CN115397260A - Powdered oligosaccharide composition - Google Patents
Powdered oligosaccharide composition Download PDFInfo
- Publication number
- CN115397260A CN115397260A CN202180024992.XA CN202180024992A CN115397260A CN 115397260 A CN115397260 A CN 115397260A CN 202180024992 A CN202180024992 A CN 202180024992A CN 115397260 A CN115397260 A CN 115397260A
- Authority
- CN
- China
- Prior art keywords
- oligosaccharide composition
- fatty acid
- bagasse
- derived
- acid salt
- 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
- 229920001542 oligosaccharide Polymers 0.000 title claims abstract description 177
- 150000002482 oligosaccharides Chemical class 0.000 title claims abstract description 172
- 239000000203 mixture Substances 0.000 title claims abstract description 155
- 241000609240 Ambelania acida Species 0.000 claims abstract description 93
- 239000010905 bagasse Substances 0.000 claims abstract description 93
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 73
- 239000000194 fatty acid Substances 0.000 claims abstract description 73
- 229930195729 fatty acid Natural products 0.000 claims abstract description 73
- -1 fatty acid salt Chemical class 0.000 claims abstract description 69
- 239000008187 granular material Substances 0.000 claims abstract description 33
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims description 28
- HEBKCHPVOIAQTA-NGQZWQHPSA-N d-xylitol Chemical compound OC[C@H](O)C(O)[C@H](O)CO HEBKCHPVOIAQTA-NGQZWQHPSA-N 0.000 claims description 19
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical group [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 claims description 18
- 239000008116 calcium stearate Substances 0.000 claims description 18
- 235000013539 calcium stearate Nutrition 0.000 claims description 18
- 235000019359 magnesium stearate Nutrition 0.000 claims description 14
- 229910052782 aluminium Inorganic materials 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 10
- 239000011575 calcium Substances 0.000 claims description 7
- 229910052791 calcium Inorganic materials 0.000 claims description 7
- 150000004665 fatty acids Chemical class 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 239000011777 magnesium Substances 0.000 claims description 5
- 229910052749 magnesium Inorganic materials 0.000 claims description 5
- UKMSUNONTOPOIO-UHFFFAOYSA-M behenate Chemical compound CCCCCCCCCCCCCCCCCCCCCC([O-])=O UKMSUNONTOPOIO-UHFFFAOYSA-M 0.000 claims description 4
- 229940116224 behenate Drugs 0.000 claims description 4
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 claims description 4
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 claims description 4
- 229940070765 laurate Drugs 0.000 claims description 4
- 229940105132 myristate Drugs 0.000 claims description 4
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 4
- TUNFSRHWOTWDNC-UHFFFAOYSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 claims description 4
- 229910052744 lithium Inorganic materials 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- 239000011701 zinc Substances 0.000 claims description 3
- 229910052725 zinc Inorganic materials 0.000 claims description 3
- 238000007596 consolidation process Methods 0.000 abstract description 3
- 238000000034 method Methods 0.000 description 25
- 230000000694 effects Effects 0.000 description 24
- 239000000843 powder Substances 0.000 description 24
- 239000007788 liquid Substances 0.000 description 18
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 17
- 238000001878 scanning electron micrograph Methods 0.000 description 16
- 230000000052 comparative effect Effects 0.000 description 15
- 239000002245 particle Substances 0.000 description 15
- 108090000790 Enzymes Proteins 0.000 description 12
- 102000004190 Enzymes Human genes 0.000 description 12
- 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 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 229940088598 enzyme Drugs 0.000 description 12
- 239000008103 glucose Substances 0.000 description 12
- 238000002156 mixing Methods 0.000 description 12
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 11
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 11
- 229920002678 cellulose Polymers 0.000 description 11
- 235000010980 cellulose Nutrition 0.000 description 11
- 239000001913 cellulose Substances 0.000 description 10
- 238000007711 solidification Methods 0.000 description 10
- 230000008023 solidification Effects 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 229920002488 Hemicellulose Polymers 0.000 description 9
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 8
- 238000000354 decomposition reaction Methods 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000000654 additive Substances 0.000 description 7
- 239000012528 membrane Substances 0.000 description 7
- 239000000546 pharmaceutical excipient Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 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 description 6
- 229960005069 calcium Drugs 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 150000002772 monosaccharides Chemical class 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 229920001221 xylan Polymers 0.000 description 6
- 150000004823 xylans Chemical class 0.000 description 6
- 230000002255 enzymatic effect Effects 0.000 description 5
- 239000004570 mortar (masonry) Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 4
- 101710121765 Endo-1,4-beta-xylanase Proteins 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 241000499912 Trichoderma reesei Species 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000004359 castor oil Substances 0.000 description 4
- 235000019438 castor oil Nutrition 0.000 description 4
- 238000002149 energy-dispersive X-ray emission spectroscopy Methods 0.000 description 4
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 4
- 239000001963 growth medium Substances 0.000 description 4
- 229920005610 lignin Polymers 0.000 description 4
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 238000005903 acid hydrolysis reaction Methods 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 239000003925 fat Substances 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 229920001282 polysaccharide Polymers 0.000 description 3
- 239000005017 polysaccharide Substances 0.000 description 3
- 150000004804 polysaccharides Chemical class 0.000 description 3
- 230000002265 prevention Effects 0.000 description 3
- 238000001694 spray drying Methods 0.000 description 3
- 239000006228 supernatant Substances 0.000 description 3
- LGQKSQQRKHFMLI-SJYYZXOBSA-N (2s,3r,4s,5r)-2-[(3r,4r,5r,6r)-4,5,6-trihydroxyoxan-3-yl]oxyoxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)CO[C@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O)OC1 LGQKSQQRKHFMLI-SJYYZXOBSA-N 0.000 description 2
- JCSJTDYCNQHPRJ-UHFFFAOYSA-N 20-hydroxyecdysone 2,3-acetonide Natural products OC1C(O)C(O)COC1OC1C(O)C(O)C(OC2C(C(O)C(O)OC2)O)OC1 JCSJTDYCNQHPRJ-UHFFFAOYSA-N 0.000 description 2
- LGQKSQQRKHFMLI-UHFFFAOYSA-N 4-O-beta-D-xylopyranosyl-beta-D-xylopyranose Natural products OC1C(O)C(O)COC1OC1C(O)C(O)C(O)OC1 LGQKSQQRKHFMLI-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- 239000002028 Biomass Substances 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 2
- SQNRKWHRVIAKLP-UHFFFAOYSA-N D-xylobiose Natural products O=CC(O)C(O)C(CO)OC1OCC(O)C(O)C1O SQNRKWHRVIAKLP-UHFFFAOYSA-N 0.000 description 2
- 229920001353 Dextrin Polymers 0.000 description 2
- 239000004375 Dextrin Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 229920002774 Maltodextrin Polymers 0.000 description 2
- 239000005913 Maltodextrin Substances 0.000 description 2
