes with gluten proteins as a dough
To process gums to a crude lecithin conditioner and acts as a wetting
grade, the wet gums are dried and agent.
quickly cooled. Lecithin can be With a growing trend toward
bleached as wet gums between the reduced-fat products, lecithin is find-
centrifuging and drying stages. ing a niche of increasing business. Fat
The dried gums are in a plastic removal from a baked food product
state, and can be left in this form or formulation may cause lowered
fluidized by adding oil or edible fatty lubricity and handling properties,

~------------+l~ acids to reach viscosities that promote


easier handling. High-clarity lecithins
are made with more filtering, either in
the miscefla (the mixture of hexane
moisture migration, and poor aeration
and cell structure. Many of these
effects can be lessened by incorporat-
ing lecithin or a mix of lecithin and
applied to soybean flakes and the other emulsifiers and gums into the
extracted soybean oil). crude soy oil. formulation.
or as lecithin. Lecithin also is used as a release
Additional processing steps are agent through its role as a surfactant.
available to obtain the necessary qual- Lecithin's edible nature makes it suit-
ity and characteristics for specific able for use on both cooked products
applications (see "Processing innova- (pan release), and release of food
tions," page 1164). products from conveyor belts in com-
mercial operations. Release agents
Applications also are used to prevent sticking in
"About 80% of the soy lecithin pro-
duced is sold (for use) as food emulsi- (conlinutd on pagt 1/62)

INFORM. Vol. 7. no. 11 (November 1996)


1162

LECITHIN

levels are sensitive to blood levels of


choline,
American Lecithin contends that a
100% PC supplement provides free
choline in the blood that passes the
blood-brain barrier and becomes
available for the manufacture of
acetylcholine. Other studies have
looked at the role of PC in regulating
digestive, cardiovascular, and liver
function.
The roles of choline and lecithin in
promoting health and preventing dis-
euse were discussed at the 7th Interna-
tional Congress on Phospholipids in
Brussels, Belgium. in September. One
prospect is the designation of a recom-
mended daily allowance (RDA) for
choline.
RDAs for vitamins and minerals
Lecithin i. Ju.1 one 01 many product. derived lrom processing toybean •. are set by the Food and Nutrition
Board in the United States. Several
nutrients important to health, such as
[continued from page. 1159) more blurred than it has been. Phos- choline and folic acid, do not have
pholipids are used in fields of geri- RDAs.
finished food products, such as cheese atrics, fat metabolism, neurology. and The phospholipid congress, spon-
slices. liver function, and also in treatment of sored by the AOCS Phospholipid
Also used as a biodegradable convalescent patients, arteriosclerosis, Division (international Lecithin and
release agent in many nonfood appli- and certain types of gallstone forma- Phospholipid Society) and several
cations, lecithin promotes easier mold tion. Research is continuing into companies, focused on the role of
release from several materials, includ- effects on memory, blood cloning, choline, lecithin, and other phospho-
ing plastics, resins. ceramics, roofing blood pressure, and vision. lipids in brain development and mem-
materials, and concrete. It also pro- Some of these medicinal uses, ory, decreasing the risks of heart dis-
tects the molds from rust and corro- however. are in the form of dietary ease and cancer, and cell functioning.
sion. supplements. Lecithin has been wide- According to Lucas Meyer, another
One of the largest nonfood uses is ly available as a retail dietary supple- phospholipid, phosphatidylserine
in calf milk replacers. where it serves ment, as capsules or granules. usually (PS). is essential to the functioning of
in emulsifying, stabilizing, wetting, containing less than 35% PC. If a all body cells but is most concentrated
and dispersing roles, Lecithin also higher PC content is desired, the in the brain. It is involved in a variety
functions as a substrate for enzymes lecithin must be fractionated. of nerve cell functions, including
added to the formula. Mixing deoiled lecithin with alco- nerve transmitter release and synaptic
Digestibility of nonmilk fats in hol will separate the lecithin into two activity.
calves is lower than that of whole- phospholipid fractions. While PE frac- Clinical studies have suggested that
milk fat unless lecithin is added. Even tions equally into alcohol-soluble and PS can support brain functions that
a lecithin content of as little as 2% insoluble portions, PC is alcohol-solu- decline with age. Lucas Meyer has
improves the digestibility of beef tal- ble and PI is alcohol-insoluble. Chro- spent seven years developing a pro-
low. coconut fat, and lard. matographic separation can then be cess to manufacture PS (found at less
used to prepare polar lipids of the than I % in lecithin) after investigating
Human nutrition highest purity. the evidence supporting its use as a
Phospholipids playa part in a wide The American lecithin Co .. wholly dietary supplement.
range of human metabolic processes owned by Rhone-Poulenc Rorer's "We've been marketing phos-
as well: fat absorption. cholesterol Cologne-based Nauermann Phospho- phatidylserine for about a year and a
metabolism. regulating serum lipid lipid GmbH, markets a 100% PC half now," said Susan Gurkin, director
level, fat transport. blood clotting, product. The company points to stud- of technical services at Lucas Meyer
nerve function. lung function, biosyn- ies that show the amount of PC pres- Inc" the U.S. affiliate of Lucas Meyer
thesis of prostaglandins, and vision. ent in the brain decreases after age 30. GmbH in Germany.
The line between nutritional and A better studied area is the use of PC "We're laking a different approach
pharmaceutical uses of lecithin and as a precursor for acetylcholine, a with PS:' Gurkin said. "We're taking
purified phospholipids is becoming neurctransmiuer. Brain acetylcholine the proactive approach of providing

INFORM. 'Yt>I. 7, no. '1 (NCNefTlber 1996)


