Download - Chapter 15 Lipids
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SWBAT: 1. Describe a lipid2. Describe the
classes of lipids
Chapter 15Lipids
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What are lipids?Group of molecules not
defined by structure but by common characteristicsThey are:
• non-polar• soluble in non-polar solvents like
methylene chloride, gasoline, ether• not soluble in polar solvent like water• fats, oils, fatty acids, waxes, steroids,
cholesterol, fat soluble vitamins
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Lipids and HealthBMI: Body Mass Index:
Body Fat vs ObesityBlood Lipids
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CAD:Coronary Artery Disease
Lipid deposits clogging arteries in the body and heartRisk Factors for CAD
• Hypertension, Diabetes, elevated cholesterol
• smoking• sedentary lifestyle• stress• obesity• male sex• family history• older age
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Types of LipidsSaponifiable Lipids:• Prostaglandins• Waxes• Tricylglycerols• Glycerophospholipids
Non-Saponifiable Lipids:• Cholesterol• Steroid hormones
Can be Hydrolyzed
Can NOT be Hydrolyzed
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HomeworkChapter 15.1Pg 497#15.2 – 15.4 (even)
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SWBAT: 1. Write structures of
fatty acids2. ID saturated and
unsaturated fatty acids
Chapter 15Fatty Acids
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Fatty AcidsContains a long carbon
chain attached to a carboxylic acid on C1
Typically contain and even number of carbon atoms – between 10 and 20
Dodecanoic Acid
Lauric Acid
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Fatty AcidsThey are:• Aliphatic molecules –
they are both hydrophobic and hydrophilic
• But…overall they are hydrophobic
Hydrophilic
Hydrophobic Cell
Membrane
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Fatty Acids to know…
Laura, My Palm Stinks!
Lauric Acid (C12)
Myristic Acid (C14)
Palmitic Acid (C16)
Stearic Acid (C18)
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Types of Fatty AcidsSaturated Fatty Acids:• Only single bonds between
the carbon atoms
Monounsaturated Fatty Acids:• Have one double bond in
the carbon chain
Polyunsaturated Fatty Acids:• Have two or more double
bonds
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Unsaturated Fatty Acids
trans double bonds
cis double bonds
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Shapes of Unsaturated Fatty Acids
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Fatty Acids:Physical Properties
Saturated and trans Fatty Acids:
• High melting points (solids) • Perfect alignment – high
Van de Waals intermolecular attractions• Trans fatty acids do
not naturally exist – they are a man made product and are the most stable fatty acids
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Fatty Acids:Physical Properties
Unsaturated cis Fatty Acids:
• Lower melting point (liquid at room temp)
• Do not have perfect alignment due to kinks in chain – low Van de Waals
• Less stable – double bonds can break
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Both are:C18H36O2
SaturatedMP of 69° Unsaturat
edMP of 13°
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ProstaglandinsThey are:• Small polyunsaturated
Fatty Acids that act like hormones mediating a range of symptoms from inflammation to blood pressure
• Synthesized from Arachidonic Acid (AA)
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Prostaglandins• Most have a hydroxyl
group on C11 and C15 and a trans double bond at C13• PGE - those with a ketone on C9
• PGF - those with a hydroxyl group on C9
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Inflammation is a…• Natural response to
infection and injury• Disease like rheumatoid
arthritis (inflammation of the joints)
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Why do we care?
