CA1095075A - Flavanone sulfalkylee comme edulcorant - Google Patents

Flavanone sulfalkylee comme edulcorant

Info

Publication number: CA1095075A
Authority: CA; Canada
Prior art keywords: compound; flavanone; formula; dihydrochalcone; solution
Prior art date: 1975-03-24
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

CA350,649A

Other languages

English (en)

Inventor

Guy A. Crosby

Ned M. Weinshenker

Grant E. Dubois

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.)

Dynapol Corp

Original Assignee

Dynapol Corp

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.)

1975-03-24

Filing date

1980-04-25

Publication date

1981-02-03

1975-03-24 Priority claimed from US05/561,522 external-priority patent/US3974299A/en

1976-02-13 Priority claimed from US05/657,905 external-priority patent/US4025535A/en

1980-04-25 Application filed by Dynapol Corp filed Critical Dynapol Corp

1980-04-25 Priority to CA350,649A priority Critical patent/CA1095075A/fr

1981-02-03 Application granted granted Critical

1981-02-03 Publication of CA1095075A publication Critical patent/CA1095075A/fr

Status Expired legal-status Critical Current

Links

235000003599 food sweetener Nutrition 0.000 title claims abstract description 19
239000003765 sweetening agent Substances 0.000 title claims abstract description 19
229930003949 flavanone Natural products 0.000 title claims description 35
235000011981 flavanones Nutrition 0.000 title claims description 35
ZONYXWQDUYMKFB-UHFFFAOYSA-N SJ000286395 Natural products O1C2=CC=CC=C2C(=O)CC1C1=CC=CC=C1 ZONYXWQDUYMKFB-UHFFFAOYSA-N 0.000 title claims description 25
150000002207 flavanone derivatives Chemical class 0.000 title claims 3
239000000463 material Substances 0.000 claims abstract description 39
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 16
239000001257 hydrogen Substances 0.000 claims abstract description 15
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 14
150000001768 cations Chemical class 0.000 claims abstract description 13
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 6
125000000217 alkyl group Chemical group 0.000 claims abstract 4
QGGZBXOADPVUPN-UHFFFAOYSA-N dihydrochalcone Chemical class C=1C=CC=CC=1C(=O)CCC1=CC=CC=C1 QGGZBXOADPVUPN-UHFFFAOYSA-N 0.000 claims abstract 2
PXLWOFBAEVGBOA-UHFFFAOYSA-N dihydrochalcone Natural products OC1C(O)C(O)C(CO)OC1C1=C(O)C=CC(C(=O)CC(O)C=2C=CC(O)=CC=2)=C1O PXLWOFBAEVGBOA-UHFFFAOYSA-N 0.000 claims description 21
-1 dihydrochalcone compound Chemical class 0.000 claims description 21
150000001875 compounds Chemical class 0.000 claims description 15
238000000034 method Methods 0.000 claims description 11
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
229910052751 metal Inorganic materials 0.000 claims description 9
239000002184 metal Substances 0.000 claims description 9
230000008569 process Effects 0.000 claims description 8
239000011575 calcium Substances 0.000 claims description 7
DQFBYFPFKXHELB-UHFFFAOYSA-N Chalcone Natural products C=1C=CC=CC=1C(=O)C=CC1=CC=CC=C1 DQFBYFPFKXHELB-UHFFFAOYSA-N 0.000 claims description 6
235000005513 chalcones Nutrition 0.000 claims description 6
229910052791 calcium Inorganic materials 0.000 claims description 5
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical group [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 4
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
DQFBYFPFKXHELB-VAWYXSNFSA-N trans-chalcone Chemical compound C=1C=CC=CC=1C(=O)\C=C\C1=CC=CC=C1 DQFBYFPFKXHELB-VAWYXSNFSA-N 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 3
230000002152 alkylating effect Effects 0.000 claims description 2
NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical group [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 claims 3
125000005227 alkyl sulfonate group Chemical group 0.000 claims 1
150000002387 hesperetin Chemical class 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
GINSRDSEEGBTJO-UHFFFAOYSA-N thietane 1-oxide Chemical compound O=S1CCC1 GINSRDSEEGBTJO-UHFFFAOYSA-N 0.000 claims 1
235000005911 diet Nutrition 0.000 abstract 1
230000000378 dietary effect Effects 0.000 abstract 1
239000000047 product Substances 0.000 description 36
239000000243 solution Substances 0.000 description 32
150000002208 flavanones Chemical class 0.000 description 28
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 23
238000002360 preparation method Methods 0.000 description 22
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 21
239000000203 mixture Substances 0.000 description 20
JCPGMXJLFWGRMZ-UHFFFAOYSA-N 1-(2-hydroxyphenyl)-3-phenylpropan-1-one Chemical compound OC1=CC=CC=C1C(=O)CCC1=CC=CC=C1 JCPGMXJLFWGRMZ-UHFFFAOYSA-N 0.000 description 18
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 18
238000006243 chemical reaction Methods 0.000 description 17
239000001100 (2S)-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one Substances 0.000 description 14
AIONOLUJZLIMTK-AWEZNQCLSA-N hesperetin Chemical compound C1=C(O)C(OC)=CC=C1[C@H]1OC2=CC(O)=CC(O)=C2C(=O)C1 AIONOLUJZLIMTK-AWEZNQCLSA-N 0.000 description 14
AIONOLUJZLIMTK-UHFFFAOYSA-N hesperetin Natural products C1=C(O)C(OC)=CC=C1C1OC2=CC(O)=CC(O)=C2C(=O)C1 AIONOLUJZLIMTK-UHFFFAOYSA-N 0.000 description 14
235000010209 hesperetin Nutrition 0.000 description 14
229960001587 hesperetin Drugs 0.000 description 14
FTODBIPDTXRIGS-UHFFFAOYSA-N homoeriodictyol Natural products C1=C(O)C(OC)=CC(C2OC3=CC(O)=CC(O)=C3C(=O)C2)=C1 FTODBIPDTXRIGS-UHFFFAOYSA-N 0.000 description 14
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
229930006000 Sucrose Natural products 0.000 description 12
