Fatty Acids

Fatty acids, esterified to glycerol, main constituents

The industrial exploitation of oils and fats, is based on
chemical modification.
fatty acids = essential components of lipids are aliphatic
carboxyl acids
Two main groups:
 Saturated
 Unsaturated
Natural fatty acids contains, with extreme exception, even
number of carbon atoms
 4 – 28 in fats
 Higher number of carbon atoms are found in waxes
Chain is usually straight, unbranched, unsubstituted

1
 Saturated fatty acids
The common names of these acids indicate the
specific source in which they are especially abundant
Or from which they have been isolated
Physical properties vary with the number of carbon
atoms
Acids with fewer than 12 carbon atoms are
conventionally called “the volatile fatty acids” since
they can steam distilled with relative ease
Members with carbon atoms higher than 10 are solids
at room temp
Solubility in water decreases with the chain length
Acids with more than 10 carbons are practically
water-insoluble 2
 Unsaturated fatty acids
Oleic and linoleic acid, account for 34% and 29% of all the
edible oils produced by man annually
Acids with two or more double bonds are known as poly-
unsaturated acids
Poly-unsaturated fatty acids perform certain important
physiological functions, but
 they cannot be synthesized in the body and must be supplied in the food
are referred to as “essential fatty acids”
 Linoleic acid is the most abundant member of this group
Unsaturated fatty acids have considerably lower
melting points than corresponding saturated fatty
acids
Thus oleic acid with 18 carbon atoms is a liquid at
room temp
The industrial hardening by hydrogenation is based on
the saturation of the double bonds 3
 Isomerism in fatty acids
Three possible types of isomerism
1) Single isomerism of a straight chain versus
branched chain
2) Isomerism caused by the position of the double
bond in the chain
 In the case of more than one unsaturated double bond,
this type of isomerization can give two distinct kinds of
systems, conjugated and non-conjugated
3) cis-trans (geometrical) isomerism
 In nature most unsaturated fatty acids occur
mainly in the cis-form
 Trans??
4
Structure of Fatty acid

5
Fatty Acids
Fatty acids are almost entirely straight chain aliphatic
carboxylic acids.
Includes most natural fatty acids C4 to C22
Naturally occurring fatty acids share a common
biosynthesis.
The chain is built from two carbon units, and cis
double bonds are inserted by desaturase enzymes at
specific positions relative to the carboxyl group.
Even-chain-length fatty acids with a characteristic
pattern of methylene interrupted cis double bonds.
A large number of fatty acids vary in chain length and
unsaturation
Two numbers separated by a colon give,
respectively, the chain length and number
of double bonds: octadecenoic acid with 18
carbons and 1 double bond is therefore
18:1.
The position of double bonds is indicated in
a number of ways:
 explicitly, defining the position and
configuration; or
 locating double bonds relative to the methyl or
carboxyl ends of the chain.
Fatty acids in fats and oils
Major sources
 Structure and stereospecific

Simplified structures are often used;

e.g., 1-palmitoyl-2-linoleoyl-3-oleoyl-sn-glycerol is abbreviated as
PLO.
Most natural triacylglycerols do not have a random
distribution of fatty acids on the glycerol backbone.
In plant oils, unsaturated acids predominate at the sn-2
position, with more saturated acids at sn-1 and sn-3.
The distribution of fatty acids at the sn-1 and sn-3
positions is often similar, although not identical.
However, a random distribution between these two
positions is often assumed as full stereospecific analysis
is a time-consuming specialist procedure.
In animal fats, the type of fatty acid predominating at
the sn-2 position is more variable; for example,
palmitate may be selectively incorporated as well as
unsaturated acids
Only oils that are rich in one fatty acid contain much
monoacid triacylglycerol, for example, olive, sunflower,
and linseed oils containing OOO, LLL, and LnLnLn,
respectively.
Physical property
The melting behavior of triacylglycerols generally reflects
that expected from the fatty acid composition;
triacylglycerols rich in long-chain are high melting, and
those rich in polyunsaturated acids are lower melting.
The situation is complicated by the possibility that the
fatty acids can be distributed in different molecular
species with different melting points.
Oils with similar fatty acid composition may have different
 solid fat content,
 polymorphic forms, and