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Non Steroidal Anti-Inflammatory Drugs
(NSAIDs)Drug class that includes:• Aspirin• Ibuprofen• Naproxen (Alveve)• Ketoprofen (actron)• Nabumetone (Relafen)Long term use can result
in liver, kidney and gastrointestinal damage
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NSAID effect and side effect
Stomach side effect
Video Links
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HomeworkChapter 15.2Pg 503#15.6 – 15.18 (even)
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SWBAT: 1. Write structural
formula of wax, fat or oil
2. ID the reaction of a fatty acid and an alcohol or glycerol
Chapter 15Waxes, Fats and Oils
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Waxes• Found in many plants and
animals (leaves, stems, skin, fur and feathers)
• Is an ester of a saturated Fatty Acid and a long-chain alcohol (14-30 carbon atoms)
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Fats and Oils: Triacylglycerols
• The body stores Fatty Acids as fats and oils
• Also called tryglycerides
• Produced by esterification of glycerol and Fatty Acid groups
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Fats and Oils: Triacylglycerols
Most fats and oils are mixed triacylglycerolds with two or three different Fatty Acids
from stearic acidfrom palmitic
acidfrom myristic
acidcan be saturated or
unsaturated
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Writing Structures for Triacylglycerol
• Each Fatty Acid is attached by an ester bond to one of the hydroxyl groups in glycerol
Alcohol Part:• In
triglycerides always glycerol
Carboxylic Acid Part:• Three Fatty Acids
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Fats and Oils:Physical Properties
• A fat is a solid at room temperature (fats in meat, butter, cheese)
• There are exceptions
• Typically from an animal source
• Oil is usually liquid at room temperature (oils – olive, peanut, sunflower)
• Typically from a plant source
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Fats and Oils:Physical Properties
• Saturated Fatty Acids have higher melting points because they pack together tightly
• Animal fats usually contain more saturated Fatty Acids than vegetable oils
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Melting Points
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HomeworkChapter 15.3Pg 507-508#15.20 – 15.28 (even)
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SWBAT: Draw the structure of
the product from a reaction of triacylglycerol with hydrogen, or an acid or base
Chapter 15Chem Props of Triacylglycerols
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Hydrogenation• Hydrogenation of
unsaturated fats converts carbon-carbon double bonds to single bonds
• Hydrogen gas is heated through oil with a nickel catalyst• Partial hydrogenation changes oil to a soft, semisolid fat (crisco)
H2
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Why?• Chemical process
patented in the 1940’s • used to convert oil
surpluses from soybean farming
• into spreadable fats (margarines) to alleviate butter shortage
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Problem…Incomplete hydrogenation
leads to the formation of trans-double bonds→ Trans Fats
Trans Fats raise LDL (bad cholesterol ) levels in the body
Consumption of Trans Fats is correlated with a rise in CAD during 1960-2000
FDA prohibits use of Trans Fats & requires labeling
trans fats in our foodVideo Link
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Hydrolysis• Breaking the ester bond –
yielding fatty acid & glycerol• First step in the digesting of
triglycerides in the body• Carried out by the enzyme
lipase • Glycerol is soluble in water
• Fatty Acids are not
H+
lipase
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Saponification (sapon = soap)• Reacting triglycerides with
a strong base• Yields glycerol and Fatty
Acid Salts (soap)
Glycerol tritearate + 3 NaOH glycerol + 3 sodium stearate
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What is Soap• Soaps are aliphaic
molecules that have a polar part (facing water molecules) and a non-polar part (facing greasy dirt)
• Ancient soap making – Animal fats are heated with a strong base (lye from burnt limestone)
• Fatty acid salts – Sodium paltmitate: Na+ -OOC-(CH2)14-CH3
• Soap Making Video
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Food Labels
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Food Labels
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Olestra• Fatty Acids from
cottonseed or soybean oils
• Composed of 6 to 8 long-chain Fatty Acids attached to sucrose rather than glycerol• We can’t digest it so “Fake Fat” goes straight through our system
• GI problems occurred
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HomeworkChapter 15.4Pg 512-513#15.30 – 15.36 (even)
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SWBAT: 1. Describe the
characteristics of glycerophospholipids
Chapter 1515.5 Glycerophospholipids
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What are Glycerophospholipids?• Similar to triglycerides
except one hydroxyl group is replaced by the ester of phosphoric acid and an amino alcohol• Bonded through a phosphodiester bond
GlycerophospholipidsTriglycerides
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Amino Alcohols• Three amino
alcohols found in glycerophospholipids are:
choline ethanolamine serine
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Lecithins• Lecithins contain choline• Fatty Acids can be same,
different, saturated, unsaturated or mixture
• Abundant in:• brain tissue• nerve tissue• egg yolks • wheat germ
• yeast
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Cephalins• Cephalins contain
ethanolamine and sometimes serine
• Abundant in:• brain tissue• nerve tissue• egg yolks • wheat germ
• yeast
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Polar?
