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)


consider the possibilities
realize, from the food we eat to the
roads we drive on.
Lecithin can be found in food
products such as cake mixes. cheese.
candy. chewing gum, chocolate.
dehydrated foods, ice cream. instant
foods. pasta. bakery products, mar-
garine. and whipped topping.
Lecithin also is used for products
other than food, such as adhesives,
adsorbants. animal feed and pet food,
catalysts. soaps, cosmetics. paints
and coatings. waxes and polish. inks
and dyes, computer printer and pho-
tocopier toners. metal processing.
explosives. pesticides, fertilizers,
plastic and rubber molding. concrete
curing. masonry and asphalt prod-
ucts. dust-control agents. magnetic
media, leather tanning. lubricants,
oil-spill control. textile manufactur-
ing, production of plastics, paper pro-
duction and coating, wood preserve-
lives, and release agents.
What is lecithin?
Soybean oil makes up less than 20%
~------------+l~
of the soybean, and less than 3% of
soy oil is lecithin. If lecithin makes up
only 0.5% of the bean, why even
bother with it?
Lecithin is extracted as a co-prod-
uct of the vegetable oil relining pro-
cess. where phosphorus-containing
compounds are removed to improve
oil quality. As soybean processing
increased. lecithin usually was added
back 10 the meal or to animal feeds.
Some oil processors recognized the
potential of lecithin as a mullifunc-
tiona I additive for food. feed. and
industrial applications.
"Recovery of lecithin and market-
ing of its many modified forms have
become a part of the economics of
soybean processing," said Frank
Orthoefer. an industry consultant.
Soybean oil is removed from soy-
bean (flakes) with a solvent. usually
hexane. Filtered soy oil can be
degummed by adding water and cen-
trifuging the mixture to separate the
hydrated gums from the oil. About
90% of the phospholipids in oil can be
removed by water degumming.
Wet gums require immediate pro-
cessing, as they are high in moisture
(roughly 50% water) and will begin
decomposing within an hour or two.
To process gums to a crude lecithin
grade, the wet gums are dried and
quickly cooled. Lecithin can be
bleached as wet gums between the
centrifuging and drying stages.
The dried gums are in a plastic
state, and can be left in this form or
fluidized by adding oil or edible fatty
acids to reach viscosities that promote
easier handling. High-clarity lecithins
are made with more filtering, either in
the miscefla (the mixture of hexane
applied to soybean flakes and the
extracted soybean oil). crude soy oil.
or as lecithin.
Additional processing steps are
available to obtain the necessary qual-
ity and characteristics for specific
applications (see "Processing innova-
tions," page 1164).
Applications
"About 80% of the soy lecithin pro-
duced is sold (for use) as food emulsi-
1159
fiers, and 20% (for use) in a variety of
industrial applications," said
Lawrence Johnson, director of the
Center for Crops Utilization Research
at Iowa State University.
Lecithin is a surfactant. which can
be used to create an emulsion of two
or more incompatible substances. An
emulsion is a suspension of small
droplets of one liquid in another that
is immiscible with the first. Phospho-
lipids' hydrophobic fany acid hydro-
carbon tails have an affinity for fats
and oils, and phospholipids'
hydrophilic polar head groups have an
affinity for water.
The hydrophilic-lipophilic balance
(HLB) roughly indicates an emulsifi-
er's preference for oil or water.
Lecithins can be processed to obtain
an HLB of2 (oil-loving) to 12 (water-
loving). Low HLB indicates more effi-
cient water-in-oil (w/o) emulsification
properties, and high HLB indicates
more efficient ojl-i n-water (o/w)
emulsification.
The primary usage of lecithin in
food is as an emulsifier. For other
food uses, it softens and retains mois-
ture, reduces viscosity, stabilizes, and
disperses. In baking, lecithin com-
plexes with gluten proteins as a dough
conditioner and acts as a wetting
agent.
With a growing trend toward
reduced-fat products, lecithin is find-
ing a niche of increasing business. Fat
removal from a baked food product
formulation may cause lowered
lubricity and handling properties,
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
other emulsifiers and gums into the
formulation.
Lecithin also is used as a release
agent through its role as a surfactant.
Lecithin's edible nature makes it suit-
able for use on both cooked products
(pan release), and release of food
products from conveyor belts in com-
mercial operations. Release agents
also are used to prevent sticking in
(conlinutd on pagt 1/62)
INFORM. Vol. 7. no. 11 (November 1996)
1162
Lecithin i. Ju.1 one 01 many product. derived lrom processing toybean •.
[continued from page. 1159)
finished food products, such as cheese
slices.
Also used as a biodegradable
release agent in many nonfood appli-
cations, lecithin promotes easier mold
release from several materials, includ-
ing plastics, resins. ceramics, roofing
materials, and concrete. It also pro-
tects the molds from rust and corro-
sion.
One of the largest nonfood uses is
in calf milk replacers. where it serves
in emulsifying, stabilizing, wetting,
and dispersing roles, Lecithin also
functions as a substrate for enzymes
added to the formula.
Digestibility of nonmilk fats in
calves is lower than that of whole-
milk fat unless lecithin is added. Even
a lecithin content of as little as 2%
improves the digestibility of beef tal-
low. coconut fat, and lard.
Human nutrition
Phospholipids playa part in a wide
range of human metabolic processes
as well: fat absorption. cholesterol
metabolism. regulating serum lipid
level, fat transport. blood clotting,
nerve function. lung function, biosyn-
thesis of prostaglandins, and vision.
The line between nutritional and
pharmaceutical uses of lecithin and
purified phospholipids is becoming
INFORM. 'Yt>I. 7, no. '1 (NCNefTlber 1996)
LECITHIN
more blurred than it has been. Phos-
pholipids are used in fields of geri-
atrics, fat metabolism, neurology. and
liver function, and also in treatment of
convalescent patients, arteriosclerosis,
and certain types of gallstone forma-
tion. Research is continuing into
effects on memory, blood cloning,
blood pressure, and vision.
Some of these medicinal uses,
however. are in the form of dietary
supplements. Lecithin has been wide-
ly available as a retail dietary supple-
ment, as capsules or granules. usually
containing less than 35% PC. If a
higher PC content is desired, the
lecithin must be fractionated.
Mixing deoiled lecithin with alco-
hol will separate the lecithin into two
phospholipid fractions. While PE frac-
tions equally into alcohol-soluble and
insoluble portions, PC is alcohol-solu-
ble and PI is alcohol-insoluble. Chro-
matographic separation can then be
used to prepare polar lipids of the
highest purity.
The American lecithin Co .. wholly
owned by Rhone-Poulenc Rorer's
Cologne-based Nauermann Phospho-
lipid GmbH, markets a 100% PC
product. The company points to stud-
ies that show the amount of PC pres-
ent in the brain decreases after age 30.
A better studied area is the use of PC
as a precursor for acetylcholine,
neurctransmiuer. Brain acetylcholine
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
are set by the Food and Nutrition
Board in the United States. Several
nutrients important to health, such as
choline and folic acid, do not have
RDAs.
The phospholipid congress, spon-
sored by the AOCS Phospholipid
Division (international Lecithin and
Phospholipid Society) and several
companies, focused on the role of
choline, lecithin, and other phospho-
lipids in brain development and mem-
ory, decreasing the risks of heart dis-
ease and cancer, and cell functioning.
According to Lucas Meyer, another
phospholipid, phosphatidylserine
(PS). is essential to the functioning of
all body cells but is most concentrated
in the brain. It is involved in a variety
of nerve cell functions, including
nerve transmitter release and synaptic
activity.
Clinical studies have suggested that
PS can support brain functions that
decline with age. Lucas Meyer has
spent seven years developing a pro-
cess to manufacture PS (found at less
than I % in lecithin) after investigating
the evidence supporting its use as a
dietary supplement.
"We've been marketing phos-
phatidylserine for about a year and a
half now," said Susan Gurkin, director
of technical services at Lucas Meyer
Inc" the U.S. affiliate of Lucas Meyer
GmbH in Germany.
"We're laking a different approach
a with PS:' Gurkin said. "We're taking
the proactive approach of providing

