Title: Alternative Sweeteners

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4 Aspartame Harriett H. Butchko, W. Wayne Stargel, C. Phil Comer, Dale A. Mayhew, and Sue E. Andress The NutraSweet Company, Mount Prospect, Illinois I. INTRODUCTION AND HISTORY Over three decades have elapsed since aspartame was discovered accidentally in 1965 by G. D. Searle and Co. chemist James Schlatter (1, 2). At present, it is estimated that aspartame is used in approximately 6000 different products worldwide. The safety of aspartame has been tested extensively in animal and human studies. It is undoubtedly the most thoroughly studied of the high-intensity sweeteners. The safety of aspartame has been affirmed by numerous scientific bodies and regulatory agencies, including the Joint FAO/WHO Expert Committee on Food Additives (JECFA) of the Codex Alimentarius (Food and Agriculture Organization/World Health Organization) (3), the Scientific Committee for Food of the Commission of European Communities (4), the U.S. Food and Drug Administration (FDA) (5, 6), and the regulatory agencies of more than 100 other countries around the world. II. PHYSICAL CHARACTERISTICS AND CHEMISTRY A. Structure Aspartame is a dipeptide composed of two amino acids, l-aspartic acid and the methyl ester of l-phenylalanine. The chemical structure of aspartame is depicted in Fig. 1. Aspartame sold for commercial use meets all requirements of the Food Chemical Codex (7). 41
42 Butchko et al. Figure 1 Chemical structure of aspartame. B. Stability In liquids and under certain conditions of moisture, temperature, and pH, the ester bond is hydrolyzed, forming the dipeptide, aspartylphenylalanine, and methanol. Ultimately, aspartylphenylalanine can be hydrolyzed to its individual amino acids—aspartate and phenylalanine (8, 9). <strong>Alternative</strong>ly, methanol may also be hydrolyzed by the cyclization of aspartame to form its diketopiperazine (DKP) (Fig. 2). The decomposition of aspartame is indicative of first-order kinetics, and stability is determined by time, moisture, temperature, and pH. Under dry conditions, the stability of aspartame is excellent; it is, however, affected by extremely high temperatures that are not typical for the production of dry food products (10, 11). The combined effect of time, temperature, and pH on the stability of aspartame in solutions is shown in Fig. 3. At 25°C, the maximum stability is observed at pH 4.3. Aspartame functions very well over a broad range of pH conditions but is most stable in the weak acidic range in which most foods exist—between pH 3 and 5. A frozen dairy dessert may have a pH ranging from 6.5 to more than 7.0, but, because of the frozen state, the rate of reaction is dramatically reduced. And, because of the lower free moisture, the shelf-life stability of aspartame exceeds the predicted shelf-life stability of these products. C. Solubility in Food and Beverage Applications Aspartame is slightly soluble in water (about 1.0% at 25°C) and is sparingly soluble in alcohol (10, 11). It is not soluble in fats or oils. An important consideration, especially for many products that are prepared by mixing aspartame-
Page 3 and 4: ISBN: 0-8247-0437-1 This book is pr
Page 5 and 6: iv Preface these sweeteners are bei
Page 7 and 8: vi Contents 7. Tagatose 105 Hans Be
Page 10 and 11: Contributors Sue E. Andress The Nut
Page 12 and 13: Contributors xi Carolyn M. Merkel M
Page 14 and 15: 1 Alternative Sweeteners: An Overvi
Page 16 and 17: Overview 3 II. RELATIVE SWEETNESS P
Page 18 and 19: Overview 5 IV. INTERNATIONAL REGULA
Page 20 and 21: Overview 7 V. U.S. REGULATION OF SW
Page 22 and 23: Overview 9 General recognition of s
Page 24 and 25: Overview 11 the maximum dietary lev
Page 26 and 27: 2 Acesulfame K Gert-Wolfhard von Ry
Page 28 and 29: Acesulfame K 15 Figure 3 Acesulfame
Page 30 and 31: Acesulfame K 17 Figure 4 Sweetness
Page 32 and 33: Acesulfame K 19 The acute oral toxi
Page 34 and 35: Acesulfame K 21 Table 2 Stability o
Page 36 and 37: Acesulfame K 23 were preferred over
Page 38 and 39: Acesulfame K 25 losses during bakin
Page 40 and 41: Acesulfame K 27 All methods describ
Page 42 and 43: Acesulfame K 29 24. Report of the S
Page 44 and 45: 3 Alitame Michael H. Auerbach Danis
Page 46 and 47: Alitame 33 IV. SOLUBILITY At the is
Page 48 and 49: Alitame 35 Figure 3 Alitame and asp
Page 50 and 51: Alitame 37 Figure 5 Metabolism of a
Page 52 and 53: Alitame 39 autonomic, gastrointesti
Page 56 and 57: Aspartame 43 Figure 2 Principal con
Page 58 and 59: Aspartame 45 A wide range exists ov
Page 60 and 61: Aspartame 47 Figure 4 Dietary intak
Page 62 and 63: Aspartame 49 day for 60-kg adults (
Page 64 and 65: Aspartame 51 mood, and behavior (88
Page 66 and 67: Aspartame 53 VI. WORLDWIDE REGULATO
Page 68 and 69: Aspartame 55 30. A Bar, C Biermann.
