Note takingSelinger, B. (1998) Chemistry in the Marketplace- 5th Edition.

New South Wales: Harcourt Brace and Company, Australia. y y y y y y Fats oils and some waxes are all natural esters. They are long, straight chains of carboxylic acids. An ester is created when an organic acid combines with an alcohol. The difference between fats and oils is the melting points. Fats are solid at room temperature and oils are liquids. Glycerol is common to all fats. When this alcohol is combined, glycerine is the by-product (used in the manufacture of soap from fat). The fatty acid is of interest as difference occurs depending on the nature of the acid groups: the length of the chain (molar mass), the number and position of double bonds (unsaturation). There are three important groups: saturated fatty acids, straight-chain unsaturated fatty acids, and the polyunsaturated fatty acid. Saturated fatty acids have the general formula CH3(CH2)nCOOH where n is even and varies from 2 to 24. Odd numbered acids only occur in traces, generally in ruminants (regurgitated undigested foods). Unsaturated acids have 18 carbon atoms, usually with one double bond in the middle of the chain. If other bonds are present, they lie closer to the carboxyl group, COOH. Double bonds cannot be rotated, and there are two possible geometries which are called cis and trans .

y y y y y

Cis

Trans

Source: http://www.molekult.no/euro/science_corner/carbon.html y Oleic acid is a component of olive oil and is most abundant of all fatty acids: CH3(CH2)7CH y y CH(CH2 )7COOH

Vast majority of olefinic (unsaturated) linkage in fats and oils are of the cis type. Polyunsaturated fatty acids have more than one cis-methylene interrupted double bond. The general formulae is:

CH3(CH2)x(CH y y y y y y y

CHCH2 )

(CH2)z COOH

X and z range between 3 and 20 and ranges from 1 to 4. The double bond when of the cis type means that the molecules do not pack together easily. Hence the low melting point of oils. Substances with shorter chains also melt at lower temperatures. Natural fats consist of the molecule of glycerol attached to three fatty acids. Olestra is a calorie-free fat replacement. The glycerol in natural fat is exchange for sucrose, which attaches six, seven or eight fatty acids. This molecule is the first fat substitute that does not break down during cooking or in the gut (hence the side effects of cramping, bloating and diarrhoea and even anal leakage). Olestra can remove oil-soluble vitamins and carotenoids from the body.

Wilbraham, A. et al. (2002) Chemistry. New Jersey: Prentice-Hall, Inc. y y y y y Fats, oils and other water-insoluble compounds are called lipids. Lipids tend to dissolve readily in organic solvents such as ether and chloroform, rather than highly polar solvents such as water. Natural triglycerides are fats and oils that are triesters of glycerol with fatty acids, which are long-chain carboxylic acids. (C12 through to C24). In organic chemistry, fats and oils are both esters that are easily hydrolysed in the presence of acids and bases. Hydrolysis of oils or fats by boiling with an aqueous solution of an alkali- metal hydroxide is called saponification (used to make soap).

http://www.biologyreference.com/La-Ma/Lipids.html

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The Olestra molecule is made up of six to eight fatty acid groups connected to a sucrose base. A normal fat molecule, in contrast, is a triglyceride, which is an organic compound made up of three fatty acids groups attached to a glycerol base. Digestive enzymes usually bind to fat molecules and act as catalysts in the hydrolysis of the bonds between glycerol and fatty acids. These enzymes are unable to bind to Olestra molecules.

Fennema, O.R. (1996) Food Chemistry. New York: Marcel Dekker, Inc. y y y Sucrose polyester is a type of carbohydrate fatty acid polyester. It is lipophilic, nondigestible, nonabsorbable fat-like molecules with physical and chemical properties of conventional fats. Esterification of sucrose with long-chain fatty acids obtained from vegetable fats.