 melting behavior

as a result of a different triacylglycerol composition and

saturated acids
Saponification value and iodine
value
Saponification value (SV) or equivalent (SE) and
Iodine value (IV) are specifications used to
monitor processes.
SE, expressed as grams of fat saponified by one
mole of potassium hydroxide, is
 an indication of the average molecular weight/ chain
length
IV, expressed as the weight percent of iodine
consumed by the fat in a reaction with iodine
monochloride,
 an index of unsaturation
Unsaponifiable matters
Unsaponifiable matter. Oils and fats contain variable
amounts of sterols, hydrocarbons, tocopherols,
carotenoids, and other compounds, collectively
referred to as unsaponifiable matter
Some of these minor components are removed
during refining, and the resulting concentrates may
be useful byproducts, for example, tocopherol
antioxidants.
Characteristic fingerprints of minor components,
particularly phytosterols and tocopherols, are also
used to authenticate oils and detect adult
HYDROLYSIS, ESTERIFICATION,
AND ESTER EXCHANGE
Reactions converting acids to esters or vice
versa and the exchange of ester groups
For microscale preparation of methyl esters
for GC analysis to the industrial production of
oleochemicals and biodiesel.
The exchange of groups attached to the fatty
acid carboxyl is usually an equilibrium
process.
Increasing interest in the use of lipase for
large-scale reactions.
Enzyme reactions require milder conditions,
less solvent, and give cleaner products—
attributes of ‘‘green chemistry.’’
Enzymes can exert regio- or stereospecific
control over reactions
offer a degree of selectivity for particular
fatty acids, not observed with acid or base
catalysts.
Fat splitting
The industrial production of fatty acids uses the
direct reaction between water and fats, which
proceeds rapidly at 250C and 2–6 MPa (20– 60
bar).
Under these conditions, water is moderately
soluble in the oil phase, and stepwise hydrolysis
of the triacylglycerols proceeds without the aid
of a catalyst.
The reaction is carried out with a
countercurrent of water that removes the
glycerol formed, resulting in 99% conversion to
fatty acids.
Glycerol is recovered from the aqueous phase.
Esterification
Fatty acids are converted to esters by
reaction with an excess of alcohol using an
acid catalyst or a lipase. For the preparation
of methyl esters for GC analysis, boron
trifluoride, sulfuric acid, or anhydrous
hydrogen chloride in methanol are
commonly used.
Reaction is complete in 30 minutes at reflux.
Propyl and butyl esters are prepared in a
similar way with the corresponding alcohols.
Ester Exchange Reactions
The fatty acid or alcohol groups present in an
ester can be exchanged in a number of ways:
by reaction with an excess of other fatty
acids (acidolysis), alcohols (alcoholysis), or
other esters (interesterification).
These reactions provide routes by which the
composition and properties of oils and fats
can be modified.
Acidolysis. This reaction can be acid or
enzyme catalyzed and may be used to modify
triacylglycerol composition.
Acidolysis of an oil containing only C16 and
C18
fatty acids with fatty acids rich in lauric acid
(e.g., from palm-kernel oil) results in a
triacylglycerol enriched in medium-chain fatty
acids.
Interesterification.
Interesterification is the intra- and intermolecular
exchange of fatty acids on the glycerol backbone of
triacylglycerols.
To produce triacylglycerols with different properties
either from an individual oil or a blend of oils.
The molecular species of natural triacylglycerols
shows greater or lesser selectivity in the distribution
of fatty acids between the sn-1 and sn-3 and the sn-
2 positions
Lipase catalyzed interesterification may alter the
distribution of molecular species in a more selective
way.
 Fats & Oils – Physical properties
Pure triglycerides are colourless, tasteless, odorless and water
insoluble substances
Any color, odor and taste in fats and oils are due to non-
triglyceride components
The solid-liquid transition of fats is of importance
Triglycerides containing a large proportion of unsaturated fatty
acids – have lower melting points
 most vegetable oils are liquid at room temp
Glycerides can exist in a number of different crystalline forms –
polymorphism
 Hence the phenomena of multiple phase transition (melting) points
The crystalline characteristics and melting behavior of fats also
on the distribution of fatty acids among the triglyceride
molecules
23
 Fats & Oils - Hydrolysis
Glycerides are easily cleaved into fatty acids and glycerol by
heating with alkali
I. The resulting alkaline salts of fatty acids are the well known
“soaps” hence the name “saponification” – given the hydrolytic
cleavage
II. The de-esterification of triglycerides is also catalyzed by the
enzyme lipase
The enzyme is widespread in all lipid-containing tissuesLipases
specificity may involve
 Selectivity towards different fatty acids
 Preference towards the position of the ester bonds on the glycerol
backbone
The enzyme responsible for the digestion of fats, pancreatic
lipase, has some preference for the 1,3 position and for shorter
chain fatty acids
As ester bonds are gradually broken, intermediate products, di-
and monoglycerides are formed 24
 Hydrolytic rancidity
Lipases react in heterogenous systems such as
emulsions of glycerides in aqueous media
Action occurs at the interface between phases
The most significant consequence of lipase activity in
foods is the development of a harsh, acrid taste as a
result of free fatty acid liberation
The short chain volatile fatty acids (butyric acid) also
contribute their characteristic odor to foods
Quite common in olives, milk, cream, butter, nuts
As lipase activity occurs on the interphase, hydrolytic
rancidity is more rapid in more finely dispersed
emulsions, homogenized milk/cream
A high free fatty acid level in edible oils is
objectionable and must be removed in refining 25
 Fats & Oils - Oxidation
Tendency of fats and oils to become rancid is well
known
Serious rancidity results from oxidative reactions
The susceptibility of fats and fatty acids to oxidation is
associated with the presence of unsaturated bonds
Spontaneous nonenzymic oxidation of lipids exposed
to air is – autoxidation
 Most frequent type of oxidative deterioration of lipids in
manufactured foods
Lipid oxidation is catalyzed by the enzyme lipoxidase