Page 70 and 71: Aspartame 57 67. HH Butchko, C Tsch
Page 72 and 73: Aspartame 59 104. AF Stokes, A Belg
Page 74: Aspartame 61 144. D Squillacote. As
Page 77 and 78: 64 Bopp and Price Figure 1 Structur
Page 79 and 80: 66 Bopp and Price Table 1 Regulator
Page 81 and 82: 68 Bopp and Price V. ADMIXTURE POTE
Page 83 and 84: 70 Bopp and Price and thickeners (1
Page 85 and 86: 72 Bopp and Price XII. METABOLISM C
Page 87 and 88: 74 Bopp and Price sodium cyclamate
Page 89 and 90: 76 Bopp and Price ied during the pa
Page 91 and 92: 78 Bopp and Price the studies invol
Page 93 and 94: 80 Bopp and Price 0.42 µg/ml and w
Page 95 and 96: 82 Bopp and Price 4. U.S. Patent No
Page 97 and 98: 84 Bopp and Price 48. SM Sieber, RH
Page 100 and 101: 6 Neohesperidin Dihydrochalcone Fra
Page 102 and 103: Neohesperidin Dihydrochalcone 89 Fi
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Neohesperidin Dihydrochalcone 91 Fi
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Neohesperidin Dihydrochalcone 93 in
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Neohesperidin Dihydrochalcone 95 ot
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Neohesperidin Dihydrochalcone 97 Ta
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Neohesperidin Dihydrochalcone 99 th
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Neohesperidin Dihydrochalcone 101 c
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Neohesperidin Dihydrochalcone 103 5
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7 Tagatose Hans Bertelsen and Søre
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Tagatose 107 the same type of Food
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Tagatose 109 in pigs according to m
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Tagatose 111 IV. USE OF D-TAGATOSE
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Tagatose 113 rinsing periods or dur
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Tagatose 115 anaerobic bacterial fe
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Tagatose 117 The intestines of both
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Tagatose 119 Table 1 Relative Sweet
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Tagatose 121 D. Hygroscopicity Taga
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Tagatose 123 Table 2 Heat of Soluti
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Tagatose 125 In conclusion, tagatos
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Tagatose 127 24. BB Jensen, B Buema
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130 Stargel et al. Figure 1 Compari
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132 Stargel et al. Figure 2 Matrix
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134 Stargel et al. ness of neotame
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136 Stargel et al. Figure 4 Taste p
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138 Stargel et al. Table 1 Solubili
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140 Stargel et al. study strains in
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142 Stargel et al. to 10,000 µg/pl
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144 Stargel et al. for general use
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9 Saccharin Ronald L. Pearson PMC S
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Saccharin 149 proved for use in the
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Saccharin 151 was added to sodium d
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Saccharin 153 Table 2 Economics of
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Saccharin 155 Table 4 Saccharin Adm
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Table 6 Flavor Profile and Cost Com
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Saccharin 159 Figure 5 Hydrolysis o
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Saccharin 161 malian repellant (52,
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Saccharin 163 REFERENCES 1. GE DuBo
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Saccharin 165 67. GP Schoenig, et a
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168 Kinghorn et al. herbarium speci
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170 Kinghorn et al. Figure 1 Struct
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172 Kinghorn et al. V. USE AND ADMI
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174 Kinghorn et al. sulting in the
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176 Kinghorn et al. Figure 2 Struct
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178 Kinghorn et al. iol administere
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180 Kinghorn et al. cus mutans, or
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182 Kinghorn et al. a natural sweet
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11 Sucralose Leslie A. Goldsmith an
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Sucralose 187 Figure 2 Sweeteness i
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Sucralose 189 cant difference was f
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Sucralose 191 fructose, and/or insu
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Sucralose 193 Figure 4 Sucralose so
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Sucralose 195 Figure 6 Viscosities
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Sucralose 197 Table 2 Sucralose Int
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Sucralose 199 tively, compared with
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Sucralose 201 Figure 10 Breakdown o
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Sucralose 203 Table 3 Percent Mass
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Sucralose 205 Table 4 Initial Appli
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Sucralose 207 4. Sucralose Safety A
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210 Kinghorn and Compadre establish
