CA1076110A - Sweeteners - Google Patents

Sweeteners

Info

Publication number: CA1076110A
Authority: CA; Canada
Prior art keywords: chloro; compound; deoxy; sucrose; dichloro
Prior art date: 1976-01-08
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

Application number

CA268,863A

Other languages

English (en)

French (fr)

Inventor

Leslie Hough

Michael R. Jenner

Shashikant P. Phadnis

Riaz A. Khan

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Tate and Lyle PLC

Original Assignee

Tate and Lyle PLC

Priority date (The priority date 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 date listed.)

1976-01-08

Filing date

1976-12-29

Publication date

1980-04-22

1976-12-29 Application filed by Tate and Lyle PLC filed Critical Tate and Lyle PLC

1979-06-20 Priority to CA330,179A priority Critical patent/CA1096233A/en

1980-04-22 Application granted granted Critical

1980-04-22 Publication of CA1076110A publication Critical patent/CA1076110A/en

Status Expired legal-status Critical Current

Links

235000003599 food sweetener Nutrition 0.000 title description 16
239000003765 sweetening agent Substances 0.000 title description 16
150000001875 compounds Chemical class 0.000 claims abstract description 30
239000005720 sucrose Substances 0.000 claims abstract description 28
125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 22
239000000203 mixture Substances 0.000 claims abstract description 21
238000000034 method Methods 0.000 claims abstract description 13
235000013361 beverage Nutrition 0.000 claims abstract description 6
239000000126 substance Substances 0.000 claims abstract description 5
229910052801 chlorine Chemical group 0.000 claims description 13
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
125000001424 substituent group Chemical group 0.000 claims description 5
BPQOIESVQZIMHQ-UGDNZRGBSA-N (2r,3r,4s,5s,6s)-2-[(2r,3s,4s,5s)-2,5-bis(chloromethyl)-3,4-dihydroxyoxolan-2-yl]oxy-6-(chloromethyl)oxane-3,4,5-triol Chemical compound O[C@H]1[C@H](O)[C@@H](CCl)O[C@@]1(CCl)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CCl)O1 BPQOIESVQZIMHQ-UGDNZRGBSA-N 0.000 claims description 4
239000004606 Fillers/Extenders Substances 0.000 claims description 4
239000000654 additive Substances 0.000 claims description 3
230000000996 additive effect Effects 0.000 claims description 3
239000007788 liquid Substances 0.000 claims description 3
239000001814 pectin Substances 0.000 claims description 3
235000010987 pectin Nutrition 0.000 claims description 3
229920001277 pectin Polymers 0.000 claims description 3
239000007787 solid Substances 0.000 claims description 3
UQXZSKHOYOHVIH-UGDNZRGBSA-N (2R,3R,4S,5S,6R)-2-[(2R,3S,4S,5S)-2,5-bis(chloromethyl)-3,4-dihydroxyoxolan-2-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@]1(CCl)[C@@H](O)[C@H](O)[C@@H](CCl)O1 UQXZSKHOYOHVIH-UGDNZRGBSA-N 0.000 claims description 2
229920001938 Vegetable gum Polymers 0.000 claims description 2
239000002671 adjuvant Substances 0.000 claims description 2
239000008187 granular material Substances 0.000 claims description 2
FESWLBKGLROKRB-UGDNZRGBSA-N (2R,3R,4S,5S,6R)-2-[(2R,3S,4S,5R)-2-(chloromethyl)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CCl)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 FESWLBKGLROKRB-UGDNZRGBSA-N 0.000 claims 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 abstract description 25
229930006000 Sucrose Natural products 0.000 abstract description 25
150000003445 sucroses Chemical class 0.000 abstract description 8
239000000606 toothpaste Substances 0.000 abstract description 5
235000015218 chewing gum Nutrition 0.000 abstract description 4
229940034610 toothpaste Drugs 0.000 abstract description 4
229940112822 chewing gum Drugs 0.000 abstract description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
239000000460 chlorine Substances 0.000 description 24
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
239000000047 product Substances 0.000 description 16
239000000243 solution Substances 0.000 description 12
239000006188 syrup Substances 0.000 description 11
235000020357 syrup Nutrition 0.000 description 11
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 10
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
235000000346 sugar Nutrition 0.000 description 8
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
229940126214 compound 3 Drugs 0.000 description 6
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 6
-1 sucrose ester Chemical class 0.000 description 6
229940125898 compound 5 Drugs 0.000 description 5
238000004949 mass spectrometry Methods 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 5
235000019204 saccharin Nutrition 0.000 description 5
229940081974 saccharin Drugs 0.000 description 5
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 5
UHOVQNZJYSORNB-MZWXYZOWSA-N benzene-d6 Chemical compound [2H]C1=C([2H])C([2H])=C([2H])C([2H])=C1[2H] UHOVQNZJYSORNB-MZWXYZOWSA-N 0.000 description 4
230000003197 catalytic effect Effects 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
239000004615 ingredient Substances 0.000 description 4
229910052500 inorganic mineral Inorganic materials 0.000 description 4
239000011707 mineral Substances 0.000 description 4
235000010755 mineral Nutrition 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