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 12
239000005720 sucrose Substances 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
239000011541 reaction mixture Substances 0.000 description 11
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
239000002585 base Substances 0.000 description 10
235000009508 confectionery Nutrition 0.000 description 10
235000019439 ethyl acetate Nutrition 0.000 description 10
229910052786 argon Inorganic materials 0.000 description 9
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 9
238000001953 recrystallisation Methods 0.000 description 9
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
229910000027 potassium carbonate Inorganic materials 0.000 description 8
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 8
239000007787 solid Substances 0.000 description 8
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
229940093499 ethyl acetate Drugs 0.000 description 7
235000013305 food Nutrition 0.000 description 7
150000003839 salts Chemical class 0.000 description 7
235000019640 taste Nutrition 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
230000029936 alkylation Effects 0.000 description 6
238000005804 alkylation reaction Methods 0.000 description 6
230000009467 reduction Effects 0.000 description 6
238000006722 reduction reaction Methods 0.000 description 6
239000000741 silica gel Substances 0.000 description 6
229910002027 silica gel Inorganic materials 0.000 description 6
239000011780 sodium chloride Substances 0.000 description 6
239000007858 starting material Substances 0.000 description 6
206010013911 Dysgeusia Diseases 0.000 description 5
239000002253 acid Substances 0.000 description 5
150000001299 aldehydes Chemical class 0.000 description 5
238000004458 analytical method Methods 0.000 description 5
239000000284 extract Substances 0.000 description 5
229910052943 magnesium sulfate Inorganic materials 0.000 description 5
239000000126 substance Substances 0.000 description 5
XLEYFDVVXLMULC-UHFFFAOYSA-N 2',4',6'-trihydroxyacetophenone Chemical compound CC(=O)C1=C(O)C=C(O)C=C1O XLEYFDVVXLMULC-UHFFFAOYSA-N 0.000 description 4
IBGBGRVKPALMCQ-UHFFFAOYSA-N 3,4-dihydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1O IBGBGRVKPALMCQ-UHFFFAOYSA-N 0.000 description 4
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 4
238000007792 addition Methods 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
SWYHWRRXAKMZLK-UHFFFAOYSA-N chloromethyl thiohypochlorite Chemical compound ClCSCl SWYHWRRXAKMZLK-UHFFFAOYSA-N 0.000 description 4
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 4
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
239000003921 oil Substances 0.000 description 4
235000019198 oils Nutrition 0.000 description 4
229940093956 potassium carbonate Drugs 0.000 description 4
235000011181 potassium carbonates Nutrition 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
239000006188 syrup Substances 0.000 description 4
235000020357 syrup Nutrition 0.000 description 4
FSSPGSAQUIYDCN-UHFFFAOYSA-N 1,3-Propane sultone Chemical compound O=S1(=O)CCCO1 FSSPGSAQUIYDCN-UHFFFAOYSA-N 0.000 description 3
ICDGTQZUZLBPQV-UHFFFAOYSA-N 3-(2-ethoxyphenyl)-1-phenylprop-2-en-1-one Chemical compound CCOC1=CC=CC=C1C=CC(=O)C1=CC=CC=C1 ICDGTQZUZLBPQV-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
230000002378 acidificating effect Effects 0.000 description 3
125000003545 alkoxy group Chemical group 0.000 description 3
235000013361 beverage Nutrition 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
239000000969 carrier Substances 0.000 description 3
239000003054 catalyst 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
230000000875 corresponding effect Effects 0.000 description 3
239000012043 crude product Substances 0.000 description 3
239000013078 crystal Substances 0.000 description 3
235000013399 edible fruits Nutrition 0.000 description 3
239000003480 eluent Substances 0.000 description 3
239000012259 ether extract Substances 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
229960000443 hydrochloric acid Drugs 0.000 description 3
235000011167 hydrochloric acid Nutrition 0.000 description 3
238000005984 hydrogenation reaction Methods 0.000 description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
231100000252 nontoxic Toxicity 0.000 description 3
230000003000 nontoxic effect Effects 0.000 description 3
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 3
235000015320 potassium carbonate Nutrition 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
239000011734 sodium Substances 0.000 description 3
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
BVOMRRWJQOJMPA-UHFFFAOYSA-N 1,2,3-trithiane Chemical compound C1CSSSC1 BVOMRRWJQOJMPA-UHFFFAOYSA-N 0.000 description 2
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
PCYGLFXKCBFGPC-UHFFFAOYSA-N 3,4-Dihydroxy hydroxymethyl benzene Natural products OCC1=CC=C(O)C(O)=C1 PCYGLFXKCBFGPC-UHFFFAOYSA-N 0.000 description 2
MSLQVALOZKAVQA-UHFFFAOYSA-N 3-[4-(2-bromoethoxy)-2,6-dihydroxycyclohexa-2,4-dien-1-yl]-1-(3-hydroxy-4-methoxyphenyl)prop-2-en-1-one Chemical compound C1=C(O)C(OC)=CC=C1C(=O)C=CC1C(O)=CC(OCCBr)=CC1O MSLQVALOZKAVQA-UHFFFAOYSA-N 0.000 description 2
BCLVKHGKEGFPJV-UHFFFAOYSA-N 4-ethoxy-3-hydroxybenzaldehyde Chemical compound CCOC1=CC=C(C=O)C=C1O BCLVKHGKEGFPJV-UHFFFAOYSA-N 0.000 description 2
RCAIUHIZBAOWJF-UHFFFAOYSA-N 4-ethoxy-3-phenylmethoxybenzaldehyde Chemical compound CCOC1=CC=C(C=O)C=C1OCC1=CC=CC=C1 RCAIUHIZBAOWJF-UHFFFAOYSA-N 0.000 description 2
MHXLNUAELNBFSS-UHFFFAOYSA-N 7-(2-bromoethoxy)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydrochromen-4-one Chemical compound C1=C(O)C(OC)=CC=C1C1OC2=CC(OCCBr)=CC(O)=C2C(=O)C1 MHXLNUAELNBFSS-UHFFFAOYSA-N 0.000 description 2
239000001606 7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)chroman-4-one Substances 0.000 description 2
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
239000001183 FEMA 4495 Substances 0.000 description 2
CWBZAESOUBENAP-QVNVHUMTSA-N Naringin dihydrochalcone Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@H]1[C@H](OC=2C=C(O)C(C(=O)CCC=3C=CC(O)=CC=3)=C(O)C=2)O[C@H](CO)[C@@H](O)[C@@H]1O CWBZAESOUBENAP-QVNVHUMTSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
244000269722 Thea sinensis Species 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
150000008044 alkali metal hydroxides Chemical class 0.000 description 2
239000002168 alkylating agent Substances 0.000 description 2
229940100198 alkylating agent Drugs 0.000 description 2
150000003935 benzaldehydes Chemical class 0.000 description 2
229940076134 benzene Drugs 0.000 description 2
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 2
229940073608 benzyl chloride Drugs 0.000 description 2
239000012267 brine Substances 0.000 description 2
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
239000001913 cellulose Substances 0.000 description 2
235000010980 cellulose Nutrition 0.000 description 2
229920002678 cellulose Polymers 0.000 description 2
150000001789 chalcones Chemical class 0.000 description 2
235000008504 concentrate Nutrition 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical class CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 description 2
239000000796 flavoring agent Substances 0.000 description 2
235000019634 flavors Nutrition 0.000 description 2
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
238000001640 fractional crystallisation Methods 0.000 description 2
235000011852 gelatine desserts Nutrition 0.000 description 2
150000002431 hydrogen Chemical group 0.000 description 2
239000012535 impurity Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
150000002739 metals Chemical class 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical group CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 2
DFPMSGMNTNDNHN-ZPHOTFPESA-N naringin Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@H]1[C@H](OC=2C=C3O[C@@H](CC(=O)C3=C(O)C=2)C=2C=CC(O)=CC=2)O[C@H](CO)[C@@H](O)[C@@H]1O DFPMSGMNTNDNHN-ZPHOTFPESA-N 0.000 description 2
229930019673 naringin Natural products 0.000 description 2
229940052490 naringin Drugs 0.000 description 2
229930014626 natural product Natural products 0.000 description 2
231100000956 nontoxicity Toxicity 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000011591 potassium Substances 0.000 description 2
229960003975 potassium Drugs 0.000 description 2
235000007686 potassium Nutrition 0.000 description 2
239000002243 precursor Substances 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
239000011369 resultant mixture Substances 0.000 description 2
238000007363 ring formation reaction Methods 0.000 description 2
238000007142 ring opening reaction Methods 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
COCJIVDXXCJXND-UHFFFAOYSA-M sodium;iodomethanesulfonate Chemical compound [Na+].[O-]S(=O)(=O)CI COCJIVDXXCJXND-UHFFFAOYSA-M 0.000 description 2
239000012265 solid product Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
238000001228 spectrum Methods 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
229940124530 sulfonamide Drugs 0.000 description 2
150000003456 sulfonamides Chemical class 0.000 description 2
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
239000000725 suspension Substances 0.000 description 2
230000009967 tasteless effect Effects 0.000 description 2
238000004809 thin layer chromatography Methods 0.000 description 2
239000000606 toothpaste Substances 0.000 description 2
YKYIFUROKBDHCY-ONEGZZNKSA-N (e)-4-ethoxy-1,1,1-trifluorobut-3-en-2-one Chemical group CCO\C=C\C(=O)C(F)(F)F YKYIFUROKBDHCY-ONEGZZNKSA-N 0.000 description 1
MRSDBRAGNWAUPL-UHFFFAOYSA-N 1-phenyl-2-phenylmethoxyethanone Chemical compound C=1C=CC=CC=1C(=O)COCC1=CC=CC=C1 MRSDBRAGNWAUPL-UHFFFAOYSA-N 0.000 description 1
ZWJIJEOIENYKPK-UHFFFAOYSA-N 1-phenyl-3-(2-propoxyphenyl)prop-2-en-1-one Chemical group CCCOC1=CC=CC=C1C=CC(=O)C1=CC=CC=C1 ZWJIJEOIENYKPK-UHFFFAOYSA-N 0.000 description 1
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235000015497 potassium bicarbonate Nutrition 0.000 description 1
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TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
239000000843 powder Substances 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
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LCDCPQHFCOBUEF-UHFFFAOYSA-N pyrrolidine-1-carboxamide Chemical compound NC(=O)N1CCCC1 LCDCPQHFCOBUEF-UHFFFAOYSA-N 0.000 description 1
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CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
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239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
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231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
238000012800 visualization Methods 0.000 description 1
235000014101 wine Nutrition 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA350,649A 1975-03-24 1980-04-25 Flavanone sulfalkylee comme edulcorant Expired CA1095075A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA350,649A CA1095075A (fr)	1975-03-24	1980-04-25	Flavanone sulfalkylee comme edulcorant