1163

the information and educating con- PC and PE need to be in a specific somes sidebar on page 1166).
sumers rather than just selling the raw ratio for the emulsion to be stable. "There are two sides to our busi-
material." Phospholipids are also used to pro- ness: to supply phospholipids to the
Lucas Meyer plans to do the same duce liposomes. Liposomes are closed research community, and to supply
thing with PC next, Gurkin says, That spherical membranes that, in their bulk material to the pharmaceutical
would put them into competition with simplest forms, consist of internal industry, mostly for use as drug deliv-
American Lecithin's PC product, aqueous centers surrounded by two ery systems," said Walter Shaw, presi-
PhosChol. although they may not be layers of phospholipids. Again. a spe- dent of Avanti Polar Lipids.
offered through the same outlets, cific ratio of PC to PE (80:20) is need- According to Shaw. the first phos-
"Normally. our product won't be ed to fonn stable membranes. pholipid product to hit the drug deliv-
found in a majority of health-food According to Parnham, PC is the ery market was Exosurf, a lung surfac-
stores," said Randy Zigmont, presi- only phospholipid that forms Hpo- tant for neonatal babies. "This treat-
dent of American Lecithin. "It takes ment requires the very specific com-
an educator to explain to the consumer ponent of dipalmitoylphosphatidyl-
the difference between PhosChol and choline," Shaw said. "It won't work
an ordinary lecithin supplement." without it."
PhosChol is marketed by American Liposomes can do more than just
Lecithin directly through alternative deliver a drug. though. They can also
medicine providers. The company lessen the negative effects associated
markets the supplement for memory with drugs.
enhancement. liver protection. and "Phospholipids can serve to cover
cholesterol reduction, and also for up a toxic drug until delivered to the
antiulcer effects when used in combi- site of infection, by use of lipo-
nation with nonsteroidal antiinflam- somes," Shaw said. "Transporting
mation agents. drugs in phospholipid membranes or
As a finished consumer product, liposomes can lessen the side effects
PhosChol differs from other American of a drug."
Lecithin purified phospholipids that Shaw said no products are out yet,
are for use as raw materials in prepar- Powdered (left) and granular but gene therapy can be accomplished
ing pharmaceuticals. The company (rlghl) deoiled lecithin by associating a cationic lipid to the
also markets commercial-grade gene to be inserted. The lipid helps to
lecithin. camouflage the genetic material and
"Our mission is to develop purified transport it across the cell membrane,
phospholipids for use in pharmaceuti- according to Shaw.
cal, nutritional, and dermatological somes spontaneously in aqueous The pharmaceutical market is one
applications," Zigmont said. "Phos- media. All others require additional of the few remaining for uses of egg
pholipids in dermatological applica- stabilizing compounds 10 prevent the lecithin, which was identified long
tions increase the bio-avaitabillty of breakdown of the liposomal structure. before soy lecithin. The composition
drugs. enhance skin permeation. and Lipophilic ingredients can be of polar lipids and fatty acids in egg
stabilize active ingredients in topical embedded in the fatly regions between lecithin is different than thai in soy-
preparations." the phospholipid bilayer, while bean lecithin, which is advantageous
In pharmaceutical applications, hydrophilic substances are held in the in certain situations. Egg lecithin is
phospholipids can reduce undesirable aqueous internal space of the lipo- more expensive, however, and is
side effects of new and existing drugs. some. Multilamellar liposomes arc restricted by other issues as well.
he said. composed of more than one bilayer. "The FDA has questions about the
and can allow several compounds to viral control on egg lecithin. Viral and
Pharmaceuticals be compartmentalized. protein contamination From soybean
Phospholipids can serve as active Liposomes can be used in cosmet- lecithin are not thought to be a threat
ingredients in pharmaceuticals by hav- ics to carry moisturizers, sunscreens at this time," Shaw said.
ing an effect on biochemical metabol- or tanning agents. vitamins, or fra-
ic functions. or as adjuvants (aids) grances. The main use to dale has Agricultural chemicals
because of their physical-chemical been for skin- and hair-care products. Liposomes also could be used in agri-
properties. Active ingredient research but the hottest growth area is for med- cultural chemicals. to promote the
has focused on pc, although there is ications. The body absorbs some med- mixing of compounds that otherwise
interest in other phospholipids. ications more readily when they are might be incompatible. The structure
As adjuvants. phospholipids are administered in liposome form. Lipo- of liposomes also could be valuable
used as emulsifiers for intravenous somes can be targeted for specific for applying pesticides because of the
infusion solutions, known as parenter- organs. to deliver the drug directly to structural similarity to biological
al solutions. For parenteral solutions. the site it is designed for (see lipo- membranes.

INFORM, Vol. 7. no. II (November 1996)


1164

LECITHIN

Field trials have been conducted on


the effectiveness of using lecithin in
agricultural chemicals as both a carri-
er (adjuvant) and diluent. According
to Johnson, at least four years of
industry data show lecithin works bet-
ter than soybean oil and costs Jess
than comparable petroleum-based
products.
"There is no incentive for chemi-
cal manufacturers to change (from
the petroleum-based products),"
Johnson said. The efficacy of the
active component is improved, which
would lead to lesser rates of applica-
lion, so the manufacturer would sell
less product.
Johnson concedes that farmers
lack incentives to become lecithin
promoters. "Since lecithin is such a
LecIthIn quallty cen be affected by aoybean growth lind development, as well !III atorage small pari of the soybean product,
and proclsslng. growers are not pushing it," Johnson
said. "The lecithin producers are

Processing innovations: from bean to modified lecithin


liitK;:;:i~iilchange
"I think we are going to see a major
in the oil industry, due to
The lecithin produced is free of oil, with a phopholipid
composition comparable to lecithin deoiled with acetone.
changes in processing technology," Although these new ideas in lecithin extraction may
said Roger Sinram, industry con- involve new technology, the least expensive way to get
suuant. 'There is a push to cut back lecithin out of soybeans is still the tried-and-true method
on the amount of hexane used in that has been used for decades. New methods may have
processing. for example." made it as far as laboratory testing or even pilot-plant
Although most soybean proces- scale, but a significant cost reduction or increase in prod-
sors have been using the same tech- uct quality must occur before companies will switch over.
L.:======:J nology for many years to extract
lecithin, there have been some recem innovations, such as
"While we have looked at various lecithin extraction
technologies, 10 date we have elected instead to invest in
the five described here. improvements at other points in our soy processing oper-
One extraction option being proposed is degumming in ations where changes may have more of an impact," said
the miscella. Lecithin could be separated out by using Don McCaskill, director of the research and technical
membranes with pores large enough to allow flow of oil center at Riceland Foods Inc .• a farmer-owned co-op
and solvent but small enough to restrict the phospholipids. based in eastern Arkansas. "We believe our new
Lucas Meyer experimented with membrane materials and dehulling system, for example. will give us more long-
found that plastics may swell and decrease the size of the term benefit for the cost involved."
pores. Ceramic membrane filters are not susceptible to Not all phospholipids are removed from soybean oil
swelling and perform beuer in phospholipid separation tests. during water degumming. One proposed alternative in
"Membrane technology may even eliminate the refiner this area involves using the phospholipase A2 enzyme to
step for soy oil," said Bernie Szuhaj, director of research hydrolyze the nonhydrntable phospholipids (NHPs) after
and development for Central Soya. Micropore membrane soy oil has been degummed with water. This creates a
technology could possibly be used to separate the various Iysophospholipid that can be hydrated with water and
phospholipid fractions in lecithin, according to Sinmm. thus removed from the oil by centrifuging.
Another proposed separation technology is to degum While proven in a laboratory setting, this technology
soy oil with compressed gases. such as carbon dioxide or is not currently scheduled for use in lecithin production.
propane. Propane does ncr react with lecithin. and could be It is also more of interest to oil producers. to reduce
recovered at room temperature and pressure. Lecithin phosphorus content in the oil. than to lecithin producers.
would be recovered as a wet sludge by centrifuging the oil. The more common method of removing NHPs is to

