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Lipids
Lipids
• Lipids are organic molecules essential for
life that are composed mostly of C, H, O
• 4 types of lipids
– fats (triglycerides)
– phospholipids
– steroids
– waxes
- Family of bimolecules.
O O
Heat
RCOR' + H2O H+ or enzyme RC- OH + H-OR'
An ester A carboxylic acid An alcohol
Fatty acids
Saturated fatty acids have no double bonds in their long hydrocarbon chains.
COOH
COOH
COOH
COOH
COOH
Oxidation of Organic Compounds, eg.
fatty acids
O2
-C-C-C-COOH -C-COH-C-COOH
saturated difficult
O2
-C=C-C-COOH -COH-COH-C-COOH
unsaturated easy
COOH
COOH
COOH
COOH
COOH
Oleic acid
• More than one double bond fatty acids are called essential fatty
acids and they must be provided by the diet.
• Monounsaturated
• Sources: olive, peanut, canola, rape oil, almonds, avocado
• Polyunsaturated
• Sources: sunflower, soybean, corn, and safflower oil, fish oil,
walnuts, sesame seeds, pumpkin seeds, tofu, lard
• Unsaturated fatty acids are sensitive to heat and light damage –
store them in the dark bottles and use for cold or short hot
preparations
Essential Fatty acids
Ester bond
Long-chain alcohol Fatty acid
Acid
Waxes
Acid
Waxes
- In plants, they help prevent loss of water and damage from pests.
Jojoba
Heat
Triacylglycerols (Triglycerides)
Triacylglycerols are:
• Triesters of glycerol.
• Glycerol + 3
Fatty Acids
• Connected by
ester bonds
Esterification
O
CH2 OH HO C (CH2)14CH3
O
CH OH HO C (CH2)14CH3
O
CH2 OH HO C (CH2)14CH3 O
CH2 O C (CH2)14CH3
O
CH O C (CH2)14CH3 + 3H2O
Acid
O
CH2 O C (CH2)14CH3
Triacylglycerols (Triglycerides)
CH2 OH
CH OH Glycerol
CH2 OH
O
G Fatty acid
CH2 O C (CH2)5CH CH(CH2)7CH3
L
O Y
C
CH O C (CH2)5CH CH(CH2)7CH3 Fatty acid
E
O R
CH2 O (CH2)5CH CH(CH2)7CH3 O
C L Fatty acid
- Fats are used to build cell membranes, insulate the body, and
store energy for later use.
- The result is high blood pressure, heart attack, and even stroke.
- Unlike other vegetable oils, oils from palm and coconut trees are
very high in saturated fats.
Fat & Health
- Unsaturated triacylglycerols (omega-3 fatty acids from fish) lower the risk
of heart disease by decreasing the level of cholesterol in the blood.
H H
- Melting point is increased.
O
CH2 O C (CH2)5CH CH(CH2)7CH3
O Ni
_
CH O C (CH2)5CH _ CH(CH2)7CH3 + 3H2
O
CH2 O C (CH2)5CH CH(CH2)7CH3
O
(triolein) O
CH O C (CH2)14CH3
O
CH2 O C (CH2)14CH3
glyceryl tristearate
(tristearin)
Reactions (“Synthetic”)
unsaturated saturated
•Used to quantitate
unsaturation in fats
•Product is colorless, I2 is
colored
•Iodine number = grams I2
reacting with 100 g fat
Hydrolysis
O
CH2 O C (CH2)14CH3
O
CH O C (CH2)14CH3 + 3H2O
O
CH2 O C (CH2)14CH3
H
CH2 OH
O
+-
H +Na3H
CH OH O C (CH2)14CH3
H+ or Lipase
H
CH2 OH
Review of Chemical Reactions
Metabolism of tricaylglycerols
- With KOH or the oils that are polyunsaturated gives softer soaps
(liquid soaps).
- Soaps are typically made from lard (from hogs), tallow (from cows
or sheep), coconut oil, or palm oil.
- All soaps work in the same way, but have different properties
depending on the lipid source, length of C chain, and degree of
unsaturation.
3- Saponification (Basic Hydrolysis)
O
CH2 O C (CH2)14CH3
O
CH O C (CH2)14CH3 + 3NaOH
O
CH2 O C (CH2)14CH3
H
CH2 OH
O
Heat
H
CH OH + Na++--O C
3Na (CH2)14CH3
“soap”
Salt of fatty acid
CH2 OH
H
Soaps
O
- +
3 RCO N a
Sodium soaps
n)
Soaps
When soap is mixed with dirt (grease, oil, and …), soap
micelles “dissolve” these nonpolar, water-insoluble molecules.
Soap makes Grease ‘water-soluble’
Soaps in Hard water
• Curd formation due to insoluble Fe, Ca and
Mg carboxylates
• Water softeners: exchange Na for Fe, Ca
and Mg ions, increasing solubility of the
carboxylates
• Detergents function better in hard water
because sulfonates are soluble
phospholipids
1. Phosphoacylglycerols:
Fatty acid
Fatty acid
Amino alcohol
O
CH2 O C (CH2)16-CH3
O Phosphatidic acid
CH O C (CH2)16-CH3
O
CH2 O P OH
OH
Alcohols used in phosphoglycerides
CH3
HO CH2 CH2 N+ CH3
CH3
choline
NH2 O
serine ethanolamine
phospholipids
1. Phosphoacylglycerols:
Ethanolamine Choline
Phosphatidyl serine: a cephalin found in cell
memranes
CH2 O C (CH2)16-CH3
O
CH O C (CH2)16-CH3
O
O- COO-
phospholipids
1. They do not contain a glycerol backbone, they have a sphingosine backbone instead.
sphingosine
2. They do not contain an ester; their single fatty acid is bonded to the backbone
by an amide bond.
Sphingomyelin: sphingosine, fatty acid,
phosphate and choline
Sphingomyelins
found in myelin
sheath around
neurons
Ceramide: sphingosine + fatty acid
CH3 (CH2)12 CH CH CH OH O
CH NH C (CH2)14 CH3
CH OH
CH OH
phospholipids
2. Sphingomyelins:
The myelin sheath, the coating that surrounds nerve cells, is rich in sphingomyelins.
phosphoacylglycerols
Nonpolar
O R Polar
Carbohydrate
Phospholipid
bilayer
Nonpolar
Hydrophobic
Polar
Hydrophilic
Semipermeable: selected nutrients can enter and waste products can leave.
Steroids have:
(steroid nucleus)
• No fatty acids.
Cholesterol
Cholesterol:
CH3 CH3
CH3
CH3
CH3
HO
Cholesterol
Cholesterol:
At artery clogged by
• Is needed for cell membranes, brain and cholesterol plaque
nerve tissue, steroid hormones, and
Vitamin D.
Water-soluble form of
lipids
(soluble in blood)
Spherical particles
Transporting lipids through the bloodstream to tissues where they are stored,
Used for energy, or to make hormones.
Lipoproteins
VLDL
LDL
Steroid Hormones
- They have the same effect as testosterone, but are more stable, so
they are not metabolized as quickly.
aldosterone
cortisone
cortisol
Vitamins
They must be obtained from the diet (our cells cannot synthesize them).
They are found in fruits, vegetables, fish, liver, and dairy products.
Vitamin A
It is found in liver, fish, and dairy products, and is made from β-carotene
(the orange pigment in carrots).
Vitamin A deficiency causes night blindness and dry eyes and skin.
Vitamins
Vitamin D
It can be obtained in the diet from many foods, especially milk, and
helps regulate Ca and P metabolism.
Vitamin E
Vitamin K