HRP960462A2 - Sweetener salts - Google Patents

Sweetener salts Download PDF

Info

Publication number: HRP960462A2
Authority: HR; Croatia
Prior art keywords: acid; salt; sweetening; derived; sweetener
Prior art date: 1995-10-11

Application number

HR09500836A

Other languages

English (en)

Croatian (hr)

Inventor

John Charles Fry

Jacob Van Soolingen

Original Assignee

Holland Sweetener Co

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.)

1995-10-11

Filing date

1996-10-09

Publication date

1998-02-28

1996-10-09 Application filed by Holland Sweetener Co filed Critical Holland Sweetener Co

1998-02-28 Publication of HRP960462A2 publication Critical patent/HRP960462A2/hr

Links

150000003839 salts Chemical class 0.000 title claims description 144
235000003599 food sweetener Nutrition 0.000 title claims description 59
239000003765 sweetening agent Substances 0.000 title claims description 59
238000000034 method Methods 0.000 claims description 111
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 claims description 88
239000002253 acid Substances 0.000 claims description 83
235000010357 aspartame Nutrition 0.000 claims description 80
239000000047 product Substances 0.000 claims description 70
230000008569 process Effects 0.000 claims description 65
239000007788 liquid Substances 0.000 claims description 60
239000002609 medium Substances 0.000 claims description 51
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 47
CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims description 43
235000003704 aspartic acid Nutrition 0.000 claims description 43
OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims description 43
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 38
239000007787 solid Substances 0.000 claims description 32
150000007524 organic acids Chemical class 0.000 claims description 29
238000002156 mixing Methods 0.000 claims description 20
238000002441 X-ray diffraction Methods 0.000 claims description 19
239000012736 aqueous medium Substances 0.000 claims description 19
239000000203 mixture Substances 0.000 claims description 18
108010011485 Aspartame Proteins 0.000 claims description 17
238000006243 chemical reaction Methods 0.000 claims description 17
239000000605 aspartame Substances 0.000 claims description 16
229960003438 aspartame Drugs 0.000 claims description 16
239000002244 precipitate Substances 0.000 claims description 16
238000002360 preparation method Methods 0.000 claims description 16
238000012986 modification Methods 0.000 claims description 15
230000004048 modification Effects 0.000 claims description 15
235000009508 confectionery Nutrition 0.000 claims description 13
239000013078 crystal Substances 0.000 claims description 13
229910017053 inorganic salt Inorganic materials 0.000 claims description 13
YGCFIWIQZPHFLU-UHFFFAOYSA-N acesulfame Chemical compound CC1=CC(=O)NS(=O)(=O)O1 YGCFIWIQZPHFLU-UHFFFAOYSA-N 0.000 claims description 11
229960005164 acesulfame Drugs 0.000 claims description 11
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 10
238000000354 decomposition reaction Methods 0.000 claims description 10
-1 organic acid salt Chemical class 0.000 claims description 9
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 claims description 9
239000011541 reaction mixture Substances 0.000 claims description 7
235000015218 chewing gum Nutrition 0.000 claims description 6
229940112822 chewing gum Drugs 0.000 claims description 6
235000013305 food Nutrition 0.000 claims description 6
239000011734 sodium Substances 0.000 claims description 6
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 claims description 5
229910000147 aluminium phosphate Inorganic materials 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
230000005855 radiation Effects 0.000 claims description 5
229910052708 sodium Inorganic materials 0.000 claims description 5
239000002904 solvent Substances 0.000 claims description 5
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
239000011575 calcium Substances 0.000 claims description 4
239000000625 cyclamic acid and its Na and Ca salt Substances 0.000 claims description 4
HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 claims description 4
