JPH01138202A - Preparation of cyclodextrin having high solubility - Google Patents
Preparation of cyclodextrin having high solubilityInfo
- Publication number
- JPH01138202A JPH01138202A JP29529887A JP29529887A JPH01138202A JP H01138202 A JPH01138202 A JP H01138202A JP 29529887 A JP29529887 A JP 29529887A JP 29529887 A JP29529887 A JP 29529887A JP H01138202 A JPH01138202 A JP H01138202A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- cyclodextrin
- mixture
- starch
- decomposition product
- Prior art date
- 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.)
- Granted
Links
- 229920000858 Cyclodextrin Polymers 0.000 title claims abstract description 13
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 title claims abstract description 11
- 229920002472 Starch Polymers 0.000 claims abstract description 19
- 235000019698 starch Nutrition 0.000 claims abstract description 19
- 239000008107 starch Substances 0.000 claims abstract description 18
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims abstract description 16
- 238000000354 decomposition reaction Methods 0.000 claims abstract description 15
- 239000000203 mixture Substances 0.000 claims abstract description 14
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims abstract description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 9
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims abstract description 9
- 239000008103 glucose Substances 0.000 claims abstract description 9
- 239000001530 fumaric acid Substances 0.000 claims abstract description 8
- 238000010306 acid treatment Methods 0.000 claims abstract description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims abstract description 6
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims abstract description 5
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 claims abstract description 4
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 claims abstract description 4
- 229920001353 Dextrin Polymers 0.000 claims abstract description 3
- 239000004375 Dextrin Substances 0.000 claims abstract description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims abstract description 3
- GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 claims abstract description 3
- 235000019425 dextrin Nutrition 0.000 claims abstract description 3
- DBTMGCOVALSLOR-UHFFFAOYSA-N 32-alpha-galactosyl-3-alpha-galactosyl-galactose Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(OC2C(C(CO)OC(O)C2O)O)OC(CO)C1O DBTMGCOVALSLOR-UHFFFAOYSA-N 0.000 claims abstract 2
- RXVWSYJTUUKTEA-UHFFFAOYSA-N D-maltotriose Natural products OC1C(O)C(OC(C(O)CO)C(O)C(O)C=O)OC(CO)C1OC1C(O)C(O)C(O)C(CO)O1 RXVWSYJTUUKTEA-UHFFFAOYSA-N 0.000 claims abstract 2
- FYGDTMLNYKFZSV-UHFFFAOYSA-N mannotriose Natural products OC1C(O)C(O)C(CO)OC1OC1C(CO)OC(OC2C(OC(O)C(O)C2O)CO)C(O)C1O FYGDTMLNYKFZSV-UHFFFAOYSA-N 0.000 claims abstract 2
- FYGDTMLNYKFZSV-BYLHFPJWSA-N β-1,4-galactotrioside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@H](CO)O[C@@H](O[C@@H]2[C@@H](O[C@@H](O)[C@H](O)[C@H]2O)CO)[C@H](O)[C@H]1O FYGDTMLNYKFZSV-BYLHFPJWSA-N 0.000 claims abstract 2
- HFHDHCJBZVLPGP-RWMJIURBSA-N alpha-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO HFHDHCJBZVLPGP-RWMJIURBSA-N 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 8
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 6
- 150000007524 organic acids Chemical class 0.000 claims description 5
- 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 claims description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 4
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 3
- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 claims description 3
- 239000011975 tartaric acid Substances 0.000 claims description 3
- 235000002906 tartaric acid Nutrition 0.000 claims description 3
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims description 2
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 claims description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 2