the information and educating con-
sumers rather than just selling the raw
material."
Lucas Meyer plans to do the same
thing with PC next, Gurkin says, That
would put them into competition with
American Lecithin's PC product,
PhosChol. although they may not be
offered through the same outlets,
"Normally. our product won't be
found in a majority of health-food
stores," said Randy Zigmont, presi-
dent of American Lecithin. "It takes
an educator to explain to the consumer
the difference between PhosChol and
an ordinary lecithin supplement."
PhosChol is marketed by American
Lecithin directly through alternative
medicine providers. The company
markets the supplement for memory
enhancement. liver protection. and
cholesterol reduction, and also for
antiulcer effects when used in combi-
nation with nonsteroidal antiinflam-
mation agents.
As a finished consumer product,
PhosChol differs from other American
Lecithin purified phospholipids that
are for use as raw materials in prepar-
ing pharmaceuticals. The company
also markets commercial-grade
lecithin.
"Our mission is to develop purified
phospholipids for use in pharmaceuti-
cal, nutritional, and dermatological
applications," Zigmont said. "Phos-
pholipids in dermatological applica-
tions increase the bio-avaitabillty of
drugs. enhance skin permeation. and
stabilize active ingredients in topical
preparations."
In pharmaceutical applications,
phospholipids can reduce undesirable
side effects of new and existing drugs.
he said.
Pharmaceuticals
Phospholipids can serve as active
ingredients in pharmaceuticals by hav-
ing an effect on biochemical metabol-
ic functions. or as adjuvants (aids)
because of their physical-chemical
properties. Active ingredient research
has focused on pc, although there is
interest in other phospholipids.
As adjuvants. phospholipids are
used as emulsifiers for intravenous
infusion solutions, known as parenter-
al solutions. For parenteral solutions.
PC and PE need to be in a specific
ratio for the emulsion to be stable.
Phospholipids are also used to pro-
duce liposomes. Liposomes are closed
spherical membranes that, in their
simplest forms, consist of internal
aqueous centers surrounded by two
layers of phospholipids. Again. a spe-
cific ratio of PC to PE (80:20) is need-
ed to fonn stable membranes.
According to Parnham, PC is the
only phospholipid that forms Hpo-
Powdered (left) and granular
(rlghl) deoiled lecithin
somes spontaneously in aqueous
media. All others require additional
stabilizing compounds 10 prevent the
breakdown of the liposomal structure.
Lipophilic ingredients can be
embedded in the fatly regions between
the phospholipid bilayer, while
hydrophilic substances are held in the
aqueous internal space of the lipo-
some. Multilamellar liposomes arc
composed of more than one bilayer.
and can allow several compounds to
be compartmentalized.
Liposomes can be used in cosmet-
ics to carry moisturizers, sunscreens
or tanning agents. vitamins, or fra-
grances. The main use to dale has
been for skin- and hair-care products.
but the hottest growth area is for med-
ications. The body absorbs some med-
ications more readily when they are
administered in liposome form. Lipo-
somes can be targeted for specific
organs. to deliver the drug directly to
the site it is designed for (see lipo-
1163
somes sidebar on page 1166).
"There are two sides to our busi-
ness: to supply phospholipids to the
research community, and to supply
bulk material to the pharmaceutical
industry, mostly for use as drug deliv-
ery systems," said Walter Shaw, presi-
dent of Avanti Polar Lipids.
According to Shaw. the first phos-
pholipid product to hit the drug deliv-
ery market was Exosurf, a lung surfac-
tant for neonatal babies. "This treat-
ment requires the very specific com-
ponent of dipalmitoylphosphatidyl-
choline," Shaw said. "It won't work
without it."
Liposomes can do more than just
deliver a drug. though. They can also
lessen the negative effects associated
with drugs.
"Phospholipids can serve to cover
up a toxic drug until delivered to the
site of infection, by use of lipo-
somes," Shaw said. "Transporting
drugs in phospholipid membranes or
liposomes can lessen the side effects
of a drug."
Shaw said no products are out yet,
but gene therapy can be accomplished
by associating a cationic lipid to the
gene to be inserted. The lipid helps to
camouflage the genetic material and
transport it across the cell membrane,
according to Shaw.
The pharmaceutical market is one
of the few remaining for uses of egg
lecithin, which was identified long
before soy lecithin. The composition
of polar lipids and fatty acids in egg
lecithin is different than thai in soy-
bean lecithin, which is advantageous
in certain situations. Egg lecithin is
more expensive, however, and is
restricted by other issues as well.
"The FDA has questions about the
viral control on egg lecithin. Viral and
protein contamination From soybean
lecithin are not thought to be a threat
at this time," Shaw said.
Agricultural chemicals
Liposomes also could be used in agri-
cultural chemicals. to promote the
mixing of compounds that otherwise
might be incompatible. The structure
of liposomes also could be valuable
for applying pesticides because of the
structural similarity to biological
membranes.
INFORM, Vol. 7. no. II (November 1996)
1164
LECITHIN
LecIthIn quallty cen be affected by aoybean growth lind development,
and proclsslng.
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
changes in processing technology,"
said Roger Sinram, industry con-
suuant. 'There is a push to cut back
on the amount of hexane used in
processing. for example."
Although most soybean proces-
sors have been using the same tech-
L.:======:J nology for many years to extract
lecithin, there have been some recem innovations, such as
the five described here.
One extraction option being proposed is degumming in
the miscella. Lecithin could be separated out by using
membranes with pores large enough to allow flow of oil
and solvent but small enough to restrict the phospholipids.
Lucas Meyer experimented with membrane materials and
found that plastics may swell and decrease the size of the
pores. Ceramic membrane filters are not susceptible to
swelling and perform beuer in phospholipid separation tests.
"Membrane technology may even eliminate the refiner
step for soy oil," said Bernie Szuhaj, director of research
and development for Central Soya. Micropore membrane
technology could possibly be used to separate the various
phospholipid fractions in lecithin, according to Sinmm.
Another proposed separation technology is to degum
soy oil with compressed gases. such as carbon dioxide or
propane. Propane does ncr react with lecithin. and could be
recovered at room temperature and pressure. Lecithin
would be recovered as a wet sludge by centrifuging the oil.
INFORM. Vol. 7. no. 11 (November 1996)
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
as well !III atorage small pari of the soybean product,
growers are not pushing it," Johnson
said. "The lecithin producers are
The lecithin produced is free of oil, with a phopholipid
composition comparable to lecithin deoiled with acetone.
Although these new ideas in lecithin extraction may
involve new technology, the least expensive way to get
lecithin out of soybeans is still the tried-and-true method
that has been used for decades. New methods may have
made it as far as laboratory testing or even pilot-plant
scale, but a significant cost reduction or increase in prod-
uct quality must occur before companies will switch over.
"While we have looked at various lecithin extraction
technologies, 10 date we have elected instead to invest in
improvements at other points in our soy processing oper-
ations where changes may have more of an impact," said
Don McCaskill, director of the research and technical
center at Riceland Foods Inc .• a farmer-owned co-op
based in eastern Arkansas. "We believe our new
dehulling system, for example. will give us more long-
term benefit for the cost involved."
Not all phospholipids are removed from soybean oil
during water degumming. One proposed alternative in
this area involves using the phospholipase A2 enzyme to
hydrolyze the nonhydrntable phospholipids (NHPs) after
soy oil has been degummed with water. This creates a
Iysophospholipid that can be hydrated with water and
thus removed from the oil by centrifuging.
While proven in a laboratory setting, this technology
is not currently scheduled for use in lecithin production.
It is also more of interest to oil producers. to reduce
phosphorus content in the oil. than to lecithin producers.
The more common method of removing NHPs is to
 1165