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212 Kinghorn and Compadre grosvenor
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214 Kinghorn and Compadre form. Phy
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216 Kinghorn and Compadre of the de
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218 Kinghorn and Compadre Figure 5
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226 Kinghorn and Compadre sweet tas
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230 Kinghorn and Compadre 5. O Tana
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232 Kinghorn and Compadre 41. S Nir
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13 Erythritol Milda E. Embuscado an
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Erythritol 237 The commercial produ
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Table 2 Properties of Erythritol Co
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Erythritol 241 used to obtain the d
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Erythritol 243 crose stabilized and
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Erythritol 245 Figure 4 (A) Rate of
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Table 6 Assessment Criteria for the
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Table 7 Summary of Pivotal Toxicity
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Erythritol 251 VI. FOOD AND PHARMAC
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Erythritol 253 5. C Servo, J Pabo,
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14 Hydrogenated Starch Hydrolysates
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Figure 1 (a) Chemical structures fo
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Hydrogenated Starch Hydrolysates an
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15 Isomalt Marie-Christel Wijers* P
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Isomalt 267 GPM depends on the isom
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Isomalt 269 IV. PHYSICO-CHEMICAL PR
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Isomalt 271 temperature than sucros
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Isomalt 273 C. Diabetics A number o
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Isomalt 275 Figure 7 Changes in wei
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Isomalt 277 C. Chewing Gum Sticks,
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Isomalt 279 isomalt is significantl
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Isomalt 281 der Sorbit-Toleranz ges
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16 Maltitol Kazuaki Kato Towa Chemi
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Maltitol 285 Like the other polyols
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Maltitol 287 of shape over time), h
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Maltitol 289 results of this confer
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Maltitol 291 available on certain p
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Maltitol 293 Table 3 Worldwide Stat
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Maltitol 295 alcohol. Unpublished r
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298 Mesters et al. Figure 1 The che
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300 Mesters et al. rium and equal m
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302 Mesters et al. sugars are then
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304 Mesters et al. Figure 2 Telemet
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306 Mesters et al. Figure 3 Moistur
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308 Mesters et al. Figure 6 Viscosi
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310 Mesters et al. tose are the mai
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312 Mesters et al. Figure 8 The wat
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314 Mesters et al. food containing
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18 Sorbitol and Mannitol Anh S. Le
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Sorbitol and Mannitol 319 Figure 2
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Table 1 Physical Properties of the
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Sorbitol and Mannitol 323 Figure 4
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Sorbitol and Mannitol 325 bases are
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Sorbitol and Mannitol 327 is used a
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Sorbitol and Mannitol 329 ‘‘cap
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Sorbitol and Mannitol 331 that mann
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Sorbitol and Mannitol 333 Mannitol
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19 Xylitol Philip M. Olinger Polyol
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Xylitol 337 Milled forms of xylitol
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Xylitol 339 Table 2 Solubility of S
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Xylitol 341 tol in a fluoride tooth
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Xylitol 343 The recognition of xyli
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Xylitol 345 tion of the availabilit
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Xylitol 347 grow and metabolize opt
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Xylitol 349 VIII. USE OF XYLITOL AS
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Xylitol 351 IX. USE OF XYLITOL IN P
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Xylitol 353 Human tolerance of high
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Xylitol 355 29. CS Gong, TA Claypoo
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Xylitol 357 71. JDB Featherstone, T
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Xylitol 359 112. JS Van der Hoeven.