INFORM. Vol. 7. no. 11 (November 1996)


1165

morc responsible than soybean grow- being incorporated in 1990," Gurkin ed States. but has been legal in Europe
ers for any growth in the lecithin said. for years.
market:' ILPS is working toward standard-
According to Johnson, there is also ized methodology for the lecithin Aquaculture
a significant difference between industry. According to Gurkin, the One bright spot for lecithin use around
research on soybeans and research on European Union recognizes a tolu- the world is aquaculture. Research
lecithin. Government funding for lene-insoluble test vs. the familiar into marine animal feeding has found
lecithin research is virtually nonexis- hexane-insoluble test in the United that three related dietary factors affect
tent, Johnson said. States. The ILPS plans to evaluate all the growth and mortality rate of
"Most research in lecithin has been methods and come up with sugges- shrimp and other crustaceans: phos-
by the companies that have a vested tions as a foundation for world stan- pholipids in the diet, choline in the
interest," said Roger Sinram, industry dards. diet, and the proper absorption of
consultant. Another difficulty is with European cholesterol.
approval of modified lecithin as food "Phospholipids are a dietary essen-
Standards ingredients. Hydroxylated lecithin has tial for marine crustaceans, and
Another area of difficulty is in indus- been approved for food use in the enhance growth and survival of fish
try standardization. Nomenclature and United States for years, but is not cur- larvae," said Chhorn Lim, a U.S.
test methods are different around the rently allowed in Europe. A specific- Department of Agriculture fish
world. use petition would be needed to get research specialist.
"Establishing consistent termi- approval for use of hydroxylated Lecithin as an ingredient in crus-
nology was one of the main issues lecithin in Europe. Lecithin treated tacean diets can address these nutri-
leading to the International Lecithin with enzymes is now "generally rec- tional issues, and also playa function-
and Phospholipid Society (ILPS) ognized as safe" (GRAS) in the Unit- al role by acting as an antioxidant, a

treat the soybean oil with acid (usually phosphoric or cit- triglyceride oils, or surfactants. Complexed lecithins
ric). Acid treating may change the composition of the (blends of lecithin in vegetable oil) are used as release
lecithin, however, by increasing the amount of phospha- agents for process equipment in food manufacturing.
tidic acid and decreasing the yield of PC, PE, and PI. Other possible modifications of lecithin involve acety-
The level of NHPs also can be reduced by applying lation. hydroxylation, hydrolyzation, and hydrogenation.
heat to the soybeans before the extraction process. This Acetylation involves a chemical reaction between PE and
inactivates the Jipoxygenases and phospholipases acetic anhydride, which results in water dispersible N-
believed to cause NHPs during extraction. Tests conduct- acyl-PE and acetic acid. The N-acyl-PE helps the remain-
ed by Lucas Meyer GmbH & Co. of Hamburg, Gennany, ing unreacted lecithin components to disperse readily in
have shown that soybeans receiving this treatment yield water.
twice the lecithin as do untreated soybeans, with a higher Hydroxylation involves hydrogen peroxide reacting
PC content as well. Overheating the soybeans, however, with the fatty acid carbon-carbon double bonds to form
can increase the level of NHPs. two hydroxyl groups at the double-bond sites. Hydroxy-
luted lecithin is more suitable for oil-in-water emulsions.
Beyond crude lecithin Hydrogenation of lecithin, on the other hand, adds hydro-
Once extracted, lecithin can be processed further by stan- gen to the carbon double bonds, giving greater oxidative
dardizing, modifying, or fractionating. Simple refining stability and reduced solubility.
steps clarify and remove impurities, but the more important In lecithin hydrolysis, the same phospholipase A2
standardization of lecithin lowers the viscosity and creates a enzyme that can be used to hydrolyze NHPs left in soy
uniform product with a specific phospholipid blend. oil is used to selectively cleave the j3~position fatty acid
Another processing step, deoiling, occurs when from lecithin. This terms Iyso-lecithin, which reacts ran-
lecithin is mixed with acetone, and acetone-insoluble domly with all phospholipids. Hydrolyzed lecithin is also
phospholipids are extracted, filtered, and dried. Deoiling effective for oil-in-water emulsions.
separates neutral lipids from polar lipids, leaving a more From raw lecithin extraction to later refining and mod-
reactive lecithin, which enhances the bonding with carbo- ifying steps, the processing of lecithin is ripe for innova-
hydrates or proteins. tion. "Enzyme-modified lecithin was the last innovative
Lecithin can be modified in several ways. Compound- product to be marketed" said Frank Orthoefer, industry
ing combines lecithin with monodiglycerides, emulsifiers consultant. "Little has been added to commercial pro-
such as glycerol polyelhyleneglycol ricinoleate, dilutions cessing in the last 10-15 years. New separation tech-
with special oils such as sunflower or medium-chain niques have only recently been discussed."

INFORM, Vol. 7, no. II (NCNefTlber 1996)


