JP7445759B2 - アルロース製造用組成物及びそれを用いたアルロース製造方法 - Google Patents
アルロース製造用組成物及びそれを用いたアルロース製造方法 Download PDFInfo
- Publication number
- JP7445759B2 JP7445759B2 JP2022530303A JP2022530303A JP7445759B2 JP 7445759 B2 JP7445759 B2 JP 7445759B2 JP 2022530303 A JP2022530303 A JP 2022530303A JP 2022530303 A JP2022530303 A JP 2022530303A JP 7445759 B2 JP7445759 B2 JP 7445759B2
- Authority
- JP
- Japan
- Prior art keywords
- allulose
- disaccharide
- precursor
- weight
- present application
- 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.)
- Active
Links
- LKDRXBCSQODPBY-JDJSBBGDSA-N D-allulose Chemical compound OCC1(O)OC[C@@H](O)[C@@H](O)[C@H]1O LKDRXBCSQODPBY-JDJSBBGDSA-N 0.000 title claims description 113
- 239000000203 mixture Substances 0.000 title claims description 36
- 238000004519 manufacturing process Methods 0.000 title claims description 15
- -1 allulose disaccharide Chemical class 0.000 claims description 42
- 239000002243 precursor Substances 0.000 claims description 37
- 239000000126 substance Substances 0.000 claims description 32
- 238000010438 heat treatment Methods 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 12
- 235000013305 food Nutrition 0.000 description 24
- 150000001875 compounds Chemical class 0.000 description 14
- 150000002016 disaccharides Chemical class 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 9
- 150000001720 carbohydrates Chemical class 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 8
- 238000002474 experimental method Methods 0.000 description 8
- 238000004128 high performance liquid chromatography Methods 0.000 description 8
- 150000002772 monosaccharides Chemical class 0.000 description 8
- WVAMMOIUPISCKS-IAWWVFNNSA-N (2S,3R,4R,5R)-2-(hydroxymethyl)-2-[[(2R,3S,4R,5R)-3,4,5-trihydroxy-5-(hydroxymethyl)oxolan-2-yl]methoxy]oxane-3,4,5-triol Chemical compound OC[C@@]1([C@H](O)[C@H](O)[C@H](O)CO1)OC[C@@H]1[C@H]([C@H]([C@](CO)(O)O1)O)O WVAMMOIUPISCKS-IAWWVFNNSA-N 0.000 description 7
- WVAMMOIUPISCKS-VIJNJTOUSA-N (2S,3R,4R,5R)-2-(hydroxymethyl)-2-[[(2R,3S,4R,5S)-3,4,5-trihydroxy-5-(hydroxymethyl)oxolan-2-yl]methoxy]oxane-3,4,5-triol Chemical compound OC[C@@]1([C@H](O)[C@H](O)[C@H](O)CO1)OC[C@@H]1[C@H]([C@H]([C@@](CO)(O)O1)O)O WVAMMOIUPISCKS-VIJNJTOUSA-N 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- 239000007787 solid Substances 0.000 description 6
- 235000000346 sugar Nutrition 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- WVAMMOIUPISCKS-PCFAMRLPSA-N (2S,3R,4R,5R)-2-(hydroxymethyl)-2-[[(2R,3S,4R)-3,4,5-trihydroxy-5-(hydroxymethyl)oxolan-2-yl]methoxy]oxane-3,4,5-triol Chemical compound OC[C@]1(OC[C@H]([C@H]([C@H]1O)O)O)OC[C@H]1OC([C@@H]([C@@H]1O)O)(CO)O WVAMMOIUPISCKS-PCFAMRLPSA-N 0.000 description 4
- 230000036425 denaturation Effects 0.000 description 4
- 238000004925 denaturation Methods 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- 235000013361 beverage Nutrition 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 235000013399 edible fruits Nutrition 0.000 description 3
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 3
- 235000015203 fruit juice Nutrition 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 235000013311 vegetables Nutrition 0.000 description 3
- WVAMMOIUPISCKS-UHFFFAOYSA-N 2-(hydroxymethyl)-2-[[3,4,5-trihydroxy-5-(hydroxymethyl)oxolan-2-yl]methoxy]oxane-3,4,5-triol Chemical compound OC1C(O)C(CO)(O)OC1COC1(CO)C(O)C(O)C(O)CO1 WVAMMOIUPISCKS-UHFFFAOYSA-N 0.000 description 2
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 2
- 229930091371 Fructose Natural products 0.000 description 2
- 239000005715 Fructose Substances 0.000 description 2
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 2
- 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 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 235000002789 Panax ginseng Nutrition 0.000 description 2
- 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 2
