1. Online Counseling Resource YCMOU ELearning Drive… School of Architecture, Science and Technology Yashwantrao Chavan Maharashtra Open University, Nashik – 422222, India

2. OC-SBT/ SBI/ SGS031-U02-02 Introduction Programmes and Courses  SEP – SBT031 – Unit 02  SEP – SBI031 – Unit 02  SEP – SGS031 – Unit 02

3. School of Science and Technology, Online Counseling Resource… © 2007, YCMOU. All Rights Reserved.3 Credits  Academic Inputs by Mrs. Rasika Bhore  M.sc ( Microbiology) rasika.bhore@gmail.com

4. School of Science and Technology, Online Counseling Resource… © 2007, YCMOU. All Rights Reserved.4 How to Use This Resource  Counselor at each study center should use this presentation to deliver lecture of 40-60 minutes during Face-To-Face counseling.  Discussion about students difficulties or tutorial with assignments should follow the lecture for about 40-60 minutes.  Handouts (with 6 slides on each A4 size page) of this presentation should be provided to each student.  Each student should discuss on the discussion forum all the terms which could not be understood. This will improve his writing skills and enhance knowledge level about topics, which shall be immensely useful for end exam.  Appear several times, for all the Self-Tests, available for this course.  Student can use handouts for last minutes preparation just before end exam.

5. School of Science and Technology, Online Counseling Resource… © 2007, YCMOU. All Rights Reserved.5 Learning Objectives  After studying this module, you should be able to: Define Fatty acids. Describe nomenclature, functions & classification of fatty acids. Enlist the names of fatty acids. Describe essential & free fatty acids. Describe cis & trans fatty acids.

6. School of Science and Technology, Online Counseling Resource… Introduction  Fatty acids are carboxylic acids with long hydrocarbon chain.  Molecular formula: R-COOH, R is hydrocarbon chain.  Fatty acids are Amphipathic in nature that means they have hydrophilic & hydrophobic groups in the structure.  Fatty acids are the building blocks of two types of lipid storage fats and the structural phospholipids.  Also serve as a precursor for all kind of lipids. © 2007, YCMOU. All Rights Reserved.6

7. School of Science and Technology, Online Counseling Resource… Nomenclature Of Fatty Acids  Fatty Acids have trivial names and systematic names.  The systematic name is derived from the name of its parent hydrocarbon.  Saturated FA ends with suffix “anoic", For e.g. C 18 octadecane is parent so octadecanoic acid is the FA.  Unsaturated FA end with suffix “enoic”,for e.g. C 18 is called as octadecenoic acid.  The carbon atoms of a FA are numbered starting at the carbonyl end and C 2 and C 3 are called alpha and beta respectively.  The methyl carbon atom at the distal end of the chain is called ‘ω’ carbon. © 2007, YCMOU. All Rights Reserved.7

8. School of Science and Technology, Online Counseling Resource… Representation of Double Bond of Fatty Acid  Two systems are used to designate the position of double bond: 1.C-system 2.ω-(omega) or n-system  In C-system, position of double bond is represented by ∆(delta) followed by a superscript number. e.g. oleic acid C 18,having one double bond between carbon 9 & 10 is represented as- C : 18 : ∆ 9 © 2007, YCMOU. All Rights Reserved.8

9. School of Science and Technology, Online Counseling Resource… ω- or n-system  In this system, ‘ω’ or ‘n’ refers to the carbon of their terminal methyl group.  In this system the oleic acid is denoted as- C:18:1:ω9 indicate that: It has 18 carbon atoms & one double bond. ω-9 represents the double bond position which is found between 9 th & 10 th carbon atoms. This method is widely used by nutritionists.  Naturally occurring unsaturated FA belong to ω-9,ω-6 & ω-3 series. For example, ω-9 or n-9 : oleic acid (C:18:1:ω-9 )-double bond between 9 th & 10 th carbon. ω-6 or n-6 : Archidonic acid (C:20:4:ω-6)-first double bond between 6 th & 7 th carbon. ω-3 or n-3 : Linolenic acid ( C:18:3:ω-3)-first double bond between 3 rd & 4 th carbon. 18 17 16 15 14 13 12 11 10 9 8 7 6 5 4 3 2 1 CH 3 CH 2 CH 2 CH 2 CH 2 CH=CHCH 2 CH=CHCH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 COOH 9,12-octadecadienoic acid (Linoleic Acid) © 2007, YCMOU. All Rights Reserved.9

10. School of Science and Technology, Online Counseling Resource… Classification of Fatty Acids Fatty acids mainly classified into two groups: Straight chain fatty acids Saturated fatty acids Unsaturated fatty acids Mono- unsaturated fatty acids Poly-unsaturated fatty acids Branched chain fatty acids © 2007, YCMOU. All Rights Reserved.10

11. School of Science and Technology, Online Counseling Resource… Straight Chain Fatty Acids  Fatty acids in which the carbons are arranged linearly. © 2007, YCMOU. All Rights Reserved.11

12. School of Science and Technology, Online Counseling Resource… Saturated Fatty Acids  Saturated fatty acids do not contain any double bonds.  The term "saturated" refers to hydrogen, in that all carbons (apart from the carboxylic acid [-COOH] group) contain as many hydrogens as possible. In other words, the (ω) end contains 3 hydrogens (CH 3 -) and each carbon within the chain contains 2 hydrogen  Saturated fatty acids form straight chains and, as a result, can be packed together very tightly, allowing living organisms to store chemical energy very densely.  The fatty tissues of animals contain large amounts of long-chain saturated fatty acids. (CH 3 -CH 2 -CH 2 -CH 2 -CH 2 -CH 2 -CH 2 -CH 2 -CH 2 -CH 2 -CH 2 -CH 2 -CH 2 -CH 2 -CH 2 -COOH) Palmitic acid © 2007, YCMOU. All Rights Reserved.12

13. School of Science and Technology, Online Counseling Resource… Some Saturated Fatty Acids © 2007, YCMOU. All Rights Reserved.13 Common nameIUPAC nameChemical structureAbbr. ButyricButanoic acidCH 3 (CH 2 ) 2 COOHC4:0 CaproicHexanoic acidCH 3 (CH 2 ) 4 COOHC6:0 CaprylicOctanoic acidCH 3 (CH 2 ) 6 COOHC8:0 CapricDecanoic acidCH 3 (CH 2 ) 8 COOHC10:0 LauricDodecanoic acidCH 3 (CH 2 ) 10 COOHC12:0 MyristicTetradecanoic acidCH 3 (CH 2 ) 12 COOHC14:0 PalmiticHexadecanoic acidCH 3 (CH 2 ) 14 COOHC16:0 StearicOctadecanoic acidCH 3 (CH 2 ) 16 COOHC18:0 ArachidicEicosanoic acidCH 3 (CH 2 ) 18 COOHC20:0 BehenicDocosanoic acidCH 3 (CH 2 ) 20 COOHC22:0

14. School of Science and Technology, Online Counseling Resource… Unsaturated Fatty Acids  These contains double bonds in their carbon chains.  carbon atoms in the chain that are bound to either side of the double bond can occur in a cis or trans configuration. © 2007, YCMOU. All Rights Reserved.14

15. School of Science and Technology, Online Counseling Resource… Trans & Cis Fatty Acids  Nearly all double bonds in naturally occurring fatty acids in humans, plants & animals are of the Cis configuration.  A trans double bonds are characteristically produced during industrial hydrogenation of plant oils.  The purpose of hydrogenation is to change the physical properties of oils into solid products which are easier to manipulate. © 2007, YCMOU. All Rights Reserved.15

16. School of Science and Technology, Online Counseling Resource… Monounsaturated & Polyunsaturated  Monounsaturated or monoenoic fatty acids carry a single double bond in the molecules. e.g. Oleic acid (c : 18 : 1 : ω-9 )  Polyunsaturated or polyenoic fatty acids contains one or more double bonds in the molecules, for example- Dienoic acids:-2 double bonds,e.g. Linolenic acid; present in soyabean,sunflower,saffola & ground nut oils. Trienolic acid:- 3 double bonds,e.g. Linolenic acid; present in poppy seed oil,inseed oil. Tetraenolic acid:- 4 double bonds. e.g. Archidonic acid; present in ground nuts. © 2007, YCMOU. All Rights Reserved.16

17. School of Science and Technology, Online Counseling Resource… Some Unsaturated Fatty Acids © 2007, YCMOU. All Rights Reserved.17 Common name Chemical structureω ΔAbbr. Myristoleic acidCH 3 (CH 2 ) 3 CH=CH(CH 2 ) 7 COOHω-5cis-Δ 5 C14:1 Palmitoleic acidCH 3 (CH 2 ) 5 CH=CH(CH 2 ) 7 COOHω-7cis-Δ 7 C16:1 Oleic acidCH 3 (CH 2 ) 7 CH=CH(CH 2 ) 7 COOHω-9cis-Δ 9 C18:1 Linoleic acidCH 3 (CH 2 ) 4 CH=CHCH 2 CH=CH(CH 2 ) 7 COOHω-6cis, cis-Δ 6, Δ 9 C18:2 Alpha-linolenic acid CH 3 CH 2 CH=CHCH 2 CH=CHCH 2 CH=CH(CH 2 ) 7 COOHω-3 cis, cis, cis-Δ 3, Δ 6, Δ 9 C18:3 Arachidonic acid CH 3 (CH 2 ) 4 CH=CHCH 2 CH=CHCH 2 CH=CHCH 2 CH=CH(CH 2 ) 3 COOH ω-6 cis, cis, cis, cis-Δ 6, Δ 9, Δ 12, Δ 15 C20:4 Eicosapentaen oic acid CH 3 CH 2 CH=CHCH 2 CH=CHCH 2 CH=CHCH 2 CH=CHCH 2 CH=CH (CH 2 ) 3 COOH ω-3 cis, cis, cis, cis, cis-Δ 3, Δ 6, Δ 9, Δ 12, Δ 15 C20:5 Erucic acidCH 3 (CH 2 ) 7 CH=CH(CH 2 ) 11 COOHω-9cis-Δ 9 C22:1 Docosahexaen oic acid CH 3 CH 2 CH=CHCH 2 CH=CHCH 2 CH=CHCH 2 CH=CHCH 2 CH=CH CH 2 CH=CH(CH 2 ) 2 COOH ω-3 cis, cis, cis, cis, cis, cis-Δ 3, Δ 6, Δ 9, Δ 12, Δ 15, Δ 18 C22:6

18. School of Science and Technology, Online Counseling Resource… Let’s See Combinely……………….. © 2007, YCMOU. All Rights Reserved.18

19. School of Science and Technology, Online Counseling Resource… Branched Chain Fatty Acids  These are less abundant than straight chain fatty acids in animals & plant.  Examples are- Isovaleric acid Isobuteric acid © 2007, YCMOU. All Rights Reserved.19

20. School of Science and Technology, Online Counseling Resource… Essential Fatty Acids  The human body can produce all but two of the fatty acids it needs. These two, Linoleic acid (LA) and alpha-linolenic acid (LNA),  They are widely distributed in plant oils.  As they cannot be made in the body and must be supplied in food, they are called essential fatty acids.  They are polyunsaturated fatty acids and are the parent compounds of the omega-6 and omega-3 fatty acid series, respectively.  Human can easily make saturated fatty acids or monounsaturated fatty acids with a double bond at the omega-9 position, but do not have the enzymes necessary to introduce a double bond at the omega-3 or omega-6 position. © 2007, YCMOU. All Rights Reserved.20

21. School of Science and Technology, Online Counseling Resource… Functions of Essential Fatty Acids  In the body, essential fatty acids are primarily used to produce hormone-like substances that regulate blood pressure, blood clotting, blood lipid levels, the immune response, and the inflammation response to injury infection.  They are important in immune system and in blood pressure regulation, since they are used to make compounds such as prostaglandins.  The brain has increased amounts of linolenic and alpha-linoleic acid derivatives. Changes in the levels and balance of these fatty acid is associated with depression and behavioral change, including violence.  Fatty acids play an important role in the life and death of cardiac cells because they are essential fuels for mechanical and electrical activities of the heart. © 2007, YCMOU. All Rights Reserved.21

22. School of Science and Technology, Online Counseling Resource… Free Fatty Acids  Fatty acids can be bound or attached to other molecules, such as in triglycerides or phospholipids.  When they are not attached to other molecules, they are known as "free" fatty acids.  The uncombined fatty acids or free fatty acids may come from the breakdown of a triglyceride into its components (fatty acids and glycerol).  Free fatty acids are important source of fuel for many tissues since they can yield relatively large quantities of ATP.  Many cell types can use either glucose or fatty acids for this purpose.  In particular, heart and skeletal muscle prefer fatty acids.  The brain use glucose, or ketone bodies as fuel.  Ketone bodies are produced in the liver by fatty acid metabolism during starvation. © 2007, YCMOU. All Rights Reserved.22

23. School of Science and Technology, Online Counseling Resource… What we learn  Fatty acids are the carboxylic acids with hydrocarbon chain & amphipathic in nature.  ω & n are the two nomenclature systems of fatty acids.  There are 2 main types: straight chain & branched chain FA.  Straight chain is divided into Saturated & Unsaturated FA.  Saturated FA do not have double bond while unsaturated have it.  Cis is normally found FA in animals, plants & humans.  Branched chain FA are less.  Essential FA are those which are not synthesized in body.  Free FA derived from breakdown of triglycerides. © 2007, YCMOU. All Rights Reserved.23

24. School of Science and Technology, Online Counseling Resource… © 2007, YCMOU. All Rights Reserved.24 Critical Thinking Questions 1.Is the breakdown of unsaturated fatty acids is easier than saturated? Give reasons. 2.Why mammals lack the essential fatty acids?

25. School of Science and Technology, Online Counseling Resource… Hints To Critical Thinking Questions 1.Unsaturated fatty acids are kinked i.e. folded structure & saturated fatty acids are tightly packed straight chain. 2.Absence of enzyme which introduce double bond at omega-3 or omegs-6 position. © 2007, YCMOU. All Rights Reserved.25

26. School of Science and Technology, Online Counseling Resource… © 2007, YCMOU. All Rights Reserved.26 Study Tips  Book Title: Principles of Biochemistry Author: Robert Horton  Book Title: Biochemistry Author: Lubert Stryer

27. School of Science and Technology, Online Counseling Resource… © 2007, YCMOU. All Rights Reserved.27 Study Tips www.en.wikipedia.org Fatty Acids www.sieticpsychic.com Fats, oils, fatty acids-chemical structures www.biol.paisely.isu.edu Fatty acids

28. School of Science and Technology, Online Counseling Resource… Acknowledgements  www.biology.isu.edu www.biology.isu.edu  www.biology.clc.uc.edu www.biology.clc.uc.edu  www.phy.esu.edu www.phy.esu.edu © 2007, YCMOU. All Rights Reserved.28

29. End of the Presentation Thank You