238000010438 heat treatment Methods 0.000 claims description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 3
229910052791 calcium Inorganic materials 0.000 claims description 3
239000003495 polar organic solvent Substances 0.000 claims description 3
NUFKRGBSZPCGQB-FLBSXDLDSA-N (3s)-3-amino-4-oxo-4-[[(2r)-1-oxo-1-[(2,2,4,4-tetramethylthietan-3-yl)amino]propan-2-yl]amino]butanoic acid;pentahydrate Chemical compound O.O.O.O.O.OC(=O)C[C@H](N)C(=O)N[C@H](C)C(=O)NC1C(C)(C)SC1(C)C.OC(=O)C[C@H](N)C(=O)N[C@H](C)C(=O)NC1C(C)(C)SC1(C)C NUFKRGBSZPCGQB-FLBSXDLDSA-N 0.000 claims description 2
239000004377 Alitame Substances 0.000 claims description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
235000019409 alitame Nutrition 0.000 claims description 2
108010009985 alitame Proteins 0.000 claims description 2
238000002425 crystallisation Methods 0.000 claims description 2
230000008025 crystallization Effects 0.000 claims description 2
238000011065 in-situ storage Methods 0.000 claims description 2
229910052700 potassium Inorganic materials 0.000 claims description 2
239000011591 potassium Substances 0.000 claims description 2
239000012530 fluid Substances 0.000 claims 1
150000003512 tertiary amines Chemical class 0.000 claims 1
238000002474 experimental method Methods 0.000 description 50
239000000243 solution Substances 0.000 description 37
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
239000002002 slurry Substances 0.000 description 35
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
238000005160 1H NMR spectroscopy Methods 0.000 description 19
239000007858 starting material Substances 0.000 description 17
239000000126 substance Substances 0.000 description 17
230000000052 comparative effect Effects 0.000 description 12
235000005985 organic acids Nutrition 0.000 description 9
238000000926 separation method Methods 0.000 description 9
230000008901 benefit Effects 0.000 description 8
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 7
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
150000007513 acids Chemical class 0.000 description 6
238000004090 dissolution Methods 0.000 description 6
230000000694 effects Effects 0.000 description 6
239000011343 solid material Substances 0.000 description 6
239000012265 solid product Substances 0.000 description 6
238000003756 stirring Methods 0.000 description 6
CVHZOJJKTDOEJC-UHFFFAOYSA-M 1,1-dioxo-1,2-benzothiazol-3-olate Chemical compound C1=CC=C2C([O-])=NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-M 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
238000001914 filtration Methods 0.000 description 5
238000001694 spray drying Methods 0.000 description 5
238000009826 distribution Methods 0.000 description 4
238000001035 drying Methods 0.000 description 4
239000012467 final product Substances 0.000 description 4
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 4
WBZFUFAFFUEMEI-UHFFFAOYSA-M Acesulfame k Chemical compound [K+].CC1=CC(=O)[N-]S(=O)(=O)O1 WBZFUFAFFUEMEI-UHFFFAOYSA-M 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-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
102100036883 Cyclin-H Human genes 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
101000713120 Homo sapiens Cyclin-H Proteins 0.000 description 3
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
238000000576 coating method Methods 0.000 description 3
BCAARMUWIRURQS-UHFFFAOYSA-N dicalcium;oxocalcium;silicate Chemical compound [Ca+2].[Ca+2].[Ca]=O.[O-][Si]([O-])([O-])[O-] BCAARMUWIRURQS-UHFFFAOYSA-N 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
239000000796 flavoring agent Substances 0.000 description 3
235000019634 flavors Nutrition 0.000 description 3
229940043265 methyl isobutyl ketone Drugs 0.000 description 3
239000012452 mother liquor Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000002245 particle Substances 0.000 description 3
235000021395 porridge Nutrition 0.000 description 3
238000005204 segregation Methods 0.000 description 3
235000019640 taste Nutrition 0.000 description 3
238000010626 work up procedure Methods 0.000 description 3