- 240000000111 Saccharum officinarum Species 0.000 description 2
- 235000007201 Saccharum officinarum Nutrition 0.000 description 2
- FTTUBRHJNAGMKL-UHFFFAOYSA-N Xylohexaose Natural products OC1C(O)C(O)COC1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(OC4C(C(O)C(OC5C(C(O)C(O)OC5)O)OC4)O)OC3)O)OC2)O)OC1 FTTUBRHJNAGMKL-UHFFFAOYSA-N 0.000 description 2
- LFFQNKFIEIYIKL-UHFFFAOYSA-N Xylopentaose Natural products OC1C(O)C(O)COC1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(OC4C(C(O)C(O)OC4)O)OC3)O)OC2)O)OC1 LFFQNKFIEIYIKL-UHFFFAOYSA-N 0.000 description 2
- JVZHSOSUTPAVII-UHFFFAOYSA-N Xylotetraose Natural products OCC(OC1OCC(OC2OCC(OC3OCC(O)C(O)C3O)C(O)C2O)C(O)C1O)C(O)C(O)C=O JVZHSOSUTPAVII-UHFFFAOYSA-N 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
- 238000010306 acid treatment Methods 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 description 2
- PYMYPHUHKUWMLA-WDCZJNDASA-N arabinose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WDCZJNDASA-N 0.000 description 2
- JCSJTDYCNQHPRJ-FDVJSPBESA-N beta-D-Xylp-(1->4)-beta-D-Xylp-(1->4)-D-Xylp Chemical compound O[C@@H]1[C@@H](O)[C@H](O)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(O)OC2)O)OC1 JCSJTDYCNQHPRJ-FDVJSPBESA-N 0.000 description 2
- 159000000007 calcium salts Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- JZCCFEFSEZPSOG-UHFFFAOYSA-L copper(II) sulfate pentahydrate Chemical compound O.O.O.O.O.[Cu+2].[O-]S([O-])(=O)=O JZCCFEFSEZPSOG-UHFFFAOYSA-L 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- 235000019425 dextrin Nutrition 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 229930182830 galactose Natural products 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000005469 granulation Methods 0.000 description 2
- 230000003179 granulation Effects 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 238000010335 hydrothermal treatment Methods 0.000 description 2
- NQXWGWZJXJUMQB-UHFFFAOYSA-K iron trichloride hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].Cl[Fe+]Cl NQXWGWZJXJUMQB-UHFFFAOYSA-K 0.000 description 2
- 159000000003 magnesium salts Chemical class 0.000 description 2
- 229940035034 maltodextrin Drugs 0.000 description 2
- CNFDGXZLMLFIJV-UHFFFAOYSA-L manganese(II) chloride tetrahydrate Chemical compound O.O.O.O.[Cl-].[Cl-].[Mn+2] CNFDGXZLMLFIJV-UHFFFAOYSA-L 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
- 229920000053 polysorbate 80 Polymers 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 125000000969 xylosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)CO1)* 0.000 description 2
- KPTPSLHFVHXOBZ-BIKCPUHGSA-N xylotetraose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)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(O)OC3)O)OC2)O)OC1 KPTPSLHFVHXOBZ-BIKCPUHGSA-N 0.000 description 2
- ABKNGTPZXRUSOI-UHFFFAOYSA-N xylotriose Natural products OCC(OC1OCC(OC2OCC(O)C(O)C2O)C(O)C1O)C(O)C(O)C=O ABKNGTPZXRUSOI-UHFFFAOYSA-N 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- LUEWUZLMQUOBSB-FSKGGBMCSA-N (2s,3s,4s,5s,6r)-2-[(2r,3s,4r,5r,6s)-6-[(2r,3s,4r,5s,6s)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(2r,4r,5s,6r)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol 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](OC3[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-FSKGGBMCSA-N 0.000 description 1
- KSEBMYQBYZTDHS-HWKANZROSA-M (E)-Ferulic acid Natural products COC1=CC(\C=C\C([O-])=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-M 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- QPILHXCDZYWYLQ-UHFFFAOYSA-N 2-nonyl-1,3-dioxolane Chemical compound CCCCCCCCCC1OCCO1 QPILHXCDZYWYLQ-UHFFFAOYSA-N 0.000 description 1
- 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
- SATHPVQTSSUFFW-UHFFFAOYSA-N 4-[6-[(3,5-dihydroxy-4-methoxyoxan-2-yl)oxymethyl]-3,5-dihydroxy-4-methoxyoxan-2-yl]oxy-2-(hydroxymethyl)-6-methyloxane-3,5-diol Chemical compound OC1C(OC)C(O)COC1OCC1C(O)C(OC)C(O)C(OC2C(C(CO)OC(C)C2O)O)O1 SATHPVQTSSUFFW-UHFFFAOYSA-N 0.000 description 1
- 229920000189 Arabinogalactan Polymers 0.000 description 1
- 239000001904 Arabinogalactan Substances 0.000 description 1
- 241000228212 Aspergillus Species 0.000 description 1
- 241000228257 Aspergillus sp. Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 102100032487 Beta-mannosidase Human genes 0.000 description 1
- 235000018185 Betula X alpestris Nutrition 0.000 description 1
- 235000018212 Betula X uliginosa Nutrition 0.000 description 1
- 108010059892 Cellulase Proteins 0.000 description 1
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical class OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
- 206010017943 Gastrointestinal conditions Diseases 0.000 description 1
- 229920001503 Glucan Polymers 0.000 description 1
- 229920002581 Glucomannan Polymers 0.000 description 1
- 101000851593 Homo sapiens Separin Proteins 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
- 229920000057 Mannan Polymers 0.000 description 1
- FWDCZWAICKKXNW-UHFFFAOYSA-N N.N.N.N.N.N.O.O.O.O Chemical compound N.N.N.N.N.N.O.O.O.O FWDCZWAICKKXNW-UHFFFAOYSA-N 0.000 description 1
- 102100036750 Separin Human genes 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 241000187747 Streptomyces Species 0.000 description 1
- 241000187180 Streptomyces sp. Species 0.000 description 1
- 241000223259 Trichoderma Species 0.000 description 1
- 241000196252 Ulva Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003674 animal food additive Substances 0.000 description 1
- 235000019312 arabinogalactan Nutrition 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- NGPGDYLVALNKEG-UHFFFAOYSA-N azanium;azane;2,3,4-trihydroxy-4-oxobutanoate Chemical compound [NH4+].[NH4+].[O-]C(=O)C(O)C(O)C([O-])=O NGPGDYLVALNKEG-UHFFFAOYSA-N 0.000 description 1
- 108010047754 beta-Glucosidase Proteins 0.000 description 1
- 102000006995 beta-Glucosidase Human genes 0.000 description 1
- 108010055059 beta-Mannosidase Proteins 0.000 description 1
- 238000005422 blasting Methods 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- LLSDKQJKOVVTOJ-UHFFFAOYSA-L calcium chloride dihydrate Chemical compound O.O.[Cl-].[Cl-].[Ca+2] LLSDKQJKOVVTOJ-UHFFFAOYSA-L 0.000 description 1
- 229940052299 calcium chloride dihydrate Drugs 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 229940106157 cellulase Drugs 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 208000002925 dental caries Diseases 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 230000007515 enzymatic degradation Effects 0.000 description 1
- KSEBMYQBYZTDHS-HWKANZROSA-N ferulic acid Chemical compound COC1=CC(\C=C\C(O)=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-N 0.000 description 1
- 235000001785 ferulic acid Nutrition 0.000 description 1
- 229940114124 ferulic acid Drugs 0.000 description 1
- KSEBMYQBYZTDHS-UHFFFAOYSA-N ferulic acid Natural products COC1=CC(C=CC(O)=O)=CC=C1O KSEBMYQBYZTDHS-UHFFFAOYSA-N 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 235000021255 galacto-oligosaccharides Nutrition 0.000 description 1
- 150000003271 galactooligosaccharides Chemical class 0.000 description 1
- 229940046240 glucomannan Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229940059442 hemicellulase Drugs 0.000 description 1
- 108010002430 hemicellulase Proteins 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 238000001027 hydrothermal synthesis Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229960000511 lactulose Drugs 0.000 description 1
- PFCRQPBOOFTZGQ-UHFFFAOYSA-N lactulose keto form Natural products OCC(=O)C(O)C(C(O)CO)OC1OC(CO)C(O)C(O)C1O PFCRQPBOOFTZGQ-UHFFFAOYSA-N 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- WRUGWIBCXHJTDG-UHFFFAOYSA-L magnesium sulfate heptahydrate Chemical compound O.O.O.O.O.O.O.[Mg+2].[O-]S([O-])(=O)=O WRUGWIBCXHJTDG-UHFFFAOYSA-L 0.000 description 1