230000002829 reductive effect Effects 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 4
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
235000009508 confectionery Nutrition 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
101150041968 CDC13 gene Proteins 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
206010013911 Dysgeusia Diseases 0.000 description 2
231100000111 LD50 Toxicity 0.000 description 2
229920002774 Maltodextrin Polymers 0.000 description 2
239000007832 Na2SO4 Substances 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
MJOQJPYNENPSSS-XQHKEYJVSA-N [(3r,4s,5r,6s)-4,5,6-triacetyloxyoxan-3-yl] acetate Chemical compound CC(=O)O[C@@H]1CO[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O MJOQJPYNENPSSS-XQHKEYJVSA-N 0.000 description 2
AYJRCSIUFZENHW-UHFFFAOYSA-L barium carbonate Chemical compound [Ba+2].[O-]C([O-])=O AYJRCSIUFZENHW-UHFFFAOYSA-L 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 2
229940109275 cyclamate Drugs 0.000 description 2
HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 2
235000005911 diet Nutrition 0.000 description 2
230000000378 dietary effect Effects 0.000 description 2
229940093499 ethyl acetate Drugs 0.000 description 2
235000019439 ethyl acetate Nutrition 0.000 description 2
239000002198 insoluble material Substances 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
239000011630 iodine Substances 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
239000010410 layer Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
230000037230 mobility Effects 0.000 description 2
239000002324 mouth wash Substances 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
239000000843 powder Substances 0.000 description 2
235000014214 soft drink Nutrition 0.000 description 2
239000008259 solid foam Substances 0.000 description 2
XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 2
239000001117 sulphuric acid Substances 0.000 description 2
235000011149 sulphuric acid Nutrition 0.000 description 2
FVVCFHXLWDDRHG-UPLOTWCNSA-N (2s,3r,4s,5r,6r)-2-[(2r,3s,4r,5r,6r)-6-[(2s,3s,4s,5r)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol Chemical class 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]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O2)O)[C@@H](CO)O1 FVVCFHXLWDDRHG-UPLOTWCNSA-N 0.000 description 1
HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 1
YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 1
244000215068 Acacia senegal Species 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
108010011485 Aspartame Proteins 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
GOJCZVPJCKEBQV-UHFFFAOYSA-N Butyl phthalyl butylglycolate Chemical compound CCCCOC(=O)COC(=O)C1=CC=CC=C1C(=O)OCCCC GOJCZVPJCKEBQV-UHFFFAOYSA-N 0.000 description 1
ISMDILRWKSYCOD-GNKBHMEESA-N C(C1=CC=CC=C1)[C@@H]1NC(OCCCCCCCCCCCNC([C@@H](NC(C[C@@H]1O)=O)C(C)C)=O)=O Chemical compound C(C1=CC=CC=C1)[C@@H]1NC(OCCCCCCCCCCCNC([C@@H](NC(C[C@@H]1O)=O)C(C)C)=O)=O ISMDILRWKSYCOD-GNKBHMEESA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
DQFBYFPFKXHELB-UHFFFAOYSA-N Chalcone Natural products C=1C=CC=CC=1C(=O)C=CC1=CC=CC=C1 DQFBYFPFKXHELB-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
235000005979 Citrus limon Nutrition 0.000 description 1
244000131522 Citrus pyriformis Species 0.000 description 1
229940126639 Compound 33 Drugs 0.000 description 1
108010016626 Dipeptides Proteins 0.000 description 1
239000004150 EU approved colour Substances 0.000 description 1
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 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
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 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
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
239000005913 Maltodextrin Substances 0.000 description 1
244000024873 Mentha crispa Species 0.000 description 1
235000014749 Mentha crispa Nutrition 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
101710084933 Miraculin Proteins 0.000 description 1
108050004114 Monellin Proteins 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
229920002367 Polyisobutene Polymers 0.000 description 1
239000004793 Polystyrene Substances 0.000 description 1
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
239000004141 Sodium laurylsulphate Substances 0.000 description 1
239000004133 Sodium thiosulphate Substances 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
239000002253 acid Substances 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
239000000605 aspartame Substances 0.000 description 1
235000010357 aspartame Nutrition 0.000 description 1
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 1
229960003438 aspartame Drugs 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
MDHYEMXUFSJLGV-UHFFFAOYSA-N beta-phenethyl acetate Natural products CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 1
235000019658 bitter taste Nutrition 0.000 description 1
239000004067 bulking agent Substances 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
FUFJGUQYACFECW-UHFFFAOYSA-L calcium hydrogenphosphate Chemical compound [Ca+2].OP([O-])([O-])=O FUFJGUQYACFECW-UHFFFAOYSA-L 0.000 description 1
150000001720 carbohydrates Chemical class 0.000 description 1
235000014633 carbohydrates Nutrition 0.000 description 1
239000000969 carrier Substances 0.000 description 1
