Introduction to the

Use of Lecithins

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Introduction to the use of Lecithins

Lecithins, the Natural Choice of Emulsifier !

Lecithins offer mankind unlimited applications in not only food but also animal feed as well as
many industrial applications. In order to appreciate what lecithins can do in practice it facilitates
the understanding by first reviewing the chemical nature of lecithins, they way they are extracted,
refined and processed from nature and the basic properties that are generated by these process
steps.

The lecithin molecule has a unique structure that allows formation of rigid multilayer membrane
structures, often referred to as “liquid crystal mesophases”. Nature use this property for the
membrane structure of all living cells and thus lecithin occur in plants and animals. Very few other
food emulsifiers occur in nature, but lecithin is the one-and-only emulsifier that is used directly as a
dietary supplement and eaten by the spoonfuls, sprinkled on foods or enjoyed as health beverages !

The most economic source for commercial production of lecithin are the seeds from soya beans,
sunflower- and rape seeds.

Lecithin, the E-number 322

Although lecithin has an E-number it is often just declared simply as “lecithin” and it enjoys a
positive consumer acceptance. Table 1 shows the European definition of lecithin:
Lecithin are mixtures or fractions of phospholipids obtained by physical procedures
from animal or vegetable food stuffs;
they also include the hydrolysed products obtained through the use of harmless and
appropriate enzymes. The final product must not show any signs of residual
enzymatic activity.
Lecithins may be slightly bleached in aqueous medium by means of hydrogen
peroxide. This oxidation must not chemically modify the lecithin phosphatides.

Table 1: Definition of Lecithin

Molecular Structure of Lecithin

Table 2 shows the molecular structure of Phospholipids. They are very analogue to triglycerides
but have only two fatty acids esterified to glycerol. The big difference compared with triglycerides
is that the third position of the glycerol moiety is phosphorylated and further esterified with side
chain moieties that also contribute to the lecithin functionality. The phosphatidylcholine is
excellent for emulsification – and also the choline fragment can not be synthesised by the human
body and needs to be supplemented in the diet. Phosphatidylethanolamine is less functional as
emulsifier, more sensitive to Calcium in hard water and it is responsible for the darkening of
lecithins on extended heating. A third significant component is Phosphatidylinositol and finally
Phosphatidic acid is simply phosphorylated diglyceride with no side chain on the phosphorous
group. The added functionality’s of these side chains are important since the objective of many
lecithin process steps is to alter the relative content of these components.

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A Technical Bulletin from
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Introduction to the use of Lecithins

CH 2 O C R' X = CH2 C H2 N + (C H 3 ) 3
Phosphatidy lcholine

O X = CH2 C H2 N + H3
R" C O C H Phosphatidy lethanolamine
H H

O OH
H OH HO Phosphatidy linositol
X = OH H
CH 2 O P O X O H
-
O- H OH

R' CO, R " CO : Fatty acids X = H : Phosphatidic acid

Table 2: Molecular Structure of Phospholipids

Table 3 exhibits a comparison between triglycerides, monodi- and monoglyceride and then the
phospholipids. It is evident that the lecithins have strikingly similar structures, especially if the
lecithin is “hydrolysed”, and thus it is not so strange that their application properties have many
similarities. The two biggest applications of these molecular structures are in baking and in
emulsification. No doubt lecithins earn their special extra unique release/lubrication property due to
their phosphorylated nature.

• F ats = T rig ly cerid es R1

R2
R 1 , R 2, R 3 : fatty a cid s
ch ain len g th C 8 < -> C 22 R3
ch ain : satu rated , m o n o -p o ly u n satu rated
• E m u lsifier b asis : M o n o -D iglycerid e

OH

CH 2 OH CH 2 OH

• L ecith in
D ig ly cerid e M o n o g ly cerid e

OH

O O

C H2 O P X O P X
C H2
O O
S ta n d a r d H y d ro ly se d lecith in

Table 3: Comparison of Molecular Structures

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Introduction to the use of Lecithins

Analytical Comparison of Lecithin

Table 4 shows a comparison of the main phospholipid isomers of lecithins from different common
sources. The content of phosphatidylcholine is always characteristically higher in American
soybean lecithin by several percent. Sunflower lecithin and Rape seed lecithin grown in Europe
approximate this level. The phosphatidylcholine of egg yolk is extremely high and explains some
of the unique properties of eggs in baking- and in emulsification applications. The reason eggs, and
especially egg yolks, are so difficult to “replace” is that the high level of phosphatidylcholine
interact with several egg yolk proteins, that are not commercially available. Phosphatidic acid offer
no emulsification properties. A proper commercial level would be 4-6 %.