KVHQNWGLVVERFR-ACMTZBLWSA-N (3s)-3-amino-4-[[(2s)-1-methoxy-1-oxo-3-phenylpropan-2-yl]amino]-4-oxobutanoic acid;6-methyl-2,2-dioxooxathiazin-4-one Chemical compound CC1=CC(=O)[NH2+]S(=O)(=O)O1.[O-]C(=O)C[C@H](N)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 KVHQNWGLVVERFR-ACMTZBLWSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
YZQCXOFQZKCETR-UWVGGRQHSA-N Asp-Phe Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C(O)=O)CC1=CC=CC=C1 YZQCXOFQZKCETR-UWVGGRQHSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
235000010358 acesulfame potassium Nutrition 0.000 description 2
239000000619 acesulfame-K Substances 0.000 description 2
108010069205 aspartyl-phenylalanine Proteins 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
239000011248 coating agent Substances 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
238000005516 engineering process Methods 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
230000002209 hydrophobic effect Effects 0.000 description 2
239000005457 ice water Substances 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
239000000843 powder Substances 0.000 description 2
238000003825 pressing Methods 0.000 description 2
235000019204 saccharin Nutrition 0.000 description 2
229940081974 saccharin Drugs 0.000 description 2
239000013049 sediment Substances 0.000 description 2
238000007086 side reaction Methods 0.000 description 2
238000012546 transfer Methods 0.000 description 2
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 2
238000005406 washing Methods 0.000 description 2
239000001993 wax Substances 0.000 description 2
WIQRFAVIEYRRBG-YFKPBYRVSA-N (3s)-3-amino-4-(1,3-dihydroxypropan-2-ylamino)-4-oxobutanoic acid Chemical class OC(=O)C[C@H](N)C(=O)NC(CO)CO WIQRFAVIEYRRBG-YFKPBYRVSA-N 0.000 description 1
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 description 1
NTQDELBZOMWXRS-RVJQKOHUSA-N (3s)-3-amino-4-[[(1r,2s)-1-carboxy-2-hydroxypropyl]amino]-4-oxobutanoic acid Chemical class C[C@H](O)[C@H](C(O)=O)NC(=O)[C@@H](N)CC(O)=O NTQDELBZOMWXRS-RVJQKOHUSA-N 0.000 description 1
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
PQVHMOLNSYFXIJ-UHFFFAOYSA-N 4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]pyrazole-3-carboxylic acid Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C(=NN(C=1)CC(N1CC2=C(CC1)NN=N2)=O)C(=O)O PQVHMOLNSYFXIJ-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
239000004385 Aspartame-acesulfame salt Substances 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
UDIPTWFVPPPURJ-UHFFFAOYSA-M Cyclamate Chemical compound [Na+].[O-]S(=O)(=O)NC1CCCCC1 UDIPTWFVPPPURJ-UHFFFAOYSA-M 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
206010013911 Dysgeusia Diseases 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
VTAJIXDZFCRWBR-UHFFFAOYSA-N Licoricesaponin B2 Natural products C1C(C2C(C3(CCC4(C)CCC(C)(CC4C3=CC2)C(O)=O)C)(C)CC2)(C)C2C(C)(C)CC1OC1OC(C(O)=O)C(O)C(O)C1OC1OC(C(O)=O)C(O)C(O)C1O VTAJIXDZFCRWBR-UHFFFAOYSA-N 0.000 description 1
102000004895 Lipoproteins Human genes 0.000 description 1
108090001030 Lipoproteins Proteins 0.000 description 1
239000012901 Milli-Q water Substances 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
238000013019 agitation Methods 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001335 aliphatic alkanes Chemical class 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
229960001504 aspartame acesulfame Drugs 0.000 description 1
235000019413 aspartame-acesulfame salt Nutrition 0.000 description 1
235000013871 bee wax Nutrition 0.000 description 1
239000012166 beeswax Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
235000019658 bitter taste Nutrition 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
230000008859 change Effects 0.000 description 1
238000012512 characterization method Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000005352 clarification Methods 0.000 description 1
239000000470 constituent Substances 0.000 description 1
238000012899 de-mixing Methods 0.000 description 1
235000011850 desserts Nutrition 0.000 description 1
235000005911 diet Nutrition 0.000 description 1
230000037213 diet Effects 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
238000009792 diffusion process Methods 0.000 description 1
238000007907 direct compression Methods 0.000 description 1
