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Int.J.Curr.Microbiol.App.Sci (2017) 6(6): 1283-1296

International Journal of Current Microbiology and Applied Sciences ISSN: 2319-7706 Volume 6 Number 6 (2017) pp. 1283-1296 Journal homepage: http://www.ijcmas.com

Review Article https://doi.org/10.20546/ijcmas.2017.606.151

Chemistry and Use of Artificial Intense Sweeteners

B. Kapadiya Dhartiben* and K.D. Aparnathi

Dairy Chemistry Department, SMC College of Dairy Science, Anand Agricultural University, Anand– 388110 (Gujarat),

*Corresponding author

ABSTRACT

Now a days free are very much popular because of their less

K e yw or ds calorie content. So uses various artificial sweeteners which are low in calorie content instead of high calorie sugar. Artificial Artificial sweeteners/low calorie sweeteners are synthetic sugar substitutes but may Intense be derived from naturally occurring substances, including herbs or sugar Sweeteners. itself. The growing consumer interest in health and its relationship with diet Article Info has led to a considerable rise in the demand for low calorie products.

Accepted: Artificial sweeteners are also known as intense sweeteners because they are 19 May 2017 many times sweeter than regular sugar. Therefore, it is very important to Available Online: 10 June 2017 understand their chemistry in relation to the stability on processing and storage of food products in which these sweeteners are used.

Introduction

Sweeteners are additives which provide the These alternative sweeteners could either be basic of to a food product. from a natural source or artificially derived by Traditionally are used as sweeteners in chemical synthesis. These artificial food. In addition to sweet taste they provide sweeteners are chemically very different from energy of 4 kcal/g. However, rising obesity the or other nutritive sweeteners that rates suggest avoiding over consumption of they are replacing in a food system. calories. The growing consumer interest in Therefore, it very is important to understand health and its relationship with diet has led to their physicochemical properties, taste a considerable rise in the demand for low characteristics and stability for formulation, calorie fat products (Martínez-Cervera et al., processing and storage of food products and 2012). The substances used to replace sugar beverages in which these sweeteners are used are called alternative sweeteners or sugar (Nelson, 2000). substitute.

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Aspartame, acesulfame K, , was developed after accidental , cyclamate, , and discovery of sweet taste of a similar are the commonly reported artificial compound (5, 6-dimethyl-1, 2, 3-oxathiazin- sweeteners. Among the artificial sweeteners 4(3H)-one 2, 2-dioxide) in 1967 by Karl saccharin, cyclamate and are Claussat Hoechst AG (DuBois and Prakash, considered as first generation sweeteners, 2012). In 1976 Tate and Lyle, a British sugar whereas, acesulfame-K, sucralose, alitame, company, was looking for ways to use advantame and neotame are new generation sucrose as a chemical intermediate. In sweeteners (DuBois and Prakash, 2012). collaboration with Professor Leslie Hough‟s laboratory at Queen Elizabeth College, History of discovery halogenated sugars were being synthesized and tested. Hough asked a young Indian The most of the popular artificial sweeteners graduate student, Shashikant Phadnis to “test” were discovered by accident, rather than by the chlorinated sugar compound. Phadnis deduction structural design (Hough, 1993). misunderstood the instruction and thought Saccharin was discovered in 1878 in the that Hough told him to "taste" it, so he tasted laboratory of Ira Remsen at Johns Hopkins the compound. He found that the compound University in Maryland by Constantine had exceptionally high potency of sweetness. Fahlberg, a post-doctoral research associate His observation indicated that the selective who was trying to oxidize toluene chlorination of sugar could result in intensely sulfonamides. While working in the lab, he sweet compounds. This discovery led to a spilled a chemical on his hand. Later while series of studies and ultimately identified the eating dinner, Fahlberg noticed a more compound as 1, 6-dichloro-1, 6-dideoxy-β-D- sweetness in the bread he was eating. He fructofuranosyl-4-chloro-4-deoxy-α-D- traced the sweetness back to the chemical, galactopyranoside and named as sucralose later named saccharin. (, 2006).

