Fatty Acids 2
Fatty Acids 2
PHARM-317
Lecture 11
“Fatty Acids”
Discussion Outlines
Fatty Acids
Course: Biochemistry-II, PHARM-317 -- Instructor: Dr. Majeedullah, Assistant. Prof. Department of Pharmacy, KUST -- Email: [email protected]
Fatty acids
Fatty acids are long-chain hydrocarbons, containing a
carboxylic acid functional group, which is the reactive portion
of the molecule.
Course: Biochemistry-II, PHARM-317 -- Instructor: Dr. Majeedullah, Assistant. Prof. Department of Pharmacy, KUST -- Email: [email protected]
Fatty acids
The fatty acids may be saturated (containing no double bond) or
unsaturated (containing one or more double bond).
Course: Biochemistry-II, PHARM-317 -- Instructor: Dr. Majeedullah, Assistant. Prof. Department of Pharmacy, KUST -- Email: [email protected]
Nomenclature of fatty acids
The most commonly used systematic nomenclature is naming the
fatty acid according to number of carbon atoms and the word –oic
acid being substituted for the final -e (Genevan system).
Thus, saturated acids end in –anoic acid, e.g., octanoic acid, and
unsaturated acids (having double bonds) end with –enoic acid,
e.g., octadecenoic acid (oleic acid).
Course: Biochemistry-II, PHARM-317 -- Instructor: Dr. Majeedullah, Assistant. Prof. Department of Pharmacy, KUST -- Email: [email protected]
Nomenclature of fatty acids
The second number should always be zero in case of saturated
fatty acids.
Carbon atoms are numbered from the carboxyl carbon (carbon No.
1).
Course: Biochemistry-II, PHARM-317 -- Instructor: Dr. Majeedullah, Assistant. Prof. Department of Pharmacy, KUST -- Email: [email protected]
Nomenclature of fatty acids
Δ is usually used for indicating the number and position of the
double bonds; for example, Δ9 indicates a double bond between
carbons 9 and 10 of the fatty acid; ω9 indicates a double bond on
the ninth carbon counting from the ω- carbon.
Course: Biochemistry-II, PHARM-317 -- Instructor: Dr. Majeedullah, Assistant. Prof. Department of Pharmacy, KUST -- Email: [email protected]
Saturated fatty acids
These are fatty acids which do not have any double bond in their
structure.
Plant Oils: Some oils like coconut oil and palm oil are high in
saturated fats
Course: Biochemistry-II, PHARM-317 -- Instructor: Dr. Majeedullah, Assistant. Prof. Department of Pharmacy, KUST -- Email: [email protected]
Saturated fatty acids
The most important saturated fatty acids with their formula and
symbol are given below:
S. No. Common Name Formula Symbol Sources
1 Butyric acid C3H7COOH 4:0 Butter
Goat and Cow
2 Caproic acid C5H11COOH 6:0
milk
Palm oil, animal
3 Palmitic acid C15H31COOH 16:0
fats
Cocoa butter,
4 Stearic acid C17H35COOH 18:0 animal fats
Course: Biochemistry-II, PHARM-317 -- Instructor: Dr. Majeedullah, Assistant. Prof. Department of Pharmacy, KUST -- Email: [email protected]
Unsaturated fatty acids
These fatty acids are much more reactive than saturated
fatty acids.
Course: Biochemistry-II, PHARM-317 -- Instructor: Dr. Majeedullah, Assistant. Prof. Department of Pharmacy, KUST -- Email: [email protected]
Unsaturated fatty acids
These fatty acids are much more reactive than saturated fatty
acids. Unsaturated fatty acids contain one or more double
bonds and may be:
Course: Biochemistry-II, PHARM-317 -- Instructor: Dr. Majeedullah, Assistant. Prof. Department of Pharmacy, KUST -- Email: [email protected]
S. Common
Formula Symbol Sources
No. Name
Palmito-oleic C15H29COO Nut and Fish
1 16:1 Δ9
acid H
C17H33COO olive oil and nuts
2 Oleic acid 18:1 Δ 9
H
C17H31COO
3 Linoleic acid 18:2 Δ9,12 Soybean & sunflower oil
H
α-Linolenic C17H29COO 18:3
4 Flaxseed oil, wulnuts
acid H Δ9,12,15
γ-Linolenic C17H29COO
5 18:3 Δ6,9,12
acid H
Arachidonic C19H31COO 20:4
6 Liver and egg yolk
acid H Δ5,8,11,14
a: Geometric isomerism
b: Positional isomerism
Course: Biochemistry-II, PHARM-317 -- Instructor: Dr. Majeedullah, Assistant. Prof. Department of Pharmacy, KUST -- Email: [email protected]
Isomerism in unsaturated fatty acids
a: Geometric Isomerism
Course: Biochemistry-II, PHARM-317 -- Instructor: Dr. Majeedullah, Assistant. Prof. Department of Pharmacy, KUST -- Email: [email protected]
a: Geometric Isomerism
For example, an 18-carbon fatty acid with two double bonds can exist
as:
Course: Biochemistry-II, PHARM-317 -- Instructor: Dr. Majeedullah, Assistant. Prof. Department of Pharmacy, KUST -- Email: [email protected]
Essential fatty acids
The polyunsaturated fatty acids that cannot be produced by
the body but are important for health and growth are called
essential fatty acids.
Course: Biochemistry-II, PHARM-317 -- Instructor: Dr. Majeedullah, Assistant. Prof. Department of Pharmacy, KUST -- Email: [email protected]
Types of Essential Fatty Acids
Omega-3 Fatty Acids
Linoleic acid (LA): The primary omega-6 fatty acid found in vegetable
oils such as sunflower, corn and soybean oil. (Essentail FA)
Note: Other derivatives include arachidonic acid (AA), which is
synthesized from linoleic acid and plays a role in inflammatory
responses.
Course: Biochemistry-II, PHARM-317 -- Instructor: Dr. Majeedullah, Assistant. Prof. Department of Pharmacy, KUST -- Email: [email protected]
Health Benefits of Essential Fatty Acids
Cell Membrane Integrity
Eicosanoid Production
Cognitive Function
Course: Biochemistry-II, PHARM-317 -- Instructor: Dr. Majeedullah, Assistant. Prof. Department of Pharmacy, KUST -- Email: [email protected]
Eicosanoids
Eicosanoids are biologically active lipid derivatives primarily derived from
arachidonic acid
Types
Prostaglandins has role in inflammation, smooth muscle contraction, and
regulation of blood flow
Thromboxanes TXA2 promotes platelet aggregation and vasoconstriction
Leukotrienes They are primarily involved in inflammatory responses and allergic
reactions, such as asthma.
Lipoxins are involved in resolving inflammation and promoting tissue repair.
Synthesis of Eicosanoids
Eicosanoids are synthesized from arachidonic acid, which is released
from membrane phospholipids by the action of phospholipase A2. The
synthesis pathways include:
Cyclooxygenase Pathway
Involves the conversion of arachidonic acid to prostaglandin H2 through
cyclooxygenase enzymes (COX-1 and COX-2), leading to the production
of prostaglandins and thromboxanes.
Lipoxygenase Pathway
Involves the conversion of arachidonic acid to leukotrienes via
lipoxygenase enzymes.
Physical properties of fatty acids
a: Melting point
Course: Biochemistry-II, PHARM-317 -- Instructor: Dr. Majeedullah, Assistant. Prof. Department of Pharmacy, KUST -- Email: [email protected]
Name of Fatty No of double Melting point
acid bond
Oleic acid 1 14 Ċ
Linoleic acid 2 -5 Ċ
Melting Point
o Higher the degree of saturation and higher the chain length then
higher will be their melting point.
o Vegetable oils like cotton seed oil, corn oil, soya been oil etc.
have excess of unsaturated fatty acid and are liquid at room
temperature.
o On hydrogenation under pressure and in the presence of nickel,
oil becomes saturated and their melting point increase as a
result they become solidified (banaspati).
Course: Biochemistry-II, PHARM-317 -- Instructor: Dr. Majeedullah, Assistant. Prof. Department of Pharmacy, KUST -- Email: [email protected]
b: Polymorphism
The higher fatty acids can exist in two or three crystalline forms
depending upon the temperature and solvent of crystallization.
c: Solubility
But the acids higher than C6 are only slightly soluble in water.
Course: Biochemistry-II, PHARM-317 -- Instructor: Dr. Majeedullah, Assistant. Prof. Department of Pharmacy, KUST -- Email: [email protected]
d: Boiling point
Course: Biochemistry-II, PHARM-317 -- Instructor: Dr. Majeedullah, Assistant. Prof. Department of Pharmacy, KUST -- Email: [email protected]
Chemical properties of fatty acids
1. Formation of salts (Soaps)
o The fatty acids form salts with alkali metals and alkaline earth
metals.
o The Na and K salts are soluble in water while Ca and Mg salts are
insoluble in water.
o K salts are too much soluble and can’t form cake soap and are
thus used in liquid state.
Course: Biochemistry-II, PHARM-317 -- Instructor: Dr. Majeedullah, Assistant. Prof. Department of Pharmacy, KUST -- Email: [email protected]
Chemical properties of fatty acids
Formation of detergents
Course: Biochemistry-II, PHARM-317 -- Instructor: Dr. Majeedullah, Assistant. Prof. Department of Pharmacy, KUST -- Email: [email protected]
Chemical properties of fatty acids
Formation of detergents
Course: Biochemistry-II, PHARM-317 -- Instructor: Dr. Majeedullah, Assistant. Prof. Department of Pharmacy, KUST -- Email: [email protected]
Chemical properties of fatty acids
3. Formation of esters
Course: Biochemistry-II, PHARM-317 -- Instructor: Dr. Majeedullah, Assistant. Prof. Department of Pharmacy, KUST -- Email: [email protected]
Chemical properties of fatty acids
4. Formation of eicosanoids (signaling molecules)
Course: Biochemistry-II, PHARM-317 -- Instructor: Dr. Majeedullah, Assistant. Prof. Department of Pharmacy, KUST -- Email: [email protected]
Chemical properties of fatty acids
Special reactions of unsaturated fatty acids
Hydrogenation
Course: Biochemistry-II, PHARM-317 -- Instructor: Dr. Majeedullah, Assistant. Prof. Department of Pharmacy, KUST -- Email: [email protected]
Fats or Neutral Fats or Triglycerides or Triglycerols
These are the esters of fatty acids with glycerol and are most
common and widespread class of lipids in nature.
Course: Biochemistry-II, PHARM-317 -- Instructor: Dr. Majeedullah, Assistant. Prof. Department of Pharmacy, KUST -- Email: [email protected]
Fats or Neutral Fats or Triglycerides or Triglycerols
a: Physical properties of fats
Course: Biochemistry-II, PHARM-317 -- Instructor: Dr. Majeedullah, Assistant. Prof. Department of Pharmacy, KUST -- Email: [email protected]
Fats or Neutral Fats or Triglycerides or Triglycerols
Chemical properties of fats
Hydrolysis
R2 C O C H O + 3H2O HO C H + R2 COOH
Course: Biochemistry-II, PHARM-317 -- Instructor: Dr. Majeedullah, Assistant. Prof. Department of Pharmacy, KUST -- Email: [email protected]
Fats or Neutral Fats or Triglycerides or Triglycerols
Chemical properties of fats
2. Saponification and saponification number
Course: Biochemistry-II, PHARM-317 -- Instructor: Dr. Majeedullah, Assistant. Prof. Department of Pharmacy, KUST -- Email: [email protected]
Fats or Neutral Fats or Triglycerides or Triglycerols
Chemical properties of fats
2. Saponification and saponification number
Fats with short-chain fatty acids have more ester bonds per
gram than those with long-chain fatty acids, requiring more
KOH for saponification, thus have higher saponification No.
Course: Biochemistry-II, PHARM-317 -- Instructor: Dr. Majeedullah, Assistant. Prof. Department of Pharmacy, KUST -- Email: [email protected]
Fats or Neutral Fats or Triglycerides or Triglycerols
Chemical properties of fats
2. Saponification and saponification number
Course: Biochemistry-II, PHARM-317 -- Instructor: Dr. Majeedullah, Assistant. Prof. Department of Pharmacy, KUST -- Email: [email protected]
Fats or Neutral Fats or Triglycerides or Triglycerols
Chemical properties of fats
Reaction due to unsaturation: iodine number
Course: Biochemistry-II, PHARM-317 -- Instructor: Dr. Majeedullah, Assistant. Prof. Department of Pharmacy, KUST -- Email: [email protected]
Fats or Neutral Fats or Triglycerides or Triglycerols
Chemical properties of fats
Reaction due to unsaturation: iodine number
Course: Biochemistry-II, PHARM-317 -- Instructor: Dr. Majeedullah, Assistant. Prof. Department of Pharmacy, KUST -- Email: [email protected]
Fats or Neutral Fats or Triglycerides or Triglycerols
Chemical properties of fats
Reaction due to unsaturation: iodine number
Course: Biochemistry-II, PHARM-317 -- Instructor: Dr. Majeedullah, Assistant. Prof. Department of Pharmacy, KUST -- Email: [email protected]
Fats or Neutral Fats or Triglycerides or Triglycerols
Chemical properties of fats
Reaction due to unsaturation: iodine number
Iodine number of some common
fats
Fat Iodine number
Coconut oil 6 to 10
Butter fat 26 to 28
Beef fat 35 to 42
Human fat 65 to 69
Olive oil 79 to 88
Cottonseed oil 103 to 111
Course: Biochemistry-II, PHARM-317 -- Instructor: Dr. Majeedullah, Assistant. Prof. Department of Pharmacy, KUST -- Email: [email protected]
Fats or Neutral Fats or Triglycerides or Triglycerols
Chemical properties of fats
Rancidity
Course: Biochemistry-II, PHARM-317 -- Instructor: Dr. Majeedullah, Assistant. Prof. Department of Pharmacy, KUST -- Email: [email protected]
Fats or Neutral Fats or Triglycerides or Triglycerols
Types of Rancidity
Oxidative Rancidity:
This occurs when unsaturated fats react with oxygen, leading to the
formation of peroxides, aldehydes, and ketones. These compounds
contribute to off-flavors and odors in food
Hydrolytic Rancidity:
Types of Rancidity
Microbial Rancidity: Caused by microbial action, this form involves
bacteria producing enzymes that break down fats, leading to rancid
flavors
Enzymatic Rancidity: Similar to microbial rancidity, this occurs due
to the action of enzymes on fats, resulting in the formation of free
fatty acids
.
Photooxidative Rancidity: This type is triggered by exposure to
light, particularly UV light, which accelerates the oxidation process
Note: To prevent oxidation and extend the shelf life of oils, antioxidants like tocopherols
, BHA, and BHT can be used to neutralize free radicals. Additionally, agents like citric acid or EDTA bind metal ions to stop them from tri
ggering oxidation.
.
Course: Biochemistry-II, PHARM-317 -- Instructor: Dr. Majeedullah, Assistant. Prof. Department of Pharmacy, KUST -- Email: [email protected]
Fats or Neutral Fats or Triglycerides or Triglycerols
Chemical properties of fats
Rancidity
Course: Biochemistry-II, PHARM-317 -- Instructor: Dr. Majeedullah, Assistant. Prof. Department of Pharmacy, KUST -- Email: [email protected]
Importance of lipids
Lipids are good source of energy and provide 9.1 Kcal/g of fats
utilized in the body.
They also act as carrier for the fat-soluble vitamins and the
essential fatty acids present in the fat of natural foods.
They also make the food more palatable and decrease its mass.
Body fats provide contour to the body and also give anatomical
stability to the organs.
Course: Biochemistry-II, PHARM-317 -- Instructor: Dr. Majeedullah, Assistant. Prof. Department of Pharmacy, KUST -- Email: [email protected]
Importance of lipids
Fat is stored in adipose tissue, It also serves as a thermal
insulator in the subcutaneous tissues and around certain
organs.
Course: Biochemistry-II, PHARM-317 -- Instructor: Dr. Majeedullah, Assistant. Prof. Department of Pharmacy, KUST -- Email: [email protected]
Importance of lipids
Presence of lipids like cholesterol in the skin makes it highly
resistant to the water-soluble substances and also to the action of
many chemical agents.
The lipids also help to prevent the evaporation of water from the
skin.
Knowledge of lipid biochemistry is necessary in understanding
many important biomedical areas, e.g., obesity, diabetes mellitus,
atherosclerosis, and nutrition and health.
Eicosanoids are lipids in nature. They formed from 20-carbon
polyunsaturated fatty acids and make up an important group of
physiologically and pharmacologically active compounds known as
prostaglandins, thromboxanes, leukotrienes, and lipoxins.
Course: Biochemistry-II, PHARM-317 -- Instructor: Dr. Majeedullah, Assistant. Prof. Department of Pharmacy, KUST -- Email: [email protected]
Importance of lipids
Phosphoacylglycerols are amphipathic lipids and have important
roles as major constituents of membranes and the outer layer of
lipoproteins.
Glycolipids are also important constituents of nervous tissue
such as brain and the outer leaflet of the cell membrane.
Cholesterol, an amphipathic lipid, is an important component of
membranes. It is the parent molecule from which all other
steroids in the body are synthesized including major hormones
such as the adrenocortical and sex hormones, vitamins D, and
bile acids.
Peroxidation of lipids containing polyunsaturated fatty acids
leads to generation of free radicals that may damage tissues and
cause disease.
Course: Biochemistry-II, PHARM-317 -- Instructor: Dr. Majeedullah, Assistant. Prof. Department of Pharmacy, KUST -- Email: [email protected]
THANK YOU
Course: Biochemistry-II, PHARM-317 -- Instructor: Dr. Majeedullah, Assistant. Prof. Department of Pharmacy, KUST -- Email: [email protected]
References
1:http
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www.rpi.edu/dept/bcbp/molbiochem/MBWeb/mb1/part2/lipid.htm&u
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2:http
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WUM-Pv6uHE=&h=441&w=418&sz=10&hl=en&start=17&tbnid=manKm
Course: Biochemistry-II, PHARM-317 -- Instructor: Dr. Majeedullah, Assistant. Prof. Department of Pharmacy, KUST -- Email: [email protected]
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Topic: β-Oxidation of Fatty Acids
Thank you …
Course: Biochemistry-II, PHARM-317 -- Instructor: Dr. Majeedullah, Assistant. Prof. Department of Pharmacy, KUST -- Email: [email protected]