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 Phospholipids
Lipids containing phosphoric acid
Difficult to classify in view of its wide heterogeneity
Phosphoglycerides is the most important
(Structure below)
 Two hydroxyls of the glycerol residue are esterified with fatty acids
 The third hydroxyl is bound to phosphoric acid which in turn is
ester-linked with X-OH, usually an amine alcohol

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Phospholipids
The phosphoric acid end of the molecule is strongly
polar hydrophylic
The fatty acid “tails” are non-polar
This dual structure (amphiphatic) makes the
phosphoglycerides valuable surface active agents and
emulsion stabilizers
Phosphoglycerides are important cell wall constituents

Phosphoglycerides in cell wall 28

 Role of lipids in Foods
Nutritionally – main function to supply energy
Nutritional caloric content of fats is very high
 9 cal/g compared to 4 in carbohydrates/proteins
Dietary fats are important as vehicles for fat soluble
vitamins and as a source of essential fatty acids
Fats are the preferred form of long-term storage fuel
in living organisms
Many lipids are important structural elements of
biological membranes, because of their special surface
properties

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 Role of lipids in Foods
The role of lipids in sensory characteristics is mainly
connected with texture and rheological properties
Refined fats have no taste of their own
 The presence and physical form (dispersion) of fats,
determine the taste sensation and mouth feel
 Flow properties of the food in the mouth are controlled by
the fat fraction
 Spreadability, coating of the tongue, sensation of
swallowing, viscosity

30
Lipid Oxidation, Introduction
Off flavours are generally described as “rancidity” in fat-
containing foods
The principal source of “rancidity” in foods is the autoxidation of
lipid compounds
Autoxidation: Defined as the spontaneous oxidation of a
substance in contact with molecular oxygen
The fatty acid alkyl chain is susceptible to oxidation both at
double bonds and adjacent allylic carbons.
Free-radical and photooxidation at allylic carbons are responsible
for deterioration of unsaturated oils and fats, resulting in
 rancid flavors and reduced nutritional quality,

31
 Introduction
Consequences of lipid autoxidation
 Most significant – rancidity
 Also flavour deterioration
 Colour is affected – through accelerated browning
 Nutritional value is impaired
 Toxicity may occur
 Texture may change due to side reactions between proteins and the
products of fat oxidation
Oxidative deterioration of lipids may be considered as a
spoilage factor affecting all the aspects of food acceptability
Lipid compounds most susceptible to autoxidation
are the unsaturated fatty acids
 Especially those with more than one double bond
Autoxidative deterioration of lipids resembles
somewhat non-enzymic browning 32
 Mechanism
1: Initiation 2: Propagation 3: Decomposition 4: Termination