Michael Sveda, a graduate student at the After the discovery of aspartame, a highly University of Illinois discovered the sweet potent dipeptide sweetener was designed from taste of cyclamate in 1937. While working on structure activity relationship studies at Pfizer the synthesis of anti-pyretic (anti-fever) Central Research Inc., utilizing a terminal in the laboratory there he was smoking a amide group instead of methyl of . He put his cigarette down on the lab aspartame. Alitame was patented in 1983 and bench and when he put it back in his mouth, currently marketed under the brand name he noticed that the cigarette tasted sweet. He Aclame (Hough, 1993). Advantame is a new realized that the substance he synthesized was ultrahigh potency sweetener and on his fingers which imparted the sweet taste enhancer. The sweet taste of advantage was to the cigarette (Orphardt, 2003). discovered at the Ajinomoto Company where it was subsequently developed and Aspartame was discovered in 1965 by James commercialized (Amino et al., 2008; Hazen, Schlatter, a chemist working at G.D. Searle 2012). The sweet taste of neotame was Pharmaceutical Company while synthesizing discovered in 1992 by Claude Nofre and Jean- aspartame as an intermediate step in Marie Tinti at Universite Claude Bernard in generating a tetrapeptide of the hormone, Lyon, France. The French scientists invented gastrin, for use in assessing an anti-ulcer neotame from a simple N-alkylation of candidate (Walters, 2013). Acesulfame aspartame (DuBois and Prakash, 2012).

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Chemistry and applications sauces. Because of its stability, saccharin can be used in , and canning. The The artificial sweeteners are chemical permitted levels of use vary from 100 to 500 compounds with a diverse range of chemical mg/kg depending on the food category structuresincluding sulfonamides, sucrose (Mortensen, 2006). derivatives, peptides and their derivatives (Seldman, 2010). Due to different However, when saccharin is heated to physicochemical properties of artificial decomposition (380°C), all three saccharin sweeteners, they used as a stable sweetening forms emit toxic fumes of oxides and agent in a wide range of food products. sulfur oxides. Although saccharin does not decompose under the conditions encountered Saccharin during typical , some occurs after prolonged exposure to Saccharin is chemically known as o- extreme conditions of temperature or pH, at sulfabenzamide (2, 3-dihydro-3- pH < 2.0 and at extremely high temperatures, oxobenzisosulfonazole). It is sulphonamide hydrolytic decomposition of saccharin to (2- derivative of toluene and available as sulfobenzoic acid and 2-sulfamoyl benzoic saccharin, saccharin and acid). Neither of these compounds exhibits saccharin (DuBois and Prakash, 2012). sweetness (Nelson, 2000). Saccharin (benzoic sulfimide) is a very stable organic acid with a pKa of 1.6 and chemical Cyclamate formula C7H5NO3S. It has a of 183.2 g/mol and a density of 0.83 g/cm3 Cyclamate is a member of a group of of (Walter, 2013). Saccharin and its sodium and cyclamic acid (cyclohexylsulfamic acid). calcium salts are white crystalline solids. The Three different compounds are referred to as acid form of saccharin is sparingly cyclamates: cyclamic acid, calcium cyclamate soluble (0.2% at 20°C), whereas sodium and (Mortensen, 2006). saccharin (100% at 20°C) and calcium The sodium and calcium salts were saccharin (37% at 20°C) are readily soluble commonly used as artificial sweetener until. (Nelson, 2000; DuBois and Prakash, 2012). The sodium is the most commonly used Saccharin acid is only slightly soluble in form. It is a white crystalline salt with good water. Sodium saccharin is the most widely solubility (O'Donnell, 2007). Cyclamate and used salt because of its high solubility and its sodium and calcium salts are crystalline ease of production. solids. In its acid form it is a strong acid with pKa of 1.71 and 71 and the pH of a 10% Calcium saccharin is also used in a variety of aqueous solution is approximately 0.8–1.6. food applications. It is interesting to note that Although the acid has good water solubility the form of saccharin has no effect on its (∼13.3% at 20°C), its high acidity results in sweetness intensity. In the dry solid form, preference for the very soluble sodium saccharin and its salts are very stable. In cyclamate (∼20% at 20°C) or calcium solution it has excellent hydrolytic, thermal, cyclamate (∼25% at 20°C) salts (DuBois and and photo stability. Stability is not affected by Prakash, 2012). Sodium and calcium temperatures and pH normally encountered in cyclamate are strong electrolytes, which are food and beverage manufacturing, including highly ionized in solution, fairly neutral in table-top sweeteners, desserts, yoghurt, ice- character, and have little buffering capacity. cream, baked goods, jam, preserves, Both salts exist as white crystals or white marmalade, soft drinks, sweets, and 1285

