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The Science behind the Use of Fully Hydrogenated/Saturated Fats in Place of Partially Hydrogenated Fats Emily Rose Greco, B.S. March 14, 2013

Introduction When one looks at a nutrition label and sees the words Total Fat, there is a lot more behind this broad, all-inclusive term than one might think. Chemically speaking, unsaturated fats are fats that are typically liquid at room temperature and contain at least one carbon to carbon double bond, not completely saturated with hydrogen.4 On the nutrition label there are two unsaturated fats listed: monounsaturated and polyunsaturated. Monounsaturated indicates that there is only one double bond in the molecule, while polyunsaturated means that there is more than one double bond present in the molecule. In contrast, saturated fats are generally solid at room temperature and contain only carbon to carbon single bonds that are completely saturated with hydrogen. In other words, every bond that is not carbon to carbon, is a carbon to hydrogen bond.4(p51) Trans fats are unsaturated fats originally in the cis (carbons of the parent chain are on the same side of the double bond) formation, that undergo isomerization, and convert to the trans formation (carbons of the parent chain on opposite sides of the double bond). This conversion makes the molecule more stable.3,4(p51) Whereas animal fats are rich in saturated fats, plant oils such as corn and soybean oil are rich in unsaturated fats. Plant oils are the substances manipulated by hydrogenation in order to use them in processed foods to provide a desirable firmness, along with a moist texture and pleasurable taste.4(p211) Hydrogenation is the process of adding hydrogen to unsaturated fatty acids in order to alter their chemical structure; during which substances with higher melting points are created. This process saturates the molecule either partially or completely, thus creating partially hydrogenated fats or fully hydrogenated fats. This is an important part of the manufacturing process for a wide array of fat-containing products to increase shelf life.3(p240)

It is essential to bring attention to this topic because of the recent light shed on the horror of trans fats found in partially hydrogenated oils. The history and discovery, chemical structure and physical properties of trans fats, health-related problems, Food and Drug Administration (FDA) labeling requirements, food sources, alternatives, controversies, and how this research applies to dietetic practice will be discussed. The purpose of this research is to inform the reader about how the process of hydrogenating oils creates trans fats in many of the foods commonly consumed everywhere, and what one can do to avoid or reduce consuming these cardiovascular disease-causing fats. History/Discovery In 1903, German chemist Wilhelm Normann developed the method for hydrogenating edible oils based off of the work done by French chemist Paul Sabatier.2 Joseph Crosfield & Sons acquired the rights to Normanns patent and began to campaign to try to capture the attention of European soap manufacturers in this particular technology. In 1907, Crosfield & Sons brought their hydrogenation technology to the United States. One of the Crosfield chemists, Edwin Kayser, contacted John Burchenal, a business manager of Procter & Gamble, and in 1908 a business arrangement was agreed upon, and two U.S. patent applications were filed. The patents were granted and hardened oils were produced for the purpose of soap-making. Then in 1910, Burchenal filed two more U.S. patent applications, this time pertaining to food products. The patents were granted and hydrogenation of cottonseed oil began. This was the beginning of what many know as Crisco.12 It was very common in that era to cook with lard or butter; Procter & Gamble advertised that Crisco was a healthy alternative and more economical because it was made with vegetable oil (taking advantage of the word vegetable implying healthy).

