Documenti di Didattica
Documenti di Professioni
Documenti di Cultura
Lipids
Chemistry 106
M. Todd Tippetts, Ph.D.
Lipids
Biological compound soluble in non-polar solvent
Chemically heterogeneous: Simple or Complex
Simple Lipid: alcohol + one or more fatty acids
Complex lipid: alcohol + fatty acid + something
else
Classification of Lipids
Fatty Acids
Linear Molecules 10-20 carbons in length
Even number of carbons
No other functional groups but carboxyl
Sometimes alkene groups C=C
Saturated vs. unsaturated
Water Solubility
Hydrophobic part of molecule dominates: very
insoluble in water
Forms micelles in water
* *
*
*
*
*
*
saturated Fatty Acids to Know
lauric 12 0
myristic 14 0
palmitic 16 0
stearic 18 0
Unsaturated Fatty Acids to Know
oleic 18 1
linoleic 18 2
linolenic 18 3
arachadonic 20 4
Melting Points
Increases with size (lesser effect)
Decreases with unsaturation (greater effect)
Cis vs Trans Fatty Acids
Cis fatty acids occur naturally
Trans fatty acids occur during hydrogenation
reactions
H H
C C
CH3CH2CH2CH2CH2CH2 CH2CH2CH2CH2COOH
H
CH2CH2CH2CH2COOH
C C
CH3CH2CH2CH2CH2CH2 H
Alternate View of Fatty Acids
COOH
COOH
Triglycerides: Fats and Oils
Glycerol + 3
Fatty Acids
Connected
by ester
bonds
Triglyceride
CH2 OH
O
CH OH + 3 HO C
CH2 OH
CH2 O C
O
CH O C
O
CH2 O C
Draw a triglyceride made from stearic, palmitic
and myristic acid
O
CH2 O C
O
CH O C
O
CH2 O C
CH O C (CH2)12 CH3
O
H H H H
+ I2 R2 R1
R2 R1
I I
CH2 O C (CH2)16-CH3
O
CH O C (CH2)16-CH3
+3 H2O
O
CH2 O C (CH2)16-CH3
H2C OH
O
HC OH +3 CH3 (CH2)16 C OH
H2C OH
Chemical Properties of Triglycerides
3. Saponification with NaOH
O
CH2 O C (CH2)16-CH3
O
CH O C (CH2)16-CH3
+3 NaOH
O
CH2 O C (CH2)16-CH3
H2C OH
O
- +
HC OH +3 CH3 (CH2)16 C O Na
H2C OH
Saponification Reaction produces Soaps
Hydrophilic and hydrophobic regions
Hydrophobic dissolved in oils
Hydrophilic stays on the surface
Insoluble salts form with hard water
O
- +
C O Na
Sodium stearate
O
- +
O S O Na
H H H H
+ H 2 Pt R2 R1
R2 R1
H H
Myristyl palmitate
Wax Block Diagram
Phosphoglycerides
Glycerol, 2 fatty acids, phosphate + another
alcohol
Fatty Acid
Glycerol
Fatty Acid
Phosphate 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
Phosphatidyl Choline (lecithin)
O
CH2 O C (CH2)16-CH3
O
CH O C (CH2)16-CH3
O CH3
O- CH3
CH2 O C (CH2)16-CH3
O
CH O C (CH2)16-CH3
O
O- COO-
Sphinglipids: Sphingosine + fatty acid
+ something else
OH
NH2
CH OH
Ceramide: sphingosine + fatty acid
CH3 (CH2)12 CH CH CH OH O
CH NH C (CH2)14 CH3
CH OH
CH OH
Sphingomyelin: sphingosine, fatty acid,
phosphate and choline
Sphingomyelins
found in myelin
sheath around
neurons
Sphingomyelin
Fatty acid
CH3 (CH2)12 CH CH CH OH O
CH NH C (CH2)14 CH3
O CH3
CH O P O CH2CH2 N+ CH3
O- CH3
phosphate choline
Glycolipid: Lipid + Carbohydrate
Cerebroside: Sphingosine +
fatty acid + carbohydrate
CH3 (CH2)12 CH CH CH OH O
CH NH C (CH2)14 CH3
H2C OH
O HO
H2C O
OH
OH
Lipid Storage Diseases
Biological Membranes
Separates cell interior from exterior,
or cellular organelles from cytoplasml
About 60% lipid and 40% protein
Glc = glucose
Gal = galactose
GalNAc =
N-acetylgalactosamine
Fuc = fucose
Steroids
Non-saponifiable lipids derived from
cholesterol
CH (CH2)3 CH CH3
CH3
HO
HO OH
CH3 C O CH3 C O
HO OH O OH
CH3 CH3
O O
cortisol cortisone
O CH2OH
CH C O
HO OH
CH3 aldosterone
O
Male Sex Hormones
Testosterone
Produced by testes
Male genitals and secondary sex characteristics
Muscle growth
Anabolic Steroids (fake testosterone)
Intended to prevent muscle atrophy
Used by athletes, widely banned
Bad side effects
Female Sex Hormones
Estrogen(estradiol, estrone) and
progersterone
Produced by ovaries
Reproductive cycle and secondary female
characteristics
Mimicked by birth control pills
Prostaglandins
Hormone like action
Regulates fever, contractions, inflammation
Induces labor, and asthma
Made from arachadonic acid
Synthesis inhibited by aspirin and
cyclooxygenase inhibitors
HO
COOH
CH3
HO
HO
Classification of Lipids