Title: Alternative Sweeteners

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Saccharin 151 was added to sodium disulfide; the product was collected, washed, and dried. The disulfide was then esterified by treatment with methanol in sulfuric acid and oxidized with gaseous chlorine to ortho-carbomethoxybenzenesulfonyl chloride. Amidation with excess ammonia yielded ammonium saccharin, and neutralization with sulfuric acid produced insoluble acid saccharin (12). Today, the Maumee process has evolved into an efficient continuous process (Fig. 3). Methyl anthranilate is diazotized to form 2-carbomethoxybenzenediazonium chloride. Sulfonation followed by oxidation yields 2-carbomethoxybenzenesulfonyl chloride. Again, amidation of this sulfonylchloride, followed by acidification, forms insoluble acid saccharin. Subsequent addition of sodium hydroxide or calcium hydroxide produces the soluble sodium and calcium forms, respectively (13). IV. PROPERTIES Acid saccharin exists as a white odorless, crystalline powder. It is a moderately strong acid, with only slight solubility in water. However, its intense sweetness allows even slight aqueous solubility to be quite sufficient for all sweetener applications. There are three commercially available saccharin forms: (a) acid, (b) sodium, and (c) calcium. Sodium saccharin is the most commonly used form because of its high solubility, high stability, and superior economics. All are Table 1 Properties of Saccharin Forms Acid saccharin Sodium saccharin Calcium saccharin Molecular formula C 7H 5NO 3S C 7H 4NO 3SNa⋅2H 2O [C 7H 4NO 3S] 2Ca⋅2H 2O Molecular weight 183.18 241.20 440.48 C.A.S. Registry No. 81-07-2 128-44-9 6485-34-3 Melting point (°C) 228–229 300 300 Appearance White solid White solid White solid pKa a 1.30 — — Solubility (g/100 g water) at: b 20°C 0.2 100 37 35°C 0.4 143 82 50°C 0.7 187 127 75°C 1.3 254 202 90°C — 297 247 a From Ref. 15. b From Refs. 16, 44.
152 Pearson manufactured to meet Food Chemicals Codex and U.S. Pharmacopeia/National Formulary specifications (14a,b). Their properties are listed in Table 1. Several additional salts of saccharin have been reported. These include silver, ammonium, cupric, lithium, magnesium, zinc, and potassium. Although all of these are intensely sweet, none is available commercially. Substitutions on the nitrogen of saccharin eliminates its sweetness, whereas carbon substitution gives unpredictable sweetness results (17a,b), although no substituent imparts a greater sweetness than that of saccharin itself (18). X-ray crystallography has shown that the acid form of saccharin exists as dimers formed by hydrogen bonding between the imide hydrogen and the keto oxygen (19a,b). V. SWEETENING POWER AND ADMIXTURE POTENTIAL Saccharin is approximately 300 times as sweet as sugar dissolved in water at 7 wt% concentration. Coupled with sodium saccharin’s low price (approximately $3.00/lb), this sweetening factor means that a penny’s worth of saccharin has the sweetening power of 1 pound of sugar. The relative economics of current commercial sweeteners are compared in Table 2, showing that all the saccharin forms are by far the least expensive per sweetness equivalent. In 1921, Paul observed that saccharin’s sweetening power relative to sucrose increases with decreasing concentration (20). Recent data were used in Fig. 4, which again demonstrates the dramatic increase in sweetening potency, relative to sucrose, with decreasing sweetener concentration (1). He found a similar concentration effect with dulcin, another alternative sweetener used at the time, but that is no longer approved. Paul made the remarkable observation that when these two sweeteners are blended, each sweetener retains its higher sweetening power in the presence of the other. For example, to achieve a sweetness equal to a 9% sucrose solution, individually 450 mg/l of saccharin or 1250 mg/l of dulcin is required. But this 9% sucrose solution is also equaled with a blend containing 190 mg/l of saccharin plus 120 mg/l of dulcin, only 310 mg/l in total. Individually, the 190 mg/l of saccharin is equivalent to a 6% sucrose solution, whereas the 120 mg/l of dulcin is equivalent to a 3% sucrose solution. Thus by blending the two sweeteners, Paul was able to ‘‘add’’ their individual sweetening equivalencies and achieve the same sweetness with less total sweetener. This effect is more completely demonstrated by Paul’s data presented in Table 3. Today, this phenomenon of increasing sweetening power with decreasing concentration has been established for many sweeteners (21, 22), and additive effects have been reported for blends of saccharin with several other sweeteners. In addition, the blend is frequently sweeter than would be predicted by the additive effect. This enhanced effect is termed ‘‘synergistic.’’ Table 4 lists various
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ISBN: 0-8247-0437-1 This book is pr
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iv Preface these sweeteners are bei
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vi Contents 7. Tagatose 105 Hans Be
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Contributors Sue E. Andress The Nut
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Contributors xi Carolyn M. Merkel M
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1 Alternative Sweeteners: An Overvi
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Overview 3 II. RELATIVE SWEETNESS P
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Overview 5 IV. INTERNATIONAL REGULA
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Overview 7 V. U.S. REGULATION OF SW
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Overview 9 General recognition of s
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Overview 11 the maximum dietary lev
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2 Acesulfame K Gert-Wolfhard von Ry
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Acesulfame K 15 Figure 3 Acesulfame
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Acesulfame K 17 Figure 4 Sweetness
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Acesulfame K 19 The acute oral toxi
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Acesulfame K 21 Table 2 Stability o
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Acesulfame K 23 were preferred over
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Acesulfame K 25 losses during bakin
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Acesulfame K 27 All methods describ
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Acesulfame K 29 24. Report of the S
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3 Alitame Michael H. Auerbach Danis
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Alitame 33 IV. SOLUBILITY At the is
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Alitame 35 Figure 3 Alitame and asp
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Alitame 37 Figure 5 Metabolism of a
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Alitame 39 autonomic, gastrointesti
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4 Aspartame Harriett H. Butchko, W.
