JPS6136838B2

JPS6136838B2 -

Info

Publication number: JPS6136838B2
Authority: JP; Japan
Prior art keywords: mixture; formula; solution; water; add
Prior art date: 1981-08-07
Legal status : Expired

Application number

JP56123936A

Other languages

English (en)

Japanese (ja)

Other versions

JPS5826851A (ja

Inventor

Motsuto Burenan Toomasu

Izeru Hendoritsuku Maikeru

Current Assignee

Pfizer Corp Belgium

Original Assignee

Pfizer Corp Belgium

Priority date

1981-08-07

Filing date

1981-08-07

Publication date

1986-08-20

1981-08-07 Application filed by Pfizer Corp Belgium filed Critical Pfizer Corp Belgium

1981-08-07 Priority to JP56123936A priority Critical patent/JPS5826851A/ja

1983-02-17 Publication of JPS5826851A publication Critical patent/JPS5826851A/ja

1986-08-20 Publication of JPS6136838B2 publication Critical patent/JPS6136838B2/ja

Status Granted legal-status Critical Current

Links

239000000203 mixture Substances 0.000 claims description 198
150000001408 amides Chemical class 0.000 claims description 76
150000001875 compounds Chemical class 0.000 claims description 61
-1 cation salt Chemical class 0.000 claims description 51
108010016626 Dipeptides Proteins 0.000 claims description 32
239000002253 acid Substances 0.000 claims description 25
DWBZEJHQQIURML-IUYQGCFVSA-N (3s)-3-amino-4-[[(1r)-1-carboxy-2-hydroxyethyl]amino]-4-oxobutanoic acid Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](CO)C(O)=O DWBZEJHQQIURML-IUYQGCFVSA-N 0.000 claims description 23
150000003839 salts Chemical class 0.000 claims description 22
229940081974 saccharin Drugs 0.000 claims description 18
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 claims description 18
235000019204 saccharin Nutrition 0.000 claims description 18
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 claims description 18
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
239000001257 hydrogen Substances 0.000 claims description 15
229910052739 hydrogen Inorganic materials 0.000 claims description 15
235000013305 food Nutrition 0.000 claims description 12
SGBKWNVYBHTKLV-UHFFFAOYSA-N 2,2,4,4-tetramethylthietan-3-amine Chemical compound CC1(C)SC(C)(C)C1N SGBKWNVYBHTKLV-UHFFFAOYSA-N 0.000 claims description 7
231100000252 nontoxic Toxicity 0.000 claims description 5
230000003000 nontoxic effect Effects 0.000 claims description 5
WYTCYNLLSHMVOE-JGVFFNPUSA-N (3s)-3-amino-4-[[(2r)-3-hydroxy-1-oxo-1-[(2,2,4,4-tetramethyl-1,1-dioxothietan-3-yl)amino]propan-2-yl]amino]-4-oxobutanoic acid Chemical compound CC1(C)C(NC(=O)[C@@H](CO)NC(=O)[C@@H](N)CC(O)=O)C(C)(C)S1(=O)=O WYTCYNLLSHMVOE-JGVFFNPUSA-N 0.000 claims description 3
WJYDZIWWWBWFNU-JGVFFNPUSA-N (3s)-3-amino-4-[[(2r)-3-hydroxy-1-oxo-1-[(2,2,4,4-tetramethylthietan-3-yl)amino]propan-2-yl]amino]-4-oxobutanoic acid Chemical compound CC1(C)SC(C)(C)C1NC(=O)[C@@H](CO)NC(=O)[C@@H](N)CC(O)=O WJYDZIWWWBWFNU-JGVFFNPUSA-N 0.000 claims description 3
MQZQTOLKQHDTIV-UHFFFAOYSA-N 2,2,4,4-tetramethyl-1,1-dioxothietan-3-amine Chemical compound CC1(C)C(N)C(C)(C)S1(=O)=O MQZQTOLKQHDTIV-UHFFFAOYSA-N 0.000 claims description 3
125000002091 cationic group Chemical group 0.000 claims description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 176
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 157
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 156
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 153
239000000243 solution Substances 0.000 description 149
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 129
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 125
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 113
239000000047 product Substances 0.000 description 82
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 79
239000002904 solvent Substances 0.000 description 67
238000003756 stirring Methods 0.000 description 63
238000000034 method Methods 0.000 description 61
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 60
239000000284 extract Substances 0.000 description 59
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 56
239000011541 reaction mixture Substances 0.000 description 48
235000019441 ethanol Nutrition 0.000 description 42
239000010410 layer Substances 0.000 description 42
239000007788 liquid Substances 0.000 description 42
239000007787 solid Substances 0.000 description 39
238000010992 reflux Methods 0.000 description 37
229930006000 Sucrose Natural products 0.000 description 35
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 35
238000006243 chemical reaction Methods 0.000 description 35
239000005720 sucrose Substances 0.000 description 35
239000011734 sodium Substances 0.000 description 33
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
238000004519 manufacturing process Methods 0.000 description 32
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 30
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
150000001412 amines Chemical class 0.000 description 30
229960001701 chloroform Drugs 0.000 description 30
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 27
229910052708 sodium Inorganic materials 0.000 description 25
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 24
239000003054 catalyst Substances 0.000 description 24
239000012044 organic layer Substances 0.000 description 22
230000002829 reductive effect Effects 0.000 description 21
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 21
239000007864 aqueous solution Substances 0.000 description 20
239000012267 brine Substances 0.000 description 20
150000002576 ketones Chemical class 0.000 description 20
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 19
150000002148 esters Chemical class 0.000 description 19
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 18
238000001816 cooling Methods 0.000 description 18
238000002360 preparation method Methods 0.000 description 18
235000003599 food sweetener Nutrition 0.000 description 17
125000006239 protecting group Chemical group 0.000 description 17
239000003765 sweetening agent Substances 0.000 description 17
229960005261 aspartic acid Drugs 0.000 description 15
238000001035 drying Methods 0.000 description 15
235000017557 sodium bicarbonate Nutrition 0.000 description 15
229910000030 sodium bicarbonate Inorganic materials 0.000 description 15
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
DLRVVLDZNNYCBX-UHFFFAOYSA-N Polydextrose Polymers OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(O)O1 DLRVVLDZNNYCBX-UHFFFAOYSA-N 0.000 description 14
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 14
239000004615 ingredient Substances 0.000 description 14
150000002923 oximes Chemical class 0.000 description 14
MTCFGRXMJLQNBG-UWTATZPHSA-N D-Serine Chemical compound OC[C@@H](N)C(O)=O MTCFGRXMJLQNBG-UWTATZPHSA-N 0.000 description 12
229930195711 D-Serine Natural products 0.000 description 12
CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical class OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 12
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
229940024606 amino acid Drugs 0.000 description 12
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 11
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
238000001914 filtration Methods 0.000 description 11
239000002244 precipitate Substances 0.000 description 11
239000007921 spray Substances 0.000 description 11
238000005406 washing Methods 0.000 description 11
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 10
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 10
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 10
229960000583 acetic acid Drugs 0.000 description 10
150000008065 acid anhydrides Chemical class 0.000 description 10
230000002378 acidificating effect Effects 0.000 description 10
125000000217 alkyl group Chemical group 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
235000001014 amino acid Nutrition 0.000 description 9
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 9
235000015165 citric acid Nutrition 0.000 description 9
238000004821 distillation Methods 0.000 description 9
239000000741 silica gel Substances 0.000 description 9
229910002027 silica gel Inorganic materials 0.000 description 9
239000002002 slurry Substances 0.000 description 9
238000005160 1H NMR spectroscopy Methods 0.000 description 8
HXVNBWAKAOHACI-UHFFFAOYSA-N 2,4-dimethyl-3-pentanone Chemical compound CC(C)C(=O)C(C)C HXVNBWAKAOHACI-UHFFFAOYSA-N 0.000 description 8
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
150000001413 amino acids Chemical class 0.000 description 8
150000008064 anhydrides Chemical class 0.000 description 8
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 8
CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 8
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
238000000746 purification Methods 0.000 description 8
229920006395 saturated elastomer Polymers 0.000 description 8
239000011780 sodium chloride Substances 0.000 description 8
239000000126 substance Substances 0.000 description 8
235000019640 taste Nutrition 0.000 description 8
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
CKLJMWTZIZZHCS-UHFFFAOYSA-N D-OH-Asp Natural products OC(=O)C(N)CC(O)=O CKLJMWTZIZZHCS-UHFFFAOYSA-N 0.000 description 7
150000008574 D-amino acids Chemical class 0.000 description 7
CKLJMWTZIZZHCS-UWTATZPHSA-N L-Aspartic acid Natural products OC(=O)[C@H](N)CC(O)=O CKLJMWTZIZZHCS-UWTATZPHSA-N 0.000 description 7
229920001100 Polydextrose Polymers 0.000 description 7
QDAYJHVWIRGGJM-UHFFFAOYSA-B [Mo+4].[Mo+4].[Mo+4].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O Chemical compound [Mo+4].[Mo+4].[Mo+4].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QDAYJHVWIRGGJM-UHFFFAOYSA-B 0.000 description 7
239000007789 gas Substances 0.000 description 7
239000001259 polydextrose Substances 0.000 description 7
235000013856 polydextrose Nutrition 0.000 description 7
229940035035 polydextrose Drugs 0.000 description 7
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 7
239000012265 solid product Substances 0.000 description 7
238000004809 thin layer chromatography Methods 0.000 description 7
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 6
238000010521 absorption reaction Methods 0.000 description 6
235000019658 bitter taste Nutrition 0.000 description 6
125000004432 carbon atom Chemical group C* 0.000 description 6
238000004440 column chromatography Methods 0.000 description 6
235000009508 confectionery Nutrition 0.000 description 6
238000007796 conventional method Methods 0.000 description 6
238000000354 decomposition reaction Methods 0.000 description 6
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 6
239000001632 sodium acetate Substances 0.000 description 6
235000017281 sodium acetate Nutrition 0.000 description 6
239000007858 starting material Substances 0.000 description 6
150000003462 sulfoxides Chemical group 0.000 description 6
FTLYMKDSHNWQKD-UHFFFAOYSA-N (2,4,5-trichlorophenyl)boronic acid Chemical compound OB(O)C1=CC(Cl)=C(Cl)C=C1Cl FTLYMKDSHNWQKD-UHFFFAOYSA-N 0.000 description 5
150000007513 acids Chemical class 0.000 description 5
230000009286 beneficial effect Effects 0.000 description 5
239000012043 crude product Substances 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
238000005984 hydrogenation reaction Methods 0.000 description 5
239000003921 oil Substances 0.000 description 5
235000019198 oils Nutrition 0.000 description 5
239000000843 powder Substances 0.000 description 5
239000000376 reactant Substances 0.000 description 5
238000006722 reduction reaction Methods 0.000 description 5
229940085605 saccharin sodium Drugs 0.000 description 5
150000003457 sulfones Chemical class 0.000 description 5
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
WGLLSSPDPJPLOR-UHFFFAOYSA-N 2,3-dimethylbut-2-ene Chemical compound CC(C)=C(C)C WGLLSSPDPJPLOR-UHFFFAOYSA-N 0.000 description 4
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 4
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 4
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
UDIPTWFVPPPURJ-UHFFFAOYSA-M Cyclamate Chemical compound [Na+].[O-]S(=O)(=O)NC1CCCCC1 UDIPTWFVPPPURJ-UHFFFAOYSA-M 0.000 description 4
RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 4
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 4
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 4
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
238000005481 NMR spectroscopy Methods 0.000 description 4
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
229910000147 aluminium phosphate Inorganic materials 0.000 description 4
239000000908 ammonium hydroxide Substances 0.000 description 4
235000003704 aspartic acid Nutrition 0.000 description 4
239000002585 base Substances 0.000 description 4
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 4
235000013361 beverage Nutrition 0.000 description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
229910052794 bromium Inorganic materials 0.000 description 4
239000011575 calcium Substances 0.000 description 4
229910052791 calcium Inorganic materials 0.000 description 4
150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
235000008504 concentrate Nutrition 0.000 description 4
229940109275 cyclamate Drugs 0.000 description 4
BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 4
230000000694 effects Effects 0.000 description 4
239000000796 flavoring agent Substances 0.000 description 4
235000019253 formic acid Nutrition 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
229910000037 hydrogen sulfide Inorganic materials 0.000 description 4
238000007327 hydrogenolysis reaction Methods 0.000 description 4
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
239000011777 magnesium Substances 0.000 description 4
238000002156 mixing Methods 0.000 description 4
239000012299 nitrogen atmosphere Substances 0.000 description 4
239000011591 potassium Substances 0.000 description 4
229910052700 potassium Inorganic materials 0.000 description 4
239000001509 sodium citrate Substances 0.000 description 4
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 4
239000000725 suspension Substances 0.000 description 4
239000006188 syrup Substances 0.000 description 4
235000020357 syrup Nutrition 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
239000005051 trimethylchlorosilane Substances 0.000 description 4
DVUFTQLHHHJEMK-DMTCNVIQSA-N (3s)-3-amino-4-[[(1r)-1-carboxyethyl]amino]-4-oxobutanoic acid Chemical compound OC(=O)[C@@H](C)NC(=O)[C@@H](N)CC(O)=O DVUFTQLHHHJEMK-DMTCNVIQSA-N 0.000 description 3
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
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