CA1052622A - Spray-dried l-aspartic acid derivatives - Google Patents
Spray-dried l-aspartic acid derivativesInfo
- Publication number
- CA1052622A CA1052622A CA220,842A CA220842A CA1052622A CA 1052622 A CA1052622 A CA 1052622A CA 220842 A CA220842 A CA 220842A CA 1052622 A CA1052622 A CA 1052622A
- Authority
- CA
- Canada
- Prior art keywords
- process according
- dispersion
- sweetening
- compound
- solids
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical class OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 title claims abstract 3
- CKLJMWTZIZZHCS-UWTATZPHSA-N L-Aspartic acid Natural products OC(=O)[C@H](N)CC(O)=O CKLJMWTZIZZHCS-UWTATZPHSA-N 0.000 claims abstract description 45
- 239000000203 mixture Substances 0.000 claims abstract description 35
- 239000002245 particle Substances 0.000 claims abstract description 33
- 150000001875 compounds Chemical class 0.000 claims abstract description 28
- 239000006185 dispersion Substances 0.000 claims abstract description 28
- 238000001035 drying Methods 0.000 claims abstract description 19
- 239000008393 encapsulating agent Substances 0.000 claims abstract description 17
- 150000002148 esters Chemical class 0.000 claims abstract description 17
- 229960005261 aspartic acid Drugs 0.000 claims abstract description 15
- CKLJMWTZIZZHCS-UHFFFAOYSA-N D-OH-Asp Natural products OC(=O)C(N)CC(O)=O CKLJMWTZIZZHCS-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000007787 solid Substances 0.000 claims description 39
- 238000000034 method Methods 0.000 claims description 28
- 239000002002 slurry Substances 0.000 claims description 26
- 230000008569 process Effects 0.000 claims description 22
- 239000000463 material Substances 0.000 claims description 17
- 229920001353 Dextrin Polymers 0.000 claims description 16
- 239000004375 Dextrin Substances 0.000 claims description 16
- 108010016626 Dipeptides Proteins 0.000 claims description 16
- 235000019425 dextrin Nutrition 0.000 claims description 16
- 239000000243 solution Substances 0.000 claims description 15
- 238000012545 processing Methods 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 9
- 125000005907 alkyl ester group Chemical group 0.000 claims description 7
- 235000009508 confectionery Nutrition 0.000 claims description 6
- 239000007921 spray Substances 0.000 claims description 6
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 239000008121 dextrose Substances 0.000 claims description 3
- 230000000694 effects Effects 0.000 claims description 3
- 229960005190 phenylalanine Drugs 0.000 claims description 3
- 239000012798 spherical particle Substances 0.000 claims description 3
- 239000012736 aqueous medium Substances 0.000 claims description 2
- 150000004702 methyl esters Chemical class 0.000 claims description 2
- 229920001542 oligosaccharide Polymers 0.000 claims description 2
- 150000002482 oligosaccharides Chemical class 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 14
- 239000013078 crystal Substances 0.000 abstract description 9
- 238000001694 spray drying Methods 0.000 abstract description 6
- IAOZJIPTCAWIRG-QWRGUYRKSA-N aspartame Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 IAOZJIPTCAWIRG-QWRGUYRKSA-N 0.000 description 16
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 16
- 235000003599 food sweetener Nutrition 0.000 description 10
- 238000004806 packaging method and process Methods 0.000 description 10
- 239000003765 sweetening agent Substances 0.000 description 10
- 235000013305 food Nutrition 0.000 description 7
- -1 L-aspartic acid ester Chemical class 0.000 description 6
- 235000013361 beverage Nutrition 0.000 description 6
- 235000003704 aspartic acid Nutrition 0.000 description 5
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 5
- 238000009826 distribution Methods 0.000 description 5
- 239000000834 fixative Substances 0.000 description 5