Int.J.Curr.Microbiol.App.Sci (2017) 6(6): 1283-1296 crystalline powders. They are freely soluble in 57.1% carbon, 6.2% , 9.5% nitrogen, water (1g/5 ml) at concentrations far in excess and 27.2% . It has the chemical of those required for normal use, but have formula C14H18N2O, a molar mass of 294.3 limited solubility in oils and nonpolar g/mol, and a density of 1.3 g/cm3. Aspartame solvents (Hunt et al., 2012). Sodium and has a melting point between 246-247 ºC and calcium cyclamate decompose at 260°C. will decompose at temperatures above 280 ºC. Aspartame has two ionizable groups. Because Cyclamic acid has a melting point of 169– it is a dipeptide, it is amphoteric, and those 170°C. They are stable at baking temperatures sites can dissociate hydrogen ions. The pKa and during heating in solutions. They have a of the two sites are 3.1 and 7.9 at 25°C. The long shelf life in their dry state and are not molecule still exhibits sweetness after the hygroscopic. Cyclohexamine, a metabolic sites are dissociated. The isoelectric point for breakdown product, is produced from the aspartame is 5.2 (Nelson, 2000). Aspartame is microflora of the intestine but is not produced slightly soluble in water (approximately 1.0% during the processing of food systems at 25°C) and is sparingly soluble in . It (Nelson, 2000). Cyclamates are stable in heat is not soluble in or oils. Solubility is a and cold and have good shelf-life. The function of both temperature and pH. Its stability and solubility in water facilitate the solubility is ideal at pH ranges 3.0 to 5.0 use of cyclamates in foodstuffs and beverages (Abegaz et al., 2012). The solubility of (Mortensen, 2006). Cyclamate is stable under aspartame is sufficient for all product conditions likely to be encountered in soft applications. In liquid applications such as drinks, that is, pH range 2–7, pasteurization beverages, typical concentrations are in the and UHT treatments (O'Donnell, 2007). range of 0.01% to 0.2%. In water, the Cyclamate solutions are stable to heat, light, solubility is approximately 1% at 20°C and and air throughout a wide pH range (Hunt et 3% at 50°C. Solubility can be significantly al., 2012). Cyclamate is stable from pH 2 to 7 increased if aspartame is dissolved in an acid and can withstand heat treatments such as solution. For example at 20°C, approximately pasteurization and UHT (O'Donnell, 2007). 4% aspartame can be dissolved in a 5% citric Where pasteurization is applied, the HTST acid solution, and about 10% can be dissolved method is recommended, whereby more than in a 20% solution. This is helpful 90% of the aspartame will remain when preparing stock solutions (Ajinomoto, (Ajinomoto, 2013). Because aspartame may 2013). lose its sweetening power upon prolonged exposure to heat, it is not recommended for Its stability is determined by time, use in recipes requiring lengthy cooking or temperature, pH and moisture content. Under baking. dry conditions, the stability of aspartame is excellent; it is, however, affected by Aspartame extremely high temperatures which are not typical for the production of dry food Aspartame consists of three components products. At 25°C, the maximum stability is namely , , and observed at pH ∼4.3. Aspartame functions . Aspartame is a dipeptide composed very well over a broad range of pH conditions of two amino , L-aspartic acid and the but is most stable in the weak acidic range in methyl ester of L-phenylalanine (Abegaz et which most exist (between pH 3 and pH al., 2012). The true chemical name is N-L-α- 5). A frozen dairy dessert may have a pH aspartyl-L-phenylalanine-1-methyl ester ranging from 6.5 to more than 7.0 but, due to (Nelson, 2000). Aspartame is composed of the frozen state, the rate of reaction is 1286

Int.J.Curr.Microbiol.App.Sci (2017) 6(6): 1283-1296 dramatically reduced. In addition, because of functional characteristics. Aspartame was sold the lower free moisture, the shelf life stability exclusively by the patent holder and of aspartame exceeds the predicted shelf life manufacturer (Searle) by the brand names stability of these products (Abegaz et al., NutraSweet in food products and as a 2012). tabletop sweetener (Kroger et al., 2006).

Aspartame can withstand high-temperatures Acelfame K at a short-time and ultra-high temperature processing, such as pasteurization and Acesulfame is an oxathiazinone dioxide (6- asceptic processing (Kroger et al., 2006). methyl-1, 2, 3-oxathiazine-4(3H)-one-2, 2, Where pasteurization is applied, the HTST dioxide or 3, 4-dihydro-6-methyl-1, 2, 3- method is recommended, whereby more than oxathiazin-4-one-2, 2-dioxide). Chemically, it 90% of the aspartame will remain bears some structural resemblance to (Ajinomoto, 2013). Because aspartame may saccharin. The hydrogen atom on the nitrogen lose its sweetening power upon prolonged is quite acidic (pKa ~2) and it readily forms exposure to heat, it is not recommended for salts. It is sold as the potassium salt, so it use in recipes requiring lengthy cooking or often referred to as "acesulfame-K" (Walters, baking. Aspartame has a free amino group 2013). Its formula is C4H4NO4SK with a that reacts with carbonyl-containing food molecular weight of 201.24. It is manufacture ingredients. Aspartame has a peptide that by chemical derivation from acetoacetic acid causes it to be susceptible to hydrolysis and purified through re-crystallization causing its taste in sweetness to gradually (O'Donnell, 2007). It is a white, non- degrade. Being an it can react with hygroscopic crystalline product. aldehydes. At elevated temperature under acidic and alkaline pH, aspartame is unstable Acesulfame-K does not show a defined and rapidly degrades to the rate where melting point although decomposition starts at sweetness will gradual be lost. For this reason above 200°C (Nelson, 2000). The density of aspartame is not ideal for cooking and baking. solid acesulfame-K is 1.81 g/cm3 while that of The shelf life of aspartame can be prolonged the commercial acesulfame-K has a range of between nine months to a year when used in 1.1-1.3 kg/dm3.Acesulfame K dissolves combination with other non-nutritive readily in water, forming a clear solution. sweeteners (e.g. acesulfame K), a more stable Solubility increases with increasing sweetener. Aspartame can be encased with temperature (1300 gm/lit at 100°C). Its fats. An encapsulated version of aspartame is crystalline solid has good water solubility available for use in baked products to enhance (27% at 20°C) (DuBois and Prakash, 2012).It its stability properties. The majority is used in is only slightly soluble in organic solvents soft drinks, which account for more than 70 such as methanol, , and per cent of aspartame consumption (Nelson, 2000).The shelf life of pure, solid (Anonymous, 2012). As aspartame is acesulfame K appears to be almost unlimited approximately 200 times sweeter than sugar, at room temperature. each °Brix of sugar to be replaced requires approximately 50 to 60 mg/l of aspartame. Samples kept at room temperature for more Aspartame is suitable for sweetening many than six years and either exposed to or products including yogurts, milkshakes, protected from light showed no signs of and quark. Frozen desserts are traditionally decomposition or differences in analytical sweetened with sucrose for its sweetness and data compared with freshly produced material

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(Klug and von Rymon Lipinski, 2012). sucrose, so the name is rather misleading. Acesulfame K is stable in aqueous solutions Common brand names of sucralose-based over a wide range of temperatures, pH levels sweeteners include ®. Sucralose is and light exposure for use in beverage also known as 4, 1‟, 6‟-trichlorosucrose. applications (DuBois and Prakash, 2012). At Sucralose is made from sucrose (common pH <3, acesulfame K is slightly less stable. table sugar) by the selective replacement of Acesulfame-K works excellent when foods three hydroxyl groups with atoms, a have a pH of 3 to 7 (Nelson, 2000). process that occurs with inversion of Acesulfame K is suitable for low-calorie and configuration at the 4 position of the galacto- diet beverages because of its good stability in analog (Grotz et al., 2012). Its chemical aqueous solutions even at low pH typical of formula is C12H19O8Cl3 (MW 397.35) diet soft drinks (Klug and von Rymon Sucralose is a white, odorless crystalline Lipinski, 2012). Acesulfame K is stable in its powder and is readily dispersible and soluble dry state, even at high temperatures. in water, methanol, and ethanol. At 20°C, a Therefore, the sweetener can withstand the 280 g/l solution of sucralose in water is temperatures encountered during baking, possible. Sucralose presents Newtonian sterilization, and pasteurization. It is not characteristics, a negligible lowering utilized by and is therefore of surface tension, and no pH effects, and its not subject to microbial breakdown (Nelson, solubility increases with increasing tempera- 2000). Acesulfame K-containing beverages ture. In ethanol, the solubility ranges from can be pasteurized under normal approximately 110 g/l at 20°C to 220 g/l at pasteurization conditions without loss of 60°C and solubility of sucralose in ethanol sweetness. Pasteurizing for longer periods at facilitates in formulating alcoholic beverages lower temperatures is possible, as is short- and flavor systems (Nikoleli and Nikolelis, term pasteurization for a few seconds at high 2012). temperatures. Sterilization is possible without losses under normal conditions (i.e., temp. at It has a negligible effect on the pH of 100°C for products having lower pH levels solutions. Sucralose exerts negligible and 121°C for products around and >pH 4). lowering of surface tension (Grotz et al., Under UHT and microwave treatment, 2012). Solubility increases with increasing acesulfame K is stable. In baking studies, no temperature. Sucralose is also soluble over a indication of decomposition of acesulfame K wide pH range, although solubility decreases was found even when biscuits with low water slightly with increasing pH (Nelson, content were baked at high oven temperatures 2000).The shelf life of pure dry sucralose is at for short periods. This corresponds to the least two years when stored at 25°C or below. observation that acesulfame K decomposes at Dry sucralose is, however, sensitive to temperatures well above 200°C (Klug and elevated temperatures. Storage at high von Rymon Lipinski, 2012). It is marketed temperatures for extended periods can result under the brands Sunett® or SweetOne® in color formation. The shelf life can also be (Anonymous, 2012). affected by packaging materials and container head space, so care should be taken to adhere Sucralose to the recommended packaging and storage conditions (Grotz et al., 2012). Because of the The only non-caloric sweetener prepared from three substituted sites (at which chlorine sucrose. Although the name Sucralose ends in replaces a hydroxyl group on the sucrose -ose, it is not a basic sugar like or molecule), the reactivity of sucralose is much

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Int.J.Curr.Microbiol.App.Sci (2017) 6(6): 1283-1296 lower than that sucrose. For example, under from the amino acids L-aspartic acid and D- acidic conditions, sucrose hydrolyzes to its alanine and a new amine. Alitame is the component sugars, glucose and . generic name for L-α-aspartyl-N-(2, 2, 4, 4- Sucralose hydrolyzes under highly acidic tetramethyl - 3- thetanyl)- D-alaninamide conditions, and hydrolysis increases with hydrate (O'Donnell, 2007). Alitame is formed increasing temperatures. However, the rate of from the amino acids L-aspartic acid and D- hydrolysis is much lower than that of sucrose. alanine, with a novel C-terminal amide Since the primary reaction sites are moiety. It is this novel amide (formed from 2, substituted, sucralose is also less chemically 2, 4, 4-tetramethylthietanylamine) that is the reactive than sucrose. In food systems, key to the very high sweetness potency of sucralose does not interact with other food alitame (Auerbach et al., 2012). Incorporation molecules. In aqueous systems, sucralose is of D-alanine as second amino acid, in place of stable over a wide range of pH. At pH 3 or L-phenylalanine, gives optimum sweetness. lower, some hydrolysis occurs, but the Increased steric and lipophilic bulk on small amount is very small, and at pH 4–7.5, rings led to high sweetness potency with virtually no sucralose is lost when stored at another sulphur derivative, derived from 2, 2, 30°C for a year (Nelson, 2000). 4, 4-tetramethyl-3-aminothietane proved highly sweet (Hough, 1993).It is a crystalline Sucralose is extremely heat stable, even when powder that is odorless and non-hygroscopic. exposed to high temperature food processing The melting point of alitame is 136–147°C. such as pasteurization, sterilization, UHT and Alitame is soluble in water and forms clear baking. The stability of sucralose during food solutions. Its isoelectric point is 5.7. This is manufacture has been confirmed by a series also the pH at which alitame is least soluble of processing trials. Sucralose maintains its (13% at 25°C) (Anonymous, 2012). It is sweetness and flavour through storage soluble in polar solvents such as methanol, without the development of off-flavours even ethanol, and . It is not soluble at low pH. Shelf-life studies have in nonpolar solvents such as fats, oils, or demonstrated that products sweetened with chloroform. The solubility of alitame sucralose retain their sweetness throughout increases with increasing temperature and extended periods of storage (Anonymous, with pH levels greater or less than the 2012). The taste, stability and isoelectric point (Nelson, 2000). At the physicochemical properties of sucralose mean isoelectric pH, alitame is very soluble in that it is a very versatile sweetener suitable water. for use in a wide variety of food products (Grotz et al., 2012). Sucralose is used in a Excellent solubility is also found in other wide range of food products and beverages. polar solvents. As expected from the Among these are soft drinks, desserts, ice- molecule‟s polar structure, alitame is virtually cream, confectionery, preserves and sandwich insoluble in lipophilic solvents. In aqueous spreads. The permitted levels of use vary solutions, the solubility rapidly increases with from 10 mg/l to 1000 mg/kg depending on the temperature and as the pH deviates from the food category. It is sold under the name isoelectric pH (Auerbach et al., 2012). Splenda (Mortensen, 2006). Alitame is an amino acid derivative and, therefore, not completely stable. It does Alitame hydrolyze in acid conditions, but is more stable than aspartame under certain conditions Alitame is second-generation dipeptide (O'Donnell, 2007). The unique amide group is sweetener Alitame is a sweetener formed in part responsible unique stability 1289

Int.J.Curr.Microbiol.App.Sci (2017) 6(6): 1283-1296 characteristics of alitame compared with those catalyst (Amino et al., 2008). Advantame has of aspartame. Because of its unique amide a molecular weight of 476.52 g/mol and the group, alitame exhibits superior stability monohydrate has a melting point of 101.5°C. under a variety of conditions. It is less likely Advantame is a crystalline solid with to hydrolyze than the methyl ester of solubility in water of approximately 0.10% at aspartame. The half-life of alitame in aqueous 25°C (DuBois and Prakash, 2012). solutions at pH 7–8 and 100°C ranges from Considering the ultrahigh potency of hours to days. The dipeptide bond of alitame advantame, its solubility in water, ethanol and can hydrolyze, forming two final reaction ethyl is more than sufficient for the products: aspartic acid and the alanine amide. required functionality (Bishay and Bursey, These end products do not exhibit sweetness. 2012). Advantame is more stable than aspartame under higher temperature and Alitame is stable in carbonated beverages and higher-pH conditions." In general, 4.5 is can withstand the pH levels typical of soft considered a higher pH condition, but he drinks (pH 2–4). Alitame does not cyclize. At notes all formulations are unique (Hazen, neutral pH under aqueous conditions, it is 2012). Advantame is stable under dry stable for more than a year (Anonymous, conditions. 2012). Because it is stable during heating, alitame can be used in processed foods such In aqueous food systems, its stability is as baked goods. In particular, high levels of similar to aspartame with greater stability reducing sugars, such as glucose and , predicted at higher and neutral pH, as well as may react with alitame in heated liquid or higher temperature conditions (e.g., baking semiliquid systems, such as baked goods, to and other prolonged heating processes) and in form Maillard reaction products. At pH <4, yogurt. The stability of advantame is off can form when , dependent upon pH, moisture, and ascorbic acid, and some colors are temperature. Advantame in dry applications, also present (Nelson, 2000). Alitame is such as tabletop or powdered soft drinks, is currently marketed in some countries under very stable and maintains its functionality the brand name Aclame (Hough, 1993). during normal storage and handling conditions. Advantame gives stability in Advantame carbonated soft drinks. Advantameis also stable in tabletop mix, when stored at 25°C Advantame, one of the latest additions to the and 60% relative humidity (RH). Under these group of non-nutritive high-intensity conditions, advantame displays the same sweeteners is an N substituted (aspartic acid stability profile as aspartame indicating that portion) derivative of aspartame that is similar both sweeteners follow the same degradation in structure to neotame. Its chemical name is mechanism (Bishay and Bursey, 2012). N-[N-[3-(3-hydroxy-4-methoxyphenyl) Advantame was demonstrated to perform very propyl]-a-aspartyl]-L-phenylalanine 1-methyl well as a sweetener in coffee (hot and warm), ester, monohydrate (Otabe et al., 2011). The iced tea, powdered beverage formulations, starting materials of advantame are aspartame and as a flavor enhancer in beverages, and . Advantame is synthesized from chewing gum and yogurt. These properties aspartame and HMPA in a one step process make advantame a high-intensity sweetener in by reductive N-alkylation, carried out with a variety of products (Otabe et al., 2011). hydrogen in the presence of a platinum

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Table.1 Sweetness potency of intense artificial sweeteners

Sweetener Potency (More times compared to sucrose) Cyclamate 30 Aspartame 180 Acesulfame K 200 Saccharin 300 Sucralose 600 Alitame 2000 Neotame 8000 Advantame 20000

Saccharin Cyclamate

Aspartame Acelfame K

Sucralose Alitame

Advantame Neotame Chemical structure of artificial sweeteners

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Allowable levels of advantame in food heated. As a dry ingredient Neotame is stable products are: 2 ppm in nonalcoholic enough for storage of at least five years, in beverages; 1 ppm in milk products, 1 ppm in temperatures between 15º and 30ºC and at frozen dairy products and 50 ppm in chewing relative humidity between 35% and 60% gum (Hazen, 2012). when the inner bag is sealed. However, when in a system of moisture the rate of Neotame degradation of Neotame becomes a function of pH, temperature, and time. Neotame is a new high-potency nonnutritive sweetener which is considered as the potential When used as a sweetener in carbonated soft successor of aspartame. It is a derivative of drinks and ready-to-drink beverages (pH 2.9- aspartame, produced by adding a 6-carbon 4.5), if these products are properly stored and (neohexyl) group to the amine nitrogen of handled, Neotame remains stable adequately aspartame (O'Donnell, 2007). Its chemical for the normal shelf life. For baked goods name is N-[N-(3, 3-dimethylbutyl)-L-α- Neotame exhibits high stability. In one study aspartyl]-L-phenylalanine 1–methyl ester. Its only 15% of Neotame was lost (85% retained) is C20H24N2O5 and it has a during baking and only 19% was lost (81% molar mass of 378.46 g/mol (Boone, 2009). retained) after 5 days of storage at room The solubility in water of neotame is 12.6 g/l temperature. In dairy products such as yogurt at 25°C (Nofre and Tinti, 2000). The only 1% of Neotame was lost after ultra-high solubility of neotame in water, temperature (UHT) pasteurization. There was and ethanol at a range of temperatures no noticeable degradation after fermentation illustrates how neotame behaves in various followed by 5 weeks in refrigerated storage food matrices. Neotame is very soluble in (Anonymous, 2006). The high potency of ethanol at all temperatures tested. The neotame allows it to maintain a highly solubility of neotame increases in both water competitive relative cost (cost per sucrose and ethyl acetate with increasing temperature. equivalent). Therefore it is possible to achieve This solubility may create opportunities for a cost reduction in almost any given food and beverage manufacturers to use sweetener blend BFNE (2010). neotame in a wide range of liquid systems (Mayhew et al., 2012). As a dry ingredient, Regulatory aspects neotame has excellent stability and will function well in finished dry products such as Food ingredients are evaluated and/or powdered soft drinks and dessert mixes. In regulated by numerous national and food where moisture is present, the stability international bodies. International groups that of neotame will be influenced by pH, evaluate use of sweeteners include expert temperature and time. In in solution, it shows scientific committees such as the Scientific highest stability at pH 4.5. At low pH, Committee on Food (SCF) of the European neotame a dipeptide methyl ester, hydrolyzes commission (EC), the Joint Expert Committee to the dipeptide carboxylic acid, the non- of Food Additions (JECFA) of the United sweet major metabolite of neotame in humans Nations Food and Agricultural Organization (BFNE, 2010; Nofre and Tinti, 2000). (FAO) and the World Health Organization (WHO) (Nabors, 2001). In India Saccharin, Neotame is stable enough in heat that it can Aspartame, Acesulfame k, Sucralose are be used for baking and cooking unlike permitted under FSSAI, 2011. Aspartame which easily degrades when

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Sweetness characteristics health related general concerns of artificial sweeteners, there are several other sweetener Sucrose is the standard sweetener to which all specific health risks (Williams et al., 2008; other sweeteners are compared. The relative Takayama et al., 2000; Mann et al., 2000; sweetness of sucrose is set to 1 or 100%. A Boone, 2009; Van Stempvoort et al., 2011; growing number of alternative sweeteners Buerge et al., 2009). Therefore, usefulness of exist on the market; all with somewhat the artificial sweeteners for purpose of their different sweetness compared to sucrose. use and safety has become questionable. Each high-intensity sweetener has its own characteristics. Using the right sweetener or Because of increasing consumer desire for combination of sweeteners is the key in products that deliver great taste with fewer product success. calories, the need for improved zero- and reduced-calorie sweetener technologies will The potency of an intense sweetener is an continue. Eight artificial sweeteners are used important basic characteristic, due to its worldwide. Those are acesulfame-K, impact on a variety of issues including advantame alitame, aspartame, cyclamate, relative cost and amounts consumed (the neotame saccharin and sucralose. However, latter impacting safety considerations). the main barrier in using any intense Different artificial sweeteners provide sweetener is technical one. It is never easy to different sweetness potency, which is replicate the mouth feel and taste of a full presented in Table below. sugar product.

In reality the potency is affected by many It requires the careful blending of sweeteners, factors such as temperature, viscosity, pH and alongside the use of flavour and texture medium in which the sweetener is used. The enhancing ingredients, to optimize the presence of other sweeteners (both intense sensory characteristics and to bring a low/zero and nutritive sweeteners) may have impact on calorie product in to line with the 'full-sugar' the potency of the sweetener as well as other version. Moreover, the usefulness of the sensory attributes (Bakal and Cash, 2006). artificial sweeteners for the purpose they are used and their safety is doubtful. Health hazards References The artificial sweeteners are a mix of laboratory chemicals used to create a „sweet‟ Abegaz, E.G., Mayhew, D.A., Butchko, H.H., taste. The accumulating evidence suggests Wayne Stargel, W., Phil Comer, C. and that frequent consumers of these sugar Andress, S.E. 2012. Aspartame. In substitutes may also be at increased risk of „Alternative Sweeteners” (Lyn O‟brien excessive weight gain (Swithers and Nabors Ed.) CRC Press, Taylor and Davidson, 2008; Davidson and Swithers, Francis Group, 6000 Broken Sound 2004; Fowler et al., 2008), metabolic Parkway NW, Suite 300 Boca Raton, syndrome (Yang, 2010), type 2 FL 33487-2742. pp. 57-76. (Brown et al.,2010; Swithers et al., 2013), Ajinomoto, 2013. Ajinomoto Aspartame - cancer (Soffritti et al., 2006; Howe et al., Technical booklet. Ajinomoto Food 1977; Andreatta et al., 2008), hypertension Ingredients LLC, 8430 West Bryn (Swithers et al., 2013) and cardiovascular Mawr Avenue, Suite 635, Chicago, disease (Jang et al., 2011). In addition to these Illinois 60631-3444, USA.

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How to cite this article:

Kapadiya Dhartiben, B. and Aparnathi, K.D. 2017. Chemistry and Use of Artificial Intense Sweeteners. Int.J.Curr.Microbiol.App.Sci. 6(6): 1283-1296. doi: https://doi.org/10.20546/ijcmas.2017.606.151

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