- 229940061634 magnesium sulfate heptahydrate Drugs 0.000 description 1
- 238000013507 mapping Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000005374 membrane filtration Methods 0.000 description 1
- 238000001471 micro-filtration Methods 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- UTOPWMOLSKOLTQ-UHFFFAOYSA-M octacosanoate Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCC([O-])=O UTOPWMOLSKOLTQ-UHFFFAOYSA-M 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- SECPZKHBENQXJG-FPLPWBNLSA-N palmitoleic acid Chemical compound CCCCCC\C=C/CCCCCCCC(O)=O SECPZKHBENQXJG-FPLPWBNLSA-N 0.000 description 1
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- WBHHMMIMDMUBKC-QJWNTBNXSA-M ricinoleate Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC([O-])=O WBHHMMIMDMUBKC-QJWNTBNXSA-M 0.000 description 1
- 229940066675 ricinoleate Drugs 0.000 description 1
- 229940116351 sebacate Drugs 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
- 239000007974 sodium acetate buffer Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000005846 sugar alcohols Chemical class 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 150000004685 tetrahydrates Chemical class 0.000 description 1
- QURCVMIEKCOAJU-UHFFFAOYSA-N trans-isoferulic acid Natural products COC1=CC=C(C=CC(O)=O)C=C1O QURCVMIEKCOAJU-UHFFFAOYSA-N 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Images
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
- A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
- A23L29/30—Foods or foodstuffs containing additives; Preparation or treatment thereof containing carbohydrate syrups; containing sugars; containing sugar alcohols, e.g. xylitol; containing starch hydrolysates, e.g. dextrin
-
- 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
- A23L5/00—Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/14—Preparation of compounds containing saccharide radicals produced by the action of a carbohydrase (EC 3.2.x), e.g. by alpha-amylase, e.g. by cellulase, hemicellulase
-
- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P60/00—Technologies relating to agriculture, livestock or agroalimentary industries
- Y02P60/80—Food processing, e.g. use of renewable energies or variable speed drives in handling, conveying or stacking
- Y02P60/87—Re-use of by-products of food processing for fodder production
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Zoology (AREA)
- Nutrition Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Wood Science & Technology (AREA)
- General Chemical & Material Sciences (AREA)
- Microbiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biotechnology (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Saccharide Compounds (AREA)
Abstract
The present invention aims to provide a powdery oligosaccharide composition which comprises granules of an oligosaccharide composition derived from bagasse and has improved easy consolidation, and to provide a powdery oligosaccharide composition which comprises granules of an oligosaccharide composition derived from bagasse and a fatty acid salt attached to the surface of the granules.
Description
Technical Field
The present invention relates to a powdered oligosaccharide composition comprising granules of an oligosaccharide composition derived from bagasse, and a fatty acid salt attached to the surface of the granules.
Background
Oligosaccharides are saccharides in which several monosaccharides are bound to each other by glycosidic bonds, and various oligosaccharides such as galactooligosaccharides, fructooligosaccharides, xylooligosaccharides, isomaltooligosaccharides, and lactulose oligosaccharides are known from their constituent monosaccharides. These oligosaccharides are commercially available in a large amount as supplements which have a selective growth promoting effect on intestinal bacteria and a function of maintaining the gastrointestinal condition well, in addition to characteristics such as low sweetness, low calorie, and caries resistance. In addition, the compound is used not only in human food applications but also as a feed additive for livestock.
Oligosaccharides are generally produced by acid decomposition and/or enzymatic decomposition of cellulose or hemicellulose contained in biomass, and as methods for producing an oligosaccharide solution, a method for producing an oligosaccharide solution from a hemicellulase treatment solution in a pulp production step (patent document 1), a method for producing an oligosaccharide solution by enzymatic saccharification of cellulose-containing biomass (patent document 2), and the like are known.
Oligosaccharides are desired to be powdered for the reasons of preventing the growth of microorganisms in sugar solutions, facilitating the incorporation into solid feeds, and the like. However, the powdered oligosaccharide has problems that it is easy to be deliquesced and solidified during storage, and is mechanically attached to make it difficult to take it out.
As a method for improving the hygroscopicity of oligosaccharides, a method of coating oligosaccharides with fats and oils is disclosed (patent document 3).
Documents of the prior art
Patent document
Patent document 1: japanese patent No. 3951545
Patent document 2: WO2017/170919A1
Patent document 3: japanese patent laid-open No. 2004-175713
Disclosure of Invention
Problems to be solved by the invention
As described above, although a method of coating oligosaccharides with fats and oils is disclosed as a method of improving the hygroscopicity of oligosaccharides, the solidification prevention effect is insufficient even when the oligosaccharide composition derived from bagasse is coated with fats and oils. Accordingly, the present invention aims to provide a powdery oligosaccharide composition which comprises granules of an oligosaccharide composition derived from bagasse and has improved easy consolidation.
Means for solving the problems
The present inventors have conducted intensive studies and, as a result, have found that a powdery oligosaccharide composition comprising granules of an oligosaccharide composition derived from bagasse and a fatty acid salt attached to the surface of the granules has a high effect of preventing consolidation, and have completed the present invention.
That is, the present invention provides the inventions having the following configurations [ 1 ] to [ 11 ].
[ 1 ] A powdery oligosaccharide composition comprising granules of an oligosaccharide composition derived from bagasse and a fatty acid salt attached to the surface of the granules.
[ 2 ] the powdery oligosaccharide composition according to [ 1 ], wherein the surface of the granule is coated with the fatty acid salt.
[ 3 ] the powdery oligosaccharide composition according to [ 1 ] or [ 2 ], wherein the fatty acid salt is 1 or 2 or more selected from salts of fatty acids having 12 to 22 carbon atoms.
[ 4 ] the powdery oligosaccharide composition according to any one of [ 1 ] to [ 3 ], wherein the fatty acid salt is 1 or 2 or more selected from metal salts having a valence of 1 to 3.
[ 5 ] the powder oligosaccharide composition according to any one of [ 1 ] to [ 4 ], wherein the fatty acid salt is 1 or 2 or more selected from a stearate, a palmitate, a laurate, a myristate and a behenate.
The powdered oligosaccharide composition according to any one of [ 1 ] to [ 5 ], wherein the fatty acid salt is 1 or more or 2 or more selected from sodium fatty acid, lithium fatty acid, magnesium fatty acid, calcium fatty acid, zinc fatty acid and aluminum fatty acid.