In the first stage a few molecules of the lipid RH are

sufficiently activated by
 heat, light or metal catalyst… to decompose into the
unstable free radicals R• and H•
In the presence of molecular O2 the possibilities of
recombination include an encounter between the free
radical and R• & O2
 resulting in the peroxide radical ROO•
The radical then reacts with a fresh molecule of lipid,
RH, producing the hydroperoxide ROOH and a free
radical R• through which the chain reaction is
propagated 33
 Mechanism
The reaction proceeds and more lipid molecules are
transformed to hydroperoxides
The reaction is terminated when free radicals
combine with other free radicals or with free radical
inactivates (X), to yield stable compounds which
accumulate in the system
The hydroperoxide enter a series of reactions leading
to more free radicals and stable final products
 Final products include short chain carbonylic compounds
responsible for the rancid flavour and for side reactions to
overall deterioration

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 Hydroperoxide
The various regions of the lipids are not equally
susceptible to activation
The methylenic group, adjacent to a double bond of a
fatty acid, is particularly labile
hydroperoxide is the primary products of lipid
autoxidation
 They are non-volatile, odorless and tasteless
 Formation and accumulation are measured as the increase
in the “peroxide value”
 Indicates the progress of autoxidation, but not
necessarily the appearance of rancidity

35
 Degradation of Hydroperoxides
Hydroperoxides are relatively unstable
 As their concentration in the system
increases, they begin to decompose
On possible reaction is the monomolecular
decomposition of hydroperoxides into an alkoxy
and hydroxy radical

36
 Polymerization
Polymerization
 One of the consequences of lipid oxidation is the
formation of viscous, gum-like or solid polymers
(resins)
 “Drying” of highly unsaturated oils used in paints is
the result of such polymerization
 May occur through direct contact with free radicals
or through other reactions

37
 Kinetic aspects
The course of autoxidation in lipids is
experimentally followed by measuring the;
 Accumulation of peroxides
 Rate of oxygen uptake
 Concentration of secondary reaction products
 Organoleptic evaluation

38
 A. Peroxide value
One of the most widely used concepts in lipid
chemistry
 measure of peroxide concentration of oil

 expressed as milli-equivalents of peroxide

oxygen per 100 g of fat

 Environmental factors፡ Temperature፣

Light፣ Oxygen፣ Moisture፣ Ionizing radiations፣

Catalysts፣ Antioxidants

39
B. Rate of oxygen uptake
More meaningful measure of the rate of
oxidation
method to determine
 reaction of the oxidized fat with thiobarbituric acid
(TBA)
TBA reacts with oxidized fats to give a red
colored complex which is measured by
spectrophotometer
TBA test correlates well with the degree of
rancidity
40
 … B. Rate of oxygen uptake
When the peroxide value (or oxygen uptake)
of an autoxidizing lipid is followed, a curve are
drawn
At first the PV increases slowly, uniform rate
As soon as the PV reaches critical value, a
sudden and drastic increase in rate is recorded
The first slow phase is termed “induction
period”
The autocatalytic nature of this course is
explained on the basis of the free radical chain
mechanism explained
41
 … B. Rate of oxygen uptake
During the induction period initiation and propagation
occur
Since for each free radical which is transformed to a
hydroperoxide one new free radical is formed
The reaction proceeds at a slow uniform rate
As the concentration of of hydroperoxides increases,
hydroperoxide decomposition reactions take place at
an in increasing rate
These reactions generate more free radicals than
needed for the propagation of the chain reaction at a
constant rate - Autocatalytic

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a. Heavy Metals as Catalysts
The main effect of these trace metals is to increase
the rate of hydroperoxide decomposition, and hence
the rate of free radical generation
Hydroperoxides are decomposed and free radicals RO
and ROO are formed as the metal oscillates between
its two oxidation states
The source of heavy metal ions in foods may be contamination
 Equipment, piping, packaging materials, environmental contaminants
 Or natural food components
Most important metal-containing natural food components are
the metallo-porphyrin substances (hematin compounds)
 Hemoglobin, myoglobin

43
 b. Enzymes as Catalysts
Catalyst of lipid oxidation in some foods –
lipoxidase
Lipoxidase catalyzes specifically the direct
oxidation of poly-unsaturated fatty acids
containing a cis-cis 1,4-pentadiene group
(linoleic and linolenic acid)
This enzyme is found in oilseeds, legumes,
cereals, leaves
If it is not inactivated by heat (blanching),
lipoxidase may cause rapid development of off-
flavours in frozen and dehydrated veggies
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 Antioxidants
Antioxidants are substances that retard
autoxidation
A substance may act as antioxidant in variety of
ways
 Competitive binding of oxygen
 Retardation of free radicals
 Inhibition of catalysts
 Stabilization of hydroperoxides
All these mechanisms are found in food systems
– the most important is blockage of propagation