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239000003795 chemical substances by application Substances 0.000 description 1
OAIVIYSBZFEOIU-UHFFFAOYSA-N chloroform;propan-2-one Chemical compound CC(C)=O.ClC(Cl)Cl OAIVIYSBZFEOIU-UHFFFAOYSA-N 0.000 description 1
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229940125782 compound 2 Drugs 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000005695 dehalogenation reaction Methods 0.000 description 1
208000002925 dental caries Diseases 0.000 description 1
235000019700 dicalcium phosphate Nutrition 0.000 description 1
229940095079 dicalcium phosphate anhydrous Drugs 0.000 description 1
FHHZOYXKOICLGH-UHFFFAOYSA-N dichloromethane;ethanol Chemical compound CCO.ClCCl FHHZOYXKOICLGH-UHFFFAOYSA-N 0.000 description 1
WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 1
239000003480 eluent Substances 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000019634 flavors Nutrition 0.000 description 1
239000008103 glucose Substances 0.000 description 1
235000021552 granulated sugar Nutrition 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
230000001939 inductive effect Effects 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000008101 lactose Substances 0.000 description 1
235000015122 lemonade Nutrition 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000006210 lotion Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
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238000004519 manufacturing process Methods 0.000 description 1
239000001683 mentha spicata herb oil Substances 0.000 description 1
NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
239000004200 microcrystalline wax Substances 0.000 description 1
235000019808 microcrystalline wax Nutrition 0.000 description 1
XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 1
229940051866 mouthwash Drugs 0.000 description 1
ARGKVCXINMKCAZ-UZRWAPQLSA-N neohesperidin Chemical compound C1=C(O)C(OC)=CC=C1[C@H]1OC2=CC(O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O[C@H]3[C@@H]([C@H](O)[C@@H](O)[C@H](C)O3)O)=CC(O)=C2C(=O)C1 ARGKVCXINMKCAZ-UZRWAPQLSA-N 0.000 description 1
ARGKVCXINMKCAZ-UHFFFAOYSA-N neohesperidine Natural products C1=C(O)C(OC)=CC=C1C1OC2=CC(OC3C(C(O)C(O)C(CO)O3)OC3C(C(O)C(O)C(C)O3)O)=CC(O)=C2C(=O)C1 ARGKVCXINMKCAZ-UHFFFAOYSA-N 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
229940006093 opthalmologic coloring agent diagnostic Drugs 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
229920002689 polyvinyl acetate Polymers 0.000 description 1
239000011118 polyvinyl acetate Substances 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
238000000746 purification Methods 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
239000002904 solvent Substances 0.000 description 1
235000019721 spearmint oil Nutrition 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
230000009897 systematic effect Effects 0.000 description 1
235000019640 taste Nutrition 0.000 description 1
239000000892 thaumatin Substances 0.000 description 1
235000010436 thaumatin Nutrition 0.000 description 1
DQFBYFPFKXHELB-VAWYXSNFSA-N trans-chalcone Chemical compound C=1C=CC=CC=1C(=O)\C=C\C1=CC=CC=C1 DQFBYFPFKXHELB-VAWYXSNFSA-N 0.000 description 1
239000004034 viscosity adjusting agent Substances 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
- A23G3/00—Sweetmeats; Confectionery; Marzipan; Coated or filled products
- A23G3/34—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof
- A23G3/36—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof characterised by the composition containing organic or inorganic compounds
- A23G3/38—Sucrose-free products
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
- A23G3/00—Sweetmeats; Confectionery; Marzipan; Coated or filled products
- A23G3/34—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof
- A23G3/36—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof characterised by the composition containing organic or inorganic compounds
- A23G3/42—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof characterised by the composition containing organic or inorganic compounds characterised by the carbohydrates used, e.g. polysaccharides
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
- A23G4/00—Chewing gum
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
- A23G4/00—Chewing gum
- A23G4/06—Chewing gum characterised by the composition containing organic or inorganic compounds
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
- A23G4/00—Chewing gum
- A23G4/06—Chewing gum characterised by the composition containing organic or inorganic compounds
- A23G4/064—Chewing gum characterised by the composition containing organic or inorganic compounds containing inorganic compounds
- 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
- A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Preparation or treatment thereof
- A23L2/52—Adding ingredients
- A23L2/60—Sweeteners
- 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
- A23L27/33—Artificial sweetening agents containing sugars or derivatives
- A23L27/37—Halogenated sugars
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/60—Sugars; Derivatives thereof
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H5/00—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium
- C07H5/02—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium to halogen