239000003480 eluent Substances 0.000 description 1
238000010931 ester hydrolysis Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
239000003925 fat Substances 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
230000008014 freezing Effects 0.000 description 1
238000007710 freezing Methods 0.000 description 1
229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
239000007789 gas Substances 0.000 description 1
LPLVUJXQOOQHMX-UHFFFAOYSA-N glycyrrhetinic acid glycoside Natural products C1CC(C2C(C3(CCC4(C)CCC(C)(CC4C3=CC2=O)C(O)=O)C)(C)CC2)(C)C2C(C)(C)C1OC1OC(C(O)=O)C(O)C(O)C1OC1OC(C(O)=O)C(O)C(O)C1O LPLVUJXQOOQHMX-UHFFFAOYSA-N 0.000 description 1
229960004949 glycyrrhizic acid Drugs 0.000 description 1
UYRUBYNTXSDKQT-UHFFFAOYSA-N glycyrrhizic acid Natural products CC1(C)C(CCC2(C)C1CCC3(C)C2C(=O)C=C4C5CC(C)(CCC5(C)CCC34C)C(=O)O)OC6OC(C(O)C(O)C6OC7OC(O)C(O)C(O)C7C(=O)O)C(=O)O UYRUBYNTXSDKQT-UHFFFAOYSA-N 0.000 description 1
239000001685 glycyrrhizic acid Substances 0.000 description 1
235000019410 glycyrrhizin Nutrition 0.000 description 1
LPLVUJXQOOQHMX-QWBHMCJMSA-N glycyrrhizinic acid Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@H](O[C@@H]1O[C@@H]1C([C@H]2[C@]([C@@H]3[C@@]([C@@]4(CC[C@@]5(C)CC[C@@](C)(C[C@H]5C4=CC3=O)C(O)=O)C)(C)CC2)(C)CC1)(C)C)C(O)=O)[C@@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O LPLVUJXQOOQHMX-QWBHMCJMSA-N 0.000 description 1
229910002804 graphite Inorganic materials 0.000 description 1
239000010439 graphite Substances 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
238000003384 imaging method Methods 0.000 description 1
238000002955 isolation Methods 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000008101 lactose Substances 0.000 description 1
238000005259 measurement Methods 0.000 description 1
229910000000 metal hydroxide Inorganic materials 0.000 description 1
150000004692 metal hydroxides Chemical class 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
239000012046 mixed solvent Substances 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
150000004028 organic sulfates Chemical class 0.000 description 1
230000002688 persistence Effects 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
BXRNXXXXHLBUKK-UHFFFAOYSA-N piperazine-2,5-dione Chemical compound O=C1CNC(=O)CN1 BXRNXXXXHLBUKK-UHFFFAOYSA-N 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
HEKURBKACCBNEJ-UHFFFAOYSA-M potassium;1,1-dioxo-1,2-benzothiazol-2-id-3-one Chemical compound [K+].C1=CC=C2C(=O)[N-]S(=O)(=O)C2=C1 HEKURBKACCBNEJ-UHFFFAOYSA-M 0.000 description 1
238000004321 preservation Methods 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000009467 reduction Effects 0.000 description 1
239000013558 reference substance Substances 0.000 description 1
230000002787 reinforcement Effects 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
238000010956 selective crystallization Methods 0.000 description 1
230000014860 sensory perception of taste Effects 0.000 description 1
229960001462 sodium cyclamate Drugs 0.000 description 1
235000014214 soft drink Nutrition 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
238000013112 stability test Methods 0.000 description 1
238000003860 storage Methods 0.000 description 1
IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 description 1
239000000725 suspension Substances 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
150000003626 triacylglycerols Chemical class 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
238000005550 wet granulation Methods 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/30—Artificial sweetening agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06104—Dipeptides with the first amino acid being acidic
- C07K5/06113—Asp- or Asn-amino acid
- C07K5/06121—Asp- or Asn-amino acid the second amino acid being aromatic or cycloaliphatic
- C07K5/0613—Aspartame
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/30—Artificial sweetening agents
- A23L27/31—Artificial sweetening agents containing amino acids, nucleotides, peptides or derivatives
- A23L27/32—Artificial sweetening agents containing amino acids, nucleotides, peptides or derivatives containing dipeptides or derivatives
- 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

