LIPIDS
- Comprise of very heterogeneous group of compounds
Heterogeneous – do not have common structural
feature that serves as the basis of what the Figure 2 Triacylglycerol
compound is.
- Largely hydrophobic
- Made up of Hydrocarbon molecules
Hydrocarbon – organic molecules consisting of Figure 1 Packing of
entirely carbon and hydrogen fatty acid into stable
- Non-informational macromolecules aggregate
2 Common Characteristics of Lipids:
Figure 4 Cholesterol
1. Low solubility in water
2. High solubility in organic non-polar solvents
Non-polar Solvents – ex. Benzene & Chloroform
FUNCTIONS
1. Fuel
Fat – is the most concentrated storage form of
energy
- Yields 9 calories per gram
Ex. Triglyceride (Triacylglycerol, TAG)
- can be hydrolyzed t be used for energy
- Used for storage of excess energy; stored in
adipose tissue
2. Thermal insulation CLASSIFICATION OF LIPIDS
Fat – known to protect animals from the cold
Adipose tissue - releases stored energy in the form I. Structure
of heat II. Ability to undergo hydrolysis under alkaline
condition
3. Cell membrane components
STRUCTURE
- Phospholipids, Glycolipids & Cholesterol
A. Simple Lipids – esters of fatty acids with various
4. Building blocks or precursors alcohols
- Building blocks to other biologically active - Can no longer be broken down into smaller units
materials i. Fats and oils – esters of fatty acids with
- Precursor of hormones and lipid soluble vitamins glycerol
- Serves as chemical mediators or messenger - Depending on the number of esterified
Ex. Prostaglandins – mediators of inflammatory acids
and anaphylactic reactions ii. Waxes – esters of fatty acids with high
Thromboxin – mediators of vasoconstriction molecular weight monohydric alcohols
B. Complex Lipids – esters of fatty acids and alcohols
5. Provides protection together with some other head groups
Fat – provides padding/ cushion to protect internal i. Phospholipids – lipids containing, in addition to
organs (vital organs are covered in adipose tissue) fatty acids and an alcohol, a phosphoric acids
residue
Glycerophospholipids – glycerol
6. Lipoproteins Spingophospholipids – sphingosine
Fat – serves as transporter in the form of ii. Glycolipids – lipids containing a fatty acid,
lipoproteins sphingosine and carbohydrate
ex. HDL (High Density Lipoproteins) & LDL
(Low Density Lipoproteins) C. Derived Lipids – these include byproducts of
metabolic process like fatty acids, glycerol, mono- and
7. Essential for normal growth and function diacylglycerols, lyphosphatidases, fatty aldehydes,
- Usually for brain development/ nervous tissue ketone bodies
STRUCTURAL DIVERSITY
D. Steroid Lipids – cholesterol, cholesteryl esters, a. Saturated Fatty Acids
cholesterol derivatives (with ring structure - No double bonds between carbons in the
chain
E. Miscellaneous Lipids – aliphatic hydrocarbons, - All carbon atoms are single bonded –
carotenoids, squalene, terpenes, vitamin E and K, filled with hydrogen atoms
glycerol ether, glycosyl glycerols - Solid at room temperature
- Higher melting temperature
ABILITY TO UNDERGO HYDROLYSIS UNDER
Melting temperature – temp at which a
ALKALINE CONDITION substance changes from solid to liquid
state
A. Saponifiable –exposure to alkaline medium will break - Straight chain (mol. are compact)
them down into simpler components
- Can be converted into 2 or more smaller molecules
when hydrolysis occurs
Ex. TAG, Phospholipids, Sphingoglycolipids, - Found in animals, butter, lard, palm
Biological Waxes coconut
- Must have: (at least 1)
o Ester bond
o Glycosidic bond b. Unsaturated Fatty Acids
o Amide bond - Contain 1 or more double bond
- Double bond appears as kinks –
B. Nonsaponifiable – lipids can no longer undergo contributes to the fluidity and permeability
