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By : drg.

Prasetyo Adi, MS

OBJECTIVES :

Students can understand : 1. Classification of lipids 2. The importance and source of lipids 3. Chemical and physical properties of lipids

LIPIDS ???
Large molecules made up of elements Carbon, Hydrogen, Oxygen relatively insoluble in water, but soluble in nonpolar solvents such as ether, aceton, benzene, chloroform and carbon tetra chloride (CCl4) Non volatile, odorless, tasteless, but when its allowed to stand out in the open air for a long time rancid

LIPIDS FUNCTIONS

Energy storage
Constituent of membrane structure Hormone synthesis

Thermal insulator
Electrical insulator myelin sheath The solvent of fat-soluble vitamins

Basic structure
Fats are esters made up of an alcohol part and an acid part In fats the alcohol part is always glycerol The acid part of fats :

straight-chain carboxylic acids have an even number of carbon atoms

R C O R O

Acid part

Alcohol part

Basic structure :
O R1 O C O H2C O C R3
Triglyceride (triacylglycerol)

H2C CH

O O

Fatty acids

R2

R Lipids : Alkyl and Carboxyl groups


Alkyl is a hydrophobic group, which insoluble in water a non polar part

Carboxyl is a hydrophilic group, water soluble a polar part Hydrophobicity of R groups depend on : number of carbon atoms, branched or not, have double bonds or not

Fatty Acids
Long chain hydrocarbons with one carboxyl group

at the end of chain, which may be saturated or unsaturated Types of Fatty acids : Saturated FA : no double bond Unsaturated FA : one or more double bonds

Saturated FA based on the length of the straight chain of C, with the number of carbon atoms are odd or even, and there are branched or not.

A. The C straight chain with an even number of C atoms : Butyric ac, Kaproic ac, Kaprylic ac, Lauric ac, Myristic ac, Palmytic ac and Stearic ac. B. The C straight chain with an odd number of C atoms : Pentadecanoic ac, Heptadecanoic ac, Valeric ac, Heptanoic ac, Nonanoic ac C. The C branched chain of fatty acids :
COOH As.Pristanat

COOH

As.Phitanat

Systematic names of unsaturated fatty acids Based on the position and number of double bonds 1. D numbering system : The terminal carboxyl carbon is designated carbon 1, and the double bond is given the number of C atom on the carboxyl side of the double bond. Dp n : y p= position of double bond from terminal carboxyl group n= number of C atoms y= number of double bonds 2. w numbering system : The terminal methyl carbon is designated carbon 1, and the double bond is given the number of C atom on the carboxyl side of the double bond. wp,Cn : y p= position of double bond from terminal methyl group

3 : linolenic acid : CH3-CH2-(CH=CH-CH2)3-(CH2)6-COOH 6 :

1. Linoleic acid :
CH3-(CH2)4-(CH=CH-CH2)2-(CH2)6-COOH 2. Linolenic acid : -(CH=CH-CH2)3(CH2)3COOH 3. Arachidonic acid :

-(CH=CH-CH2)4(CH2)2COOH

Chemical properties of fatty acids


Carboxyl groups methylation Addition of halogen (unsaturated FA)


BrC C +IBr C i C Br C C I

Double bond transformation


BH H 2HC C C C C H H H H+ 2HC HC C C C H H H2

Oxydation
1. When fats and oils are allowed to stand out in the open oxidation by the air and turn some molecules into aldehydes rancid, with bad tastes and odors 2. Because of microorganism occurence, oxydation reaction do faster at room temperature

3.

Aldehyde group determines for rancidity

Hydrolysis
1. Hydrolysis of triglycerides short chain fatty acids which have bad odor. 2. To prevent oxydation and hydrolysis reaction of fats by giving an antioxidant or another compounds.

Hydrogenation
Double bonds can be reduced to single bonds by

treatment with hydrogen (H2) and a catalyst.

Iodine Number Test


A test for degree of unsaturated in fats and oils The test consists of adding a halogen to a sample The iodine number is defined as the number of grams of iodine that adds to 100 grams of samples I
I I

-- C = C -- + I2 -- C C I I I I

Lauric

Miristic

Palmi tic

Stea ric

Oleic

Linole ic

Linole nic

Othe r

Iodine number

Animal Fat Beef tallow Butter Lard Human Vegetable Oil Coconut Corn Cottonseed Linseed Olive Palm Peanut Safflower Soybean Sunflower

-2,5 --

6,3 11,1 1,3 2,7 18 1,4 1,4 --1,4 -6,8 0,1 --

27,4 29 28,3 24 10,5 10,2 23,4 6,3 6,9 40,1 8,3

14,1 9,2 11,9 8,4 2,3 3 1,1 2,5 2,3 5,5 3,1 2,4 2,2

49,6 26,7 47,5 46,9 7,5 49,6 22,9 19 84,4 42,7 56 18,6 28,9 25,1

2,5 3,6 6,0 10,2 -34.3 47,8 24,1 4,6 10,3 26,0 70,1 52,3 66,2

-------47,4 ---3,4 3,6 --

0,1 17,9 5,0 7,8 16,3 1,5 3,4 0,7 1,8 -6,6 1,1 2,7 --

50 36 59 68 10 123 106 179 81 54 93 145 130 126

45,5 ------0,2 --

9,5 5,6

Physical properties of fats


Fats that come from animals are generally solids

at room temperature Fats that come from plants or fish are usually liquids at room temperature oils The structural difference : - Solid fats contain mainly saturated FA - Liquid fats unsaturated FA

Triacyl Glycerol (TG)


Glycerol is an alcohol compound with three

hydroxyl groups can form esters with 1,2 or 3 of same or different fatty acids

, , and configuration at crystallic form gives properties of different melting point. The most stabil configuration is .