- FTNIPWXXIGNQQF-UHFFFAOYSA-N UNPD130147 Natural products OC1C(O)C(O)C(CO)OC1OC1C(CO)OC(OC2C(OC(OC3C(OC(OC4C(OC(O)C(O)C4O)CO)C(O)C3O)CO)C(O)C2O)CO)C(O)C1O FTNIPWXXIGNQQF-UHFFFAOYSA-N 0.000 claims description 2
- LUEWUZLMQUOBSB-UHFFFAOYSA-N UNPD55895 Natural products OC1C(O)C(O)C(CO)OC1OC1C(CO)OC(OC2C(OC(OC3C(OC(O)C(O)C3O)CO)C(O)C2O)CO)C(O)C1O LUEWUZLMQUOBSB-UHFFFAOYSA-N 0.000 claims description 2
- 235000011054 acetic acid Nutrition 0.000 claims description 2
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims description 2
- OCIBBXPLUVYKCH-QXVNYKTNSA-N alpha-maltohexaose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)O[C@H](O[C@@H]2[C@H](O[C@H](O[C@@H]3[C@H](O[C@H](O[C@@H]4[C@H](O[C@H](O[C@@H]5[C@H](O[C@H](O)[C@H](O)[C@H]5O)CO)[C@H](O)[C@H]4O)CO)[C@H](O)[C@H]3O)CO)[C@H](O)[C@H]2O)CO)[C@H](O)[C@H]1O OCIBBXPLUVYKCH-QXVNYKTNSA-N 0.000 claims description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 2
- 235000015165 citric acid Nutrition 0.000 claims description 2
- 235000011087 fumaric acid Nutrition 0.000 claims description 2
- GDSRMADSINPKSL-HSEONFRVSA-N gamma-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO GDSRMADSINPKSL-HSEONFRVSA-N 0.000 claims description 2
- 239000000174 gluconic acid Substances 0.000 claims description 2
- 235000012208 gluconic acid Nutrition 0.000 claims description 2
- 239000004310 lactic acid Substances 0.000 claims description 2
- 235000014655 lactic acid Nutrition 0.000 claims description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 2
- 239000011976 maleic acid Substances 0.000 claims description 2
- 239000001630 malic acid Substances 0.000 claims description 2
- 235000011090 malic acid Nutrition 0.000 claims description 2
- DJMVHSOAUQHPSN-UHFFFAOYSA-N malto-hexaose Natural products OC1C(O)C(OC(C(O)CO)C(O)C(O)C=O)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(OC4C(C(O)C(O)C(CO)O4)O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 DJMVHSOAUQHPSN-UHFFFAOYSA-N 0.000 claims description 2
- FJCUPROCOFFUSR-UHFFFAOYSA-N malto-pentaose Natural products OC1C(O)C(OC(C(O)CO)C(O)C(O)C=O)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 FJCUPROCOFFUSR-UHFFFAOYSA-N 0.000 claims description 2
- UYQJCPNSAVWAFU-UHFFFAOYSA-N malto-tetraose Natural products OC1C(O)C(OC(C(O)CO)C(O)C(O)C=O)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(O)C(CO)O2)O)C(CO)O1 UYQJCPNSAVWAFU-UHFFFAOYSA-N 0.000 claims description 2
- FJCUPROCOFFUSR-GMMZZHHDSA-N maltopentaose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O[C@H]([C@H](O)CO)[C@H](O)[C@@H](O)C=O)O[C@H](CO)[C@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@H](O[C@@H]2[C@@H]([C@@H](O)[C@H](O[C@@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O)[C@@H](CO)O2)O)[C@@H](CO)O1 FJCUPROCOFFUSR-GMMZZHHDSA-N 0.000 claims description 2
- LUEWUZLMQUOBSB-OUBHKODOSA-N maltotetraose Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@H](CO)O[C@@H](O[C@@H]2[C@@H](O[C@@H](O[C@@H]3[C@@H](O[C@@H](O)[C@H](O)[C@H]3O)CO)[C@H](O)[C@H]2O)CO)[C@H](O)[C@H]1O LUEWUZLMQUOBSB-OUBHKODOSA-N 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 235000006408 oxalic acid Nutrition 0.000 claims description 2
- 235000019260 propionic acid Nutrition 0.000 claims description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- 229920001450 Alpha-Cyclodextrin Polymers 0.000 claims 1
- FYGDTMLNYKFZSV-DZOUCCHMSA-N alpha-D-Glcp-(1->4)-alpha-D-Glcp-(1->4)-D-Glcp Chemical group O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)O[C@H](O[C@@H]2[C@H](OC(O)[C@H](O)[C@H]2O)CO)[C@H](O)[C@H]1O FYGDTMLNYKFZSV-DZOUCCHMSA-N 0.000 claims 1
- 229940043377 alpha-cyclodextrin Drugs 0.000 claims 1
- 229960004853 betadex Drugs 0.000 claims 1
- 229940080345 gamma-cyclodextrin Drugs 0.000 claims 1
- 235000011007 phosphoric acid Nutrition 0.000 claims 1
- 239000002253 acid Substances 0.000 abstract description 17
- 235000013305 food Nutrition 0.000 abstract description 4
