EP4379068A1 - Dérivés iridoïdes ou séco-iridoïdes et leur utilisation dans un procédé de tannage - Google Patents
Dérivés iridoïdes ou séco-iridoïdes et leur utilisation dans un procédé de tannage Download PDFInfo
- Publication number
- EP4379068A1 EP4379068A1 EP22306770.3A EP22306770A EP4379068A1 EP 4379068 A1 EP4379068 A1 EP 4379068A1 EP 22306770 A EP22306770 A EP 22306770A EP 4379068 A1 EP4379068 A1 EP 4379068A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- aliphatic group
- hydrogen
- compound
- formula
- hydrogen atom
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims abstract description 46
- 108010035532 Collagen Proteins 0.000 claims abstract description 75
- 102000008186 Collagen Human genes 0.000 claims abstract description 75
- 229920001436 collagen Polymers 0.000 claims abstract description 75
- 238000004132 cross linking Methods 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 104
- 150000001875 compounds Chemical class 0.000 claims description 101
- 229910052739 hydrogen Inorganic materials 0.000 claims description 66
- 239000001257 hydrogen Substances 0.000 claims description 66
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 36
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 34
- 239000000463 material Substances 0.000 claims description 27
- -1 apodanthoside Chemical compound 0.000 claims description 24
- IBFYXTRXDNAPMM-BVTMAQQCSA-N Geniposide Chemical compound O([C@@H]1OC=C([C@@H]2[C@H]1C(=CC2)CO)C(=O)OC)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O IBFYXTRXDNAPMM-BVTMAQQCSA-N 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 19
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 17
- IBFYXTRXDNAPMM-FZEIBHLUSA-N Geniposide Natural products COC(=O)C1=CO[C@@H](O[C@H]2O[C@@H](CO)[C@H](O)[C@@H](O)[C@@H]2O)[C@H]2[C@@H]1CC=C2CO IBFYXTRXDNAPMM-FZEIBHLUSA-N 0.000 claims description 16
- VGLLGNISLBPZNL-RBUKDIBWSA-N arborescoside Natural products O=C(OC)C=1[C@@H]2C([C@H](O[C@H]3[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O3)OC=1)=C(CO)CC2 VGLLGNISLBPZNL-RBUKDIBWSA-N 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- BZPMXJKRKXDRID-UOIKKKDVSA-N Scandoside Natural products OC[C@H]1O[C@@H](O[C@H]2CC=C([C@@H]3[C@@H](O)C=C(CO)[C@H]23)C(=O)O)[C@H](O)[C@@H](O)[C@@H]1O BZPMXJKRKXDRID-UOIKKKDVSA-N 0.000 claims description 12
- 125000001931 aliphatic group Chemical group 0.000 claims description 12
- 239000010985 leather Substances 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 11
- HKVGJQVJNQRJPO-UHFFFAOYSA-N Demethyloleuropein Natural products O1C=C(C(O)=O)C(CC(=O)OCCC=2C=C(O)C(O)=CC=2)C(=CC)C1OC1OC(CO)C(O)C(O)C1O HKVGJQVJNQRJPO-UHFFFAOYSA-N 0.000 claims description 10
- DUAGQYUORDTXOR-GPQRQXLASA-N Gentiopicrin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@H]1[C@H](C=C)C2=CCOC(=O)C2=CO1 DUAGQYUORDTXOR-GPQRQXLASA-N 0.000 claims description 10