• Contain both polar and nonpolar regions
• Ionized alcohol and phosphate portion is called “the head”– Can hydrogen bond with water
• Two Fatty Acids represent “the tail”
• Hydrophobic Tails
• Hydrophilic Head Group
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Polar and Nonpolar Regions
• Most abundant in lipids in cell membrane
Nonpolar Tails
Polar Head
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HomeworkChapter 15.5Pg 515#15.38 – 15.42
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SWBAT: Describe the
structure of steroids
Chapter 15Cholesterol & Steroid
Hoemones
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General Structure
Steroidnucleus: • Three cyclohexane rings
A,B,C• One cyclopentane ring D
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Types of Steroids• Cholesterol• Lipoproteins• Steroid Hormones• Anabolic Steroids
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• Why does it have the ending –ol?
Cholesterol
Most abundant steroid in the body
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Facts about Cholesterol
• its part of every cell membrane
• insulates nerve and brain tissue
• forms bile for digestion• forms Vitamin D in skin• starting material for steroid hormones:
sex hormones, cortisone• leads to heart attacks
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Lipid Metabolism • Cholesterol is so
important that the body does not rely on what you eat….
• It manufactures 80% of the cholesterol needed• Serum Cholesterol Levels in your body can be measured via blood tests: Lipid Panels
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Lipid PanelsWhat health care
professional look for…• Total Cholesterol• HDL: High density Cholesterol –
“good”• LDL: Low density Cholesterol –
“bad”
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Why?Lowering Cholesterol Levels
is a business….Food industry:
fat free/cholesterol free itemslean meatslow fat dairyhunt against saturated fats
Pharmaceutical industry: statin drugsHMG-CoA reductase inhibitors
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LIPITORThe most widely used drug
in the world…• Pharmaceutical drug
lowering cholesterol levels
• Reaps 26 billion in sales per year worldwide
• Side effects range from diabetes, to cancer
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Cholesterol LevelsCholesterol levels show
individual variations due to:
• Genetics• Age • General health: cholesterol is an anti-
inflammatory, anti-stress substance, it can rise due to reasons ranging from stress, lack of sleep, drugs and chronic diseases (diabetes)
• Diet: Plant based diets are correlated with lower cholesterol levels
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Cholesterol in Food• Egg 250 mg• Crab/Shrimp 150
mg• Beef 85 mg• White chicken 75 mg• Fish 40 mg
• All animal based food contain cholesterol
• All plant based foods contain no cholesterol
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Cholesterol and CAD
• Artheriosclerosis is the main cause of CAD
• It is caused by plaque that clog arteries
• Plaque are cholesterol depositsQ: What makes cholesterol form plaque?A: Inflammation
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Transporting Fats in Blood
• Lipids are insoluble in the blood (=water)
• Lipids are transported from spherical vesicles called Lipoproteins
• Skin: Phospholipids, Proteins
• Inside: Cholesterol, Triglycerides
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Steroid HormonesSex Hormones• Estrogen: development
of female sex characteristics• Testosterone: development of male sex characteristics including muscle anabolism
• Progesterone: prepares uterus for fertilized egg
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Steroid HormonesCorticosteroids• Steroid Hormones
produced by the adrenal glands• Natural – Cortisone
• Drug – Prednisone• Helps with:
• stress response• immune response• regulation of
inflammation
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Anabolic Steroids• Synthetic
Testosterone derivatives
• Promote muscle growth, reduce body fat
• Short term side effects: broken bones, ruptured tendons, kidney pain
• Long term use lead to kidney, heart, liver damage
• Legal steroid Tren
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HomeworkChapter 15.6Pg 522#15.44 – 15.54 (even)
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SWBAT: 1. Describe the
composition and function of the lipid bilayer in cell membranes
Chapter 1515.7 Cell Membranes
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Cell Membrane• Composed of phospholipid
bilayer• Polar head & nonpolar tails• Semipermeable – items can
enter and leave
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Lipid Bilayer• Double row arrangement
of phospholipids
• Hydrophilic polar heads align on outer edges of membrane
• Hydrophobic nonpolar tails move to center
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Fluid Mosaic Model• Lipid bilayer contains
unsaturated Fatty Acid• Cis double bonds
causes a non-rigid structure
• In liquid like bilayer:• Proteins• Carbohydrat
es• Cholesterol
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HomeworkChapter 15.7Pg 524 – 525 #15.56 – 15.62