Chemistry Summer Assignment : Lipids

By: Lidia Kim, Kate Cutting, Nadege Assassi, Nidah Khakoo, Athina Krimitzi and Niki Romanzi

Objective B.4.1
Compare the Composition of the Three Types of Lipids Found in the Human Body

By: Lidia Kim

Background
Glycerol Has 3 OH groups (tri-ol) Fatty Acid 16-22 Carbons A type of carboxyl acid R-COOH Phosphate Group

Triglycerides
Composed of: 1 glycerol + 3 fatty acids
If the 3 fatty acids are the same its a simple triglyceride, if different then mixed triglyceride.

Formed by the condensation reaction between propane-1,2,3-triol and long chain carboxylic acids.(ie. Glycerol and fatty acids :P) Oils (polyunsaturated): two or more double bonds Fats (saturated): No double bonds, saturated (with H) carboxyl groups

(saturated)

(unsaturated)

Phospholipids
A back bone (glycerol) 2 fatty acids (hydrophobic) Phosphate group (hydrophilic)
Function: plasma membrane, source of cholinefor making acetylcholine (nerve chemical transmitter.)
amphipathic

O2 in the phosphate make the region around them negative (phosphate part of the molecule is polar). Polar molecules are hydrophilic The phosphate is derived from an alcohol such as choline or ethanolamine.*

The fatty acid tails are nonpolar and hydrophobic

*Ex.lecithin contains choline as the side chain.

Steroids
Belong to groups of steroids called sterols Composed of: 3cyclohexane (6c) rings with one cyclopentane (5C) rings (No fatty acids) Skeleton can change from addition of side chains Function: establish extent of membrane permeability in cell membranes (hydrocarbon embedded in membrane with fatty acids, and hydroxyl group on the outside), manufactures hormones

Objective B.4.2
Outline the difference between HDL and LDL cholesterol and outline its importance.

By: Kate Cutting

Lipoproteins
Lipoproteins are composed of lipids (fats) and proteins Cholesterol is insoluble in water and substances such as blood This means Cholesterol molecules cannot move around themselves in the blood
Lipoproteins transport lipids and cholesterol Protein is soluble in water and blood so they form an outer layer around the cholesterol with the lipid part towards the cholesterol

HDL Cholesterol
HDL (High Density Lipoprotein) Cholesterol is GOOD Cholesterol Has less lipid so it can transport more cholesterol away from the arteries and to the liver where it is broken down Is more dense than LDL because it contains higher proportion of protein Can eliminate LDL Cholesterol

LDL Cholesterol
Carry cholesterol to build and repair damaged tissue so a little bit is not bad LDL (Low Density Lipoprotein) Cholesterol is BAD Cholesterol Transports cholesterol to arteries starting the formation of plaque and blocking blood pathway Less dense than than HDL due to a lower proportion of proteins HDL is 45-50% protein, LDL is 25% protein

 Increased levels of LDL cholesterol is associated with atherosclerosis Leads to heart attack, stroke, etc.

Objective B.4.3
Describe the difference in structure between saturated and unsaturated fatty acids.

By: Nadege Assassi

Unsaturated Fats
Have C=C bonds Monounsaturated vs. Polyunsaturated Mono: 1 C=C bond Poly: multiple C=C bonds C=C bonds create bends in the molecules This minimizes flexibility of the fatty acids, preventing the molecules from aligning closely Create less dense molecules, making them more reactive and able to break down more easily Relatively low density means less intermolecular forces and lower melting points Liquid at room temperature Less single bondsmolecules packing less denselyless collisionsless van der waals forceslower melting point

Saturated Fats
Have no C=C bonds
All single C-C or C-H bonds

Not very reactive Greater intermolecular bonds

More van der Waals forces can occur when saturated chains lie alongside one another, because contact surface area is maximized

High melting points due to greater intermolecular bonds Solid at room temperature

Fats in General
As length of fat increases, there are more van der waals forces acting on the molecule, so melting point increases Because saturated fats can stack neatly on top of each other, a saturated fat has a higher melting point than and unsaturated fat of the same length

H2 and a Nickel(Ni) or Platinum(Pt) catalyst can be used to hydrogenate unsaturated fats, making them solid at room temperature

Objective B.4.4
Compare the structures of the two essential fatty acids, linoleic (omega-6 fatty acid) and linolenic (omega-3 fatty acid) and state their importance. By: Nadege Assassi

Essential Fatty Acids

Ingredients that the body needs to grow and develop healthily, but cannot produce on its own Must enter the body through diet Roles of EFAs Hormone synthesis Intercellular communication Blood Clotting Produce prostoglandins (maintain homeostasis) Insulin Sensitivity Lack of EFAs results in: Heart Attack Cancers Insulin Resistance/Diabetes Asthma Schizophrenia/Alzheimers Obesity Arthritis

Linoleic Acid (Omega-6 Fatty Acid)

C18H32O2 Omega: how many C from end lies the C=C bond Polyunsaturated carboxylic acid that cannot be produced by the body Has multiple C=C bond 18-Carbon chain Colorless and liquid at room temperature Found in oils 2 cis double bonds C-6 (hence, Omega-6) and C-9 Found in seeds and vegetable oils Essential to skin cell repair and reduces body fat
Lack of Omega-6 Results:

Dry hair
Hair loss Poor wound healing

Linolenic Acid (Omega-3 Fatty Acid)

C18H30O2 Polyunsaturated carboxylic acid that cannot be produced by the body Has multiple C=C bonds 18-Carbon chain Also found in oils 3 cis double bonds C-3 (hence omega-3), C-6, and C-9 Found in thylakoid membranes of green leaves Shown to be essential in thwarting cardiovascular problems and lowering blood cholesterol Prevents clotting and decreases inflammation Lack of Linolenic Acid Results in: Vision and Nerve Problems Depression Poor Circulation Arthritis

Linoleic Acid

Linolenic Acid

Objective B.4.5
Define the term iodine number and calculate the number of C=C double bonds in an unsaturated fat-oil using addition reactions.

Iodine Number
Iodine number: mass of I2 (in g) for particular reaction I2 number used to identify number of unsaturated C=C double bonds Higher I2 number means more unsaturated bonds I2 Number Calculation:
I2 solution used in reaction is yellow brownish Precise mass of solution added to 100g lipid solution Solution becomes colorless Mass of iodine required is iodine number

Number of moles of I2 reacting with one mole of fat/oil indicates number of double bonds present in fat/oil

Iodine Number Worked Example

Linoleic acid has the formula C18H32O2. Determine the iodine number of linoleic acid. Linoleic acid can also be written C17H31COOH. A saturated fat formula is CnH2n+1COOH. The difference in C:H in linoleci is 2n-3: 4 less H atoms. 2Hs are lost for each double bond so 2 double bonds. So 2 mol of I2 will react with 1 mol of the fatty acid (1 I2 reacts with 1 double bond). M of linoleic acid = 280 gmol-1 and M of I2 =254 gmol-1 So 280 g of lipid reacts with 508 g I2 So 100 g reacts with 508 x 100 / 280 = 181 g Iodine number = 181

Iodine Number now you try

1. Determine the mass of I2 that can add to 100 g linolenic acid.

1. A sample of fat containing 0.02 moles fatty acid was found to react with 10.16 g of iodine. Determine the number of carbon-carbon double bonds present in the fatty acid.

Objective B.4.6
Describe the condensation of glycerol and three fatty acids molecules to make a triglyceride.

Fats
Two classes of molecules. Saturated fatty acids. No double bonds between carbons in molecule. Hydrogen molecules saturate carbons in place of double bonds. Unsaturated fatty acids. One to three double bonds between carbons per molecule. Lower melting point.

Triglycerides
Three fatty acids combine with a glycerol backbone to create a triglyceride. One bond forms at a time by condensation between COO- on the fatty acids and the OH on the glycerol. Glycerols IUPAC name is propane-1,2,3-triol.

Ester Linkage
Ester linkage bond between a hydroxyl and carboxylic acid. A condensation reaction occurs to combine the two molecules with the loss of a water molecule. This type of condensation is called esterification. Result is a triglyceride.

Hydration
The reverse reaction will require water and will produce the fatty acid and glycerol monomers.

Objective B.4.7
Describe the enzyme-catalysed hydrolysis of triglycerides during digestion.

By: Nidah Khakoo

Quick Refresher: What are triglycerides?

Fats and oils are known as triglycerides Formed from glycerol and fatty acids Difference between fats and oils? Fats contain saturated fatty acid groups NO C=C double bonds Oils contain at least one C=C bond The C=C bonds give that kinked shape.

Hydrolysis of Fats

1. Triglyceride is hydrolyzed by lipases. 2. Glycerol and fatty acids are broken down to produce CARBON DIOXIDE, WATER, and ENERGY. 3. Fats are in a less oxidized form then carbohydrates so weight for weight produce MORE energy

Hydrolysis of Fats
Naturally occurring fats and oils are also known as esters. In an esterification reaction, there is an interaction of a carboxylic acid and an alcohol, aided by a catalyst. The REVERSE of an esterification reaction is known as hydrolysis. This is the addition of water to the ester link, breaking apart the ester into monoglycerides and diglycerides. Requires the presence of a catalyst.

Objective B.4.8
Explain the higher energy value of fats as compared to carbohydrates
By: Athina Krimitzi

 Gram for gram, fats provide more energy than carbohydrates. Fats require more oxidation to become CO2 and H2O than do carbohydrates.
carbohydrates already have one oxygen for every carbon atom each carbon atom in a carbohydrate needs only one more oxygen every carbon atom in a fat molecule needs two oxygens

 The oxidation of fats takes longer, but it also gives off more energy. When you weigh a carbohydrate, more oxygen is included in that weight. When you weigh a fat, you get more carbon atoms per gram and therefore, gram for gram, the fats will give even more energy (over twice as much) than will the carbohydrates.

Examples
Carbohydrates C6H12O6 + 6O26CO2 + 6H2O CH2O + O2CO2 + H2O Fats 83O2 + C58H112O658CO2 + 56H2O

Objective B.4.9
Describe the important roles of lipids in the body and the negative effects that they can have on health.

By: Nicole Romanzi

Lipids
Important roles are:
Energy storage as triacylglycerols Insulation and protection of organs Steriod hormones Structural component of cell membranes Omega-3-poly unsaturated fatty acids reduce the risk of heart disease Poly-unsaturated fats may lower LDL cholesterol

Negative effects:
Increased risk of heart disease from increased levels of LDL cholesterol and trans fatty acids Obesity

Energy Storage and Insulation

Lipids break down slower than carbohydrates So they cant be used as fast energy like glycogen can. Lipids are more efficient energy stores, and a good thermal insulator Also protects organs from being harmed when a person jumps or falls or similar exercises

Benefits of Fats
Omega-3 poly-unsaturated fatty acids Proven to reduce the risk of heart disease Poly-unsaturated fats May lower the levels of LDL cholesterol

Hormones and Membranes

Some lipids are steroid hormones i.e.: almost all steroids, most notably estrogen, testosterone, and adrenaline All are able to pass through the cell membrane and are fatsoluble Some are also precursors to some vitamins, Like Vitamin D Membranes Lipids are a large part of the semi-permeable cell membranes lipid bilayer. Most of the structure of the bilayer is made of lipids.

NEGATIVE EFFECTS
Increased risk of heart disease from elevated levels of LDL cholesterol and trans fatty acids The major source of low-density lipoproteins (LDLs) is saturated fats i.e.: lauric acid (C12), myristic acid (C14), and palmitic acid (C16) Obesity Lipids are fats. If a person consumes too many fats without burning them off, they get overweight and eventually obese.

References
http://www.vaxa.com/linoleic-acid.cfm http://ak47boyz90.files.wordpress.com/2009/07/picture 7.png?w=491&h=321 http://www.heart.org/HEARTORG/GettingHealthy/FatsA ndOils/Fats101/Saturated-Fats_UCM_301110_Article.jsp http://www.umass.edu/nibble/infofile/unsatfat.html http://webcache.googleusercontent.com/search?q=cache: WXGZeCkSZvEJ:dl.clackamas.edu/ch10606/hydrolys.htm+hydrolysis+of+fats&cd=1&hl=en&ct=cln k&gl=us