[ 7 ] the powdered oligosaccharide composition according to any one of [ 1 ] to [ 6 ], wherein the fatty acid salt is calcium stearate and/or magnesium stearate.
[ 8 ] the powdery oligosaccharide composition according to any one of [ 1 ] to [ 7 ], wherein the oligosaccharide composition derived from bagasse comprises xylooligosaccharide as a main component.
The powder oligosaccharide composition according to any one of [ 1 ] to [ 8 ], wherein the fatty acid salt is contained in an amount of 0.1 to 25 parts by weight based on 100 parts by weight of the oligosaccharide composition derived from bagasse.
[ 10 ] the powdery oligosaccharide composition according to any one of [ 1 ] to [ 9 ], wherein the oligosaccharide composition derived from bagasse comprises 1 to 50% by weight of xylooligosaccharide.
[ 11 ] A composition comprising 0.1 to 25 parts by weight of a fatty acid salt per 100 parts by weight of a bagasse-derived oligosaccharide composition.
ADVANTAGEOUS EFFECTS OF INVENTION
The powdery oligosaccharide composition of the invention is a powder containing an oligosaccharide derived from bagasse, but has improved easy-to-solidify properties, and therefore, deliquescence can be prevented and the powder state can be maintained, whereby quality deterioration due to solidification during storage, loss due to adhesion to machinery, and the like can be prevented.
Drawings
Fig. 1 shows a scanning electron microscope (hereinafter referred to as "SEM") image of the powdered oligosaccharide composition of comparative example 1.
Fig. 2 shows an SEM image of the powdered oligosaccharide composition of example 1.
Fig. 3 shows a SEM image of the powdered oligosaccharide composition of example 2.
Fig. 4 shows an SEM image of the powdered oligosaccharide composition of example 1.
Fig. 5 shows a mapping of calcium in the SEM image of fig. 4 using energy dispersive X-ray spectroscopy.
Fig. 6 shows an SEM image of the powdered oligosaccharide composition of example 2.
Fig. 7 shows a view of magnesium in the SEM image of fig. 6 using energy dispersive X-ray spectroscopy.
Fig. 8 shows an SEM image of the powdered oligosaccharide composition of comparative example 12.
Detailed Description
Hereinafter, the present embodiment will be described.
The powdered oligosaccharide composition of the invention comprises granules of an oligosaccharide composition derived from bagasse, and a fatty acid salt attached to the surface of the granules. The powdery oligosaccharide composition of the invention is mainly composed of particles of the bagasse-derived oligosaccharide composition having a fatty acid salt attached to the surface thereof, but may contain particles other than the particles of the bagasse-derived oligosaccharide composition or the particles of the bagasse-derived oligosaccharide composition having no fatty acid salt attached to the surface thereof, as long as the use of the powdery oligosaccharide composition is not hindered.
< granules of oligosaccharide composition derived from bagasse >
Hereinafter, pellets of an oligosaccharide composition derived from bagasse will be described.
An "oligosaccharide" is a sugar in which several monosaccharides are bound to each other via a glycosidic bond. The number of monosaccharides constituting the oligosaccharide is usually 2 or more and 10 or less, and preferably 2 or more and 6 or less.
The "oligosaccharide derived from bagasse" refers to an oligosaccharide prepared from bagasse, which is pressed pulp of sugarcane. Bagasse, which is a pressed pulp of sugarcane, is mainly composed of cellulose and hemicellulose, which are polysaccharides, and lignin, which is an aromatic polymer. Oligosaccharides are produced by decomposing cellulose or hemicellulose, which is a polysaccharide. That is, glucan constituting cellulose or xylan, mannan, galactan, arabinogalactan, glucomannan, and the like constituting hemicellulose are decomposed to produce oligosaccharides composed of glucose, xylose, arabinose, mannose, galactose, and the like. In addition, since bagasse mainly contains xylan as hemicellulose, xylooligosaccharide is suitably produced from bagasse.
As a method for obtaining oligosaccharides by decomposing cellulose or hemicellulose, for example, methods such as acid hydrolysis and enzymatic decomposition are known, but the method is not limited to these, and acid hydrolysis and enzymatic decomposition may be performed in combination.
Examples of the method for producing oligosaccharides by acid hydrolysis include, but are not limited to, dilute sulfuric acid treatment, hydrothermal treatment using acetic acid produced by hydrothermal reaction, and the like.
Examples of the enzymatic degradation include, but are not limited to, a method using an enzyme such as xylanase, mannanase, or glucanase. It is known that xylan is contained in large amounts as hemicellulose in bagasse, and therefore an enzyme containing xylanase is preferably used.
Xylanase is not particularly limited as long as it has an activity of hydrolyzing xylan to produce xylooligosaccharides, and commercially available Enzymes such as "124731251124811251251254020" (registered trademark) X (manufactured by newyobo chemical company corporation), "124731246312521125404" (registered trademark) X (manufactured by mitsubishi chemical corporation), "12412475125252525 (registered trademark) TP (manufactured by mitsubishi 1245612481124505050505046, manufactured by enteromorpha corporation), trichoderma reesei (Trichoderma reesei), aspergillus (Aspergillus sp.12451124), rhizogenes (Streptomyces sp), trichoderma sp (Streptomyces sp.sp.. Furthermore, cellulase compositions having xylanase activity obtained according to WO2017/170919 may be used.
In the case of enzymatic decomposition, a method is known in which lignin is decomposed or bonds between celluloses are released by a treatment generally called pretreatment, and thus an enzyme is easily reacted with a cellulose or a hemicellulose. Examples of the pretreatment method include, but are not limited to, alkali treatment with sodium hydroxide, ammonia, or the like, blasting, hydrothermal treatment, dilute sulfuric acid treatment, and the like.
The term "xylooligosaccharide" refers to an oligosaccharide mainly produced by decomposing xylan, and is a sugar in which 2 or more xylose units are bound to each other by glycosidic bonds, regardless of the presence or absence of a side chain. Examples of xylo-oligosaccharide include xylobiose, xylotriose, xylotetraose, xylopentaose, and xylohexaose, and a mixture containing 2 or more of them may be used.
The phrase "the oligosaccharide composition derived from bagasse contains xylooligosaccharide as a main component" means that the solid component of the oligosaccharide composition derived from bagasse contains xylooligosaccharide in the highest proportion as compared with the other components except the excipient. The amount of xylooligosaccharide can be quantified by using high performance liquid chromatography or the like.
The "pellets of an oligosaccharide composition derived from bagasse" are obtained by granulating a liquid containing oligosaccharide derived from bagasse, which liquid is produced by decomposing cellulose and/or hemicellulose contained in bagasse. The liquid containing oligosaccharides derived from bagasse may contain polysaccharides, lignin decomposition products, organic acids, monosaccharides, and the like, which are not decomposed into oligosaccharides, in addition to oligosaccharides. Examples of the lignin degradation product include coumaric acid and ferulic acid, examples of the organic acid include acetic acid and formic acid, and examples of the monosaccharide include glucose, xylose, arabinose, mannose and galactose. The liquid containing oligosaccharides derived from bagasse may be a liquid obtained by purifying a solution containing oligosaccharides produced by decomposing bagasse by the above-mentioned acid decomposition or enzyme decomposition by solid-liquid separation, membrane treatment, activated carbon, ion exchange resin, or the like, or by concentrating by membrane concentration, evaporative concentration, or the like.