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Xylitol 361 tans omz 176 by xylitol
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Xylitol 363 BL Horecker, K Lang, Y
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Xylitol 365 of Certain Food Additiv
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368 White and Osberger II. MANUFACT
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370 White and Osberger scribe impro
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372 White and Osberger Figure 1 Cyc
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374 White and Osberger When asparta
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376 White and Osberger Table 5 Temp
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378 White and Osberger Figure 3 Met
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380 White and Osberger Figure 5 Com
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382 White and Osberger Table 6 Glyc
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384 White and Osberger Table 8 Low-
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386 White and Osberger F. Confectio
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388 White and Osberger In 1993, Vui
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390 White and Osberger 18. AL Forbe
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392 Buck Table 1 Market Division be
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394 Buck Table 3 World HFS Consumpt
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396 Buck Figure 3 Production of 42%
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398 Buck Table 4 Typical Characteri
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400 Buck Table 5 Effect of Temperat
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402 Buck Table 7 International Soci
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404 Buck Because of the high purity
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406 Buck VII. APPLICATIONS HFCS rep
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408 Buck is a benefit and in other
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410 Buck 1986. This evaluation conc
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22 Isomaltulose William E. Irwin* P
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Isomaltulose 415 Figure 2 Isosweet
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Isomaltulose 417 Figure 3 Solubilit
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Isomaltulose 419 Figure 6 Plasma in
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Isomaltulose 421 6. Dreissig VW, Lu
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424 Richards and Dexter various pla
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426 Richards and Dexter from assays
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428 Richards and Dexter desiccation
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430 Richards and Dexter 2. Taste Qu
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432 Richards and Dexter parative da
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434 Richards and Dexter Table 3 Com
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436 Richards and Dexter dissipate t
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438 Richards and Dexter unpublished
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440 Richards and Dexter IX. SHELF-L
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Figure 7 Egg white (95 g) was mixed
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444 Richards and Dexter Figure 10 B
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446 Richards and Dexter Figure 12 O
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448 Richards and Dexter Figure 14 T
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450 Richards and Dexter XIII. CARIO
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452 Richards and Dexter tions was s
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454 Richards and Dexter activity, a
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456 Richards and Dexter E. 14-day T
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458 Richards and Dexter 3. J Leibow
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460 Richards and Dexter 41. LM Crow
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24 Mixed Sweetener Functionality Ab
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Mixed Sweetener Functionality 465 2
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Mixed Sweetener Functionality 467 T
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Mixed Sweetener Functionality 471 F
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Mixed Sweetener Functionality 479 I
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25 Aspartame-Acesulfame: Twinsweet
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Aspartame-Acesulfame: Twinsweet 483
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26 Polydextrose Helen Mitchell Dani
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Polydextrose 501 Table 1 Approximat
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Polydextrose 503 at 25°C. Polydext
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Polydextrose 505 Figure 4 Hygroscop
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Polydextrose 507 Table 5 Functional
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Polydextrose 509 F. Fiber Polydextr
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Polydextrose 511 providing bulk, mo
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Polydextrose 513 H. Soft Candy The
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Polydextrose 515 B. International T
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Polydextrose 517 chemical and econo
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520 Deis I. FAT IS ESSENTIAL AND FU
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522 Deis Figure 1 Ingredient suppor
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524 Deis binding water, thus provid
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526 Deis The U.S. Department of Agr
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528 Deis stabilizer, thickener, or
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530 Deis mouth feel and rate of gel
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532 Deis Figure 4 Structure of glyc
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534 Deis Table 4 General Categories
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536 Deis ninths of the fat availabl
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538 Deis the same function in all f
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540 Deis 28. Anon. Glycerine: like
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542 Index [Alitame] solubility, 33
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544 Index [Erythritol] gastrointest
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546 Index [High fructose corn syrup
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548 Index Mogrosides, 211-213 prope
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550 Index [Polyols] isomalt, 265-28
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552 Index [Sucralose] safety, 189-1
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