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

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

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

1166

LECITHIN

binding aid, and by reducing leaching
of feed components, according to
Orthoefer.
According to the United Nations
Food and Agriculture Organization
(FAG), aquaculture is one of the
fastest growing food production activ-
ities in the world. In 1994 (the latest
available FAD data), fish and shellfish
production grew over two million
metric IOns (MT), a leap of 13% over
1993 figures.
Global aquaculture production of
fish, crustaceans, and mollusks has
more than tripled since 1975. and is
expected to rise to 21 million MT by
2000 and 62 million MT by 2025.
Most of that growth. however. is
occurring outside the United States.
Asia continues to lead global aquacul-
ture efforts, with China, India, Japan,
Korea, and The Philippines combining
to account for approximately 80% of
the total. In 1994, aquaculture produc-
lion of fish and shellfish in China con-
tributed over 50% to that country's
total national fishery production. far
more than the United States. where
less than 7% of total domestic fish
production was from aquaculture
operations.
Yet in the United States, catfish
production will have jumped tenfold
from 1980 levels if predictions of 345
MT by 2000 prove correct. U.S. aqua-
culture is on the rise, which means
that the market for fish and crustacean
feeds is also expanding.
"Much of the aquaculture feed
industry now uses lecithin concen-
trates," Onhoefer said.
"Aquaculture is indeed an exciting
field to watch," said Lance Colbert,
manager of lecithin technical services
at Archer Daniels Midland (ADM)
Lecithin, which has an aquaculture
center for research and production.
"We expect this use of lecithin to
increase."
The future
The lecithin industry has room to
grow. According 10 Charles Worrall,
marketing manager for Central Soya,
at present only 40% of the gums in
soy oil are convened into lecithin. In
essence, the lecithin market would
have to double to utilize current
potential production capacity.
How could over half of potential
lecithin production be thrown away?
The answer lies in the fact that it is
not thrown away, but sold at a dis-
count as soapstock. a mix of soy oil
residues derived from caustic refining,
or added back to the soybean meal,
where its caloric value increases the
meal value.
"It is capital-intensive to separate
lecithin, and some are forgoing it
(separation) to throw all of the gums
into animal feed," Sinram said. "The
processing, handling, separate tank-
age, and logistical hassles make it
(lecithin recovery) not worthwhile for
many, given that crude lecithin may
fetch only 40 cents (a pound) com-
pared to getting 10 cents for the gums
to be used in feed."
These factors play a role in
lecithin's growth prospect.
"Worldwide lecithin supplies are
growing 1-2% faster than demand
each year. so worldwide stocks are
gradually increasing," Worrall said.
"Demand for value-added products is
growing much more quickly."
Value-added lecithin products may
or may not be a part of your soybean
processing business, depending on
where you are located. "Unlike Europe,
North American lecithin companies
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
methods of making active ingredi-
ent carriers are to use other materi-
als to make liposomcs, or even use
other carriers entirely.
"The cost of fractionation is still
an issue, as there is a low level of
L " demand," said Walter Shaw, presi-
dent of Avanti Polar Lipids. "As
demand increases, production capacity increases and the
price will decrease. So as the market grows, prices will
become competitive."
Incorrectly judging the size or timing of the market
may be enough to sink even the best marketing plans. "I
know of some in this industry that invested heavily in
large-scale production and have lost everything," Shaw
said. "h is a real balancing act."
"One reason the cost is high is that for every kilogram
of PC you make from lecithin, you generate nine kilo-
grams of by-product," said Randy Zigmont, president
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."
Yet the co-products are not worthless. According to
Zigmonl, they can be blended back in with other lecithin,
but they also have unique properties in their own rights.
"For instance, PE has been shown to exhibit antioxi-
dant properties," Zigmont said. "Products derived from
the by-products (PE and PI) have been shown to increase
yield value in chocolate manufacture."
The limited size of the lecithin market, combined with
few companies working the field, leads to frequent busi-
ness partnerships, For instance, Stern Lecithin & Soja
has the responsibility for selling the by-product and food
fractions from Nattennann Phospholipids processing in
Europe. Central Soya has those rights for the rest of the
world market.
Another issue holding back phospholipid-based lipo-
somes is their stability in cosmetics formulations. Llpo-
somes based on other materials or nonliposome polymer-
ic capsules can duplicate the feats of liposomes without
the restrictions placed on phospholipids.