Classifications
1. Simple lipids : - Fats - Waxes 2. Complex lipids : - Phospholipids - Glycolipids (glycosphingolipids) - Other complex lipids :fosfolipids, aminolipids, lipoproteins 3. Precursors and derived lipids : - fatty acids - glycerol - steroids - keton bodies

1. Simple lipids:
= Esters of fatty acids with various alcohols.
- Fats: Esters of fatty acids with glycerol. Oils are fats in the liquid state. - Waxes: Esters of fatty acids with higher molecular monohydric alcohols. weight

2. Complex lipids :
= Esters of fatty acids containing groups in addition to an alcohol and a fatty acid. - Phospholipids: Lipids containing, in addition to fatty acids and an alcohol, a phosphoric acid residue. glycerophospholipids the alcohol is glycerol sphingophospholipids the alcohol is sphingosine. - Glycolipids (glycosphingolipids) : Lipids containing a fatty acid, sphingosine, and carbohydrate.

3. Derived lipids.
= Lipids derived from simple lipids and complex lipids These include : fatty acids, glycerol, steroids, other alcohols, fatty aldehydes, ketone bodies, hydrocarbons, lipid-soluble vitamins, and hormones.

COMPLEX LIPIDS : 1. Phospholipid contain : A. An Alcohol B. Fatty acids C. A Phosphate group 2 Types of Phospholipids : A. PHOSPHOGLYCERIDES
= Triesters of glycerol-3-phosphate in which Two of OH groups are esterified by fatty acids, the 3rd OH group is esterified by phosphate group, which is also connected to another alcohol.

Classification of phosphoglycerides : 1. 2. 3. 4. 5. Phosphatidylcholine (lechitin) Phosphatidyletanolamine (cephalin) Phosphatidylserine (cephalin) Phosphatidylinositol Cardiolipin
O H2C HC H2C O O O C C P O O O (CH2)16 CH3 (CH2)7 C H C H C C H2 H C H (CH2)4 CH3

O CH2C

+ N(CH3)3

LESITIN

B. Sphingolipids

Present in nearly all human tissues, which the greatest

concentration is in CNS white matter, the coating of nerve axon (myelin)


All sphingolipids are derived from sphingosine

H3C(H2C)12

H C

H C

H C

H C

CH2

Sphingosin

OH NH2 OH

O CH3 H2C
12

C H

C H

H C

H C

OH NH

C H2 O

P O -

+ OCH2CH2 N(NH3)3

Sphingomyelin

C R

2. GLYCOLIPIDS
= Complex lipids that contain carbohydrate
Among the glycolipids are cerebrosides, which are ceramide mono-or oligosaccharide.

STEROIDS

= compound containg this ring system :


12 11 1 2 10 9 13 17

1 cyclopentane (D)
16

C
14 8 7 6

D
15

A
3 5 4

STEROID

3 cyclohexane rings (A,B,C ) connected in the same way as in phenanthrene, and afused cyclopentane ring.

CHOLESTEROL.
H3C CH3 CH3 CH3 D

CH3

A HO

KHOLESTEROL

The most abundant steroid in human body Serve as membrane component (plasma membrane of erythrocyte and in the myelinated nerve cells) Serve as raw materials for other steroids (the sex and adrenocorticoid hormones)

Cholesterol
Exists both in the free form and esterified with fatty acids Free cholesterol gall stone Cholesterol in the body is in a dynamic state the serum cholesterol level controls the amount of cholesterol synthesized by liver Cholesterol is transported from the liver to the periferal tissues by lipoproteins (HDL, LDL, VLDL) High serum cholesterol level associates with such diseases as atherosclerosis

STEROID HORMONES

Synthesized from cholesterol :


The aliphatic side chain on the D ring is shortened by the removal of a six-carbon unit, and the secondary alcohol group on C-3 is oxidized to a ketone

PROGESTERONE
The starting compound

ADRENAL GLANDS

SEX HORMONES

ADRENOCORTICOD HORMONES
MINERALOCORTICOIDS GLUCOCORTICODS

KHOLESTEROL

H 3C CH3

CH3 CH3 D

CH2OH HO
CH3 C CH3

O OH

CH3

A HO

KORTISOL
A O B

CH3
CH3

CH2OH O
CH3

O OH

CH3

PROGESTERON

CH3

KORTISON

A O

A O

CH3

OH O CH2OH C O

CH3

HO
A O A B B

CH

TESTOSTERON

CH3

ALDOSTERON

CH3

OH

A HO

ESTRADIOL

Soaps
Soaps are produced from triglyceride hydrolysis in an alkaline medium Soaps clean because each soap molecule has a hydrophilic head (-COO-) and a hydrophobic tail ( a long chain alkaline-like portion). The hydrophilic head dissolevs in the water, the hydrophobic end dissolves in the dirt cause an emulsifying action

MEMBRANES
The function : 1. To separate cells from external environment 2. To provide selective transport for nutrients and waste products

EICOSANOIDS
Products of the metabolism of the 20-carbon-

polyunsaturated fatty acid arachidonic acid 3 groups : 1. Prostaglandins 2. Thromboxanes 3. Leukotrienes

Reading tasks : The Myelin sheath and Multiple


Sclerosis

Prostaglandins, thromboxanes, and Leukotriens


Atherosclerosis Gall stone

THANKS FOR YOUR ATTENTION