FATS and LIPIDS

Introduction
1) The term lipid is used to denote fats and fatlike
substances and is synonymous with the terms lipoids
or lipins.

2) It includes a great varieties. The main component is

triglycerides(>95%), others include phospholipids, wax,
fatty acids, cholesterin etc.

3) Lipids are usually defined as food components that

are insoluble in water but soluble in organic solvents.
4) Essential structural component of living cells (along
with proteins and carbohydrates).

5) Exist in the free form(such as fats or oil),or

associated ( combined with carbohydrates,or
protein in food).

6) Are composed of fatty acids

7) Are compounds of mostly carbon, hydrogen, and

oxygen
Some contain phosphorus
Lipids include a variety of structure types, For example
O CH3
H2C O C R CH3 CH3
O CH2OH
HC O C R'
OH
O CH3
CH(CH3)2 CH3
H2C O C R''

A fat or oil Menthol Vitamin A

(ÓÍ»òÖ¬£© (±¡ ºÉ´¼) (ά ÉúËØA£©

O H
H2C O C R H3C
O H3C H
HC O C R'
CH3 H
O
H2C O P OCH2CH2N+(CH3)3 H H
O- HO
lecithin Cholesterol
(ÂÑÁ×Ö¬) (µ¨¹Ì ´¼)
Main Functions of Lipids
•Energy Storage
•Foundation of Cell Membranes
•Cell Signalling
•Hormones
Characteristics of Lipids

1. Insoluble in water, but soluble in organic

solvents , such as ethyl oxide petroleum ether
chloroform acetone
2. Most of lipids contain ester bond, and main
section is fatty acid ester.
3. Be produced by organism, and can be used by
organism(different from mineral oil).
Classification of
Lipids
A. According to Composition
• Fatty Acids
• long chain linear hydrocarbons carboxylic acids

• Usually have an even number of C atoms (usually 12 to 20)

• The carbons are numbered starting from the carboxylic C.

• They are amphiphilic; they have a polar end and rest of the molecule is
nonpolar

• Fatty acids may be saturated (no double bonds) or unsaturated (one or

more double bonds)

• Longer chain and saturation increases melting point of FA

• FAs are ionized at physiological pH

• Lipids containing Glycerol

1. Triglycerides
• TG are the storage form of FA; most dietary fats are triglycerides
• Physiologically, TG are digested in the small intestine by the enzyme
pancreatic lipase

2. Phosphoglycerides or phospholipids
• These are lipids that contain one or more phosphate groups
• PL are the primary components of biomembranes. Other lipids in
biomembranes are glycolipids and cholesterol. Surfactants are
phospholipids, mostly phosphatidylcholine
3. Cardiolipin

4. Plasmalogen

– phospholipids with an alkyl ether at C-1 of

glycerol + FA + PO4 + an N-compound

a.) phosphatidal choline

b.) phosphatidal ethanolamine or cephalin

c.) phosphatidal serine

C. Lipids not containing Glycerol
1. Sphingolipids
a. ceramide
b. sphingomyelin
c. glycosphingolipid – no phosphorus and N-compound,
instead it contains carbohydrate units.
c.1. cerebrosides or
neutral glycosphingolipid
c.2. gangliosides or
acidic glycosphingolipid
 2. Waxes

3. Terpenes

4. Steroids

D. Lipids combined with other classes of compounds

1. Lipoproteins

2. Proteolipids
Fatty Acids

•Long-chain carboxylic acids

•Insoluble in water
•Typically 12-18 carbon atoms (even number)
•Some contain double bonds

corn oil contains 86%

unsaturated fatty acids and
14% saturated fatty acids
13
Fatty acids

•Nomenclature
• Stearate – stearic acid – C18:0 – n-octadecanoic acid

•General structure:
CH3 (CH2)n COOH n = 0 : CH3COOH n = 1 : propionic acid

n is almost always even

Fatty Acid Nomenclature
Saturated and Unsaturated Fatty Acids

Saturated = C–C bonds

Unsaturated = one or more C=C bonds

COOH
palmitic acid, a saturated acid
COOH

palmitoleic acid, an unsaturated fatty acid

Structures

Saturated fatty acids

• Fit closely in regular pattern
COOH
COOH
COOH

Unsaturated fatty acids

• Cis double bonds H H
C C

cis double bond COOH

17
Properties of Saturated
Fatty Acids

•Contain only single C–C bonds

•Closely packed
•Strong attractions between chains
•High melting points
•Solids at room temperature
18
Fatty acids classification
Properties of Unsaturated
Fatty Acids

•Contain one or more double C=C

bonds
•Nonlinear chains do not allow
molecules to pack closely
•Few interactions between chains
•Low melting points
•Liquids at room temperature
20
Fatty acid reactions

• salt formation

• ester formation
NaOH
RCO2H RCO2-Na+ (a soap)
• lipid peroxidation

-H20
R'OH + RCO 2H RCO2R'

R' O2
R R R'
H H non-enzymatic
OOH
very reactive
 Fats and Oils (Glycerides)
• fats are solids or semi solids
• oils are liquids
• melting points and boiling points are not usually
sharp (most fats/oils are mixtures)
• when shaken with water, oils tend to emulsify
• pure fats and oils are colorless and odorless
(color and odor is always a result of
contaminants) – i.e. butter (bacteria give flavor,
carotene gives color)
Fats and Oils