Landscapes

Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Food Science & Technology (AREA)
Polymers & Plastics (AREA)
General Health & Medical Sciences (AREA)
Inorganic Chemistry (AREA)
Molecular Biology (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Nutrition Science (AREA)
Organic Chemistry (AREA)
Epidemiology (AREA)
Biochemistry (AREA)
Oil, Petroleum & Natural Gas (AREA)
Pharmacology & Pharmacy (AREA)
Medicinal Chemistry (AREA)
General Chemical & Material Sciences (AREA)
Biotechnology (AREA)
Genetics & Genomics (AREA)
Chemical Kinetics & Catalysis (AREA)
Birds (AREA)
Oral & Maxillofacial Surgery (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Saccharide Compounds (AREA)
Seasonings (AREA)
General Preparation And Processing Of Foods (AREA)
Medicines Containing Plant Substances (AREA)
Road Signs Or Road Markings (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA268,863A 1976-01-08 1976-12-29 Sweeteners Expired CA1076110A (en)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA330,179A CA1096233A (en)	1976-01-08	1979-06-20	Sweeteners

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB616/76A GB1543167A (en)	1976-01-08	1976-01-08	Sweeteners

Publications (1)

Publication Number	Publication Date
CA1076110A true CA1076110A (en)	1980-04-22

Family

ID=9707494

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA268,863A Expired CA1076110A (en)	1976-01-08	1976-12-29	Sweeteners

Country Status (28)

Country	Link
JP (1)	JPS5287275A (da)
AT (1)	AT360321B (da)
AU (1)	AU502079B2 (da)
BE (1)	BE850180A (da)
CA (1)	CA1076110A (da)
CH (1)	CH624835A5 (da)
CY (1)	CY1150A (da)
DE (2)	DE2700036C3 (da)
DK (1)	DK147314C (da)
ES (1)	ES454909A1 (da)
FR (1)	FR2337762A1 (da)
GB (1)	GB1543167A (da)
GR (1)	GR62478B (da)
HK (1)	HK79284A (da)
IE (1)	IE44757B1 (da)
IL (1)	IL51227A (da)
IT (1)	IT1082501B (da)
KE (1)	KE3218A (da)
LU (1)	LU76533A1 (da)
MY (1)	MY8300019A (da)
NL (1)	NL177175C (da)
NO (2)	NO142283C (da)
NZ (1)	NZ183033A (da)
PT (1)	PT66040B (da)
SE (1)	SE424039B (da)
TR (1)	TR19279A (da)
YU (1)	YU44002B (da)
ZA (1)	ZA767563B (da)