Life Sciences & Earth Sciences (AREA)
Chemical & Material Sciences (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Health & Medical Sciences (AREA)
Polymers & Plastics (AREA)
Food Science & Technology (AREA)
Engineering & Computer Science (AREA)
Nutrition Science (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Medicinal Chemistry (AREA)
Genetics & Genomics (AREA)
Biophysics (AREA)
Biochemistry (AREA)
Seasonings (AREA)
Peptides Or Proteins (AREA)
Confectionery (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Medicinal Preparation (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

HR09500836A 1995-10-11 1996-10-09 Sweetener salts HRP960462A2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
BE9500836A BE1009660A3 (nl)	1995-10-11	1995-10-11	Zoetstofzouten.

Publications (1)

Publication Number	Publication Date
HRP960462A2 true HRP960462A2 (en)	1998-02-28

Family

ID=3889226

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HR09500836A HRP960462A2 (en)	1995-10-11	1996-10-09	Sweetener salts

Country Status (30)

Country	Link
US (1)	US5827562A (ru)
EP (1)	EP0768041B1 (ru)
JP (2)	JP4132108B2 (ru)
KR (1)	KR100441898B1 (ru)
CN (1)	CN1103558C (ru)
AR (1)	AR003857A1 (ru)
AT (1)	ATE229757T1 (ru)
AU (1)	AU711095B2 (ru)
BA (1)	BA96131A (ru)
BE (1)	BE1009660A3 (ru)
BG (1)	BG61928B1 (ru)
BR (1)	BR9605053A (ru)
CA (1)	CA2187502C (ru)
CO (1)	CO4750776A1 (ru)
CZ (1)	CZ298896A3 (ru)
DE (1)	DE69625437T2 (ru)
DK (1)	DK0768041T3 (ru)
EA (1)	EA000281B1 (ru)
ES (1)	ES2188715T3 (ru)
HR (1)	HRP960462A2 (ru)
HU (1)	HU216320B (ru)
IL (1)	IL119399A (ru)
NO (1)	NO964304L (ru)
NZ (1)	NZ299540A (ru)
PE (1)	PE26898A1 (ru)
PL (1)	PL184076B1 (ru)
TR (1)	TR199600808A1 (ru)
UA (1)	UA45335C2 (ru)
YU (1)	YU54996A (ru)
ZA (1)	ZA968567B (ru)

Families Citing this family (21)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH0882035A (ja) *	1994-09-06	1996-03-26	Kaneshin:Kk	木造住宅における階層間の天井装置
NL1003600C2 (nl) *	1996-07-16	1998-01-21	Holland Sweetener Co	Stabiele dipeptide-zoetstof bevattende suspensies in water.
NL1003606C2 (nl) *	1996-07-16	1998-01-21	Holland Sweetener Co	Dipeptide-zoetstof bevattende kauwgums met verlengde en verbeterde smaak.
NL1006243C2 (nl) *	1997-06-06	1998-12-08	Holland Sweetener Co	Werkwijze voor de bereiding van zouten van aspartaam uit N-beschermd aspartaam.
US6291004B1 (en) *	1997-09-11	2001-09-18	The Nutrasweet Company	Basic salts of n-[n-(3,3-dimethylbutyl)-l-α-aspartyl]-l-phenylalanine 1-methyl ester
US6129942A (en) *	1997-09-11	2000-10-10	The Nutrasweet Company	Sweetener salts of N-[N-(3,3-dimethylbutyl)-L-α-aspartyl]-L-phenylalanine 1-methyl ester
JP3648959B2 (ja) *	1997-12-22	2005-05-18	味の素株式会社	甘味料組成物
JP3646497B2 (ja) *	1997-12-22	2005-05-11	味の素株式会社	顆粒状甘味料
NL1009324C2 (nl) *	1998-06-05	1999-12-07	Holland Sweetener Co	Bereiding en zuivering van een organisch zout van aspartaam.
NL1009323C2 (nl) *	1998-06-05	1999-12-07	Holland Sweetener Co	Bereiding en zuivering van een organisch zout van aspartaam.
NL1015370C2 (nl) *	2000-05-31	2001-12-03	Holland Sweetener Co	Intensieve zoetstof op drager.
DE10330025A1 (de) *	2003-07-03	2005-01-20	Nutrinova Nutrition Specialties & Food Ingredients Gmbh	Verfahren zur Herstellung eines Süßstoffsalzes basierend auf Aspartam und Acesulfam
US9101160B2 (en)	2005-11-23	2015-08-11	The Coca-Cola Company	Condiments with high-potency sweetener
US8017168B2 (en)	2006-11-02	2011-09-13	The Coca-Cola Company	High-potency sweetener composition with rubisco protein, rubiscolin, rubiscolin derivatives, ace inhibitory peptides, and combinations thereof, and compositions sweetened therewith
CN101869256A (zh) *	2010-06-04	2010-10-27	上海师范大学	一种高倍甜味剂双甜的制备方法
CN102144769A (zh) *	2011-02-18	2011-08-10	上海师范大学	一种新型高倍甜味剂的制备方法
CN104719827A (zh) *	2015-02-14	2015-06-24	许建刚	天门冬氨酸衍生物与甜味酸的共结晶方法
CN104605219A (zh) *	2015-02-14	2015-05-13	姚洪齐	天门冬氨酸衍生物与甜味酸盐的共结晶方法
CN109535100A (zh) *	2018-12-26	2019-03-29	常茂生物化学工程股份有限公司	天门冬酰苯丙氨酸甲酯乙酰磺胺酸的制备方法
CN112174911A (zh) *	2020-11-17	2021-01-05	安徽维多食品配料有限公司	一种大颗粒双甜结晶方法
CN112321676B (zh) *	2020-12-12	2022-06-14	山东诚汇双达药业有限公司	一种纽甜的成盐方法