45
 Antioxidants
Antioxidation action increases the length of the induction period
The induction period increment is roughly proportional to the
concentration of antioxidant up to a certain level
Excess concentration of antioxidant is ineffective or may even
cause reversion of the protective affect
One of the principal classes of antioxidants are the natural or
synthetic phenolic compounds
Synthetic phenolic antioxidants approved for food use include
 butylated hydroxyanisol (BHA)፣ butylated hydroxytoluene (BHT) and
propyl gallate (PG)
BHT and BHA are quite volatile at frying temp
PG forms dark compounds with iron ions

46
Natural antioxidants
(a) a-tocopherol,
(b) carnosic acid,
(c) sesamol. Synthetic antioxidants
(d) butylated hydroxyanisole (BHA),
(e) butylated hydroxytoluene (BHT), and
(f) propyl gallate.
a. Lipid autoxidation in Food Systems –
Oxidized flavors
 Immediately recognizable effect of lipid oxidation
in foods is the development of undesirable odors
and off-flavors
 “rancid” products are largely short-chain
carbonylic compounds formed as a result of
peroxide decomposition
 The overall organoleptic nature of rancidity
depends somewhat on the system

48
 a. … Oxidized flavors
 The rancidity in low-moisture foods is usually described as
“old oil” or “tallow-like”
 Lipid oxidation in water-rich foods such as milk resutls in

“cardboard-like” off-flavors, known as “oxidized milk flavor”

“Flavor Reversion”
 Oxidative deterioration process of great importance in some vegetable
oils – soybean oil
 Freshly refined soybean oil is practically tasteless
 Upon storage under improper conditions of extensive exposure to air, high
temp
 Off-flavors ranging from “beany” to “fish-like” are quickly formed
 The term inversion implies that the refined oil reverts to its raw,
unrefined form – incorrect
 The “reversed” flavor is due to newly formed compounds unrelated to
the flavor-bearing components of the raw oil

49
 b. Effect of Colour
Lipid oxidation may affect indirectly the colour of
foods
In carotenoids, propagation of the lipid oxidation
chain through free radicals may cause oxidative
destruction of the carotenoid pigments
This type of deterioration is important in dehydrated
vegetables and usually involves the catalytic action of
lipoxidases

50
 c. Effect on Texture
The interaction between proteins and the products of
lipid oxidation may result in changes of texture
The mechanism of interaction involves propagation of
the free radical chain to the protein system
Various groups in the protein molecule are capable of
converting to free radicals by losing a hydrogen atom
to a free radical of lipid origin
The protein “free radicals” thus formed tend to
combine by cross-linkages

51
 Lipid Oxidation at High Temp
Of interest in connection with food processing
operations involving high temp:
 Toasting, roasting, baking, frying
Most important characteristics of heated oils
are:
 Despite the accelerated rate of oxidation, peroxide
values are usually very low, due to the rapid
decomposition of the peroxides formed
 The flavor of heated oils is not rancid (unlike fats
oxidised at low temp) due to the elimination of
the volatile breakdown products by
evaporation – steam distillation effect
52
… Lipid Oxidation at High Temp
Polymerization is one of the predominant
termination processes.
The viscosity of oils increases considerably due
to the process of heating
The degree of unsaturation, measured as the
“iodine value” decreases sensibly, indicating
direct saturation of the double bonds.
Poly-unsaturated acids are affected first
Hydrolysis of the fat occurs and fatty acids are
liberated, especially in the process of frying
53
 Lipid nature of Carotenoids
Carotenoids
 Large group of pigments
 Widely distributed in the plant and animal kingdoms
 Yellow-orange to purple in colour
 Insoluble in water
 Soluble in fats and organic solvents
 Classed as Lipochrome pigments
Food products of animal origin such as milk, butter,
egg yolk, some fish and shellfish, contain carotenoids
dispersed in the lipid components