Chemical and Physical Properties The hydrogenation of fats (oils) results in the reduction of the double bonds in unsaturated fats to single saturated bonds, by the means of using hydrogen gas in the presence of a metal catalyst, which is usually nickel.2(p868),4(p211) This food processing technique is the culprit in the production of trans fatty acids. Cis double bonds in unsaturated fats form a bend in the chain that prevents unsaturated fatty acids from packing as compactly as saturated fatty acids, resulting in a lower melting point (usually liquid at room temperature) than a saturated fatty acid with the same molecular weight. However, in the case of trans unsaturated fatty acids, they are practically straight and resemble saturated fats in both structure and high melting points.2(p869) Oils that are fully hydrogenated do not contain double bonds and therefore do not contain trans fat. These oils can be manipulated to acquire the favorable characteristics by blending an oil that has not been hydrogenated.3(p255) Food Sources (Processed and Naturally occurring) Foods containing partially hydrogenated fats and, in turn, trans fats include foods baked using margarine and vegetable shortening, prepared foods such as pre-fried French fries, taco shells and doughnuts, hamburger buns, pizza dough, crackers, cookies, pies, pre-mixed products such as pancake and hot chocolate mix, crme-filled cookies, potato and corn chips, frozen breakfast foods, and shortenings used for deep frying.3(p257),4(p211) Hydrogenation is also responsible for altering peanut butter from its original state which would otherwise be a concentrated solid mass with a layer of oil on top to a homogenous spread with an extended shelf life.3(p257) Stick margarines are higher in trans fats than tub or liquid margarines because more hydrogenation is required to produce the rigidity of the stick; todays levels, however, are about 25% lower than in the past.

Some trans fats are naturally occurring (via bacteria in the gut of ruminants) and are found in some animal-based foods such as meat and dairy products. These trans fats make up approximately 0.5% of the average total energy intake.14 Conjugated linoleic acid, for example, is found in milk fat. Even though this fatty acid technically contains a trans double bond, it is not considered a trans fat for labeling purposes because the FDA specifically states that only nonconjugated trans double bonds must be reported on nutrition labels. Conjugated linoleic acid may actually provide health benefits.3(p239) Trans fats in partially hydrogenated oils extend from 10 to 60 g/100 g, where 25 to 45 g/100 g is seen most often. In contrast, ruminant fats contain 5 to 8 g/100 g of trans fats and up to 3 g/100 g in refined edible oils.2(p869)

Major sources of trans fatty acids for American adults10 (p168)

Health Related Problems (Including FDA labeling requirements) There is no official daily value percentage for consumption of trans fats. The American Heart Association and USDA recommend that trans fats account for less than 1% of daily calorie intake, while The Nutrition Recommendations and Interventions for Diabetes, The Canadian Diabetes Association, and the American Dietetic Association recommend that their consumption

be limited, reduced, or minimized.13,14(p158) Trans fats raise low-density lipoprotein (LDL)cholesterol levels and may lower high-density lipoprotein (HDL)-cholesterol levels. LDL cholesterol is considered the bad type of cholesterol, while HDL cholesterol is considered good. They may also raise triglyceride levels in plasma and increase the clustering up of blood platelets, thus creating increased probability for developing clogged arteries (Atherosclerosis).1,3(p257),4(p211) The immune system is also affected because trans fats increase inflammation, which has been associated with heart disease, stroke, and diabetes. Trans and cis unsaturated fats are not the same, and in order to reduce the risk of heart disease, both trans and saturated fats should be reduced or avoided, and increased consumption of monounsaturated and polyunsaturated fats (that have not been hydrogenated) is encouraged. It is estimated that between 6-19% of heart attacks and related deaths could be prevented by eliminating trans fats from the American food supply.1(p648) The type of trans fat is important because, for example, while elaidic acid (a trans isomer of oleic acid) elevates LDL levels, vaccenic acid (a different trans isomer of oleic acid naturally occurring in butter) does not cause elevated LDLs.3(p256) The FDA began requiring trans fats to be listed on the nutrition facts label on food products in January 2006. The FDA estimates between $900 million and $1.8 billion would be saved in medical costs by adding trans fats to the nutrition facts label.1(p648) Companies with food products containing less than 0.5 grams of trans fat are legally allowed to say the food contains 0 grams of trans fat. 3(p257) Originally, the FDA was going to make the trans fat portion of the label a footnote, which would appear indicated by two asterisks next to the saturated fat line, and then specify at the bottom as: Includes X g of Trans fat. The American Dietetic Association (ADA) did not like the idea saying, consumers could miss important label information declared in a

footnote that is separate from other information about a products nutrient content and. . . may become increasingly confused about where on the food label they will find the information they need. 5 The FDA ended up making trans fat its own subcategory underneath the total fat heading. Alternatives to using Partially Hydrogenated Fats Many alternatives to partially hydrogenated fats have been developed and extensively studied in order to address this trans-fat epidemic. For example, palm, palm kernel oil, and coconut oils have high contents of saturated fatty acids (50%) and thus higher melting points making them good replacement fats. This is especially true for bakery and confectionery products. Fractionation of plant oils by physical methods allows the isolation of fractions of fatty acids with higher melting points from fatty acids with lower melting points making them suitable for numerous applications.2(p874), 3(p255) Another method used is interesterification. This process involves blending high saturated fats with liquid edible oils to produce fats with intermediate characteristics.2(p874), 3(p259) Margarines and shortenings have been made using this process, which ensures no trans fats while still upholding the same consistency, taste, and stability. Though these margarines contain more saturated fatty acids than conventional margarines, trans fats are taken out of the equation. An example of an interestified fat is NovaLipid. It is made using a mix of 1 part fully saturated soybean oil (high in stearic acid) and 3 parts liquid soybean oil. This results in a fat that can be used for baking and lowers the content of trans fat. Stearic acid is important because not only does it contribute to a high melting point, but it has been shown to have no influence on LDL cholesterol levels.3(p259) One study using the interestification process found that a zero-trans fat

margarine fat stock with desirable physiochemical properties could successfully be made from pine nut oil and palm stearin.8 Another avenue being explored by USDA researchers in North Dakota is the development of a unique strain of wheat waxy durum wheat. Bread is made using small amounts of shortening (about 2 tablespoons), but if 20% of the dough weight is substituted with waxy durum wheat flour in place of the shortening, a bread without trans fats is produced. This method is not yet commercially available because more research needs to be conducted.3(p398) Other technologies under development and currently being used include modification of the hydrogenation process to produce partially hydrogenated fats with low trans fat content, alterations in diacylglyceride levels, adding short- and medium-chain fatty acids, production of oil seeds with modified fatty acid composition through plant breeding and genetic engineering, and the use of tropical oils and fractionated tropical oils.2(p870),3(p259) One example of modification to the hydrogenation process is an effective reduction to <10% trans fatty acids through the use of carbon dioxide.3(p259) Work (genetic modification) on soybeans has resulted in reduced levels of saturated fat and linolenic acid and increased oleic acid content. Oil containing high levels of linolenic acid is more susceptible to degradation.7 Asoyia is a soybean oil that contains no trans fat and reduced levels of linolenic acid and thus does not deterioriate quickly, is suitable for frying, and requires no hydrogenation.3(p263) An Indian study found that a trans-free specialty fat is as stable as trans-rich oil, and only trace amounts of trans fats were formed when using transfree specialty fat or sunflower oil.9 Though many of these technologies have been available in the food industry for quite a while, many did not utilize the new techniques due to cost and technical challenges. Due to todays demand for trans-fat free or reduced products, however, these techniques are becoming more heavily relied upon.