- 239000006227 byproduct Substances 0.000 description 2
- 235000014633 carbohydrates Nutrition 0.000 description 2
- 235000014171 carbonated beverage Nutrition 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 230000007717 exclusion Effects 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 235000013355 food flavoring agent Nutrition 0.000 description 2
- 235000003599 food sweetener Nutrition 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 235000012054 meals Nutrition 0.000 description 2
- 235000013336 milk Nutrition 0.000 description 2
- 239000008267 milk Substances 0.000 description 2
- 210000004080 milk Anatomy 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000008213 purified water Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 235000015067 sauces Nutrition 0.000 description 2
- 150000008163 sugars Chemical class 0.000 description 2
- 239000003765 sweetening agent Substances 0.000 description 2
- 229910021642 ultra pure water Inorganic materials 0.000 description 2
- 239000012498 ultrapure water Substances 0.000 description 2
- RFSUNEUAIZKAJO-JDJSBBGDSA-N (3r,4s,5r)-2,5-bis(hydroxymethyl)oxolane-2,3,4-triol Chemical compound OC[C@H]1OC(O)(CO)[C@H](O)[C@@H]1O RFSUNEUAIZKAJO-JDJSBBGDSA-N 0.000 description 1
- 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 description 1
- PKAUICCNAWQPAU-UHFFFAOYSA-N 2-(4-chloro-2-methylphenoxy)acetic acid;n-methylmethanamine Chemical compound CNC.CC1=CC(Cl)=CC=C1OCC(O)=O PKAUICCNAWQPAU-UHFFFAOYSA-N 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N Acetylene Chemical compound C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 108010011485 Aspartame Proteins 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- 229920000858 Cyclodextrin Polymers 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 239000004386 Erythritol Substances 0.000 description 1
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 229920002230 Pectic acid Polymers 0.000 description 1
- 244000228451 Stevia rebaudiana Species 0.000 description 1
- 239000004376 Sucralose Substances 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 244000269722 Thea sinensis Species 0.000 description 1
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 235000013334 alcoholic beverage Nutrition 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000000605 aspartame Substances 0.000 description 1
- 235000010357 aspartame Nutrition 0.000 description 1
- IAOZJIPTCAWIRG-QWRGUYRKSA-N aspartame Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 IAOZJIPTCAWIRG-QWRGUYRKSA-N 0.000 description 1
- 229960003438 aspartame Drugs 0.000 description 1
- 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 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000015895 biscuits Nutrition 0.000 description 1
- 235000008429 bread Nutrition 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 235000019219 chocolate Nutrition 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 235000014510 cooky Nutrition 0.000 description 1
- 235000012495 crackers Nutrition 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 235000015140 cultured milk Nutrition 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 235000013325 dietary fiber Nutrition 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 235000015071 dressings Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 235000019414 erythritol Nutrition 0.000 description 1
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 description 1
- 229940009714 erythritol Drugs 0.000 description 1
- 235000013611 frozen food Nutrition 0.000 description 1
- 235000012055 fruits and vegetables Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 235000013402 health food Nutrition 0.000 description 1
- 235000020256 human milk Nutrition 0.000 description 1
- 210000004251 human milk Anatomy 0.000 description 1
- 235000015243 ice cream Nutrition 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 239000008274 jelly Substances 0.000 description 1