1166

LECITHIN

binding aid, and by reducing leaching Yet in the United States, catfish not thrown away, but sold at a dis-
of feed components, according to production will have jumped tenfold count as soapstock. a mix of soy oil
Orthoefer. from 1980 levels if predictions of 345 residues derived from caustic refining,
According to the United Nations MT by 2000 prove correct. U.S. aqua- or added back to the soybean meal,
Food and Agriculture Organization culture is on the rise, which means where its caloric value increases the
(FAG), aquaculture is one of the that the market for fish and crustacean meal value.
fastest growing food production activ- feeds is also expanding. "It is capital-intensive to separate
ities in the world. In 1994 (the latest "Much of the aquaculture feed lecithin, and some are forgoing it
available FAD data), fish and shellfish industry now uses lecithin concen- (separation) to throw all of the gums
production grew over two million trates," Onhoefer said. into animal feed," Sinram said. "The
metric IOns (MT), a leap of 13% over "Aquaculture is indeed an exciting processing, handling, separate tank-
1993 figures. field to watch," said Lance Colbert, age, and logistical hassles make it
Global aquaculture production of manager of lecithin technical services (lecithin recovery) not worthwhile for
fish, crustaceans, and mollusks has at Archer Daniels Midland (ADM) many, given that crude lecithin may
more than tripled since 1975. and is Lecithin, which has an aquaculture fetch only 40 cents (a pound) com-
expected to rise to 21 million MT by center for research and production. pared to getting 10 cents for the gums
2000 and 62 million MT by 2025. "We expect this use of lecithin to to be used in feed."
Most of that growth. however. is increase." These factors play a role in
occurring outside the United States. lecithin's growth prospect.
Asia continues to lead global aquacul- The future "Worldwide lecithin supplies are
ture efforts, with China, India, Japan, The lecithin industry has room to growing 1-2% faster than demand
Korea, and The Philippines combining grow. According 10 Charles Worrall, each year. so worldwide stocks are
to account for approximately 80% of marketing manager for Central Soya, gradually increasing," Worrall said.
the total. In 1994, aquaculture produc- at present only 40% of the gums in "Demand for value-added products is
lion of fish and shellfish in China con- soy oil are convened into lecithin. In growing much more quickly."
tributed over 50% to that country's essence, the lecithin market would Value-added lecithin products may
total national fishery production. far have to double to utilize current or may not be a part of your soybean
more than the United States. where potential production capacity. processing business, depending on
less than 7% of total domestic fish How could over half of potential where you are located. "Unlike Europe,
production was from aquaculture lecithin production be thrown away? North American lecithin companies
operations. The answer lies in the fact that it is tend to be integrated with the proces-

Liposomes may be route to higher-value uses


rJi[i~:;,~~il One hurdle to expanding the lipo-
some market is that purifying phos-
pholipids is expensive. Competing
and CEO of American Lecithin Co. "Any process that
has a I: 10 ratio of product 10 raw material will be costly.
No matter how you look at it, it's going 10 be expensive."
methods of making active ingredi- Yet the co-products are not worthless. According to
ent carriers are to use other materi- Zigmonl, they can be blended back in with other lecithin,
als to make liposomcs, or even use but they also have unique properties in their own rights.
other carriers entirely. "For instance, PE has been shown to exhibit antioxi-
"The cost of fractionation is still dant properties," Zigmont said. "Products derived from
an issue, as there is a low level of the by-products (PE and PI) have been shown to increase
L " demand," said Walter Shaw, presi- yield value in chocolate manufacture."
dent of Avanti Polar Lipids. "As The limited size of the lecithin market, combined with
demand increases, production capacity increases and the few companies working the field, leads to frequent busi-
price will decrease. So as the market grows, prices will ness partnerships, For instance, Stern Lecithin & Soja
become competitive." has the responsibility for selling the by-product and food
Incorrectly judging the size or timing of the market fractions from Nattennann Phospholipids processing in
may be enough to sink even the best marketing plans. "I Europe. Central Soya has those rights for the rest of the
know of some in this industry that invested heavily in world market.
large-scale production and have lost everything," Shaw Another issue holding back phospholipid-based lipo-
said. "h is a real balancing act." somes is their stability in cosmetics formulations. Llpo-
"One reason the cost is high is that for every kilogram somes based on other materials or nonliposome polymer-
of PC you make from lecithin, you generate nine kilo- ic capsules can duplicate the feats of liposomes without
grams of by-product," said Randy Zigmont, president the restrictions placed on phospholipids.

INFORM. Vol. 7. no. 11 (November 1996)


1167

sors that separate the soy oil from the fiers. Still, lecithin is often used as a exporter, and the European Union a
gums," Worrall said. "Many of these co-emulsifier by virtue of helping other net importer, by roughly the same
companies produce value-added emulsifiers work more efficiently. amount. South America and the Far
lecithin products that extend the func- "Modified lecithins work well in East produce smaller amounts." In
tionality of the commercial grades." paints, but so do other things," Sinram Europe, much of the lecithin for use
The world lecithin market, includ- said. "It will take education, market- in fractionating is purchased from
ing all lecithins-all uses, standard- ing, and advertising to provide any the United States, because of the
grade through value-added prod- momentum away from traditional quality and consistency of U.S. pro-
ucts-is 150,000-160,000 MT, solutions." duction.
according to Worrall. Some in the "A major growth area in lecithin ADM claims to operate the world's
industry have suggested that up to use is the aquaculture market, initially largest lecithin production facility at
120,000 MT of the IOtal is standard- using granular or deoiled lecithin," Europoort, The Netherlands. Other
grade lecithin. Orthoefer said. "Shrimp aquaculture lecithin companies associated with
"Standard-grade lecithin is the has been growing at more than 35% ADM in Europe are Ohlmiihl Ham-
workhorse of the industry," Colbert per year." burg and Soya Mainz.
said. "On a percentage basis, it is our "We are constantly looking for new No rnaucr where or how it is made.
best-selling product:' niches," Colbert said. ADM is even lecithin will still have a place in the
Finding new uses for commercial- building a new lecithin deoiling plant, world today.
grade lecithin is no small task because based on expected sales. "Lecithin is our lowest cost emulsi-
lecithin has been on the market since Central Soya. one of the largest fier available now," Orthoefer said.
the 1950s, so the market is relatively lecithin producers in the industry, has "As far as price vs. functionality is
mature. a partnership agreement with Stern concerned, lecithin is our best alterna-
"Expansion of the standard lecithin Lecithin and Soja GmbH. Europe's tive."
market has been slow recently," Col- second largest marketer of lecithin. From roadways to car wax, from
bert said. Stern and Central Soya both are dietary supplements to aquatic feeds,
Enticing potential users to switch owned by the European firm Eridania lecithin and purified phospholipids
from what they are using and to try Beghin-Say. will continue to fill roles with a
lecithin is a difficult task at best. If "Both the United States and unique blend of benefits compared to
lecithin gets too expensive for a partic- Europe are major lecithin producing cost required.
ular application, users can often substi- regions of the world," Worrall said. "The future continues to be bright
tute mono- or diglycerides as emu lsi- "The United States tends to be a net for lecithin," Orthocfer said.