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

 1167

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

"Phospholipid stability in formulations is still an issue
of concern," Shaw said. "There are a couple of ways to
get around this problem. First, you can move from natu-
ral products 10 synthetic variations. This allows you to
control the number of double bonds rather than just take
whatever nature gives you."
According to Shaw, synthetic phospholipids are mere-
ly natural phospholipids where the fatty acids have been
rearranged on the glycerol backbone. This creates a spe-
cific profile that determines the physical properties of the
molecule.
"Second, ester bonds in the presence of water will
hydrolyze:' Shaw said. "ln that case, the hydrolysis can
be limited by using a lyophilized formula and limiting
exposure 10 water. A phospholipid can be shipped as
powder, and then sterile buffer is added on site to pro-
duce liposomes when needed."
Another factor with liposomes is the limited quantity of
lipophilic and hydrophilic materials that can aggregate in
the bilayers and in the core, respectively. "Liposomes can
be given a negative charge, which forces open a wider
space in the center of the liposome. allowing them to take
up more of a hydrophilic drug," Shaw said. "Some charged
ltposornes can bind specifically to cell walls or to proteins."
Yet there will always be resistance to change. "In
the liposome area, phospholipids are competing against
existing technology that may be cheaper and more
entrenched," said Roger Sinram, industry consultant.
Liposornes have some advantages, however, that can-
not be duplicated by alternative carriers. "There are com-
peting drug delivery vehicles, but phospholipid lipo-
somes are natural products--even the synthetic variations
of them-so 10 metabolize them is easy," Shaw said.
"Others (drug delivery systems) are not necessarily based
on natural materials, so metabolism becomes problemat-
. .,
". Although injectable drug delivery has become the
leading research area for lipcsomes. there are other
applications receiving increased scrutiny. "Liposomes
are not restricted to drug delivery, but can be used in
foods as well," said Bernard Szuhaj. director of research
and development for Central Soya, "Central Soya is
focusing on food uses, including adding flavors with
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-
ly isolated phosphatidylcholine. Since
that time, "lecithin" and "ph os-
pharidylcholine" frequently have been
used interchangeably.
The IUPAC-JUB (International
Union for Pure and Applied Chem-
istry-International Union of Biochem-
istry) proposals for the nomenclature of
lipids provide a systematic definition of
the chemical structures of pure phos-
pholipids and propose a shorthand
nomenclature which has found increas-
ing acceptance in the biochemical liter-
ature (3,4). According to this nomen-
clature, 3-511 phosphatidylcholine (Ptd
Cho) is the recommended name for
I ,2~diacy l-sn-glycerolt Sjphospho-
choline (acyI2GroPCho) (3). The old
trivial name of "lecithin" is neither rec-
ommended nor does it offer any advan-
tages over the IUPAC-IUB nomencla-
ture (3-5).
However, outside biochemical cir-
cles, the term "lecithin" still is used
widely, frequently without clear defi-
nition of what chemical entities the
term is intended to cover. The Inter-
national Lecithin and Phospholipid
Society (ILPS) has published the fol-
lowing definition for lecithin: "a
mixture of glycerophospholipids
This article by Michael J. Parnham, Pomhmn Adviser
ry Services, Van Guericu AUee 4, 0-53125 Bonn,
Germany. and Phannacoiogical11lStihlle for Life sci-
entists, Goethe Unil'ersity Franlifun. 0-60439 Frank·
fun. Germany, is based on his presentation during the
87th AOCS Annual Meeting & Expo
held earlier this year in Indianapolis. lndiana.
obtained from animal, vegetable or Current international lecithin speci-
microbial sources, containing a vari- fications
ety of substances, such as sphingo- Commercial lecithin usually is
sylphospholipids, triglycendes, fauy extracted from soybeans or from egg
acids, and glycolipids" (6). This def- yolk. Crude soya lecithin contains
inition covers the wide variety of 52% mixed phospholipids of which
natural and refined lecithin products 12-18% is phosphatidylcholine.
commercially available, but does not Oeoiling with acetone generates a
indicate the relative proportions of granular product containing 78%
the different components, nor does it mixed phospholipids (20-95% pbos-
define the purification stage of the phatidylcho1ine) which on further
product. Furthermore. the ILPS defi- extraction with ethanol can be frac-
nition of lecithin clearly would not tionated to yield high concentrations
include a synthetic or semisynthetic of phosphatidylcholine (7) (Table I).
product. Specifications regarding purity gener-
The current regulatory specifica- ally reflect the need to limit solvent
tions for lecithin and the problems contamination as well as the presence
arising as a result of different con- of toxic heavy metals and perox.ides.
stituents with varying biological activ- The result is that there is little global
ities will be reviewed briefly and pro- standardization of the actual con-
posals made for clear and effective stituents and physical properties of
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-
phatidylchcline which is usually well-
defined with regard to source. chemi-
cal composition, and physical proper-
ties.
The lecithin specifications of the
Food Chemicals Codex (FCC IrQ (8)
are given in Table 2. The product to
which these specifications refer is
defined as food-grade lecithin from
soybeans and other plant sources con-
sisting of a complex mixture of ace-
tone-insoluble phospholipids (mainly
phosphatidylcholine, pbosphan-
dylethanolamine, and phosphatidyli-
nositol) combined with various
amounts of other substances such as
triglycerides, fatty acids, and carbohy-
drates in varying proportions. The
specified product contains 90% or
more of phospholipids of differing
grades, forms. and color. In contrast,
the Food Additives Handbook (9)
describes lecithin simply as "a com-
plex mixture from soybeans, and other
plants." without reference 10 its con-
stituents, stating only that in oleomar-
garine it is limited to 0.5%.
The US Pharmacopeia (USP XXII)
or National Formulary (NF XVII)
(10) also provides a similar descrip-
tion 10 that of the FCC III, though
without defining the phospholipid
content or the peroxide value (Table
2). These specifications also are given
in the Handbook of Pharmaceutical
Excipients (HPE) published jointly by
the American Pharmaceutical Associ-
ation and The Pharmaceutical Society
of Great Britain (II), which defines
lecithins from both plants and eggs.
The Merck Index (12) specifies a
slightly lower acid value (Table 2).
The Japanese Monograph (lSCI-IIJ
(13) specifies a lower heavy metal