Clark, J. (2003) Esterification.UK: Chemguide.co. Accessed 13th October 2011, <http://www.chemguide.co.uk/organicprops/alcohols/esterification.html> y y y Esterification is the reaction between alcohols and carboxylic acids to make esters, acid chlorides (acyl chlorides) and alcohols, and acid anhydrides and alcohols. A carboxylic acid contains a COOH group. An ester is created when the hydrogen in this group is replaced by a hydrocarbon group of some kind (an alkyl or aryl group).

Fat Replacers . (1998) Scientific Status Summary. Vol. 52, No. 3. Illinois: The Institute of Food Technologists. y y y y y y y y Sucrose fatty polyesters are mixtures of sucrose esters formed by chemical transesterification or interesterification of sucrose with six to eight fatty acids. Transesterification is the exchange of an acyl group between an ester and an acid, alcohol or amine. Interesterification is the exchange of an acyl group between two esters. Sucrose polyester is manufactured from saturated and unsaturated fatty acids of chain length C12 and higher. The first step is hydrolysing and methylating fatty acids to form fatty acid methyl esters. Hydrolysis is the breakdown of an organic compound due to reaction with water. Methylation is when the hydrogen of the hydroxyl group of methyl alcohol is replaced with by a metal. For vegetable oils, the crude Olestra product is purified by washing, bleaching, and deodorizing to remove free fatty acids and odours. This is followed by distillation to remove unreacted fatty acids methyl esters and sucrose esters with low degrees of fatty acid substitution. These esters are added to sucrose octaacetate for ester interchange using catalysts, such as alkali metals or alkali metals or their soaps.

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y y y y

Olestra is non-caloric because the large size and number of the non-polar fatty acid constituents prevent olestra from being hydrolysed by digestive lipases. The concentration of vitamins A, D, E, and K required for supplementation in olestracontaining foods are 0.34 X RDA for Vitamin A/ 10g Olestra, 0.3 X RDA for vitamin D/ 10g Olestra, 0.94 X RDA for vitamin E/10g Olestra, and 1.0 X RDA for vitamin K/10g Olestra. Supplementation of vitamin A compensates for Olestra s effect on the decreased absorption of lipophilic carotenoids. Olestra does not significantly affect the absorption of other macronutrients such as carbohydrates, proteins, or water-soluble vitamins and minerals. Olestra can benefit people at a high risk of coronary heart disease, obese individuals and colon cancer patients. Sucrose fatty acid esters are different to sucrose polyester. They are mono-, di-, and triesters of sucrose with fatty acids.

Source: AS ABOVE Clark, J. (2004) Hydrolysing Esters. UK: Chemguide.co. Accessed 13th October, 2011, <http://www.chemguide.co.uk/organicprops/esters/hydrolysis.html> y y y Hydrolysing esters involves splitting them into carboxylic acids (or their salts) and alcohols by the action of water, dilute acid or dilute alkali. Saponification involves hydrolysing complicated esters to make soap using alkaline hydrolysis. When large esters are heated with sodium hydroxide solution, a salt of carboxylic acid is formed and also an alcohol.

Purves, K. et al. (2004) The Digestion and Absorption of Fats. USA: W.H. Freeman & Co. Viewed 13th October 2011, <http://bcs.whfreeman.com/thelifewire/content/chp50/5002001.html> y y Digestion is the breakdown of complex food molecules into smaller components that can be absorbed and utilized by cells. The enzyme amylase breaks down starches as food is chewed.

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When food reaches the stomach, the enzyme pepsin and hydrochloric acid creates a strong acidic environment and thus begins the process of protein digestion. Low pH helps to dissolve the intercellular structures that bind the ingested tissues together. Bile salts from the liver and specialized enzymes from the pancreas play critical roles in the digestion of fat beginning in the small intestine.

Rattagool, K. (1999) Scientific considerations of Olestra as a fat Substitute. Texas: University of North Texas. y y y y y y Because Olestra is made of long-chain fatty acids, its physical properties are like those of natural fats and, like fats, it can be heated without altering its chemical structure. Olestra is a large, bulky lipid and is not hydrolysed by intestinal lipases. It does not enter the mixed micellar phase in the intestinal lumen. Sucrose polyester resists digestion by pancreatic lipase (an important fat digestion for the hydrolysis of ester bonds). Olestra consists of a sucrose molecule and a mixture of fatty acid molecules which is each made up of more than twelve carbon atoms. Olestra is a much bulkier molecule than most fats and, therefore, not a suitable substrate for lipid-degrading enzymes.

Source: AS ABOVE y y y y y y A class of sucrose polyesters which form a chemically heterogeneous (different states) group of complex substances made of sucrose and several esterified fatty acids. The prefix ol represents olein and estra , ester. Ester describes the chemical bond between an acid and an alcohol. Olestra is the mixture of hexa-, hepta-, and octa- fatty acid esters of sucrose. The long-chain fatty acids can be saturated or unsaturated. Mixing molten sucrose and long chain fatty acid methyl esters at temperatures between 170-187 in the presence of soaps of lithium, sodium, or potassium as catalysts.

Source: AS ABOVE y y y y y y y y y y Olestra is non-polar, lipophilic and insoluble in water at 5 to 42 mg/L. It is very soluble in many organic solvents and oils with the octanol. The behavior of olestra is related to its polymorphic form of alpha like and beta like phases of olestra. Fat absorption begins with the dissolving of the fat molecule in the cell membrane by a chemical that is complementary with the target molecule. The fat is held by the cell membrane or transported into the inside of the cell. Hydrolytic or saponification reaction occurs and cleaves (splits) the fatty acids from the alcohol part of the sugar moiety (part). Or, in some cells producing exoenzymes, the free fatty acids enter the cells by reacting with the cell membrane and Hydrolysis of fats in the human body is brought about by enzymes produced in the pancreas. Fecal bacteria from the intestinal tracts of human beings failed to metabolize olestra. Normally, fat leaves the stomach more slowly than fluids such as water or milk due to its lower density and greater viscosity but olestra leaves the stomach at approximately the same rate as water.

Fackelmann, K. (1996) Science News - Olestra: too good to be true; researchers flush out health risks of fake fat. USA: Gale Science in Context Web. Accessed 10 Oct 2011, <http://ic.galegroup.com/ic/scic/MagazinesDetailsPage/MagazinesDetailsWindow?displayGroupNa me=Magazines&disableHighlighting=false&prodId=SCIC&action=e&windowstate=normal&catId=&d ocumentId=GALE%7CA17907683&mode=view&userGroupName=uq_splc&jsid=0865bb0703841ccf1 0ef6c217988b35b> y y Olestra is a synthetic mixture of sugar and vegetable oil. It is not digested or absorbed.

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Olestra may bind and flush away key nutrients in the body that prevent disease. Olestra carries away vitamins A, D, E, and K. It also sweeps out carotenoids: the yellow, orange and red pigments in fruit and vegetables. People who ate just three small olestra- containing snacks per week could expect at least a 10 percent drop in concentrations of carotenoids in their blood.

Sucrose Polyester. Chemical Compounds (2006). Detroit: Schlager, N. et al. Accessed 10 Oct 2011, <http://ic.galegroup.com/ic/scic/ReferenceDetailsPage/ReferenceDetailsWindow?displayGroupName=Reference&disa bleHighlighting=false&prodId=SCIC&action=e&windowstate=normal&catId=&documentId=GALE%7CCX2830700098& mode=view&userGroupName=uq_splc&jsid=acda7c8fba5ec34b96f0977b6f5db781> y The molecules in Olestra are very similar to those of real fat. In fact, they are made from fat. But Olestra molecules are too large for the human body to break down into smaller chemicals that can pass into the blood and be used by cells. The chemicals that the human body uses to digest fat molecules in ordinary food simply do not work on Olestra. Olestra passes right through the body and is excreted without being chemically changed. Since it is not digested, it cannot add to a person's weight.Other fat substitutes are digested, but do not have as many calories as fat.

y y y

Corcoran, L and Jacobson, M. (1998) Olestra. Washington D.C: Nutrition Action Healthletter. Accessed 10 October 2011, <http://ic.galegroup.com/ic/scic/NewsDetailsPage/NewsDetailsWindow?displayGroupName=News &disableHighlighting=false&prodId=SCIC&action=e&windowstate=normal&catId=&documentId=GAL E%7CA20382076&mode=view&userGroupName=uq_splc&jsid=695c5f40ddbd1e370b70d0c365f03a d6> y In two 1993 P&G studies, 39 people who ate eight grams a day of olestra-the equivalent of 16 chips with meals for eight weeks had a 50 percent drop in their total blood carotenoids.(2,3)

Timberlake, K. and Timberlake, W. (2008) Basic Chemistry. New Jersey: Pearson Education, Inc. y y y y y y y y y y y Lipids are a family of biomolecules that have the common property of being soluble in organic solvents but not very soluble in water. Lipids such as fats and oils are esters of glycerol and fatty acids. Steroids are characterized by the steroid nucleus of four fused carbon rings. Fatty acids contain a long carbon chain with a carboxylic acid group at one end. Saturated fatty acids contain only single bonds between carbons. Monounsaturated fatty acids have one double bond in the carbon chain, Polyunsaturated fatty acids have two or more double bonds. Compounds with double bonds have two structures: cis and Trans isomers. Cis isomers have groups attached on the same side of the double bond. Trans isomers have groups attached on the opposite sides of the double bond (Refer to figure 1). Cis structure of oleic acid does not have a linear order of atoms, but trans-oleic acid does.

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In double bonds of unsaturated natural fatty acids the double bonds are the cis isomers. Fats and oils are known as triacylglycerols. These substances are also called triglycerides, and are triesters of glycerol (a trihydroxy alcohol) and fatty acids. A triacylglycerols is produced by esterification, a reaction in which the hydroxyl groups of glycerol form ester bonds with the carboxyl groups of fatty acids. A fat is a triacylglycerol that is solid at room temperature. Oil is a triacylglycerol that is usually liquid at room temperature. The fatty acids to manufacture Olestra are often taken from the fats in cottonseed or soybean oil. Olestra is a large molecule which cannot be absorbed through the intestinal walls. Enzymes and bacteria are not able to break down the molecule. The large molecule of olestra combines with fat-soluble vitamins A, D, E, K and carotenoids. Carotenoids are plant pigments from fruits and vegetables that prevent disease. Point: Since there are already low-fat snacks on the market, it remains to be seen whether olestra will have any significant effect on reducing the problem of obesity. Saturated fatty acids have higher melting points than unsaturated fatty acids because they pack together more tightly. FAT + OIL GLYCEROL + SALTS OF FATTY ACIDS (SOAPS)

Glauiusz, J. (2001) Discover Magazine: The Chemistry of Fat Substitutes. New York: Kalmbach Publishing Co. Accessed 16th October 2011, <http://discovermagazine.com/2001/mar/featchemistry> y y A study funded by Procter and Gamble indicate that people who eat Olestra can reduce their cholesterol levels by more than 10 percent. Also, there is a 10 percent increase in blood flow to the heart among those who had eaten an olestra filled banana muffin.

Zamora, A. (2011) Fats, Oils, Fatty Acids, Triglycerides. USA: Umbrella Technologies, Inc. Accessed 16th October 2011, <http://www.scientificpsychic.com/fitness/fattyacids1.html> y y y y Triglycerides have lower densities than water. When glucose is combined with one fatty acid it is a monoglyceride, when it is combined with two: diglyceride and when combined with three: triglyceride. Esters are compounds created by the reaction between acids and alcohols that release water as a by-product. Olestra acts as a lipid, therefore causes depletion of fat-soluble vitamins.