Formed from glycerol and fatty acids

O
CH2 OH HO C (CH2)14CH3
O
CH OH + HO C (CH2)14CH3
O
CH2 OH HO C (CH2)14CH3
glycerol palmitic acid (a fatty acid)
Examples of oils

• Olive oil – from Oleo europa (olive tree)

• Corn oil – from Zea mays
• Peanut oil – from Arachis hypogaea
• Cottonseed oil – from Gossypium
• Sesame oil – from Sesamum indicum
• Linseed oil – from Linum usitatissimum
• Sunflower seed oil – from Helianthus annuus
• Rapeseed oil – from Brassica rapa
• Coconut oil – from Cocos nucifera
Triglycerides (triacylglcerols)
Esters of glycerol and fatty acids

ester bonds
O
CH2 O C (CH2)14CH3 + H2O
O
CH O C (CH2)14CH3 + H 2O
O
CH2 O C (CH2)14CH3 + H 2O

25
A HYDROGENATION OF TRIACYLGLYCEROLS

•Solid commercial cooking fats are

manufactured by partial
•hydrogenation of vegetable oils. Completed
hydrogenation
•of the oil is very hard and brittle. One
commercial advantage
•of partial hydrogenation is to give the fat a
longer shelf-life.
BIOLOGICAL FUNCTION OF TRIACYLGLYCEROLS

•The primary function of

triacylglycerols in animal is as an
energy reserve.
•All of the saturated triacylglycerols
of the body, and some of the
unsaturated ones, can be
synthesized from carbohydrates and
proteins.
 WAXES
•simple esters of fatty acids (usually saturated with
long chain monohydric alcohols)
O

H3C (CH2)14 C O CH2 (CH2)28 -CH3

fatty acid
long chain alcohol

Beeswax – also includes some free alcohol and fatty acids

Spermaceti – contains cetyl palmitate (from whale oil) –useful for
Pharmaceuticals (creams/ointments; tableting and granulation)
Carnauba wax – from a palm tree from brazil – a hard wax used on
cars and boats
Waxes

H3C (CH2)14 CH2-OH cetyl alcohol

H3C (CH2)24 CH2-OH hexacosanol

H3C (CH2)28 CH2-OH triacontanol (myricyl alcohol)

Examples of long chain monohydric alcohols

found in waxes
 Phospholipids

• the major components of cell membranes

• phosphoglycerides
O

O O R
fatty acids (hydrophobic tail)
glycerol O R'
O-
O O X
P

O
phosphate

Phospholipids are generally composed of FAs, a nitrogenous base, phosphoric

acid and either glycerol, inositol or sphingosine
 O

O O R
fatty acids (hydrophobic tail)
glycerol O R'
O-
O O X
P

O
phosphate

X = H (phosphatidic acid) - precursor to other phospholipids

X = CH2-CH2-N+(CH3)3 phosphatidyl choline

X = CH2-CH(COO-)NH3+ phosphatidyl serine

X = CH2-CH2-NH3+ phosphatidyl ethanolamine

Sphingolipids

Sphingosine,
Is a fatty amine,
A feature that’s
Outlined in green!
Summary of Sphingolipids

• Ceramide (headgroup = H) is the parent of all

sphingolipids
• Sphingomyelins - polar headgroup (phospholipids)
• phosphocholine
• phosphoethanolamine
• Glycosphingolipids – sugars, no phosphate Neutral
• cerebrosides (1 sugar + ceramide)
• globosides (2 sugars or more + ceramide)
• Gangliosides – oligosaccharide headgroups
• with one or more sialic acid residues Charged
Sphingolipids

Based on sphingosine instead of glycerol OH

OH

sphingosine NH2

R long chain hydrocarbon

HO

NH2 attach fatty acid here

OH attach polar head group here

 Sphingomyelin (a ceramide)

HO R
O

NH R' usually palmitic acid

O-
O O
P N(CH3)+

O
phosphatidyl choline (also can be ethanolamine)

It is a ubiquitous component of animal cell membranes, where it is by far the most

abundant sphingolipid. It can comprise as much as 50% of the lipids in certain tissues,
though it is usually lower in concentration than phosphatidylcholine
Steroids

- Steroids are important “biological

regulators” that nearly always
show dramatic physiological effects when
they are administered
to living organisms.
- the most fundamental and famous
steroid is cholesterol
Other steroids that are
important in the body
• Androgens These are “male sex hormones” that regulate the
development of the male reproductive system and the secondary
sexual characteristics in males.
• Progesterone, estrone, and estradiol These are “female sex
hormones” that regulate the development of the female
reproductive system and are responsible for the maintenance of
secondary sexual characteristics in females.
• Aldosterone This steroid controls water and electrolyte balances.
• Cortisone This compound is involved in metabolism and in
controlling inflammation.
• Bile salts Facilitates the digestion of certain lipids and the
absorption of fat-soluble vitamins.
• Vitamin D An important steroid that controls calcium absorption
and deposition in the bone. Recent research also suggests that
vitamin D plays a fundamental role in the prevention of many
cancers. High consumption of vitamin D and sun exposure appear to
reduce cancer risk.
Terpenes: Fat-Soluble Vitamins

•Vitamin A – derivatives can absorb light (retinal

+ opsin = rhodopsin, a vision thing), and
control epithelial tissue development
•Vitamin K – a cofactor essential for activating
prothrombin, needed to promote blood
clotting
•Vitamin E – tocopherols, which as antioxidants
protect unsaturated fatty acids, and scavenge
damaging free radicals