Family Cites Families (20)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2628294C3 (de) *	1976-06-24	1978-12-14	Hoechst Ag, 6000 Frankfurt	SUßstoffmischung mit verbessertem saccharoseähnlichem Geschmack
DE2001017C3 (de) *	1970-01-10	1978-05-18	Hoechst Ag, 6000 Frankfurt	3,4-Dihydro-1,23-oxathiazin-4on-2,2-dioxide, ihre Herstellung und Verwendung
US3922369A (en) *	1970-07-16	1975-11-25	Gen Foods Corp	Low calorie sweetening composition and method for making same
CA1027113A (en) *	1973-04-02	1978-02-28	General Foods Corporation	Sweetener solution containing saccharin and aspartane
FR2245299A1 (en) *	1973-08-17	1975-04-25	Gen Foods Corp	Artificial sweetening compsns - based on low alkyl esters of aspartylphenylalanine
DE2556109C2 (de) *	1975-12-12	1984-05-03	General Foods Corp., 10625 White Plains, N.Y.	Modifizierte Süßstoffe und Verfahren zum Modifizieren des anhaltend süssen Nachgeschmacks eines Süßstoffes
DE3271880D1 (en) *	1981-04-29	1986-08-07	Tate & Lyle Plc	Sweetening agents
SU1407388A3 (ru) *	1982-05-20	1988-06-30	Тейт Энд Лайл Паблик Лимитед Компани (Фирма)	Подслащивающа композици
US4439460A (en) *	1982-06-01	1984-03-27	G. D. Searle & Co.	Dipeptide sweetener sulfate and sulfonate salts
CA1220966A (en) *	1983-08-22	1987-04-28	Susan J. Pettigrew	Non-saccaride sweetened product
US4822635A (en) *	1985-04-15	1989-04-18	General Foods Corporation	Sweetening with L-aminodicarboxylic acid esters
ES8604766A1 (es) *	1985-09-20	1986-03-16	Palomo Coll Alberto	Procedimiento para la preparacion de nuevas sales fisiologi-camente activas o aceptables de sabor dulce
DK226887A (da) *	1986-08-21	1988-02-22	Suomen Sokeri Oy	Soedemiddel
DE3741961C1 (en) *	1987-12-10	1989-04-27	Wild Gmbh & Co Kg Rudolf	Sweetener, process for the production thereof and use thereof
US5164214A (en) *	1987-12-10	1992-11-17	Rudolf-Wild Gmbh & Co. Kg	Sweetening agent
US5114726A (en) *	1989-07-25	1992-05-19	The Nutrasweet Company	Process for preparing aspartame coated organic acid
US5106632A (en) *	1990-01-23	1992-04-21	Warner-Lambert Company	Enhanced sweetness of acesulfame-k in edible compositions
US5126158A (en) *	1990-08-07	1992-06-30	Pepsico Inc.	Beverage compositions comprising a dipetide sweetener, saccharin salt and hydrocolloidal polysaccharide
JP3409396B2 (ja) *	1993-11-19	2003-05-26	味の素株式会社	α−Ｌ−アスパルチル−Ｌ−フェニルアラニンメチルエステルの製造法
EP0733641A1 (en) *	1995-03-20	1996-09-25	Holland Sweetener Company V.O.F.	Method for crystallizing alpha-l-aspartyl-l-phenylalanine methyl ester

