CHAPTER 3 __ Lipid chemistry LEARNING TARGETS: Atthe end of the lesson, the students can: Characterize lipids and its importance In the human body. Differentiate the different classes of lipids. Identify and enumerate various types of fatty acids. G_ Mustrate the chemical formula of the different types of fatty acids and their role in the human body. What are LIPIDS? pids are a diverse class of nonpolar biological molecules used by organisms for longterm energy storage (fats, oils) and as elements of biological structures (phospholipids, cell membranes, waxes). Unlike carbohydrates and most other classes of compounds, lipids do not have a common structural feature that serves as the basis for defining such compounds. Instead, their characterization is based on their solubility characteristics. A lipid is an organic compound found in living organisms that is insoluble (or only sparingly soluble) in water but soluble in nonpolar organic solvents such as chloroform or acetone, Classified according to their chemical nature, lipids fall into two main groups. One group, which consists of open-chain compounds with polar head groups and long nonpolar tails, includes fatty acids, triacylglycerols, sphingolipids, phosphoacylglycerols, and glycolipids. The second major group consists of fused-ring compounds, the steroids, IMPORTANCE OF LIPIDS ‘As the methodology for the investigation of lipid metabolism developed, it soon became evident that fatty acids and their complex derivatives had at least two roles in the human body: 1, Asa source of energy. The oxidation of fatty acids was shown to be a major means of metabolic energy production, and it became clear that their storage in the form of triacylglycerol was more efficient and quantitatively more important than the storage of carbohydrates as glycogen. The physiologic caloric equivalent of 1 gam of fat when oxidized is 6kcal while similar amounts of carbohydrate only yield 4 kcal. 2, An essential component of cellular structure especially cell membranes. ‘As we have learned before, the plasma membrane is found to be largely composed of lipids and Proteins. These are several classes of membrane lipids - phospholipids, glycolipids, and cholesterol. The most abundant are the phospholipids, They possess one or more highly “polar” head groups in addition to their hydrocarbon tails. For this reason, they are often called polar lipids, 37t ' ; ctions of lipids, there are several other quan Lest ae ees of great functional significance. These include the ing asia! ea esol sane complex lipids for specific functions, such as maintenayr’ Sroka taney od beacon of non-polar substance in body fluids, In addition, severg Racteaes hormones, and prostaglandins, have highly potent are Important dietary oy at ean because of their high energy value but also because ofthe fat-soluble vitamins (a pn te and the essential fatty acids contained in the fat natural foods. Upids are also commercially, tf in the orm of soaps, detergents, greases and the various oils of the paint industry, Py ‘THREE GENERAL CHARACTERISTIC OF LIPIDS. The members ofthe lipids family have characteristic solubilities and properties in common 3 rather diverse in their chemical constitution. In general lipids are compounds having the fotos characteristics. 1. They are insoluble in water but soluble in one or more solvents of low polarity, 2. They are esters of fatty acids, 3. They are utilizable by the living organisms. These three characteristic features of the lipids also form a satisfactory definition of these class of substances, BIOLOGICAL IMPORTANCE OF LIPIDS 2 Fats provide a major way of storing chemical energy and carbon atoms in the body * Surround and insulate vital body organs * Provide protection from mechanical shock * Prevent the excessive loss of heatenergy CLASSIFICATION OF LIPIDS The following dassfication of lipids is modified from blood a Simple lipds- they are esters of fatty acids with various alcohols 1. Tilacylglyoerol (fats)-they are tester of fatty acids b. Compounds (complex) lipids- alcohol and a fatty acid. 1. Phospholipids lipids containing a fatty aid, sphingosine, and cay 2. Glucolipids (glycosphingolipids)- lipids ‘containing fatty acid sphingeyatate, 3+ Upoprotens= lipids attached to plasma proteins er otf Proteins, 4 arbohydrate, © Precursor and derived lipids - derivatives obtained By hydrolysis of those that stil possess the general physical characteristic of Mplds. They incuge ten” BFOUp A and B fatty aldehydes, ketone bodies, lipid soluble witamins, and hormones, tty acids, 38FATTY ACIDS Fatty