content.
The European Community specifi-
cations (Guideline 78/664IEWG) for
lecithins (E322) (14) are also included
in the Monographs far Emulsifiers for
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-
ciation (EFEMA) (15). These differ in
some respects from the U.S. specifica-
tions. E322 distinguishes between
lecithins (which may be from plant
sources or from eggs) and hydrolyzed
lecithins. The latter are permitted a
higher acid value and somewhat lower
content of acetone-insoluble matter
than nonhydrolyzed lecithin, though
both European specifications for ace-
tone-insoluble matter are stricter than
those of the Federal Drug Administra-
tion (FDA) (Table 2). This also
applies to the specification for the per-
oxide value, though the U.S. specifi-
cations marginally are stricter with
regard to water and heavy metal con-
tent. E322 also specifies that the
lecithin should contain not more than
2% volatile matter by drying at 105°C
for one hour. This presumably is due
to the very different specifications for
pharmaceutical use' in German-speak-
ing countries (Table 3).
These are predominantly based on
coloring and ashing procedures. In all
three countries [Germany (DAB),
Austria (ClAB). and Switzerland (PH
6)] the nitrogen content is specified as
1.7-2% and the phosphate content as
at least 3% (16-18). In Germany (16).
arsenic and heavy metal content are
not specified, but the German Regula-
tions for the Use of Additives
(Deutsche ZusatzstojJverkehrsverord-
nung) (19) recommends maximums of
3 ppm for arsenic and 50 ppm for
heavy metals in agreement with the
E322 specifications. The German For-
eign Substance Commission
(Deutsche Fremdstoffkommission)
(20) recommends an acid value of not
more than 4%. Hager's Handbook
(21) quotes the purity specifications
given by the USP XXII and the
OAB81, but also distinguishes
between lecithin from egg and soy-
beans. The latter is defined as contain-
ing approximately 95% phosphatidyl-
choline and <1% other phospholipids,
while egg lecithin is defined as con-
taining approximately 94% phos-
phatidylcholine and <2% other phos-
pholipids; fatty acid ranges are also
given. For both lecithins, Hager's
Handbook provides slightly differing
phosphate contents and distinct iodine
values.
The broad differences in interna-
tional specifications also stem from
different traditions in the applications
of commercial lecithin. On the one
hand, the product as a crude prepara-
tion may be used as an emulsifier in
foods and, on the. other hand, as a
highly purified, biologically active
pharmaceutical-grade phosphat idyl-
choline.
It is at the level of application that
a differentiation in terminology is
required initially. On the basis of an
assessment of the literature since
1930, the Life Sciences Research
Office (LSRO) of the Federation of
American Societies for Experimental
Biology reviewed the use of lecithin
obtained from plant sources as a
human food ingredient (22). and on
the basis of the LSRO report, the FDA
subsequently issued new regulations
(21 CRF 1841400) affirming the "gen-
erally regarded as safe" (GRAS) status
of plant-derived lecithin (23). (It is
pertinent to the present article that the
LSRO report drew attention to the fact
that the interchangeable use of the
terms "lecithin" and "phosphatidyl-
choline" "has created confusion," rec-
ommending that the trivial name
"lecithin" be restricted to the commer-
cial product.) When it is used in low
concentrations as an emulsifier,
lecithin's GRAS status covers any
potential biological effects of com-
mercial lecithin. However, when high-
ly purified components of lecithin are
used in larger doses as nutritional sup-
plements or as drugs, the biological
activity of the product becomes much
more relevant. In this case, specifica-
tions for limitation of impurities must
be complemented with definitions
which reflect the desired biological
activity, and this may vary depending
on the constituents.
Distinctive biological activities of
phospholipids
Nutritional use. Lecithin is used both
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
Table 5
Fatty acid composition of different soya phospholipid
Fatty acids
Palmitic acid
Stearic add
Oleic add
Linoleic add
Linolenic acid
Q Pen:enlll3C oflO11I1fally acid CQf1tent.Reference 49.
have confirmed the importance of
dietary lecithin as a precursor of
choline and have demonstrated benefi-
cial effects of dietary lecithin when
administered to elderly patients with
some neurological diseases. particu-
larly tardive dyskinesia (29.30). In this
respect. it is not lecithin as a mixture
of phospholipids which is of value.
but specifically phosphatidylcholine.
In order to relate neurological effects
to the dose or dietary intake. it is
essential that the phosphatidylcholine
content of nutritional supplements be
clearly stated.
Phosphatidylcholine and choline
are not only of importance for the
neurological health of the elderly. The
plasma of newborn infants has a much
higher choline concentration than that
of adults (31). Human breast milk
within the first few days of lactation
contains high concentrations of both
free choline and other choline-con-
taining lipids. including phosphat idyl-
choline (32). It has. therefore. been
argued that infant formulas should
contain adequate concentrations of
various forms of choline. including
phosphatidyJcholine (not just lecithin).
to meet the infants' dietary require-
ments (32). Once again. the use of
lecithin as an emulsifier in infant for-
mulas necessitates definition of the
proportion of phosphatidylcholine that
is present in order to relate this 10
potential biological effects.
Cosmetic IUC. The major use of
phospholipids in cosmetics is in the
preparation of liposomes. These are
either used per se as skin moisturizing
agents or as carriers to facilitate skin
penetration of other cosmetic ingredi-
ents. Phosphatidylcholine is the only
phospholipid which forms vesicles
INFORM. VOl. 7. no. 11 (Novembef
LECITHIN
classes (%)'"
Phosphatidyl- Phosphatidyl-
choline ethanolamine
C16:0 20.5 31.6
CIS:O 5.5 3.2
CIS;) 10.5 8.7
C18:2 58.8 53.2
CIS:3 4 .• 3.2
(Iiposomes) spontaneously in aqueous
media. All other phospholipids require
the addition of other stabilizing com-
pounds to prevent the breakdown of
the liposomal structure. There is
increasing worldwide pressure to
reduce the safety testing in animals of
cosmetic ingredients. and within the
European Union such animal testing is
actively discouraged (33). Conse-
quently. the GRAS status of lecithin
usually is invoked to account for the
safety of phospholipids for cosmetic
use and to obviate toxicity testing.
However. phospholipids differ in
their biological effects on the skin.
Moisturizing or hydration of skin is
achieved by modifying the lipid con-
tent of the horny layer (strauon
cornea). Administration to normal
human skin of a liposomal dispersion
containing 80% phosphatidylcholine.