- 238000003860 storage Methods 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 235000007983 food acid Nutrition 0.000 description 4
- 240000008042 Zea mays Species 0.000 description 3
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 3
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 3
- 229940024606 amino acid Drugs 0.000 description 3
- 230000015556 catabolic process Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 235000005822 corn Nutrition 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
- 230000018044 dehydration Effects 0.000 description 3
- 238000006297 dehydration reaction Methods 0.000 description 3
- 230000009969 flowable effect Effects 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- 230000004224 protection Effects 0.000 description 3
- 239000006188 syrup Substances 0.000 description 3
- 235000020357 syrup Nutrition 0.000 description 3
- YZQCXOFQZKCETR-RGURZIINSA-N (3s)-3-amino-4-[(1-carboxy-2-phenylethyl)amino]-4-oxobutanoic acid Chemical compound OC(=O)C[C@H](N)C(=O)NC(C(O)=O)CC1=CC=CC=C1 YZQCXOFQZKCETR-RGURZIINSA-N 0.000 description 2
- YZQCXOFQZKCETR-UWVGGRQHSA-N Asp-Phe Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C(O)=O)CC1=CC=CC=C1 YZQCXOFQZKCETR-UWVGGRQHSA-N 0.000 description 2
- LCPYQJIKPJDLLB-UWVGGRQHSA-N Leu-Leu Chemical compound CC(C)C[C@H](N)C(=O)N[C@H](C(O)=O)CC(C)C LCPYQJIKPJDLLB-UWVGGRQHSA-N 0.000 description 2
- 239000005913 Maltodextrin Substances 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 235000001014 amino acid Nutrition 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 239000008122 artificial sweetener Substances 0.000 description 2
- 235000021311 artificial sweeteners Nutrition 0.000 description 2
- 150000001509 aspartic acid derivatives Chemical class 0.000 description 2
- YZQCXOFQZKCETR-UHFFFAOYSA-N aspartyl-phenylalanine Chemical compound OC(=O)CC(N)C(=O)NC(C(O)=O)CC1=CC=CC=C1 YZQCXOFQZKCETR-UHFFFAOYSA-N 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000084 colloidal system Substances 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 238000005538 encapsulation Methods 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 235000019634 flavors Nutrition 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 229940035034 maltodextrin Drugs 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 229960004793 sucrose Drugs 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- YLJJIBQVVPBSNK-WPRPVWTQSA-N (3s)-3-amino-4-[[(1s)-1-carboxyethyl]-cyclohexylamino]-4-oxobutanoic acid Chemical class OC(=O)C[C@H](N)C(=O)N([C@@H](C)C(O)=O)C1CCCCC1 YLJJIBQVVPBSNK-WPRPVWTQSA-N 0.000 description 1
- UBLAMKHIFZBBSS-UHFFFAOYSA-N 3-Methylbutyl pentanoate Chemical compound CCCCC(=O)OCCC(C)C UBLAMKHIFZBBSS-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241000206575 Chondrus crispus Species 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 229920002245 Dextrose equivalent Polymers 0.000 description 1
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 125000000570 L-alpha-aspartyl group Chemical group [H]OC(=O)C([H])([H])[C@]([H])(N([H])[H])C(*)=O 0.000 description 1
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 239000005862 Whey Substances 0.000 description 1
- 102000007544 Whey Proteins Human genes 0.000 description 1
- 108010046377 Whey Proteins Proteins 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000000337 buffer salt Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000002301 combined effect Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical class OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
- 238000009795 derivation Methods 0.000 description 1
- 235000021185 dessert Nutrition 0.000 description 1
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical class [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000001493 electron microscopy Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 235000010944 ethyl methyl cellulose Nutrition 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012527 feed solution Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 229920003087 methylethyl cellulose Polymers 0.000 description 1
- 238000000386 microscopy Methods 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 235000019691 monocalcium phosphate Nutrition 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 238000010951 particle size reduction Methods 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000002633 protecting effect Effects 0.000 description 1
- 239000003531 protein hydrolysate Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000010079 rubber tapping Methods 0.000 description 1
- 238000005204 segregation Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000019605 sweet taste sensations Nutrition 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 238000001238 wet grinding Methods 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/30—Artificial sweetening agents
- A23L27/31—Artificial sweetening agents containing amino acids, nucleotides, peptides or derivatives
- A23L27/32—Artificial sweetening agents containing amino acids, nucleotides, peptides or derivatives containing dipeptides or derivatives
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Health & Medical Sciences (AREA)
- Nutrition Science (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Seasonings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/448,845 US3962468A (en) | 1974-03-07 | 1974-03-07 | Spray-dried L-aspartic acid derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1052622A true CA1052622A (en) | 1979-04-17 |
Family
ID=23781898
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA220,842A Expired CA1052622A (en) | 1974-03-07 | 1975-02-26 | Spray-dried l-aspartic acid derivatives |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3962468A (en, 2012) |
| JP (1) | JPS5758148B2 (en, 2012) |
| CA (1) | CA1052622A (en, 2012) |
| CH (1) | CH603073A5 (en, 2012) |
| DE (1) | DE2509257C2 (en, 2012) |
| FR (1) | FR2262922B1 (en, 2012) |
| GB (1) | GB1478947A (en, 2012) |
| IT (1) | IT1033489B (en, 2012) |
| NL (1) | NL7502646A (en, 2012) |
| SE (1) | SE403556B (en, 2012) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1057568A (en) * | 1974-06-10 | 1979-07-03 | General Foods Corporation | Soluble sweetening composition and method |
| US4079151A (en) * | 1975-05-29 | 1978-03-14 | General Foods Corporation | Frosted coating for sweetened foods |
| IE44797B1 (en) * | 1976-04-05 | 1982-04-07 | Gen Foods Corp | Sweetening composition and method for the preparation thereof |
| EP0014554A1 (en) * | 1979-02-06 | 1980-08-20 | TATE & LYLE PATENT HOLDINGS LIMITED | Sweetening compositions containing peptide sweeteners and a method for their manufacture |
| WO1980002364A1 (en) * | 1979-04-26 | 1980-11-13 | Alberta Gas Chem Inc | Cold water soluble fumaric acid |
| US4465694A (en) * | 1980-12-10 | 1984-08-14 | Ajinomoto Company, Incorporated | Dipeptide sweetening composition |
| US4384004A (en) * | 1981-06-02 | 1983-05-17 | Warner-Lambert Company | Encapsulated APM and method of preparation |
| CA1206370A (en) * | 1982-08-17 | 1986-06-24 | Ajinomoto Co., Inc. | Stabilized aspartame compositions |
| ES8406855A1 (es) * | 1982-10-25 | 1984-08-16 | Gen Foods Corp | Un metodo para fijar aspartama sobre un sustrato comestible |
| JPH0631312B2 (ja) * | 1983-03-18 | 1994-04-27 | 味の素株式会社 | ジペプチド結晶及びその製造方法 |
| DE3370751D1 (en) * | 1983-08-12 | 1987-05-14 | Nabisco Brands Inc | Process for incorporating aspartame into extruded products |
| WO1985001862A1 (en) * | 1983-11-04 | 1985-05-09 | General Foods Corporation | Sweetener composition, process for making the same, and comestibles comprising said sweetener composition |
| IE58110B1 (en) * | 1984-10-30 | 1993-07-14 | Elan Corp Plc | Controlled release powder and process for its preparation |
| JPH0653051B2 (ja) * | 1985-04-22 | 1994-07-20 | アリメント工業株式会社 | 低カロリ−軟カプセル剤 |