- 235000008960 ketchup Nutrition 0.000 description 1
- 239000002075 main ingredient Substances 0.000 description 1
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 235000021096 natural sweeteners Nutrition 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 150000002482 oligosaccharides Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000010979 pH adjustment Methods 0.000 description 1
- LCLHHZYHLXDRQG-ZNKJPWOQSA-N pectic acid Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)O[C@H](C(O)=O)[C@@H]1OC1[C@H](O)[C@@H](O)[C@@H](OC2[C@@H]([C@@H](O)[C@@H](O)[C@H](O2)C(O)=O)O)[C@@H](C(O)=O)O1 LCLHHZYHLXDRQG-ZNKJPWOQSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 239000010318 polygalacturonic acid Substances 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 150000004804 polysaccharides Chemical class 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 235000020991 processed meat Nutrition 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- HELXLJCILKEWJH-NCGAPWICSA-N rebaudioside A Chemical compound O([C@H]1[C@H](O)[C@@H](CO)O[C@H]([C@@H]1O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)O[C@]12C(=C)C[C@@]3(C1)CC[C@@H]1[C@@](C)(CCC[C@]1([C@@H]3CC2)C)C(=O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O HELXLJCILKEWJH-NCGAPWICSA-N 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 235000021067 refined food Nutrition 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 238000009938 salting Methods 0.000 description 1
- 235000013580 sausages Nutrition 0.000 description 1
- 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 description 1
- 235000011888 snacks Nutrition 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 229960002920 sorbitol Drugs 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 235000019408 sucralose Nutrition 0.000 description 1
- BAQAVOSOZGMPRM-QBMZZYIRSA-N sucralose Chemical compound O[C@@H]1[C@@H](O)[C@@H](Cl)[C@@H](CO)O[C@@H]1O[C@@]1(CCl)[C@@H](O)[C@H](O)[C@@H](CCl)O1 BAQAVOSOZGMPRM-QBMZZYIRSA-N 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000005846 sugar alcohols Chemical class 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 239000000892 thaumatin Substances 0.000 description 1
- 235000010436 thaumatin Nutrition 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 238000012795 verification Methods 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H3/00—Compounds containing only hydrogen atoms and saccharide radicals having only carbon, hydrogen, and oxygen atoms
- C07H3/02—Monosaccharides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H3/00—Compounds containing only hydrogen atoms and saccharide radicals having only carbon, hydrogen, and oxygen atoms
- C07H3/04—Disaccharides
Description
前記組成物は、糖類を含むものであってもよい。具体的には、アルロースをさらに含むものであってもよい。しかし、これらに限定されるものではない。
特許文献2に開示されているアルロース製造過程において、HPLCにより新規な物質を分離した。
ESI-MS m/z 365 [M+Na]+; 1H NMR (850 MHz, D2O) δH 3.44 (1H, d, J = 12.0 Hz), 3.47 (1H, d, J = 12.0 Hz), 3.56 (1H, dd, J = 11.0, 5.0 Hz), 3.60 (1H, d, J = 12.0 Hz), 3.62 (1H, dd, J = 11.0, 2.5 Hz), 3.70 (1H, br d, J = 12.5 Hz), 3.75 (1H, d, J = 12.0 Hz), 3.75 (1H, br ma), 3.82 (1H, br d, J = 12.5 Hz), 3.84 (1H, br s), 3.92 (1H, t, J = 3.0 Hz), 3.97 (1H, d, J = 5.5 Hz), 4.09 (1H, t, J = 5.5 Hz), 4.13 (1H, br m) [D2O signal δH 4.70]; 13C NMR signalsb δC 57.6, 60.4, 62.9, 64.7, 64.9, 69.1, 68.9, 70.2, 70.3, 81.2, 101.8, 103.4.
ESI-MS m/z 365 [M+Na]+; 1H NMR (850 MHz, D2O) δH 3.49 (1H, d, J = 13.0 Hz), 3.73 (1H, d, J = 13.0 Hz), 3.58 (1H, ma), 3.68 (1H, dd, J = 11.0, 2.5 Hz), 3.62 (1H, ma), 3.71 (1H, br d, J = 12.0 Hz), 3.82 (1H, br d, J = 12.0 Hz), 3.76 (1H, br ma), 3.78 (1H, ma), 3.87 (1H, br s), 3.98 (1H, t, J = 3.0 Hz), 3.95 (1H, d, J = 4.5 Hz), 4.00 (1H, br m), 4.34 (1H, dd, J = 8.0, 4.5 Hz) [D2O signal δH 4.70]; 13C NMR signalsb δC 57.7, 61.4, 62.2, 64.7, 64.8, 69.0, 69.2, 70.8, 74.4, 80.8, 101.8, 105.9.