9% phosphatidic acid. and 4% N-
acetylphosphatidylethanolamine pro-
duced a 38% increase in skin humidity
(34). Decreasing the phcsphutidyl-
choline content and increasing the
phosphatidylinositol content of the
Iiposomes ultimately resulted in a dry-
ing. rather than a moisturizing, effect
on the skin. Soy phosphatidylcholine.
with a high content of PUFAs. which
are required for healthy skin. may con-
tribute toward the regulation of epider-
mal proliferation (35).
These effects, while not limiting
the dermal safety of phospholipids.
certainly emphasize that the terms
"phospholipids," "lecithin," or "lipo-
somes" are insufficient to define
potential or expected effects on the
skin. For this reason. it is necessary to
define the actual content of specific
phospholipids in products applied as
cosmetics.
1996)
Phosphatidyl- Phosphatidic
Inositol acid
47.7 34.0
8.2 8.1
4.9 11.9
36.2 44.7
2.8 1.3
Pharmaceutical usc. Purified phos-
pholipids from natural sources.
together with semisynthetic and syn-
thetic phospholipids, are employed as
pharmaceutical excipients and drug
carriers. as well as forming the active
ingredients of various pharmaceutical
products administered orally, topical-
ly. or parenterally. As an excipient. for
example for parenteral diazepam. soy
lecithin is used in the form of mixed
micelles with bile acid to improve sol-
ubility and reduce local irritancy (36).
In this respect, it is once again the
physical properties of the phospho-
lipids that are most important. so
therefore the content of specific phos-
pholipids is not crucial. The relatively
small amount of product administered
makes the biological distinction
between soy and egg lecithin-as
described for parenteral fat emul-
sions-irrelevant. However, use of
saturated. rather than highly unsaturat-
ed. soy phospholipids for the prepara-
tion of mixed micelles enhances floc-
culation and decreases the excipient
efficacy of the mixture (37). Conse-
quently. even as an excipient. a defini-
tion of the degree of saturation of the
lecithin used is needed.
Phospholipids also are the basic
building blocks of liposomes as drug
carriers. A wide variety of different
types of phospholipids. together with
additional charged constituents, pro-
teins. and cholesterol are formulated
in liposomes to enhance organ and
tissue targeting or to modify transport
capacity (38,39). Quite apart from the
fuct that additional charged con-
stituents and proteins can exert their
own biological effects. the liposomal
formulation of different phospholipids
is not without biological repercussions
 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
the phospholipid the greater is the len-
dency for the liposomes to accumulate
in mononuclear phagocytes (41).
Moreover. dipalmitoyl phosphatidyl-
choline/dimyristoyl phosphatidylglyc-
erol (9: I) Hposomes stimulate interfer-
on-wtumor necrosis factor c-ecuvared
mouse macrophages. while dipalmi-
toyl phosphatidylcholine/phos-
phatidylserine (7:3) liposomes are
inhibitory (42). Phosphat idyl serine
also has several direct pharmacologi-
cal effects on the central nervous sys-
tem (43). Even with liposome tormu-
lations which are immunostimulatory,
the immunoglobulin subtype of anti-
body produced differs when using
dipalmitoyl phosphatidylethanolamine
rather than dimyristcyl phosphatidyl-
glycerol in combination with dipalmi-
toyl phosphatidy1choline (42).
Different modes of administration
also may reveal unusual distinctions in
the biological effects of liposomal
phospholipids. Given by intraspinal
administration to rats (a route often
used clinically for opiate analgesics),
for example. dipalmitoyl phos-
phatidylcholine. but not soy phos-
phatidylcholine. liposomes caused
allodynia. a heightened sense of pain
to normally innocuous stimuli (44).
Several of the direct biological
effects of phospholipids per se. which
have been alluded to previously. have
led to their introduction as pharma-
ceutical products. Of all the naturally
occurring phospholipids detected in
soybeans and other plant seeds. phos-
phatidylcholine has the highest pro-
portion of PUFA subsrltuems (Table
5). Because of its high content of
polyunsaturated linoleic acid, purified
soy phosphatidylcholine exchanges
with saturated phospholipids in circu-
lating lipoproteins and is therefore
used as a drug to reduce plasma
cholesterol concentrations (45). Soy
phcspbatidylcho+ine has also been
used for many years as a drug for the
treatment of liver diseases (46), in
addition to its dietary use in neurodc-
generative disease. Recent studies
suggest that it may be of benefit in the
treatment of acne vulgaris (47).
From a pharmaceutical standpoint,
therefore. it is crucial to define both
the polar head groups and the fatty
acid constituents of both single-phos-
pholipid preparations and mixtures, as
used in Hposomes, because these char-
acteristics can markedly affect both
pharmacological propenies and toxici-
ty. Especially as excipients or as drug
carriers, clear definition of the phos-
pholipids used facilitates distinction
between tested, safe phospholipids, on
the one hand, and synthetic com-
pounds with potentially diverging bio-
logical activities on the other.
The comparative properties of
commercial lecithin and purified
phosphatidylcholine are summarized
in Table 6.
Conclusions for terminology
The lax use of the term "lecithin" for
the ingredients of various commercial
products prepared for human applica-
tion not only leads to confusion but
also obscures distinctions in the bio-
logical properties of the various con-
stituent phospholipids. In foodstuffs, a
minimum requirement for a definition
of the source of the lecithin and its
average content of phosphatidyl-
choline (e.g .• soy lecithin, 25% phos-
phatidyJcholine) would cover most of
its commercial applications. Where an
additional process has been introduced
that is likely to have altered the fatty
acid content, this should be indicated
(e.g .. hydrogenated soy lecithin, 25%
phosphatidylcholine). This is in keep-
ing with the requirements of the U.S.
1990 Nutritional Labelling and Educa-
tion Act for definition of the saturated,
monounsaturated, and PUFA content
of commercial lecithin (48).
For cosmetic and pharmaceutical
applications. the term "lecithin"
should never be used, either in
describing a product or in specific
research articles. All too often it is
still possible to find an original
research article in which a drug, vac-
cine, or other compound is described
as being prepared "in Hposomes"
without further characterization. All
phospholipid constituents of cosmetic
or pharmaceutical preparations should
be described in full with a definition,
where possible. of their fatty acid con-
stituents (e.g .. dipalmitoyl phos-
phatidylcholine or 1,2-dipalmitoyl-slI-
glycerol (3) phosphatidylcholine]. NOI
only does this avoid confusion. but
assists the interpretation of biological
effects observed. Where natural prod-