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
US561,522		1975-03-24
US05/561,522 US3974299A (en)	1974-07-08	1975-03-24	Ionic sweetener
US657,905		1976-02-13
US05/657,905 US4025535A (en)	1975-03-24	1976-02-13	Sulfoalkylated flavanone sweeteners
CA248,600A CA1095063A (fr)	1975-03-24	1976-03-23	Flavanone sulfoalkylee utilisee comme edulcorant
CA350,649A CA1095075A (fr)	1975-03-24	1980-04-25	Flavanone sulfalkylee comme edulcorant

Publications (1)

Publication Number	Publication Date
CA1095075A true CA1095075A (fr)	1981-02-03

Family

ID=27425905

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA350,649A Expired CA1095075A (fr)	1975-03-24	1980-04-25	Flavanone sulfalkylee comme edulcorant

Country Status (1)

Country	Link
CA (1)	CA1095075A (fr)

1980
- 1980-04-25 CA CA350,649A patent/CA1095075A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1998-02-03	MKEX	Expiry

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USRE33719E (en)	1991-10-15	Sweetened edible formulations
EP0068551B1 (fr)	1984-11-14	Edulcorants non nutritifs
US3974299A (en)	1976-08-10	Ionic sweetener
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US4013801A (en)	1977-03-22	Edibles sweetened with flavanones
US4025535A (en)	1977-05-24	Sulfoalkylated flavanone sweeteners
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US4602095A (en)	1986-07-22	3-hydroxy-4-alkyloxyphenyl heterocyclic aromatic carboxylates
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US4283434A (en)	1981-08-11	Sulfamo dihydrochalcone sweeteners
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US3853835A (en)	1974-12-10	Alkyl esters of aspartyl aliphatic amino acid dipeptides
US3625700A (en)	1971-12-07	Edible compositions containing 2' 4' 6' 3-tetrahydroxy - 4 -n-propoxydihydro-chalcone 4'-beta-neohesperidoside
US4545999A (en)	1985-10-08	3-Hydroxy-4-methoxyphenyl aryl carbonates
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