- 239000002537 cosmetic Substances 0.000 abstract description 3
- 239000002304 perfume Substances 0.000 abstract 1
- 238000005063 solubilization Methods 0.000 abstract 1
- 230000007928 solubilization Effects 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 16
- 239000000047 product Substances 0.000 description 15
- 238000000034 method Methods 0.000 description 10
- 238000006482 condensation reaction Methods 0.000 description 4
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 4
- 108090000790 Enzymes Proteins 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 238000006911 enzymatic reaction Methods 0.000 description 3
- 229920001542 oligosaccharide Polymers 0.000 description 3
- 235000005985 organic acids Nutrition 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 240000005979 Hordeum vulgare Species 0.000 description 2
- 235000007340 Hordeum vulgare Nutrition 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- 235000013373 food additive Nutrition 0.000 description 2
- 239000002778 food additive Substances 0.000 description 2
- 239000003205 fragrance Substances 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 150000002482 oligosaccharides Chemical class 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- 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 1
- -1 @acid Chemical compound 0.000 description 1
- 241000186000 Bifidobacterium Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 244000017020 Ipomoea batatas Species 0.000 description 1
- 235000002678 Ipomoea batatas Nutrition 0.000 description 1
- 208000008589 Obesity Diseases 0.000 description 1
- 229920005654 Sephadex Polymers 0.000 description 1
- 239000012507 Sephadex™ Substances 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical group N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 description 1
- 108090000637 alpha-Amylases Proteins 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000003102 growth factor Substances 0.000 description 1
- 235000013402 health food Nutrition 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 210000003127 knee Anatomy 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 150000002772 monosaccharides Chemical class 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 230000036962 time dependent Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、溶解性の高いサイクロデキストリンの製造方
法に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to a method for producing highly soluble cyclodextrin.
サイクロデキストリン（以下、ｒｃＤＪと略記する。）
はグルコースが６個以上環状にα−１，４結合したオリ
ゴ糖であり、６個のグルコース単位からなるα−ＣＤ、
７個のグルコース単位からなるβ−ＣＤ、８１ＩＩのグ
ルコース単位からなるｒ−ＣＤが主として知られている
。Cyclodextrin (hereinafter abbreviated as rcDJ)
is an oligosaccharide in which 6 or more glucose units are cyclically α-1,4-linked, and α-CD consists of 6 glucose units,
β-CD consisting of 7 glucose units and r-CD consisting of 81II glucose units are mainly known.
ＣＤには、その構造上、分子に空洞があり、しかもこの
空洞が疎水性であるため、各種油性物質を取り込む性質
がある。Due to its structure, CD has a cavity in its molecule, and since this cavity is hydrophobic, it has the property of taking in various oily substances.
ＣＤはこのような性質を有しているために、幅広い用途
があり、製薬工業、化粧品工業、香料工業９食品工業な
との分野において応用研究が活発に進められている。Because CD has such properties, it has a wide range of uses, and applied research is being actively carried out in fields such as the pharmaceutical industry, cosmetics industry, fragrance industry, and food industry.
しかし、ＣＤの溶解度は低く、α−ＣＤ’″１４、β−
ＣＤで２．７−− ＣＤで２３程度である。特にβ−Ｃ
Ｄの溶解度は低く、実用化の場合には不利な性質である
。However, the solubility of CD is low, α-CD′″14, β-
CD is about 2.7--CD is about 23. Especially β-C
The solubility of D is low, which is a disadvantageous property for practical use.
最近、小林らによって分岐ＣＤの研究が進められ、その
性質が明らかにされたく小林ら、澱粉科学、３０．２３
１〜２３９ （１９８３） ）。たとえば溶解度につい
ては、分岐ＣＤの溶解度は元のＣＤの１０倍にも達する
。Recently, research on branched CD has been carried out by Kobayashi et al., and their properties have been clarified.Kobayashi et al., Starch Science, 30.23
1-239 (1983)). For example, in terms of solubility, the solubility of branched CDs is up to 10 times that of the original CD.