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

1174
ucts are used, the degree of purifica-
tion should be given (e.g., soy phos-
phatidylcholine.95%).
References
I. Gobley, M.. Recherches Cliniques
sur Ie Jaune d'Oeuf, J. Pharm.
cu« (Paris) /7:401-417 (1850).
2. Diakonow, C .• Uber die Phospho-
rhaltigen Kerper der Hubner- und
Storeier. Med. Chem. Untersuch:
2..221-227 (1867).
3. IUPAC-IUB Commission on Bio-
chemical Nomenclature, Nomen-
clature of Phosphorus-Containing
Compounds of Biochemical
Importance, Eur. J. Biochem.
79..1-9 (1977).
4. IUPAC-IUB Commission on Bio-
chemical Nomenclature, The
Nomenclature of Lipids, Ibid.
79:11-21 (1977).
5. Silvius, J.R., Structure and
Nomenclature. in Phospholipids
Handbook, edited by G. Cevc,
Marcel Dekker, New York. New
York and Basel, Switzerland,
1993. pp. 1-22.
6. Watkins, T.R, in Phospholipids,
edited by J. Hanin and G. Pepeu,
Plenum Press, New York, New
York, 1990, p. 301.
7. Schneider, M., Fractionation and
Purification of Lecithin. in
Lecithins: Sources, Manufacture
and Uses, edited by B.F. Szuhaj,
American Oil Chemists' Society,
Champaign, Illinois, 1989, pp.
109-130.
8. Committee on Codex Specifica-
tions, Food Chemicals Codex
(3rd Edn.), National Academy
Press, Washington, D.C .. 1981.
pp. 166-167.
9. Lewis, R.J., Food Additives
Handbook VNR, New York, New
York, 1989, p. 773.
10. Committee of Revision, The
United States Pharmacopeia
(22nd Rev.). U.S. Pharmacopeia!
Convention. Rockville. Maryland,
1980, pp. 1,572.
11. Handbook of Pharmaceutical
Excipients; American Pharmaceu-
tical Association. Washington.
D.C.. and Pharmaceutical Society.
Great Britain, London, 1986, p.
165.
12. Budavari. S.• J.O. Neil. A. Smith
INFORM,Vol. 7, no. 11 (November 1996)
LECITHIN
and P.E. Heckelman. The Merck Long-Chain Triglycerides, Eur. J.
Index (11th Edn.), Merck and Co. cu« Invest. 17:402-407 (1987).
Inc., Rahway, New Jersey, 1989, 27. Wendel, A., in Kirk-Othmer
p.854. Encyclopedia of Chemical Tech-
13. Yakuji Nippo, Ltd., The Japanese notogy; 4th Edn., Vol. 5, J. Wiley,
Standards 0/ Cosmetic Ingredi- New York, New York, 1995, pp.
ents, 2nd Edition, 1983, p. 418. 192-210.
14. E322-Lecithins, Official J. Eur. 28. O'Brien, B.C.. and V.G.
Commun. L 297/31,23.10.82. Andrews, Influence of Dietary
15. Monographs for Emulsifers for Egg and Soybean Phospholipids
Foods (2nd Edn.), European Food and Triglycerols on Human
Emulsifier Manufacturers Associ- Serum Lipoproteins, Lipids
ation, Brussels, Belgium, 1985, 2&7-12 (1993).
pp.I-5. 29. Growden. J.H., Use of Pbos-
16. Deutsches Arineibuch (7.Aus- phatidylchoJine in Brain Dis-
gobe], Deutscher Apotheker Ver- eases; An Overview, in Lecithin,
lag, Stuugan, Gennany, 1968, p. edited by I. Hanin and G.B.
150. Ansell, Plenum, New York, New
17. Osterreichisches Armeibuch (Bd York, 1987, pp.121-136.
II), Verlag der osterreichischen 30. Canty, D.J., and S.H. Zeisel,
Staatsdruckere, Vienna. Austria, Lecithin and Choline in Human
1981, p. 703. Health and Disease, Nutr. Rev.
18. Pharmacoooea Helvetica (6th 52..327-339 (1994).
Edn.), Eidgenosslscbe Druck- 31. Zeisel, S.H., M.F. Epstein and
aachen- und Materialzentrale, R.J. Wurtman, Elevated Choline
Berne, Switzerland, 1971, p. 807. Concentration in Neonatal Plas-
19. Dt. Zusanstoffverkehrsverord- ma, LIfe Sci. 26:1827-1831
nung, 20.12. 77 (8. Ges. BLl, S. (1980).
2653). 32. Zeisel, S.U., D. Char and N.F.
20. Dt. Fremdstoffkommission ut«, Sheard, Choline, Phosphatidyl-
1.11.67., DFG, Bad Godesberg. choline and Sphingomyelin in
21. List, P., and L. Hcrharnmer, edi- Human and Bovine Milk and
tors. Hager's Handbuch der Infant Formulas, 1. Nutr.
Pharmaeeutischen Praxis (5. Aus- 116..50-58 (1986).
gabe) Bd. 8, Springer Verlag, 33. Loprieno, N., Guidelines for
Berlin, Heidelberg, Germany, Safety Evaluation of Cosmetics
1993. pp. 699-700. Ingredients in (he EC Countries,
22. Wood, J.L., and R.O. Allison, Food Chem. Tosicol. 30:809-815
Effects of Consumption of (1992).
Choline and Lecithin on Neuro- 34. Artmann, C; 1. Reding, M. Ghy-
logical and Cardiovascular Sys- czy and H.G. Pretzel, Influence of
tems, Fed. Proc. 41:3015-3021 Various Liposome Preparations
(1982). on Skin Humidity, Parfiimerie
23. Randolph, WF., GRAS Status of Kosmetik 5:326-327 (1990).
Lecithin, Fed. Reg 35. Bonnekoh, B., and G. Mahrle,
48.-51149-51151 (1983). Cutaneous Application of Lipo-
24. Dickinson, E., Towards More somes-A Survey of the litera-
Natural Emulsifiers. Trends Food ture with Special Regard 10 Data
Sci. Technol. 4:330-334 (1993). Concerning Keratinocytc Cul-
25. Hailer, S., and G. Wolfram. influ- tures, Animal Experiments, and
ence of Artificial Fat Emulsifiers Clinical Studies, H+G Z Hauti-
on the Composition of Serum rankh. 65:99-105 (1990).
Lipoproteins in Humans, Am. J. 36. Mattila, M.A.K., and M. Suistorn-
C/in. Nut" 43:225-233 (1986). au, Intravenous Premedication
26. Hailer, S., G. Wolfram and N. with Diazepam. A Comparison
ZOllner, Changes in Serum Between Two Vehicles. Anaesthe-
Lipoproteins in Humans Follow- sia 39:879-882 (1984).
ing the Infusion of a Fat Emul- 37. Durr, M., J. Hager and J.P. Lchr,
sion Containing Medium- and Investigations on Mixed Micelle
 1175