| US4634792A (en) * | 1985-05-06 | 1987-01-06 | General Foods Corporation | L-aminodicarboxylic acid aminoalkenoic acid ester amides |
| US5217735A (en) * | 1986-10-22 | 1993-06-08 | Wm. Wrigley Jr. Company | Method of making chewing gum with delayed release ingredients |
| US5221543A (en) * | 1986-10-22 | 1993-06-22 | Firma Wilhelm Fette Gmbh | Method of making a fast release stabilized aspartame ingredient for chewing gum |
| US4863745A (en) * | 1986-10-22 | 1989-09-05 | Wm. Wrigley Jr. Company | Chewing gum containing zein coated high-potency sweetener and method |
| JPS63160458U (en, 2012) * | 1987-04-09 | 1988-10-20 | ||
| AU600176B2 (en) * | 1987-10-13 | 1990-08-02 | Mitsui Toatsu Chemicals Inc. | Preparation method of alpha-l-aspartyl-l-phenylalanine methyl ester having improved solubilization |
| US4919941A (en) * | 1987-12-18 | 1990-04-24 | Wm. Wrigley Jr. Company | Chewing gum containing delayed release protein sweetener and method |
| US4885175A (en) * | 1987-12-23 | 1989-12-05 | Wm. Wrigley Jr. Company | Method of making chewing gum with wax-coated delayed release ingredients |
| US5085876A (en) * | 1988-11-16 | 1992-02-04 | The Nutrasweet Company | Fast dissolving sweetening agent including caramel |
| US4931295A (en) * | 1988-12-02 | 1990-06-05 | Wm. Wrigley Jr. Company | Chewing gum containing high-potency sweetener particles with modified zein coating |
| US4988518A (en) * | 1989-12-28 | 1991-01-29 | Wm. Wrigley Jr. Company | Chewing gum with liquid flavor added to the rolling compound and method |
| MX9102619A (es) * | 1990-12-17 | 1992-06-01 | Redding Bruce K | Metodo y aparato para revestir materiales. |
| AU639772B2 (en) * | 1991-03-06 | 1993-08-05 | Nutrasweet Company, The | Fast dissolving sweetening agent including caramel |
| DK0533681T3 (da) * | 1991-03-06 | 1996-07-29 | Nutrasweet Co | Hurtigopløsende sødemiddel omfattende karamel |
| EP0687147A4 (en) * | 1993-12-07 | 1996-02-28 | Nutrasweet Co | STABLE PARTICULATE SWEETER COMPOSITIONS |
| US7258885B2 (en) * | 2004-03-01 | 2007-08-21 | Tasty-Trim, Inc. | Flavored artificial sweetener |
| EP2813220A3 (en) | 2010-04-09 | 2015-06-17 | Pacira Pharmaceuticals, Inc. | Method for formulating large diameter synthetic membrane vesicles |
| WO2018135363A1 (ja) * | 2017-01-20 | 2018-07-26 | ニュートリー株式会社 | 高分散性デキストリン及びその製造方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3761288A (en) * | 1970-07-16 | 1973-09-25 | Gen Foods Corp | Method for making a low calorie sweetening composition |
| US3753739A (en) * | 1970-11-05 | 1973-08-21 | Alberto Culver Co | Low calorie dry sweetener composition |
-
1974
- 1974-03-07 US US05/448,845 patent/US3962468A/en not_active Expired - Lifetime
-
1975
- 1975-02-25 GB GB7854/75A patent/GB1478947A/en not_active Expired
- 1975-02-26 CA CA220,842A patent/CA1052622A/en not_active Expired
- 1975-03-04 DE DE2509257A patent/DE2509257C2/de not_active Expired
- 1975-03-06 NL NL7502646A patent/NL7502646A/xx not_active Application Discontinuation
- 1975-03-06 IT IT21009/75A patent/IT1033489B/it active
- 1975-03-06 SE SE7502534A patent/SE403556B/xx unknown
- 1975-03-07 JP JP50027916A patent/JPS5758148B2/ja not_active Expired
- 1975-03-07 FR FR7507282A patent/FR2262922B1/fr not_active Expired
- 1975-03-07 CH CH295075A patent/CH603073A5/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2262922A1 (en, 2012) | 1975-10-03 |
| NL7502646A (nl) | 1975-09-09 |
| DE2509257C2 (de) | 1984-07-19 |
| SE403556B (sv) | 1978-08-28 |
| SE7502534L (en, 2012) | 1975-09-08 |
| IT1033489B (it) | 1979-07-10 |
| AU7874575A (en) | 1976-09-09 |
| DE2509257A1 (de) | 1975-09-11 |
| US3962468A (en) | 1976-06-08 |
| FR2262922B1 (en, 2012) | 1978-12-29 |
| JPS50160463A (en, 2012) | 1975-12-25 |
| CH603073A5 (en, 2012) | 1978-08-15 |
| JPS5758148B2 (en, 2012) | 1982-12-08 |
| GB1478947A (en) | 1977-07-06 |
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