分岐ＣＤは澱粉から製造する方法とＣＤとオリゴ糖を混
合し、その混合物にプルラナーゼを作用させ、逆反応を
利用して製造する方法が知られている。前者の方法は澱
粉分子の核部分を巻き込んで環上反応を行なわせるもの
であり、酵素反応を二回以上行なわせるなと、煩雑な操
作を必要とする。また、１身者は大量の酵素を必要とし
、高濃度基質を用い、反応時間が長いなど、コスト低減
化に不利な面が多い。Branched CDs are known to be produced from starch, and by mixing CDs and oligosaccharides, applying pullulanase to the mixture, and using a reverse reaction. The former method involves involving the core part of the starch molecule to carry out a ring reaction, and requires complicated operations such as not allowing the enzymatic reaction to be carried out more than once. In addition, single-body methods require a large amount of enzyme, use highly concentrated substrates, and take a long reaction time, which are disadvantageous to cost reduction.
しかし、これまで酵素による枝付は以外の方法でＣＤに
枝をはけ、ＣＤの物性を改良した列は知られていない。However, until now, no method other than enzymatic branching has been known to improve the physical properties of CDs by branching them.
従来の酵素を用いた分岐ＣＤの製造と製品の高溶解性は
、各方面から注目されているが、本発明では、可及的低
コストで安全性の高い製品の開発を目的として１に来と
は全く異なった観点から、ＣＤと澱粉分解物を混合し、
主として食品添加物として認められている酸を触媒とし
て用い、ＣＤの物性改良を試みた。The production of branched CD using conventional enzymes and the high solubility of the product have been attracting attention from various quarters, but in the present invention, we have focused on the production of branched CDs using conventional enzymes with the aim of developing products with high safety at the lowest possible cost. From a completely different perspective, mixing CD and starch decomposition products,
We attempted to improve the physical properties of CD by using acids, which are mainly recognized as food additives, as catalysts.
そこで本発明者らはＣＤと澱粉分解物の酸縮合反応を鋭
意検討し、高温、減圧下で、フマル酸なとのａ品用有機
酸をＣＤと澱粉分解物の混合物中に加えて処理すること
により、各ｆ！の技がＣＤ環に付き、製品の溶解性が高
まることを見出し、実用性の高いＣＤの物性改良法を完
成したのである。Therefore, the present inventors intensively investigated the acid condensation reaction between CD and starch decomposition products, and treated the mixture by adding a grade organic acid such as fumaric acid to the mixture of CD and starch decomposition products at high temperature and under reduced pressure. By doing so, each f! By applying this technique to CD rings, he discovered that the solubility of the product increased, and completed a highly practical method for improving the physical properties of CD.
本発明は、ＣＤと澱粉分解物を混合し、酸処理を１〒な
うことを特徴とする溶解性の高いＣＤの製造方法を提供
するものである。The present invention provides a method for producing CD with high solubility, which is characterized by mixing CD and starch decomposition product and subjecting the mixture to acid treatment once.
澱粉分解物としてはグルコースのほかマル）−ス、マル
ｌ−）リオース、マルトテトラオース、マルトペンタオ
ース、マルトヘキサオースなとのマルトオリゴ糖、デキ
ストリンなどがあり、これらを単独または混合物の状態
で用いることが出来る。In addition to glucose, starch decomposition products include maltooligosaccharides such as mal)-s, mall-)liose, maltotetraose, maltopentaose, and maltohexaose, and dextrin, which are used alone or in a mixture. I can do it.
ＣＤとしては非分岐ＣＤ、分岐ＣＤいずれても良いが、
経済的には通常のα−ＣＤ、β−ＣＤ、γ−ＣＤのいず
れか、またはこれら二種以上の混合物、さらには市販さ
れているＣＤ製品、例えばＣＤを５０％含むＣＤ扮アメ
なども用いることができる。The CD may be either a non-branched CD or a branched CD, but
Economically, any one of ordinary α-CD, β-CD, and γ-CD, or a mixture of two or more of these, or a commercially available CD product, such as a CD disguise candy containing 50% CD, may be used. be able to.