and Liposorne Preparations for
Parenteral Use Based on Soya
Phosphatidylcholine. Eur. f.
Pharm. BiopJwrm. 40:147-156
(1994).
38. Oregoriedls. G .. Overview of Lipo-
somes. J, Antimicrob. Chemother:
28 Suppl 8:39-48 (1991).
39. Lesic, D., Liposomes. Amer. Sci.
80 ..20-31 (1992).
40. Pamham. M.J" Do Phospholipids
Have Toxicological Limitations",
in Phospholipids: Characteriza-
tion, Metabolism. and Novel Bio-
logical Applications. edited by G.
Cevc and F. Pelrauf AOCS Press,
mann and R. Schumacher. wbn-
Verlag, BingenlRhem. Germany,
1990, pp. 49--68.
47. Ghyczy, M., Phospholipon and
Natipide II: The Treatment of
Acne Vulgaris by Phosphatidyl-
choline from Soybeans. with a
High Content of Linoleic Acid. in
A Mirror of Continuous Research,
SOLUTIONS FOR HEATING IN
EDIBLE OIL PROCESSING
edited by E. Hoff. Nattermann
Phospholipid, Cologne. Germany,
1995. pp. 65-73.
48. ILPS White Paper, Lecithin and
the Nutritional Labeling Act,
INFORM 6..194-195 (1995).
49. Pardun, H., Die Pflantsnlecithine,
Verlag fur chemische Industrie H.
Ziolkowsky, Augsburg, 1988. •

i
Champaign. Illinois, 1995, pp.
56-66.
41. Allen, T.M., L. Murray, S. MacK- 95 BAR-HIGH-PRESSURE
eigan and M. Shah, Chronic Lipo-
some Administration in Mice:
Effects on Reticuloendothelial
Function and Tissue Distribution,
NATURAL CIRCULATION BlIJILER
J, Pharmacol. Exp. Ther.
229 ..267-275 (1984).
42. Phillips. N.C., and L. Gagne. Mod-
ulation of Murine Macrophage
Nitric Oxide Synthesis by Liposo-
mal Phospholipids: Correlation
with Liposome Immune Adjuvant
Activity. J. Drug Targeting
3..137-147 (1995). The executive
43. Toffano, G., and A. Bruni. Phar-
macological Properties of Phos-
., ., manufacturer of
boiler for
pholipid Liposomes, Pharmacal. hermetically closed
Res, Commun, 12:829-845 steam systems up to
(1980). 95 bar (1350 psi),
44. Yanez. A.M .• M.S. Wallace. D.O. 3025 kW
Shen, R.J. Y. Ho, T. Bui and T.L. (lOx 10' BTU/H)
Yaksh, Use of Liposomes for for Edibles Oils
Spinal Delivery of Alfentanil in
Industry process
Rats, Abstracts 7th World
heating.
Congress on Pain, Paris, France.
August 22-27, 1993, p. 220.
45. Oette, K.• On the Administration Advantages with
of Phosphatidylcholine- GEKA: more than
Metabolic and Pharmacokinetle 25 years experience,
Aspects in Humans. in 50th approved systems,
Anniversary of Phospholipid worldwide in the
Research (EPL), edited by K.J. Edible Oi/lndustry.
Gundermann and R. Schumacher,
wbn- Verlag, BingenlRhem, Ger-
many. 1990, pp. 35-48.
46. Kuntz, E.. The "Essential" Phos- GEKA ENERGY SYSTEMS
pholipids in Hepatology-50 GOTTFRIEDKNEIFEL
GmbH & Co. KG For Inlormation circle 1\ 11
Yean; of Experimental and Clini-
cal Experiences, in 50lh Anniver- Germany. Dieselstra8e 8
sary of Phospholipid Research 0-76227 Karlsruhe-Dur/ach
(EPL). edited by K.J. Gunder- TEL: 49-721194374-0
FAX: 49-721/494331