CA2954662C - Oligosaccharide compositions and methods for producing thereof - Google Patents
Oligosaccharide compositions and methods for producing thereof Download PDFInfo
- Publication number
- CA2954662C CA2954662C CA2954662A CA2954662A CA2954662C CA 2954662 C CA2954662 C CA 2954662C CA 2954662 A CA2954662 A CA 2954662A CA 2954662 A CA2954662 A CA 2954662A CA 2954662 C CA2954662 C CA 2954662C
- Authority
- CA
- Canada
- Prior art keywords
- acid
- supported
- oligosaccharide composition
- catalyst
- polymeric
- 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
- 150000002482 oligosaccharides Chemical class 0.000 title claims abstract description 389
- 229920001542 oligosaccharide Polymers 0.000 title claims abstract description 386
- 239000000203 mixture Substances 0.000 title claims abstract description 289
- 238000000034 method Methods 0.000 title abstract description 247
- 150000002772 monosaccharides Chemical class 0.000 claims abstract description 101
- 239000000178 monomer Substances 0.000 claims description 243
- 239000007787 solid Substances 0.000 claims description 119
- -1 galacitol Chemical compound 0.000 claims description 117
- 125000000524 functional group Chemical group 0.000 claims description 63
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 54
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 48
- 229910001868 water Inorganic materials 0.000 claims description 47
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 45
- 238000006116 polymerization reaction Methods 0.000 claims description 37
- 230000000694 effects Effects 0.000 claims description 29
- 239000002253 acid Substances 0.000 claims description 28
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 27
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 24
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 claims description 22
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical group [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 22
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 21
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 claims description 21
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 claims description 21
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 21
- 239000008103 glucose Substances 0.000 claims description 21
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 20
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 20
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 claims description 19
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 18
- 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 claims description 18
- 229930182830 galactose Natural products 0.000 claims description 18
- 229910019142 PO4 Chemical group 0.000 claims description 17
- JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 claims description 16
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 claims description 16
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 16
- 150000001298 alcohols Chemical group 0.000 claims description 15
- 235000001014 amino acid Nutrition 0.000 claims description 15
- 150000001413 amino acids Chemical group 0.000 claims description 15
- 235000013325 dietary fiber Nutrition 0.000 claims description 15
- 150000005846 sugar alcohols Chemical group 0.000 claims description 14
- 235000020357 syrup Nutrition 0.000 claims description 13
- 239000006188 syrup Substances 0.000 claims description 13
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims description 12
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 12
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 12
- 239000004220 glutamic acid Substances 0.000 claims description 12
- 235000013922 glutamic acid Nutrition 0.000 claims description 12
- 150000002337 glycosamines Chemical group 0.000 claims description 12
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical group [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 12
- 239000010452 phosphate Chemical group 0.000 claims description 12
- 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 claims description 11
- 150000001735 carboxylic acids Chemical group 0.000 claims description 11
- 150000002016 disaccharides Chemical class 0.000 claims description 11
- 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 claims description 10
- SHZGCJCMOBCMKK-UHFFFAOYSA-N D-mannomethylose Natural products CC1OC(O)C(O)C(O)C1O SHZGCJCMOBCMKK-UHFFFAOYSA-N 0.000 claims description 10
- 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 claims description 10
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 10
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims description 10
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 claims description 10
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 claims description 10
- PYMYPHUHKUWMLA-WDCZJNDASA-N arabinose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WDCZJNDASA-N 0.000 claims description 10
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 claims description 10
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 claims description 10
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 10
- VQHSOMBJVWLPSR-JVCRWLNRSA-N lactitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O VQHSOMBJVWLPSR-JVCRWLNRSA-N 0.000 claims description 10
- 239000000600 sorbitol Substances 0.000 claims description 10
- 235000010356 sorbitol Nutrition 0.000 claims description 10
- 239000000811 xylitol Substances 0.000 claims description 10
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 claims description 10
- 235000010447 xylitol Nutrition 0.000 claims description 10
- 229960002675 xylitol Drugs 0.000 claims description 10
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims description 9
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims description 9
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 9
- HEBKCHPVOIAQTA-QWWZWVQMSA-N D-arabinitol Chemical compound OC[C@@H](O)C(O)[C@H](O)CO HEBKCHPVOIAQTA-QWWZWVQMSA-N 0.000 claims description 9
- OXQKEKGBFMQTML-UHFFFAOYSA-N D-glycero-D-gluco-heptitol Natural products OCC(O)C(O)C(O)C(O)C(O)CO OXQKEKGBFMQTML-UHFFFAOYSA-N 0.000 claims description 9
- FBPFZTCFMRRESA-ZXXMMSQZSA-N D-iditol Chemical compound OC[C@@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-ZXXMMSQZSA-N 0.000 claims description 9
- 239000004386 Erythritol Substances 0.000 claims description 9
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 claims description 9
- SKCKOFZKJLZSFA-UHFFFAOYSA-N L-Gulomethylit Natural products CC(O)C(O)C(O)C(O)CO SKCKOFZKJLZSFA-UHFFFAOYSA-N 0.000 claims description 9
- 229930195725 Mannitol Natural products 0.000 claims description 9
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 9
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 9
- 150000007513 acids Chemical class 0.000 claims description 9
- 239000001361 adipic acid Substances 0.000 claims description 9
- 235000011037 adipic acid Nutrition 0.000 claims description 9
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims description 9
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 9
- 150000001720 carbohydrates Chemical class 0.000 claims description 9
- 235000014633 carbohydrates Nutrition 0.000 claims description 9
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 claims description 9
- 235000019414 erythritol Nutrition 0.000 claims description 9
- 229940009714 erythritol Drugs 0.000 claims description 9
- SKCKOFZKJLZSFA-FSIIMWSLSA-N fucitol Chemical compound C[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO SKCKOFZKJLZSFA-FSIIMWSLSA-N 0.000 claims description 9
- 235000011187 glycerol Nutrition 0.000 claims description 9
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 9
- 239000011976 maleic acid Substances 0.000 claims description 9
- 239000001630 malic acid Substances 0.000 claims description 9
- 235000011090 malic acid Nutrition 0.000 claims description 9
- 239000000594 mannitol Substances 0.000 claims description 9
- 235000010355 mannitol Nutrition 0.000 claims description 9
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 9
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 9
- OXQKEKGBFMQTML-KVTDHHQDSA-N volemitol Chemical compound OC[C@@H](O)[C@@H](O)C(O)[C@H](O)[C@H](O)CO OXQKEKGBFMQTML-KVTDHHQDSA-N 0.000 claims description 9
- MSWZFWKMSRAUBD-GASJEMHNSA-N 2-amino-2-deoxy-D-galactopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@H](O)[C@@H]1O MSWZFWKMSRAUBD-GASJEMHNSA-N 0.000 claims description 8
- MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 claims description 8
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 8
- 229930091371 Fructose Natural products 0.000 claims description 8
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 claims description 8
- 239000005715 Fructose Substances 0.000 claims description 8
- SQUHHTBVTRBESD-UHFFFAOYSA-N Hexa-Ac-myo-Inositol Natural products CC(=O)OC1C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C1OC(C)=O SQUHHTBVTRBESD-UHFFFAOYSA-N 0.000 claims description 8
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims description 8
- 235000003704 aspartic acid Nutrition 0.000 claims description 8
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims description 8
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 claims description 8
- 235000015165 citric acid Nutrition 0.000 claims description 8
- 235000019253 formic acid Nutrition 0.000 claims description 8
- 229960002442 glucosamine Drugs 0.000 claims description 8
- CDAISMWEOUEBRE-GPIVLXJGSA-N inositol Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O CDAISMWEOUEBRE-GPIVLXJGSA-N 0.000 claims description 8
- 229960000367 inositol Drugs 0.000 claims description 8
- 229940040102 levulinic acid Drugs 0.000 claims description 8
- UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical compound CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 claims description 8
- CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 claims description 8
- GWYFCOCPABKNJV-UHFFFAOYSA-N beta-methyl-butyric acid Natural products CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims description 7
- 239000000843 powder Substances 0.000 claims description 7
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 claims description 7
- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 claims description 6
- 229940097043 glucuronic acid Drugs 0.000 claims description 6
- 150000003077 polyols Chemical class 0.000 claims description 6
- 235000019260 propionic acid Nutrition 0.000 claims description 6
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 6
- XYHKNCXZYYTLRG-UHFFFAOYSA-N 1h-imidazole-2-carbaldehyde Chemical compound O=CC1=NC=CN1 XYHKNCXZYYTLRG-UHFFFAOYSA-N 0.000 claims description 5
- GWYFCOCPABKNJV-UHFFFAOYSA-M 3-Methylbutanoic acid Natural products CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 claims description 5
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 5
- WQZGKKKJIJFFOK-IVMDWMLBSA-N D-allopyranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@H](O)[C@@H]1O WQZGKKKJIJFFOK-IVMDWMLBSA-N 0.000 claims description 5
- HMFHBZSHGGEWLO-SOOFDHNKSA-N D-ribofuranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-SOOFDHNKSA-N 0.000 claims description 5
- 102000004190 Enzymes Human genes 0.000 claims description 5
- 108090000790 Enzymes Proteins 0.000 claims description 5
- PNNNRSAQSRJVSB-SLPGGIOYSA-N Fucose Natural products C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C=O PNNNRSAQSRJVSB-SLPGGIOYSA-N 0.000 claims description 5
- SHZGCJCMOBCMKK-DHVFOXMCSA-N L-fucopyranose Chemical compound C[C@@H]1OC(O)[C@@H](O)[C@H](O)[C@@H]1O SHZGCJCMOBCMKK-DHVFOXMCSA-N 0.000 claims description 5
- SHZGCJCMOBCMKK-JFNONXLTSA-N L-rhamnopyranose Chemical compound C[C@@H]1OC(O)[C@H](O)[C@H](O)[C@H]1O SHZGCJCMOBCMKK-JFNONXLTSA-N 0.000 claims description 5
- PNNNRSAQSRJVSB-UHFFFAOYSA-N L-rhamnose Natural products CC(O)C(O)C(O)C(O)C=O PNNNRSAQSRJVSB-UHFFFAOYSA-N 0.000 claims description 5
- PYMYPHUHKUWMLA-LMVFSUKVSA-N Ribose Natural products OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 claims description 5
- HMFHBZSHGGEWLO-UHFFFAOYSA-N alpha-D-Furanose-Ribose Natural products OCC1OC(O)C(O)C1O HMFHBZSHGGEWLO-UHFFFAOYSA-N 0.000 claims description 5
- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 claims description 5
- 239000006227 byproduct Substances 0.000 claims description 5
- 229940013688 formic acid Drugs 0.000 claims description 5
- 239000004310 lactic acid Substances 0.000 claims description 5
- 235000014655 lactic acid Nutrition 0.000 claims description 5
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 5
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 5
- 229940107700 pyruvic acid Drugs 0.000 claims description 5
- 210000002784 stomach Anatomy 0.000 claims description 5
- 229940005605 valeric acid Drugs 0.000 claims description 5
- 239000002663 humin Substances 0.000 claims description 4
- 229920005862 polyol Polymers 0.000 claims description 4
- 210000000813 small intestine Anatomy 0.000 claims description 4
- 108091005804 Peptidases Proteins 0.000 claims description 3
- 239000004365 Protease Substances 0.000 claims description 3
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 claims description 3
- 108010073178 Glucan 1,4-alpha-Glucosidase Proteins 0.000 claims description 2
- 229940088598 enzyme Drugs 0.000 claims 3
- AEMOLEFTQBMNLQ-AQKNRBDQSA-N D-glucopyranuronic acid Chemical compound OC1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-AQKNRBDQSA-N 0.000 claims 2
- 102000004139 alpha-Amylases Human genes 0.000 claims 1
- 108090000637 alpha-Amylases Proteins 0.000 claims 1
- 229940024171 alpha-amylase Drugs 0.000 claims 1
- 239000003054 catalyst Substances 0.000 abstract description 547
- 235000000346 sugar Nutrition 0.000 abstract description 185
- 230000002378 acidificating effect Effects 0.000 abstract description 131
- 150000008163 sugars Chemical class 0.000 abstract description 119