Families Citing this family (46)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4435440A (en) *	1976-01-08	1984-03-06	Tate & Lyle Limited	Sweeteners
IL58275A0 (en)	1978-09-22	1979-12-30	Tate & Lyle Patent Holdings	Compositions for prevention of tooth decay comprising chlorodeoxysucrose derivative
ATE732T1 (de) *	1978-10-18	1982-03-15	Tate & Lyle Patent Holdings Limited	Verfahren zur herstellung von 2-chlor-2-deoxy-sacchariden und einige 2-chlor-2-deoxy-saccharide.
JPS55118369A (en) *	1979-03-06	1980-09-11	Hayashibara Biochem Lab Inc	Method of making beverage and food
US4335100A (en)	1979-04-23	1982-06-15	Iowa State University Research Foundation, Inc.	Method of inhibiting dextransucrase and oral compositions for use therein
DE3065399D1 (en) *	1979-12-18	1983-11-24	Tate & Lyle Plc	Crystalline 4,1',6'-trichloro-4,1',6'-trideoxy-galactosucrose
LV5131A3 (lv) *	1979-12-20	1993-06-10	Tate & Lyle Plc	4,1',6'-trihlor-4,1',6'-tridezoksigalaktosaharozes iegusanas panemiens
LV5134A3 (lv) *	1980-07-08	1993-06-10	Tate & Lyle Plc	4,1',6'-trihlor-4,1',6'-tridezoksigalaktosaharozes iegusanas panemiens
DE3165986D1 (en) *	1980-07-08	1984-10-18	Tate & Lyle Plc	Process for the preparation of 4, 1',6'-trichloro-4,1',6'-trideoxygalactosucrose (tgs)
CA1183133A (en) *	1980-10-28	1985-02-26	Tate & Lyle Public Limited Company	Sweet chlorine-substituted disaccharides
EP0064361B1 (en) *	1981-04-29	1986-07-02	TATE & LYLE PUBLIC LIMITED COMPANY	Sweetening agents
DE3262120D1 (en) *	1981-05-22	1985-03-14	Tate & Lyle Plc	Brominated sucrose derivatives
US4612373A (en) *	1982-09-13	1986-09-16	Tate & Lyle Public Limited Co.	Trichloro, 6-substituted sucrose compounds, compositions and uses therefor
GB8403611D0 (en) *	1984-02-10	1984-03-14	Tate & Lyle Plc	Sweetener
GB8622345D0 (en) *	1986-09-17	1986-10-22	Tate & Lyle Plc	Sucrose derivatives
GB8627139D0 (en) *	1986-11-13	1986-12-10	Tate & Lyle Plc	Sweetening composition
AU608329B2 (en) *	1987-05-15	1991-03-28	Wm. Wrigley Jr. Company	Chewing gum having a controlled sweetness
GB8723423D0 (en) *	1987-10-06	1987-11-11	Tate & Lyle Plc	Sucralose compositions
PH26074A (en) *	1988-08-09	1992-02-06	Warner Lambert Co	Synergistic sweetening composition containing chloro - compositions containing same and a process for the preparation thereof
US5013716A (en) *	1988-10-28	1991-05-07	Warner-Lambert Company	Unpleasant taste masking compositions and methods for preparing same
US4971797A (en) *	1988-12-22	1990-11-20	Warner-Lambert Company	Stabilized sucralose complex
US5080910A (en) *	1990-05-15	1992-01-14	Werner-Lambert Company	Stabilized chlorodeoxysugar sweetening agents in powder form and methods for preparing same
GB9110821D0 (en)	1991-05-21	1991-07-10	Tate & Lyle Plc	Continuous process for the preparation of sucrose 6-esters
JP3439559B2 (ja) *	1995-02-01	2003-08-25	三栄源エフ・エフ・アイ株式会社	食品の風味向上法
GB9517281D0 (en) *	1995-08-23	1995-10-25	Tate & Lyle Plc	Solid sucralose
US6075139A (en) *	1996-07-24	2000-06-13	Iowa State University Research Foundation, Inc.	Linear and cyclic sucrose reaction products, their preparation and their use
US5900478A (en) *	1997-06-20	1999-05-04	Iowa State University Research Foundation, Inc.	Activated mono-, di-, and polysaccharides reaction products thereof, their preparation and uses
EP1076661A1 (en) *	1998-05-15	2001-02-21	Rostislav G. Zhbankov	Method of preparation of 4,1',6'-trichloro-4,1',6'-trideoxygalactosucrose
EP1210880B8 (en)	1998-10-28	2009-06-03	San-Ei Gen F.F.I., Inc.	Compositions containing sucralose and application thereof
JP4614541B2 (ja)	1999-04-16	2011-01-19	三栄源エフ・エフ・アイ株式会社	スクラロース含有組成物及び該組成物を含む可食性製品
US20030070584A1 (en)	2001-05-15	2003-04-17	Cynthia Gulian	Dip coating compositions containing cellulose ethers
US8309118B2 (en)	2001-09-28	2012-11-13	Mcneil-Ppc, Inc.	Film forming compositions containing sucralose
US7429619B2 (en)	2002-08-02	2008-09-30	Mcneil Consumer Healthcare	Polyacrylic film forming compositions
US6984732B2 (en) *	2003-03-31	2006-01-10	Mcneil-Ppc, Inc.	High-intensity sweetener composition and delivery of same
EP1817964A1 (en) *	2006-02-13	2007-08-15	Sweetwell NV	Functional sugar replacement
US7955630B2 (en)	2004-09-30	2011-06-07	Kraft Foods Global Brands Llc	Thermally stable, high tensile strength encapsulated actives
US20060062811A1 (en)	2004-09-21	2006-03-23	Szymczak Christopher E	Medicinal cooling emulsions
US8148112B2 (en) *	2005-02-16	2012-04-03	National University Corporation Hokkaido University	Sugar chain containing 4-position halogenated galactose and application thereof
DE102005025895A1 (de)	2005-05-27	2006-11-30	Südzucker AG Mannheim/Ochsenfurt	Isomaltulose als geschmacksverkürzendes Agens
US20090220663A1 (en) *	2005-06-22	2009-09-03	Alembic Limited	Process and composition of preparing granular sucralose for emulating table sugar
CN100418976C (zh)	2006-04-03	2008-09-17	广州科宏食品添加物有限公司	一种三氯蔗糖的制备方法
AR070082A1 (es) *	2008-01-04	2010-03-10	Tate & Lyle Technology Ltd	Metodo para la produccion de sucralosa
TR200904862A1 (tr)	2009-05-29	2010-12-21	Sanovel İlaç San. Ve Ti̇c. A.Ş.	Sukraloz formülasyonu ve üretim prosesi
MX365710B (es)	2011-04-29	2019-06-11	Intercontinental Great Brands Llc	Acido encapsulado, metodo para la preparacion del mismo y goma de mascar que comprende el mismo.
US20140082768A1 (en)	2012-09-17	2014-03-20	Mcneil Nutritionals, Llc.	Enhanced natural sweetener
CA2939784C (en)	2014-02-18	2023-01-24	Mcneil Nutritionals, Llc	Process for separation, isolation and characterization of steviol glycosides