54
 Lipid nature of Carotenoids
Carotenoids are much more stable to oxidation in their
natural form than in pure systems.
Crystalline pure lycopene or a solution of lycopene n
chloroform fades in a matter of a few hours when
exposed to air, while the same pigment in its natural
form in tomatoes is quite stable
The oxidation of carotenoids and the autoxidation of
fats have many points in common and are interrelated
in food systems
Free radicals formed in the course of fat oxidation may
participate in the oxidative attack on carotenoids
The enzyme lipoxidase may also take part in
carotenoid oxidation
55
 Lipid nature of Carotenoids
Breakdown of Carotenoids
 Because of their highly unsaturated nature, they oxidize very quickly,
particularly at the double bonds
 As double bonds are saturated and finally broken down, the
characteristic color of carotenoids bleaches
 The most important factor in the oxidation of carotenoids is
the presence of oxygen or strong oxidizing agents
 The destruction is more rapid at high temp
 The effect of temperature may accelerate oxidation directly,
also render the carotenoid more susceptible to breakdown
by denaturing the protective protein
 Bleaching is more rapid in the absence of water
 Moisture content levels can have a protective effect on
carotenoids

56
 Carotenoids in Food Systems
Mixtures of natural carotenoids extracted form plant
tissues and synthetic ß-carotene are commercially
available as food colorants
 Both in the oil-soluble and water-dispersible forms
Chemical instability of carotenoids:
 Loss of carotenoids is a problem in fat rich systems
(butter/margarine), and in low moisture foods
 Loss of characteristic colour
 Formation of undesirable odors due to breakdown products

57
 Carotenoids in Food Systems
Opaque containers, package under nitrogen –
prevents destruction
Carrots – coating of starch can be sprayed on before
dehydration
The bleached colour of the carotenoids, caused by
oxidation, is often a very important indication of
deterioration in food product
 Citrus essential oils
Colour of carotenoids can be undersirable
 Bleaching of wheat flour during storage in air

58
 Lipid nature of Vitamin A
Vitamin A is now termed Retinol
In relationship with carotenoids
ß-carotenoids consists of two molecules of vit A,
bound tail to tail
ß -carotene is converted to vit A, with the help of
enzymes in the intestinal mucosa
 The name provitamin A given to B-carotene
The conversion involves oxidation at the middle point,
by a specific enzyme, ß-carotene-15, 15-
oxygenase

59
 Lipid nature of Vitamin A
A peroxide is formed
Cleavage of the peroxide yields two molecules of
retinal (the aldehyde form of vit A)
The majority of retinal is reduced to retinol by a non-
specific enzyme
Retinol is carried into the blood stream and any
amount in excess of the required level in blood is
stored in the liver, in the form of fatty-acid esters
In the blood retinol is carried by a very specific
protein, retinol binding protein

60
 Lipid nature of Vitamin A
Function of vit A is connected with vision
 In the eye, retinol, is oxidized to retinal
Retinal combines with certain proteins termed
opsins, to formvisual pigments of the retina
Vit A and β-carotene, are soluble in fats and oils
 when the oils become rancid (due to oxidation) the vitamin
suffers considerable losses
 butter or vit-enriched margarines, subjected to prolonged
storage
Vitamin can be destroyed by light
 The effect of packaging is an important factor in the
retention of vit A
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 Terpenes, Essential oils
Essential oils are widely distributed in many different parts
of the same plant
 Roots, stem, leaves, flowers, fruits
The aromatic material may be actually dissolved in the juice,
or the essential oils are secreted in numerous oils sacs or
glands located in the epicarp, adjacent to the chromoplast
Essential oils are mixture of various volatile organic substances along
with non-volatile waxy materials
The term “oil” implies that these substances are insoluble in water but
soluble in non-polar solvent
The greater part of essential oils consists of terpenoids and their
derivatives
Terpenoids are naturally occuring isoprenoid hydrocarbons (terpenes)
and their oxygenated derivatives

62
 Lipid Nature of Cholesterol
Cholesterol is the most abundant sterol of the animal
as structural element of cell membranes of many tissues in
conjunction with phospholipids
also occurs in ester combination with fatty acids
Closely related to cholesterol is lanosterol, found in the
fatty component of wool
 lanosterol is an effective fat-water binding agent, hence the use
of lanolin in “moisturizing creams”
 Lanosterol is an intermediate in the biosynthesis of cholesterol
Cholesterol also serves as a precursor in the biosynthesis of
ergosterol (vit D) and steroid hormones and bile acids
bile acids are synthesized in the liver, from cholesterol
Bile acids: emulsify fats and thus facilitate digestion and
absorption.
63