Title: Alternative Sweeteners

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Neohesperidin Dihydrochalcone 103 55. RM Horowitz, B Gentili. Dihydrochalcone xylosides and their use as sweetening agents. US Patent No. 3,826,856 (July 30, 1974). 56. GP Rizzi. Dihydrochalcone sweetening agents. US Patent No. 3,739,064 (June 12, 1973). 57. F Caccia, R Dispenza, G Fonza, C Fuganti, L Malpezzi, A Mele. Structure of neohesperidin dihydrochalcone/β-cyclodextrin inclusion complex: NMR, MS, and X-ray spectroscopy investigation. J Agric Food Chem 46:1500–1505, 1998. 58. GW von Rymon Lipinsky, E Lück. Sweetener mixture. US Patent No. 4,158,068 (1979). 59. MR Jenner. Sweetening agents. Eur Patent Application No. 0 507 598 A1 (1992). 60. HJ Chung. Measurement of synergistic effects of binary sweetener mixtures. J Food Sci Nutr 2:291–295, 1997. 61. MG Lindley, PK Beyts, I Canales, F Borrego. Flavor modifying characteristics of the intense sweetener neohesperidin dihydrochalcone. J Food Sci 58:592–594666, 1993. 62. MG Lindley. Neohesperidin dihydrochalcone: Recent findings and technical advances. In: TH Grenby, ed. Advances in Sweeteners. Glasgow, UK: Chapman & Hall, 1996, pp 240–252. 63. R Foguet, A Cisteró, F Borrego. Body and mouthfeel potentiated foods and beverages containing neohesperidin dihydrochalcone. US Patent No. 5,300,309 (1994). 64. R Foguet, A Cisteró, F Borrego. Use of neohesperidin dihydrochalcone for potentiating body and mouthfeel of foods and beverages. Eur Patent Specification No. 0 500 977 B1 (1995). 65. L Engels, G Stagnitti. Flavor modifying composition. WO Patent No. 96/17527 (1996). 66. F Borrego, H Montijano. Anwendungsmöglichkeiten des Süssstoffs Neohesperidin Dihydrochalkon in Arneimitteln. Pharm Ind 57:880–882, 1995. 67. MA Bruna, RJ Miralles, JA Poch, FL Redondo. Compositions for alkalinizing and energy-boosting drinks. WO Patent No. 96/03059 (Feb. 8, 1996). 68. R Foguet, F Borrego, J Campos, JA Madrid, S Zamora. New feed for cultured fish. Eur Patent Application No. 0 655 203 A1. 69. MR Gumbmann, DH Gould, DJ Robbins, AN Booth. Toxicity studies of neohesperidin dihydrochalcone. In: JH Shaw, GG Roussos, eds. Proceedings, Sweeteners and Dental Caries. Washington, DC: Information Retrieval, 1978, pp 301–310. 70. RP Batzinger, SYL Ou, E Bueding. Saccharin and other sweeteners: Mutagenic properties. Science 198:944–946, 1977. 71. JP Brown, PS Dietrich, RJ Brown. Frameshift mutagenicity of certain naturally occurring phenolic compounds in the Salmonella/microsome test: Activation of anthraquinone and flavonol glycosides by gut bacterial enzymes. Biochem Soc Trans 5: 1489–1492, 1977. 72. JT MacGregor, L Jurd. Mutagenicity of plant flavonoids: Structural requirements for mutagenic activity in Salmonella typhimurium. Mutation Res 54:297–309, 1978. 73. JB Brown, PS Dietrich. Mutagenicity of plant flavonols in the Salmonella/mammalian microsome test: Activation of flavonol glycosides by mixed glycosidases from rat cecal bacteria and other sources. Mutation Res 66:223–240, 1979.