1995
- 1995-10-11 BE BE9500836A patent/BE1009660A3/nl not_active IP Right Cessation
1996
- 1996-09-23 DE DE69625437T patent/DE69625437T2/de not_active Expired - Lifetime
- 1996-09-23 EP EP96202655A patent/EP0768041B1/en not_active Expired - Lifetime
- 1996-09-23 AT AT96202655T patent/ATE229757T1/de not_active IP Right Cessation
- 1996-09-23 ES ES96202655T patent/ES2188715T3/es not_active Expired - Lifetime
- 1996-09-23 DK DK96202655T patent/DK0768041T3/da active
- 1996-09-24 PE PE1996000681A patent/PE26898A1/es not_active Application Discontinuation
- 1996-10-02 CO CO96052398A patent/CO4750776A1/es unknown
- 1996-10-02 AU AU67971/96A patent/AU711095B2/en not_active Expired
- 1996-10-09 NZ NZ299540A patent/NZ299540A/en unknown
- 1996-10-09 CA CA002187502A patent/CA2187502C/en not_active Expired - Lifetime
- 1996-10-09 HR HR09500836A patent/HRP960462A2/hr not_active Application Discontinuation
- 1996-10-10 UA UA96103877A patent/UA45335C2/uk unknown
- 1996-10-10 BA BA960131A patent/BA96131A/bs unknown
- 1996-10-10 NO NO964304A patent/NO964304L/no not_active Application Discontinuation
- 1996-10-10 US US08/728,594 patent/US5827562A/en not_active Expired - Lifetime
- 1996-10-10 IL IL11939996A patent/IL119399A/xx not_active IP Right Cessation
- 1996-10-10 CN CN96119241A patent/CN1103558C/zh not_active Expired - Lifetime
- 1996-10-10 KR KR1019960046011A patent/KR100441898B1/ko not_active IP Right Cessation
- 1996-10-10 ZA ZA968567A patent/ZA968567B/xx unknown
- 1996-10-10 BG BG100901A patent/BG61928B1/bg unknown
- 1996-10-10 BR BR9605053A patent/BR9605053A/pt not_active IP Right Cessation
- 1996-10-10 PL PL96316473A patent/PL184076B1/pl unknown
- 1996-10-10 EA EA199600081A patent/EA000281B1/ru not_active IP Right Cessation
- 1996-10-10 HU HU9602785A patent/HU216320B/hu not_active IP Right Cessation
- 1996-10-10 YU YU54996A patent/YU54996A/sh unknown
- 1996-10-11 TR TR96/00808A patent/TR199600808A1/xx unknown
- 1996-10-11 AR ARP960104704A patent/AR003857A1/es unknown
- 1996-10-11 CZ CZ962988A patent/CZ298896A3/cs unknown
- 1996-10-11 JP JP26979696A patent/JP4132108B2/ja not_active Expired - Lifetime
2007
- 2007-05-15 JP JP2007129793A patent/JP4134244B2/ja not_active Expired - Lifetime