hydrolyzation in an alkaline medium of the membrane, prevents efficient
- Only has 1 building block – does not need packing (mol not as compact)
bonds to link them together - Liquid at room temperature
- No site for hydrolysis to occur - Lower melting temperature
- Does not react with water
Ex. Cholesterol, Bile Acids, Steroid Hormones
FATTY ACIDS
- Most frequently encountered lipid building blocks Monosaturated – 1 C=C
- Starting point for the development of lipid Polyunsaturated – 2 or more C=C
chemistry
A. Characteristics and Structure
1. A carboxylic acid with long
chain ( R ) hydrocarbon side chain
2. Usually biosynthesized by linking 2 carbon units
(even number) 2 configurations of Unsaturated Fatty Acid:
3. Rarely found free in nature but occur in esterified
form as the major components of various lipids Cis configuration
B. Functions - H atoms are on the same side of the
1. Fuel Energy bond
2. Maintenance of membrane fluidity - Has a kink on the hydrocarbon chain
3. Components of food oils - Bent in 120o at the C=C
4. Growth and development
5. Precursor or long-chain unsaturated fatty acids
C. Classification
1. Length of the Hydrocarbon Tail Trans configuration
Type of Fatty Acid No. of Carbon - H atoms are on the opposite ends of the
Long chain 12 – 16 carbons
Medium chain 6 – 12 carbons
bond
Short chain < 6 carbons - Linear
*** Range may vary per reference - Behaves much like a saturated fatty acid
2. Degree of unsaturation
3. Source NOMENCLATURE OF FATTY ACIDS
a. Non-essential fatty acids
Carbon Skeleton
- Can be synthesized by the body
Ex. Palmitic acid, and other saturated - No. of Carbon : No. of Double Bond
and monoenoic FA’s - 12:0 = 12 Carbon : 0 double bond
b. Essential fatty acids - ∆ = where double bond is located
- Must be obtained from exogenous - 16:1(∆9) = 12 C : 1 DB (DB at C 9)
sources (diet)
- Plays a role in normal growth and Structure
development - CH2(CH2)10COOH
Ex. Breastmilk - CH3(CH2)5CH=CH(CH2)7COOH
Systematic Name
- n = normal unbranched structure
- 12 = dodeca
- n - Dodecanoic acid
- cis – 9- Hexadecenoic acid
- 9 = where DB is located
- decenoic – one double bond
- Linolenic Acid - Responsible for proper
- dienoic – 2 double bond
membrane structure
- trienoic – 3 double bond
- Serve as anti-inflammatory, prevents heart
disease, reduces risk of heart disease and Common Name
cancer
- Arachidonic Acid – regulate blood pressure, - usually comes from the source
blood clotting, and different body functions - “Lauric acid” – from laurel plant
GOOD FATS FATTY ACID NUMBERING
Monosaturated Polyunsaturated 1. Delta ∆ Numbering System
Canola oil, Olive oil, Most vegetable and seed - Starts with the carbonyl group (COOH) or delta
Olives, Avocado, oils, walnuts, brazil,
end
almonds, peanuts, nuts, pecans, pine nuts,
- Delta end’s hydrocarbon will be read as C1
cashews, hazelnuts, wheat germ, oily fish
macadamias, pistachios, and fish oils - Notation x : y ( ∆ m, n, …)
egg yolk - X – no. of C atoms
- Can decrease stickiness of platelets to prevent - Y – no. of double bonds
formation of blood clots, lower HDR, lessen - m, n, … - Positions of any double bonds,
the chance of getting cancer numbers following ∆ (delta)
- Polyunsaturated- can be good or bad- can
promote the risk of certain types of cancer
18 : 2 ( ∆9, 12)
BAD FATS
Saturated Trans 2. Omega ( ω ) Numbering System
Fatty meats, chicken Biscuits, cakes, pastries - Starts with the methyl end (H3C or CH3) or
skin, butter, cream, and doughnuts omega end
cheese, ice cream, deep - Omega ( ω ) ends hydrocarbon will be read as
fried, take away and fast C1
food
- Can increase cardiovascular disease risk
- Trans – produced by partial hydrogenization
of unsaturated fatty acids
Omega System: ω – 6,9