acids are naturally occurring monocarboxylic acid, ‘They are considered as the structural components of all ipids (except cholesterol, bile salts, steroid hormones). They are, for the most part, both acyclic and unbranched. Fatty acids are short to long - chain organic acids having 4 to 24 carbon atoms; they have a single carboxyl group and a long, non-polar hydrocarbon “tall” which gives most lipids their water-insoluble and oil or greasy nature, 1. The number of carbon atoms in the molecule isin most cases even although odd-number carbon atom fatty acids are also found in nature, 2. They may be saturated or may contain one or more double bonds. General Considerations 1. Fatty acids are the most common component of most lipid structures, 2, Saturated fatty acids may be a short or long chain fatty acids. 3, Allnaturally occurring unsaturated fatty acids are long chain fatty acids 4, Unsaturated fatty acids only belong to the even number series of fatty acids. 5. In fatty acids containing two or more double bonds, the double bonds are never conjugated (- (OH-CH-CH-CH-CH) but are separated by a methylene group (-CH-CH-CH;CH=CH-), TYPES OF FATTY ACIDS «BASED ON CARBON CHAIN LENGTH a long-chain fatty acid (C-12 to C-26) b, medium-chain fatty acid ( C-8 and C-10) short-chain fatty acid (C-4 and C-6) + BASED ON CARBON-CARBON BONDS a saturated fatty acids (SFAs) b, monounsaturated fatty acids (MUFAs) ¢.polyunsaturated fatty acids (PUFAs) ‘A. SATURATED FATTY ACIDS (SFAs) Saturated fatty acids are fatty acids with a carbon chain in which all carbon-carbon bonds are single bonds, EXAMPLE: H ° / 4 H-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-C-OH / H IUPAC NAME: hexadecanoic acid Common Name: palmitic acid 39‘Alternative structural notations: ° “ © CH3-(CH2) 14-C-OH B. MONOUNSATURATED FATTY ACIDS (MUFAS) ‘These are fatty acids with a carbon chain in which one carbon-carbon double bond is present. EXAMPLE: H ° / a H-C-C-C-C-C-C-C-C-CeC-C-C-C-C-C-C-C-C-OH / H IUPAC NAME: cis-9-octadecenoic acid CN: oleic acid ‘Alternative structural notations: ° i © CH3~(CH2)7-CH=CH — (CH2)7— C-OHC. POLYUNSATURATED FATTY ACIDS ~ a fatty acid with « carbon chain In which two or more carbon- carbon double bonds are present, EXAMPLE 18 Carbon PUFA containing cls double bonds in the 9 and 12 positions IUPAC NAME: cls, cle -9, 12- octadecadienole acld CN: linolele acid Numbering and designation of carbon atoms 4, Garbon atom number 11s the carboxy! (COOH) carbon, 2, Carbon atom number 2 Is also called the alpha (A) carbon 3, Carbon atom number 31s also called the beta (8) carbon, 4 The methyl (-CHs) carbon which s the last carbon atom I also called the omega (w) carbon. SHORTHAND SYSTEM FOR SPECIFYING KEY. ‘STRUCTURAL PARAMETERS FOR FATTY ACIDS ‘Two numbers separated by a colon are used to specify the number of carbon atoms and the number of carbon-carbon double bonds present. Example: 18:0 ~denotes a C18 fatty acid with no double bonds 18:2 ~ denotes a C18 FA In which 2 double bonds are present. To specify double bond Positioning within the carbon chain of. unsaturated fatty acids, Greek capital letter delta ( _) folldved by one or more superscript numbers, . Example: (49, 12, 15) * Denotes a C18 PUFA with 3 double bonds at locations between carbons 9 and 10,12 and 13, and 15 and 16, ESSENTIAL FATTY ACIDS. The term “essential” means that the fatty acids must be supplied in the diet since they cannot be synthesized in our body. Linoleic acid, linolenic acid, and arachidonic acid are three essential fatty acids, Of these three, linoleic acid Is the only truly essential fatty acid, This is because linoleic acid our body can synthesize gamma-linolenic acid (C-18, Delta-6, 9, 12) and arachidonic acid, Deficiency of these essential fatty acids, as Induced In rates, caused reduced growth rates, Tcrluced deficiency, scaly skin, necrosis of the tall and lesions in the urinary system. The condition his not f a1of THEFATIY ACIDS sysTEM! systematic nomenclature is based on the ihe acids, the 1 ee mw ihe suffix-anoie: No pref the! _yo)= decanoie acid tn oe hhexadecanoic acid bd Palen! in the sa ‘acid, the systematic names contal ie pre scene be ac ad enol fr those wih two double bony "A sn sends weetranoic for those with four double bonds, He ba : : with three! ° i trienoic acid. _4g)= id, 9 octadecatrienoi 1 Oe 5:2} ds, cis-9, 12, -octadecadienic acid C18: eres 83 69,12-octadecatrienoic acid : ‘Arachidonic acid(20:4) 5,8,11,14-sicosatetranoic acid Cis-trans Isomerism in Unsaturated Fatty Acids anc NAMING geomet is it red fatty acids, depending -Atype of geometric isomerism occurs in unsaturat acids, depending onthe ae Soap around the axis of double bonds If the acy chains are on the same ides, tsg, ae act on opposite sides, trans- a5 in elaidic acid, the isomer of oleic acid. Natal rated fatty acids ae near all he cis configuration. The cis double bond introduces igi the hydrocarbon tail of the fatty acids. Physical Properties of Fatty Acids A. General considerations regarding saturated fatty acids 1 The longer the hydrocarbon chain, the more insoluble in water and the lesser the sok solvents. 