実施例2-1:アルロース二糖類の加熱変換反応の比較
前述したように実施例1で分離した2種類の二糖類、D1及びD2に不純物のない超純水を添加して1%(w/w)の濃度の試料を作製し、それぞれ実験例1及び2として用いた。加熱条件による分解反応の比較のために、最も普遍的な二糖類(二量体)としてグルコース及びフルクトース各1分子で構成された砂糖(CJ第一製糖,純度99%以上)を選択し、同様に超純水を添加して1%(w/w)の濃度の試料を作製し、比較例1として用いた。
※単糖類及び二糖類の%は、分析した糖類全体に対する重量比(%,w/w)を示す。これら以外はその他の糖類に分類した。
前駆体単独ではなく、混合物内に存在する形態でも目的成分への変換が円滑であるか、アルロースを主原料として含む食品モデルに二糖類であるD1を追加して検証した。
D1のアルロースへの変換特性をさらに様々な温度及び固形分濃度条件の実験により比較した。前述したように実験した実施例2-2と同様に、純粋なアルロース単糖類に分離された前駆体であるD1を追加し、浄水を用いて固形分の濃度を調節した。作製した実験例4~6の詳細な組成を表5と表6に示す。
Claims (9)
- 前記加熱は、60℃以上100℃以下の温度で行われるものである、請求項3に記載の方法。
- 前記アルロース二糖類を含む組成物は、アルロースをさらに含むものである、請求項3に記載の方法。
- 前記組成物に含まれる前記アルロース二糖類がアルロースの前駆体である、請求項3に記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR10-2019-0156761 | 2019-11-29 | ||
KR1020190156761A KR102389709B1 (ko) | 2019-11-29 | 2019-11-29 | 알룰로스 제조용 조성물 및 이를 이용한 알룰로스의 제조 방법 |
PCT/KR2020/016551 WO2021107522A2 (ko) | 2019-11-29 | 2020-11-23 | 알룰로스 제조용 조성물 및 이를 이용한 알룰로스의 제조 방법 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2023505033A JP2023505033A (ja) | 2023-02-08 |
JP7445759B2 true JP7445759B2 (ja) | 2024-03-07 |
Family
ID=76129358
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2022530303A Active JP7445759B2 (ja) | 2019-11-29 | 2020-11-23 | アルロース製造用組成物及びそれを用いたアルロース製造方法 |
Country Status (13)
Country | Link |
---|---|
US (1) | US20230002434A1 (ja) |
EP (1) | EP4053140A4 (ja) |
JP (1) | JP7445759B2 (ja) |
KR (1) | KR102389709B1 (ja) |
CN (1) | CN114746433B (ja) |
AU (1) | AU2020391257B2 (ja) |
BR (1) | BR112022009658A2 (ja) |
CA (1) | CA3162587A1 (ja) |
CL (1) | CL2022001393A1 (ja) |
CO (1) | CO2022009062A2 (ja) |
IL (1) | IL292984A (ja) |
MX (1) | MX2022006316A (ja) |
WO (1) | WO2021107522A2 (ja) |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2018127669A1 (fr) | 2017-01-05 | 2018-07-12 | Roquette Freres | Sirops cristallisables de d-allulose |
US20190328014A1 (en) | 2017-01-05 | 2019-10-31 | Roquette Freres | Non-crystallisable d-allulose syrups |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2005110675A (ja) * | 2003-09-16 | 2005-04-28 | Meiji Univ | 低糖及び/又はオリゴ糖の製造方法、及び、機能性の低糖及び/又はオリゴ糖 |
CN1219782C (zh) * | 2003-09-28 | 2005-09-21 | 南宁市化工研究设计院 | 一种蔗糖原料高收率联产结晶果糖与甘露醇的工艺 |
JP4558093B1 (ja) * | 2009-07-16 | 2010-10-06 | 大高酵素株式会社 | 新規フラクトピラノシド型ホモオリゴ糖及びその製造方法 |
MY169490A (en) * | 2009-08-21 | 2019-04-15 | Kao Corp | Preparation method for monosaccharide,disaccharide, and/or oligosaccharide |
KR20140006026A (ko) | 2011-02-21 | 2014-01-15 | 글리콤 에이/에스 | 올리고사카라이드 전구체의 혼합물의 조성물의 촉매적 가수소분해 및 이의 용도 |
JP6099870B2 (ja) * | 2012-01-06 | 2017-03-22 | 松谷化学工業株式会社 | スクロースとd−プシコースを含む新規甘味料 |
CN103333935A (zh) * | 2013-05-24 | 2013-10-02 | 桐乡晟泰生物科技有限公司 | D-阿洛酮糖的生产工艺 |
KR101723007B1 (ko) | 2016-02-29 | 2017-04-04 | 씨제이제일제당(주) | 고순도 d-사이코스를 제조하는 방법 |
KR102072695B1 (ko) * | 2016-12-08 | 2020-03-02 | 주식회사 삼양사 | 재순환을 이용한 사이코스의 제조방법 및 장치 |
KR102004941B1 (ko) * | 2016-12-08 | 2019-07-29 | 주식회사 삼양사 | 효율적인 사이코스의 제조 방법 |
KR102064911B1 (ko) * | 2019-03-21 | 2020-01-10 | 씨제이제일제당 주식회사 | 알룰로스 유래 신규 화합물 |
KR102332373B1 (ko) * | 2019-11-29 | 2021-11-29 | 씨제이제일제당 주식회사 | 알룰로스 이당류를 포함하는 hmf 생성 억제용 조성물 |