"Phospholipid stability in formulations is still an issue up more of a hydrophilic drug," Shaw said. "Some charged
of concern," Shaw said. "There are a couple of ways to ltposornes can bind specifically to cell walls or to proteins."
get around this problem. First, you can move from natu- Yet there will always be resistance to change. "In
ral products 10 synthetic variations. This allows you to the liposome area, phospholipids are competing against
control the number of double bonds rather than just take existing technology that may be cheaper and more
whatever nature gives you." entrenched," said Roger Sinram, industry consultant.
According to Shaw, synthetic phospholipids are mere- Liposornes have some advantages, however, that can-
ly natural phospholipids where the fatty acids have been not be duplicated by alternative carriers. "There are com-
rearranged on the glycerol backbone. This creates a spe- peting drug delivery vehicles, but phospholipid lipo-
cific profile that determines the physical properties of the somes are natural products--even the synthetic variations
molecule. of them-so 10 metabolize them is easy," Shaw said.
"Second, ester bonds in the presence of water will "Others (drug delivery systems) are not necessarily based
hydrolyze:' Shaw said. "ln that case, the hydrolysis can on natural materials, so metabolism becomes problemat-
. .,
be limited by using a lyophilized formula and limiting
exposure 10 water. A phospholipid can be shipped as
". Although injectable drug delivery has become the
powder, and then sterile buffer is added on site to pro- leading research area for lipcsomes. there are other
duce liposomes when needed." applications receiving increased scrutiny. "Liposomes
Another factor with liposomes is the limited quantity of are not restricted to drug delivery, but can be used in
lipophilic and hydrophilic materials that can aggregate in foods as well," said Bernard Szuhaj. director of research
the bilayers and in the core, respectively. "Liposomes can and development for Central Soya, "Central Soya is
be given a negative charge, which forces open a wider focusing on food uses, including adding flavors with
space in the center of the liposome. allowing them to take liposomes."

INFORM. VOl. 7. no. 11 (November 1996)


1168

LECITHIN

The importance of phospholipid terminology


The name "lecithin" was first used by
GobJey in 1850 (I) to describe an
extract of egg yolk (Greek lekithos)
from which Diakonow (2) subsequent- This article by Michael J. Parnham, Pomhmn Adviser
ly isolated phosphatidylcholine. Since ry Services, Van Guericu AUee 4, 0-53125 Bonn,
that time, "lecithin" and "ph os- Germany. and Phannacoiogical11lStihlle for Life sci-
pharidylcholine" frequently have been entists, Goethe Unil'ersity Franlifun. 0-60439 Frank·
used interchangeably. fun. Germany, is based on his presentation during the
The IUPAC-JUB (International 87th AOCS Annual Meeting & Expo
Union for Pure and Applied Chem- held earlier this year in Indianapolis. lndiana.
istry-International Union of Biochem-
istry) proposals for the nomenclature of
lipids provide a systematic definition of
the chemical structures of pure phos- obtained from animal, vegetable or Current international lecithin speci-
pholipids and propose a shorthand microbial sources, containing a vari- fications
nomenclature which has found increas- ety of substances, such as sphingo- Commercial lecithin usually is
ing acceptance in the biochemical liter- sylphospholipids, triglycendes, fauy extracted from soybeans or from egg
ature (3,4). According to this nomen- acids, and glycolipids" (6). This def- yolk. Crude soya lecithin contains
clature, 3-511 phosphatidylcholine (Ptd inition covers the wide variety of 52% mixed phospholipids of which
Cho) is the recommended name for natural and refined lecithin products 12-18% is phosphatidylcholine.
I ,2~diacy l-sn-glycerolt Sjphospho- commercially available, but does not Oeoiling with acetone generates a
choline (acyI2GroPCho) (3). The old indicate the relative proportions of granular product containing 78%
trivial name of "lecithin" is neither rec- the different components, nor does it mixed phospholipids (20-95% pbos-
ommended nor does it offer any advan- define the purification stage of the phatidylcho1ine) which on further
tages over the IUPAC-IUB nomencla- product. Furthermore. the ILPS defi- extraction with ethanol can be frac-
ture (3-5). nition of lecithin clearly would not tionated to yield high concentrations
However, outside biochemical cir- include a synthetic or semisynthetic of phosphatidylcholine (7) (Table I).
cles, the term "lecithin" still is used product. Specifications regarding purity gener-
widely, frequently without clear defi- The current regulatory specifica- ally reflect the need to limit solvent
nition of what chemical entities the tions for lecithin and the problems contamination as well as the presence
term is intended to cover. The Inter- arising as a result of different con- of toxic heavy metals and perox.ides.
national Lecithin and Phospholipid stituents with varying biological activ- The result is that there is little global
Society (ILPS) has published the fol- ities will be reviewed briefly and pro- standardization of the actual con-
lowing definition for lecithin: "a posals made for clear and effective stituents and physical properties of
mixture of glycerophospholipids terminology. commercial lecithin. This stands in

Table 1
Commercial phospholipid fractions from soya beans and their use

TYPe Content U,.


Crude lecithin Milled phospholipids 52% Industrial lubricant,
(phosphatidykholine = 12-18%] emulsifier
Oillfats 35%
Olycolipidslsugarslothen 13%

Deoiled lecithin Milled phospholipids 78% Emulsifier in foods,


[phosphatidylchcline = 20-25%] bread dough stabilizer
01ycolipidsloillfatslothers 22%

Ethanol-soluble Milled phospholipids 85% Emulsifier in foods.


fraction [phosphatidylcholine = 40-53%] (e.g.. chocolate)

Purified phospha- 80-100% Excipient. liposomes, milled


tidylcholine micelles, active ingredient
in cosmetics, emulsifier in
phannaceuticals

INFORM. Vol. 7. no. 11 (November 1996)


1169

Table 2
U.S., British, Japanese, and European specifications for purity of commercial lecithin

USP XXUJ Merck 1'322 ISCI·II


NFXVII Index and EFEMA
Monogruph rcc ru + HPE (11th)
Definition Lecithin Lecithin Lecithin Lecithins Hydrolyzed Soybean
vegetable lecithin phospholipid
Acetone-
insoluble
;<!:50% ;<!:56%
matter

Hexane-
>50%
""""
insoluble
matter ~.3% ~.3% :SO.3 Q
~.3%a :SO.3%

Volatile
matter <2%' s2 ... ""%

",0 S1.5% S1.5% <2% <2% ""%

A. 3 ppm 3 ppm 3 ppm 3 ppm 2 ppm

Pb SlOppm :SIO ppm SlO ppm :SIO ppm

Heavy metals 40 ppm 40 ppm 50 ppm 50 ppm 20 ppm

Peroxide
value SIOO SIO SIO slO

Acid value S3. <3. 20-30 <35 <45 S40

Iodine 95-100 95
value (liquid)
82-88
(gran.)
Packaging well- well-
"d closed closed
storage containers containers
a Totuenc.inso-luble.
bA1HWCfor t h.