- DUAGQYUORDTXOR-WULZUDSJSA-N Gentiopicrin Natural products O([C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1)[C@H]1[C@@H](C=C)C=2C(C(=O)OCC=2)=CO1 DUAGQYUORDTXOR-WULZUDSJSA-N 0.000 claims description 10
- AMBQHHVBBHTQBF-UHFFFAOYSA-N Loganin Natural products C12C(C)C(O)CC2C(C(=O)OC)=COC1OC1OC(CO)C(O)C(O)C1O AMBQHHVBBHTQBF-UHFFFAOYSA-N 0.000 claims description 9
- WSGPLSDARZNMCW-FCVLBCLDSA-N 6beta-Hydroxygeniposide Natural products O([C@@H]1OC=C([C@@H]2[C@H]1C(=C[C@@H]2O)CO)C(=O)OC)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O WSGPLSDARZNMCW-FCVLBCLDSA-N 0.000 claims description 8
- RFWGABANNQMHMZ-UHFFFAOYSA-N 8-acetoxy-7-acetyl-6,7,7a,8-tetrahydro-5H-benzo[g][1,3]dioxolo[4',5':4,5]benzo[1,2,3-de]quinoline Natural products CC=C1C(CC(=O)OCCC=2C=C(O)C(O)=CC=2)C(C(=O)OC)=COC1OC1OC(CO)C(O)C(O)C1O RFWGABANNQMHMZ-UHFFFAOYSA-N 0.000 claims description 8
- WSGPLSDARZNMCW-UHFFFAOYSA-N Deacetylasperulosidsaeure-methylester Natural products OC1C=C(CO)C2C1C(C(=O)OC)=COC2OC1OC(CO)C(O)C(O)C1O WSGPLSDARZNMCW-UHFFFAOYSA-N 0.000 claims description 8
- YTZSBJLNMIQROD-SFBCHFHNSA-N Morroniside Chemical compound O([C@@H]1OC=C([C@H]2C[C@H](O)O[C@@H](C)[C@H]21)C(=O)OC)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O YTZSBJLNMIQROD-SFBCHFHNSA-N 0.000 claims description 8
- VELYAQRXBJLJAK-UHFFFAOYSA-N myoporoside Natural products C12C(C)(O)CC(O)C2C=COC1OC1OC(CO)C(O)C(O)C1O VELYAQRXBJLJAK-UHFFFAOYSA-N 0.000 claims description 8
- 239000002649 leather substitute Substances 0.000 claims description 7
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 6
- RFWGABANNQMHMZ-HYYSZPHDSA-N Oleuropein Chemical compound O([C@@H]1OC=C([C@H](C1=CC)CC(=O)OCCC=1C=C(O)C(O)=CC=1)C(=O)OC)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O RFWGABANNQMHMZ-HYYSZPHDSA-N 0.000 claims description 6
- 125000003147 glycosyl group Chemical group 0.000 claims description 6
- RFWGABANNQMHMZ-CARRXEGNSA-N oleuropein Natural products COC(=O)C1=CO[C@@H](O[C@H]2O[C@@H](CO)[C@H](O)[C@@H](O)[C@@H]2O)C(=CC)[C@H]1CC(=O)OCCc3ccc(O)c(O)c3 RFWGABANNQMHMZ-CARRXEGNSA-N 0.000 claims description 6
- 235000011576 oleuropein Nutrition 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- AMBQHHVBBHTQBF-UOUCRYGSSA-N loganin Chemical compound O([C@@H]1OC=C([C@H]2C[C@H](O)[C@H](C)[C@H]21)C(=O)OC)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O AMBQHHVBBHTQBF-UOUCRYGSSA-N 0.000 claims description 5
- CSKKDSFETGLMSB-NRZPKYKESA-N (-)-secologanin Chemical compound C=C[C@@H]1[C@H](CC=O)C(C(=O)OC)=CO[C@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CSKKDSFETGLMSB-NRZPKYKESA-N 0.000 claims description 4
- ZVXWFPTVHBWJOU-AWQYILTISA-N (1s,4as,5r,7as)-5-hydroxy-7-(hydroxymethyl)-1-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylic acid Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@H]1[C@@H]2C(CO)=C[C@@H](O)[C@@H]2C(C(O)=O)=CO1 ZVXWFPTVHBWJOU-AWQYILTISA-N 0.000 claims description 4