Components Typical value (%)

PHOSPHOLIPIDS Soya Sunflower Rape Egg Yolk
Phosphatidylcholine PC 15 16 16 69

Phosphatidylethanolamine PE 11 8 8 24

Phosphatidylinositol PI 10 13 11 -

Phosphatidylserine PS <1 <1 <1 3

Phosphatidic acid PA 4 3 4 -

Table 4: Phospholipid Isomers of Vegetable Lecithines

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Introduction to the use of Lecithins

Commercial Production of Lecithin

Table 5 shows the principles of seed crushing and manufacturing of crude lecithin. Since lecithins
chemically are analogues to oils they follow the oil in the hexane extraction of crushed seeds but
since they are much more hydrophilic than the oils it is possible to make them absorb added water.
Then lecithins swell by forming their characteristic liquid crystal mesophases. This process is
called degumming. The viscous lecithin gum or slurry in water must be dried quickly under
vacuum and under controlled temperature, otherwise the lecithins either spoil microbially or they
brown by too high drying temperatures.

Table 5: Production of Crude Lecithin

A number of additional processing steps are possible in order to refine the crude lecithin. These
possibilities are listed on table 6 as well as their common Solae trade names. From left lecithin can
be hydrolysed enzymatically (the STERNPHIL-range), the phosphatidylethanolamine component

Stage 1: Oil mill

Selection and
cleaning of
soybeans
Crude soybean oil,
Soybean meal not degummed ca. 20%
Extraction
ca. 80%
Crude soybean oil
Lecithin Hydration of the degummed
W et gums phospholipids

Refining
Drying
Refined soybean
Crude lecithin oil
0.5%-0.6%

can be acetylated ( STERNPHIL CA, not permitted for European foods), the filtered lecithin can
supplemented by other liquid components for viscosity control (STERNPHIL 450), lecithin can be
distributed on the surface of dry powders or spraydried (STERNMULS), it can be de-oiled
(CENTROLEX) or the valuable phosphatidylcholine can be enriched by fractionation
(STERNLIPID).

Sta ge2 : So lae

ST A N D A R D I Z A T IO N

Filtra tio n
Fluid iz ing B act.
D eo do rizatio n
C ontro l
B act.contro l
ST E RN C IT H IN F-1 0 ST E RN PRIM E N -10

H yd ro lyzatio n A cety lizatio n C o m po und ing Spra y-dry ing D eoiling Fractio na tio n

H ydro ph ilic H ydro p hilic A ct ive E ncapsu lat io n O il-fre e P C /P E /P I/P A -

lyso -lecit hin P E - reduced sub stance o f lec it hin pu re lec it hin enric hed
enric hed enric hm e nt w ith carriers p o w der/g ranu late lecit hin fract io ns

ST E RN PH IL E ST E RN PHIL C A ST E RN PHIL 4 50 ST E RN M U LS C E N T RO L E X ST E RN L IPID

Table 6: Refining of Lecithin

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Introduction to the use of Lecithins

Individual Proces Steps for Lecithin – De-oiling

Table 7 shows the de-oiling of lecithin. The phospholipids are insoluble in acetone and thus
acetone allows an extraction of the inactive 40 % vegetable oil of the crude lecithin. The de-oiled
lecithin is obtained after evaporation of the acetone. The extraction can either be a batch- or a
continuous process. Table 8 shows the free flowing deoiled lecithin.
Deoiled lecithin has several advantages: the powder has convenient handling, it has a more neutral
taste since the unsaturated fatty acids of vegetable oil has been removed; deoiled lecithin is more
hydrophilic than standard lecithin.

Table 7: De-oiling of Lecithin

C ru d e le c ith in

A c e to n e E x tra c tio n

B e lt d ry in g

S ie v in g

P a c k a g in g

D e o ile d le c ith in
P o w d e r / G ra n u le s

Table 8: Free Flowing Deoiled Lecithin

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Introduction to the use of Lecithins

Individual Proces Steps for Lecithin – Hydrolysis

Table 9 shows the principles of enzymatic hydrolysis of phospholipids. Food grade enzymes are
used that allow selective hydrolysis of the fatty acids in the “2” position. The process conditions
determine the extent of the hydrolysis as well as the relative hydrolysis of the different kinds of
phospholipids. From an application point of view it is important to differentiate between low,
medium and high “degree of hydrolysis”. This degree of hydrolysis is traditionally defined as
content of hydrolysed phosphatidylethanolamine (PE) divided by total PE (unchanged and
hydrolysed PE). Note, that this definition does not consider the hydrolysis of any other
phospholipid isomer. It is a serious complication that HPLC analysis of phospholipids is still not
fully quantitative and reproducible, and that the only accurate method of analysis is the expensive
31
P-NMR method (nuclear magnetic resonance of the phosphorous 31 isotope). The resulting
lecithin is deliberate mixtures of phospholipids with either one fatty acid (Lysophospholipids) or
two fatty acids.
Hydrolysed lecithin has several advantages: it is more hydrophilic depending on the “degree of
hydrolysis” and this allows the use of lecithins in cream emulsion types as well as in frying
margarines; the “monoglyceride like structures” with only one fatty acid are much more effective
in bakery products for “softness” or longer shelf life.