marked contrast to purified phos- triglycerides, fatty acids, and carbohy- 2). These specifications also are given
phatidylchcline which is usually well- drates in varying proportions. The in the Handbook of Pharmaceutical
defined with regard to source. chemi- specified product contains 90% or Excipients (HPE) published jointly by
cal composition, and physical proper- more of phospholipids of differing the American Pharmaceutical Associ-
ties. grades, forms. and color. In contrast, ation and The Pharmaceutical Society
The lecithin specifications of the the Food Additives Handbook (9) of Great Britain (II), which defines
Food Chemicals Codex (FCC IrQ (8) describes lecithin simply as "a com- lecithins from both plants and eggs.
are given in Table 2. The product to plex mixture from soybeans, and other The Merck Index (12) specifies a
which these specifications refer is plants." without reference 10 its con- slightly lower acid value (Table 2).
defined as food-grade lecithin from stituents, stating only that in oleomar- The Japanese Monograph (lSCI-IIJ
soybeans and other plant sources con- garine it is limited to 0.5%. (13) specifies a lower heavy metal
sisting of a complex mixture of ace- The US Pharmacopeia (USP XXII) content.
tone-insoluble phospholipids (mainly or National Formulary (NF XVII) The European Community specifi-
phosphatidylcholine, pbosphan- (10) also provides a similar descrip- cations (Guideline 78/664IEWG) for
dylethanolamine, and phosphatidyli- tion 10 that of the FCC III, though lecithins (E322) (14) are also included
nositol) combined with various without defining the phospholipid in the Monographs far Emulsifiers for
amounts of other substances such as content or the peroxide value (Table Foods (2nd Edition] of the European

INFORM. Vol. 7. no. 11 (November 1996)


1170

LECITHIN

Table 3
Specifications for commerclallecfthln In German-speaking countries

Monograph DAB 7 OAB Pharmacopeia Hager's


Helvetica (PH 6) Handbook

Definition Lecithin Lecithin Lecithin Lecithin Lecithin


(egg) (plant) (soy) (soy) (egg)
Peroxide value S5 <5 <5
Acid value :S3 mLb
Volatile matters S5% $3% S2%
Sulphonate ash <9% 4-7% 4-7%
Phosphate ,,% ,,% ,,% 3.6-3.9% <3.8%
Nitrogen 1.7-2.0% 1.7-2.0% 1.7-2.0% 1.7-2.0% 1.7-2.0%
Iodine value 55-65 70-90 65-105 94-99 64-70
Packing and storage Well-closed, Well-closed, Well-closed,
light-protected light-protected light-protected
containers containers containers

~ AI IOSOC for I h.
b Vol. orO.IN NtOH rorOS Ilccilbin in 10 mL ethanol.

Food Emulsifier Manufacturers Asso- 3 ppm for arsenic and 50 ppm for Office (LSRO) of the Federation of
ciation (EFEMA) (15). These differ in heavy metals in agreement with the American Societies for Experimental
some respects from the U.S. specifica- E322 specifications. The German For- Biology reviewed the use of lecithin
tions. E322 distinguishes between eign Substance Commission obtained from plant sources as a
lecithins (which may be from plant (Deutsche Fremdstoffkommission) human food ingredient (22). and on
sources or from eggs) and hydrolyzed (20) recommends an acid value of not the basis of the LSRO report, the FDA
lecithins. The latter are permitted a more than 4%. Hager's Handbook subsequently issued new regulations
higher acid value and somewhat lower (21) quotes the purity specifications (21 CRF 1841400) affirming the "gen-
content of acetone-insoluble matter given by the USP XXII and the erally regarded as safe" (GRAS) status
than nonhydrolyzed lecithin, though OAB81, but also distinguishes of plant-derived lecithin (23). (It is
both European specifications for ace- between lecithin from egg and soy- pertinent to the present article that the
tone-insoluble matter are stricter than beans. The latter is defined as contain- LSRO report drew attention to the fact
those of the Federal Drug Administra- ing approximately 95% phosphatidyl- that the interchangeable use of the
tion (FDA) (Table 2). This also choline and <1% other phospholipids, terms "lecithin" and "phosphatidyl-
applies to the specification for the per- while egg lecithin is defined as con- choline" "has created confusion," rec-
oxide value, though the U.S. specifi- taining approximately 94% phos- ommending that the trivial name
cations marginally are stricter with phatidylcholine and <2% other phos- "lecithin" be restricted to the commer-
regard to water and heavy metal con- pholipids; fatty acid ranges are also cial product.) When it is used in low
tent. E322 also specifies that the given. For both lecithins, Hager's concentrations as an emulsifier,
lecithin should contain not more than Handbook provides slightly differing lecithin's GRAS status covers any
2% volatile matter by drying at 105°C phosphate contents and distinct iodine potential biological effects of com-
for one hour. This presumably is due values. mercial lecithin. However, when high-
to the very different specifications for The broad differences in interna- ly purified components of lecithin are
pharmaceutical use' in German-speak- tional specifications also stem from used in larger doses as nutritional sup-
ing countries (Table 3). different traditions in the applications plements or as drugs, the biological
These are predominantly based on of commercial lecithin. On the one activity of the product becomes much
coloring and ashing procedures. In all hand, the product as a crude prepara- more relevant. In this case, specifica-
three countries [Germany (DAB), tion may be used as an emulsifier in tions for limitation of impurities must
Austria (ClAB). and Switzerland (PH foods and, on the. other hand, as a be complemented with definitions
6)] the nitrogen content is specified as highly purified, biologically active which reflect the desired biological
1.7-2% and the phosphate content as pharmaceutical-grade phosphat idyl- activity, and this may vary depending
at least 3% (16-18). In Germany (16). choline. on the constituents.
arsenic and heavy metal content are It is at the level of application that
not specified, but the German Regula- a differentiation in terminology is Distinctive biological activities of
tions for the Use of Additives required initially. On the basis of an phospholipids
(Deutsche ZusatzstojJverkehrsverord- assessment of the literature since Nutritional use. Lecithin is used both
nung) (19) recommends maximums of 1930, the Life Sciences Research as an emulsifier in processed foodstuff's

INFORM, VOl. 7. no. 11 (November 1996)


1171

Table 4
Fatty acid composition of soya and egg lecithins, %"

Fatty acids Soya ledthin Egg lecithin


Kirk-Othmer Hager Klrk-Othmer Hager
(Ref. 27) (Ref. 20) (Rer.27) (Rer.20)