104 Borrego and Montijano 74. JT MacGregor. Mutagenicity studies of flavonoids in vivo and in vitro. Toxicol Appl Pharmacol 48:A47, 1979. 75. BAR Lina, HC Dreef-van der Meulen, DC Leegwater. Subchronic (13 wk) oral toxicity of neohesperidin dihydrochalcone in rats. Food Chem Toxicol 28:507–513, 1990. 76. Report of the Scientific Committee for Food on Sweeteners. Commission of the European Communities (CS/EDUL/-Final), December 11, 1987. 77. J Kuhnau. The flavonoids. A class of semiessential food components: Their role in human nutrition. World Rev Nutr Diet 24:117–191, 1976. 78. F DeEds. Flavonoids metabolism. Compr Biochem 125:417–423, 1971. 79. CW Berry, CA Henry. Baylor College of Dentistry, Meeting of the American Association for Dental Research, as reported in Food Chemical News, March 21, 1983, p 25. 80. European Parliament and Council Directive 94/35/EC of 30 June 1994 on sweeteners for use in foodstuffs. Off J Eur Comm (10.9.94) No. L237/3. 81. Directive 96/83/EC of the European Parliament and of the Council of 19 December 1996. Off J Eur Comm (19.2.97) No. L 48/16. 82. European Parliament and Council Directive 95/2/EC of 20 February 1995 on food additives other than colours and sweeteners. Off J Eur Comm (18.3.5) No. L61/1. 83. RL Smith, P Newberne, TB Adams, RA Ford, JB Hallagan. GRAS flavoring substances 17. The 17th publication by the Flavors and Extract Manufacturers’ Association’s Expert Panel on recent progress in the consideration of flavoring ingredients generally recognized as safe under the Food Additives Amendment. Food Technol 50:72–81, 1996. 84. MR Castellar, JL Iborra, I Canales. Analysis of commercial neohesperidin dihydrochalcone by high performance liquid chromatography. J Liq Chrom Rel Technol 20:2063–2073, 1997. 85. M Hausch. Simultaneous determination of neohesperidin dihydrochalcone and other sweetening agents by HPLC. Lebensmittelchemie 50:31–32, 1996. 86. R Schwarzenbach. Liquid chromatography of neohesperidin dihydrochalcone. J Chromatogr 129:31–39, 1996. 87. JF Fisher. A high-pressure liquid chromatographic method for the quantitation of neohesperidin dihydrochalcone. J Agric Food Chem 25:682–683, 1976. 88. JF Fisher. Review of quantitative analyses for limonin, naringin, naringenin rutinoside, hesperidin and neohesperidin dihydrochalcone in citrus juice by high performance liquid chromatography. Proc Int Soc Citric 3:813–816, 1976. 89. H Montijano, F Borrego, I Canales, FA Tomás-Barberán. Validated high-performance liquid chromatographic method for quantitation of neohesperidin dihydrochalcone in foods. J Chromatogr A 758:163–166, 1997.
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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
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
Page 104 and 105: Neohesperidin Dihydrochalcone 91 Fi
Page 106 and 107: Neohesperidin Dihydrochalcone 93 in
Page 108 and 109: Neohesperidin Dihydrochalcone 95 ot
Page 110 and 111: Neohesperidin Dihydrochalcone 97 Ta
Page 112 and 113: Neohesperidin Dihydrochalcone 99 th
Page 114 and 115: Neohesperidin Dihydrochalcone 101 c
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 164 and 165: 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
Page 453 and 454:
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
Page 535 and 536:
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
Page 543 and 544:
530 Deis mouth feel and rate of gel
Page 545 and 546:
532 Deis Figure 4 Structure of glyc
Page 547 and 548:
534 Deis Table 4 General Categories
Page 549 and 550:
536 Deis ninths of the fat availabl
Page 551 and 552:
538 Deis the same function in all f
Page 553 and 554:
540 Deis 28. Anon. Glycerine: like
Page 555 and 556:
542 Index [Alitame] solubility, 33
Page 557 and 558:
544 Index [Erythritol] gastrointest
Page 559 and 560:
546 Index [High fructose corn syrup
Page 561 and 562:
548 Index Mogrosides, 211-213 prope
Page 563 and 564:
550 Index [Polyols] isomalt, 265-28
Page 565 and 566:
552 Index [Sucralose] safety, 189-1
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Title: Alternative Sweeteners

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