- 238000004519 manufacturing process Methods 0.000 abstract description 30
- 125000003010 ionic group Chemical group 0.000 abstract description 8
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 210
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 185
- 229940116441 divinylbenzene Drugs 0.000 description 179
- 150000001875 compounds Chemical class 0.000 description 135
- 125000002091 cationic group Chemical group 0.000 description 133
- 125000003118 aryl group Chemical group 0.000 description 88
- 238000006243 chemical reaction Methods 0.000 description 78
- 229920000642 polymer Polymers 0.000 description 77
- 125000001072 heteroaryl group Chemical group 0.000 description 75
- 125000005647 linker group Chemical group 0.000 description 69
- 125000000217 alkyl group Chemical group 0.000 description 57
- 150000007516 brønsted-lowry acids Chemical class 0.000 description 53
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 48
- 239000011541 reaction mixture Substances 0.000 description 47
- 125000001424 substituent group Chemical group 0.000 description 47
- 125000000753 cycloalkyl group Chemical group 0.000 description 46
- 238000007306 functionalization reaction Methods 0.000 description 42
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 42
- 229910052739 hydrogen Inorganic materials 0.000 description 40
- 125000005842 heteroatom Chemical group 0.000 description 36
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 35
- 125000003342 alkenyl group Chemical group 0.000 description 35
- 125000005843 halogen group Chemical group 0.000 description 34
- 229910052799 carbon Inorganic materials 0.000 description 33
- 229910052757 nitrogen Inorganic materials 0.000 description 33
- 239000001257 hydrogen Substances 0.000 description 32
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 32
- 239000000047 product Substances 0.000 description 32
- 125000000623 heterocyclic group Chemical group 0.000 description 31
- 125000000304 alkynyl group Chemical group 0.000 description 30
- 125000004404 heteroalkyl group Chemical group 0.000 description 30
- 150000004676 glycans Chemical class 0.000 description 29
- 229920001282 polysaccharide Polymers 0.000 description 29
- 239000005017 polysaccharide Substances 0.000 description 29
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 28
- QAOWNCQODCNURD-UHFFFAOYSA-M bisulphate group Chemical group S([O-])(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 27
- 239000000463 material Substances 0.000 description 27
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 26
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 26
- 230000008569 process Effects 0.000 description 25
- 125000004429 atom Chemical group 0.000 description 24
- 125000004432 carbon atom Chemical group C* 0.000 description 23
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 22
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- 229910052760 oxygen Inorganic materials 0.000 description 21
- 239000001301 oxygen Chemical group 0.000 description 21
- 239000002002 slurry Substances 0.000 description 21
- 229910052717 sulfur Chemical group 0.000 description 21
- 229920005989 resin Polymers 0.000 description 20
- 239000011347 resin Substances 0.000 description 20
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 19
- 230000003197 catalytic effect Effects 0.000 description 19
- 125000004043 oxo group Chemical group O=* 0.000 description 19
- 238000003756 stirring Methods 0.000 description 19
- 239000011593 sulfur Chemical group 0.000 description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical group CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 18
- 125000001188 haloalkyl group Chemical group 0.000 description 18
- 239000002245 particle Substances 0.000 description 18
- 238000002360 preparation method Methods 0.000 description 18
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 17
- 125000002947 alkylene group Chemical group 0.000 description 17
- 239000011521 glass Substances 0.000 description 17
- 229960001031 glucose Drugs 0.000 description 17
- 239000000126 substance Substances 0.000 description 17
- 125000001165 hydrophobic group Chemical group 0.000 description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 14
- 238000004132 cross linking Methods 0.000 description 14
- 125000004433 nitrogen atom Chemical group N* 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- YJVYNRXKVDZAAX-UHFFFAOYSA-N C(=O)O.P(O)(O)=O Chemical compound C(=O)O.P(O)(O)=O YJVYNRXKVDZAAX-UHFFFAOYSA-N 0.000 description 13
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 13
- 239000008367 deionised water Substances 0.000 description 13
- 235000021317 phosphate Nutrition 0.000 description 13
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 13
- 239000002952 polymeric resin Substances 0.000 description 13
- 239000000376 reactant Substances 0.000 description 13
- 229920003002 synthetic resin Polymers 0.000 description 13
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 12
- 240000008042 Zea mays Species 0.000 description 12
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 12
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 12
- 229940024606 amino acid Drugs 0.000 description 12
- 239000011162 core material Substances 0.000 description 12
- 235000005822 corn Nutrition 0.000 description 12
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 11
- JWQNMZVYTPNHKI-UHFFFAOYSA-N Br.P(O)(O)=O Chemical compound Br.P(O)(O)=O JWQNMZVYTPNHKI-UHFFFAOYSA-N 0.000 description 11
- YXNNSWYDFRWCBQ-UHFFFAOYSA-N C(C)(=O)O.P(O)(O)=O Chemical compound C(C)(=O)O.P(O)(O)=O YXNNSWYDFRWCBQ-UHFFFAOYSA-N 0.000 description 11
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 11
- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 description 11
- 125000003545 alkoxy group Chemical group 0.000 description 11
- 125000000392 cycloalkenyl group Chemical group 0.000 description 11
- 230000009477 glass transition Effects 0.000 description 11
- 230000002209 hydrophobic effect Effects 0.000 description 11
- 241000894007 species Species 0.000 description 11
- 238000004448 titration Methods 0.000 description 11
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 10
- 238000010923 batch production Methods 0.000 description 10
- 238000010924 continuous production Methods 0.000 description 10
- 230000007935 neutral effect Effects 0.000 description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
- RIOQSEWOXXDEQQ-UHFFFAOYSA-O triphenylphosphanium Chemical compound C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-O 0.000 description 10
- 241001465754 Metazoa Species 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 125000004452 carbocyclyl group Chemical group 0.000 description 9
- 125000004122 cyclic group Chemical group 0.000 description 9
- 150000002148 esters Chemical group 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- 238000004128 high performance liquid chromatography Methods 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- 125000003367 polycyclic group Chemical group 0.000 description 9
- 238000012545 processing Methods 0.000 description 9
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 9
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose 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](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- 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 8
- 229910002651 NO3 Inorganic materials 0.000 description 8
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 8
- 239000008101 lactose Substances 0.000 description 8
- 125000002950 monocyclic group Chemical group 0.000 description 8
- 125000006413 ring segment Chemical group 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- RDVLKFWQJDSWBB-UHFFFAOYSA-N Cl.OP(O)=O Chemical compound Cl.OP(O)=O RDVLKFWQJDSWBB-UHFFFAOYSA-N 0.000 description 7
- 239000004793 Polystyrene Substances 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 7
- 238000009826 distribution Methods 0.000 description 7
- 229920002223 polystyrene Polymers 0.000 description 7
- 229920002451 polyvinyl alcohol Polymers 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 7
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 7
- 238000003828 vacuum filtration Methods 0.000 description 7
- 229920002245 Dextrose equivalent Polymers 0.000 description 6
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 6
- 239000004372 Polyvinyl alcohol Substances 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 6
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 6
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 6
- 150000001450 anions Chemical class 0.000 description 6
- 229960005261 aspartic acid Drugs 0.000 description 6
- 239000011324 bead Substances 0.000 description 6
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 6
- 239000007857 degradation product Substances 0.000 description 6
- 235000013305 food Nutrition 0.000 description 6
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 6
- 125000004438 haloalkoxy group Chemical group 0.000 description 6
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 6
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 125000004076 pyridyl group Chemical group 0.000 description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 6
- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 6
- 239000004698 Polyethylene Substances 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 5
- 125000003368 amide group Chemical group 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- 239000003125 aqueous solvent Substances 0.000 description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- 125000004093 cyano group Chemical group *C#N 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- 150000004693 imidazolium salts Chemical group 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 125000006574 non-aromatic ring group Chemical group 0.000 description 5
- 235000016709 nutrition Nutrition 0.000 description 5
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 5
- 229920000573 polyethylene Polymers 0.000 description 5
- 238000004064 recycling Methods 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 5
- 229910010271 silicon carbide Inorganic materials 0.000 description 5
- 239000000377 silicon dioxide Substances 0.000 description 5
- 125000000542 sulfonic acid group Chemical group 0.000 description 5
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 description 4
- ORECNKBJIMKZNX-UHFFFAOYSA-N 1,3-thiazol-3-ium;chloride Chemical compound Cl.C1=CSC=N1 ORECNKBJIMKZNX-UHFFFAOYSA-N 0.000 description 4
- 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 4
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 4
- MNQZXJOMYWMBOU-VKHMYHEASA-N D-glyceraldehyde Chemical compound OC[C@@H](O)C=O MNQZXJOMYWMBOU-VKHMYHEASA-N 0.000 description 4
- 241000282412 Homo Species 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 229920002472 Starch Polymers 0.000 description 4
- IAJILQKETJEXLJ-QTBDOELSSA-N aldehydo-D-glucuronic acid Chemical compound O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C(O)=O IAJILQKETJEXLJ-QTBDOELSSA-N 0.000 description 4
- 125000004450 alkenylene group Chemical group 0.000 description 4
- 125000000732 arylene group Chemical group 0.000 description 4
- 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 4
- 239000001913 cellulose Substances 0.000 description 4
- 229920002678 cellulose Polymers 0.000 description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
- 230000003247 decreasing effect Effects 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
- 230000036541 health Effects 0.000 description 4
- 125000005549 heteroarylene group Chemical group 0.000 description 4
- 229920000140 heteropolymer Polymers 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- TWNIBLMWSKIRAT-VFUOTHLCSA-N levoglucosan Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@H]2CO[C@@H]1O2 TWNIBLMWSKIRAT-VFUOTHLCSA-N 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-O morpholinium Chemical compound [H+].C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-O 0.000 description 4
- 239000012508 resin bead Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 235000019698 starch Nutrition 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- 125000000547 substituted alkyl group Chemical group 0.000 description 4
- 125000003107 substituted aryl group Chemical group 0.000 description 4
- 235000011149 sulphuric acid Nutrition 0.000 description 4
- RXJKFRMDXUJTEX-UHFFFAOYSA-O triethylphosphanium Chemical compound CC[PH+](CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-O 0.000 description 4
- YWWDBCBWQNCYNR-UHFFFAOYSA-O trimethylphosphanium Chemical compound C[PH+](C)C YWWDBCBWQNCYNR-UHFFFAOYSA-O 0.000 description 4
- KCTAHLRCZMOTKM-UHFFFAOYSA-O tripropylphosphanium Chemical compound CCC[PH+](CCC)CCC KCTAHLRCZMOTKM-UHFFFAOYSA-O 0.000 description 4
- 239000010457 zeolite Substances 0.000 description 4
- DDGHBOLOCQWPKE-UHFFFAOYSA-N 1,3-thiazole;hydrobromide Chemical compound [Br-].C1=CSC=[NH+]1 DDGHBOLOCQWPKE-UHFFFAOYSA-N 0.000 description 3
- JDIIGWSSTNUWGK-UHFFFAOYSA-N 1h-imidazol-3-ium;chloride Chemical compound [Cl-].[NH2+]1C=CN=C1 JDIIGWSSTNUWGK-UHFFFAOYSA-N 0.000 description 3
- 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 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 150000001204 N-oxides Chemical class 0.000 description 3
- NQRYJNQNLNOLGT-UHFFFAOYSA-O Piperidinium(1+) Chemical compound C1CC[NH2+]CC1 NQRYJNQNLNOLGT-UHFFFAOYSA-O 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 3
- WTKZEGDFNFYCGP-UHFFFAOYSA-O Pyrazolium Chemical compound C1=CN[NH+]=C1 WTKZEGDFNFYCGP-UHFFFAOYSA-O 0.000 description 3
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 description 3
- 229910003481 amorphous carbon Inorganic materials 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000002619 bicyclic group Chemical group 0.000 description 3
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 3