- XUWSHXDEJOOIND-YYDKPPGPSA-N (1s,4as,5r,7s,7ar)-7-methyl-1-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,5,6,7a-tetrahydrocyclopenta[c]pyran-4a,5,7-triol Chemical compound O([C@@H]1OC=C[C@@]2(O)[C@H](O)C[C@@]([C@@H]12)(O)C)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O XUWSHXDEJOOIND-YYDKPPGPSA-N 0.000 claims description 4
- VELYAQRXBJLJAK-XKKWFBPMSA-N (2s,3r,4s,5s,6r)-2-[[(1s,4ar,5r,7s,7as)-5,7-dihydroxy-7-methyl-4a,5,6,7a-tetrahydro-1h-cyclopenta[c]pyran-1-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound O([C@@H]1OC=C[C@H]2[C@H](O)C[C@@]([C@@H]12)(O)C)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O VELYAQRXBJLJAK-XKKWFBPMSA-N 0.000 claims description 4
- YTZSBJLNMIQROD-UHFFFAOYSA-N (4aS)-1c-beta-D-glucopyranosyloxy-6xi-hydroxy-8t-methyl-(4ar,8ac)-5,6,8,8a-tetrahydro-1H,4aH-pyrano[3,4-c]pyran-4-carboxylic acid methyl ester Natural products C12C(C)OC(O)CC2C(C(=O)OC)=COC1OC1OC(CO)C(O)C(O)C1O YTZSBJLNMIQROD-UHFFFAOYSA-N 0.000 claims description 4
- DBOVHQOUSDWAPQ-UHFFFAOYSA-N (4aS)-6c-[O2-(3,5,3'-trihydroxy-biphenyl-2-carbonyl)-beta-D-glucopyranosyloxy]-5t-vinyl-(4ar)-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-1-one Natural products OC1C(O)C(CO)OC(OC2C(C3C(C(OCC3)=O)=CO2)C=C)C1OC(=O)C1=C(O)C=C(O)C=C1C1=CC=CC(O)=C1 DBOVHQOUSDWAPQ-UHFFFAOYSA-N 0.000 claims description 4
- GMQXOLRKJQWPNB-UHFFFAOYSA-N (8E)-ligstroside Natural products CC=C1C(CC(=O)OCCC=2C=CC(O)=CC=2)C(C(=O)OC)=COC1OC1OC(CO)C(O)C(O)C1O GMQXOLRKJQWPNB-UHFFFAOYSA-N 0.000 claims description 4
- JNNGEAWILNVFFD-DXNVVGTLSA-N 7-Epiloganic acid Chemical compound O([C@H]1[C@H]2[C@@H](C(=CO1)C(O)=O)C[C@@H](O)[C@@H]2C)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O JNNGEAWILNVFFD-DXNVVGTLSA-N 0.000 claims description 4
- VELYAQRXBJLJAK-TYNWJONJSA-N Ajugol Natural products O([C@@H]1[C@@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1)[C@@H]1OC=C[C@@H]2[C@H](O)C[C@@](O)(C)[C@@H]12 VELYAQRXBJLJAK-TYNWJONJSA-N 0.000 claims description 4
- BZXINCMCFVKGKB-UHFFFAOYSA-N Amarogentin Natural products OCC1OC(OC2OC=C3C(CCOC3=O)C2C=C)C(OC(=O)c4cc(O)cc(O)c4c5cccc(O)c5)C(O)C1O BZXINCMCFVKGKB-UHFFFAOYSA-N 0.000 claims description 4
- UBAIOTDKPLIEDD-RNCITLLOSA-N Antirrhinoside Chemical compound O([C@@H]1OC=C[C@@]2(O)[C@H](O)[C@@H]3O[C@@]3([C@@H]12)C)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O UBAIOTDKPLIEDD-RNCITLLOSA-N 0.000 claims description 4
- QIIDATRCGITYRZ-UHFFFAOYSA-N Catalpol Natural products OCC1OC(OC2OC=CC3C(O)C(=C(CO)C23)O)C(O)C(O)C1O QIIDATRCGITYRZ-UHFFFAOYSA-N 0.000 claims description 4
- XJMPAUZQVRGFRE-SCHFUKFYSA-N Gardenoside Natural products O=C(OC)C=1[C@H]2[C@H]([C@H](O[C@H]3[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O3)OC=1)[C@@](O)(CO)C=C2 XJMPAUZQVRGFRE-SCHFUKFYSA-N 0.000 claims description 4
- ZJDOESGVOWAULF-OGJQONSISA-N Geniposidic acid Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@H]1[C@@H]2C(CO)=CC[C@@H]2C(C(O)=O)=CO1 ZJDOESGVOWAULF-OGJQONSISA-N 0.000 claims description 4
- VYAALAFRWREWLA-BVTMAQQCSA-N Geniposidic acid Natural products CCC1=CC[C@H]2[C@@H]1[C@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)OC=C2C(=O)O VYAALAFRWREWLA-BVTMAQQCSA-N 0.000 claims description 4
- ZJDOESGVOWAULF-UHFFFAOYSA-N Geniposidinsaeure Natural products OC1C(O)C(O)C(CO)OC1OC1C2C(CO)=CCC2C(C(O)=O)=CO1 ZJDOESGVOWAULF-UHFFFAOYSA-N 0.000 claims description 4
- WDYYXHRRDDQKPP-UHFFFAOYSA-N Ligustaloside A Natural products COC(=O)C1=COC(OC2OC(CO)C(O)C(O)C2O)C(CC=O)C1CC(=O)OCCc3ccc(O)c(O)c3 WDYYXHRRDDQKPP-UHFFFAOYSA-N 0.000 claims description 4
- BWUBCXXBORKPMI-UHFFFAOYSA-N Ligustaloside B Natural products COC(=O)C1=COC(OC2OC(CO)C(O)C(O)C2O)C(CC=O)C1COC(=O)CCc3ccc(O)cc3 BWUBCXXBORKPMI-UHFFFAOYSA-N 0.000 claims description 4
- MNUBZBVTOJCOGO-UHFFFAOYSA-N Ligustrosidic acid Natural products COC(=O)C1=COC(OC2OC(CO)C(O)C(O)C2O)C(=CC(=O)O)C1COC(=O)CCc3ccc(O)cc3 MNUBZBVTOJCOGO-UHFFFAOYSA-N 0.000 claims description 4
- DRWIVSAUXCDFQK-UHFFFAOYSA-N Linarioside Natural products C12C(C)(O)C(Cl)C(O)C2(O)C=COC1OC1OC(CO)C(O)C(O)C1O DRWIVSAUXCDFQK-UHFFFAOYSA-N 0.000 claims description 4
- WMQIBEYREGDWOS-UOUCRYGSSA-N Loganic acid Natural products CC[C@H]1O[C@@H](O[C@@H]2OC=C([C@H]3C[C@H](O)[C@H](C)[C@@H]23)C(=O)O)[C@H](O)[C@@H](O)[C@@H]1O WMQIBEYREGDWOS-UOUCRYGSSA-N 0.000 claims description 4
- UBAIOTDKPLIEDD-ZHZVUFEGSA-N Procumbide Natural products O([C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1)[C@@H]1OC=C[C@]2(O)[C@@H](O)[C@H]3[C@](C)(O3)[C@@H]12 UBAIOTDKPLIEDD-ZHZVUFEGSA-N 0.000 claims description 4
- WSGPLSDARZNMCW-LPGRTNKPSA-N Scandoside methyl ester Chemical compound O([C@@H]1OC=C([C@@H]2[C@H]1C(=C[C@H]2O)CO)C(=O)OC)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O WSGPLSDARZNMCW-LPGRTNKPSA-N 0.000 claims description 4
- CSKKDSFETGLMSB-FUJZYWHJSA-N Secologanin Natural products C=C[C@@H]1[C@H](CC=O)C(C(=O)OC)=CO[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CSKKDSFETGLMSB-FUJZYWHJSA-N 0.000 claims description 4
- VSJGJMKGNMDJCI-ZASXJUAOSA-N Sweroside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@H]1[C@H](C=C)[C@H](CCOC2=O)C2=CO1 VSJGJMKGNMDJCI-ZASXJUAOSA-N 0.000 claims description 4
- HEYZWPRKKUGDCR-QBXMEVCASA-N Swertiamarin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@H]1[C@H](C=C)[C@]2(O)CCOC(=O)C2=CO1 HEYZWPRKKUGDCR-QBXMEVCASA-N 0.000 claims description 4
- HEYZWPRKKUGDCR-WRMJXEAJSA-N Swertiamarin Natural products O([C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1)[C@H]1[C@@H](C=C)[C@@]2(O)C(C(=O)OCC2)=CO1 HEYZWPRKKUGDCR-WRMJXEAJSA-N 0.000 claims description 4
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- RJWJHRPNHPHBRN-FKVJWERZSA-N aucubin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@H]1[C@@H]2C(CO)=C[C@@H](O)[C@@H]2C=CO1 RJWJHRPNHPHBRN-FKVJWERZSA-N 0.000 claims description 4
- LHDWRKICQLTVDL-PZYDOOQISA-N catalpol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@H]1[C@@H]2[C@@]3(CO)O[C@H]3[C@@H](O)[C@@H]2C=CO1 LHDWRKICQLTVDL-PZYDOOQISA-N 0.000 claims description 4
- UXSACQOOWZMGSE-UHFFFAOYSA-N catalposide Natural products OC1C(O)C(O)C(CO)OC1OC1C2C3(CO)OC3C(OC(=O)C=3C=CC(O)=CC=3)C2C=CO1 UXSACQOOWZMGSE-UHFFFAOYSA-N 0.000 claims description 4
- ZVXWFPTVHBWJOU-YYFGDFGFSA-N deacetylasperulosidic acid Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@H]1[C@@H]2C(CO)=C[C@H](O)[C@@H]2C(C(O)=O)=CO1 ZVXWFPTVHBWJOU-YYFGDFGFSA-N 0.000 claims description 4
- QWEKFUBDXQTUTJ-LRPGRGPISA-N demethyloleuropein Chemical compound O([C@H]1C([C@@H](C(=CO1)C(O)=O)CC(=O)OC=CC=1C=C(O)C(O)=CC=1)=CC)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O QWEKFUBDXQTUTJ-LRPGRGPISA-N 0.000 claims description 4
- JNNGEAWILNVFFD-UHFFFAOYSA-N epiloganic acid Natural products CC1C(O)CC(C(=CO2)C(O)=O)C1C2OC1OC(CO)C(O)C(O)C1O JNNGEAWILNVFFD-UHFFFAOYSA-N 0.000 claims description 4
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- 150000002431 hydrogen Chemical class 0.000 claims description 4
- WTYCACYRVDPVSW-UHFFFAOYSA-N hydroxyframoside A Natural products CC=C/1C(OC2OC(CO)C(O)C(O)C2O)OC=C(C1CC(=O)OCCc3ccc(O)c(O)c3)C(=O)OCCc4ccc(O)cc4 WTYCACYRVDPVSW-UHFFFAOYSA-N 0.000 claims description 4
- WCVNZUFLGOZCHB-UHFFFAOYSA-N hydroxyframoside B Natural products CC=C/1C(OC2OC(CO)C(O)C(O)C2O)OC=C(C1CC(=O)OCCc3ccc(O)cc3)C(=O)OCCc4ccc(O)c(O)c4 WCVNZUFLGOZCHB-UHFFFAOYSA-N 0.000 claims description 4
- GMQXOLRKJQWPNB-MVVLSVRYSA-N ligstroside Chemical compound O([C@@H]\1OC=C([C@H](C/1=C\C)CC(=O)OCCC=1C=CC(O)=CC=1)C(=O)OC)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O GMQXOLRKJQWPNB-MVVLSVRYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- XJMPAUZQVRGFRE-AYDWLWLASA-N methyl (1s,4as,7s,7as)-7-hydroxy-7-(hydroxymethyl)-1-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,7a-dihydro-1h-cyclopenta[c]pyran-4-carboxylate Chemical compound O([C@@H]1OC=C([C@@H]2[C@H]1[C@](C=C2)(O)CO)C(=O)OC)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O XJMPAUZQVRGFRE-AYDWLWLASA-N 0.000 claims description 4
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 1
- SAHIZENKTPRYSN-UHFFFAOYSA-N [2-[3-(phenoxymethyl)phenoxy]-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound O(C1=CC=CC=C1)CC=1C=C(OC2=NC(=CC(=C2)CN)C(F)(F)F)C=CC=1 SAHIZENKTPRYSN-UHFFFAOYSA-N 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 229940095054 ammoniac Drugs 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 235000019606 astringent taste Nutrition 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- OIQPTROHQCGFEF-UHFFFAOYSA-L chembl1371409 Chemical compound [Na+].[Na+].OC1=CC=C2C=C(S([O-])(=O)=O)C=CC2=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 OIQPTROHQCGFEF-UHFFFAOYSA-L 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229920002770 condensed tannin Polymers 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- DGODWNOPHMXOTR-UHFFFAOYSA-N dipotassium;dioxido(dioxo)osmium;dihydrate Chemical compound O.O.[K+].[K+].[O-][Os]([O-])(=O)=O DGODWNOPHMXOTR-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 235000002864 food coloring agent Nutrition 0.000 description 1
- 239000000576 food coloring agent Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000005980 hexynyl group Chemical group 0.000 description 1
- 229920001461 hydrolysable tannin Polymers 0.000 description 1
- 239000000413 hydrolysate Substances 0.000 description 1
- 230000033444 hydroxylation Effects 0.000 description 1
- 238000005805 hydroxylation reaction Methods 0.000 description 1
- UWYVPFMHMJIBHE-OWOJBTEDSA-N hydroxymaleic acid group Chemical group O/C(/C(=O)O)=C/C(=O)O UWYVPFMHMJIBHE-OWOJBTEDSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 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
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000002121 nanofiber Substances 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000006174 pH buffer Substances 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
- 125000005981 pentynyl group Chemical group 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical compound C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000003259 recombinant expression Methods 0.000 description 1
- 238000010188 recombinant method Methods 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 230000001953 sensory effect Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 235000011083 sodium citrates Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- BYGOPQKDHGXNCD-UHFFFAOYSA-N tripotassium;iron(3+);hexacyanide Chemical compound [K+].[K+].[K+].[Fe+3].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] BYGOPQKDHGXNCD-UHFFFAOYSA-N 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C14—SKINS; HIDES; PELTS; LEATHER
- C14C—CHEMICAL TREATMENT OF HIDES, SKINS OR LEATHER, e.g. TANNING, IMPREGNATING, FINISHING; APPARATUS THEREFOR; COMPOSITIONS FOR TANNING
- C14C3/00—Tanning; Compositions for tanning
- C14C3/02—Chemical tanning
- C14C3/08—Chemical tanning by organic agents
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Saccharide Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP22306770.3A EP4379068A1 (fr) | 2022-12-01 | 2022-12-01 | Dérivés iridoïdes ou séco-iridoïdes et leur utilisation dans un procédé de tannage |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP22306770.3A EP4379068A1 (fr) | 2022-12-01 | 2022-12-01 | Dérivés iridoïdes ou séco-iridoïdes et leur utilisation dans un procédé de tannage |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP4379068A1 true EP4379068A1 (fr) | 2024-06-05 |
Family
ID=84537488
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP22306770.3A Pending EP4379068A1 (fr) | 2022-12-01 | 2022-12-01 | Dérivés iridoïdes ou séco-iridoïdes et leur utilisation dans un procédé de tannage |
Country Status (1)
| Country | Link |
|---|---|
| EP (1) | EP4379068A1 (fr) |
Citations (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6428978B1 (en) | 1998-05-08 | 2002-08-06 | Cohesion Technologies, Inc. | Methods for the production of gelatin and full-length triple helical collagen in recombinant cells |
| EP1232182A2 (fr) | 1999-11-12 | 2002-08-21 | Fibrogen, Inc. | Collagenes et gelatines animaux |
| WO2009065915A1 (fr) | 2007-11-23 | 2009-05-28 | N-Zyme Biotec Gmbh | Agent et procédé de tannage de peaux et de cuirs |
| US8188230B2 (en) | 1997-12-24 | 2012-05-29 | Fuji Film Manufacturing Europe B.V. | Method for recombinant microorganism expression and isolation of collagen-like polypeptides |
| CN102925508A (zh) * | 2011-08-10 | 2013-02-13 | 浙江毕尔锐思生物技术股份有限公司 | 一种制备环烯醚萜甙元的方法 |
| US20170080040A1 (en) * | 2014-05-15 | 2017-03-23 | Livio Pesle | Decoction of olive leaves |
| WO2018025210A1 (fr) * | 2016-08-03 | 2018-02-08 | Tannow S.R.L. | Utilisation d'eaux usées de moulins à olives dans l'industrie du tannage du cuir |
| US20190002893A1 (en) | 2017-06-29 | 2019-01-03 | Modern Meadow, Inc. | Yeast strains and methods for producing collagen |
| US20190040400A1 (en) | 2017-07-31 | 2019-02-07 | Modern Meadow, Inc. | Yeast strains and methods for controlling hydroxylation of recombinant collagen |
| US20190092838A1 (en) | 2017-09-22 | 2019-03-28 | Modern Meadow, Inc. | Recombinant yeast strains |
-
2022
- 2022-12-01 EP EP22306770.3A patent/EP4379068A1/fr active Pending
Patent Citations (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8188230B2 (en) | 1997-12-24 | 2012-05-29 | Fuji Film Manufacturing Europe B.V. | Method for recombinant microorganism expression and isolation of collagen-like polypeptides |
| US6428978B1 (en) | 1998-05-08 | 2002-08-06 | Cohesion Technologies, Inc. | Methods for the production of gelatin and full-length triple helical collagen in recombinant cells |
| EP1232182A2 (fr) | 1999-11-12 | 2002-08-21 | Fibrogen, Inc. | Collagenes et gelatines animaux |
| WO2009065915A1 (fr) | 2007-11-23 | 2009-05-28 | N-Zyme Biotec Gmbh | Agent et procédé de tannage de peaux et de cuirs |
| CN102925508A (zh) * | 2011-08-10 | 2013-02-13 | 浙江毕尔锐思生物技术股份有限公司 | 一种制备环烯醚萜甙元的方法 |
| US20170080040A1 (en) * | 2014-05-15 | 2017-03-23 | Livio Pesle | Decoction of olive leaves |
| WO2018025210A1 (fr) * | 2016-08-03 | 2018-02-08 | Tannow S.R.L. | Utilisation d'eaux usées de moulins à olives dans l'industrie du tannage du cuir |
| US20190002893A1 (en) | 2017-06-29 | 2019-01-03 | Modern Meadow, Inc. | Yeast strains and methods for producing collagen |
| US20190040400A1 (en) | 2017-07-31 | 2019-02-07 | Modern Meadow, Inc. | Yeast strains and methods for controlling hydroxylation of recombinant collagen |
| US20190092838A1 (en) | 2017-09-22 | 2019-03-28 | Modern Meadow, Inc. | Recombinant yeast strains |
| US20190093116A1 (en) | 2017-09-22 | 2019-03-28 | Modern Meadow, Inc. | Recombinant yeast strains |
Non-Patent Citations (3)
| Title |
|---|
| DING ET AL., JALCA, vol. 103, 2008, pages 377 |
| TAYLOR ET AL., JALCA, vol. 104, 2009, pages 79 |
| ZHANG ET AL., JALCA, vol. 106, 2011, pages 121 |
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