Lipid Chemistry (ppt) Flashcards
It is the fraction of any biological material that is 💡insoluble in water but 💡soluble in one or more solvents of low polarity.
A heterogenous group of compounds that include fatty acids, fats and oils, waxes, steroids, phospholipids & sphingolipids.
Lipid
What are the two major functions of lipids?
- Source of energy
2. Important component of cellular structure
Classification of Lipids:
- Simple lipids
- Complex lipids
- Precursor and derived lipids
These are classification of lipids which contains 💡esters of fatty acids with 💡various alcohols
Simple lipids
It is a simple lipid which contain 💡esters of fatty acids with 💡glycerol
Triacylglycerol (triglycerides)
These are simple lipids which contain 💡esters of fatty acids with 💡higher molecular weight monohydric
alcohols
Waxes
These are classification of lipids which contains 💡esters of fatty acids with 💡various alcohols plus an 💡additional functional group.
Complex (Compound) Lipids
These are complex lipid where there is a 💡phosphate group present.
Phospholipids
These are complex lipid which contain 💡carbohydrates
Glycolipids
These are complex lipid which are 💡hybrid molecules of lipids and 💡apoproteins
Lipoproteins
General Properties of Lipids
- Insoluble in water but soluble in one or more solvents of low polarity such as chloroform, acetone, alcohol and benzene
- Esters of fatty acid or capable of forming such esters.
- Utilizable by the living organism.
General Properties of Fatty Acids
- Monocarboxylic acids with hydrocarbon residues that are acyclic and unbranched.
- Number of carbon atoms is in most cases even.
- May or may not contain double bonds
No double bonds
Abundant in animal fats
Saturated fatty acids
They have double bonds
Abundant in plant and fish oils
Unsaturated fatty acids
They have one double bond
Ex: Palmitoleic acid (16:1) & Oleic acid (18:1)
Monounsaturated fatty acids
They have two or more double bonds.
Ex: omega-3 and omega-6 fatty acids
Polyunsaturated fatty acids
They are derived from eicosa-(20 C) polyenoic fatty acids.
Ex: Prostanoids & leukotrienes
Eicosanoids
Nutritional Classification of Fatty Acids
- Nonessential fatty acids
2. Essential fatty acids
These are nutritional fatty acids that 💡can be synthesized in our body.
Ex: saturated fatty acids, palmitoleic acid and oleic acid
Nonessential fatty acids
These are nutritional fatty acids that 💡cannot be synthesized in our body.
Ex: omega-3 and omega-6 fatty acids
Essential fatty acids
These are the truly essential fatty acids
Linoleic acid and alpha-linolenic acid
Examples of Omega-3 fatty acids:
a) Alpha-linolenic acid (cis-9,12,15 - octadecatrienoic acid)
b) Timnodonic acid (cis-5,8,11,14,17 – eicosapentaenoic acid)
c) Cervonic acid (cis-4,7,10,13,16,19 – docosahexaenoic acid)
Examples of Omega-6 fatty acids:
a) Linoleic acid (cis-9,12- octadecadienoic acid)
b) Gamma-linolenic acid (cis-6,9,12 – octadecatrienoic acid)
c) Arachidonic acid (cis-5,8,11,14 – eicosatetraenoic acid)
Alternating single and double bond.
Conjugated Double Bond
Optimal ratio of omega 6 to omega 3 PUFA is between:
1:1 and 4:1
-
Methylene interrrupted double bond
Fatty acid with 💡more than 12 carbon atoms
Long-chain fatty acids
Using the 💡symbol delta plus a superscript number, the reference point is the?
Carboxyl group as C-1
Using the 💡symbol omega plus a number beside it reference point is the?
Methyl carbon as C-1
It refer to the type of 💡geometric isomerism that occur in unsaturated fatty acids depending on the 💡orientation of the acyl groups around the 💡axes of double bonds.
Cis
Trans
An isomerism formed when the 💡acyl groups are on the 💡same side of the bond; produces a 💡kink
Cis Isomerism
An isomerism formed when the 💡acyl groups are on the 💡opposite side.
Trans Isomerism
It is a 💡by product of hydrogenation or hardening of natural oils in the manufacture of margarine.
Increased risk of CVD and DM
It raises the levels of TAG and LDL
Trans Fatty Acid
Gamma linoleic acid (18:3;6,8,12)
1st digit is the number of carbon atoms
2nd digit is the number of double bonds.
Succeeding number after the 2nd bond is the location of the double bonds.
Medium chain fatty acid (rich in Philippines)
Lauric Acid
Coconut oil
See anki for the table
Physical Properties of Fatty Acids
Deleterious effects of trans fats occur at intakes of:
2-7 g/day
Examples of 💡soluble soaps:
Sodium & potassium soaps (e.g. sodium oleate)
Examples of 💡insoluble soaps:
Calcium & magnesium soaps (e.g. calcium palmitate)
It is a reaction between the 💡carboxyl group of the fatty acid and the 💡hydroxyl group of an alcoholic substance forming an 💡ester compound linked by an 💡ester bond.
Esterification
It refers to 💡fatty acid residues.
Acyl group
Chemical reactions of fatty acids:
Saponification
Esterification
Reactions of double bonds
Oxidation of the double bonds
Only 💡unsaturated fatty acids will give these kind of reactions
Reactions of double bonds
Soap formation
Saponification reaction
It is a reaction with hydrogen forming 💡saturated fatty acids
It is the principal reaction behind manufacturing of solid shortenings, e.g., margarine
Hydrogenation reaction
It is a reaction with 💡halogens like iodine forming 💡iodinated saturated fatty acids
The reaction involved in a chemical test – Iodine number
Halogenation reaction
Test to determine the 💡degree of unsaturation
Directly proportional
Iodine number
💡In vitro oxidation of double bonds that causes formation of short-chain fatty acid aldehyde producing 💡rancid fat.
Rancidification
💡In vivo oxidation of fatty acid that forms ROS (free radicals) that causes the following:
- destroy the integrity of cell membranes
- cause cancer
- aging of tissues
- implicated in degenerative diseases
Lipid Peroxidation (auto-oxidation)
These are compounds that 💡inhibit oxidation
Antioxidants
It contains 💡three fatty acids are esterified to 💡one glycerol
- Primary ester bonds – 1st and 3rd carbon atoms
- Secondary ester bond – 2nd carbon atom (asymmetric/ chiral)
- Note: Fatty acid in carbon 2 is usually 💡unsaturated
💡Most abundant naturally occurring lipid
💡Most abundant dietary lipid
💡Chief storage form of energy in our body; stored mostly in 💡adipose tissue
¨Adipose tissue under the skin also serve as 💡insulation against low temperatures
¨💡Neutral fat since it does not have any charge
¨Other neutral fats: monoacylglycerol & diacylglycerol
Triacylglycerol (Triglyceride)
Salts of fatty acid
Maybe soluble or insoluble to water
Soaps
Classification of Triacylglycerol (TAG)
- According to number of kinds of fatty acids present
2. According to length of hydrocarbon residues of the fatty acids present in TAG
According to number of kinds of fatty acids present
- Simple TAG
2. Mixed TAG
All three fatty acids are the same e.g., tripalmitin, triolein, triarachidonin
SIMPLE TAG
There are 💡two or three different kinds of fatty acids esterified to glycerol
MIXED TAG
The mixed TAG are more__ than simple TAG.
common
Fatty acid with 💡2 to 4 carbon atoms
Short-chain fatty acids
Example of esterification reaction:
Triglyceride synthesis
Examples of reaction of double bonds:
Hydrogenation reaction
Halogenation reaction
Advantages of TAG as stored fuel:
- C atoms are more reduced; yields more energy.
2. Hydrophobic unhydrated; does not have to carry extra weight of water.
PHYSICAL Properties of TAG:
Depends on the kind of fatty acids esterified to TAG
💡Fats are TAG that are solid at room temp. (Presence of more long chain saturated FA e.g. lard)
💡Oils are TAG that are liquid at room temp. (Presence of more unsaturated FA e.g. cooking oils)
- 💡Acid (e.g. HCl) or 💡enzyme (lipase) is used as the hydrolyzing agents
- Products of hydrolysis are 💡free fatty acids & 💡glycerol
- Fatty acids are insoluble in water
- Reaction is 💡reversible
ORDINARY HYDROLYSIS
- 💡NaOH or 💡KOH are used as the hydrolyzing agents
- Products of hydrolysis are 💡Na or 💡K soap and 💡glycerol
- The soaps are 💡soluble in water
- Basis of the chemical test – 💡Saponification Number
- Reaction is 💡irreversible
Alkali hydrolysis (saponification reaction)
It determines the 💡degree of unsaturation of a given fat or oil.
💡More double bonds, 💡the higher the iodine number.
Iodine number