Table 9: Hydrolysis of Lecithin

P h o s p h o lip a s e A 2

O 5 0 - 70 °C O
C H2 O C R1
C H2 O C R1
O O
R2
C O CH + H 2O HO CH + HO C R2

O O

C H2 O P O X C H2 O P O X

O- O-

p h o s p h o lip id + w a te r ly s o p h o s p h o lip id + f a tty a c id

D e g r e e o f h y d r o ly s is : 2 0 - 6 0 % , d e p e n d in g o n r e q u ir e m e n t
in c r e a s in g h y d r o p h ilic ity

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Introduction to the use of Lecithins

Individual Proces Steps for Lecithin – Fractionation

Table 10 shows the principle of fractionation. Phosphatidylcholine PC is relatively more soluble in

ethanol than all other phospholipids. This allows a semi quantitative fractionation of PC which can
be decanted from a “bottom fraction” with relatively less PC, the so called PE-fraction. It is
possible to obtain PC contents in the range of 30-50 % by this process. Further fractionation require
the more expensive chromatographic separation techniques that allow semi commercial production
of 80 % Phosphatidylcholine which contrary to common belief about lecithins is a solid material at
usual temperatures and very difficult to handle in practice unless sprayed on a carrier.
Fractionated lecithin has several advantages: The PC-fraction is choline enriched for dietary
purposes; it has its own characteristic Hydrophilicity and emulsification properties; it is less
sensitive to Calcium in hard water; it is less sensitive to browning on extended heating. The PE-
fraction find special uses in emulsification and baking applications.

Table 10: Fractionation of Lecithin

C r u d e L e c ith in

A lc o h o l
A lc o h o l so lu b le F r a c tio n a tio n A lc o h o l in s o lu b le
fr a c tio n P C -4 0 fr a c tio n P I-3 F

C h r o m a to g r a p h ic
se p a r a tio n
A lc o h o l so lu b le
fr a c tio n P E -5 F
P C -8 0 Iso la te

B le n d in g w ith c o c o a b u tt e r S p r a y - d r y in g o n c a r r ie r

p u r e P C fr a c tio n p u r e P C fr a c tio n
w ith c o c o a b u tte r o n m a lto d e x tr in

Individual Proces Steps for Lecithin – Hydroxylation & Acetylation (Non E 322)

Information on these process steps is added in order to complete the review. These types of
lecithins are not permitted for foods in Europe, albeit they are allowed for foods in North America.
In Europe they are used in technical applications.
Hydroxylation of the unsaturated fatty acids of the phospholipids is made in the presence of
peroxide and organic acids resulting in the highest possible lecithin Hydrophilicity. Hydroxylated
lecithin is superior for emulsification of cakes and cookies, but can only be used in North America.
Acetylation of the amino group in phosphatidylethanolamine is achieved by reaction with acetic
anhydride resulting in better resistance to browning on heating as well as in different functional
properties. Acetylated lecithin finds use in Europe for “leather tanning”.

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Introduction to the use of Lecithins

Individual Proces Steps for Lecithin – Combinations of Process Steps

Lecithin comes in many different types: refined, deoiled, hydrolysed and fractionated. Furthermore
it is possible to combine any of these processes to make for instance hydrolysed-deoiled lecithin or
fractionated-deoiled lecithin.
When lecithin has been investigated scientifically for its functionality then most often there are no
references to the nature of the specific lecithin tested, even at academic levels ! For example there
are many examples of excellent bakery work with lecithin with specific mentioning of the types of
conventional emulsifiers tested, but with no mentioning of the “lecithin” tested ! In these cases one
should assume that only standard lecithin was tested – and even standard lecithin varies. No
wonder lecithin suffers from too little recognition for its many attributes.
The point of modifying lecithin is precisely to obtain “tailor-made” properties - within one single
E-number. The ability to cover a wide span of applications is quite unique and not like any other
emulsifier. The best simple illustration of this is the range of HLB values in table 11. HLB is
Hydrophilic Lipophilic Balance value designed for differentiation of emulsification properties of
emulsifiers – in simple water/oil systems. At a glance one can tell that the various processes for
lecithin creates “tailor made” properties from water-in-oil emulsification (margarines) to oil-in-
water emulsification (creams) all within the same E-number. In applying HLB values the food
technologist should remember, that the HLB system does not consider the interaction of other
common food components for example caseinate, and it does not at all describe non-emulsification
properties, such as starch interactions in bakery products, viscosity reduction in chocolate products
and release properties in baking or frying.