- 125000002837 carbocyclic group Chemical group 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 125000002843 carboxylic acid group Chemical group 0.000 description 3
- 238000005119 centrifugation Methods 0.000 description 3
- 239000000919 ceramic Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 235000019621 digestibility Nutrition 0.000 description 3
- 238000012674 dispersion polymerization Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 238000000855 fermentation Methods 0.000 description 3
- 230000004151 fermentation Effects 0.000 description 3
- 210000001035 gastrointestinal tract Anatomy 0.000 description 3
- 229960002989 glutamic acid Drugs 0.000 description 3
- 230000005484 gravity Effects 0.000 description 3
- 244000005709 gut microbiome Species 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-O hydron;pyrimidine Chemical compound C1=CN=C[NH+]=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-O 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- 229910052738 indium Inorganic materials 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 3
- 239000000395 magnesium oxide Substances 0.000 description 3
- 239000000391 magnesium silicate Substances 0.000 description 3
- 229910052919 magnesium silicate Inorganic materials 0.000 description 3
- 235000019792 magnesium silicate Nutrition 0.000 description 3
- 239000000696 magnetic material Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 3
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 3
- 229920001155 polypropylene Polymers 0.000 description 3
- 229920000915 polyvinyl chloride Polymers 0.000 description 3
- 239000004800 polyvinyl chloride Substances 0.000 description 3
- 239000011148 porous material Substances 0.000 description 3
- 238000011085 pressure filtration Methods 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000012086 standard solution Substances 0.000 description 3
- 239000008107 starch Substances 0.000 description 3
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- TUQOTMZNTHZOKS-UHFFFAOYSA-O tributylphosphanium Chemical compound CCCC[PH+](CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-O 0.000 description 3
- 150000004043 trisaccharides Chemical class 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 2
- 125000006706 (C3-C6) carbocyclyl group Chemical group 0.000 description 2
- PFNQVRZLDWYSCW-UHFFFAOYSA-N (fluoren-9-ylideneamino) n-naphthalen-1-ylcarbamate Chemical compound C12=CC=CC=C2C2=CC=CC=C2C1=NOC(=O)NC1=CC=CC2=CC=CC=C12 PFNQVRZLDWYSCW-UHFFFAOYSA-N 0.000 description 2
- KNKRKFALVUDBJE-UHFFFAOYSA-N 1,2-dichloropropane Chemical compound CC(Cl)CCl KNKRKFALVUDBJE-UHFFFAOYSA-N 0.000 description 2
- GIQQAQFTVJTULV-UHFFFAOYSA-N 1,3-oxazol-3-ium;chloride Chemical compound Cl.C1=COC=N1 GIQQAQFTVJTULV-UHFFFAOYSA-N 0.000 description 2
- IVODAIGHBCWWFM-UHFFFAOYSA-N 1,3-oxazole;hydrobromide Chemical compound Br.C1=COC=N1 IVODAIGHBCWWFM-UHFFFAOYSA-N 0.000 description 2
- BLUOWRLMTJHKTC-UHFFFAOYSA-N 1H-pyrazol-1-ium formate Chemical compound [O-]C=O.[NH2+]1C=CC=N1 BLUOWRLMTJHKTC-UHFFFAOYSA-N 0.000 description 2
- VWUCIBOKNZGWLX-UHFFFAOYSA-N 1h-imidazol-1-ium;bromide Chemical compound [Br-].C1=C[NH+]=CN1 VWUCIBOKNZGWLX-UHFFFAOYSA-N 0.000 description 2
- HZFIOFGZCRLYOH-UHFFFAOYSA-N 1h-pyrazol-1-ium;bromide Chemical compound Br.C=1C=NNC=1 HZFIOFGZCRLYOH-UHFFFAOYSA-N 0.000 description 2
- JHTKOUJDEUQFOB-UHFFFAOYSA-N 1h-pyrazol-1-ium;chloride Chemical compound Cl.C=1C=NNC=1 JHTKOUJDEUQFOB-UHFFFAOYSA-N 0.000 description 2
- LFDGRWDETVOGDT-UHFFFAOYSA-N 1h-pyrrole;hydrochloride Chemical compound Cl.C=1C=CNC=1 LFDGRWDETVOGDT-UHFFFAOYSA-N 0.000 description 2
- YAZXXAOXRDUGDH-UHFFFAOYSA-N 1h-pyrrole;sulfuric acid Chemical compound C=1C=CNC=1.OS(O)(=O)=O YAZXXAOXRDUGDH-UHFFFAOYSA-N 0.000 description 2
- YXQVALAGDPVRRY-UHFFFAOYSA-N 2-acetylimidazole-1-sulfonic acid Chemical compound CC(=O)C1=NC=CN1S(O)(=O)=O YXQVALAGDPVRRY-UHFFFAOYSA-N 0.000 description 2
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 2
- AFUMJKIGTDITJU-UHFFFAOYSA-N 2h-thiazine;hydrochloride Chemical compound Cl.N1SC=CC=C1 AFUMJKIGTDITJU-UHFFFAOYSA-N 0.000 description 2
- NOEGNKMFWQHSLB-UHFFFAOYSA-N 5-hydroxymethylfurfural Chemical compound OCC1=CC=C(C=O)O1 NOEGNKMFWQHSLB-UHFFFAOYSA-N 0.000 description 2
- 239000004382 Amylase Substances 0.000 description 2
- UQAUZQARLQGLIX-UHFFFAOYSA-N C(=O)O.C(C)P(CC)CC Chemical compound C(=O)O.C(C)P(CC)CC UQAUZQARLQGLIX-UHFFFAOYSA-N 0.000 description 2
- WJYLUGHLAOFHDG-UHFFFAOYSA-N C(=O)O.C(CCC)P(CCCC)CCCC Chemical compound C(=O)O.C(CCC)P(CCCC)CCCC WJYLUGHLAOFHDG-UHFFFAOYSA-N 0.000 description 2
- SWEWHZHUPDSUNO-UHFFFAOYSA-N C(=O)O.FP(F)F Chemical compound C(=O)O.FP(F)F SWEWHZHUPDSUNO-UHFFFAOYSA-N 0.000 description 2
- RDVXKIOXGQVMMO-UHFFFAOYSA-N C(=O)[O-].C[PH+](C)C Chemical compound C(=O)[O-].C[PH+](C)C RDVXKIOXGQVMMO-UHFFFAOYSA-N 0.000 description 2
- ZGHYVBPAFUTXFV-UHFFFAOYSA-N C(C)(=O)O.C(CC)P(CCC)CCC Chemical compound C(C)(=O)O.C(CC)P(CCC)CCC ZGHYVBPAFUTXFV-UHFFFAOYSA-N 0.000 description 2
- LTVPBZZJQJFFNW-UHFFFAOYSA-N C(C)(=O)O.P(O)(O)=O.N1=CN=CC=C1 Chemical compound C(C)(=O)O.P(O)(O)=O.N1=CN=CC=C1 LTVPBZZJQJFFNW-UHFFFAOYSA-N 0.000 description 2
- WCSXXRICXWKQQF-UHFFFAOYSA-N CC(O)=O.OP(O)=O.FP(F)F Chemical compound CC(O)=O.OP(O)=O.FP(F)F WCSXXRICXWKQQF-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-CUHNMECISA-N D-Cellobiose 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)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-CUHNMECISA-N 0.000 description 2
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 2
- HOJPSWGZBWEFOB-UHFFFAOYSA-N FP(F)F.Br Chemical compound FP(F)F.Br HOJPSWGZBWEFOB-UHFFFAOYSA-N 0.000 description 2
- QHLAYFMDLBCWIU-UHFFFAOYSA-N FP(F)F.Cl Chemical compound FP(F)F.Cl QHLAYFMDLBCWIU-UHFFFAOYSA-N 0.000 description 2
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 2
- 229920002907 Guar gum Polymers 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical compound [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 240000007049 Juglans regia Species 0.000 description 2
- 235000009496 Juglans regia Nutrition 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- QWARTHJCYCGFEF-UHFFFAOYSA-N OC=O.OP(O)=O.FP(F)F Chemical compound OC=O.OP(O)=O.FP(F)F QWARTHJCYCGFEF-UHFFFAOYSA-N 0.000 description 2
- CUECCOPJUSFMMM-UHFFFAOYSA-N OP(O)=O.FP(F)F.Br Chemical compound OP(O)=O.FP(F)F.Br CUECCOPJUSFMMM-UHFFFAOYSA-N 0.000 description 2
- JPAQBDOJXCMDRF-UHFFFAOYSA-N OP(O)=O.FP(F)F.Cl Chemical compound OP(O)=O.FP(F)F.Cl JPAQBDOJXCMDRF-UHFFFAOYSA-N 0.000 description 2
- VFMMLJPSCATPRE-UHFFFAOYSA-N OP(O)=O.OS(O)(=O)=O.FP(F)F Chemical compound OP(O)=O.OS(O)(=O)=O.FP(F)F VFMMLJPSCATPRE-UHFFFAOYSA-N 0.000 description 2
- WXLUKXGOAUNHRS-UHFFFAOYSA-N P(O)(O)=O.C(=O)[O-].C(C)[PH+](CC)CC Chemical compound P(O)(O)=O.C(=O)[O-].C(C)[PH+](CC)CC WXLUKXGOAUNHRS-UHFFFAOYSA-N 0.000 description 2
- CTQOOYVYXFWCQT-UHFFFAOYSA-N P(O)(O)=O.C(=O)[O-].C(CC)[PH+](CCC)CCC Chemical compound P(O)(O)=O.C(=O)[O-].C(CC)[PH+](CCC)CCC CTQOOYVYXFWCQT-UHFFFAOYSA-N 0.000 description 2
- APFJSSMLONPYBP-UHFFFAOYSA-N P(O)(O)=O.C(=O)[O-].C1(=CC=CC=C1)[PH+](C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound P(O)(O)=O.C(=O)[O-].C1(=CC=CC=C1)[PH+](C1=CC=CC=C1)C1=CC=CC=C1 APFJSSMLONPYBP-UHFFFAOYSA-N 0.000 description 2
- WJQPXDLSUMSKDU-UHFFFAOYSA-N P(O)(O)=O.C(=O)[O-].C[PH+](C)C Chemical compound P(O)(O)=O.C(=O)[O-].C[PH+](C)C WJQPXDLSUMSKDU-UHFFFAOYSA-N 0.000 description 2
- BGJWQAWPQGGKGW-UHFFFAOYSA-N P(O)(O)=O.C(=O)[O-].[NH+]1=CC=CC=C1 Chemical compound P(O)(O)=O.C(=O)[O-].[NH+]1=CC=CC=C1 BGJWQAWPQGGKGW-UHFFFAOYSA-N 0.000 description 2
- IHGVTRSLBIVWQS-UHFFFAOYSA-N P(O)(O)=O.C(=O)[O-].[NH+]1=CC=NC=C1 Chemical compound P(O)(O)=O.C(=O)[O-].[NH+]1=CC=NC=C1 IHGVTRSLBIVWQS-UHFFFAOYSA-N 0.000 description 2
- OSGJBQZBQRYDAC-UHFFFAOYSA-N P(O)(O)=O.C(=O)[O-].[NH+]1=CN=CC=C1 Chemical compound P(O)(O)=O.C(=O)[O-].[NH+]1=CN=CC=C1 OSGJBQZBQRYDAC-UHFFFAOYSA-N 0.000 description 2
- KDHOTBUUASRRDC-UHFFFAOYSA-N P(O)(O)=O.C(=O)[O-].[NH2+]1C=CC=C1 Chemical compound P(O)(O)=O.C(=O)[O-].[NH2+]1C=CC=C1 KDHOTBUUASRRDC-UHFFFAOYSA-N 0.000 description 2
- DXKOFGCUBOIULR-UHFFFAOYSA-N P(O)(O)=O.C(=O)[O-].[NH2+]1CCCCC1 Chemical compound P(O)(O)=O.C(=O)[O-].[NH2+]1CCCCC1 DXKOFGCUBOIULR-UHFFFAOYSA-N 0.000 description 2
- KBSHQGDBRSXHJW-UHFFFAOYSA-N P(O)(O)=O.C(=O)[O-].[NH2+]1CCOCC1 Chemical compound P(O)(O)=O.C(=O)[O-].[NH2+]1CCOCC1 KBSHQGDBRSXHJW-UHFFFAOYSA-N 0.000 description 2
- XFPBNNHSUBDQTH-UHFFFAOYSA-N P(O)(O)=O.C(=O)[O-].[NH2+]1N=CC=C1 Chemical compound P(O)(O)=O.C(=O)[O-].[NH2+]1N=CC=C1 XFPBNNHSUBDQTH-UHFFFAOYSA-N 0.000 description 2
- NISRCYJHMOTDSM-UHFFFAOYSA-N P(O)(O)=O.C(C)(=O)[O-].C(C)[PH+](CC)CC Chemical compound P(O)(O)=O.C(C)(=O)[O-].C(C)[PH+](CC)CC NISRCYJHMOTDSM-UHFFFAOYSA-N 0.000 description 2
- WWXSIOVUBQGTNG-UHFFFAOYSA-N P(O)(O)=O.C(C)(=O)[O-].C(CC)[PH+](CCC)CCC Chemical compound P(O)(O)=O.C(C)(=O)[O-].C(CC)[PH+](CCC)CCC WWXSIOVUBQGTNG-UHFFFAOYSA-N 0.000 description 2
- VLORDZZZDPTJBG-UHFFFAOYSA-N P(O)(O)=O.C(C)(=O)[O-].C(CCC)[PH+](CCCC)CCCC Chemical compound P(O)(O)=O.C(C)(=O)[O-].C(CCC)[PH+](CCCC)CCCC VLORDZZZDPTJBG-UHFFFAOYSA-N 0.000 description 2
- PEHUKMVNCLNKLC-UHFFFAOYSA-N P(O)(O)=O.C(C)(=O)[O-].C1(=CC=CC=C1)[PH+](C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound P(O)(O)=O.C(C)(=O)[O-].C1(=CC=CC=C1)[PH+](C1=CC=CC=C1)C1=CC=CC=C1 PEHUKMVNCLNKLC-UHFFFAOYSA-N 0.000 description 2
- FKWCBIFRNKJAKA-UHFFFAOYSA-N P(O)(O)=O.C(C)(=O)[O-].C[PH+](C)C Chemical compound P(O)(O)=O.C(C)(=O)[O-].C[PH+](C)C FKWCBIFRNKJAKA-UHFFFAOYSA-N 0.000 description 2
- OYJMLIJZTPBUFB-UHFFFAOYSA-N P(O)(O)=O.C(C)(=O)[O-].O1C=[NH+]C=C1 Chemical compound P(O)(O)=O.C(C)(=O)[O-].O1C=[NH+]C=C1 OYJMLIJZTPBUFB-UHFFFAOYSA-N 0.000 description 2
- OJCJRLCIQDBASE-UHFFFAOYSA-N P(O)(O)=O.C(C)(=O)[O-].[NH+]1=CC=CC=C1 Chemical compound P(O)(O)=O.C(C)(=O)[O-].[NH+]1=CC=CC=C1 OJCJRLCIQDBASE-UHFFFAOYSA-N 0.000 description 2
- ZOJBZHPORYPIMY-UHFFFAOYSA-N P(O)(O)=O.C(C)(=O)[O-].[NH+]1=CC=NC=C1 Chemical compound P(O)(O)=O.C(C)(=O)[O-].[NH+]1=CC=NC=C1 ZOJBZHPORYPIMY-UHFFFAOYSA-N 0.000 description 2
- RBVFCCAESKROJG-UHFFFAOYSA-N P(O)(O)=O.C(C)(=O)[O-].[NH2+]1C=CC=C1 Chemical compound P(O)(O)=O.C(C)(=O)[O-].[NH2+]1C=CC=C1 RBVFCCAESKROJG-UHFFFAOYSA-N 0.000 description 2
- PJYFLTDHNLEGKW-UHFFFAOYSA-N P(O)(O)=O.C(C)(=O)[O-].[NH2+]1CCCCC1 Chemical compound P(O)(O)=O.C(C)(=O)[O-].[NH2+]1CCCCC1 PJYFLTDHNLEGKW-UHFFFAOYSA-N 0.000 description 2
- PEYJXYPXWNXPCO-UHFFFAOYSA-N P(O)(O)=O.C(C)(=O)[O-].[NH2+]1CCOCC1 Chemical compound P(O)(O)=O.C(C)(=O)[O-].[NH2+]1CCOCC1 PEYJXYPXWNXPCO-UHFFFAOYSA-N 0.000 description 2
- VLSLYZQSLGWUAM-UHFFFAOYSA-N P(O)(O)=O.C(C)(=O)[O-].[NH2+]1N=CC=C1 Chemical compound P(O)(O)=O.C(C)(=O)[O-].[NH2+]1N=CC=C1 VLSLYZQSLGWUAM-UHFFFAOYSA-N 0.000 description 2
- YJHGCNULVZXVMS-UHFFFAOYSA-N P(O)(O)=O.S([O-])(O)(=O)=O.C(CCC)[PH+](CCCC)CCCC Chemical compound P(O)(O)=O.S([O-])(O)(=O)=O.C(CCC)[PH+](CCCC)CCCC YJHGCNULVZXVMS-UHFFFAOYSA-N 0.000 description 2
- KAKUFLTVIIRTFS-UHFFFAOYSA-N P(O)(O)=O.S([O-])(O)(=O)=O.C1(=CC=CC=C1)[PH+](C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound P(O)(O)=O.S([O-])(O)(=O)=O.C1(=CC=CC=C1)[PH+](C1=CC=CC=C1)C1=CC=CC=C1 KAKUFLTVIIRTFS-UHFFFAOYSA-N 0.000 description 2
- YMGLPSZRGOLXHX-UHFFFAOYSA-N P(O)(O)=O.S([O-])(O)(=O)=O.C[PH+](C)C Chemical compound P(O)(O)=O.S([O-])(O)(=O)=O.C[PH+](C)C YMGLPSZRGOLXHX-UHFFFAOYSA-N 0.000 description 2
- GHNUDKNVHQOBFY-UHFFFAOYSA-N P(O)(O)=O.S([O-])(O)(=O)=O.O1C=[NH+]C=C1 Chemical compound P(O)(O)=O.S([O-])(O)(=O)=O.O1C=[NH+]C=C1 GHNUDKNVHQOBFY-UHFFFAOYSA-N 0.000 description 2
- UWIWWLGKRJTQES-UHFFFAOYSA-N P(O)(O)=O.S([O-])(O)(=O)=O.[NH+]1=CC=NC=C1 Chemical compound P(O)(O)=O.S([O-])(O)(=O)=O.[NH+]1=CC=NC=C1 UWIWWLGKRJTQES-UHFFFAOYSA-N 0.000 description 2
- MEHDKZPUAWTTJI-UHFFFAOYSA-N P(O)(O)=O.S([O-])(O)(=O)=O.[NH+]1=CN=CC=C1 Chemical compound P(O)(O)=O.S([O-])(O)(=O)=O.[NH+]1=CN=CC=C1 MEHDKZPUAWTTJI-UHFFFAOYSA-N 0.000 description 2
- DYTSEPIQLQZOSX-UHFFFAOYSA-N P(O)(O)=O.S([O-])(O)(=O)=O.[NH2+]1C=CC=C1 Chemical compound P(O)(O)=O.S([O-])(O)(=O)=O.[NH2+]1C=CC=C1 DYTSEPIQLQZOSX-UHFFFAOYSA-N 0.000 description 2
- FFEXEEDRBKOZNV-UHFFFAOYSA-N P(O)(O)=O.S([O-])(O)(=O)=O.[NH2+]1C=NC=C1 Chemical compound P(O)(O)=O.S([O-])(O)(=O)=O.[NH2+]1C=NC=C1 FFEXEEDRBKOZNV-UHFFFAOYSA-N 0.000 description 2
- GVRYSDKKAPZVLT-UHFFFAOYSA-N P(O)(O)=O.S([O-])(O)(=O)=O.[NH2+]1CCCCC1 Chemical compound P(O)(O)=O.S([O-])(O)(=O)=O.[NH2+]1CCCCC1 GVRYSDKKAPZVLT-UHFFFAOYSA-N 0.000 description 2
- BWPFWKBXBJANFB-UHFFFAOYSA-N P(O)(O)=O.S([O-])(O)(=O)=O.[NH2+]1CCOCC1 Chemical compound P(O)(O)=O.S([O-])(O)(=O)=O.[NH2+]1CCOCC1 BWPFWKBXBJANFB-UHFFFAOYSA-N 0.000 description 2
- ZHBJXPFTMSELMQ-UHFFFAOYSA-N P(O)(O)=O.S([O-])(O)(=O)=O.[NH2+]1N=CC=C1 Chemical compound P(O)(O)=O.S([O-])(O)(=O)=O.[NH2+]1N=CC=C1 ZHBJXPFTMSELMQ-UHFFFAOYSA-N 0.000 description 2
- FOTIAQAXDQHWMT-UHFFFAOYSA-N P(O)(O)=O.[Br-].C(C)[PH+](CC)CC Chemical compound P(O)(O)=O.[Br-].C(C)[PH+](CC)CC FOTIAQAXDQHWMT-UHFFFAOYSA-N 0.000 description 2
- GEEUIRJYJOMOCQ-UHFFFAOYSA-N P(O)(O)=O.[Br-].C(CC)[PH+](CCC)CCC Chemical compound P(O)(O)=O.[Br-].C(CC)[PH+](CCC)CCC GEEUIRJYJOMOCQ-UHFFFAOYSA-N 0.000 description 2
- GHTZNEDJFDXMHP-UHFFFAOYSA-N P(O)(O)=O.[Br-].C(CCC)[PH+](CCCC)CCCC Chemical compound P(O)(O)=O.[Br-].C(CCC)[PH+](CCCC)CCCC GHTZNEDJFDXMHP-UHFFFAOYSA-N 0.000 description 2
- TYWCHXFNAMLGGW-UHFFFAOYSA-N P(O)(O)=O.[Br-].C1(=CC=CC=C1)[PH+](C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound P(O)(O)=O.[Br-].C1(=CC=CC=C1)[PH+](C1=CC=CC=C1)C1=CC=CC=C1 TYWCHXFNAMLGGW-UHFFFAOYSA-N 0.000 description 2
- KSYFCXJPLLGOBW-UHFFFAOYSA-N P(O)(O)=O.[Br-].C[PH+](C)C Chemical compound P(O)(O)=O.[Br-].C[PH+](C)C KSYFCXJPLLGOBW-UHFFFAOYSA-N 0.000 description 2
- GPJKGESVQXXVLJ-UHFFFAOYSA-N P(O)(O)=O.[Br-].O1C=[NH+]C=C1 Chemical compound P(O)(O)=O.[Br-].O1C=[NH+]C=C1 GPJKGESVQXXVLJ-UHFFFAOYSA-N 0.000 description 2
- SGDDQOUURAJPTM-UHFFFAOYSA-N P(O)(O)=O.[Br-].[NH+]1=CC=CC=C1 Chemical compound P(O)(O)=O.[Br-].[NH+]1=CC=CC=C1 SGDDQOUURAJPTM-UHFFFAOYSA-N 0.000 description 2
- JMAVPDOTVKBPBP-UHFFFAOYSA-N P(O)(O)=O.[Br-].[NH+]1=CC=NC=C1 Chemical compound P(O)(O)=O.[Br-].[NH+]1=CC=NC=C1 JMAVPDOTVKBPBP-UHFFFAOYSA-N 0.000 description 2
- OFADAINBKBQNJA-UHFFFAOYSA-N P(O)(O)=O.[Br-].[NH2+]1C=CC=C1 Chemical compound P(O)(O)=O.[Br-].[NH2+]1C=CC=C1 OFADAINBKBQNJA-UHFFFAOYSA-N 0.000 description 2
- XLDPXPLIIJHHNV-UHFFFAOYSA-N P(O)(O)=O.[Br-].[NH2+]1C=NC=C1 Chemical compound P(O)(O)=O.[Br-].[NH2+]1C=NC=C1 XLDPXPLIIJHHNV-UHFFFAOYSA-N 0.000 description 2
- GITSKEDWLCKCBS-UHFFFAOYSA-N P(O)(O)=O.[Br-].[NH2+]1CCOCC1 Chemical compound P(O)(O)=O.[Br-].[NH2+]1CCOCC1 GITSKEDWLCKCBS-UHFFFAOYSA-N 0.000 description 2
- HWBMBKSDVVXQAP-UHFFFAOYSA-N P(O)(O)=O.[Br-].[NH2+]1N=CC=C1 Chemical compound P(O)(O)=O.[Br-].[NH2+]1N=CC=C1 HWBMBKSDVVXQAP-UHFFFAOYSA-N 0.000 description 2
- KOQKCMLVEPJDSA-UHFFFAOYSA-N P(O)(O)=O.[Cl-].C(C)[PH+](CC)CC Chemical compound P(O)(O)=O.[Cl-].C(C)[PH+](CC)CC KOQKCMLVEPJDSA-UHFFFAOYSA-N 0.000 description 2
- ZWIMAQVQQDGIBG-UHFFFAOYSA-N P(O)(O)=O.[Cl-].C(CC)[PH+](CCC)CCC Chemical compound P(O)(O)=O.[Cl-].C(CC)[PH+](CCC)CCC ZWIMAQVQQDGIBG-UHFFFAOYSA-N 0.000 description 2
- ZJILHJKBRCTUEU-UHFFFAOYSA-N P(O)(O)=O.[Cl-].C(CCC)[PH+](CCCC)CCCC Chemical compound P(O)(O)=O.[Cl-].C(CCC)[PH+](CCCC)CCCC ZJILHJKBRCTUEU-UHFFFAOYSA-N 0.000 description 2
- QGNXOKBNYJSTNQ-UHFFFAOYSA-N P(O)(O)=O.[Cl-].C1(=CC=CC=C1)[PH+](C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound P(O)(O)=O.[Cl-].C1(=CC=CC=C1)[PH+](C1=CC=CC=C1)C1=CC=CC=C1 QGNXOKBNYJSTNQ-UHFFFAOYSA-N 0.000 description 2
- KAZFFAVVVNISML-UHFFFAOYSA-N P(O)(O)=O.[Cl-].C[PH+](C)C Chemical compound P(O)(O)=O.[Cl-].C[PH+](C)C KAZFFAVVVNISML-UHFFFAOYSA-N 0.000 description 2
- ARTCSXGROPSDFG-UHFFFAOYSA-N P(O)(O)=O.[Cl-].O1C=[NH+]C=C1 Chemical compound P(O)(O)=O.[Cl-].O1C=[NH+]C=C1 ARTCSXGROPSDFG-UHFFFAOYSA-N 0.000 description 2
- LKONHSOPBBGJGT-UHFFFAOYSA-N P(O)(O)=O.[Cl-].[NH+]1=CC=CC=C1 Chemical compound P(O)(O)=O.[Cl-].[NH+]1=CC=CC=C1 LKONHSOPBBGJGT-UHFFFAOYSA-N 0.000 description 2
- KWPNKJNMRVWXAS-UHFFFAOYSA-N P(O)(O)=O.[Cl-].[NH+]1=CC=NC=C1 Chemical compound P(O)(O)=O.[Cl-].[NH+]1=CC=NC=C1 KWPNKJNMRVWXAS-UHFFFAOYSA-N 0.000 description 2
- XTIVYCZPBBFVBF-UHFFFAOYSA-N P(O)(O)=O.[Cl-].[NH+]1=CN=CC=C1 Chemical compound P(O)(O)=O.[Cl-].[NH+]1=CN=CC=C1 XTIVYCZPBBFVBF-UHFFFAOYSA-N 0.000 description 2
- OWAFCDXBTXKYBP-UHFFFAOYSA-N P(O)(O)=O.[Cl-].[NH2+]1C=CC=C1 Chemical compound P(O)(O)=O.[Cl-].[NH2+]1C=CC=C1 OWAFCDXBTXKYBP-UHFFFAOYSA-N 0.000 description 2
- PCUPYNIYTUXSDN-UHFFFAOYSA-N P(O)(O)=O.[Cl-].[NH2+]1C=NC=C1 Chemical compound P(O)(O)=O.[Cl-].[NH2+]1C=NC=C1 PCUPYNIYTUXSDN-UHFFFAOYSA-N 0.000 description 2
- WWHDBDGILBIABS-UHFFFAOYSA-N P(O)(O)=O.[Cl-].[NH2+]1CCCCC1 Chemical compound P(O)(O)=O.[Cl-].[NH2+]1CCCCC1 WWHDBDGILBIABS-UHFFFAOYSA-N 0.000 description 2
- WVBJCDMWBKMKPU-UHFFFAOYSA-N P(O)(O)=O.[Cl-].[NH2+]1CCOCC1 Chemical compound P(O)(O)=O.[Cl-].[NH2+]1CCOCC1 WVBJCDMWBKMKPU-UHFFFAOYSA-N 0.000 description 2
- WFMLNEZKNGJQDK-UHFFFAOYSA-N P(O)(O)=O.[Cl-].[NH2+]1N=CC=C1 Chemical compound P(O)(O)=O.[Cl-].[NH2+]1N=CC=C1 WFMLNEZKNGJQDK-UHFFFAOYSA-N 0.000 description 2
- 229910018830 PO3H Inorganic materials 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 229920001131 Pulp (paper) Polymers 0.000 description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
- XNQGKXPBQDTBMZ-UHFFFAOYSA-N S(=O)(=O)(O)[O-].C(C)[PH+](CC)CC Chemical compound S(=O)(=O)(O)[O-].C(C)[PH+](CC)CC XNQGKXPBQDTBMZ-UHFFFAOYSA-N 0.000 description 2
- YWGRIAALSHBQHE-UHFFFAOYSA-N S(O)(O)(=O)=O.FP(F)F Chemical compound S(O)(O)(=O)=O.FP(F)F YWGRIAALSHBQHE-UHFFFAOYSA-N 0.000 description 2
- JIQOYPAIUXMTTC-UHFFFAOYSA-N S([O-])(O)(=O)=O.C(CC)[PH+](CCC)CCC Chemical compound S([O-])(O)(=O)=O.C(CC)[PH+](CCC)CCC JIQOYPAIUXMTTC-UHFFFAOYSA-N 0.000 description 2
- 229910006069 SO3H Inorganic materials 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 241000282898 Sus scrofa Species 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 239000000205 acacia gum Substances 0.000 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
- ITEPDODPZUQDIJ-UHFFFAOYSA-N acetic acid;1,3-oxazole Chemical compound CC([O-])=O.C1=COC=[NH+]1 ITEPDODPZUQDIJ-UHFFFAOYSA-N 0.000 description 2
- MDXDLWCTQWPZLI-UHFFFAOYSA-N acetic acid;1h-pyrazole Chemical compound CC(O)=O.C=1C=NNC=1 MDXDLWCTQWPZLI-UHFFFAOYSA-N 0.000 description 2
- YVDWMBAZNAOWHG-UHFFFAOYSA-N acetic acid;1h-pyrrole Chemical compound CC(O)=O.C=1C=CNC=1 YVDWMBAZNAOWHG-UHFFFAOYSA-N 0.000 description 2
- MIJRUQYZDSEMBD-UHFFFAOYSA-N acetic acid;morpholine Chemical compound CC(O)=O.C1COCCN1 MIJRUQYZDSEMBD-UHFFFAOYSA-N 0.000 description 2
- LKWQRFNQTSFWHS-UHFFFAOYSA-N acetic acid;pyrazine Chemical compound CC(O)=O.C1=CN=CC=N1 LKWQRFNQTSFWHS-UHFFFAOYSA-N 0.000 description 2
- MGZDDCVCLLEWOR-UHFFFAOYSA-N acetic acid;tributylphosphane Chemical compound CC(O)=O.CCCCP(CCCC)CCCC MGZDDCVCLLEWOR-UHFFFAOYSA-N 0.000 description 2
- YAXGXEOYWAIEER-UHFFFAOYSA-N acetic acid;triethylphosphane Chemical compound CC([O-])=O.CC[PH+](CC)CC YAXGXEOYWAIEER-UHFFFAOYSA-N 0.000 description 2
- DUVKXNKIYKAUPK-UHFFFAOYSA-N acetic acid;triphenylphosphane Chemical compound CC(O)=O.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 DUVKXNKIYKAUPK-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 125000005741 alkyl alkenyl group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 239000003957 anion exchange resin Substances 0.000 description 2
- 239000011260 aqueous acid Substances 0.000 description 2
- 239000010426 asphalt Substances 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 238000005102 attenuated total reflection Methods 0.000 description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 2
- 229940092714 benzenesulfonic acid Drugs 0.000 description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- SQVRNKJHWKZAKO-UHFFFAOYSA-N beta-N-Acetyl-D-neuraminic acid Natural products CC(=O)NC1C(O)CC(O)(C(O)=O)OC1C(O)C(O)CO SQVRNKJHWKZAKO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- ZRTSLXKVIFNEQO-UHFFFAOYSA-N bromo(tributyl)phosphanium Chemical compound CCCC[P+](Br)(CCCC)CCCC ZRTSLXKVIFNEQO-UHFFFAOYSA-N 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 150000001805 chlorine compounds Chemical group 0.000 description 2
- 229960004106 citric acid Drugs 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 239000007771 core particle Substances 0.000 description 2
- 229920006037 cross link polymer Polymers 0.000 description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- 125000005508 decahydronaphthalenyl group Chemical group 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 235000005911 diet Nutrition 0.000 description 2
- 230000037213 diet Effects 0.000 description 2
- 230000029087 digestion Effects 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 230000005672 electromagnetic field Effects 0.000 description 2
- 238000001952 enzyme assay Methods 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- PQWGEGZUHVGSKG-UHFFFAOYSA-N formic acid;1,3-oxazole Chemical compound OC=O.C1=COC=N1 PQWGEGZUHVGSKG-UHFFFAOYSA-N 0.000 description 2
- BJFIGCBESRQZMQ-UHFFFAOYSA-N formic acid;1h-imidazole Chemical compound OC=O.C1=CNC=N1 BJFIGCBESRQZMQ-UHFFFAOYSA-N 0.000 description 2
- PXSMDJNMRVUHEM-UHFFFAOYSA-N formic acid;1h-pyrrole Chemical compound OC=O.C=1C=CNC=1 PXSMDJNMRVUHEM-UHFFFAOYSA-N 0.000 description 2
- BDHPJXPOQGPUNI-UHFFFAOYSA-N formic acid;morpholine Chemical compound [O-]C=O.C1COCC[NH2+]1 BDHPJXPOQGPUNI-UHFFFAOYSA-N 0.000 description 2
- KNPWRSVXYPZCOS-UHFFFAOYSA-N formic acid;piperidine Chemical compound [O-]C=O.C1CC[NH2+]CC1 KNPWRSVXYPZCOS-UHFFFAOYSA-N 0.000 description 2
- NHXLWAPIFFWMRV-UHFFFAOYSA-N formic acid;pyrazine Chemical compound OC=O.C1=CN=CC=N1 NHXLWAPIFFWMRV-UHFFFAOYSA-N 0.000 description 2
- FDTUVFSBEYKVAP-UHFFFAOYSA-N formic acid;pyridine Chemical compound OC=O.C1=CC=NC=C1 FDTUVFSBEYKVAP-UHFFFAOYSA-N 0.000 description 2
- FGHVAWYQLUNBDP-UHFFFAOYSA-N formic acid;pyrimidine Chemical compound OC=O.C1=CN=CN=C1 FGHVAWYQLUNBDP-UHFFFAOYSA-N 0.000 description 2
- JXARDJDMVGLGSD-UHFFFAOYSA-N formic acid;triphenylphosphane Chemical compound [O-]C=O.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 JXARDJDMVGLGSD-UHFFFAOYSA-N 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 239000000174 gluconic acid Substances 0.000 description 2
- 235000012208 gluconic acid Nutrition 0.000 description 2
- 239000000665 guar gum Substances 0.000 description 2
- 235000010417 guar gum Nutrition 0.000 description 2
- 229960002154 guar gum Drugs 0.000 description 2
- 125000000262 haloalkenyl group Chemical group 0.000 description 2
- 125000000232 haloalkynyl group Chemical group 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- GEMITLJMEMBDKW-UHFFFAOYSA-N hydrogen sulfate;1h-imidazol-3-ium Chemical compound C1=CNC=N1.OS(O)(=O)=O GEMITLJMEMBDKW-UHFFFAOYSA-N 0.000 description 2
- ZNTBVZRXCXYINT-UHFFFAOYSA-N hydrogen sulfate;1h-pyrazol-1-ium Chemical compound C=1C=NNC=1.OS(O)(=O)=O ZNTBVZRXCXYINT-UHFFFAOYSA-N 0.000 description 2
- PPBUVEINUDWTCG-UHFFFAOYSA-N hydrogen sulfate;pyrazin-1-ium Chemical compound OS(O)(=O)=O.C1=CN=CC=N1 PPBUVEINUDWTCG-UHFFFAOYSA-N 0.000 description 2
- SPHAPKFKSPSKKN-UHFFFAOYSA-N hydrogen sulfate;pyrimidin-1-ium Chemical compound OS(O)(=O)=O.C1=CN=CN=C1 SPHAPKFKSPSKKN-UHFFFAOYSA-N 0.000 description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-O hydron;1,3-oxazole Chemical compound C1=COC=[NH+]1 ZCQWOFVYLHDMMC-UHFFFAOYSA-O 0.000 description 2
- JXYZHMPRERWTPM-UHFFFAOYSA-N hydron;morpholine;chloride Chemical compound Cl.C1COCCN1 JXYZHMPRERWTPM-UHFFFAOYSA-N 0.000 description 2
- CDIDCIDDYQNFDJ-UHFFFAOYSA-N hydron;piperidin-1-ium;sulfate Chemical compound OS(O)(=O)=O.C1CCNCC1 CDIDCIDDYQNFDJ-UHFFFAOYSA-N 0.000 description 2
- VEIWYFRREFUNRC-UHFFFAOYSA-N hydron;piperidine;chloride Chemical compound [Cl-].C1CC[NH2+]CC1 VEIWYFRREFUNRC-UHFFFAOYSA-N 0.000 description 2
- RJGBSYZFOCAGQY-UHFFFAOYSA-N hydroxymethylfurfural Natural products COC1=CC=C(C=O)O1 RJGBSYZFOCAGQY-UHFFFAOYSA-N 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 125000002346 iodo group Chemical group I* 0.000 description 2
- 238000005342 ion exchange Methods 0.000 description 2
- 229920000554 ionomer Polymers 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- CYPPCCJJKNISFK-UHFFFAOYSA-J kaolinite Chemical compound [OH-].[OH-].[OH-].[OH-].[Al+3].[Al+3].[O-][Si](=O)O[Si]([O-])=O CYPPCCJJKNISFK-UHFFFAOYSA-J 0.000 description 2
- 229910052622 kaolinite Inorganic materials 0.000 description 2
- 230000000670 limiting effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 229910052680 mordenite Inorganic materials 0.000 description 2
- BVJOXYJFOYNQRB-UHFFFAOYSA-N morpholine;hydrobromide Chemical compound Br.C1COCCN1 BVJOXYJFOYNQRB-UHFFFAOYSA-N 0.000 description 2
- BGEHHDVYQRNMJB-UHFFFAOYSA-N morpholine;sulfuric acid Chemical compound OS([O-])(=O)=O.C1COCC[NH2+]1 BGEHHDVYQRNMJB-UHFFFAOYSA-N 0.000 description 2
- 125000004370 n-butenyl group Chemical group [H]\C([H])=C(/[H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 230000035764 nutrition Effects 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- ZIRHAFGGEBQZKX-UHFFFAOYSA-N pentyl hydrogen sulfate Chemical compound CCCCCOS(O)(=O)=O ZIRHAFGGEBQZKX-UHFFFAOYSA-N 0.000 description 2
- 125000005981 pentynyl group Chemical group 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 2
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
- FRXLZEVXYFDHIM-UHFFFAOYSA-N phosphanium;hydrogen sulfate Chemical compound [PH4+].OS([O-])(=O)=O FRXLZEVXYFDHIM-UHFFFAOYSA-N 0.000 description 2
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 2
- 150000004714 phosphonium salts Chemical class 0.000 description 2
- WKFBZNUBXWCCHG-UHFFFAOYSA-N phosphorus trifluoride Chemical compound FP(F)F WKFBZNUBXWCCHG-UHFFFAOYSA-N 0.000 description 2
- RAIYODFGMLZUDF-UHFFFAOYSA-N piperidin-1-ium;acetate Chemical compound CC([O-])=O.C1CC[NH2+]CC1 RAIYODFGMLZUDF-UHFFFAOYSA-N 0.000 description 2
- ROFVJSWBDQUQGW-UHFFFAOYSA-N piperidin-1-ium;bromide Chemical compound Br.C1CCNCC1 ROFVJSWBDQUQGW-UHFFFAOYSA-N 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920001281 polyalkylene Polymers 0.000 description 2
- 229920001707 polybutylene terephthalate Polymers 0.000 description 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 2
- 239000004810 polytetrafluoroethylene Substances 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 108090000765 processed proteins & peptides Proteins 0.000 description 2
- 125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 239000008262 pumice Substances 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- HYHBKLWDTGTBME-UHFFFAOYSA-N pyrazin-1-ium;chloride Chemical compound Cl.C1=CN=CC=N1 HYHBKLWDTGTBME-UHFFFAOYSA-N 0.000 description 2
- KNBMYMNEEGYSMP-UHFFFAOYSA-N pyrazine;hydrobromide Chemical compound [Br-].C1=C[NH+]=CC=N1 KNBMYMNEEGYSMP-UHFFFAOYSA-N 0.000 description 2
- GAPYKZAARZMMGP-UHFFFAOYSA-N pyridin-1-ium;acetate Chemical compound CC(O)=O.C1=CC=NC=C1 GAPYKZAARZMMGP-UHFFFAOYSA-N 0.000 description 2
- BBFCIBZLAVOLCF-UHFFFAOYSA-N pyridin-1-ium;bromide Chemical compound Br.C1=CC=NC=C1 BBFCIBZLAVOLCF-UHFFFAOYSA-N 0.000 description 2
- ZNCXUFVDFVBRDO-UHFFFAOYSA-N pyridine;sulfuric acid Chemical compound [H+].[O-]S([O-])(=O)=O.C1=CC=[NH+]C=C1 ZNCXUFVDFVBRDO-UHFFFAOYSA-N 0.000 description 2
- WRMCZHYLTVSDQU-UHFFFAOYSA-N pyrimidin-1-ium;acetate Chemical compound CC(O)=O.C1=CN=CN=C1 WRMCZHYLTVSDQU-UHFFFAOYSA-N 0.000 description 2
- BATMYWDOUUWCJE-UHFFFAOYSA-N pyrimidin-1-ium;bromide Chemical compound Br.C1=CN=CN=C1 BATMYWDOUUWCJE-UHFFFAOYSA-N 0.000 description 2
- IDXKTTNFXPPXJY-UHFFFAOYSA-N pyrimidin-1-ium;chloride Chemical compound Cl.C1=CN=CN=C1 IDXKTTNFXPPXJY-UHFFFAOYSA-N 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- 238000002798 spectrophotometry method Methods 0.000 description 2
- 125000003003 spiro group Chemical group 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 125000005717 substituted cycloalkylene group Chemical group 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
- YGNORFLIQAXXCM-UHFFFAOYSA-N sulfuric acid;triphenylphosphane Chemical compound OS([O-])(=O)=O.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 YGNORFLIQAXXCM-UHFFFAOYSA-N 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- MJRPMUINYAOXRW-UHFFFAOYSA-N tributylphosphane;hydrochloride Chemical compound [Cl-].CCCC[PH+](CCCC)CCCC MJRPMUINYAOXRW-UHFFFAOYSA-N 0.000 description 2
- NXPYHCCOHHNZNF-UHFFFAOYSA-N triethylphosphane;hydrochloride Chemical compound [Cl-].CC[PH+](CC)CC NXPYHCCOHHNZNF-UHFFFAOYSA-N 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- ZUBQQDQYKGOZGK-UHFFFAOYSA-N trimethylphosphane;hydrobromide Chemical compound [Br-].C[PH+](C)C ZUBQQDQYKGOZGK-UHFFFAOYSA-N 0.000 description 2
- QMGCGMCWRCSEPP-UHFFFAOYSA-N trimethylphosphane;hydrochloride Chemical compound [Cl-].C[PH+](C)C QMGCGMCWRCSEPP-UHFFFAOYSA-N 0.000 description 2
- JOGPWCNKKYKKAA-UHFFFAOYSA-N trimethylphosphanium;acetate Chemical compound C[PH+](C)C.CC([O-])=O JOGPWCNKKYKKAA-UHFFFAOYSA-N 0.000 description 2
- CMSYDJVRTHCWFP-UHFFFAOYSA-N triphenylphosphane;hydrobromide Chemical compound Br.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 CMSYDJVRTHCWFP-UHFFFAOYSA-N 0.000 description 2
- AVCVDUDESCZFHJ-UHFFFAOYSA-N triphenylphosphane;hydrochloride Chemical compound [Cl-].C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 AVCVDUDESCZFHJ-UHFFFAOYSA-N 0.000 description 2
- XDLFIHUKAYRZAC-UHFFFAOYSA-N tripropylphosphane;hydrobromide Chemical compound [Br-].CCC[PH+](CCC)CCC XDLFIHUKAYRZAC-UHFFFAOYSA-N 0.000 description 2
- YGKJREIBEBNZIZ-UHFFFAOYSA-N tripropylphosphanium;chloride Chemical compound [Cl-].CCC[PH+](CCC)CCC YGKJREIBEBNZIZ-UHFFFAOYSA-N 0.000 description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- 235000020234 walnut Nutrition 0.000 description 2
- 125000005869 (methoxyethoxy)methanyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- 125000005868 (methoxymethoxy)methanyl group Chemical group [H]C([H])([H])OC([H])([H])OC([H])([H])* 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- SEQRDAAUNCRFIT-UHFFFAOYSA-N 1,1-dichlorobutane Chemical compound CCCC(Cl)Cl SEQRDAAUNCRFIT-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- CZWSZZHGSNZRMW-UHFFFAOYSA-N 1,2-dibromobutane Chemical compound CCC(Br)CBr CZWSZZHGSNZRMW-UHFFFAOYSA-N 0.000 description 1
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- CITMYAPULDSOHG-UHFFFAOYSA-N 1,2-dibromopentane Chemical compound CCCC(Br)CBr CITMYAPULDSOHG-UHFFFAOYSA-N 0.000 description 1
- XFNJYAKDBJUJAJ-UHFFFAOYSA-N 1,2-dibromopropane Chemical compound CC(Br)CBr XFNJYAKDBJUJAJ-UHFFFAOYSA-N 0.000 description 1
- PQBOTZNYFQWRHU-UHFFFAOYSA-N 1,2-dichlorobutane Chemical compound CCC(Cl)CCl PQBOTZNYFQWRHU-UHFFFAOYSA-N 0.000 description 1
- PPLBPDUKNRCHGG-UHFFFAOYSA-N 1,2-dichloropentane Chemical compound CCCC(Cl)CCl PPLBPDUKNRCHGG-UHFFFAOYSA-N 0.000 description 1
- MIAAQPQIWLWRSI-UHFFFAOYSA-N 1,2-diiodobutane Chemical compound CCC(I)CI MIAAQPQIWLWRSI-UHFFFAOYSA-N 0.000 description 1
- GBBZLMLLFVFKJM-UHFFFAOYSA-N 1,2-diiodoethane Chemical compound ICCI GBBZLMLLFVFKJM-UHFFFAOYSA-N 0.000 description 1
- RJJBMBXTBVCMND-UHFFFAOYSA-N 1,2-diiodopentane Chemical compound CCCC(I)CI RJJBMBXTBVCMND-UHFFFAOYSA-N 0.000 description 1
- ISXPOEJSKALLKA-UHFFFAOYSA-N 1,2-diiodopropane Chemical compound CC(I)CI ISXPOEJSKALLKA-UHFFFAOYSA-N 0.000 description 1
- XZNGUVQDFJHPLU-UHFFFAOYSA-N 1,3-dibromobutane Chemical compound CC(Br)CCBr XZNGUVQDFJHPLU-UHFFFAOYSA-N 0.000 description 1
- SOZLNIPBRVQUOG-UHFFFAOYSA-N 1,3-dibromopentane Chemical compound CCC(Br)CCBr SOZLNIPBRVQUOG-UHFFFAOYSA-N 0.000 description 1
- VEFLKXRACNJHOV-UHFFFAOYSA-N 1,3-dibromopropane Chemical compound BrCCCBr VEFLKXRACNJHOV-UHFFFAOYSA-N 0.000 description 1
- XFZOUCXVIFNOLX-UHFFFAOYSA-N 1,3-dichlorobutane Chemical compound [CH2]C(Cl)CCCl XFZOUCXVIFNOLX-UHFFFAOYSA-N 0.000 description 1
- QMLLRWZQACTYAX-UHFFFAOYSA-N 1,3-dichloropentane Chemical compound CCC(Cl)CCCl QMLLRWZQACTYAX-UHFFFAOYSA-N 0.000 description 1
- YHRUOJUYPBUZOS-UHFFFAOYSA-N 1,3-dichloropropane Chemical compound ClCCCCl YHRUOJUYPBUZOS-UHFFFAOYSA-N 0.000 description 1
- ZFMSVHPAOMPMMF-UHFFFAOYSA-N 1,3-diiodobutane Chemical compound CC(I)CCI ZFMSVHPAOMPMMF-UHFFFAOYSA-N 0.000 description 1
- GHRIWTBUXMUHJM-UHFFFAOYSA-N 1,3-diiodopentane Chemical compound CCC(I)CCI GHRIWTBUXMUHJM-UHFFFAOYSA-N 0.000 description 1
- JFVQTBCQTKUHQV-UHFFFAOYSA-N 1,3-oxazole;sulfuric acid Chemical compound C1=COC=[NH+]1.OS([O-])(=O)=O JFVQTBCQTKUHQV-UHFFFAOYSA-N 0.000 description 1
- ULTHEAFYOOPTTB-UHFFFAOYSA-N 1,4-dibromobutane Chemical compound BrCCCCBr ULTHEAFYOOPTTB-UHFFFAOYSA-N 0.000 description 1
- CNBFRBXEGGRSPL-UHFFFAOYSA-N 1,4-dibromopentane Chemical compound CC(Br)CCCBr CNBFRBXEGGRSPL-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- KJDRSWPQXHESDQ-UHFFFAOYSA-N 1,4-dichlorobutane Chemical compound ClCCCCCl KJDRSWPQXHESDQ-UHFFFAOYSA-N 0.000 description 1
- IJZUPZAYWWVHIO-UHFFFAOYSA-N 1,4-dichloropentane Chemical compound CC(Cl)CCCCl IJZUPZAYWWVHIO-UHFFFAOYSA-N 0.000 description 1
- ROUYUBHVBIKMQO-UHFFFAOYSA-N 1,4-diiodobutane Chemical compound ICCCCI ROUYUBHVBIKMQO-UHFFFAOYSA-N 0.000 description 1
- CKTWXVLPFHHXEW-UHFFFAOYSA-N 1,4-diiodopentane Chemical compound CC(I)CCCI CKTWXVLPFHHXEW-UHFFFAOYSA-N 0.000 description 1
- IBODDUNKEPPBKW-UHFFFAOYSA-N 1,5-dibromopentane Chemical compound BrCCCCCBr IBODDUNKEPPBKW-UHFFFAOYSA-N 0.000 description 1
- LBKDGROORAKTLC-UHFFFAOYSA-N 1,5-dichloropentane Chemical compound ClCCCCCCl LBKDGROORAKTLC-UHFFFAOYSA-N 0.000 description 1
- IAEOYUUPFYJXHN-UHFFFAOYSA-N 1,5-diiodopentane Chemical compound ICCCCCI IAEOYUUPFYJXHN-UHFFFAOYSA-N 0.000 description 1
- QLOKJRIVRGCVIM-UHFFFAOYSA-N 1-[(4-methylsulfanylphenyl)methyl]piperazine Chemical compound C1=CC(SC)=CC=C1CN1CCNCC1 QLOKJRIVRGCVIM-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- SLBOQBILGNEPEB-UHFFFAOYSA-N 1-chloroprop-2-enylbenzene Chemical compound C=CC(Cl)C1=CC=CC=C1 SLBOQBILGNEPEB-UHFFFAOYSA-N 0.000 description 1
- IWDFHWZHHOSSGR-UHFFFAOYSA-N 1-ethylimidazole Chemical compound CCN1C=CN=C1 IWDFHWZHHOSSGR-UHFFFAOYSA-N 0.000 description 1
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 1
- BETCGUSQXWSOCN-UHFFFAOYSA-N 1-methyl-1h-benzimidazol-1-ium;chloride Chemical group [Cl-].C1=CC=C2[N+](C)=CNC2=C1 BETCGUSQXWSOCN-UHFFFAOYSA-N 0.000 description 1
- FGYADSCZTQOAFK-UHFFFAOYSA-N 1-methylbenzimidazole Chemical compound C1=CC=C2N(C)C=NC2=C1 FGYADSCZTQOAFK-UHFFFAOYSA-N 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- OFGDSGVGRWPQJQ-UHFFFAOYSA-N 1h-imidazol-1-ium;acetate Chemical compound CC(O)=O.C1=CNC=N1 OFGDSGVGRWPQJQ-UHFFFAOYSA-N 0.000 description 1
- RMYXXJKVVYQPLG-UHFFFAOYSA-N 1h-imidazol-1-ium;sulfate Chemical compound [NH2+]1C=CN=C1.[NH2+]1C=CN=C1.[O-]S([O-])(=O)=O RMYXXJKVVYQPLG-UHFFFAOYSA-N 0.000 description 1
- LEJIWJCKYUOQDZ-UHFFFAOYSA-N 1h-pyrrole;hydrobromide Chemical compound Br.C=1C=CNC=1 LEJIWJCKYUOQDZ-UHFFFAOYSA-N 0.000 description 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- SCVJRXQHFJXZFZ-KVQBGUIXSA-N 2-amino-9-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purine-6-thione Chemical compound C1=2NC(N)=NC(=S)C=2N=CN1[C@H]1C[C@H](O)[C@@H](CO)O1 SCVJRXQHFJXZFZ-KVQBGUIXSA-N 0.000 description 1
- IBVSJLVOJTXSHD-UHFFFAOYSA-N 2-butyl-3-ethenyl-1H-imidazol-3-ium chloride Chemical compound [Cl-].C(CCC)C=1[NH+](C=CN1)C=C IBVSJLVOJTXSHD-UHFFFAOYSA-N 0.000 description 1
- YNTFDUSOVMNOTM-UHFFFAOYSA-O 2-butyl-3-ethenyl-1h-imidazol-3-ium Chemical compound CCCCC=1NC=C[N+]=1C=C YNTFDUSOVMNOTM-UHFFFAOYSA-O 0.000 description 1
- VMSBGXAJJLPWKV-UHFFFAOYSA-N 2-ethenylbenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1C=C VMSBGXAJJLPWKV-UHFFFAOYSA-N 0.000 description 1
- JESXATFQYMPTNL-UHFFFAOYSA-N 2-ethenylphenol Chemical class OC1=CC=CC=C1C=C JESXATFQYMPTNL-UHFFFAOYSA-N 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- 125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000005916 2-methylpentyl group Chemical group 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 description 1
- BHZUNHXTRRNKST-UHFFFAOYSA-N 3,3-dimethylpenta-1,4-diene Chemical compound C=CC(C)(C)C=C BHZUNHXTRRNKST-UHFFFAOYSA-N 0.000 description 1
- BKVALJGAKNDDJJ-UHFFFAOYSA-N 3,4-dimethylhexa-1,5-diene Chemical compound C=CC(C)C(C)C=C BKVALJGAKNDDJJ-UHFFFAOYSA-N 0.000 description 1
- XMLSBPQICJMVGR-UHFFFAOYSA-N 3-acetyl-4-methylmorpholin-4-ium-4-sulfonate Chemical compound CC(=O)C1COCC[N+]1(C)S(=O)(=O)[O-] XMLSBPQICJMVGR-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- ABDVJABGTGHCPI-UHFFFAOYSA-N 3-ethyl-1h-imidazol-3-ium;chloride Chemical group Cl.CCN1C=CN=C1 ABDVJABGTGHCPI-UHFFFAOYSA-N 0.000 description 1
- 102100022584 3-keto-steroid reductase/17-beta-hydroxysteroid dehydrogenase 7 Human genes 0.000 description 1
- 101710135980 3-keto-steroid reductase/17-beta-hydroxysteroid dehydrogenase 7 Proteins 0.000 description 1
- 125000003469 3-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- IKQUUYYDRTYXAP-UHFFFAOYSA-N 3-methylpenta-1,4-diene Chemical compound C=CC(C)C=C IKQUUYYDRTYXAP-UHFFFAOYSA-N 0.000 description 1
- 125000005917 3-methylpentyl group Chemical group 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 241000609240 Ambelania acida Species 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical group CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- KVJGKLGXCVAQBG-UHFFFAOYSA-N C(=O)[O-].C(CC)[PH+](CCC)CCC Chemical compound C(=O)[O-].C(CC)[PH+](CCC)CCC KVJGKLGXCVAQBG-UHFFFAOYSA-N 0.000 description 1
- MOQWCNVWJGTDHF-UHFFFAOYSA-N C(C)(=O)O.FP(F)F Chemical compound C(C)(=O)O.FP(F)F MOQWCNVWJGTDHF-UHFFFAOYSA-N 0.000 description 1
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 description 1
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 description 1
- 125000000041 C6-C10 aryl group Chemical group 0.000 description 1
- 101100434846 Caenorhabditis elegans lap-1 gene Proteins 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- 229920002101 Chitin Polymers 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- ZAQJHHRNXZUBTE-WUJLRWPWSA-N D-xylulose Chemical compound OC[C@@H](O)[C@H](O)C(=O)CO ZAQJHHRNXZUBTE-WUJLRWPWSA-N 0.000 description 1
- NKLCNNUWBJBICK-UHFFFAOYSA-N Dess-Martin periodinane Substances C1=CC=C2I(OC(=O)C)(OC(C)=O)(OC(C)=O)OC(=O)C2=C1 NKLCNNUWBJBICK-UHFFFAOYSA-N 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 240000003133 Elaeis guineensis Species 0.000 description 1
- 235000001950 Elaeis guineensis Nutrition 0.000 description 1
- 208000010201 Exanthema Diseases 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- 229920002488 Hemicellulose Polymers 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical class C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229920001202 Inulin Polymers 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical class [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 240000003183 Manihot esculenta Species 0.000 description 1
- 235000016735 Manihot esculenta subsp esculenta Nutrition 0.000 description 1
- 101100216020 Mus musculus Anpep gene Proteins 0.000 description 1
- 101100521055 Mus musculus Prl7d1 gene Proteins 0.000 description 1
- SQVRNKJHWKZAKO-PFQGKNLYSA-N N-acetyl-beta-neuraminic acid Chemical compound CC(=O)N[C@@H]1[C@@H](O)C[C@@](O)(C(O)=O)O[C@H]1[C@H](O)[C@H](O)CO SQVRNKJHWKZAKO-PFQGKNLYSA-N 0.000 description 1
- 125000000815 N-oxide group Chemical group 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- 208000008589 Obesity Diseases 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- WXLWRYVNHGNTTI-UHFFFAOYSA-N P(O)(O)=O.C(=O)[O-].C(CCC)[PH+](CCCC)CCCC Chemical compound P(O)(O)=O.C(=O)[O-].C(CCC)[PH+](CCCC)CCCC WXLWRYVNHGNTTI-UHFFFAOYSA-N 0.000 description 1
- LDLANLPGPUMADO-UHFFFAOYSA-N P(O)(O)=O.C(=O)[O-].O1C=[NH+]C=C1 Chemical compound P(O)(O)=O.C(=O)[O-].O1C=[NH+]C=C1 LDLANLPGPUMADO-UHFFFAOYSA-N 0.000 description 1
- IBJKYZKIUJRBCA-UHFFFAOYSA-N P(O)(O)=O.C(=O)[O-].[NH2+]1C=NC=C1 Chemical compound P(O)(O)=O.C(=O)[O-].[NH2+]1C=NC=C1 IBJKYZKIUJRBCA-UHFFFAOYSA-N 0.000 description 1
- YNSAMXWCKAXEGE-UHFFFAOYSA-N P(O)(O)=O.C(C)(=O)[O-].[NH2+]1C=NC=C1 Chemical compound P(O)(O)=O.C(C)(=O)[O-].[NH2+]1C=NC=C1 YNSAMXWCKAXEGE-UHFFFAOYSA-N 0.000 description 1
- HWVAGMIUBYYEQA-UHFFFAOYSA-N P(O)(O)=O.S([O-])(O)(=O)=O.C(C)[PH+](CC)CC Chemical compound P(O)(O)=O.S([O-])(O)(=O)=O.C(C)[PH+](CC)CC HWVAGMIUBYYEQA-UHFFFAOYSA-N 0.000 description 1
- KKPADWRTMLUSPB-UHFFFAOYSA-N P(O)(O)=O.S([O-])(O)(=O)=O.C(CC)[PH+](CCC)CCC Chemical compound P(O)(O)=O.S([O-])(O)(=O)=O.C(CC)[PH+](CCC)CCC KKPADWRTMLUSPB-UHFFFAOYSA-N 0.000 description 1
- DDIZCBRYGIUKMA-UHFFFAOYSA-N P(O)(O)=O.S([O-])(O)(=O)=O.[NH+]1=CC=CC=C1 Chemical compound P(O)(O)=O.S([O-])(O)(=O)=O.[NH+]1=CC=CC=C1 DDIZCBRYGIUKMA-UHFFFAOYSA-N 0.000 description 1
- ZIEIZZGRJQZSCC-UHFFFAOYSA-N P(O)(O)=O.[Br-].[NH+]1=CN=CC=C1 Chemical compound P(O)(O)=O.[Br-].[NH+]1=CN=CC=C1 ZIEIZZGRJQZSCC-UHFFFAOYSA-N 0.000 description 1
- JNRZXYRADQMFCB-UHFFFAOYSA-N P(O)(O)=O.[Br-].[NH2+]1CCCCC1 Chemical compound P(O)(O)=O.[Br-].[NH2+]1CCCCC1 JNRZXYRADQMFCB-UHFFFAOYSA-N 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000004962 Polyamide-imide Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical group CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- MUPFEKGTMRGPLJ-RMMQSMQOSA-N Raffinose Natural products O(C[C@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O[C@@]2(CO)[C@H](O)[C@@H](O)[C@@H](CO)O2)O1)[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 MUPFEKGTMRGPLJ-RMMQSMQOSA-N 0.000 description 1
- 241000282849 Ruminantia Species 0.000 description 1
- CZPYGLBDOZORFI-UHFFFAOYSA-N S(=O)(=O)(O)[O-].C[PH+](C)C Chemical compound S(=O)(=O)(O)[O-].C[PH+](C)C CZPYGLBDOZORFI-UHFFFAOYSA-N 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 240000000111 Saccharum officinarum Species 0.000 description 1
- 235000007201 Saccharum officinarum Nutrition 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
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical group [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- MUPFEKGTMRGPLJ-UHFFFAOYSA-N UNPD196149 Natural products OC1C(O)C(CO)OC1(CO)OC1C(O)C(O)C(O)C(COC2C(C(O)C(O)C(CO)O2)O)O1 MUPFEKGTMRGPLJ-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- XOCUXOWLYLLJLV-UHFFFAOYSA-N [O].[S] Chemical compound [O].[S] XOCUXOWLYLLJLV-UHFFFAOYSA-N 0.000 description 1
- CDOMXXVCZQOOMT-UHFFFAOYSA-N [phenoxy(phenyl)phosphoryl]oxybenzene Chemical compound C=1C=CC=CC=1OP(C=1C=CC=CC=1)(=O)OC1=CC=CC=C1 CDOMXXVCZQOOMT-UHFFFAOYSA-N 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- MBLBDJOUHNCFQT-LXGUWJNJSA-N aldehydo-N-acetyl-D-glucosamine Chemical compound CC(=O)N[C@@H](C=O)[C@@H](O)[C@H](O)[C@H](O)CO MBLBDJOUHNCFQT-LXGUWJNJSA-N 0.000 description 1
- 125000002820 allylidene group Chemical group [H]C(=[*])C([H])=C([H])[H] 0.000 description 1
- 235000019728 animal nutrition Nutrition 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 238000009360 aquaculture Methods 0.000 description 1
- 244000144974 aquaculture Species 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 239000010905 bagasse Substances 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 235000008429 bread Nutrition 0.000 description 1
- 235000015496 breakfast cereal Nutrition 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 235000012839 cake mixes Nutrition 0.000 description 1
- 229940077731 carbohydrate nutrients Drugs 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 239000003575 carbonaceous material Substances 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000002144 chemical decomposition reaction Methods 0.000 description 1
- 150000005829 chemical entities Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 238000010668 complexation reaction Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 229920001577 copolymer Chemical compound 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000002993 cycloalkylene group Chemical group 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 235000013365 dairy product Nutrition 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 150000008266 deoxy sugars Chemical class 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
- 210000002249 digestive system Anatomy 0.000 description 1
- 125000004982 dihaloalkyl group Chemical group 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000012971 dimethylpiperazine Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 230000007071 enzymatic hydrolysis Effects 0.000 description 1
- 238000006047 enzymatic hydrolysis reaction Methods 0.000 description 1
- 238000011067 equilibration Methods 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 201000005884 exanthem Diseases 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 235000012041 food component Nutrition 0.000 description 1
- 239000005417 food ingredient Substances 0.000 description 1
- GSTNAAOCEHQZDY-UHFFFAOYSA-N formic acid phosphane Chemical compound [PH4+].[O-]C=O GSTNAAOCEHQZDY-UHFFFAOYSA-N 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-L glutamate group Chemical group N[C@@H](CCC(=O)[O-])C(=O)[O-] WHUUTDBJXJRKMK-VKHMYHEASA-L 0.000 description 1
- 125000000291 glutamic acid group Chemical group N[C@@H](CCC(O)=O)C(=O)* 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 238000000892 gravimetry Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 239000011121 hardwood Substances 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 125000006341 heptafluoro n-propyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
- 125000004366 heterocycloalkenyl group Chemical group 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 244000005702 human microbiome Species 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 description 1
- 235000015243 ice cream Nutrition 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 238000009655 industrial fermentation Methods 0.000 description 1
- 238000002065 inelastic X-ray scattering Methods 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- JYJIGFIDKWBXDU-MNNPPOADSA-N inulin Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)OC[C@]1(OC[C@]2(OC[C@]3(OC[C@]4(OC[C@]5(OC[C@]6(OC[C@]7(OC[C@]8(OC[C@]9(OC[C@]%10(OC[C@]%11(OC[C@]%12(OC[C@]%13(OC[C@]%14(OC[C@]%15(OC[C@]%16(OC[C@]%17(OC[C@]%18(OC[C@]%19(OC[C@]%20(OC[C@]%21(OC[C@]%22(OC[C@]%23(OC[C@]%24(OC[C@]%25(OC[C@]%26(OC[C@]%27(OC[C@]%28(OC[C@]%29(OC[C@]%30(OC[C@]%31(OC[C@]%32(OC[C@]%33(OC[C@]%34(OC[C@]%35(OC[C@]%36(O[C@@H]%37[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O%37)O)[C@H]([C@H](O)[C@@H](CO)O%36)O)[C@H]([C@H](O)[C@@H](CO)O%35)O)[C@H]([C@H](O)[C@@H](CO)O%34)O)[C@H]([C@H](O)[C@@H](CO)O%33)O)[C@H]([C@H](O)[C@@H](CO)O%32)O)[C@H]([C@H](O)[C@@H](CO)O%31)O)[C@H]([C@H](O)[C@@H](CO)O%30)O)[C@H]([C@H](O)[C@@H](CO)O%29)O)[C@H]([C@H](O)[C@@H](CO)O%28)O)[C@H]([C@H](O)[C@@H](CO)O%27)O)[C@H]([C@H](O)[C@@H](CO)O%26)O)[C@H]([C@H](O)[C@@H](CO)O%25)O)[C@H]([C@H](O)[C@@H](CO)O%24)O)[C@H]([C@H](O)[C@@H](CO)O%23)O)[C@H]([C@H](O)[C@@H](CO)O%22)O)[C@H]([C@H](O)[C@@H](CO)O%21)O)[C@H]([C@H](O)[C@@H](CO)O%20)O)[C@H]([C@H](O)[C@@H](CO)O%19)O)[C@H]([C@H](O)[C@@H](CO)O%18)O)[C@H]([C@H](O)[C@@H](CO)O%17)O)[C@H]([C@H](O)[C@@H](CO)O%16)O)[C@H]([C@H](O)[C@@H](CO)O%15)O)[C@H]([C@H](O)[C@@H](CO)O%14)O)[C@H]([C@H](O)[C@@H](CO)O%13)O)[C@H]([C@H](O)[C@@H](CO)O%12)O)[C@H]([C@H](O)[C@@H](CO)O%11)O)[C@H]([C@H](O)[C@@H](CO)O%10)O)[C@H]([C@H](O)[C@@H](CO)O9)O)[C@H]([C@H](O)[C@@H](CO)O8)O)[C@H]([C@H](O)[C@@H](CO)O7)O)[C@H]([C@H](O)[C@@H](CO)O6)O)[C@H]([C@H](O)[C@@H](CO)O5)O)[C@H]([C@H](O)[C@@H](CO)O4)O)[C@H]([C@H](O)[C@@H](CO)O3)O)[C@H]([C@H](O)[C@@H](CO)O2)O)[C@@H](O)[C@H](O)[C@@H](CO)O1 JYJIGFIDKWBXDU-MNNPPOADSA-N 0.000 description 1
- 229940029339 inulin Drugs 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- BQINXKOTJQCISL-GRCPKETISA-N keto-neuraminic acid Chemical class OC(=O)C(=O)C[C@H](O)[C@@H](N)[C@@H](O)[C@H](O)[C@H](O)CO BQINXKOTJQCISL-GRCPKETISA-N 0.000 description 1
- 239000003041 laboratory chemical Substances 0.000 description 1
- 239000011777 magnesium Chemical class 0.000 description 1
- 229910052749 magnesium Chemical class 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000013178 mathematical model Methods 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 238000005374 membrane filtration Methods 0.000 description 1
- 125000005866 methoxyethanyl group Chemical group 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- MEFBJEMVZONFCJ-UHFFFAOYSA-N molybdate Chemical compound [O-][Mo]([O-])(=O)=O MEFBJEMVZONFCJ-UHFFFAOYSA-N 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 150000002780 morpholines Chemical class 0.000 description 1
- AFDQGRURHDVABZ-UHFFFAOYSA-N n,n-dimethylformamide;sulfur trioxide Chemical compound O=S(=O)=O.CN(C)C=O AFDQGRURHDVABZ-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002916 oxazoles Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 230000033116 oxidation-reduction process Effects 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- QYZLKGVUSQXAMU-UHFFFAOYSA-N penta-1,4-diene Chemical compound C=CCC=C QYZLKGVUSQXAMU-UHFFFAOYSA-N 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- PMOIAJVKYNVHQE-UHFFFAOYSA-N phosphanium;bromide Chemical compound [PH4+].[Br-] PMOIAJVKYNVHQE-UHFFFAOYSA-N 0.000 description 1
- TWWBIMNLBUYJKB-UHFFFAOYSA-N phosphanyl acetate Chemical compound CC(=O)OP TWWBIMNLBUYJKB-UHFFFAOYSA-N 0.000 description 1
- 239000002367 phosphate rock Substances 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- PLJNHZOEOXGWIR-UHFFFAOYSA-N piroheptine hydrochloride Chemical compound Cl.CC1N(CC)CCC1=C1C2=CC=CC=C2CCC2=CC=CC=C21 PLJNHZOEOXGWIR-UHFFFAOYSA-N 0.000 description 1
- 239000011295 pitch Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 229920000779 poly(divinylbenzene) Polymers 0.000 description 1
- 229920002312 polyamide-imide Polymers 0.000 description 1
- 229920000412 polyarylene Polymers 0.000 description 1
- 229920006260 polyaryletherketone Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- IWZKICVEHNUQTL-UHFFFAOYSA-M potassium hydrogen phthalate Chemical compound [K+].OC(=O)C1=CC=CC=C1C([O-])=O IWZKICVEHNUQTL-UHFFFAOYSA-M 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 238000000634 powder X-ray diffraction Methods 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000003216 pyrazines Chemical class 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- MUPFEKGTMRGPLJ-ZQSKZDJDSA-N raffinose 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[C@@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O2)O)O1 MUPFEKGTMRGPLJ-ZQSKZDJDSA-N 0.000 description 1
- 206010037844 rash Diseases 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000000284 resting effect Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000004626 scanning electron microscopy Methods 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 1
- SQVRNKJHWKZAKO-OQPLDHBCSA-N sialic acid Chemical compound CC(=O)N[C@@H]1[C@@H](O)C[C@@](O)(C(O)=O)OC1[C@H](O)[C@H](O)CO SQVRNKJHWKZAKO-OQPLDHBCSA-N 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 239000011122 softwood Substances 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 229940032147 starch Drugs 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 239000010907 stover Substances 0.000 description 1
- 239000010902 straw Substances 0.000 description 1
- 125000005017 substituted alkenyl group Chemical group 0.000 description 1
- 125000005415 substituted alkoxy group Chemical group 0.000 description 1
- 125000004426 substituted alkynyl group Chemical group 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- XTQHKBHJIVJGKJ-UHFFFAOYSA-N sulfur monoxide Chemical class S=O XTQHKBHJIVJGKJ-UHFFFAOYSA-N 0.000 description 1
- 229910052815 sulfur oxide Inorganic materials 0.000 description 1
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 1
- QDUVKIFOULWJQB-UHFFFAOYSA-N sulfuric acid;tributylphosphane Chemical compound OS(O)(=O)=O.CCCCP(CCCC)CCCC QDUVKIFOULWJQB-UHFFFAOYSA-N 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000011269 tar Substances 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 150000004897 thiazines Chemical class 0.000 description 1
- 150000003557 thiazoles Chemical class 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- PRYDGNPXVINHFJ-UHFFFAOYSA-N triethylphosphane;hydrobromide Chemical compound [Br-].CC[PH+](CC)CC PRYDGNPXVINHFJ-UHFFFAOYSA-N 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 238000012800 visualization Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 235000013618 yogurt Nutrition 0.000 description 1
Classifications
-
- 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
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/006—Heteroglycans, i.e. polysaccharides having more than one sugar residue in the main chain in either alternating or less regular sequence; Gellans; Succinoglycans; Arabinogalactans; Tragacanth or gum tragacanth or traganth from Astragalus; Gum Karaya from Sterculia urens; Gum Ghatti from Anogeissus latifolia; Derivatives thereof
-
- 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
- C07H3/06—Oligosaccharides, i.e. having three to five saccharide radicals attached to each other by glycosidic linkages
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/163—Sugars; Polysaccharides
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2250/00—Food ingredients
- A23V2250/28—Oligosaccharides
- A23V2250/284—Oligosaccharides, non digestible
-
- 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials Engineering (AREA)
- Animal Husbandry (AREA)
- Zoology (AREA)
- Food Science & Technology (AREA)
- Saccharide Compounds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA3228950A CA3228950C (en) | 2014-07-09 | 2015-07-09 | OLIGOSACCHARIDE COMPOSITIONS AND THEIR PRODUCTION PROCESSES |
| CA3228982A CA3228982A1 (en) | 2014-07-09 | 2015-07-09 | Oligosaccharide compositions and methods for producing thereof |
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201462022579P | 2014-07-09 | 2014-07-09 | |
| US62/022,579 | 2014-07-09 | ||
| US201562108035P | 2015-01-26 | 2015-01-26 | |
| US62/108,035 | 2015-01-26 | ||
| PCT/US2015/039795 WO2016007778A1 (en) | 2014-07-09 | 2015-07-09 | Oligosaccharide compositions and methods for producing thereof |
Related Child Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA3228950A Division CA3228950C (en) | 2014-07-09 | 2015-07-09 | OLIGOSACCHARIDE COMPOSITIONS AND THEIR PRODUCTION PROCESSES |
| CA3228982A Division CA3228982A1 (en) | 2014-07-09 | 2015-07-09 | Oligosaccharide compositions and methods for producing thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2954662A1 CA2954662A1 (en) | 2016-01-14 |
| CA2954662C true CA2954662C (en) | 2024-03-19 |
Family
ID=55064912
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2954662A Active CA2954662C (en) | 2014-07-09 | 2015-07-09 | Oligosaccharide compositions and methods for producing thereof |
| CA3228982A Pending CA3228982A1 (en) | 2014-07-09 | 2015-07-09 | Oligosaccharide compositions and methods for producing thereof |
| CA3228950A Active CA3228950C (en) | 2014-07-09 | 2015-07-09 | OLIGOSACCHARIDE COMPOSITIONS AND THEIR PRODUCTION PROCESSES |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA3228982A Pending CA3228982A1 (en) | 2014-07-09 | 2015-07-09 | Oligosaccharide compositions and methods for producing thereof |
| CA3228950A Active CA3228950C (en) | 2014-07-09 | 2015-07-09 | OLIGOSACCHARIDE COMPOSITIONS AND THEIR PRODUCTION PROCESSES |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US10752705B2 (enExample) |
| EP (1) | EP3166981A4 (enExample) |
| JP (4) | JP7158096B2 (enExample) |
| CN (2) | CN107001528A (enExample) |
| AU (3) | AU2015287703A1 (enExample) |
| BR (1) | BR112017000345B1 (enExample) |
| CA (3) | CA2954662C (enExample) |
| IL (1) | IL249982B2 (enExample) |
| MX (2) | MX378793B (enExample) |
| MY (1) | MY186844A (enExample) |
| WO (1) | WO2016007778A1 (enExample) |
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2676174T3 (es) | 2011-02-28 | 2018-07-17 | Cadena Bio, Inc. | Polímeros que contienen un grupo ácido y su uso como catalizador |
| CA2954662C (en) | 2014-07-09 | 2024-03-19 | Midori Usa, Inc. | Oligosaccharide compositions and methods for producing thereof |