2. Short-chain fatty acids are volatile fatty acids. 3. As the number of carbon atoms increases, the melting point becomes higher. 4 As the melting point increase with the number of carbon atoms, the fatty acid becomes m= solid at room temperature. | B Sater considerations regarding unsaturated fatty acids, cradiinel th prjenee ‘of double bonds will produce the following results. ids become more soluble in solvents i : me i raichacrorn Ivents of low polarity . The fatty acids become li iquid at room temperature. 4 The boiling point becomes lower, eo a2“2 Chemical Reactions of the Fatty Acids. 1. Formation of soaps ‘The generic name “soaps” has been given to any salt of long-chain fatty acids Two kinds of soaps 1. Soluble soap- they are the sodium and potassium soaps. ‘The potassium soap is more soluble in water than the sodium soap, and in accordance with already mentioned, the soap of unsaturated fatty acids are more soluble in water than are those of saturated fatty acids, 2, Insoluble soap- they are the calcium and magnesium soaps. b. Formation of esters ‘The most prominent reaction of the carboxyl group of the fatty acids is etherification with alcohol to ‘one molecule of ester and water. The reaction between the trihydroxy alcohols, glycerol, with three fatty acid residues to form triglyceride is a classic example of this reaction in vivo. . Reactions of the double bonds (unsaturated fatty acid) 1, Hydrogenation- the double bonds in unsaturated fatty acids capable of adding hydrogen. This is an important reaction utilized in the industry because it permits the transformation of inexpensive polyunsaturated vegetable oils into shortenings. tis also a means of converting an unsaturated acid to its saturated fatty acid. 2. Halogenations- ethylenic bonds, under mild conditions, readily react with halogens. Very often jodine is used as the halogenating agent. EXAMPLE: -CH-CH=CH-CHyla-)-CHr-CH-CH-Ha From this reaction, itis obvious that the amount iodine taken up by a given fat may be measured quanttively by using a known amount of fat and determining the excess halogen by conventional idometric procedures. lodine number, therefore which is the amount of iodine absorbed by 100 grams of fat, is a useful index of the degree of unsaturation ofthe fatty acids composing a given fat. This occurs slowly and spontaneously in the presence of air and contributes to the process termed rancidification, A rancid fat not only has an off-taste and disagreeable door but in addition, contains a {roup of the peroxide type whichis quite destructive to the fat-soluble vitamins and other essential dietary substances. 4, Oxidation- whereas the saturated fatty acids are relatively insusceptible to oxidation, unsaturated fatty acids can be oxidized. This occurs slowly and spontaneously in the presence of air and contributes to the process termed rancidification. A rancid fat only has on off-taste and disagreeable odor, but in addition, a certain group of the rencidification involves attack at the double bonds by peroxide radicals, with the formation of Unstable hydroperoxides that decompose to Keto acd and hydroxy! keto acids, Oxidation of double proceeds much more rapidly in the presence of ozone, On. 43YCEROL fat. Triglycerides gp TRIACYLGL fide, neutral fat or fat. © 16 ony Iyceride, is ako called in the form of bali ratte eet of, ety {rata ocuring PK. So isto serve as the chet storage from fy “ of ain ats. Their Mm: tin the omer types of animal eal in pure form and in an almost unlimited amount pose te i ‘body. They are st ‘val rot normally found in membranes. h three molecules of fatty Atids, ter of glycerol wit le Tran csine contains no electical charged or high polar uncon” hydrophobic: ou CLASSIFICATION AND NOMENCLATURE is lows: The type ra fora tagcat as fellows (method for designating the atoms of glycerol) HiC-O-CO-R 1 Alpha R,OCO-CH 2 fee HrCOCOR 3 Alpha i all be the same. Usually, Rt an a, R2, and R3 represent fatty acid chains that may oF may not al be ual, ad fatty sar Saturated and R2are unsaturated fatty acid. The numbering system, which indicates te ‘ac Peston ofthe fatty acids inthe glycerol molecule, has largely superseded the ‘Older ad ‘nomendature, Types of Triacylglycerol 4 According to the number of carbon atoms of the fa 1. Trigycerides of short-c tty acids esterified to glycerol hain fatty acids- the atoms, fatty acids esterified have two to four ate Medium-chain length trighycerides- the fatty acids esterified have six to:12 carbon atoms. Triglycerides of long-chain fatty acids- the fatty acids esterified have more than 12 carter ‘atoms, pe kinds of fatty acids este ride: contains only a single kind ids contain, rifled to glycerol Of fatty acid in all three Positions; they are tienen accel CoS 2 oF 3 ferent Totty acids; the number of ths type of Mt the re posse 3 dierent fatty acids tached to carbon-2 atoms 's asymmetric and therefore 62 eo} med D and L. Most : I configuration, " "atural fas including the phosphogleeries M*Physical Properties of Triacylglycerol The general properties of fats are reminiscent of those of fatty acids. Triaoylehpcarihe erick mi the solid of liquid form at room temperature depending on the nature «A the constituent tatty acide, The incorporation into triglycerides of short-chain fatty acids and unnaturated fatty acide reudts wn (ats with Jow melting point and therefore liquid at room temperature and are termed olls. On the other hand incorporation of long-chain saturated fatty acid produces trigyerides which are vernischid whi at room temperature since they possess high melting points, The latter is usually called fats, Chemical Properties of Triacylglycerol 1. Ordinary hydrolysis and saponification Triacylglycerol undergoes hydrolysis when boiled with acids or when acted upon enzymatically by the enzyme lipase. The reaction yields three molecules of fatty acids and one giycerol mokecitle, the fatty acids being insoluble in water. Hydrolysis with an alkali such as NaOH or KOH yields a mixture of fatty adid soaps and gycerck, tis process is known as saponification (soap formation). This gives rise to an operational dassification in lipid analysis which defines that part of the total which is soluble in water but insoluble in ether after treatment with hot alkali as the saponifiable fraction. Neutral fats and fatty acids are an example of saponifiable materials; non-saponifiable substances include high molecular weight alcohols, ketones, hydrocarbons, and steroids. 2. Saponification number Itis an analytical procedure that is used to determine the average length of the carbon chain of the fatty acids in a given fat or oil. It is inversely proportional to the molecular weight of given fat oll. its inversely proportional to the molecular weight of a given fatty or oil. This is the number of milligrams of KOH required to saponify 1 gram of fat or oil. Triglycerides of short-chain fatty acids (e.g, tributyrin) will have a lower molecular weight but a higher saponification number compared to triglycerides of long-chain fatty acids which will have 2 lower saponification number. Tripalmitin is an example of such triglycerides of long-chain fatty acids. 3, Hydrogenation The hydrogenation of oils such as cottonseed to prepare commercial cooking fats and margarine is an important food in the industry. In the process, the glycerides are only partially saturated to form a ‘sort fat. This is a reaction of fats due to the presence of double bonds. 4. Autoxidation Another reaction of fats due to unsaturations given the appropriate conditions of moisture, light ‘warmth, oxygen and possibly catalytic substances, fats containing unsaturated fatty acids undergo a ‘eaction known as autoxidation. This is probably a major factor in the complex of changes in fats called rancidification, 45pHosPHOLIPIOS The are a heterogeneous grey, are classified together partially on the felt e pertialy on the basis of the ester ph oF sone compounds. They are present in all cetts, one Prseas and are the second most abundant naturatly Meare a the phospholipids are composed of fatty ach, 4 Ny x phosphoric acid and either Preerol (ph J Fphingosine (sphingomyelin) hos oho ean ee ‘nese compounds can be separated into varegy S ~~ depending upon the structural components present o Sg | cnatecule. The following classification is an example on im rm, 3. Upositol- phosphatidylinositol 4. Phosphatidyighycerol ’ 5. Cardiolipin- diphosphatidyl glycerol b Plasmalogen Py o 1. Phosphosphigesides or Sphingomyelins Functions of sesce serve a5 structural components of membranes of the cell surface and subceie organelles. 2. They also playa role in activating certain enzymes 3. Asa surfactant, preventing the collapse of the lungs at the end of the expiratory phases respiration. This is @ specific function of a special type of lecithin called dipalmitoy lectha. 4. The detergent properties of the phospholipids play an important role in bile pigment wher they function to solubilize cholesterol, thus preventing the formation of cholesterol and bt pigment gallstones. 5, Phospholipids are integral components of plas solubilization of cholesterol, cholesterol esters, an low-density lipoprotein) and LDL(low-density lipoprotein). 6. The fatty acids that comprise phospholipids can be transferred to various ‘compounds, as cholesterol thus converting the latter to cholesterol ester. ma lipoproteins and act to faciitas ' od triglycerides in chylomicrons, Vit = PHOSPHOGLYCERIDES (GLYCEROPHOSPHATIDES) Ter ior phospholipids found in ment They are the most common phospholipids and the maj ted alcohol. consist of a glycerol backbone, two fatty acids chain: , , and phosphoryla the parent compound of all phosphoglycerides. can eetAF “ ee Se EZ. ov. Some important glycerophosphatides 1. Lecithin (phosphatidyl) Itis the most abundant i jecthin ib a'Ver) etective $a ied lier in plants and animals, Specific lecithin called dipalmitoyl surface of the lungs. ng adherence, due to the surface tension of the inner 2. Cephalin (phosphatidylethanolamines) It contains more of the long-chain unsaturat positions. These phospholipids are involved in bl of thromboplastin. ted fatty acids, especially arachidonic acid, at the C-2 lood coagulation because it is an important component 3. Upositol (phosphatidylinositol) cell, it pe eoc ey agra as ie Phosphorylated derivates producing monophosphoinositide, di-and m pt ee ery often it contains almost exclusively stearic acid in the C-1 position and arachidonic acid in C-2. It appears that phosphoinositides play an important role in the metabolism of nervous tissues since studies with radioactive phosphate have demonstrated a high exchange rate of the phosphorous esterified to the inositol. A possible role of these inositol derivatives is to control calcium ion movements across cell membranes, 4, Phosphatidylglycerol In this glycerophosphate, the head is often found in the bacterial membrane as an amino derivative of L-lysine, It occurs in relatively large amounts in mitochondrial membranes and is a precursor of cardiolipin. 5. Cardlolipin It is also called diphosphatidy! glycerol, the backbone of 3 molecules of glycerol joined by two phosphodiester bridges. It is characteristically abundant in cell membranes of bacteria. It is also present in large amounts in the inner mitochondrial membrane where it nerves to attach cytochrome of the electron transport chain. It is the only phosphatide with the known immunological property. PLASMALOGENS This is a class of phosphatides in which the fatty acid at C-1 is replaced by Alpha and Beta- unsaturated alcohol in ester (alkenyl) linkage. The principal types of plasmalogens are phosphatidyl {instead of the suffix-dyl for glycerophosphatides) choline and ethanolamine. They constitute as much ‘as 10% of the phospholipids of brain and muscle. They are also found appreciable amounts in red blood cells. It is noteworthy that they are not found in significant quantity in non-animal tissues. SPHINGOLIPIDS - They are complex lipids containing sphingosine as their backbone and ceramide as the present gosine attached to a fatty acid. They are found in large compound. Ceramide is made up of sphin 3 quantities in brain and nerve tissues. They are the second largest important membrane components in both plant and animal cells. Three building block components of sphingolipids 1. One molecule of fatty acid 2. One molecule of sphingosine 3. Apolar head group which may be:in case of sphingomyelin saan 2 Resection ch 2 cere and ganglioside cartohy abundant sphingolipid in the ssuesif higher animals. They are founy They ae the on haus tue. The fatty as found in nervous issue are al SEE ys dase a ings pln oe ad ne 2 eo sara inthe rn es, and spleen of persons with Niemann dene” (GLYCOUPIDS) - a eo Seed egies are ako knowns holo scoping cs Since they ae or moce sugar molecules (as polar head group) atach by @ beta-sivosiic linkage t the et group at C1 sphingosine. Functions of gyeosphingolipids 1L. As constituents of cell membranes. 2. They function in the transmission of a nerve impulse across synapses. 3. They are believed to be present at receptor sites for acetylcholine and othe neurotransmitters. 4. They plan an informal role in cell-cell interactions by providing specific recogitn determinants on the surface of cells. 5. Some ofthe neutral glycesphingolipids are found on the surface of red blood cells and gh them blood. group specificity, CEREBROSIDES ‘The polar head group of this glycosphingolipid is @ monosaccharide bound in beta-ghycosie linkage to the hydroxyl group of the sphingosine molecule in ceramide. There are two types d cerebrosides depending on the sugar present: 1. Galactocerebroside Contains D-galactose; Present in the brain and nervous system. It accumulates in the white matt of the brain in persons with Krabbe’s disease. 2. Glucocerebroside Contains D-glucose; found in non-neutral ti i | i t J issues b. ind liver ot Persons with Gaucher's disease, of animals, It accumulates in the spleen ar mer pont oft ceeds ‘esulting inthe removal of faty acid residue leaves a sphingos® Acid fraction, RONG Real that ceramide, the parent compound, is a sphingosie 381 48** GANGLIOSIDES ‘These are molecules composed of a glycosphingolipid (ceramide and oligosaccharide) with one or more sialic acids. This most complex glycosphingolipid contains very large polar heads made up of several sugar units such as: 1. One or more terminal sugars units of sialic acid (N-acetyineuraminic acid) 2. One of more hexoses such as glucose-galactose 3. Atleast one mole of either N-acetylglucosamine or acetylgalactosamine They are highly concentrated in the ganglion cells of the central nervous system, where they make up about 6% of the membrane lipids in the gray matter of the brain. There is an accumulation of gangliosides in persons with Tay-Sachs disease. ‘A specific ganglioside in intestinal mucosal cells mediates the action of cholera toxin. They are also thought to be receptors for other toxic agents, such as tetanus toxin, and a certain virus, such influence virus. STEROIDS The steroid is a biologically active organic compound with four rings arranged in a specific molecular configuration. Steroids have two principal biological functions: as important components of cell membranes which alter membrane fluidity; and as signaling molecules. Certain features in the formula that are shared in common by most membranes of this class of substances include the following: 1. The presence of an oxygenated or hydroxylated substituent IMoleciia atractare Of hare onC-3 2. The presence of “angular” methyl groups on C-10 and C-13 to constitute C-18 and C-19 of the ring. 3. The presence of an aliphatic side chain on C-17. This serves as a convenient basis for classifying steroids into the following: a, Sterols- have from 18-10 carbons in the R-group (C-27, C-28, and C-29 steroids.) . Bile acid. have 5 carbons in the side chain and they terminate in a carboxyl (OOH) radial (C- 24 steroids) c. Progesterone and adrenal cortical hormones- have 2 carbons in the side chain (c-21 steroids) 4d. Naturally occurring sex hormones have no side chain on C-17 CHOLESTEROL Rt the most abundant and the most important sterol animal tissues, the structure of free cholesterol is shown below: c mn WALA my, cn, ony ae CHOLESTEROL 49The hydroxy! group at C-3 readily forms esters with unsaturated fatty Aids ths cholesterol ester. The double bond at the cs and C-6 Position is the basis of iat techniques for its quantitative determination because it leads itself readily to addition "2s as Liebermanr-Burchard reaction. It crystallizes in colorles, transparent plates ms characteristics notch on the edge. The actual concentration of cholesterol in the piss ie people is usually 150-200 mg/100mi. it is synthesized mainly in the liver, ad: h renals, cholesterol has been implicated in atherosclerosis, Reduction of the double bong Omran coprostanol, the major fecal sterol. Functions of Cholesterol 1. Itisa component of virtually all cell surfaces and intracellular membranes 2. Itis a precursor of bile acids that are synthesized in the liver 3._Itis the precursor of various steroids hormones such as progesterone, Cortisol, tests etc. 4. Itis the precursor of vitamin B3 or cholecalciferol 5. As cholesterol ester, it serves as a special transport agent for unsaturated fatty acids, BILE ACIDS (C-24 STEROIDS) Bile acids are steroids havin, 1g 5 carbon atoms in the side chain Four such acids have been isol: and terminate in a carbary! gap. f acid and glycochenodeoxycholic acid or taurochenodeoxycholic acid sodium salts of these conjugated bile acids are water soluble and are powerful detergents af emulsifying agents that are great value i in the digestion and absorption of lipids in the gut.