W/O 2 4 6 8 10 12 O/W

PI-3F
PI-3F Hydroxylated
fraction Hydroxylated
fraction

Standard
Standard Hydrolysed
Hydrolysed

PE-5F
PE-5F PC
PC
fraction
fraction fraction
fraction
Lecithin/
Lecithin/hydrophilic
hydrophilic
emulsifier
emulsifier

Acetylated
Acetylated Oil
Oilfree
free

Table 11: HLB Values of Modified Lecithins

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Introduction to the use of Lecithins

Analytical Comparison of Processed Lecithins

After the thorough review of lecithin manufacturing, proces steps and chemistry we can now look
at the analytical comparison of table 12. Obviously the content of active phospholipids increases by
40 % after deoiling and clearly there is an enrichment in phosphatidylcholine after fractionation. In
addition to 40 % vegetable oil the native lecithin also contains about 15 % glycolipids and
carbohydrates. It is not commercially possible to remove these components but generally they are
not disturbing the functionality of lecithin. However these components cause characteristic haze or
precipitation if lecithin is re-dissolved in oils and kept over longer times.
Lecithin is traded on the basis of the content of phospholipids measured as Acetone Insolubles or
AI. The AI must be legally minimum 60 %. Table 12 also show some typical values of Acetone
Insolubles which obviously are very high for deoiled lecithin.

Typical % Values

Standard Deoiled Fractionated

COMPONENTS Lecithin Lecithin Lecithin
PHOSPHOLIPIDS
Phosphatidylcholine PC LPC 16 25 39
phosphatidylethanolamine PE LPE 13 20 8

Phosphatidylinositol PI LPI 10 15 3

Phosphatidic acid PA LPA 6 9 1

Other PL 3 5 1

GLYCOLIPIDS
Sterolglycoside 7 10 6
Galactodiglyceride 4 6 3

COMPLEX
CARBOHYDRATES
Sucrose 1 2 1

Raffinose ½ 1 ½

Stachyose 2 3 1

ACETONE INSOLUBLES AI. 62 96 64

NEUTRAL OIL 37 3 35

WATER <1 <1 <1

Table 12: Analytical Comparison of Soya Lecithins

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Introduction to the use of Lecithins

Functionalities and Benefits of Lecithins

We are now ready to appreciate the many functionality’s and benefits and to work with different
lecithins. Table 13 shows the importance of selecting the type of processed lecithin that suits the
desired functionality. As stated earlier, one can not just test “a lecithin” and conclude solely on that
basis.

A pplication Funcionality T ype of L ecithin

V olum e Im provem ent
A nti-staling
B aked goods H ydrolyzed & D eoiled
Fat D ispersion
M achinability
V iscosity M odification
C hocolate Standard Lecithin & Fractions
Y ield Point R eduction
Ice C oating W ater Entrapm ent Fractions
Instant D rinks C ompounded Lecithin & D eoiled
W etting & D ispersibility
D airy & C ocoa H ydrolyzed
Em ulsification Standard Lecithin
M argarine/Spreads
A ntispattering H ydrolyzed and Fractions
Standard Lecithin
Separation
R elease A gents H ydrolyzed & D eoiled
Ease of cleaning
A cetylated & H ydroxylated

Table 13: Functionality of Modified Lecithin in Foods

Table 14 offers an overview of commercial lecithins in relation to specific applications and desired
benefits.

Type A p p lic a t io n B e n e f its

R e fin e d F lu id F a tty P o w d e rs , B a k e r y , W e ttin g , E m u ls ify in g ,
STERNM ULS, M a rg a rin e , D re s s in g s , D is p e rs in g , R e le a s e ,
S T E R N P H IL C o a tin g s , P a in ts .... L u b ric a tin g ....
R e fin e d P o w d e r B re a d , W a fe rs , B is c u its , S h e lf L ife E x te n s io n ,
STERNM ULS, P a s try , S a u c e s ..... S ta b iliz in g ,D is p e rs in g ,
L E C IF L O W , E m u ls ify in g .....
STERNBAKE
D e o ile d F a tty P o w d e rs , B a k e r y , A ll th e a b o v e , P L U S
CENTRO LEX C o n fe c tio n e ry , D ie te tic c o n v e n ie n c e o f fo r m ,
S u p p le m e n ts , N u tritio n a l p u rity , b la n d n e s s .
P ro d u c ts .....
F ra c tio n s D ie te tic F o rm u la s , N u tritio n a l A ll th e a b o v e , P L U S
C EN TR O LEX FP P ro d u c ts , In fa n t F o rm u la s , h ig h C h o lin e le v e ls fo r
N e u tra l ta s te p ro d u c ts . h e a lth .

Table 14: Benefits of Lecithins in Foods

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