According to one study, non-hydrogenated cottonseed oil can be used as a deep fat frying oil to reduce trans-fatty acid content in French fries.7(p1927) Cottonseed oil is naturally very low in linolenic acid and very high in linoleic acid. As mentioned earlier, linolenic acid is very susceptible to degradation. Linoleic acid does not seem to affect oil stability or negative sensory interpretations of fried food, and actually degradation products from linoleic acid seem to enhance the flavor of some fried foods.7(p1929) Oleic acid is a monounsaturated fatty acid that withstands heating better than linolenic or linoleic acids.7(p1929) This is due to the fact that as the level of unsaturation increases, breakdown of the structure increases at a faster rate (linolenic and linoleic acids are both polyunsaturated). It was found that frying French fries in cottonseed oil had a lower combined content of saturated fats and trans fats compared to the other oils used (partially hydrogenated soybean oil and partially hydrogenated canola oil). Another study conducted on donuts found that the overall liking of donuts fried in oil containing trans fat was higher than cooking them in trans-fat free oils, however, the results were not statistically significant.6 The sensory evaluation of the donuts based on moisture was considered the same for both trans-fat and trans-fat free oils. Panelists considered the donuts just about right in this regard. Even though the donuts cooked in the trans-fat free palm and cottonseed oils were ranked the lowest, donuts cooked in trans-fat free high oleic acid canola, soybean, and fully hydrogenated cottonseed oils were liked by the panelists. This suggests that it is indeed possible to produce products very much liked by consumers while ridding the food of a high-risk health hazard. A study conducted on sugar cookies found that panelists rated the original trans-rich cookie significantly higher than the trans-free cookie on basis of appearance; however, in terms of sweetness, the trans-free cookie was rated higher.10 There was no significant difference in

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terms of taste, texture, or overall liking between the two cookies. When sensory evaluation was complete, they asked the panelists which cookie they would prefer (without disclosing nutritional information) and found that 55.6% preferred the trans-free cookie. When they informed panelists of the trans fat content of both cookies, 59.6% said that they would buy the trans-free cookie, where 62% of these panelists had purchased these cookies in the past.10(p172) These numbers speak volumes because it appears that though there may be a slight difference in taste, many people accept the new taste and would prefer to purchase the more healthful option. French fries were another food studied. The initial taste, texture, taste intensity, and overall quality/liking of the trans-free fries were rated significantly higher, while the overall appearance and color compared to the trans-rich fries showed no significant difference. A majority of panelists preferred the trans fat-free fries.11 Hack et al. and Bordi et al. both noted that while there may be a 5-10% increase in food cost for switching to trans-free oil, the oils tend to last longer in the fryers than oils with trans fats. 1(p649), 11(p204) It is not common that one oil can replace another oil exactly, meaning different temperatures and different cooking times need to be considered when using a replacement oil in order to produce the best outcome. For example, fries cooked in trans-free oil have to be cooked 20 seconds longer than in deep-fat frying oil to achieve the same color.11(p204) Also, whether the food being fried was originally thawed or frozen impacts sensory characteristics of the final end product. All of these conditions need to be considered when trying to produce the best tasting, highest quality, and most healthful product. Controversies There has been much controversy and debate surrounding banning trans fats. One huge example is the FDA labeling requirements because of the fact that only 0.5 g of trans fats or higher are required to be reported on nutrition labels. Some labels even go as far as to say not a significant source of trans fat which many do not approve of because what is considered

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significant varies from person to person. People could be consuming more trans fats than they might think they are. For example, if a food contains 0.4 g of trans fats, yet it is marketed as trans-fat free, then multiple servings could really add up surpassing the 1% or less of calorieintake recommendation per day. According to Angell et. al., an increase of just 2% of total energy intake from trans fat increases the incidence of coronary heart disease by as much as 23%.15 While one side claims banning trans fats would benefit the country healthcare-wise (both death rates and economically), the other side argues that it is an infringement upon individuals constitutional rights to choose what they wish to consume. North Carolina was the first state to institute any sort of trans fat ban, which only banned their use in food served in school cafeterias.16 In 2006, New York City (NYC) became the first city in the United States to pass a regulatory restriction upon the use of partially hydrogenated vegetable oil targeting the restaurant environment.15(p81) This regulation prevents all food service establishments (in NYC) from using, storing, and/or serving food that contains partially hydrogenated vegetable oil and has a total of 0.5 g or more trans fats per serving. By November 2008, the trans fat ban was in full effect in NYC and an estimated restaurant use of artificial trans fats for frying, baking, cooking, or in spreads decreased from 50% to less than 2%.17 While some argue that this benefits public health, many compare it to the prohibition movement and tobacco rights. According to Resnick, while trans fat bans could possibly improve public health, they represent a worrisome policy trend because they open the door to further restrictions on food; the freedom to choose what we eat is at stake with bans like these. 19 Another argument from this article maintains that if other public health threats are found in foods, for example, hot dogs, could the government tax them heavily making it more difficult for

