NZ196037A

NZ196037A - L-aspartyl-d-amino acyl amides,and compositions for sweetening edible materials

L-aspartyl-d-amino acyl amides,and compositions for sweetening edible materials

Info

Publication number: NZ196037A
Authority: NZ; New Zealand
Prior art keywords: methyl; amide; mixture; ethyl; aspartyl
Prior art date: 1980-01-21

Application number

NZ196037A

Other languages

English (en)

Inventor

T M Brennan

M E Hendrick

Original Assignee

Pfizer

Priority date

1980-01-21

Filing date

1981-01-16

Publication date

1984-07-06

1980-11-05 Priority claimed from US06/201,745 external-priority patent/US4411925A/en

1981-01-16 Application filed by Pfizer filed Critical Pfizer

1981-01-16 Priority to NZ20317781A priority Critical patent/NZ203177A/en

1981-01-16 Priority to NZ20317681A priority patent/NZ203176A/en

1984-07-06 Publication of NZ196037A publication Critical patent/NZ196037A/en

Links

239000000203 mixture Substances 0.000 title claims description 266
150000001408 amides Chemical class 0.000 title claims description 121
-1 L-aspartyl-d-amino Chemical group 0.000 title claims description 89
239000000463 material Substances 0.000 title claims description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 158
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 136
238000000034 method Methods 0.000 claims description 126
150000001875 compounds Chemical class 0.000 claims description 108
239000002904 solvent Substances 0.000 claims description 63
108010016626 Dipeptides Proteins 0.000 claims description 56
239000000284 extract Substances 0.000 claims description 51
229910052739 hydrogen Inorganic materials 0.000 claims description 42
239000011541 reaction mixture Substances 0.000 claims description 42
239000001257 hydrogen Substances 0.000 claims description 41
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 38
125000000217 alkyl group Chemical group 0.000 claims description 37
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 37
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 37
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 claims description 36
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 claims description 29
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 27
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 25
239000002253 acid Substances 0.000 claims description 24
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 21
229940081974 saccharin Drugs 0.000 claims description 21
235000019204 saccharin Nutrition 0.000 claims description 21
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 claims description 21
229910052799 carbon Inorganic materials 0.000 claims description 20
239000000741 silica gel Substances 0.000 claims description 20
229910002027 silica gel Inorganic materials 0.000 claims description 20
125000004432 carbon atom Chemical group C* 0.000 claims description 19
238000002360 preparation method Methods 0.000 claims description 19
150000003839 salts Chemical class 0.000 claims description 19
235000017557 sodium bicarbonate Nutrition 0.000 claims description 19
229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 19
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 16
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 12
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 9
238000004440 column chromatography Methods 0.000 claims description 9
231100000252 nontoxic Toxicity 0.000 claims description 6
230000003000 nontoxic effect Effects 0.000 claims description 6
125000000896 monocarboxylic acid group Chemical group 0.000 claims description 5
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
229910052717 sulfur Inorganic materials 0.000 claims description 4
150000001721 carbon Chemical group 0.000 claims description 3
235000014171 carbonated beverage Nutrition 0.000 claims description 3
125000002091 cationic group Chemical group 0.000 claims description 3
239000003795 chemical substances by application Substances 0.000 claims description 3
125000000570 L-alpha-aspartyl group Chemical group [H]OC(=O)C([H])([H])[C@]([H])(N([H])[H])C(*)=O 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 223
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 180
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 168
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 162
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 149
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 115
239000000243 solution Substances 0.000 description 113
239000000047 product Substances 0.000 description 92
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 91
150000002576 ketones Chemical class 0.000 description 72
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 66
150000001412 amines Chemical class 0.000 description 58
229930006000 Sucrose Natural products 0.000 description 51
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 51
239000005720 sucrose Substances 0.000 description 51
238000006243 chemical reaction Methods 0.000 description 47
238000010992 reflux Methods 0.000 description 46
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 44
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 42
239000007787 solid Substances 0.000 description 42
239000000543 intermediate Substances 0.000 description 40
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 36
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 33
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 32
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 31
238000001914 filtration Methods 0.000 description 31
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 30
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 30
230000002829 reductive effect Effects 0.000 description 28
235000003599 food sweetener Nutrition 0.000 description 27
239000011734 sodium Substances 0.000 description 27
238000003756 stirring Methods 0.000 description 27
239000003765 sweetening agent Substances 0.000 description 27
239000012267 brine Substances 0.000 description 26
239000003054 catalyst Substances 0.000 description 26
229910052708 sodium Inorganic materials 0.000 description 26
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 25
238000004809 thin layer chromatography Methods 0.000 description 25
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 22
150000002923 oximes Chemical class 0.000 description 22
238000001704 evaporation Methods 0.000 description 21
230000008020 evaporation Effects 0.000 description 21
239000012044 organic layer Substances 0.000 description 21
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 20
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 20
239000003921 oil Substances 0.000 description 19
235000019198 oils Nutrition 0.000 description 19
239000000706 filtrate Substances 0.000 description 18
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 18
239000008346 aqueous phase Substances 0.000 description 16
239000007788 liquid Substances 0.000 description 16
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 16
CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 15
229940024606 amino acid Drugs 0.000 description 15
230000036515 potency Effects 0.000 description 15
HXVNBWAKAOHACI-UHFFFAOYSA-N 2,4-dimethyl-3-pentanone Chemical compound CC(C)C(=O)C(C)C HXVNBWAKAOHACI-UHFFFAOYSA-N 0.000 description 14
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 14
229960005261 aspartic acid Drugs 0.000 description 14
238000007327 hydrogenolysis reaction Methods 0.000 description 14
239000004615 ingredient Substances 0.000 description 14
229940086542 triethylamine Drugs 0.000 description 14
238000005160 1H NMR spectroscopy Methods 0.000 description 13
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 13
235000009508 confectionery Nutrition 0.000 description 13
125000006239 protecting group Chemical group 0.000 description 13
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 12
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 12
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 12
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 12
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
150000008064 anhydrides Chemical class 0.000 description 12
230000007062 hydrolysis Effects 0.000 description 12
238000006460 hydrolysis reaction Methods 0.000 description 12
229910052740 iodine Inorganic materials 0.000 description 12
239000010410 layer Substances 0.000 description 12
QNAYBMKLOCPYGJ-UWTATZPHSA-N D-alanine Chemical compound C[C@@H](N)C(O)=O QNAYBMKLOCPYGJ-UWTATZPHSA-N 0.000 description 11
QNAYBMKLOCPYGJ-UHFFFAOYSA-N D-alpha-Ala Natural products CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 description 11
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 11
239000003153 chemical reaction reagent Substances 0.000 description 11
239000000843 powder Substances 0.000 description 11
239000007921 spray Substances 0.000 description 11
150000003462 sulfoxides Chemical class 0.000 description 11
CKLJMWTZIZZHCS-UHFFFAOYSA-N D-OH-Asp Natural products OC(=O)C(N)CC(O)=O CKLJMWTZIZZHCS-UHFFFAOYSA-N 0.000 description 10
QWCKQJZIFLGMSD-GSVOUGTGSA-N D-alpha-aminobutyric acid Chemical compound CC[C@@H](N)C(O)=O QWCKQJZIFLGMSD-GSVOUGTGSA-N 0.000 description 10
150000008574 D-amino acids Chemical class 0.000 description 10
235000013361 beverage Nutrition 0.000 description 10
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 10
235000015165 citric acid Nutrition 0.000 description 10
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 9
CKLJMWTZIZZHCS-UWTATZPHSA-N L-Aspartic acid Natural products OC(=O)[C@H](N)CC(O)=O CKLJMWTZIZZHCS-UWTATZPHSA-N 0.000 description 9
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 9
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 9
150000002148 esters Chemical class 0.000 description 9
235000019253 formic acid Nutrition 0.000 description 9
238000010438 heat treatment Methods 0.000 description 9
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
238000006722 reduction reaction Methods 0.000 description 9
150000003457 sulfones Chemical class 0.000 description 9
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 8
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 8
239000007864 aqueous solution Substances 0.000 description 8
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 8
238000001816 cooling Methods 0.000 description 8
238000001035 drying Methods 0.000 description 8
235000013305 food Nutrition 0.000 description 8
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 8
229920006395 saturated elastomer Polymers 0.000 description 8
239000000725 suspension Substances 0.000 description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 7
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 7
150000001413 amino acids Chemical class 0.000 description 7
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 7
229910052794 bromium Inorganic materials 0.000 description 7
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 7
230000008878 coupling Effects 0.000 description 7
238000010168 coupling process Methods 0.000 description 7
238000005859 coupling reaction Methods 0.000 description 7
239000000796 flavoring agent Substances 0.000 description 7
229910000037 hydrogen sulfide Inorganic materials 0.000 description 7
229910052943 magnesium sulfate Inorganic materials 0.000 description 7
238000000746 purification Methods 0.000 description 7
239000002002 slurry Substances 0.000 description 7
238000001228 spectrum Methods 0.000 description 7
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 6
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
SNDPXSYFESPGGJ-SCSAIBSYSA-N D-2-aminopentanoic acid Chemical compound CCC[C@@H](N)C(O)=O SNDPXSYFESPGGJ-SCSAIBSYSA-N 0.000 description 6
229930182831 D-valine Natural products 0.000 description 6
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 6
229920001100 Polydextrose Polymers 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
235000001014 amino acid Nutrition 0.000 description 6
229910021529 ammonia Inorganic materials 0.000 description 6
239000002585 base Substances 0.000 description 6
235000012970 cakes Nutrition 0.000 description 6
235000008504 concentrate Nutrition 0.000 description 6
239000012043 crude product Substances 0.000 description 6
235000019634 flavors Nutrition 0.000 description 6
239000001259 polydextrose Substances 0.000 description 6
235000013856 polydextrose Nutrition 0.000 description 6
229940035035 polydextrose Drugs 0.000 description 6
239000002243 precursor Substances 0.000 description 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
239000007858 starting material Substances 0.000 description 6
235000019640 taste Nutrition 0.000 description 6
MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 6
FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 6
235000012141 vanillin Nutrition 0.000 description 6
238000005406 washing Methods 0.000 description 6
KNIZBZYMVRWQKN-DMTCNVIQSA-N (3s)-3-amino-4-[[(2r)-1-amino-1-oxopropan-2-yl]amino]-4-oxobutanoic acid Chemical class NC(=O)[C@@H](C)NC(=O)[C@@H](N)CC(O)=O KNIZBZYMVRWQKN-DMTCNVIQSA-N 0.000 description 5
KZSNJWFQEVHDMF-SCSAIBSYSA-N D-valine Chemical compound CC(C)[C@@H](N)C(O)=O KZSNJWFQEVHDMF-SCSAIBSYSA-N 0.000 description 5
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 5
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
238000009835 boiling Methods 0.000 description 5
239000013078 crystal Substances 0.000 description 5
238000009472 formulation Methods 0.000 description 5
235000011852 gelatine desserts Nutrition 0.000 description 5
230000007935 neutral effect Effects 0.000 description 5
239000011591 potassium Substances 0.000 description 5
229910052700 potassium Inorganic materials 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
239000000376 reactant Substances 0.000 description 5
239000001632 sodium acetate Substances 0.000 description 5
235000017281 sodium acetate Nutrition 0.000 description 5
238000010561 standard procedure Methods 0.000 description 5
239000006188 syrup Substances 0.000 description 5
235000020357 syrup Nutrition 0.000 description 5
QVHJQCGUWFKTSE-RXMQYKEDSA-N (2r)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound OC(=O)[C@@H](C)NC(=O)OC(C)(C)C QVHJQCGUWFKTSE-RXMQYKEDSA-N 0.000 description 4
HQMLIDZJXVVKCW-UWTATZPHSA-N (2r)-2-aminopropanamide Chemical compound C[C@@H](N)C(N)=O HQMLIDZJXVVKCW-UWTATZPHSA-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
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 4
239000005695 Ammonium acetate Substances 0.000 description 4
101100037762 Caenorhabditis elegans rnh-2 gene Proteins 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
108010010803 Gelatin Proteins 0.000 description 4
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 4
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
244000290333 Vanilla fragrans Species 0.000 description 4
235000009499 Vanilla fragrans Nutrition 0.000 description 4
235000012036 Vanilla tahitensis Nutrition 0.000 description 4
238000005904 alkaline hydrolysis reaction Methods 0.000 description 4
235000019257 ammonium acetate Nutrition 0.000 description 4
229940043376 ammonium acetate Drugs 0.000 description 4
239000011575 calcium Substances 0.000 description 4
229910052791 calcium Inorganic materials 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
239000012230 colorless oil Substances 0.000 description 4
239000012141 concentrate Substances 0.000 description 4
BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 4
238000006114 decarboxylation reaction Methods 0.000 description 4
238000004821 distillation Methods 0.000 description 4
229950010030 dl-alanine Drugs 0.000 description 4
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IJCYIMAVKPGRJE-SECBINFHSA-N tert-butyl n-[(2r)-1-oxo-1-[(2,2,4,4-tetramethylthietan-3-yl)amino]propan-2-yl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@H](C)C(=O)NC1C(C)(C)SC1(C)C IJCYIMAVKPGRJE-SECBINFHSA-N 0.000 description 1
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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
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JLYXXMFPNIAWKQ-UHFFFAOYSA-N γ Benzene hexachloride Chemical compound ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 description 1