| CN112515178A (zh) * | 2015-01-26 | 2021-03-19 | 卡德纳生物股份有限公司 | 用于营养组合物的寡糖组合物和其制造方法 |
| US10849337B2 (en) | 2015-01-26 | 2020-12-01 | Cadena Bio, Inc. | Oligosaccharide compositions for use as animal feed and methods of producing thereof |
| MX381376B (es) | 2015-01-26 | 2025-03-12 | Kaleido Biosciences Inc | Preparaciones terapéuticas de glicanos y métodos relacionados con estas. |
| EP3285778A2 (en) | 2015-04-23 | 2018-02-28 | Kaleido Biosciences, Inc. | Microbiome regulators and related uses thereof |
| CN107771083A (zh) | 2015-04-23 | 2018-03-06 | 卡莱多生物科技有限公司 | 聚糖治疗剂和治疗方法 |
| WO2018013871A1 (en) | 2016-07-13 | 2018-01-18 | Kaleido Biosciences, Inc. | Glycan compositions and methods of use |
| CN110267663A (zh) | 2016-12-06 | 2019-09-20 | 卡莱多生物科技有限公司 | 聚糖聚合物及其相关方法 |
| JP2020526541A (ja) | 2017-07-13 | 2020-08-31 | カレイド・バイオサイエンシズ・インコーポレイテッド | グリカン組成物及び使用方法 |
| JP7438102B2 (ja) * | 2017-09-07 | 2024-02-26 | メルク・シャープ・アンド・ドーム・エルエルシー | 肺炎球菌多糖体および免疫原性多糖体－キャリアタンパク質コンジュゲートでのその使用 |
| US11524076B2 (en) | 2017-09-07 | 2022-12-13 | Merck Sharp & Dohme Llc | Pneumococcal polysaccharides and their use in immunogenic polysaccharide-carrier protein conjugates |
| US20200245667A1 (en) * | 2017-09-13 | 2020-08-06 | Evolve Biosystems, Inc. | Oligosaccharide compositions and their use during transitional phases of the mammalian gut microbiome |
| US12090168B2 (en) | 2017-11-03 | 2024-09-17 | Dsm Nutritional Products, Llc | Glucose glycans for treating urea cycle disorders |
| EP3704161A1 (en) | 2017-11-03 | 2020-09-09 | Kaleido Biosciences, Inc. | Methods of producing glycan polymers |
| CN111417398A (zh) | 2017-11-03 | 2020-07-14 | 卡莱多生物科技有限公司 | 用于治疗感染的聚糖制剂 |
| EP3530743A1 (en) | 2018-02-21 | 2019-08-28 | Cambridge Glycoscience Ltd | Method of production |
| WO2020035599A1 (en) | 2018-08-15 | 2020-02-20 | Cambridge Glycoscience Ltd. | Novel compositions, their use, and methods for their formation |
| US12410206B2 (en) | 2018-08-21 | 2025-09-09 | Dsm Nutritional Products, Llc | Oligosaccharide compositions and methods of use thereof for reducing ammonia levels |
| KR20210052389A (ko) | 2018-08-27 | 2021-05-10 | 리제너론 파마슈티칼스 인코포레이티드 | 다운스트림 정제에서의 라만 분광법의 사용 |
| SG11202104207TA (en) | 2018-11-08 | 2021-05-28 | Kaleido Biosciences Inc | Oligosaccharide compositions and methods of use thereof |
| ES2987615T3 (es) * | 2018-11-08 | 2024-11-15 | Dsm Ip Assets Bv | Métodos para modular selectivamente el crecimiento microbiano gastrointestinal |
| JP7492096B2 (ja) * | 2018-11-08 | 2024-05-29 | ディーエスエム アイピー アセッツ ビー．ブイ． | オリゴ糖調製物及び組成物 |
| JP7400171B2 (ja) | 2018-11-08 | 2023-12-19 | ディーエスエム アイピー アセッツ ビー．ブイ． | 胃腸代謝物を調節する方法 |
| EP3708356A1 (en) | 2019-03-13 | 2020-09-16 | Sika Technology Ag | A weathering stable thermochromic roofing membrane |
| CA3138903A1 (en) * | 2019-05-08 | 2020-11-12 | Kaleido Biosciences, Inc. | Oligosaccharide compositions and methods of use thereof |
| WO2021032647A1 (en) | 2019-08-16 | 2021-02-25 | Cambridge Glycoscience Ltd | Methods of treating biomass to produce oligosaccharides and related compositions |
| EP4072318A2 (en) | 2019-12-12 | 2022-10-19 | Cambridge Glycoscience Ltd | Low sugar multiphase foodstuffs |
| US20230200412A1 (en) * | 2020-03-13 | 2023-06-29 | Dsm Ip Assets, B.V. | Methods of modulating gastrointestinal microbial metabolic pathways and metabolites |
| US20240000109A1 (en) | 2020-12-03 | 2024-01-04 | Dsm Ip Assets B.V. | Oligosaccharide formulation |
| CN116867498A (zh) * | 2021-02-16 | 2023-10-10 | 帝斯曼知识产权资产管理有限公司 | 用于通过选择性饲料添加剂干预减少致病性大肠杆菌的方法 |
| WO2023110658A1 (en) | 2021-12-13 | 2023-06-22 | Dsm Ip Assets B.V. | Use of oligosaccharide preparation to increase performance of animal vaccinated against coccidiosis |
| WO2023161312A1 (en) | 2022-02-23 | 2023-08-31 | Dsm Ip Assets B.V. | Means and methods for modulating secondary metabolite in an animal |
| EP4489584A1 (en) | 2022-03-09 | 2025-01-15 | DSM IP Assets B.V. | Improving layer bird performance using an oligosaccharide preparation |
| EP4561588A1 (en) | 2022-07-29 | 2025-06-04 | DSM IP Assets B.V. | Reducing necrotic enteritis effect in a bird using an oligosaccharide preparation |
| CN120187311A (zh) * | 2022-10-26 | 2025-06-20 | 帝斯曼知识产权资产管理有限公司 | 包含糖类和氨基酸的制剂和组合物及其用途 |
| CN120897746A (zh) | 2023-04-05 | 2025-11-04 | 帝斯曼知识产权资产管理有限公司 | 对抗呼吸系统疾病作用的寡糖制剂 |
Family Cites Families (145)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2027904A (en) | 1933-02-16 | 1936-01-14 | Int Suiker En Alcohol Cie Inte | Method of polymerizing monosaccharides |
| US2436967A (en) | 1942-04-01 | 1948-03-02 | Corn Prod Refining Co | Polymerization of sugars |
| US2719179A (en) | 1951-01-25 | 1955-09-27 | Mora Peter Tibor | Branched-chain carbohydrate polymers and their preparation |
| US3766165A (en) | 1966-08-17 | 1973-10-16 | Pfizer | Polysaccharides and their preparation |
| US3876794A (en) | 1972-12-20 | 1975-04-08 | Pfizer | Dietetic foods |
| US3973049A (en) | 1974-03-14 | 1976-08-03 | General Foods Corporation | Method of mixing flavors and fixed composition comprising derivatized synthetic polysaccharides |
| US4671967A (en) | 1984-05-18 | 1987-06-09 | Wm. Wrigley Jr. Company | Carbohydrate syrups and methods of preparation |
| US4847338A (en) | 1985-03-28 | 1989-07-11 | University Of Iowa Research Foundation | Low molecular weight heparin fragments as inhibitors of complement activation |
| GB8519416D0 (en) | 1985-08-01 | 1985-09-04 | Unilever Plc | Oligosaccharides |
| WO1987005330A1 (en) | 1986-03-07 | 1987-09-11 | Michel Louis Eugene Bergh | Method for enhancing glycoprotein stability |
| EP0300099A1 (en) | 1987-07-20 | 1989-01-25 | Akzo N.V. | New pentasaccharides |
| US4965354A (en) | 1988-02-26 | 1990-10-23 | Taito Company, Ltd. | Process for producing a condensed polysaccharide |
| US4927811A (en) | 1988-11-15 | 1990-05-22 | Coors Biotech, Inc. | Method and composition for improved animal husbandry |
| US5667593A (en) | 1989-01-26 | 1997-09-16 | Cultor Ltd. | Modified polydextrose and process therefor |
| US5051500A (en) | 1989-08-11 | 1991-09-24 | A. E. Staley Manufacturing Company | Method of preparing a randomly-bonded polysaccharide |
| JPH05213982A (ja) | 1991-03-26 | 1993-08-24 | Dainippon Ink & Chem Inc | オリゴ糖トコフェロール配糖体及び硫酸化オリゴ糖トコフェロール配糖体並びにこれを有効成分とする抗ウイルス剤 |
| AU659896B2 (en) | 1991-12-27 | 1995-06-01 | Matsutani Chemical Industries Co., Ltd. | Feed for livestock which contains galacto-oligosaccharides |
| JPH06121693A (ja) | 1992-08-25 | 1994-05-06 | Akebono Brake Res & Dev Center Ltd | 高重合度オリゴ糖の製造法 |
| FR2697023B1 (fr) | 1992-10-16 | 1994-12-30 | Roquette Freres | Polymère soluble hypocalorique du glucose et procédé de préparation de ce polymère . |
| JPH0770165A (ja) | 1993-06-28 | 1995-03-14 | Hayashibara Biochem Lab Inc | 非還元性オリゴ糖とその製造方法並びに用途 |
| BR9407612A (pt) | 1993-09-24 | 1997-01-14 | Procter & Gamble | Novos compostos de 14-aminoesteróides contendo oligossacarideos e nova química de processo de aminoesteróide diastereosseletivo |
| FR2712891B1 (fr) | 1993-11-22 | 1996-02-02 | Roquette Freres | Procédé de purification d'un polymère soluble hypocalorique du glucose et produit ainsi obtenu. |
| NL9400040A (nl) | 1994-01-10 | 1995-08-01 | Suiker Unie | Werkwijze voor het bereiden van polysaccharidederivaten. |
| US5843922A (en) | 1994-07-29 | 1998-12-01 | Fuisz Technologies Ltd. | Preparation of oligosaccharides and products therefrom |
| US5976580A (en) | 1995-06-07 | 1999-11-02 | Novus International, Inc. | Nutrient formulation and process for enhancing the health, livability, cumulative weight gain or feed efficiency in poultry and other animals |
| JP3413062B2 (ja) * | 1996-06-19 | 2003-06-03 | キヤノン株式会社 | 糖鎖高分子化合物を含む高分子化合物及びその分解方法 |
| US6475552B1 (en) | 1997-03-19 | 2002-11-05 | Danisco Finland Oy | Polymerization of mono and disaccharides using low levels of polycarboxylic acids |
| ATE260300T1 (de) | 1997-03-19 | 2004-03-15 | Danisco Usa Inc | Polymerisation von mono-und disacchariden mit niedrigen mengen an mineralsäuren |
| AUPO888497A0 (en) | 1997-09-01 | 1997-09-25 | Australian National University, The | Use of sulfated oligosaccharides as inhibitors of cardiovascular disease |
| WO1999057300A1 (en) | 1998-05-05 | 1999-11-11 | Mcneil Specialty Products Company Division Of Mcneil-Ppc, Inc. | Functional sugar polymers from inexpensive sugar sources and apparatus for preparing same |
| FR2786775B1 (fr) | 1998-12-04 | 2001-02-16 | Roquette Freres | Maltodextrines branchees et leur procede de preparation |
| DE19860376A1 (de) * | 1998-12-28 | 2000-07-06 | Aventis Res & Tech Gmbh & Co | Alpha-1,4 Glucanketten enthaltende Polysaccharide sowie Verfahren zu ihrer Herstellung |
| JP2001086999A (ja) | 1999-09-22 | 2001-04-03 | Oji Paper Co Ltd | キシロオリゴ糖含有組成物およびガン細胞アポトーシス誘導剤 |
| WO2001038337A2 (en) * | 1999-11-24 | 2001-05-31 | Massachusetts Institute Of Technology | Protecting groups useful in the synthesis of polysaccharides, natural products, and combinatorial libraries |
| DE19961182B4 (de) | 1999-12-18 | 2006-01-12 | Südzucker AG Mannheim/Ochsenfurt | Galactomannan-Oligosaccharide und Verfahren zu deren Herstellung sowie deren Verwendung |
| US7608291B2 (en) | 2000-03-10 | 2009-10-27 | Mars, Inc. | Treatment of infection in animals |
| CA2420247A1 (en) | 2000-08-22 | 2002-02-28 | National Research Council Of Canada | Synthesis of complex carbohydrates |
| DK1355542T3 (da) | 2000-12-27 | 2007-06-11 | Nutricia Nv | Næringssammensætning med sundhedsfremmende virkning, som indeholder oligosaccharider |
| DE10147100A1 (de) | 2001-09-25 | 2003-04-17 | Numico Res B V | Antiinfektive Kohlenhydrate |
| NZ515869A (en) | 2001-11-30 | 2003-09-26 | Med Chem Ingredients Ltd | Compositions and methods for animal treatment comprising gluco- and isomalto- oligosaccharides |
| AU2003245923B2 (en) | 2002-06-07 | 2007-12-13 | Sudzucker Aktiengesellschaft Mannheim/Ochsenfurt | Galactosyl isomalt, method for production and use thereof |
| JP5219329B2 (ja) | 2002-06-28 | 2013-06-26 | ネステク、リミテッド | 下痢の予防又は治療用の医薬組成物 |
| US7524655B2 (en) * | 2002-07-23 | 2009-04-28 | Neose Technologies, Inc. | Synthesis of oligosaccharides, glycolipids, and glycoproteins using bacterial glycosyltransferases |
| EP1578946A4 (en) | 2002-08-23 | 2009-08-26 | Du Pont | USE OF STARCH PRODUCTS IN BIOLOGICAL PRODUCTION BY FERMENTATION |
| US20040052915A1 (en) | 2002-09-13 | 2004-03-18 | Carlson Ting L. | Use of low glycemic index sweeteners in food and beverage compositions |
| US20060067947A1 (en) | 2002-09-19 | 2006-03-30 | Orient Cancer Therapy Co., Ltd. | Immunotherapeutic for cancer |
| FI20021772A7 (fi) | 2002-10-04 | 2004-04-05 | Biotie Therapies Oyj | Uudet hiilihydraattikoostumukset ja menetelmä niiden valmistamiseksi |
| JP3899462B2 (ja) | 2002-12-02 | 2007-03-28 | 独立行政法人農業・食品産業技術総合研究機構 | ガン細胞アポトーシス誘導剤 |
| GB0229015D0 (en) | 2002-12-12 | 2003-01-15 | Novartis Nutrition Ag | New Compound |
| TWI330641B (en) | 2002-12-24 | 2010-09-21 | Yasuhiro Kajihara | Sugar chain asparagine derivatives |
| US7291607B2 (en) | 2003-05-20 | 2007-11-06 | Board Of Supervisors Of Louisiana State University And Agricultural And Mechanical College | Isomaltooligosaccharides from Leuconostoc as neutraceuticals |
| EP1626053B1 (en) | 2003-05-22 | 2011-07-06 | Japan Science and Technology Agency | Method of alpha-selective glycosylation |
| DE602004006133T3 (de) | 2003-06-30 | 2014-12-24 | Clasado Inc. | Neue galactooligosaccharidzusammensetzung und herstellung davon |
| JP4597630B2 (ja) | 2003-10-29 | 2010-12-15 | 株式会社神戸製鋼所 | 表面処理方法及び装置 |
| CN1562050A (zh) | 2004-03-24 | 2005-01-12 | 中国海洋大学 | 褐藻酸寡糖在抗痴呆、抗糖尿病中的应用 |
| EP1634599A1 (en) | 2004-08-20 | 2006-03-15 | N.V. Nutricia | Iimmune stimulatory infant nutrition |
| FR2874825B1 (fr) | 2004-09-08 | 2006-12-08 | Genibio Sarl | Utilisations d'oligosaccharides prebiotiques benefiques pour la flore vaginale |
| JP4983258B2 (ja) | 2004-09-27 | 2012-07-25 | 株式会社林原 | イソサイクロマルトオリゴ糖及びイソサイクロマルトオリゴ糖生成酵素とそれらの製造方法並びに用途 |
| US20060093592A1 (en) | 2004-10-04 | 2006-05-04 | Nutracea | Synbiotics |
| CN1255041C (zh) | 2004-10-27 | 2006-05-10 | 李向群 | 一种甲壳胺饲料添加剂的制备方法 |
| DE102004058811A1 (de) * | 2004-12-07 | 2006-06-08 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Verfahren zur Herstellung von Zuckeralkoholen |
| WO2007010084A2 (en) | 2005-07-15 | 2007-01-25 | Johannes Savolainen | Immunostimulatory oligo- and polysaccharides and uses thereof |
| TWI342880B (en) | 2005-07-19 | 2011-06-01 | Otsuka Chemical Co Ltd | Method for producing sugar chain derivatives, and sugar chain derivatives |
| WO2007015937A1 (en) | 2005-07-27 | 2007-02-08 | Cantabria Group Lcc | Phosphorytated glucomannan polysaccharides containing 1-6 and 1-2 linkages increase weight gain in swine |
| BRPI0615117A2 (pt) | 2005-08-25 | 2011-05-03 | Archer Daniels Midland Co | uso de dextrinas na alimentação de animais |
| US8530447B2 (en) | 2005-10-24 | 2013-09-10 | Nestec S.A. | Dietary fiber formulation and method of administration |
| CN102948659B (zh) | 2005-12-16 | 2014-04-23 | 纽崔西亚公司 | 碳水化合物组合物 |
| US8057840B2 (en) | 2006-01-25 | 2011-11-15 | Tate & Lyle Ingredients Americas Llc | Food products comprising a slowly digestible or digestion resistant carbohydrate composition |
| US7608436B2 (en) | 2006-01-25 | 2009-10-27 | Tate & Lyle Ingredients Americas, Inc. | Process for producing saccharide oligomers |
| US8993039B2 (en) | 2006-01-25 | 2015-03-31 | Tate & Lyle Ingredients Americas Llc | Fiber-containing carbohydrate composition |
| FR2897869B1 (fr) | 2006-02-28 | 2011-05-06 | Roquette Freres | Polymeres solubles de glucose hautement branches pour la nutrition enterale, parenterale et pour la dialyse peritoneale |
| US7915235B2 (en) | 2006-03-20 | 2011-03-29 | Brian Dieckgraefe | High affinity ligands bind to clostridium difficile toxin A |
| EP2012807A4 (en) | 2006-04-10 | 2009-07-08 | Dikovskiy Aleksander Vladimiro | PHARMACEUTICAL COMPOSITION FROM AN ENTEROSORBEN AND PREBIOTIKA, DOSAGE FORMS AND METHOD FOR THE PREVENTION AND TREATMENT OF GASTROINTESTINAL DISEASES |
| EP1886696A1 (en) | 2006-08-03 | 2008-02-13 | Endotis Pharma | Conjugates of antithrombin binding oligosaccharide derivatives and therapeutic proteins |
| EP1887017A1 (en) | 2006-08-09 | 2008-02-13 | Friesland Brands B.V. | Prebiotic carbohydrate |
| US20080069861A1 (en) | 2006-09-19 | 2008-03-20 | National Starch And Chemical Investment Holding Corporation | Probiotic/Non-Probiotic Combinations |
| FI20065593L (fi) | 2006-09-26 | 2008-03-27 | Valio Oy | Menetelmä galakto-oligosakkarideja sisältävien tuotteiden valmistamiseksi ja niiden käyttö |
| US20130216693A1 (en) * | 2007-01-24 | 2013-08-22 | Tate & Lyle Ingredients Americas Llc | Fiber-containing carbohydrate composition |
| ES2304223B2 (es) | 2007-03-08 | 2009-05-01 | Universidad De Sevilla | Nuevos caramelos con elevado contenido en oligosacaridos prebioticos, procedimiento de preparacion y utilizacion. |
| US8197872B2 (en) | 2007-05-17 | 2012-06-12 | The Regents Of The University Of California | Human milk oligosaccharides to promote growth of beneficial gut bacteria |
| CA2591253A1 (en) | 2007-06-05 | 2008-12-05 | Institut Pasteur | Specific oligosaccharides of shigella flexneri serotypes 3a and x, their synthesis, compositions comprising them and their uses thereof |
| WO2008156354A1 (en) | 2007-06-21 | 2008-12-24 | N.V. Nutricia | Modulation of intestinal flora of hiv patients |
| RU2010122324A (ru) | 2007-11-02 | 2011-12-10 | Момента Фармасьютикалз, Инк. (Us) | Полисахаридные композиции, не обладающие антикоагулянтными свойствами |
| EP2234505B1 (en) | 2007-12-21 | 2013-01-30 | N.V. Nutricia | Use of sphingomyelin and non-digestible carbohydrates for improving intestinal microbiota |
| ITBA20080008A1 (it) | 2008-02-22 | 2009-08-23 | Michele Barone | Composizioni comprendenti fitoestrogeni selettivi per il recettore estrogenico beta e fibre dietetiche |
| EP2282648A4 (en) | 2008-06-09 | 2011-09-21 | Temple Inland | PREBIOTIC COMPOSITIONS AND MANUFACTURING AND USE METHOD THEREFOR |
| ES2336297B1 (es) | 2008-10-08 | 2011-01-24 | Laboratorios Farmaceuticos Rovi, S.A. | Procedimiento de sintesis de pentasacaridos desprotegidos a partir deun pentasacarido precursos protegido. |
| FR2938541B1 (fr) | 2008-11-20 | 2011-08-26 | Sanofi Aventis | Pentasaccharide cristallise,son procede d'obtention et son utilisation pour la preparation d'idraparinux |
| PL2355670T3 (pl) | 2008-12-10 | 2013-10-31 | Univ Leuven Kath | Środek odżywczy zawierający arabinoksylan i oligosacharydy |
| FI20080665A0 (fi) | 2008-12-18 | 2008-12-18 | Glykos Finland Oy | Luonnollisen tyyppiset sakkaridikoostumukset |
| WO2010105207A1 (en) | 2009-03-13 | 2010-09-16 | The Regents Of The University Of California | Prebiotic oligosaccharides |
| US8816067B2 (en) | 2009-05-07 | 2014-08-26 | Tate & Lyle Ingredients France SAS | Compositions and methods for making alpha-(1,2)-branched alpha-(1,6) oligodextrans |
| EP2248907A1 (en) | 2009-05-08 | 2010-11-10 | Rijksuniversiteit Groningen | Gluco-oligosaccharides comprising (alpha 1-->4) and (alpha 1-->6) glycosidic bonds, use thereof, and methods for providing them |
| CA2763384C (en) | 2009-05-27 | 2014-07-08 | Clasado Inc | Use of a composition of a mixture of galactooligosaccharides for preventing diarrhoea |
| WO2010143940A1 (en) | 2009-06-12 | 2010-12-16 | N.V. Nutricia | Synergistic mixture of beta-galacto-oligosaccharides with beta-1,3 and beta-1,4/1,6 linkages |
| EP2662084A1 (en) | 2009-07-15 | 2013-11-13 | N.V. Nutricia | Mixture of non-digestible oligosaccharides for stimulating the immune system |
| US8691792B2 (en) | 2009-08-05 | 2014-04-08 | Nestec Sa | Methods and compositions for improving gastrointetinal health |
| DE102010025323A1 (de) | 2010-02-19 | 2011-08-25 | Krüger GmbH & Co. KG, 51469 | Neue Süßstoffzusammensetzungen |
| DE102010012282A1 (de) * | 2010-03-22 | 2011-09-22 | Fresenius Medical Care Deutschland Gmbh | Pharmazeutische Zusammensetzung enthaltend Cyclodextrin-Copolymer |
| JP5720108B2 (ja) | 2010-04-02 | 2015-05-20 | セイコーエプソン株式会社 | 血管表示装置 |
| BE1019290A5 (nl) | 2010-04-14 | 2012-05-08 | Nutrition Sciences Nv Sa | Voedingsupplement omvattende oligosachariden en middellange keten vetzuren. |
| EP2386563A1 (en) | 2010-05-12 | 2011-11-16 | Institut Pasteur | Novel O-acetylated decasaccharides |
| PT3401410T (pt) | 2010-06-26 | 2021-04-05 | Virdia Llc | Métodos para produção de misturas de açúcar |
| EP2401925B1 (fr) | 2010-06-29 | 2014-05-07 | Rosebud AG | Produit prebiotique et procede de fabrication |
| CN103108956A (zh) | 2010-07-16 | 2013-05-15 | 格力康公司 | 新型唾液酸寡糖衍生物的合成 |
| US20120020740A1 (en) | 2010-07-21 | 2012-01-26 | Norio Otsuga | Connection structure for a manhole pipe and a sewer main pipe |
| US20120034366A1 (en) | 2010-08-05 | 2012-02-09 | Tate & Lyle Ingredients Americas, Inc. | Carbohydrate compositions |
| EP2465507A1 (en) | 2010-11-23 | 2012-06-20 | Nestec S.A. | Oligosaccharide composition for treating skin diseases |
| EP2455387A1 (en) | 2010-11-23 | 2012-05-23 | Nestec S.A. | Oligosaccharide mixture and food product comprising this mixture, especially infant formula |
| JP2012158526A (ja) * | 2011-01-31 | 2012-08-23 | Niigata Institute Of Science & Technology Niigata Univ Of Pharmacy & Applied Life Sciences | マンノオリゴ糖の製造法 |
| US20140187474A1 (en) | 2011-02-16 | 2014-07-03 | The Board Of Trustees Of The Leland Stanford Junior University | Therapeutic use of mucin glycans |
| CA2827294A1 (en) | 2011-02-21 | 2012-08-30 | Glycom A/S | Catalytic hydrogenolysis of a composition of a mixture of oligosaccharide precursors and uses thereof |
| ES2676174T3 (es) * | 2011-02-28 | 2018-07-17 | Cadena Bio, Inc. | Polímeros que contienen un grupo ácido y su uso como catalizador |
| WO2012127410A1 (en) | 2011-03-18 | 2012-09-27 | Glycom A/S | Synthesis of new fucose-containing carbohydrate derivatives |
| EP2522232A1 (en) | 2011-05-13 | 2012-11-14 | Nestec S.A. | Nutritional products comprising human milk oligosaccharides and methods for manufacture thereof |
| BR112013029208A2 (pt) | 2011-05-13 | 2017-02-14 | Glycom As | método para preparar um ou mais oligossarídeos de leite humano ou derivados ou precursores dos mesmos, uso de oligossacarídeos, e, composto |
| WO2013082562A1 (en) | 2011-11-30 | 2013-06-06 | Ritter Pharmaceuticals, Inc. | Prebiotic formulations and methods of use |
| FR2987360B1 (fr) | 2012-02-28 | 2014-03-28 | Roquette Freres | Maltodextrines hyperbranchees hypo-glycemiantes |
| EP2666788A1 (en) | 2012-05-21 | 2013-11-27 | Nederlandse Organisatie voor toegepast -natuurwetenschappelijk onderzoek TNO | Glucan fibre |
| CN103578010A (zh) | 2012-07-26 | 2014-02-12 | 阿里巴巴集团控股有限公司 | 生成流量质量比较参数的方法和装置、广告计费方法 |
| EP2888043A4 (en) | 2012-08-24 | 2016-05-04 | Midori Usa Inc | POLYMERIC AND SOLID-SUPPORTED CATALYSTS, AND METHODS OF DIGESTIONING LIGNIN-CONTAINING SUBSTANCES USING SUCH CATALYSTS |
| US9238845B2 (en) * | 2012-08-24 | 2016-01-19 | Midori Usa, Inc. | Methods of producing sugars from biomass feedstocks |
| CA2922254A1 (en) | 2012-08-24 | 2014-02-27 | Midori Usa, Inc. | Polymeric and solid-supported catalysts, and methods of digesting cellulosic materials using such catalysts |
| US20150202607A1 (en) | 2012-08-24 | 2015-07-23 | Midori Renewables, Inc. | Polymeric and solid-supported catalysts, and methods of digesting cellulosic materials using such catalysts |
| WO2014043708A1 (en) | 2012-09-17 | 2014-03-20 | Traber Peter G | Method for enhancing specific immunotherapies in cancer treatment |
| US9045804B2 (en) | 2013-01-08 | 2015-06-02 | Wisconsin Alumni Research Foundation | Method to produce water-soluble sugars from biomass using solvents containing lactones |
| DK2769726T3 (en) | 2013-02-21 | 2019-02-25 | Jennewein Biotechnologie Gmbh | Synthetic or recombinant fucosylated oligosaccharides for use in the treatment of infections |
| AU2014240435A1 (en) | 2013-03-14 | 2015-09-17 | Midori Usa, Inc. | Polymeric ionic salt catalysts and methods of producing thereof |
| EP2983514A4 (en) | 2013-03-15 | 2017-03-15 | Cargill, Incorporated | Carbohydrate compositions |
| JP2016521284A (ja) | 2013-05-10 | 2016-07-21 | カリフォルニア インスティチュート オブ テクノロジー | 大腸ガンのプロバイオティクスによる防止および処置 |
| RU2691408C2 (ru) | 2013-12-27 | 2019-06-13 | Колгейт-Палмолив Компани | Способы ухода за полостью рта с использованием сахарида в качестве пребиотика |
| EP3125905A4 (en) | 2014-04-04 | 2017-11-08 | Ritter Pharmaceuticals, Inc. | Methods and compositions for microbiome alteration |
| CN104171365A (zh) | 2014-07-02 | 2014-12-03 | 中泰和（北京）科技发展有限公司 | 一种提高仔猪断奶重的母猪饲料添加剂及其应用方案 |
| CA2954662C (en) | 2014-07-09 | 2024-03-19 | Midori Usa, Inc. | Oligosaccharide compositions and methods for producing thereof |
| US10849337B2 (en) | 2015-01-26 | 2020-12-01 | Cadena Bio, Inc. | Oligosaccharide compositions for use as animal feed and methods of producing thereof |
| RU2017130166A (ru) | 2015-01-26 | 2019-02-28 | Кадена Байо, Инк. | Олигосахаридные композиции для применения в качестве пищевых ингредиентов и способы их получения |
| CN112515178A (zh) | 2015-01-26 | 2021-03-19 | 卡德纳生物股份有限公司 | 用于营养组合物的寡糖组合物和其制造方法 |
| US9492473B2 (en) | 2015-01-26 | 2016-11-15 | Kaleido Biosciences, Inc. | Glycan therapeutics and related methods thereof |
| MX381376B (es) | 2015-01-26 | 2025-03-12 | Kaleido Biosciences Inc | Preparaciones terapéuticas de glicanos y métodos relacionados con estas. |
| FR3032709B1 (fr) | 2015-02-16 | 2017-02-24 | Roquette Freres | Malto-oligo-saccharides riches en fibres et presentant une faible biosdisponibilite en glucose, leur procede de fabrication et leurs utilisations en nutrition humaine et animale |
| CN107771083A (zh) | 2015-04-23 | 2018-03-06 | 卡莱多生物科技有限公司 | 聚糖治疗剂和治疗方法 |
| EP3285778A2 (en) | 2015-04-23 | 2018-02-28 | Kaleido Biosciences, Inc. | Microbiome regulators and related uses thereof |
| WO2017083520A1 (en) | 2015-11-13 | 2017-05-18 | Cadena Bio, Inc. | Animal therapeutic and feed compositions and methods of use |
| CN110267663A (zh) | 2016-12-06 | 2019-09-20 | 卡莱多生物科技有限公司 | 聚糖聚合物及其相关方法 |
| US11484547B2 (en) | 2018-01-08 | 2022-11-01 | Performance Labs PTE. LTD. | Compositions and methods for cholesterol, glucose and microbiome control |
-
2015
- 2015-07-09 CA CA2954662A patent/CA2954662C/en active Active
- 2015-07-09 US US14/795,720 patent/US10752705B2/en active Active
- 2015-07-09 CA CA3228982A patent/CA3228982A1/en active Pending
- 2015-07-09 WO PCT/US2015/039795 patent/WO2016007778A1/en not_active Ceased
- 2015-07-09 AU AU2015287703A patent/AU2015287703A1/en not_active Abandoned
- 2015-07-09 CN CN201580048065.6A patent/CN107001528A/zh active Pending
- 2015-07-09 MX MX2017000319A patent/MX378793B/es unknown
- 2015-07-09 CN CN202010078515.9A patent/CN111471117A/zh active Pending
- 2015-07-09 JP JP2017522455A patent/JP7158096B2/ja active Active
- 2015-07-09 EP EP15819734.3A patent/EP3166981A4/en active Pending
- 2015-07-09 CA CA3228950A patent/CA3228950C/en active Active
- 2015-07-09 BR BR112017000345-7A patent/BR112017000345B1/pt active IP Right Grant
- 2015-07-09 MY MYPI2017000019A patent/MY186844A/en unknown
-
2017
- 2017-01-06 MX MX2021000229A patent/MX2021000229A/es unknown
- 2017-01-08 IL IL249982A patent/IL249982B2/en unknown
-
2019
- 2019-08-28 AU AU2019222849A patent/AU2019222849B2/en active Active
-
2020
- 2020-06-25 US US16/912,368 patent/US11584805B2/en active Active
- 2020-10-16 JP JP2020174799A patent/JP2021035953A/ja active Pending
-
2021
- 2021-09-22 AU AU2021236493A patent/AU2021236493B2/en active Active
-
2022
- 2022-11-04 JP JP2022177221A patent/JP2023011860A/ja active Pending
-
2025
- 2025-02-28 JP JP2025031182A patent/JP2025084883A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| MX378793B (es) | 2025-03-11 |
| AU2019222849A1 (en) | 2019-09-19 |
| CA3228982A1 (en) | 2016-01-14 |
| US10752705B2 (en) | 2020-08-25 |
| JP2021035953A (ja) | 2021-03-04 |
| CA3228950A1 (en) | 2016-01-14 |
| US20210002387A1 (en) | 2021-01-07 |
| AU2015287703A1 (en) | 2017-02-16 |
| IL249982B (en) | 2022-11-01 |
| JP2023011860A (ja) | 2023-01-24 |
| IL249982B2 (en) | 2023-03-01 |
| JP2017522380A (ja) | 2017-08-10 |
| MX2021000229A (es) | 2021-03-31 |
| US11584805B2 (en) | 2023-02-21 |
| BR112017000345A2 (pt) | 2017-10-31 |
| EP3166981A1 (en) | 2017-05-17 |
| AU2019222849B2 (en) | 2021-10-21 |
| MX2017000319A (es) | 2017-04-27 |
| IL249982A0 (en) | 2017-03-30 |
| JP2025084883A (ja) | 2025-06-03 |
| AU2021236493B2 (en) | 2024-03-28 |
| US20160007642A1 (en) | 2016-01-14 |
| AU2021236493A1 (en) | 2021-10-21 |
| WO2016007778A1 (en) | 2016-01-14 |
| CN111471117A (zh) | 2020-07-31 |
| CA3228950C (en) | 2025-11-18 |
| BR112017000345B1 (pt) | 2022-04-26 |
| CA2954662A1 (en) | 2016-01-14 |
| JP7158096B2 (ja) | 2022-10-21 |
| EP3166981A4 (en) | 2018-03-07 |
| CN107001528A (zh) | 2017-08-01 |
| MY186844A (en) | 2021-08-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2954662C (en) | Oligosaccharide compositions and methods for producing thereof | |
| AU2020239805B2 (en) | Oligosaccharide compositions for use in nutritional compositions, and methods of producing thereof | |
| US20220400728A1 (en) | Oligosaccharide compositions for use as food ingredients and methods of producing thereof | |
| KR20150047583A (ko) | 중합체 촉매와 고체-지지된 촉매, 및 이러한 촉매를 사용하여 셀룰로오스 물질을 분해하는 방법 | |
| CN107250123B (zh) | 用于将纤维素转化为呋喃产物的方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20200709 |
|
| EEER | Examination request |
Effective date: 20200709 |
|
| EEER | Examination request |
Effective date: 20200709 |
|
| EEER | Examination request |
Effective date: 20200709 |
|
| EEER | Examination request |
Effective date: 20200709 |
|
| EEER | Examination request |
Effective date: 20200709 |
|
| EEER | Examination request |
Effective date: 20200709 |
|
| EEER | Examination request |
Effective date: 20200709 |
|
| EEER | Examination request |
Effective date: 20200709 |
|
| EEER | Examination request |
Effective date: 20200709 |
|
| EEER | Examination request |
Effective date: 20200709 |
|
| EEER | Examination request |
Effective date: 20200709 |