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low-income individuals to obtain cheap sources of protein? The ban in NYC received backlash not only from the freedom of choice perspective, but restaurants also claimed that they would have to spend more money on production and research.16(p104) Small restaurants were especially concerned because they are unable to afford as much as chain restaurants, making it difficult to find alternatives to partially hydrogenated vegetable oils and the many margarines and shortenings containing trans fats. Restaurant owners also found it unfair that grocery stores in NYC were still able to sell foods containing trans fat solely because products contained FDA nutrition labels.16(p107) In October 2006, Kentucky Fried Chicken (KFC) banned all of its United States restaurants from using trans fat in its chicken, completing this policy change by April 2007.16(p103) Many restaurants other than KFC have made these policy changes in fear (or in preparation) of prospective trans fat bans. Wendys has switched to a zero trans fat oil, Burger King has begun testing trans fat-free oils, and McDonalds ceased all trans fat oil use in May 2008, switching to a canola blend cooking oil.16(p103),18 Conclusion To conclude, the most important information going forward would be for further research to be conducted focused on finding alternative healthful ways to increase shelf life of food products. For the time being, people need to be vigilant when shopping for foods to ensure they are reading the label completely, avoiding foods with trans fats or foods listing partially hydrogenated oil in the ingredients. While fully hydrogenated oils should be consumed in moderation because they still contain substantial amounts of unhealthy saturated fats, at least the more dangerous hazard of trans fats is eliminated.

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Businesses operate to make profit, however, when potential health hazards are presented to the general public, they cannot solely focus on increasing shelf life to save money; they must make positive changes in order to prevent chronic disease from skyrocketing. Application to Dietetic Practice Dietitians must make it their mission to shed light on any potential health risk associated with food. If these issues are ignored, how will the public ever know that the foods they are eating could possibly be directly related to chronic disease? Going forward, dietitians should push for stricter labeling requirements for trans fats due to the fact that consuming even minute quantities of them negatively affects peoples health in major ways. It is every dietitians duty as scientists and medical professionals to ensure people are adequately informed so that they are better equipped to make decisions regarding their health. If any issue is kept in the dark because of political or monetary reasons, then dietitians have failed the people and have not maintained their ethical code.