Also Published As

Publication number	Publication date
PL184076B1 (pl)	2002-08-30
PE26898A1 (es)	1998-06-20
NZ299540A (en)	1997-09-22
EP0768041B1 (en)	2002-12-18
ZA968567B (en)	1997-05-13
US5827562A (en)	1998-10-27
ATE229757T1 (de)	2003-01-15
KR970019890A (ko)	1997-05-28
JP2007209351A (ja)	2007-08-23
EA000281B1 (ru)	1999-02-25
DK0768041T3 (da)	2003-04-14
NO964304D0 (no)	1996-10-10
BG61928B1 (bg)	1998-10-30
HU216320B (hu)	1999-06-28
KR100441898B1 (ko)	2004-09-30
EA199600081A1 (ru)	1997-06-30
BA96131A (bs)	1998-12-28
IL119399A (en)	2000-01-31
BG100901A (en)	1997-08-29
CA2187502C (en)	2005-01-04
JPH09271350A (ja)	1997-10-21
BE1009660A3 (nl)	1997-06-03
MX9604789A (es)	1998-07-31
AR003857A1 (es)	1998-09-09
JP4134244B2 (ja)	2008-08-20
CA2187502A1 (en)	1997-04-12
DE69625437D1 (de)	2003-01-30
ES2188715T3 (es)	2003-07-01
HUP9602785A2 (en)	1997-05-28
TR199600808A1 (tr)	1997-04-22
NO964304L (no)	1997-04-14
EP0768041A1 (en)	1997-04-16
IL119399A0 (en)	1997-01-10
CO4750776A1 (es)	1999-03-31
UA45335C2 (uk)	2002-04-15
PL316473A1 (en)	1997-04-14
AU6797196A (en)	1997-04-17
BR9605053A (pt)	1998-06-30
JP4132108B2 (ja)	2008-08-13
AU711095B2 (en)	1999-10-07
YU54996A (sh)	1998-11-05
HUP9602785A3 (en)	1998-04-28
CN1155995A (zh)	1997-08-06
DE69625437T2 (de)	2003-10-23
HU9602785D0 (en)	1996-11-28
CZ298896A3 (en)	1997-04-16
CN1103558C (zh)	2003-03-26

Publication	Publication Date	Title
HRP960462A2 (en)	1998-02-28	Sweetener salts
JP4991091B2 (ja)	2012-08-01	モナティンの非天然型立体異性体塩の結晶及びその使用
JPS58162262A (ja)	1983-09-26	ジペプチド甘味料−金属複合体
WO2001010241A2 (en)	2001-02-15	PROCESS FOR COATING N-[N-(3,3-DIMETHYLBUTYL)-L-α-ASPARTYL]-L-PHENYLALANINE 1-METHYL ESTER ONTO A CARRIER
US5733883A (en)	1998-03-31	Crystallization of α-L-aspartyl-L-phenylalanine methyl ester from aqueous solution
JPH0377199B2 (ru)	1991-12-09
Füredi-Milhofer et al.	1999	Crystallization from microemulsions–a novel method for the preparation of new crystal forms of aspartame
JPH0412105B2 (ru)	1992-03-03
JP2002517511A (ja)	2002-06-18	アスパルテームの有機塩の製造法および精製法
JPH0327398A (ja)	1991-02-05	α―Ｌ―アスパルチル―Ｌ―フェニルアラニンメチルエステルの晶析方法
JP2002517510A (ja)	2002-06-18	アスパルテームの有機塩の製造法
US6294686B1 (en)	2001-09-25	Aspartame crystals and process for the preparation thereof
US6096362A (en)	2000-08-01	Stable suspensions containing dipeptide sweetener in water
MXPA96004789A (en)	1998-11-09	Sales edulcoran
NL1006243C2 (nl)	1998-12-08	Werkwijze voor de bereiding van zouten van aspartaam uit N-beschermd aspartaam.
JPH1059924A (ja)	1998-03-03	固体タウリンおよびその製造方法
WO1993002100A1 (en)	1993-02-04	Method for crystallizing alpha-l-aspartyl-l-phenylalanine methyl ester
MXPA96002537A (en)	1998-01-01	Crystallization of methyl ester of alpha-l-aspartil-l-phenylalanin starting from aqua solutions
JPH0285294A (ja)	1990-03-26	溶解性の改良されたα―Ｌ―アスパルチル―Ｌ―フエニルアラニンメチルエステルの製造法

Legal Events

Date	Code	Title	Description
1998-02-28	A1OB	Publication of a patent application
1998-06-03	AIPI	Request for the grant of a patent on the basis of a substantive examination of a patent application
2001-10-09	ODRP	Renewal fee for the maintenance of a patent	Payment date: 20011009 Year of fee payment: 6
2003-02-14	ODBC	Application rejected