Palmitic acid C16:0 18.4 16-20 37.0 39-47


Stearic acid C18:0 4.0 9.0
Oleic acid CIS:I 10.7 8-12 32.3 28-32
Linoleic acid C18:2 58.0 62-66 16.7 13-17
Linolenic acid C18:3 6.8 6-8
Arachidonic acid C20:0 5.0 J-<j

O",,~ 2.1 0 1-2


a I'b<:mcqe ollOlal flU)' Kid eonItfIl.

and in high concentrations as a nutri- tional supplement. As with parenteral tiona! supplement. However, me main
tional supplement. As an emulsifier, nutrition, oral dietary administration nutritional value of lecithin is as a
the specific proportions of the phos- of egg lecithin results in a higher plas- source of choline. The LSRO report
pholipids in the lecithin are not crucial ma cholesterol concentration than (23) reviewed some of the early stud-
because it is the physical surfactant does comparable dietary soy lecithin ies on the neurological effects of
property of the lecithin, not biological (28). indicating that soy lecithin is dietary soy lecithin and phosphatidyl-
effects, which is of importance for the preferable to egg lecithin as a nutri- choline. Subsequent investigations
preparation of emulsions (24).
A caveat, however, should be drawn
for the use of purified lecithin as an
emulsifier in fat emulsions for par-
EDIDLE OIL PROCESSING
enteral nutrition. Generally speaking,
purified egg lecithin is used for this
purpose in North America, and puri-
fied soy lecithin has been utilized
widely in Europe. ln a series of com-
parative investigations of fat emulsions
prepared with either egg lecithin
(Intralipid) or soya lecithin (Lipo-
fundin) as emulsifier, it was found that
lntralipid increased the concentration
of triglycerides in plasma very low
density lipoproteins (VLDL), whereas
Lipofundin lowered VLDL triglyc- NATURAL
eride concentrations (25,26). This dis- VITAMIN E PLANTS
tinction can be attributed to the higher
content of polyunsaturated fatty acids If you wish to concentrate your Vegetable Oil Refinery
(PUFAs) in purified soy lecithin, as
Distillate to increase sale value or to manufacture Nlltural
compared to purified egg lecithin Vitamin E, we have the technology.
(Table 4). An increase in VLDL
triglyceride content is undesirable in We are also specialist in Oleo ~ie.1s ofF.tty Acids.
patients at risk for hypercholes- FattyAmiTIes and other derinti\'CS. Please enquire for full
terolemia and atherosclerosis (23). so process range olTered. We supply packages from simple
that in such patients receiving long- update of I:Xistingplant through to full plant design or
term total parenteral nutrition, the know-how only
choice of egg or soy lecithin as an
emulsifier may have clinical relevance. ABLE CHEMICAL & ENGINEERING DESIGN LTD
It should be noted that both types of THE LODGE. NEW MILL., PARK ROAD.
lecithin require purification for use in DUKINFIELD. CHESHIRE SK16 5LL. UNITED I(INCDOI't1
parenteral nutrition. in order to remove J'bon,t UK 161 ~J 1771, .. _. UK 16. JJU 71U4

hemolytic phosphatidic acid. For Information cIrcle 1100


Lecithin is sold widely as a nutri-

INFORM VOl, 7, no. 11 (Ncwembell996)


1172

LECITHIN

Table 5
Fatty acid composition of different soya phospholipid classes (%)'"

Fatty acids Phosphatidyl- Phosphatidyl- Phosphatidyl- Phosphatidic


choline ethanolamine Inositol acid
Palmitic acid C16:0 20.5 31.6 47.7 34.0
Stearic add CIS:O 5.5 3.2 8.2 8.1
Oleic add CIS;) 10.5 8.7 4.9 11.9
Linoleic add C18:2 58.8 53.2 36.2 44.7
Linolenic acid CIS:3 4 .• 3.2 2.8 1.3

Q Pen:enlll3C oflO11I1fally acid CQf1tent.Reference 49.

have confirmed the importance of (Iiposomes) spontaneously in aqueous Pharmaceutical usc. Purified phos-
dietary lecithin as a precursor of media. All other phospholipids require pholipids from natural sources.
choline and have demonstrated benefi- the addition of other stabilizing com- together with semisynthetic and syn-
cial effects of dietary lecithin when pounds to prevent the breakdown of thetic phospholipids, are employed as
administered to elderly patients with the liposomal structure. There is pharmaceutical excipients and drug
some neurological diseases. particu- increasing worldwide pressure to carriers. as well as forming the active
larly tardive dyskinesia (29.30). In this reduce the safety testing in animals of ingredients of various pharmaceutical
respect. it is not lecithin as a mixture cosmetic ingredients. and within the products administered orally, topical-
of phospholipids which is of value. European Union such animal testing is ly. or parenterally. As an excipient. for
but specifically phosphatidylcholine. actively discouraged (33). Conse- example for parenteral diazepam. soy
In order to relate neurological effects quently. the GRAS status of lecithin lecithin is used in the form of mixed
to the dose or dietary intake. it is usually is invoked to account for the micelles with bile acid to improve sol-
essential that the phosphatidylcholine safety of phospholipids for cosmetic ubility and reduce local irritancy (36).
content of nutritional supplements be use and to obviate toxicity testing. In this respect, it is once again the
clearly stated. However. phospholipids differ in physical properties of the phospho-
Phosphatidylcholine and choline their biological effects on the skin. lipids that are most important. so
are not only of importance for the Moisturizing or hydration of skin is therefore the content of specific phos-
neurological health of the elderly. The achieved by modifying the lipid con- pholipids is not crucial. The relatively
plasma of newborn infants has a much tent of the horny layer (strauon small amount of product administered
higher choline concentration than that cornea). Administration to normal makes the biological distinction
of adults (31). Human breast milk human skin of a liposomal dispersion between soy and egg lecithin-as
within the first few days of lactation containing 80% phosphatidylcholine. described for parenteral fat emul-
contains high concentrations of both 9% phosphatidic acid. and 4% N- sions-irrelevant. However, use of
free choline and other choline-con- acetylphosphatidylethanolamine pro- saturated. rather than highly unsaturat-
taining lipids. including phosphat idyl- duced a 38% increase in skin humidity ed. soy phospholipids for the prepara-
choline (32). It has. therefore. been (34). Decreasing the phcsphutidyl- tion of mixed micelles enhances floc-
argued that infant formulas should choline content and increasing the culation and decreases the excipient
contain adequate concentrations of phosphatidylinositol content of the efficacy of the mixture (37). Conse-
various forms of choline. including Iiposomes ultimately resulted in a dry- quently. even as an excipient. a defini-
phosphatidyJcholine (not just lecithin). ing. rather than a moisturizing, effect tion of the degree of saturation of the
to meet the infants' dietary require- on the skin. Soy phosphatidylcholine. lecithin used is needed.
ments (32). Once again. the use of with a high content of PUFAs. which Phospholipids also are the basic
lecithin as an emulsifier in infant for- are required for healthy skin. may con- building blocks of liposomes as drug
mulas necessitates definition of the tribute toward the regulation of epider- carriers. A wide variety of different
proportion of phosphatidylcholine that mal proliferation (35). types of phospholipids. together with
is present in order to relate this 10 These effects, while not limiting additional charged constituents, pro-
potential biological effects. the dermal safety of phospholipids. teins. and cholesterol are formulated
Cosmetic IUC. The major use of certainly emphasize that the terms in liposomes to enhance organ and
phospholipids in cosmetics is in the "phospholipids," "lecithin," or "lipo- tissue targeting or to modify transport
preparation of liposomes. These are somes" are insufficient to define capacity (38,39). Quite apart from the
either used per se as skin moisturizing potential or expected effects on the fuct that additional charged con-
agents or as carriers to facilitate skin skin. For this reason. it is necessary to stituents and proteins can exert their
penetration of other cosmetic ingredi- define the actual content of specific own biological effects. the liposomal
ents. Phosphatidylcholine is the only phospholipids in products applied as formulation of different phospholipids
phospholipid which forms vesicles cosmetics. is not without biological repercussions

INFORM. VOl. 7. no. 11 (Novembef 1996)


1173

Table 6
Summary of the comparative properties of commercial lecithin and purIfied phosphatidylchollne

Lecithin Phosphalidylcholine
Specifications Variable mixture of phospholipids Chemically defined
and other constituents

Nutritional use Cheap emulsifier; degree of Standardized degree of saturation;


saturation affects blood lipids; more expensive: standardized source
variable source of dietary choline of dietary choline and PUFA
Cosmetic use Inappropriate Defined moisturizing effect;
skin penetration control
Pharmaceurical use Needs purification: degree of Defined excipient; forms liposomes
saturation affects micelle spomcneocsty« Purified from soybeans. used
formation to treat mild hypercholesterolemia and liver injury
at appropriate dosages

(40). For instance, the more saturated phatidylcholine has the highest pro- tion not only leads to confusion but
the phospholipid the greater is the len- portion of PUFA subsrltuems (Table also obscures distinctions in the bio-
dency for the liposomes to accumulate 5). Because of its high content of logical properties of the various con-
in mononuclear phagocytes (41). polyunsaturated linoleic acid, purified stituent phospholipids. In foodstuffs, a
Moreover. dipalmitoyl phosphatidyl- soy phosphatidylcholine exchanges minimum requirement for a definition
choline/dimyristoyl phosphatidylglyc- with saturated phospholipids in circu- of the source of the lecithin and its
erol (9: I) Hposomes stimulate interfer- lating lipoproteins and is therefore average content of phosphatidyl-
on-wtumor necrosis factor c-ecuvared used as a drug to reduce plasma choline (e.g .• soy lecithin, 25% phos-
mouse macrophages. while dipalmi- cholesterol concentrations (45). Soy phatidyJcholine) would cover most of
toyl phosphatidylcholine/phos- phcspbatidylcho+ine has also been its commercial applications. Where an
phatidylserine (7:3) liposomes are used for many years as a drug for the additional process has been introduced
inhibitory (42). Phosphat idyl serine treatment of liver diseases (46), in that is likely to have altered the fatty
also has several direct pharmacologi- addition to its dietary use in neurodc- acid content, this should be indicated
cal effects on the central nervous sys- generative disease. Recent studies (e.g .. hydrogenated soy lecithin, 25%
tem (43). Even with liposome tormu- suggest that it may be of benefit in the phosphatidylcholine). This is in keep-
lations which are immunostimulatory, treatment of acne vulgaris (47). ing with the requirements of the U.S.
the immunoglobulin subtype of anti- From a pharmaceutical standpoint, 1990 Nutritional Labelling and Educa-
body produced differs when using therefore. it is crucial to define both tion Act for definition of the saturated,
dipalmitoyl phosphatidylethanolamine the polar head groups and the fatty monounsaturated, and PUFA content
rather than dimyristcyl phosphatidyl- acid constituents of both single-phos- of commercial lecithin (48).
glycerol in combination with dipalmi- pholipid preparations and mixtures, as For cosmetic and pharmaceutical
toyl phosphatidy1choline (42). used in Hposomes, because these char- applications. the term "lecithin"
Different modes of administration acteristics can markedly affect both should never be used, either in
also may reveal unusual distinctions in pharmacological propenies and toxici- describing a product or in specific
the biological effects of liposomal ty. Especially as excipients or as drug research articles. All too often it is
phospholipids. Given by intraspinal carriers, clear definition of the phos- still possible to find an original
administration to rats (a route often pholipids used facilitates distinction research article in which a drug, vac-
used clinically for opiate analgesics), between tested, safe phospholipids, on cine, or other compound is described
for example. dipalmitoyl phos- the one hand, and synthetic com- as being prepared "in Hposomes"
phatidylcholine. but not soy phos- pounds with potentially diverging bio- without further characterization. All
phatidylcholine. liposomes caused logical activities on the other. phospholipid constituents of cosmetic
allodynia. a heightened sense of pain The comparative properties of or pharmaceutical preparations should
to normally innocuous stimuli (44). commercial lecithin and purified be described in full with a definition,
Several of the direct biological phosphatidylcholine are summarized where possible. of their fatty acid con-
effects of phospholipids per se. which in Table 6. stituents (e.g .. dipalmitoyl phos-
have been alluded to previously. have phatidylcholine or 1,2-dipalmitoyl-slI-
led to their introduction as pharma- Conclusions for terminology glycerol (3) phosphatidylcholine]. NOI
ceutical products. Of all the naturally The lax use of the term "lecithin" for only does this avoid confusion. but
occurring phospholipids detected in the ingredients of various commercial assists the interpretation of biological
soybeans and other plant seeds. phos- products prepared for human applica- effects observed. Where natural prod-

INFORM Vol. 7. no. 11 (Novembef 1996)


1174

LECITHIN

ucts are used, the degree of purifica- and P.E. Heckelman. The Merck Long-Chain Triglycerides, Eur. J.
tion should be given (e.g., soy phos- Index (11th Edn.), Merck and Co. cu« Invest. 17:402-407 (1987).
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Yean; of Experimental and Clini-
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(EPL). edited by K.J. Gunder- TEL: 49-721194374-0
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