-
2019
- 2019-11-29 KR KR1020190156761A patent/KR102389709B1/ko active IP Right Grant
-
2020
- 2020-11-23 JP JP2022530303A patent/JP7445759B2/ja active Active
- 2020-11-23 CA CA3162587A patent/CA3162587A1/en active Pending
- 2020-11-23 WO PCT/KR2020/016551 patent/WO2021107522A2/ko unknown
- 2020-11-23 MX MX2022006316A patent/MX2022006316A/es unknown
- 2020-11-23 EP EP20893834.0A patent/EP4053140A4/en active Pending
- 2020-11-23 BR BR112022009658A patent/BR112022009658A2/pt unknown
- 2020-11-23 AU AU2020391257A patent/AU2020391257B2/en active Active
- 2020-11-23 US US17/779,043 patent/US20230002434A1/en active Pending
- 2020-11-23 IL IL292984A patent/IL292984A/en unknown
- 2020-11-23 CN CN202080082111.5A patent/CN114746433B/zh active Active
-
2022
- 2022-05-27 CL CL2022001393A patent/CL2022001393A1/es unknown
- 2022-06-29 CO CONC2022/0009062A patent/CO2022009062A2/es unknown
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2018127669A1 (fr) | 2017-01-05 | 2018-07-12 | Roquette Freres | Sirops cristallisables de d-allulose |
US20190328014A1 (en) | 2017-01-05 | 2019-10-31 | Roquette Freres | Non-crystallisable d-allulose syrups |
Also Published As
Publication number | Publication date |
---|---|
CN114746433B (zh) | 2024-01-23 |
AU2020391257A1 (en) | 2022-06-09 |
CA3162587A1 (en) | 2021-06-03 |
WO2021107522A2 (ko) | 2021-06-03 |
US20230002434A1 (en) | 2023-01-05 |
KR20210067301A (ko) | 2021-06-08 |
JP2023505033A (ja) | 2023-02-08 |
MX2022006316A (es) | 2022-06-22 |
CO2022009062A2 (es) | 2022-07-19 |
EP4053140A2 (en) | 2022-09-07 |
IL292984A (en) | 2022-07-01 |
EP4053140A4 (en) | 2023-03-08 |
AU2020391257B2 (en) | 2023-12-07 |
CN114746433A (zh) | 2022-07-12 |
KR102389709B1 (ko) | 2022-04-22 |
WO2021107522A3 (ko) | 2021-07-15 |
BR112022009658A2 (pt) | 2022-08-16 |
CL2022001393A1 (es) | 2023-01-06 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP2662381B1 (en) | Sugar condensate, method for producing same, and application therefor | |
JP7146760B2 (ja) | レバウディオサイドjを含む組成物 | |
JP2024045335A (ja) | アルロース二糖類を含むhmf生成抑制用組成物 | |
WO2002072594A1 (fr) | Tetrasaccharide cyclique ramifie et procede de production correspondant | |
JP2823640B2 (ja) | 腸内フローラ改善物質 | |
JP7445759B2 (ja) | アルロース製造用組成物及びそれを用いたアルロース製造方法 | |
JP6382058B2 (ja) | 糖縮合物の製造法 | |
EP3733682B1 (en) | Novel allulose-derived compound | |
JP4102573B2 (ja) | 環状四糖の製造方法 | |
JP6636003B2 (ja) | 糖組成物の製造方法及び糖組成物 | |
JP6588071B2 (ja) | β−D−グルコピラノシル−(1→1)−D−フルクトース及びその用途 | |
JP7408393B2 (ja) | 低カロリー化飲料およびその製造方法 | |
JP2021533814A (ja) | 果菜ドリンク |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20220524 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20230613 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20230911 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20231128 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20231206 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20240213 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20240226 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 7445759 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |