10.

Lipids

Prepared by
Joyce Tiong
For UEMK 1013
October 2012
 Introduction
In organic chemistry study, compounds usually are
classified according to their functional groups.

Lipids are classified by solubility, not structure.

Lipids can be extracted from cells by non-polar organic

solvents.

Complex lipids are easily hydrolyzed to simpler

constituents.

Lipids are extracted from cells & tissues by non-polar

organic solvents.
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 Examples of Lipids
Most complex lipids are esters of long-chain carboxylic
acids called fatty acid:
Waxes (esters of long-chain alcohols)
Triglycerides (esters of glycerol)

Simple lipids are not easily hydrolyzed by aqueous acid or

base.
Steroids
Prostaglandins
Terpenes

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Examples of Lipids

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 Wax

Ester of long-chain fatty acids + alcohol.

Cetyl palmitate

Most natural waxes serve as protective coats

for plant leaves, insects exoskeletons,
mammals fur, birds feathers.

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 Examples of Waxes
Natural waxes:
Beewax: used by bees to form their honeycomb.
Carnauba wax: shoe polish, dental floss, sweets.

Wax sculptures of
Michael Jackson and
Adolf Hitler in Madame
Tussauds Wax Museum,
London.

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 Triglycerides
Ester derived from glycerol with three fatty
acids.

Categorised into fats and oil.

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 Fat
Solid at room temperature
Mostly derived from mammals

Oil
Liquid at room temperature
Mostly derived from plants and cold-blooded
animals (e.g. fish oil)

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 Fat and Oil
Most fats are saturated fatty acids; while oil are
unsaturated.
Unsaturated triglycerides have lower melting
point as they do not pack well in a solid lattice.

Well packed,
high melting
point.

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 Fatty acids
Unbranched carboxylic acids with 12-20
carbons.
Some have saturated carbon chain, while
others have one or more C=C bond.
Melting point increase with the increase in
molecular weight.
Unsaturation and cis-double bond greatly
decreases melting point.

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Examples of Fatty Acids

Lauric acid

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 Reactions of Fatty Acids
Fatty acids undergo similar reactions to
normal carboxylic acids.

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 Essential Oil
Volatile, fragrant oil from plants.
Obtained from over 3,000 plants.
Diverse sorces: flower (rose, jasmine), spices
(cinnamon, ginger), pine oil, turpentine, citrus
fruit peels.
Complex mixture with every major functional
groups.
Isolated by steam distillation, extraction or
mechanical expression of the plant material.
Used for flavouring, incense and medical
purposes.
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 Examples of Essential Oil (I)
Cannabis flower oil
Food flavouring, beverages, perfume, cosmetics, soaps and
candles.
Caraway oil
Food flavouring, mouthwash and toothpaste.
Citronella oil
Insect repellent
Clove leaf oil
Topical dental anesthetic.
Cranberry seed oil
cosmetic
Fennel seed oil
Treat colic in infants
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 Examples of Essential Oil (II)
Lemon oil
Antiseptic and in cosmetics
Mentharvenis / mint oil
Flavouring in toothpastes, mouthwash, aromatherapy,
pharmaceuticals
Oregano oil
Treat digestive problems
Rosemary oil
aromatherapy
Yarrow oil
Relieve joint pain

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 Soap hydrophilic

hydrophobic

A soap molecule has a high electron density

head which is hydrophilic (attracts water) and
hydrocarbon tail which is hydrophobic (repels
water).
Soap forms micelles in water, with the
hydrophilic head sticking outwards and
hydrophobic tail inwards.

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 Grease in Soap
Grease is emulsified when soap forms a micellar
structure: hydrophilic head sticks to the water,
hydrophobic tail sticks to the grease.
Results in two insoluble phases called emulsion.

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 Formation of Soap - Saponification
Hydrolysis of ester linkages in fats and oil, in
the presence of a base catalyst.
Made by boiling animal fat / vegetable oil with
NaOH.
O CH2 OH
CH2 O C (CH2)16CH3 CH OH glycerol
O
CH2 OH
CH O C (CH2)16CH3 + 3 NaOH
O O
+-
CH2 O C (CH2)16CH3 + 3 Na O C (CH2)16CH3
sodium stearate
tristearin

A soap 18
 Limitations of Soap (I)
Tend to precipitate out in hard water.
(Hard water: acidic water rich in calcium, magnesium or iron)
In acidic water, soap molecules are
protonated.
Without ionized carboxylate group, fatty acid
floats on the top, forming white precipitate
called acid scum.
O O
n(H2C)H3C O C O- +Na + H+ n(H2C)H3C O C OH + Na+
a soap acid scum 19
 Limitations of Soap (II)
When the water is rich in Ca2+ ions, soap forms
insoluble white precipitate.
O O
2 CH3(CH2)n O C O- +Na + Ca+2 [CH3(CH2)n O C O]2Ca + 2 Na+
a soap hard water scum

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 Phospholipids
Lipids that may form bilayer.
Most common phospholipid:
phosphoglyceride

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 Phosphoglycerides
The simplest class of phosphoglycerides are
phosphatidic acids, which consists glycerol
esterified by two fatty acids and one
phosphoric acid group.
Although it is often drawn in its acid form, a
phosphatidic acid is actually deprotonated at
neutral pH.

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 Lipid Bilayer / Phosphoglycerides
Cell membranes are a bilayer of phosphoglyceride.
They aggregate into a bilayer membrane with polar
heads exposed to the aqueous solution, and
hydrocarbon tails within.
Acts to restrict flow of water and dissolved substances.

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 Steroid
Compound with tetracyclic androstane ring system.
Four rings (A, B, C, D), beginning with the ring at the
lower left and the carbon atoms numbered beginning
with A ring and ending with the two angular methyl
groups. 18
12 CH3
11 17
19
CH3 C 13 16
1 D
2 9 14
A, B and C: cyclohexane rings 10 8 15
D: cyclopentane ring A B H
3 5 7
4 H 6 24
 Cis-- and Trans
Cis Trans-- Steroids
Common steroids have either a cis- or trans- at
the A-B ring junction.
Most steroids have all trans- structure: hence are
stiff, flat molecule with two axial methyl groups
perpendicular to the plane.

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 Examples of Steroids

Dietary cholestrol
Sex hormones: estradiol and testosterone
Anti-inflammatory drug: dexamethasone
Vitamin D

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 Cholesterol
Can be obtained by extraction of almost all
animal tissues.
Intermediate in the biosynthesis of all steroids of
the body. Hence, it is necessary to have
cholesterol in our body.
High levels of blood cholesterol may cause
development of arteriosclerosis (hardening of
arteries), causing heart attacks.
May be classified into chylomicrons, high-density
lipoproteins (HDL) and low-density lipoproteins
(LDL).
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 CH3

Cholesterol CH3 H
17 H

3 H H
5
6
HDL: HO
H

Carries lipids from the tissues to the liver for

degradation and excretion.
a.k.a. Good cholesterol.
LDL:
Carries biosynthesised lipids from the liver to the
tissues.
a.k.a. bad cholesterol.
Chylomicrons:
transport dietary lipids from the intestines to the
tissues.

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 Sex Hormones
CH3 OH CH3 OH
H H
CH3 H H

H H H H
O HO
testosterone estradiol

Female hormone has an aromatic ring and one less methyl

group than the male hormone.
Testosterone is converted to estradiol in the ovaries.
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