酸としては、酢酸、シュウ酸、プロピオン酸。Acids include acetic acid, oxalic acid, and propionic acid.
乳酸、マレイン酸、フマル酸、コハク酸、リンゴ酸、酒
石酸、クエン酸およびグルコン酸なとの有機酸の他、塩
酸、＠酸、リン酸などの無機酸も利用できる。有機酸に
はこの他、ギ酸、酪酸も吏用可能てあり、条件によって
はアミノ酸も利用できる。＠を選択する場合、不快臭、
安定性なとの面から目的に適合した酸を選択すべきであ
る。In addition to organic acids such as lactic acid, maleic acid, fumaric acid, succinic acid, malic acid, tartaric acid, citric acid, and gluconic acid, inorganic acids such as hydrochloric acid, @acid, and phosphoric acid can also be used. In addition to these organic acids, formic acid and butyric acid can also be used, and depending on the conditions, amino acids can also be used. If you select @, unpleasant odor,
An acid suitable for the purpose should be selected in terms of stability.
ＣＤと澱粉分解物の混合割合については適宜決定すれば
よいが、通常はＣＤ １００重量部に対し澱粉分解物１
０〜１００瓜員部の割合とすればよい。The mixing ratio of CD and starch decomposition product may be determined as appropriate, but usually 1 part of starch decomposition product is mixed with 100 parts by weight of CD.
The ratio may be 0 to 100 melon parts.
澱粉分解物用の原料澱粉としては、馬鈴薯、甘藷、トウ
モロコシ、モチトウモロコシ、大麦、小麦、クビオカな
との１壬童の原料から得られる物を使用することができ
る。しかし、これらの澱粉から１与られる分解物はマル
トオリゴ糖より巨大な分子てあっても、酵素反応と異な
り、酸縮合反応であるため効率よく縮合がｉテなわれる
。しかし、マルトオリゴ糖より巨大な分子では、得られ
る反応物の溶解度はあまり上昇しないので、高溶解性製
品生産用にはマルトオリゴ糖が好ましい。As the raw material starch for the starch decomposition product, those obtained from raw materials such as potato, sweet potato, corn, waxy corn, barley, wheat, and Kubioka can be used. However, even though the decomposition products obtained from these starches have larger molecules than maltooligosaccharides, unlike enzymatic reactions, they are acid condensation reactions, so condensation is carried out efficiently. However, molecules larger than maltooligosaccharides do not significantly increase the solubility of the resulting reactants, so maltooligosaccharides are preferred for producing highly soluble products.
次に、酸としては食品添加物として認められている有機
酸が好ましいが、いずれの酸も１史用することができる
。また、酸を過剰に加えると、縮合反応が進みすぎ巨大
分子となるので、溶解度を上昇させることが困難となる
。酸の添加量は反応温度と時間により異なるが、通常Ｃ
Ｄと澱粉分解物の総重量に対し５〜３０％、好ましくは
１０〜２０％が適当である。Next, as the acid, organic acids that are recognized as food additives are preferred, but any acid can be used. Furthermore, if too much acid is added, the condensation reaction will proceed too much and form a macromolecule, making it difficult to increase the solubility. The amount of acid added varies depending on the reaction temperature and time, but is usually C
An appropriate amount is 5 to 30%, preferably 10 to 20%, based on the total weight of D and the starch decomposition product.
反応温度は用いる酸の安定性によって異なり、最適な温
度を選択すべきであるが、通常１３５〜３００℃の範囲
であれば反応は進行し、例えばフマル酸を用いる場合、
＋６０’Ｃ程度で充分である。The reaction temperature varies depending on the stability of the acid used, and the optimum temperature should be selected, but the reaction usually proceeds within the range of 135 to 300°C. For example, when using fumaric acid,
A temperature of about +60'C is sufficient.
真空度は特に限定する必要はなく、着色が強くなる場合
は真空度を上げろか、または炭酸ガス置換をすることが
望ましいが、通常２０〜７５５ ｍｍＨｇで反応する。The degree of vacuum does not need to be particularly limited, and if the coloring becomes strong, it is desirable to increase the degree of vacuum or replace the reaction with carbon dioxide gas, but the reaction is usually carried out at 20 to 755 mmHg.
本発明の方法によれば、グルコースやマルトースが結合
した分岐ＣＤ以外に各１糖が生成している。溶解度が上
昇するのは、ＣＤ環にグルコースまたはグルコース１１
でリマーがαおよび／またはβ結合した分岐ＣＤ、また
はＣＤ閏にマルトオリゴ糖が架橋した糖等が生成してい
るためと思われる。According to the method of the present invention, monosaccharides are produced in addition to branched CDs to which glucose and maltose are bonded. The solubility increases due to glucose or glucose 11 in the CD ring.
This is thought to be due to the formation of branched CDs with α and/or β linkages of remers, or sugars with malto-oligosaccharides cross-linked to CD anchors.
次に本発明の実施例を示す。 Next, examples of the present invention will be shown.
実施例１
ａ−ＣＤ２．５ｚとグルコース０．５ｇにフマル酸を０
．０１〜５．０ ｇ添加し、温度１１３０℃、圧カフ４
０ ｍ１１８で１７時間反応させ、酸の添加量の影響を
調へた。その結果を表−１に示す。Example 1 a-CD2.5z and glucose 0.5g with 0 fumaric acid
．． Add 01-5.0 g, temperature 1130℃, pressure cuff 4
The reaction was carried out at 0 mL 118 for 17 hours, and the influence of the amount of acid added was investigated. The results are shown in Table-1.
広しニー１ 故１ａ１皿に立り−・ コ ｏ、ｏｉ 。wide knee 1 Standing on the late 1a1 plate... o, oi.
Ｏ，１３４，６
０，２４９，１
０，５６２，３
０，６４８，６
０，８３６，１
３，０３３，３
５，０３＋、５
ＣＤ変換率の分析は高速液体クロマトグラフィー （Ｈ
ＰＬＣ）を用いてｊテなフた。なお、ＨＰＬＣの条件は
島津「ＬＣ−４ＡＪ 、水溶出、流速０．５ ｍｌ／ｍ
ｉ ｎ 、検出ＲＩ ： ＡｔＬｅｎＬＩａＬＩＯＩ
＋ １６Ｘ 、カラム：Ｂ１０−Ｒａｄ Ａｍ１ｎｅｘ
Ｃａｒｂｏｈｙｄｒａｔｅ ＨＰＸ−４２Ａであり・
二の条件下での各糖の保持時間（ＩＩＩｉｎ）は表−２
に示したとおりである。表中、例えばＧ１−α−ＣＤは
グルコシル−α−ＣＤを、Ｇ２−α−ＣＤはマルトシル
−α−ＣＤを意味する。O,134,6 0,249,1 0,562,3 0,648,6 0,836,1 3,033,3 5,03+,5 CD conversion rate analysis was performed using high performance liquid chromatography (H
PLC) The HPLC conditions were Shimadzu's LC-4AJ, water elution, flow rate 0.5 ml/m.
i n , detection RI: AtLenLIaLIOI
+ 16X, column: B10-Rad Am1nex
Carbohydrate HPX-42A
Table 2 shows the retention time (IIIin) of each sugar under the second condition.
As shown in In the table, for example, G1-α-CD means glucosyl-α-CD, and G2-α-CD means maltosyl-α-CD.
型乏−二二二２−
Ｇ ２− α −ＣＤ ８．３． Ｇ
電−β −ＣＤ ＋２．１゜Ｇ１−α−ＣＤ
８．９． Ｇ２ １４．５゜ｃｔ−ＣＤ
９．７． Ｇｌ １Ｇ、６゜Ｇ
２−β−ＣＤ １１．６． β−ＣＤ １９
．１実施例２
α−ＣＤ １．５ ｇとマルトース０．５ｇにフマル酸
０゜１ｇ添加し、温度＋１３０’Ｃ，圧力（３６０ｍｍ
１１ｇで反応させ、経時変１ヒを調べた。その結果を表
−３に示す。Type oligo-2222- G 2- α -CD 8.3. G
Electron-β-CD +2.1゜G1-α-CD
8.9. G2 14.5゜ct-CD
9.7. Gl 1G, 6゜G
2-β-CD 11.6. β-CD19
．． 1 Example 2 0.1 g of fumaric acid was added to 1.5 g of α-CD and 0.5 g of maltose, and the mixture was heated at +130'C and pressure (360 mm).
The reaction was carried out with 11 g, and the time-dependent changes were investigated. The results are shown in Table-3.
ギ１：＝二≦１
時間（Ｈ） ＣＤ変填率（％）０．３
０２
４．２４１８．７
８ １９．２以
上のように、本発明の方法は酵素反応法と比較して、反
応時間が４時間程でよく、非常に短時間に終了する。Gi1:=2≦1 Time (H) CD change rate (%) 0.3
02
4.2418.7 8 19.2 As mentioned above, the method of the present invention requires only about 4 hours of reaction time and is completed in a very short time compared to the enzyme reaction method.
実施例３
α−ＣＤ２．５ｇとグルコース０．５ ｇに各種酸を適
当量添加し、温度１６０℃、圧カフ４０ ｖｗＨｇで１
７時間反応させた。その結果を表４に示す。Example 3 Appropriate amounts of various acids were added to 2.5 g of α-CD and 0.5 g of glucose, and the mixture was incubated at a temperature of 160°C and a pressure cuff of 40 vwHg.
The reaction was allowed to proceed for 7 hours. The results are shown in Table 4.
型乏−コニー↓エ
フマル酸 ０．５ ６２．７コハク酸
０．１ ３２．１酒石酸
０．２ ２９．３実施例４
α−ＣＤ １．５ ｇとグルコース０．５ｇにフマル酸
０゜５８を添加し、温度１６０℃、圧力６ＧＯｍｍＨｇ
で１７時間反応させた。この時の反応前１麦のクロマト
グラムを第１図に示す。この時のＣＤ変換率は４８．５
％であった。Type poor-cony↓efmaric acid 0.5 62.7 Succinic acid 0.1 32.1 Tartaric acid
0.2 29.3 Example 4 Fumaric acid 0°58 was added to 1.5 g of α-CD and 0.5 g of glucose, and the temperature was 160°C and the pressure was 6 GO mmHg.
The reaction was carried out for 17 hours. The chromatogram of 1 barley before the reaction is shown in Figure 1. The CD conversion rate at this time was 48.5
%Met.
実施例５
前記した実施例４の反応物の２５′Ｃにおける溶解度を
測定した。その結果をα−ＣＤと比較して表−５に示す
。Example 5 The solubility of the reactant of Example 4 above at 25'C was measured. The results are shown in Table 5 in comparison with α-CD.
型にコニ」Σ
α−ＣＤ １４．１反応後
３２．２
〔発明の効果〕
本発明によればＣＤを簡匣な処理により高溶解性とする
ことができ、本処理により分岐ＣＤと思われる物質が大
量に効率的に生成される。After reaction Σ α-CD 14.1
32.2 [Effects of the Invention] According to the present invention, CD can be made highly soluble through a simple treatment, and a substance considered to be a branched CD can be efficiently produced in large quantities through this treatment.
さらに、カーボン、イオン交換樹脂等を用いる方法、セ
ファデックスなどの分子量差を利用した方法、ＯＤＳカ
ラム、膜による分離方法を組合せて、反応混合物から分
岐ＣＤ部分を得ることができる９分岐ＣＤが高分子の場
合は、目的に応じてその水溶液を酸処理して低分子化す
ることもできろ。Furthermore, by combining methods using carbon, ion exchange resins, etc., methods using molecular weight differences such as Sephadex, separation methods using ODS columns, and membranes, 9-branched CDs can be obtained from the reaction mixture. In the case of molecules, depending on the purpose, the aqueous solution can be treated with an acid to reduce the molecules.
このように、本発明によって得られる反応生成物から分
岐ＣＤ部分を分離し、必要に応じて低分子化して用いる
ほか、用途により酸縮合反応を行なった反応生成物をそ
のまま製品化することもできる。これらの混合物は医薬
品、化粧品、香料。In this way, in addition to separating the branched CD moiety from the reaction product obtained by the present invention and using it after reducing the molecular weight if necessary, the reaction product subjected to the acid condensation reaction can also be commercialized as it is depending on the purpose. . These mixtures are used in pharmaceuticals, cosmetics, and fragrances.
食品等の可溶化等に広く用いることができる。It can be widely used for solubilizing foods, etc.
また、難消化性であるのでビフイダス菌増殖因子、肥満
防止などの健康食品、特殊食品への用途が期待される。In addition, since it is indigestible, it is expected to be used as a growth factor for Bifidobacteria, health foods for obesity prevention, and special foods.
第１図は本発明による酸処理反応前後のクロマトグラム
である。
時 Ｐ＝１ （シ９・）FIG. 1 shows chromatograms before and after the acid treatment reaction according to the present invention. Time P=1 (Si9・)
Claims (4)
処理を行なうことを特徴とする溶解性の高いサイクロデ
キストリンの製造方法。(1) A method for producing highly soluble cyclodextrin, which comprises mixing cyclodextrin and starch decomposition product and subjecting the mixture to acid treatment.
トトリオース、マルトテトラオース、マルトペンタオー
スおよびマルトヘキサオースの中から選ばれたマルトオ
リゴ糖単独、デキストリン、またはこれらの混合物であ
る特許請求の範囲第１項記載の製造方法。(2) Claim 1, wherein the starch decomposition product is a maltooligosaccharide selected from glucose and maltose, maltotriose, maltotetraose, maltopentaose, and maltohexaose, dextrin, or a mixture thereof. Manufacturing method described in section.
イクロデキストリンのいずれか、またはこれらの混合物
である特許請求の範囲第１項記載の製造方法。(3) The manufacturing method according to claim 1, wherein the cyclodextrin is any one of α-, β-, and γ-cyclodextrin, or a mixture thereof.
機酸、ならびに酢酸、シュウ酸、プロピオン酸、乳酸、
マレイン酸、フマル酸、コハク酸、リンゴ酸、酒石酸、
クエン酸、グルコン酸の中から選ばれた有機酸のいずれ
かである特許請求の範囲第１項記載の製造方法。(4) an inorganic acid selected from hydrochloric acid, sulfuric acid and phosphoric acid, and acetic acid, oxalic acid, propionic acid, lactic acid,
maleic acid, fumaric acid, succinic acid, malic acid, tartaric acid,
The manufacturing method according to claim 1, wherein the organic acid is selected from citric acid and gluconic acid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62295298A JP2571199B2 (en) | 1987-11-25 | 1987-11-25 | Method for producing highly soluble cyclodextrin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62295298A JP2571199B2 (en) | 1987-11-25 | 1987-11-25 | Method for producing highly soluble cyclodextrin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01138202A true JPH01138202A (en) | 1989-05-31 |
| JP2571199B2 JP2571199B2 (en) | 1997-01-16 |
Family
ID=17818795
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62295298A Expired - Lifetime JP2571199B2 (en) | 1987-11-25 | 1987-11-25 | Method for producing highly soluble cyclodextrin |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2571199B2 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994016733A1 (en) * | 1993-01-29 | 1994-08-04 | Chiesi Farmaceutici S.P.A. | Highly soluble multicomponent inclusion complexes containing a base type drug, an acid and a cyclodextrin |
| US5426184A (en) * | 1992-02-12 | 1995-06-20 | The United States Of America As Represented By The Department Of Health And Human Services | Cyclodextrin glycosides and processes for their preparation |
| CN100335527C (en) * | 2005-08-22 | 2007-09-05 | 暨南大学 | Water soluble polylactic-acid material, prepn. method and application thereof |
-
1987
- 1987-11-25 JP JP62295298A patent/JP2571199B2/en not_active Expired - Lifetime
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5426184A (en) * | 1992-02-12 | 1995-06-20 | The United States Of America As Represented By The Department Of Health And Human Services | Cyclodextrin glycosides and processes for their preparation |
| WO1994016733A1 (en) * | 1993-01-29 | 1994-08-04 | Chiesi Farmaceutici S.P.A. | Highly soluble multicomponent inclusion complexes containing a base type drug, an acid and a cyclodextrin |
| CN100335527C (en) * | 2005-08-22 | 2007-09-05 | 暨南大学 | Water soluble polylactic-acid material, prepn. method and application thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2571199B2 (en) | 1997-01-16 |
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