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References 1. Hack D, Bordi P, Hessert J. Nutrition, sensory evaluation, and performance analysis of hydrogenated frying oils. International Journal Of Food Sciences & Nutrition. December 2009;60(8):647-661. Available from: SPORTDiscus with Full Text, Ipswich, MA. Accessed January 26, 2013. 2. Tarrago-Trani MT, Phillips KM, Lemar LE, Holden, JM. Research: New and Existing Oils and Fats Used in Products with Reduced Trans-Fatty Acid Content. J Am Diet Assoc. June 2006;106:867-880. Available from: ScienceDirect, Ipswich, MA. Accessed January 26, 2013. 3. McWilliams M. In: Anthony VR, ed. Foods: Experimental Perspectives - Sixth Edition. Upper Saddle River, NJ: Pearson Education Inc.; 2008: 239-240, 255, 257-59, 260, 263, 398. 4. Bettelheim FA, Brown WH, Campbell MK, Farrell SO. In: Lockwood L, Kiselica S, Kirksey B, eds. Introduction to Organic and Biochemistry - Seventh Edition. Belmont, CA: Brooks/Cole, Cengage Learning; 2010: 51, 211-212, 278-280. 5. Stahl, P. BEYOND THE HEADLINES: What's New At the FDA Informing Consumers About Trans Fat Labeling. J Am Diet Assoc. October 2000;100:1132-1134. Available from: ScienceDirect, Ipswich, MA. Accessed January 26, 2013. 6. Bordi Jr. P, Hack D, Cocci S, Rager M, Hessert Jr. S. Comparing Trans-Fat and TransFat-Free doughnut shortenings based on sensory evaluation and oil degradation. Journal Of Sensory Studies. February 2009;24(1):41-57. Available from: Academic Search Complete, Ipswich, MA. Accessed February 16, 2013. 7. Daniel DR, Thompson LD, Shriver BJ, Wu C-K, Hoover LC. Research: Nonhydrogenated Cottonseed Oil Can Be Used as a Deep Fat Frying Medium to Reduce Trans-Fatty Acid Content in French Fries. J Am Diet Assoc. December 2005;105:19271932. Available from: ScienceDirect, Ipswich, MA. Accessed February 16, 2013. 8. Adhikari P, Zhu X-M, Gautam A, et al. Scaled-up production of zero-trans margarine fat using pine nut oil and palm stearin. Food Chemistry. September 2009;119:1332-1338. Available from: ScienceDirect, Ipswich, MA. Accessed February 16, 2013. 9. Rani A, Reddy S, Chetana R. Quality changes in trans and trans free fats/oils and products during frying. European Food Research And Technology. February 2010;230(6):803-811. Available from: Science Citation Index, Ipswich, MA. Accessed February 16, 2013. 10. Bordi P, Rager M, Hack D, Hessert S. Development and sensory evaluation of a trans fat-free sugar cookie. Journal Of Foodservice. October 2007;18(5):167-175. Available from: Business Source Complete, Ipswich, MA. Accessed February 16, 2013. 11. Bordi P, Stokols J, Hack D, Rager M, Hessert S. Sensory evaluation of salted trans fatfree french fries vs. salted trans fat french fries. Journal Of Foodservice. October 2007;18(5):198-205. Available from: Business Source Complete, Ipswich, MA. Accessed February 16, 2013.

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12. List G, Jackson M. The Battle Over Hydrogenation (1903-1920). The AOCS Lipid Library. 2010. Available at: http://lipidlibrary.aocs.org/history/hydrogenation/index.htm. Accessed February 23, 2013. 13. Kris-Etherton P, Innis S, American Dietetic A, Dietitians of C. Position of the American Dietetic Association and Dietitians of Canada: dietary fatty acids. J Am Diet Assoc. September 2007;107(9):1599-1611. Available from: MEDLINE, Ipswich, MA. Accessed March 9, 2013. 14. Brandt E. Deception of Trans Fats on Food and Drug Administration Food Labels: A Proposed Revision to the Presentation of Trans Fats on Food Labels. American Journal Of Health Promotion. January 2011;25(3):157-158. Available from: SPORTDiscus with Full Text, Ipswich, MA. Accessed February 16, 2013. 15. Angell S, Cobb L, Curtis C, Konty K, Silver L. Change in Trans Fatty Acid Content of Fast-Food Purchases Associated With New York City's Restaurant Regulation. Annals Of Internal Medicine. July 17, 2012;157(2):81-87. Available from: Academic Search Complete, Ipswich, MA. Accessed February 16, 2013. 16. Filosa C. Trans Fat Bans: The Next Regulatory Taking? Journal Of Legal Medicine. March 2008;29(1):99-115. Available from: Academic Search Complete, Ipswich, MA. Accessed February 16, 2013. 17. Angell S, Silver L, Bassett M, et al. Cholesterol Control Beyond the Clinic: New York City's Trans Fat Restriction. Annals Of Internal Medicine. July 21, 2009;151(2):129W33. Available from: Academic Search Complete, Ipswich, MA. Accessed February 16, 2013. 18. Hitti M. McDonalds Drops Trans Fats from Food. WebMD. 2008. Available at: http://www.webmd.com/food-recipes/news/20080522/mcdonalds-drops-trans-fats-frommenu. Accessed March 9, 2013. 19. Resnik D. Trans fat bans and human freedom. American Journal Of Bioethics. March 2010;10(3):27-32. Available from: CINAHL Plus with Full Text, Ipswich, MA. Accessed February 16, 2013.