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Aspartame 43 Figure 2 Principal con
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Aspartame 45 A wide range exists ov
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Aspartame 47 Figure 4 Dietary intak
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Aspartame 49 day for 60-kg adults (
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Aspartame 51 mood, and behavior (88
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Aspartame 53 VI. WORLDWIDE REGULATO
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Aspartame 55 30. A Bar, C Biermann.
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Aspartame 57 67. HH Butchko, C Tsch
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Aspartame 59 104. AF Stokes, A Belg
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Aspartame 61 144. D Squillacote. As
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64 Bopp and Price Figure 1 Structur
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66 Bopp and Price Table 1 Regulator
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68 Bopp and Price V. ADMIXTURE POTE
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70 Bopp and Price and thickeners (1
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72 Bopp and Price XII. METABOLISM C
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74 Bopp and Price sodium cyclamate
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76 Bopp and Price ied during the pa
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78 Bopp and Price the studies invol
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80 Bopp and Price 0.42 µg/ml and w
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82 Bopp and Price 4. U.S. Patent No
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84 Bopp and Price 48. SM Sieber, RH
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6 Neohesperidin Dihydrochalcone Fra
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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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Page 118 and 119: 7 Tagatose Hans Bertelsen and Søre
Page 120 and 121: Tagatose 107 the same type of Food
Page 122 and 123: Tagatose 109 in pigs according to m
Page 124 and 125: Tagatose 111 IV. USE OF D-TAGATOSE
Page 126 and 127: Tagatose 113 rinsing periods or dur
Page 128 and 129: Tagatose 115 anaerobic bacterial fe
Page 130 and 131: Tagatose 117 The intestines of both
Page 132 and 133: Tagatose 119 Table 1 Relative Sweet
Page 134 and 135: Tagatose 121 D. Hygroscopicity Taga
Page 136 and 137: Tagatose 123 Table 2 Heat of Soluti
Page 138 and 139: Tagatose 125 In conclusion, tagatos
Page 140: Tagatose 127 24. BB Jensen, B Buema
Page 143 and 144: 130 Stargel et al. Figure 1 Compari
Page 145 and 146: 132 Stargel et al. Figure 2 Matrix
Page 147 and 148: 134 Stargel et al. ness of neotame
Page 149 and 150: 136 Stargel et al. Figure 4 Taste p
Page 151 and 152: 138 Stargel et al. Table 1 Solubili
Page 153 and 154: 140 Stargel et al. study strains in
Page 155 and 156: 142 Stargel et al. to 10,000 µg/pl
Page 157 and 158: 144 Stargel et al. for general use
Page 160 and 161: 9 Saccharin Ronald L. Pearson PMC S
Page 162 and 163: Saccharin 149 proved for use in the
Page 166 and 167: Saccharin 153 Table 2 Economics of
Page 168 and 169: Saccharin 155 Table 4 Saccharin Adm
Page 170 and 171: Table 6 Flavor Profile and Cost Com
Page 172 and 173: Saccharin 159 Figure 5 Hydrolysis o
Page 174 and 175: Saccharin 161 malian repellant (52,
Page 176 and 177: Saccharin 163 REFERENCES 1. GE DuBo
Page 178: Saccharin 165 67. GP Schoenig, et a
Page 181 and 182: 168 Kinghorn et al. herbarium speci
Page 183 and 184: 170 Kinghorn et al. Figure 1 Struct
Page 185 and 186: 172 Kinghorn et al. V. USE AND ADMI
Page 187 and 188: 174 Kinghorn et al. sulting in the
Page 189 and 190: 176 Kinghorn et al. Figure 2 Struct
Page 191 and 192: 178 Kinghorn et al. iol administere
Page 193 and 194: 180 Kinghorn et al. cus mutans, or
Page 195 and 196: 182 Kinghorn et al. a natural sweet
Page 198 and 199: 11 Sucralose Leslie A. Goldsmith an
Page 200 and 201: Sucralose 187 Figure 2 Sweeteness i
Page 202 and 203: Sucralose 189 cant difference was f
Page 204 and 205: Sucralose 191 fructose, and/or insu
Page 206 and 207: Sucralose 193 Figure 4 Sucralose so
Page 208 and 209: Sucralose 195 Figure 6 Viscosities
Page 210 and 211: Sucralose 197 Table 2 Sucralose Int
Page 212 and 213: 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
Page 555 and 556:
542 Index [Alitame] solubility, 33
Page 557 and 558:
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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