1976
- 1976-01-08 GB GB616/76A patent/GB1543167A/en not_active Expired
- 1976-12-15 CY CY1150A patent/CY1150A/xx unknown
- 1976-12-21 ZA ZA767563A patent/ZA767563B/xx unknown
- 1976-12-29 CA CA268,863A patent/CA1076110A/en not_active Expired
1977
- 1977-01-03 DE DE2700036A patent/DE2700036C3/de not_active Expired
- 1977-01-03 DE DE2759739A patent/DE2759739C2/de not_active Expired
- 1977-01-03 GR GR52509A patent/GR62478B/el unknown
- 1977-01-04 FR FR7700041A patent/FR2337762A1/fr active Granted
- 1977-01-04 SE SE7700057A patent/SE424039B/xx not_active IP Right Cessation
- 1977-01-05 IT IT67023/77A patent/IT1082501B/it active
- 1977-01-06 AU AU21118/77A patent/AU502079B2/en not_active Expired
- 1977-01-06 LU LU76533A patent/LU76533A1/xx unknown
- 1977-01-07 IL IL51227A patent/IL51227A/xx unknown
- 1977-01-07 YU YU39/77A patent/YU44002B/xx unknown
- 1977-01-07 AT AT4877A patent/AT360321B/de not_active IP Right Cessation
- 1977-01-07 BE BE173909A patent/BE850180A/xx not_active IP Right Cessation
- 1977-01-07 DK DK7077A patent/DK147314C/da not_active IP Right Cessation
- 1977-01-07 JP JP71377A patent/JPS5287275A/ja active Granted
- 1977-01-07 PT PT66040A patent/PT66040B/pt unknown
- 1977-01-07 NZ NZ183033A patent/NZ183033A/xx unknown
- 1977-01-07 CH CH20977A patent/CH624835A5/de not_active IP Right Cessation
- 1977-01-07 IE IE34/77A patent/IE44757B1/en not_active IP Right Cessation
- 1977-01-07 TR TR19279A patent/TR19279A/xx unknown
- 1977-01-08 ES ES454909A patent/ES454909A1/es not_active Expired
- 1977-01-10 NO NO770068A patent/NO142283C/no unknown
- 1977-01-10 NL NLAANVRAGE7700192,A patent/NL177175C/xx not_active IP Right Cessation
1980
- 1980-03-19 NO NO800785A patent/NO149235C/no unknown
1982
- 1982-05-31 KE KE3218A patent/KE3218A/xx unknown
1983
- 1983-12-30 MY MY19/83A patent/MY8300019A/xx unknown
1984
- 1984-10-18 HK HK792/84A patent/HK79284A/xx unknown

Also Published As

Publication number	Publication date
NO142283B (no)	1980-04-21
DE2700036A1 (de)	1977-07-21
PT66040A (en)	1977-02-01
AT360321B (de)	1980-01-12
DE2700036C3 (de)	1981-10-01
SE424039B (sv)	1982-06-28
FR2337762A1 (fr)	1977-08-05
JPS5287275A (en)	1977-07-20
AU2111877A (en)	1978-07-13
YU3977A (en)	1983-10-31
NO149235C (no)	1984-03-14
CH624835A5 (en)	1981-08-31
PT66040B (en)	1978-06-20
IE44757L (en)	1977-07-08
LU76533A1 (da)	1977-06-17
DE2700036B2 (de)	1981-02-12
BE850180A (fr)	1977-05-02
SE7700057L (sv)	1977-07-09
GB1543167A (en)	1979-03-28
NZ183033A (en)	1978-03-06
NL177175C (nl)	1985-08-16
NO149235B (no)	1983-12-05
ZA767563B (en)	1977-11-30
ATA4877A (de)	1980-05-15
TR19279A (tr)	1978-10-27
YU44002B (en)	1990-02-28
FR2337762B1 (da)	1982-10-15
DE2759739C2 (de)	1984-05-24
NO142283C (no)	1980-07-30
NO800785L (no)	1977-07-11
HK79284A (en)	1984-10-26
NO770068L (no)	1977-07-11
IL51227A0 (en)	1977-03-31
DK147314C (da)	1985-01-21
CY1150A (en)	1982-09-10
DK147314B (da)	1984-06-18
KE3218A (en)	1982-07-09
AU502079B2 (en)	1979-07-12
IE44757B1 (en)	1982-03-24
DK7077A (da)	1977-07-09
IL51227A (en)	1979-12-30
ES454909A1 (es)	1978-04-01
MY8300019A (en)	1983-12-31
GR62478B (en)	1979-04-13
NL177175B (nl)	1985-03-18
NL7700192A (nl)	1977-07-12
IT1082501B (it)	1985-05-21
JPS5540019B2 (da)	1980-10-15

Legal Events

Date	Code	Title	Description
1997-04-22	MKEX	Expiry

Publication	Publication Date	Title
US4549013A (en)	1985-10-22	Chloro-substituted sucrose compounds
IE44757B1 (en)	1982-03-24	Sweeteners
US4405654A (en)	1983-09-20	4'-Halo-substituted sucrose derivatives
EP0103479B1 (en)	1986-02-05	Sucrose derivatives
US5585480A (en)	1996-12-17	Hydrogenated fructooligosaccharides
FI71159C (fi)	1986-11-24	4'-halogensubstituerade sackarosderivat
US4473546A (en)	1984-09-25	Brominated sucrose derivatives, compositions and methods of use
CA1096233A (en)	1981-02-24	Sweeteners
JPH074167B2 (ja)	1995-01-25	低カロリー・低う蝕性アイスクリーム
US4808409A (en)	1989-02-28	Low cariogenic sweetening agents
GB2088855A (en)	1982-06-16	Tetrachlorodisaccharides and their use as sweeteners
JPS6254796B2 (da)	1987-11-17
JPS63258556A (ja)	1988-10-26	飲食物の製造方法