A method for producing a liquid containing oligosaccharides derived from bagasse is described in, for example, WO2017/170919.
The method for granulating the liquid containing oligosaccharide derived from bagasse is not particularly limited, and methods such as a spray drying method, a freeze drying method, and a fluidized bed method are known. In the granulation of the liquid containing the oligosaccharide derived from bagasse, an excipient or the like may be added, and the granules of the oligosaccharide composition derived from bagasse may contain an excipient. As excipients for granulation, starch, dextrin, lactose, crystalline cellulose, sugar alcohol, and the like are generally known, and dextrin is preferably used.
The granules of the bagasse-derived oligosaccharide composition may contain the excipient and the like as described above, but the bagasse-derived oligosaccharide composition preferably contains 0.1 to 60 wt% of the bagasse-derived oligosaccharides, and more preferably contains 1 to 50 wt% of xylooligosaccharides. The amount of the oligosaccharide derived from bagasse in the oligosaccharide composition derived from bagasse is more preferably 1 to 60% by weight, and still more preferably 5 to 55% by weight. The amount of xylooligosaccharide contained in the bagasse-derived oligosaccharide composition is more preferably 5 to 50% by weight, and still more preferably 5 to 40% by weight.
When the granules of the bagasse-derived oligosaccharide composition contain an excipient, the amount of the excipient contained in the bagasse-derived oligosaccharide composition is preferably 5 to 99.9% by weight, more preferably 5 to 92% by weight, and even more preferably 10 to 85% by weight.
< salts of fatty acids >
Hereinafter, the fatty acid salt attached to the surface of the granule of the oligosaccharide composition derived from bagasse will be described.
The "fatty acid salt" is a salt of a fatty acid which is a monocarboxylic acid having a hydrocarbon group having 2 or more carbon atoms.
The fatty acid salt is not particularly limited, but is preferably 1 or 2 or more selected from salts of fatty acids having 8 to 22 carbon atoms, and more preferably 1 or 2 or more selected from salts of fatty acids having 12 to 22 carbon atoms.
The fatty acid salt is preferably 1 or 2 or more selected from octanoate (octanoate), decanoate (decanoate), laurate, myristate, palmitate, stearate, behenate, arachinate, palmitoleate, oleate, montanate, octanoate, sebacate and ricinoleate, and more preferably 1 or 2 or more selected from stearate, palmitate, laurate, octanoate, myristate and behenate.
The fatty acid salt is preferably 1 or 2 or more selected from among 1 to 3-valent metal salts, more preferably 1 or 2 or more selected from among magnesium salts (magnesium fatty acid), sodium salts (sodium fatty acid), calcium salts (calcium fatty acid), zinc salts (zinc fatty acid), lithium salts (lithium fatty acid), and aluminum salts (aluminum fatty acid), and still more preferably magnesium salts or calcium salts.
When the powdered oligosaccharide composition of the present invention is used in feed or food, the fatty acid salt is more preferably calcium stearate and/or magnesium stearate from the viewpoint of safety and effect.
The "fatty acid salt adheres to the surface of the particles of the oligosaccharide composition derived from bagasse" refers to the particles of the oligosaccharide composition derived from bagasse, to which the fatty acid salt adheres, and can be confirmed, for example, by observing the surface of the particles of the oligosaccharide composition derived from bagasse before and after mixing with the fatty acid salt with a Scanning Electron Microscope (SEM). Further, it was confirmed that the deposit was a fatty acid salt by SEM-energy dispersive X-ray spectrometry, which was performed to examine the salt components such as calcium and magnesium.
The fatty acid salt preferably coats the surface of the particles of the oligosaccharide composition derived from bagasse. The fatty acid salt may cover a part of the surface of the granule of the oligosaccharide composition derived from bagasse, or may cover the entire surface of the granule of the oligosaccharide composition derived from bagasse. The fatty acids may form an outer layer coating the surface of the particles of the oligosaccharide composition derived from bagasse.
The method of adhering the fatty acid salt to the surface of the granules of the oligosaccharide composition derived from bagasse is not particularly limited, but an example thereof is a method of mixing the granules of the oligosaccharide composition derived from bagasse with the fatty acid salt at normal temperature and pressure. As described above, the "fatty acid salt adheres to the surface of the granule of the oligosaccharide composition derived from bagasse" means that the granule of the fatty acid salt adheres to the surface of the granule of the oligosaccharide composition derived from bagasse, and therefore, it is preferable to mix the granule of the oligosaccharide composition derived from bagasse and the fatty acid salt at a temperature not higher than the melting point of both. The mixing is generally performed by rotating a mixing container itself called a container rotating type mixer, a mixing container called a container fixed type mixer is fixed and mixed by a stirrer such as a paddle or a screw, or by blowing an air flow, and a container rotating type mixer and a container fixed type mixer are combined and mixed in a composite type, but the present invention is not limited thereto. The mixing may be either batch or continuous.
In order to attach the fatty acid salt to the surface of the granules of the oligosaccharide composition derived from bagasse as described above, the powder of the fatty acid salt used preferably contains granules having a smaller particle size than the granules of the oligosaccharide composition derived from bagasse.
The larger the amount of the fatty acid salt to be mixed, the higher the effect of preventing solidification, but from the viewpoint of cost, the amount of the fatty acid salt to be mixed is usually 0.01 to 200 parts by weight, preferably 0.1 to 100 parts by weight, more preferably 0.1 to 50 parts by weight, and still more preferably 0.1 to 25 parts by weight, based on 100 parts by weight of the oligosaccharide composition derived from bagasse.
A composition comprising 0.1 to 25 parts by weight of a fatty acid salt per 100 parts by weight of the oligosaccharide composition derived from bagasse is also included in the present invention.
Examples
The present invention will be specifically described below based on reference examples, examples and comparative examples.
Reference example 1 pretreatment of raw bagasse
Bagasse, 500g in dry weight, was pretreated at 80 ℃ for 3 hours by adding a sodium hydroxide solution and water so that the sodium hydroxide content became 50g and the solid content concentration became 5 wt%. The solid component after solid-liquid separation using a strainer was washed with pure water to obtain a saccharified material.
[ reference example 2 ] preparation of enzyme composition for xylooligosaccharide production
[ preculture ]
Using distilled water, a preparation containing 5% (w/vol) corn steep liquor, 2% (w/vol) glucose, 0.37% (w/vol) ammonium tartrate100mL of an aqueous solution of 0.004% (w/vol), 0.14% (w/vol), 0.2% (w/vol), 0.03% (w/vol), 0.02% (w/vol), 0.01% (w/vol), 0.004% (w/vol), 0.0008% (w/vol), 0.0006% (w/vol), 0.0026% (w/vol) and 0.0026% (w/vol) of iron (III) chloride hexahydrate, copper (II) sulfate pentahydrate, 0.0008% (w/vol), 0.0006% (w/vol) of manganese chloride tetrahydrate, 0.0026% (w/vol) of heptamolybdic acid hexaammonium tetrahydrate was prepared in a 500mL baffled Erlenmeyer flask, and autoclave-sterilized at 121 ℃ for 15 minutes. After cooling, PE-M and Tween80, which were separately sterilized by autoclaving at 121 ℃ for 15 minutes, were added to each of the culture media at 0.01% (w/vol) to prepare a preculture medium. Trichoderma reesei ATCC66589 (sold by ATCC) was set to 1X 10 in 100mL of the preculture medium 5 Each cell was inoculated in a volume of one mL, and the mixture was subjected to shaking culture at 28 ℃ for 72 hours at 180rpm to prepare a preculture (shaking apparatus: BIO-SHAKER BR-40LF, manufactured by TAITEC K.K.).
[ formal culture ]
Using distilled water, an aqueous solution containing corn steep liquor 5% (w/vol), glucose 2% (w/vol), cellulose (1245099124751252310% (w/vol), ammonium tartrate 0.37% (w/vol), ammonium sulfate 0.14% (w/vol), potassium dihydrogen phosphate 0.2% (w/vol), calcium chloride dihydrate 0.03% (w/vol), magnesium sulfate heptahydrate 0.03% (w/vol), zinc chloride 0.02% (w/vol), iron (III) chloride hexahydrate 0.01% (w/vol), copper (II) sulfate pentahydrate 0.004% (w/vol), manganese chloride tetrahydrate 0.0008% (w/vol), boric acid 0.0006% (w/vol), and ammonium hexamolybdate tetrahydrate 0.0026% (w/vol) was prepared, and 2.5L of the prepared aqueous solution was put into a 5L-volume wide-mouthed bottle 2A (DPC-2A container manufactured by ablet, a, and sterilized at 121 ℃ for 15 minutes. After cooling, 0.1% (w/vol) of PE-M and Tween80, which were sterilized separately at 121 ℃ for 15 minutes by autoclaving, were added to each of the culture media to prepare a culture medium. 250mL of Trichoderma reesei ATCC66589 previously precultured in the preculture medium was inoculated into 2.5L of the main culture medium. Then, after centrifugation, the supernatant was subjected to membrane filtration using \\/124861252 \/12459 (12513\/1252312463manufactured by 125125125125112522501255. The culture broth was supplemented with β -glucosidase (Novozymes 188) in an amount of 1/100 by weight of the protein to obtain an enzyme composition.
[ preparation of enzyme composition for producing xylooligosaccharide ]
The pH of the enzyme composition was adjusted to pH7.5 by an aqueous solution of sodium hydroxide, diluted with water until the protein concentration reached 4g/L, and then incubated at 40 ℃ for 2 hours.
[ reference example 3 ] measurement of xylanolytic Activity
Xylan (Xylom from Birch wood, manufactured by Fluca) was suspended in 50mM sodium acetate buffer (pH 5.0) to be 1 wt% as a substrate solution. To the dispensed 500. Mu.L of substrate solution, 5. Mu.L of enzyme solution was added, and the mixture was reacted at 50 ℃ while rotating and mixing. The reaction time was set to 30 minutes. After the reaction, the tube was centrifuged, and the reducing sugar concentration of the supernatant component was measured by the DNS method. In this reaction system, the amount of enzyme that produced 1. Mu. Mol of reducing sugar in 1 minute was defined as 1U, and the activity value (U/mL) was calculated according to the following formula.
Xylanolytic activity (U/mL) = reducing sugar concentration (g/L) × 1000 × 505 (μ L)/(150.13 × reaction time (min) × 5 (μ L)).
[ reference example 4 ] xylooligosaccharide analysis
Xylo-oligosaccharides, glucose and xylose were quantitatively analyzed using Hitachi high performance liquid chromatography LaChrom Eite (HITACHI) under the following conditions.
Xylo-oligosaccharides, glucose and xylose were quantitatively analyzed based on a standard curve prepared with standards for xylo-oligosaccharides (xylobiose, xylotriose, xylotetraose, xylopentaose and xylohexaose), glucose and xylose. The term "xylooligosaccharide" as used in the present example means an oligosaccharide in which xylose is bonded to 2 to 6 members of the β -glycosidic bond.
Column: KS802, KS803 (SHODEX)
Mobile phase: water (I)
The detection method comprises the following steps: RI (Ri)
Flow rate: 0.5 mL/min
Temperature: 75 deg.C
[ reference example 5 ] preparation of oligosaccharide composition derived from bagasse
400g (dry weight) of the pretreated bagasse prepared in reference example 1 was added to the enzyme composition for producing xylo-oligosaccharide prepared in reference example 2 so that the xylanolytic activity became 250U per 1g of solid content, and pure water was added to adjust the solid content concentration to 5%. After adjusting to pH7.0 using hydrochloric acid, the mixture was heated at 40 ℃ for 8 hours with stirring. Performing solid-liquid separation with a skimmer, and centrifuging the liquid component at 8000G for 20 minutes to recover a supernatant, which is subjected to microfiltration with 12470124882 (124701245412488125125125229712512512512512597). Next, CF-II (effective membrane area 140 cm) was prepared using a membrane separation apparatus "SEPA" (registered trademark) 2 ，GE W&PT), and an ultrafiltration membrane SPE50 (molecular weight cut-off 50,000, manufactured by Synderfiltration Co., ltd.) were filtered at an operation temperature of 35 ℃ and a membrane surface linear velocity of 20 cm/sec under a condition that the flux was constant at 0.1 m/day under a controlled operation pressure. Next, the liquid fraction was filtered using NFW (molecular weight cut-off 300-500, manufactured by Synder). The operation temperature was set at 35 ℃ and the linear velocity of the membrane surface was set at 20 cm/sec, and filtration treatment was performed under a filtration pressure of 2MPa until the liquid volume on the non-permeation side became 0.5L. The liquid on the non-permeation side was collected and evaporated and concentrated by an evaporator to prepare a liquid containing oligosaccharides derived from bagasse. The xylo-oligosaccharide, glucose and xylose contained in the liquid containing oligosaccharides derived from bagasse were measured by the method of reference example 4. The composition is shown in table 1.
TABLE 1
| Composition (I) | Concentration (g/L) |
| Oligo xylose | 282 |
| Glucose | 143 |
| Xylose | 0 |
The bagasse-derived oligosaccharide composition was prepared by mixing 800g of a liquid containing bagasse-derived oligosaccharides, 500g of water, and 300g of maltodextrin, and subjecting the resulting mixture to a spray-drying method. The composition of the prepared oligosaccharide composition derived from bagasse is shown in table 2.
TABLE 2
[ comparative examples 1 to 7 and examples 1 to 2 ] preparation of powdery oligosaccharide composition comprising bagasse-derived oligosaccharide composition and various additives, fluidity test, and observation of granule surface
100 parts by weight (dry weight) of the bagasse-derived oligosaccharide composition prepared by the method of reference example 5 and 5 parts by weight of each additive were weighed and mixed in a mortar to prepare a powdery oligosaccharide composition. About 5g of the obtained powdered oligosaccharide composition was spread out in an aluminum pan and left to stand at room temperature, and fluidity after 3 days was confirmed. Further, regarding the hardened castor oil of comparative example 6, the hardened castor oil and the oligosaccharide composition derived from bagasse were mixed in a mortar, and the mixture was put into an oven at 95 ℃ for 30 minutes, and then, the mixture was pulverized again in the mortar, and the fluidity of the obtained composition was similarly confirmed (hardened castor oil (with heating)). The results of the additives and the fluidity are shown in table 3. Regarding the fluidity, a case where the aluminum plate was gently shaken from the side and the whole powder flowed was represented as "+", a state where the powder flowed but liquefied by spoon mixing was represented as "+", and a state where the whole was solidified, gelled or liquefied was represented as "-".
TABLE 3
As shown in table 3, it was found that the effect of maintaining fluidity (i.e., the effect of preventing solidification) was high when calcium stearate or magnesium stearate was mixed in the oligosaccharide composition derived from bagasse. Further, when hardened castor oil was mixed with the oligosaccharide composition derived from bagasse, fluidity remained, but the mixture was liquefied after spoon-mixing.
A powdery oligosaccharide composition containing calcium stearate or magnesium stearate having a high effect was subjected to observation of the particle surface using a scanning electron microscope apparatus S-4800 (manufactured by hitachi 124951245212486, 1249412412512474. The SEM image of the powdered oligosaccharide composition of comparative example 1 is shown in fig. 1, the SEM image of the powdered oligosaccharide composition of example 1 is shown in fig. 2, and the SEM image of the powdered oligosaccharide composition of example 2 is shown in fig. 3. Furthermore, the powdered oligosaccharide compositions of examples 1 and 2 were analyzed by SEM-energy dispersive X-ray spectroscopy. The SEM image of example 1 is shown in fig. 4, the map of calcium in the SEM image of fig. 4 is shown in fig. 5, the SEM image of example 2 is shown in fig. 6, and the map of calcium in the SEM image of fig. 6 is shown in fig. 7.
When compared with the SEM image of the powdered oligosaccharide composition of comparative example 1 shown in fig. 1, calcium stearate and magnesium stearate adhere to the particle surfaces, respectively, in the SEM images of the powdered oligosaccharide compositions of examples 1 and 2 shown in fig. 2 and 3, forming an outer layer that covers at least a part of the particle surfaces. Further, from the results of the graphs of fig. 5 and 7, it can be confirmed that the attachments are calcium stearate and magnesium stearate, respectively.
[ reference example 6 ] fluidity test of glucose
About 5g of glucose was spread on an aluminum pan and left at room temperature in the same manner as in comparative example 1, and the fluidity after 3 days was confirmed. The fluidity was evaluated in the same manner as in comparative example 1, and the result was "+" in the case where the aluminum pan was gently shaken from the side and the powder flowed as a whole. Since glucose maintains fluidity even when not added, it is known that the problem of solidification by moisture absorption even when left at room temperature is unique to oligosaccharide compositions.
Comparative example 8 and examples 3 to 7 preparation of powdery oligosaccharide compositions comprising an oligosaccharide composition derived from bagasse and various fatty acid salts and fluidity test
100 parts by weight (dry weight) of the bagasse-derived oligosaccharide composition prepared by the method of reference example 5 and 5 parts by weight of each fatty acid salt as an additive were weighed, added to a zippered plastic bag, and the bag was shaken and mixed up and down for 1 minute to prepare a powdery oligosaccharide composition. About 3g of the obtained powdered oligosaccharide composition was spread out in an aluminum pan and left to stand at room temperature, and fluidity was confirmed after 1 day and 7 days. The results of the additives and the fluidity are shown in table 4. Regarding the fluidity, the case where the aluminum plate was gently shaken from the side and the powder flowed entirely was denoted as "+", the state where the powder flowed but was partially solidified or adhered was denoted as "+", and the state where the powder was solidified, gelled or liquefied entirely was denoted as "-".
TABLE 4
Comparative examples 9 to 15 and examples 8 to 9 preparation of powdered oligosaccharide compositions comprising various oligosaccharide compositions and calcium stearate or magnesium stearate and fluidity test
100 parts by weight of the bagasse-derived oligosaccharide composition prepared by the method of reference example 5 or the commercially available powder oligosaccharide composition shown in Table 5, and 5 parts by weight of calcium stearate or magnesium stearate were weighed and mixed in a mortar to prepare a powder oligosaccharide composition. About 3g of the resulting powdered oligosaccharide composition was transferred to a glass bottle and covered with dust-free paper and rubber band. The fluidity after 14 days was confirmed by storing the samples at 30 ℃ and 75% RH. The results of the additives and the fluidity are shown in table 6. Regarding the fluidity, a state in which the bottle was gently shaken from the side and the whole powder flowed was denoted as "+", a state in which the powder was partially solidified or adhered although flowed was denoted as "+", and a state in which the powder was solidified, gelled or liquefied as a whole was denoted as "-".
TABLE 5
TABLE 6
Calcium stearate or magnesium stearate was mixed in each of the oligosaccharide compositions, but only the oligosaccharide composition derived from bagasse, which was prepared by the method of reference example 5, had the effect of maintaining fluidity (i.e., the solidification prevention effect).
Fig. 8 shows the results of observation of the particle surface of the powdery oligosaccharide composition of comparative example 12 using a scanning electron microscope apparatus. In the powder oligosaccharide composition of comparative example 12, calcium stearate adhered to form an outer layer covering at least a part of the particle surface, but as shown in table 6, the effect of maintaining fluidity (i.e., the solidification prevention effect) was not obtained.
Comparative example 16 and examples 10 to 31 preparation of powdery oligosaccharide composition comprising oligosaccharide composition derived from bagasse and calcium stearate or magnesium stearate and fluidity test
100 parts by weight of the bagasse-derived oligosaccharide composition prepared by the method of reference example 5 and 1 to 100 parts by weight of calcium stearate or magnesium stearate were weighed and mixed in a mortar to prepare a powdery oligosaccharide composition. About 3g of the resulting powdered oligosaccharide composition was transferred to a glass bottle and covered with dust-free paper and rubber band. The samples were stored at 30 ℃ and 75% RH, and the fluidity after 1 day and 10 days was confirmed. The results of the additives and the fluidity are shown in table 7. Regarding the fluidity, a state in which the bottle was gently shaken from the side and the whole powder flowed was denoted as "+", a state in which the powder was partially solidified or adhered although flowed was denoted as "+", and a state in which the powder was solidified, gelled or liquefied as a whole was denoted as "-".
TABLE 7
As a result of mixing calcium stearate or magnesium stearate with the oligosaccharide composition derived from bagasse, it was found that the effect of maintaining fluidity (i.e., the effect of preventing solidification) was confirmed when the amount of calcium stearate or magnesium stearate mixed was 1 part by weight or more relative to 100 parts by weight of the oligosaccharide composition derived from bagasse, and particularly, when the amount was 4 parts by weight or more, the effect of maintaining fluidity (i.e., the effect of preventing solidification) was high.
[ comparative examples 17 to 22 and examples 32 to 37 ] examination of the concentration of xylooligosaccharide contained in bagasse-derived oligosaccharide compositions
Oligosaccharide compositions derived from bagasse having various concentrations of xylooligosaccharide shown in table 8 were prepared by spray drying while adjusting the amount of maltodextrin added in reference example 5. Further, 100 parts by weight of each oligosaccharide composition derived from bagasse and 2 parts by weight of calcium stearate were mixed to prepare a powdery oligosaccharide composition. About 3g of each of the powdery oligosaccharide compositions and the oligosaccharide compositions derived from bagasse (in the case where calcium stearate was not mixed) were spread on an aluminum pan and left indoors, and fluidity was confirmed after 1 day, 7 days, and 21 days. The results are shown in table 9. Regarding the fluidity, a case where the aluminum plate was gently vibrated from the side and the entire powder flowed was denoted as "+", a state where a part of the powder was solidified or adhered although the powder flowed was denoted as "+", and a state where the powder was solidified, gelled or liquefied as a whole was denoted as "-".
TABLE 8
TABLE 9
It was found that the effect of preventing solidification by mixing calcium stearate was confirmed in the range of 5 to 54 wt% of xylooligosaccharide contained in the bagasse-derived oligosaccharide composition with respect to the dry weight, and particularly, the effect was maintained for a longer period of time in the range of 5 to 51 wt%.
Claims (11)
1. A powdered oligosaccharide composition comprising granules of an oligosaccharide composition derived from bagasse, and a fatty acid salt attached to the surface of the granules.
2. The powdered oligosaccharide composition of claim 1, wherein the fatty acid salt coats the surface of the granule.
3. The powdery oligosaccharide composition according to claim 1 or 2, wherein the fatty acid salt is 1 or 2 or more selected from salts of fatty acids having 12 to 22 carbon atoms.
4. The powdered oligosaccharide composition according to any one of claims 1-3, wherein the fatty acid salt is 1 or 2 or more selected from the group consisting of 1-3 valent metal salts.
5. The powdered oligosaccharide composition according to any one of claims 1-4, wherein the fatty acid salt is 1 or 2 or more selected from the group consisting of stearate, palmitate, laurate, myristate and behenate.
6. The powdered oligosaccharide composition according to any one of claims 1-5, wherein the fatty acid salt is 1 or more than 2 selected from the group consisting of sodium fatty acid, lithium fatty acid, magnesium fatty acid, calcium fatty acid, zinc fatty acid and aluminum fatty acid.
7. The powdered oligosaccharide composition according to any of claims 1-6, wherein the fatty acid salt is calcium stearate and/or magnesium stearate.
8. The powdered oligosaccharide composition according to any one of claims 1 to 7, wherein the oligosaccharide composition derived from bagasse has a main component of xylo-oligosaccharide.
9. The powdered oligosaccharide composition according to any one of claims 1-8, comprising 0.1-25 parts by weight of the fatty acid salt, relative to 100 parts by weight of the bagasse-derived oligosaccharide composition.
10. The powdered oligosaccharide composition according to any of claims 1-9, comprising 1-50 wt.% xylo-oligosaccharides from bagasse.
11. A composition comprising 0.1 to 25 parts by weight of a fatty acid salt per 100 parts by weight of a bagasse-derived oligosaccharide composition.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2020058837 | 2020-03-27 | ||
| JP2020-058837 | 2020-03-27 | ||
| PCT/JP2021/012870 WO2021193920A1 (en) | 2020-03-27 | 2021-03-26 | Powdered oligosaccharide composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN115397260A true CN115397260A (en) | 2022-11-25 |
| CN115397260B CN115397260B (en) | 2024-07-12 |
Family
ID=
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2214899A1 (en) * | 1995-03-13 | 1996-09-19 | Graham Edmund Kelly | Process for glucan preparation and therapeutic uses of glucan |
| JPH08333243A (en) * | 1995-06-05 | 1996-12-17 | Nippon Kayaku Co Ltd | Tablet having excellent touch in oral cavity |
| JP2004175713A (en) * | 2002-11-27 | 2004-06-24 | Nof Corp | Coated oligosaccharide powder, molded form thereof and method for producing the molded form |
| US20050031734A1 (en) * | 2003-03-10 | 2005-02-10 | Gang Duan | Grain compositions containing pre-biotic isomalto-oligosaccharides and methods of making and using same |
| JP2007217661A (en) * | 2006-01-17 | 2007-08-30 | Asahi Kasei Chemicals Corp | Method for producing polysacharide containing water soluble xylan, and its application |
| JP2010280601A (en) * | 2009-06-04 | 2010-12-16 | Suntory Holdings Ltd | Tablet highly containing xylo-oligosaccharide |
| WO2011108167A1 (en) * | 2010-03-05 | 2011-09-09 | 富士フイルム株式会社 | Powdered composition, cosmetic material, and method for producing powdered composition |
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2214899A1 (en) * | 1995-03-13 | 1996-09-19 | Graham Edmund Kelly | Process for glucan preparation and therapeutic uses of glucan |
| JPH08333243A (en) * | 1995-06-05 | 1996-12-17 | Nippon Kayaku Co Ltd | Tablet having excellent touch in oral cavity |
| JP2004175713A (en) * | 2002-11-27 | 2004-06-24 | Nof Corp | Coated oligosaccharide powder, molded form thereof and method for producing the molded form |
| US20050031734A1 (en) * | 2003-03-10 | 2005-02-10 | Gang Duan | Grain compositions containing pre-biotic isomalto-oligosaccharides and methods of making and using same |
| JP2007217661A (en) * | 2006-01-17 | 2007-08-30 | Asahi Kasei Chemicals Corp | Method for producing polysacharide containing water soluble xylan, and its application |
| JP2010280601A (en) * | 2009-06-04 | 2010-12-16 | Suntory Holdings Ltd | Tablet highly containing xylo-oligosaccharide |
| WO2011108167A1 (en) * | 2010-03-05 | 2011-09-09 | 富士フイルム株式会社 | Powdered composition, cosmetic material, and method for producing powdered composition |
Also Published As
| Publication number | Publication date |
|---|---|
| JPWO2021193920A1 (en) | 2021-09-30 |
| WO2021193920A1 (en) | 2021-09-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2831543C (en) | Method for producing sugar solution | |
| US20100184151A1 (en) | Method for the production of glucose from lignocellulosic feedstocks | |
| JP2015523367A (en) | Biomass conversion | |
| WO2006011479A1 (en) | Processes for producing cellooligosaccharide | |
| AU2014288309B9 (en) | Method for producing saccharide solution | |
| CA2876114C (en) | Method for producing sugar liquid | |
| CN106536743A (en) | Method for the preparation of lactic acid | |
| Yun et al. | Continuous production of inulo-oligosaccharides from chicory juice by immobilized endoinulinase | |
| CN106574278B (en) | Production of lactic acid and/or lactate from lignocellulosic material by separate saccharification and fermentation steps | |
| US10563237B2 (en) | Method for obtaining sugar derivatives | |
| CA2801258C (en) | Process for manufacturing tagatose and glucose | |
| CN115397260A (en) | Powdered oligosaccharide composition | |
| AU2017244707B2 (en) | Method for producing sugar liquor | |
| CN115397260B (en) | Powdery oligosaccharide composition | |
| WO2017142000A1 (en) | Method for producing sugar alcohol | |
| WO2012001102A1 (en) | Cellobiose production from biomass | |
| JP6357564B2 (en) | Catalyst composition for sugar condensation reaction | |
| CN105238770A (en) | Method for preparing endoinulinase through in-situ orientation dissolution and process for preparing fructo-oligosaccharide | |
| JP5367948B2 (en) | Method for producing difructose dianhydride III crystal | |
| Guerrero et al. | Lactulose | |
| WO2010067795A1 (en) | Process for producing sugar alcohol and sugar from agricultural product or agricultural by-product | |
| US11732059B2 (en) | Sphingan oligosaccharides | |
| WO2021182607A1 (en) | Diarrhea inhibitor | |
| Hedaiatnia et al. | Lactic acid production enhancement using metagenome-derived bifunctional enzyme immobilized on chitosan-alginate/nanocellulose hydrogel | |
| Masahiro et al. | Prehydrolysis of xylan in culm of Sasa kurilensis with dilute sulphuric acid |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant |