NO122021B - - Google Patents
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- Publication number
- NO122021B NO122021B NO1432/68A NO143268A NO122021B NO 122021 B NO122021 B NO 122021B NO 1432/68 A NO1432/68 A NO 1432/68A NO 143268 A NO143268 A NO 143268A NO 122021 B NO122021 B NO 122021B
- Authority
- NO
- Norway
- Prior art keywords
- tetrazole
- hydroxyphenoxy
- salts
- compound
- water
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 16
- -1 Tetrazole compound Chemical class 0.000 claims description 10
- 231100000252 nontoxic Toxicity 0.000 claims description 7
- 230000003000 nontoxic effect Effects 0.000 claims description 7
- 239000004071 soot Substances 0.000 claims description 6
- DZHBTQHPZSGDOR-UHFFFAOYSA-N Melizame Chemical compound OC1=CC=CC(OC2=NNN=N2)=C1 DZHBTQHPZSGDOR-UHFFFAOYSA-N 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 239000000203 mixture Substances 0.000 description 13
- 239000000047 product Substances 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 235000019640 taste Nutrition 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Substances C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000000625 cyclamic acid and its Na and Ca salt Substances 0.000 description 6
- 235000019204 saccharin Nutrition 0.000 description 6
- 229940081974 saccharin Drugs 0.000 description 6
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 6
- UDIPTWFVPPPURJ-UHFFFAOYSA-M Cyclamate Chemical compound [Na+].[O-]S(=O)(=O)NC1CCCCC1 UDIPTWFVPPPURJ-UHFFFAOYSA-M 0.000 description 5
- 206010013911 Dysgeusia Diseases 0.000 description 5
- 125000002252 acyl group Chemical group 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
- 229960001462 sodium cyclamate Drugs 0.000 description 5
- 239000003765 sweetening agent Substances 0.000 description 5
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
- 150000003536 tetrazoles Chemical class 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000003863 ammonium salts Chemical class 0.000 description 3
- 239000012259 ether extract Substances 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 235000021092 sugar substitutes Nutrition 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- XPCTZQVDEJYUGT-UHFFFAOYSA-N 3-hydroxy-2-methyl-4-pyrone Chemical compound CC=1OC=CC(=O)C=1O XPCTZQVDEJYUGT-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 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
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 159000000007 calcium salts Chemical class 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 235000003599 food sweetener Nutrition 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 235000019605 sweet taste sensations Nutrition 0.000 description 2
- ZMSIFJQFUSZVBA-UHFFFAOYSA-N 2-(2h-tetrazol-5-yloxy)phenol Chemical compound OC1=CC=CC=C1OC1=NNN=N1 ZMSIFJQFUSZVBA-UHFFFAOYSA-N 0.000 description 1
- UEHGAHXMHNQDIT-UHFFFAOYSA-N 5-phenoxy-2h-tetrazole Chemical compound C=1C=CC=CC=1OC=1N=NNN=1 UEHGAHXMHNQDIT-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- 244000131522 Citrus pyriformis Species 0.000 description 1
- 240000000560 Citrus x paradisi Species 0.000 description 1
- 240000006240 Linum usitatissimum Species 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- HYMLWHLQFGRFIY-UHFFFAOYSA-N Maltol Natural products CC1OC=CC(=O)C1=O HYMLWHLQFGRFIY-UHFFFAOYSA-N 0.000 description 1
- 208000008589 Obesity Diseases 0.000 description 1
- 244000269722 Thea sinensis Species 0.000 description 1
- XIEOBGMYVCOEEH-UHFFFAOYSA-N [3-(2H-tetrazol-5-yloxy)phenyl] acetate Chemical compound C(C)(=O)OC=1C=C(OC2=NN=NN2)C=CC1 XIEOBGMYVCOEEH-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000015895 biscuits Nutrition 0.000 description 1
- 235000019658 bitter taste Nutrition 0.000 description 1
- 235000021152 breakfast Nutrition 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- BTMVHUNTONAYDX-UHFFFAOYSA-N butyl propionate Chemical compound CCCCOC(=O)CC BTMVHUNTONAYDX-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 229940043202 calcium cyclamate Drugs 0.000 description 1
- ZQNPDAVSHFGLIQ-UHFFFAOYSA-N calcium;hydrate Chemical compound O.[Ca] ZQNPDAVSHFGLIQ-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001767 cationic compounds Chemical class 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 235000019219 chocolate Nutrition 0.000 description 1
- HPNSNYBUADCFDR-UHFFFAOYSA-N chromafenozide Chemical compound CC1=CC(C)=CC(C(=O)N(NC(=O)C=2C(=C3CCCOC3=CC=2)C)C(C)(C)C)=C1 HPNSNYBUADCFDR-UHFFFAOYSA-N 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 150000004683 dihydrates Chemical class 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- LFVPBERIVUNMGV-UHFFFAOYSA-N fasudil hydrochloride Chemical compound Cl.C=1C=CC2=CN=CC=C2C=1S(=O)(=O)N1CCCNCC1 LFVPBERIVUNMGV-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000021564 flavored carbonated beverage Nutrition 0.000 description 1
- 235000004426 flaxseed Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- JMANVNJQNLATNU-UHFFFAOYSA-N glycolonitrile Natural products N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910001411 inorganic cation Inorganic materials 0.000 description 1
- 235000020845 low-calorie diet Nutrition 0.000 description 1
- 229940043353 maltol Drugs 0.000 description 1
- 239000011159 matrix material Substances 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
- 235000020824 obesity Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 230000008288 physiological mechanism Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- ZZPKZRHERLGEKA-UHFFFAOYSA-N resorcinol monoacetate Chemical compound CC(=O)OC1=CC=CC(O)=C1 ZZPKZRHERLGEKA-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- AYGJDUHQRFKLBG-UHFFFAOYSA-M sodium;1,1-dioxo-1,2-benzothiazol-3-olate;dihydrate Chemical compound O.O.[Na+].C1=CC=C2C(=O)[N-]S(=O)(=O)C2=C1 AYGJDUHQRFKLBG-UHFFFAOYSA-M 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S426/00—Food or edible material: processes, compositions, and products
- Y10S426/804—Low calorie, low sodium or hypoallergic
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Confectionery (AREA)
- Tea And Coffee (AREA)
- Seasonings (AREA)
- General Preparation And Processing Of Foods (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US63083267A | 1967-04-14 | 1967-04-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO122021B true NO122021B (ref) | 1971-05-10 |
Family
ID=24528728
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO1432/68A NO122021B (ref) | 1967-04-14 | 1968-04-16 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US3515727A (ref) |
| AT (1) | AT278780B (ref) |
| BE (1) | BE715043A (ref) |
| CY (1) | CY738A (ref) |
| DE (1) | DE1770214C3 (ref) |
| ES (1) | ES352723A1 (ref) |
| FI (1) | FI48092C (ref) |
| GB (1) | GB1221115A (ref) |
| IE (1) | IE32023B1 (ref) |
| IT (1) | IT1035008B (ref) |
| MY (1) | MY7400103A (ref) |
| NL (1) | NL144607B (ref) |
| NO (1) | NO122021B (ref) |
| SE (1) | SE342230B (ref) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4166819A (en) * | 1975-09-24 | 1979-09-04 | Abbott Laboratories | 4-Aroyl substituted phenoxy methylene-5-tetrazoles |
| US4309446A (en) * | 1980-02-22 | 1982-01-05 | Eli Lilly And Company | 5-(Dihydroxyphenoxy)tetrazoles and use as sweeteners for medical compositions |
| KR970002877B1 (ko) * | 1987-07-17 | 1997-03-12 | 더 누트라스웨트 캄파니 | 고성능 감미제 |
| WO1990000552A1 (en) * | 1988-07-12 | 1990-01-25 | The Nutrasweet Company | High potency sweetening agents |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1216880B (de) * | 1964-07-04 | 1966-05-18 | Bayer Ag | Verfahren zur Herstellung von substituierten Tetrazolen |
-
1967
- 1967-04-14 US US630832A patent/US3515727A/en not_active Expired - Lifetime
-
1968
- 1968-04-12 AT AT365568A patent/AT278780B/de active
- 1968-04-13 ES ES352723A patent/ES352723A1/es not_active Expired
- 1968-04-16 GB GB07998/68A patent/GB1221115A/en not_active Expired
- 1968-04-16 DE DE1770214A patent/DE1770214C3/de not_active Expired
- 1968-04-16 FI FI681038A patent/FI48092C/fi active
- 1968-04-16 SE SE5081/68A patent/SE342230B/xx unknown
- 1968-04-16 NO NO1432/68A patent/NO122021B/no unknown
- 1968-04-16 NL NL686805345A patent/NL144607B/xx not_active IP Right Cessation
- 1968-04-16 IT IT36335/68A patent/IT1035008B/it active
- 1968-04-17 IE IE436/68A patent/IE32023B1/xx unknown
- 1968-05-13 BE BE715043D patent/BE715043A/xx unknown
-
1974
- 1974-04-18 CY CY73874A patent/CY738A/xx unknown
- 1974-12-30 MY MY103/74A patent/MY7400103A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE1770214B2 (de) | 1973-10-31 |
| NL6805345A (ref) | 1968-10-15 |
| FI48092C (fi) | 1974-06-10 |
| FI48092B (ref) | 1974-02-28 |
| NL144607B (nl) | 1975-01-15 |
| DE1770214C3 (de) | 1974-06-06 |
| US3515727A (en) | 1970-06-02 |
| CY738A (en) | 1974-04-18 |
| MY7400103A (en) | 1974-12-31 |
| DE1770214A1 (de) | 1972-02-10 |
| GB1221115A (en) | 1971-02-03 |
| IE32023L (en) | 1968-10-14 |
| BE715043A (ref) | 1968-11-13 |
| IT1035008B (it) | 1979-10-20 |
| SE342230B (ref) | 1972-01-31 |
| IE32023B1 (en) | 1973-03-21 |
| AT278780B (de) | 1970-02-10 |
| ES352723A1 (es) | 1970-01-01 |
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