JP2020528446A - 新規なバニリン及び/又はエチルバニリン、それらの調製方法、並びにそれらの使用 - Google Patents
新規なバニリン及び/又はエチルバニリン、それらの調製方法、並びにそれらの使用 Download PDFInfo
- Publication number
- JP2020528446A JP2020528446A JP2020504399A JP2020504399A JP2020528446A JP 2020528446 A JP2020528446 A JP 2020528446A JP 2020504399 A JP2020504399 A JP 2020504399A JP 2020504399 A JP2020504399 A JP 2020504399A JP 2020528446 A JP2020528446 A JP 2020528446A
- Authority
- JP
- Japan
- Prior art keywords
- hydroxy
- ppm
- ethoxy
- vanillin
- ethylvanillin
- 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
- CBOQJANXLMLOSS-UHFFFAOYSA-N ethyl vanillin Chemical compound CCOC1=CC(C=O)=CC=C1O CBOQJANXLMLOSS-UHFFFAOYSA-N 0.000 title claims abstract description 120
- 235000012141 vanillin Nutrition 0.000 title claims abstract description 88
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 title claims abstract description 87
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 title claims abstract description 87
- 229940073505 ethyl vanillin Drugs 0.000 title claims abstract description 60
- 150000001875 compounds Chemical class 0.000 claims abstract description 46
- 238000000034 method Methods 0.000 claims abstract description 34
- 239000012535 impurity Substances 0.000 claims abstract description 26
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 claims description 103
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 claims description 100
- 229960001867 guaiacol Drugs 0.000 claims description 51
- 229910052799 carbon Inorganic materials 0.000 claims description 44
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 43
- 239000000203 mixture Substances 0.000 claims description 30
- JJVNINGBHGBWJH-UHFFFAOYSA-N ortho-vanillin Chemical compound COC1=CC=CC(C=O)=C1O JJVNINGBHGBWJH-UHFFFAOYSA-N 0.000 claims description 24
- -1 3-ethoxy-4-hydroxybenzylidene Chemical group 0.000 claims description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 18
- YOIZTLBZAMFVPK-UHFFFAOYSA-N 2-(3-ethoxy-4-hydroxyphenyl)-2-hydroxyacetic acid Chemical compound CCOC1=CC(C(O)C(O)=O)=CC=C1O YOIZTLBZAMFVPK-UHFFFAOYSA-N 0.000 claims description 12
- OYDHUFAKOQMOAB-UHFFFAOYSA-N 2-[3-[carboxy(hydroxy)methyl]-4-hydroxy-5-methoxyphenyl]-2-hydroxyacetic acid Chemical compound COC1=CC(C(O)C(O)=O)=CC(C(O)C(O)=O)=C1O OYDHUFAKOQMOAB-UHFFFAOYSA-N 0.000 claims description 12
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 12
- OFQBYHLLIJGMNP-UHFFFAOYSA-N 3-ethoxy-2-hydroxybenzaldehyde Chemical compound CCOC1=CC=CC(C=O)=C1O OFQBYHLLIJGMNP-UHFFFAOYSA-N 0.000 claims description 11
- UYGBSRJODQHNLQ-UHFFFAOYSA-N 4-hydroxy-3,5-dimethylbenzaldehyde Chemical compound CC1=CC(C=O)=CC(C)=C1O UYGBSRJODQHNLQ-UHFFFAOYSA-N 0.000 claims description 11
- WQWNVPGJVKVZDH-UHFFFAOYSA-N 5-ethoxy-4-hydroxybenzene-1,3-dicarbaldehyde Chemical compound CCOC1=CC(C=O)=CC(C=O)=C1O WQWNVPGJVKVZDH-UHFFFAOYSA-N 0.000 claims description 11
- 238000009833 condensation Methods 0.000 claims description 11
- 230000005494 condensation Effects 0.000 claims description 11
- BAKYASSDAXQKKY-UHFFFAOYSA-N 4-Hydroxy-3-methylbenzaldehyde Chemical compound CC1=CC(C=O)=CC=C1O BAKYASSDAXQKKY-UHFFFAOYSA-N 0.000 claims description 10
- CGQCWMIAEPEHNQ-UHFFFAOYSA-N Vanillylmandelic acid Chemical compound COC1=CC(C(O)C(O)=O)=CC=C1O CGQCWMIAEPEHNQ-UHFFFAOYSA-N 0.000 claims description 10
- 229920005610 lignin Polymers 0.000 claims description 9
- NIIZBVLLTZEREW-UHFFFAOYSA-N 2-(3-ethoxy-2-hydroxyphenyl)-2-hydroxyacetic acid Chemical compound CCOC1=CC=CC(C(O)C(O)=O)=C1O NIIZBVLLTZEREW-UHFFFAOYSA-N 0.000 claims description 8
- YVNRFQCFZVYDRO-UHFFFAOYSA-N 4-hydroxy-5-methoxybenzene-1,3-dicarbaldehyde Chemical compound COC1=CC(C=O)=CC(C=O)=C1O YVNRFQCFZVYDRO-UHFFFAOYSA-N 0.000 claims description 8
- 239000002028 Biomass Substances 0.000 claims description 7
- 239000007859 condensation product Substances 0.000 claims description 7
- RRIGSMWVFMHZQR-UHFFFAOYSA-N 2-[3-[carboxy(hydroxy)methyl]-5-ethoxy-4-hydroxyphenyl]-2-hydroxyacetic acid Chemical compound CCOc1cc(cc(C(O)C(O)=O)c1O)C(O)C(O)=O RRIGSMWVFMHZQR-UHFFFAOYSA-N 0.000 claims description 6
- SYMPFBURZFGXAS-UHFFFAOYSA-N 2-hydroxy-2-(2-hydroxy-3-methoxyphenyl)acetic acid Chemical compound COC1=CC=CC(C(O)C(O)=O)=C1O SYMPFBURZFGXAS-UHFFFAOYSA-N 0.000 claims description 6
- 239000000796 flavoring agent Substances 0.000 claims description 6
- 235000019634 flavors Nutrition 0.000 claims description 6
- 235000013305 food Nutrition 0.000 claims description 6
- 239000003205 fragrance Substances 0.000 claims description 6
- 239000002537 cosmetic Substances 0.000 claims description 5
- 230000001590 oxidative effect Effects 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 239000011324 bead Substances 0.000 claims description 4
- 235000013361 beverage Nutrition 0.000 claims description 4
- 239000000843 powder Substances 0.000 claims description 4
- 230000001953 sensory effect Effects 0.000 claims description 4
- IZALUMVGBVKPJD-UHFFFAOYSA-N benzene-1,3-dicarbaldehyde Chemical compound O=CC1=CC=CC(C=O)=C1 IZALUMVGBVKPJD-UHFFFAOYSA-N 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- WEVFUSSJCGAVOH-UHFFFAOYSA-N 2,3-dihydro-1-benzofuran-2-carboxylic acid Chemical compound C1=CC=C2OC(C(=O)O)CC2=C1 WEVFUSSJCGAVOH-UHFFFAOYSA-N 0.000 claims description 2
- UIFVCPMLQXKEEU-UHFFFAOYSA-N 2,3-dimethylbenzaldehyde Chemical compound CC1=CC=CC(C=O)=C1C UIFVCPMLQXKEEU-UHFFFAOYSA-N 0.000 claims description 2
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 2
- ACZGCWSMSTYWDQ-UHFFFAOYSA-N 3h-1-benzofuran-2-one Chemical compound C1=CC=C2OC(=O)CC2=C1 ACZGCWSMSTYWDQ-UHFFFAOYSA-N 0.000 claims description 2
- 150000001299 aldehydes Chemical class 0.000 claims description 2
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 238000010586 diagram Methods 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 25
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 18
- 241000196324 Embryophyta Species 0.000 description 16
- 238000007254 oxidation reaction Methods 0.000 description 13
- 239000007864 aqueous solution Substances 0.000 description 12
- 238000006482 condensation reaction Methods 0.000 description 10
- 230000008569 process Effects 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 8
- XLJKHNWPARRRJB-UHFFFAOYSA-N cobalt(2+) Chemical compound [Co+2] XLJKHNWPARRRJB-UHFFFAOYSA-N 0.000 description 8
- 229910052742 iron Inorganic materials 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 7
- 230000003647 oxidation Effects 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- 244000263375 Vanilla tahitensis Species 0.000 description 6
- 235000012036 Vanilla tahitensis Nutrition 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 230000000243 photosynthetic effect Effects 0.000 description 6
- 239000012429 reaction media Substances 0.000 description 6
- KSEBMYQBYZTDHS-HWKANZROSA-M (E)-Ferulic acid Natural products COC1=CC(\C=C\C([O-])=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-M 0.000 description 5
- 240000007594 Oryza sativa Species 0.000 description 5
- 235000007164 Oryza sativa Nutrition 0.000 description 5
- 235000009499 Vanilla fragrans Nutrition 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 229910017052 cobalt Inorganic materials 0.000 description 5
- 239000010941 cobalt Substances 0.000 description 5
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 5
- JAWGVVJVYSANRY-UHFFFAOYSA-N cobalt(3+) Chemical compound [Co+3] JAWGVVJVYSANRY-UHFFFAOYSA-N 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- KSEBMYQBYZTDHS-UHFFFAOYSA-N ferulic acid Natural products COC1=CC(C=CC(O)=O)=CC=C1O KSEBMYQBYZTDHS-UHFFFAOYSA-N 0.000 description 5
- 235000001785 ferulic acid Nutrition 0.000 description 5
- KSEBMYQBYZTDHS-HWKANZROSA-N ferulic acid Chemical compound COC1=CC(\C=C\C(O)=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-N 0.000 description 5
- 229940114124 ferulic acid Drugs 0.000 description 5
- 230000004060 metabolic process Effects 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 235000009566 rice Nutrition 0.000 description 5
- QURCVMIEKCOAJU-UHFFFAOYSA-N trans-isoferulic acid Natural products COC1=CC=C(C=CC(O)=O)C=C1O QURCVMIEKCOAJU-UHFFFAOYSA-N 0.000 description 5
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 4
- VEQPNABPJHWNSG-UHFFFAOYSA-N Nickel(2+) Chemical compound [Ni+2] VEQPNABPJHWNSG-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 4
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 4
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 4
- 230000000155 isotopic effect Effects 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- AUZQQIPZESHNMG-UHFFFAOYSA-N 3-methoxysalicylic acid Chemical compound COC1=CC=CC(C(O)=O)=C1O AUZQQIPZESHNMG-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 244000046052 Phaseolus vulgaris Species 0.000 description 3
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 240000008042 Zea mays Species 0.000 description 3
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 3
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 3
- 239000012736 aqueous medium Substances 0.000 description 3
- 150000001491 aromatic compounds Chemical class 0.000 description 3
- 230000036983 biotransformation Effects 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 235000005822 corn Nutrition 0.000 description 3
- 229960002510 mandelic acid Drugs 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 244000005700 microbiome Species 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 0 COc1c(*)cccc1 Chemical compound COc1c(*)cccc1 0.000 description 2
- OKTJSMMVPCPJKN-NJFSPNSNSA-N Carbon-14 Chemical compound [14C] OKTJSMMVPCPJKN-NJFSPNSNSA-N 0.000 description 2
- 229910021581 Cobalt(III) chloride Inorganic materials 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- JJLJMEJHUUYSSY-UHFFFAOYSA-L Copper hydroxide Chemical compound [OH-].[OH-].[Cu+2] JJLJMEJHUUYSSY-UHFFFAOYSA-L 0.000 description 2
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 2
- 235000011613 Pinus brutia Nutrition 0.000 description 2
- 241000018646 Pinus brutia Species 0.000 description 2
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 2
- 241001125048 Sardina Species 0.000 description 2
- 238000004760 accelerator mass spectrometry Methods 0.000 description 2
- 150000001242 acetic acid derivatives Chemical class 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000003851 biochemical process Effects 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- IRAQOCYXUMOFCW-OSFYFWSMSA-N cedr-8-ene Chemical compound C1[C@]23[C@H](C)CC[C@H]3C(C)(C)[C@@H]1C(C)=CC2 IRAQOCYXUMOFCW-OSFYFWSMSA-N 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
- QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 description 2
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 238000000855 fermentation Methods 0.000 description 2
- 230000004151 fermentation Effects 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 239000004312 hexamethylene tetramine Substances 0.000 description 2
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 2
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 238000004811 liquid chromatography Methods 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 2
- 238000004949 mass spectrometry Methods 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229930014626 natural product Natural products 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- MOOYVEVEDVVKGD-UHFFFAOYSA-N oxaldehydic acid;hydrate Chemical compound O.OC(=O)C=O MOOYVEVEDVVKGD-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- 230000020477 pH reduction Effects 0.000 description 2
- 230000037361 pathway Effects 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 238000012552 review Methods 0.000 description 2
- 235000019512 sardine Nutrition 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000007655 standard test method Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- IEKWPPTXWFKANS-UHFFFAOYSA-K trichlorocobalt Chemical compound Cl[Co](Cl)Cl IEKWPPTXWFKANS-UHFFFAOYSA-K 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- CGQCWMIAEPEHNQ-UHFFFAOYSA-M vanillylmandelate Chemical compound COC1=CC(C(O)C([O-])=O)=CC=C1O CGQCWMIAEPEHNQ-UHFFFAOYSA-M 0.000 description 2
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- LFKXWKGYHQXRQA-FDGPNNRMSA-N (z)-4-hydroxypent-3-en-2-one;iron Chemical compound [Fe].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O LFKXWKGYHQXRQA-FDGPNNRMSA-N 0.000 description 1
- DSXKMMAQDSAZAC-UHFFFAOYSA-N 2-hydroxy-3,5-dimethylbenzaldehyde Chemical compound CC1=CC(C)=C(O)C(C=O)=C1 DSXKMMAQDSAZAC-UHFFFAOYSA-N 0.000 description 1
- WBHAUHHMPXBZCQ-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound COC1=CC=CC(C)=C1O WBHAUHHMPXBZCQ-UHFFFAOYSA-N 0.000 description 1
- UCSQZOJYEKEZID-UHFFFAOYSA-N 2-methoxybenzene-1,3-dicarbaldehyde Chemical compound COC1=C(C=O)C=CC=C1C=O UCSQZOJYEKEZID-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- MWOOGOJBHIARFG-OUBTZVSYSA-N 4-hydroxy-3-methoxybenzaldehyde Chemical group [13CH3]OC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-OUBTZVSYSA-N 0.000 description 1
- YHXHKYRQLYQUIH-UHFFFAOYSA-N 4-hydroxymandelic acid Chemical compound OC(=O)C(O)C1=CC=C(O)C=C1 YHXHKYRQLYQUIH-UHFFFAOYSA-N 0.000 description 1
- 244000144725 Amygdalus communis Species 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- OADIQUIWSQCIOE-UHFFFAOYSA-N C(C)(=O)CC(C)=O.[Cu+3] Chemical compound C(C)(=O)CC(C)=O.[Cu+3] OADIQUIWSQCIOE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-OUBTZVSYSA-N Carbon-13 Chemical compound [13C] OKTJSMMVPCPJKN-OUBTZVSYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 description 1
- 229910021580 Cobalt(II) chloride Inorganic materials 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- 239000005749 Copper compound Substances 0.000 description 1
- 229910021589 Copper(I) bromide Inorganic materials 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 1
- 229910021590 Copper(II) bromide Inorganic materials 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical group COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 239000005770 Eugenol Substances 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound 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
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 241000233855 Orchidaceae Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- UVMRYBDEERADNV-UHFFFAOYSA-N Pseudoeugenol Natural products COC1=CC(C(C)=C)=CC=C1O UVMRYBDEERADNV-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- 244000030973 Vanilla pompona Species 0.000 description 1
- 235000016424 Vanilla pompona Nutrition 0.000 description 1
- 239000012773 agricultural material Substances 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000006696 biosynthetic metabolic pathway Effects 0.000 description 1
- 125000005587 carbonate group Chemical group 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 1
- UFMZWBIQTDUYBN-UHFFFAOYSA-N cobalt dinitrate Chemical compound [Co+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O UFMZWBIQTDUYBN-UHFFFAOYSA-N 0.000 description 1
- 229910001981 cobalt nitrate Inorganic materials 0.000 description 1
- ZOTKGJBKKKVBJZ-UHFFFAOYSA-L cobalt(2+);carbonate Chemical compound [Co+2].[O-]C([O-])=O ZOTKGJBKKKVBJZ-UHFFFAOYSA-L 0.000 description 1
- OBWXQDHWLMJOOD-UHFFFAOYSA-H cobalt(2+);dicarbonate;dihydroxide;hydrate Chemical compound O.[OH-].[OH-].[Co+2].[Co+2].[Co+2].[O-]C([O-])=O.[O-]C([O-])=O OBWXQDHWLMJOOD-UHFFFAOYSA-H 0.000 description 1
- OOMOMODKLPLOKW-UHFFFAOYSA-H cobalt(3+);trisulfate Chemical compound [Co+3].[Co+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O OOMOMODKLPLOKW-UHFFFAOYSA-H 0.000 description 1
- 229910000001 cobalt(II) carbonate Inorganic materials 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 238000004320 controlled atmosphere Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000001880 copper compounds Chemical class 0.000 description 1
- RFKZUAOAYVHBOY-UHFFFAOYSA-M copper(1+);acetate Chemical compound [Cu+].CC([O-])=O RFKZUAOAYVHBOY-UHFFFAOYSA-M 0.000 description 1
- RPJAQOVNRDOGAY-UHFFFAOYSA-L copper(1+);sulfite Chemical compound [Cu+].[Cu+].[O-]S([O-])=O RPJAQOVNRDOGAY-UHFFFAOYSA-L 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- BERDEBHAJNAUOM-UHFFFAOYSA-N copper(I) oxide Inorganic materials [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 229910000366 copper(II) sulfate Inorganic materials 0.000 description 1
- NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 1
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
- WIVXEZIMDUGYRW-UHFFFAOYSA-L copper(i) sulfate Chemical compound [Cu+].[Cu+].[O-]S([O-])(=O)=O WIVXEZIMDUGYRW-UHFFFAOYSA-L 0.000 description 1
- JBAKCAZIROEXGK-LNKPDPKZSA-N copper;(z)-4-hydroxypent-3-en-2-one Chemical compound [Cu].C\C(O)=C\C(C)=O JBAKCAZIROEXGK-LNKPDPKZSA-N 0.000 description 1
- ZKXWKVVCCTZOLD-FDGPNNRMSA-N copper;(z)-4-hydroxypent-3-en-2-one Chemical compound [Cu].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O ZKXWKVVCCTZOLD-FDGPNNRMSA-N 0.000 description 1
- UFKUWSBTKLUIIZ-UHFFFAOYSA-N copper;pentane-2,4-dione Chemical compound [Cu+2].CC(=O)CC(C)=O UFKUWSBTKLUIIZ-UHFFFAOYSA-N 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 229940076286 cupric acetate Drugs 0.000 description 1
- 229960003280 cupric chloride Drugs 0.000 description 1
- 229960004643 cupric oxide Drugs 0.000 description 1
- 229940045803 cuprous chloride Drugs 0.000 description 1
- KRFJLUBVMFXRPN-UHFFFAOYSA-N cuprous oxide Chemical compound [O-2].[Cu+].[Cu+] KRFJLUBVMFXRPN-UHFFFAOYSA-N 0.000 description 1
- 229940112669 cuprous oxide Drugs 0.000 description 1
- JRTIUDXYIUKIIE-UHFFFAOYSA-N cycloocta-1,5-diene;nickel Chemical compound [Ni].C1CC=CCCC=C1.C1CC=CCCC=C1 JRTIUDXYIUKIIE-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- IRAQOCYXUMOFCW-UHFFFAOYSA-N di-epi-alpha-cedrene Natural products C1C23C(C)CCC3C(C)(C)C1C(C)=CC2 IRAQOCYXUMOFCW-UHFFFAOYSA-N 0.000 description 1
- ZMMDPCMYTCRWFF-UHFFFAOYSA-J dicopper;carbonate;dihydroxide Chemical compound [OH-].[OH-].[Cu+2].[Cu+2].[O-]C([O-])=O ZMMDPCMYTCRWFF-UHFFFAOYSA-J 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- DBPFRRFGLYGEJI-UHFFFAOYSA-N ethyl glyoxylate Chemical compound CCOC(=O)C=O DBPFRRFGLYGEJI-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- UPCIBFUJJLCOQG-UHFFFAOYSA-L ethyl-[2-[2-[ethyl(dimethyl)azaniumyl]ethyl-methylamino]ethyl]-dimethylazanium;dibromide Chemical compound [Br-].[Br-].CC[N+](C)(C)CCN(C)CC[N+](C)(C)CC UPCIBFUJJLCOQG-UHFFFAOYSA-L 0.000 description 1
- 229960002217 eugenol Drugs 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- FVIZARNDLVOMSU-UHFFFAOYSA-N ginsenoside K Natural products C1CC(C2(CCC3C(C)(C)C(O)CCC3(C)C2CC2O)C)(C)C2C1C(C)(CCC=C(C)C)OC1OC(CO)C(O)C(O)C1O FVIZARNDLVOMSU-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- AMWUFXLSROXQFP-UHFFFAOYSA-N iron(3+);pentane-2,4-dione Chemical compound [Fe+3].CC(=O)CC(C)=O AMWUFXLSROXQFP-UHFFFAOYSA-N 0.000 description 1
- PVFSDGKDKFSOTB-UHFFFAOYSA-K iron(3+);triacetate Chemical compound [Fe+3].CC([O-])=O.CC([O-])=O.CC([O-])=O PVFSDGKDKFSOTB-UHFFFAOYSA-K 0.000 description 1
- LNOZJRCUHSPCDZ-UHFFFAOYSA-L iron(ii) acetate Chemical compound [Fe+2].CC([O-])=O.CC([O-])=O LNOZJRCUHSPCDZ-UHFFFAOYSA-L 0.000 description 1
- LZKLAOYSENRNKR-LNTINUHCSA-N iron;(z)-4-oxoniumylidenepent-2-en-2-olate Chemical compound [Fe].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O LZKLAOYSENRNKR-LNTINUHCSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- KFKXSMSQHIOMSO-UHFFFAOYSA-N methyl 2-oxoacetate Chemical compound COC(=O)C=O KFKXSMSQHIOMSO-UHFFFAOYSA-N 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 230000002906 microbiologic effect Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
- 239000006225 natural substrate Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000002815 nickel Chemical class 0.000 description 1
- LGQLOGILCSXPEA-UHFFFAOYSA-L nickel sulfate Chemical compound [Ni+2].[O-]S([O-])(=O)=O LGQLOGILCSXPEA-UHFFFAOYSA-L 0.000 description 1
- BMGNSKKZFQMGDH-FDGPNNRMSA-L nickel(2+);(z)-4-oxopent-2-en-2-olate Chemical compound [Ni+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O BMGNSKKZFQMGDH-FDGPNNRMSA-L 0.000 description 1
- 229910000008 nickel(II) carbonate Inorganic materials 0.000 description 1
- 229910000363 nickel(II) sulfate Inorganic materials 0.000 description 1
- ZULUUIKRFGGGTL-UHFFFAOYSA-L nickel(ii) carbonate Chemical compound [Ni+2].[O-]C([O-])=O ZULUUIKRFGGGTL-UHFFFAOYSA-L 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001706 oxygenating effect Effects 0.000 description 1
- 230000029553 photosynthesis Effects 0.000 description 1
- 238000010672 photosynthesis Methods 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- JQWYTSHFVIDUHA-UHFFFAOYSA-M sodium;2-hydroxy-3-methoxybenzoate Chemical compound [Na+].COC1=CC=CC(C([O-])=O)=C1O JQWYTSHFVIDUHA-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- DKZBBWMURDFHNE-UHFFFAOYSA-N trans-coniferylaldehyde Natural products COC1=CC(C=CC=O)=CC=C1O DKZBBWMURDFHNE-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
- C07C47/575—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing ether groups, groups, groups, or groups
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
- A23L2/52—Adding ingredients
- A23L2/56—Flavouring or bittering agents
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/10—Natural spices, flavouring agents or condiments; Extracts thereof
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/204—Aromatic compounds
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/24—Synthetic spices, flavouring agents or condiments prepared by fermentation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/455—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation with carboxylic acids or their derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/54—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of compounds containing doubly bound oxygen atoms, e.g. esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
- C07C47/575—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing ether groups, groups, groups, or groups
- C07C47/58—Vanillin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/367—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in singly bound form
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/373—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in doubly bound form
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
- C07D307/83—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0061—Essential oils; Perfumes compounds containing a six-membered aromatic ring not condensed with another ring
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0069—Heterocyclic compounds
- C11B9/0073—Heterocyclic compounds containing only O or S as heteroatoms
- C11B9/0076—Heterocyclic compounds containing only O or S as heteroatoms the hetero rings containing less than six atoms
-
- 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
Abstract
Description
− バイオベース炭素の含有率が75%〜100%であるバニリン及び/又はエチルバニリン;並びに
− 2−ヒドロキシ−2−(4−ヒドロキシ−3−メトキシフェニル)酢酸、4−ヒドロキシ−5−メトキシイソフタルアルデヒド、2,2’−(4−ヒドロキシ−5−メトキシ−1,3−フェニレン)ビス(2−ヒドロキシ酢酸)、2−ヒドロキシ−3−メトキシベンズアルデヒド、2−ヒドロキシ−2−(2−ヒドロキシ−3−メトキシフェニル)酢酸、2−(3−エトキシ−4−ヒドロキシフェニル)−2−ヒドロキシ酢酸、2−(3−エトキシ−2−ヒドロキシフェニル)−2−ヒドロキシ酢酸、2,2’−(5−エトキシ−4−ヒドロキシ−1,3−フェニレン)ビス(2−ヒドロキシ酢酸)、5−エトキシ−4−ヒドロキシイソフタルアルデヒド、3−エトキシ−2−ヒドロキシベンズアルデヒド、(E又はZ)−3−(4−ヒドロキシ−3−メトキシベンジリデン)−7−メトキシベンゾフラン−2(3H)−オン、(E又はZ)−7−エトキシ−3−(3−エトキシ−4−ヒドロキシベンジリデン)ベンゾフラン−2(3H)−オン、4−ヒドロキシ−3−メチルベンズアルデヒド、及び4−ヒドロキシ−3,5−ジメチルベンズアルデヒドからなる群から選択される、不純物と呼ばれる場合がある少なくとも1つの化合物;
を含有するか、又は本質的にこれらからなる、組成物に関する。
別の態様では、本発明は:
− バイオベース炭素の含有率が75%〜100%であるグアイアコール及び/又はグエトールとグリオキシル酸とを縮合する工程(a);並びに
− 得られた縮合生成物を酸化する工程(b);
を含む、バイオベース炭素の含有率が75%〜100%であるバニリン及び/又はエチルバニリンの調製方法に関する。
− 有機溶媒を用いて抽出することにより反応混合物からバニリン及び/又はエチルバニリンを分離すること;及び
− 抽出に使用した有機溶媒を回収及びリサイクルすること;
を含む。
− バイオベース炭素の含有率が100%の天然由来のグアイアコール、特にクレゾール(オルト、メタ、パラ)及び2,6−ジメチルフェノールを含む。
− バイオベース炭素の含有率が100%の天然由来のグリオキシル酸。
バイオベース炭素の含有率は、標準試験法ASTM D6866−16に従って測定される。
ジャケット、メカニカルスターラー、pH電極、還流冷却器系、及び不活性ガス注入口を備えた2リットルの316Lガラス製反応器に、以下のものを連続的に入れる:
− 600gの脱塩水
− 146g(1.1mol)の30重量%水酸化ナトリウム水溶液
− 100g(0.8mol)のグアイアコール。
この反応混合物を35℃の温度で維持する。次いで、50重量%のグリオキシル酸の水溶液(58g、0.39mol)を反応器に添加する。
全体の滞留時間は2.5時間である。
反応器の出口でこの反応媒体のサンプルを採取し、混合物中に存在する化合物を液体クロマトグラフィーにより分析する。
得られた結果は以下の通りである:
− グアイアコール(GA)の変換率: 45%
反応で化合物A(87%)、B(5%)、及びC(8%)が形成される。
キャビテーション型(「キャビテーター」)又はラシュトン型の自己吸引撹拌機と効率的な冷却のためのジャケットとを備えたステンレス鋼製酸化反応器に、以下のものを連続的に入れた:
− 縮合反応からの触媒とマンデル化合物の水溶液との混合物、すなわち:
・縮合反応により得られた反応媒体1.5kg。この混合物は、約100gの2−ヒドロキシ−2−(4−ヒドロキシ−3−メトキシフェニル)酢酸(A)、7gの2−ヒドロキシ−2−(2−ヒドロキシ−3−メトキシフェニル)酢酸(B)、及び10.6の2,2’−(4−ヒドロキシ−5−メトキシ−1,3−フェニレン)ビス(2−ヒドロキシ酢酸)(C)を含む。
・マンデル酸の合計のモル数に対する金属のモルパーセンテージとして表される量のCuSO4水溶液0.8g: 0.06%;
− 少なくとも酸化反応の化学量論により必要とされる量に対応する、適切な量の50重量%水酸化ナトリウム水溶液;
− マンデル酸を事実上完全に変換するのに十分な量の大気圧の酸素。酸化剤は、大気圧の酸素又は圧縮空気であってもよい。
この反応は75℃で行われる。反応器の出口でこの反応媒体のサンプルを採取し、混合物中に存在する化合物を液体クロマトグラフィーにより分析する。
得られた結果は以下の通りである:
− 2−ヒドロキシ−2−(4−ヒドロキシ−3−メトキシフェニル)酢酸の変換率: >99.5%
− バニリンVAの収率:95%
その後、純粋な結晶化バニリンを得るために反応混合物を精製する。バニリンの純度>99%
この純粋なバニリンを更に分析すると、以下のものが含まれる:
− 4−ヒドロキシ−5−メトキシイソフタルアルデヒド(化合物D)<30ppm、
− (E又はZ)−3−(4−ヒドロキシ−3−メトキシベンジリデン)−7−メトキシベンゾフラン−2(3H)−オン(化合物K)<400ppb、
− 4−ヒドロキシ−3−メチルベンズアルデヒド: 200ppm、
− 4−ヒドロキシ−3,5−ジメチルベンズアルデヒド:
150ppm。
− バイオベース炭素の含有率=100%。
Claims (25)
- バニリン及び/又はエチルバニリンであって、バイオベース炭素の含有率が75%〜100%であり、2−ヒドロキシ−2−(4−ヒドロキシ−3−メトキシフェニル)酢酸、4−ヒドロキシ−5−メトキシイソフタルアルデヒド、2,2’−(4−ヒドロキシ−5−メトキシ−1,3−フェニレン)ビス(2−ヒドロキシ酢酸)、2−ヒドロキシ−3−メトキシベンズアルデヒド、2−ヒドロキシ−2−(2−ヒドロキシ−3−メトキシフェニル)酢酸、2−(3−エトキシ−4−ヒドロキシフェニル)−2−ヒドロキシ酢酸、2−(3−エトキシ−2−ヒドロキシフェニル)−2−ヒドロキシ酢酸、2,2’−(5−エトキシ−4−ヒドロキシ−1,3−フェニレン)ビス(2−ヒドロキシ酢酸)、5−エトキシ−4−ヒドロキシイソフタルアルデヒド、3−エトキシ−2−ヒドロキシベンズアルデヒド、(E又はZ)−3−(4−ヒドロキシ−3−メトキシベンジリデン)−7−メトキシベンゾフラン−2(3H)−オン、(E又はZ)−7−エトキシ−3−(3−エトキシ−4−ヒドロキシベンジリデン)ベンゾフラン−2(3H)−オン、4−ヒドロキシ−3−メチルベンズアルデヒド、及び4−ヒドロキシ−3,5−ジメチルベンズアルデヒドからなる群から選択される少なくとも1つの化合物を含み、前記バニリン及び/又はエチルバニリンが90%超の純度を有する、バニリン及び/又はエチルバニリン。
- バニリン及び/又はエチルバニリンが、80%超、好ましくは85%〜100%、より好ましくは90%〜100%、より好ましくは95%〜100%、より好ましくは98%〜100%、より好ましくは99%〜100%のバイオベース炭素の含有率を有する、請求項1に記載のバニリン及び/又はエチルバニリン。
- −33‰〜−23‰、好ましくは−31‰〜−25‰、より好ましくは−30‰〜−26‰の平均同位体13C偏差を示す、請求項1又は2に記載のバニリン及び/又はエチルバニリン。
- 前記バニリン及び/又はエチルバニリンがリグニン又はバイオマスから直接製造されない、請求項1〜3のいずれか1項に記載のバニリン及び/又はエチルバニリン。
- 2−ヒドロキシ−2−(4−ヒドロキシ−3−メトキシフェニル)酢酸、4−ヒドロキシ−5−メトキシ−イソフタルアルデヒド、2,2’−(4−ヒドロキシ−5−メトキシ−1,3−フェニレン)ビス(2−ヒドロキシ酢酸)、2−ヒドロキシ−3−メトキシベンズアルデヒド、2−ヒドロキシ−2−(2−ヒドロキシ−3−メトキシフェニル)酢酸、(E又はZ)−3−(4−ヒドロキシ−3−メトキシベンジリデン)−7−メトキシベンゾフラン−2(3H)、4−ヒドロキシ−3−メチルベンズアルデヒド、及び4−ヒドロキシ−3,5−ジメチルベンズアルデヒドからなる群から選択される少なくとも1つの化合物を含む、請求項1〜4のいずれか1項に記載のバニリン。
- 95%超、より好ましくは96%超、より好ましくは99%超、より好ましくは99.5%超、最も好ましくは99.9%超の純度を有する、請求項1〜5のいずれか1項に記載のバニリン。
- 2−ヒドロキシ−2−(4−ヒドロキシ−3−メトキシフェニル)酢酸(A)、4−ヒドロキシ−5−メトキシイソフタルアルデヒド(D)、2,2’−(4−ヒドロキシ−5−メトキシ−1,3−フェニレン)ビス(2−ヒドロキシ酢酸)(C)、2−ヒドロキシ−3−メトキシベンズアルデヒド(E)、2−ヒドロキシ−2−(2−ヒドロキシ−3−メトキシフェニル)酢酸(B)、(E又はZ)−3−(4−ヒドロキシ−3−メトキシベンジリデン)−7−メトキシベンゾフラン−2(3H)−オン(K)、4−ヒドロキシ−3−メチルベンズアルデヒド、及び4−ヒドロキシ−3,5−ジメチルベンズアルデヒドからなる群から選択される化合物の量が、1〜5000ppm、好ましくは1ppm〜500ppm、より好ましくは1ppm〜50ppm、最も好ましくは1ppm〜20ppmに含まれる、請求項1〜6のいずれか1項に記載のバニリン。
- フレーク、ビーズ、プリル、又は粉末の形態である、請求項1〜7のいずれか1項に記載のバニリン。
- 満足できる官能特性を示す、請求項1〜8のいずれか1項に記載のバニリン。
- 2−(3−エトキシ−4−ヒドロキシフェニル)−2−ヒドロキシ酢酸、2−(3−エトキシ−2−ヒドロキシフェニル)−2−ヒドロキシ酢酸、2,2’−(5−エトキシ−4−ヒドロキシ−1,3−フェニレン)ビス(2−ヒドロキシ酢酸)、5−エトキシ−4−ヒドロキシイソフタルアルデヒド、3−エトキシ−2−ヒドロキシベンズアルデヒド、及び(E又はZ)−7−エトキシ−3−(3−エトキシ)−4−ヒドロキシベンジリデン)ベンゾフラン−2(3H)−オンからなる群から選択される少なくとも1つの化合物を含む、請求項1〜4のいずれか1項に記載のエチルバニリン。
- 95%超、より好ましくは96%超、更に好ましくは99%超、より好ましくは99.5%超、最も好ましくは99.9%超の純度を有する、請求項1〜4又は10のいずれか1項に記載のエチルバニリン。
- 2−(3−エトキシ−4−ヒドロキシフェニル)−2−ヒドロキシ酢酸(F)、2−(3−エトキシ−2−ヒドロキシフェニル)−2−ヒドロキシ酢酸(G)、2,2’−(5−エトキシ−4−ヒドロキシ−1,3−フェニレン)ビス(2−ヒドロキシ酢酸)(H)、5−エトキシ−4−ヒドロキシイソフタルアルデヒド(I)、3−エトキシ−2−ヒドロキシベンズアルデヒド(J)、及び(E又はZ)−7−エトキシ−3−(3−エトキシ−4−ヒドロキシベンジリデン)ベンゾフラン−2(3H)−オン(L)からなる群から選択される化合物の量が、1ppm〜5000ppm、好ましくは1ppm〜500ppm、より好ましくは1ppm〜50ppm、最も好ましくは1ppm〜20ppmに含まれる、請求項1〜4又は11のいずれか1項に記載のエチルバニリン。
- フレーク、ビーズ、プリル、又は粉末の形態である、請求項1〜4又は10〜12のいずれか1項に記載のエチルバニリン。
- バイオベース炭素の含有率が75%〜100%であるグアイアコール及び/又はグエトールとグリオキシル酸とを縮合する工程(a)、並びに前記縮合生成物を酸化する工程(b)を含む、バイオベース炭素の含有率が75%〜100%であるバニリン及び/又はエチルバニリンの調製方法。
- バイオベース炭素の含有率が75%〜100%であるグアイアコール及び/又はバイオベース炭素の含有率が75%〜100%であるグエトールと、グリオキシル酸とを縮合する工程(a)と、前記縮合生成物を酸化する工程(b)とを含む、請求項1〜9のいずれか1項に記載のバニリン並びに/又は請求項1〜4又は10〜13のいずれか1項に記載のエチルバニリンの調製方法。
- グリオキシル酸が、50%超、好ましくは60%超、より好ましくは75%〜100%、より好ましくは90%〜100%、より好ましくは95%〜100%、より好ましくは98%〜100%、より好ましくは99%〜100%のバイオベース炭素の含有率を有する、請求項14又は15に記載の方法。
- 前記グアイアコール又はグエトールと前記グリオキシル酸との間のモル比が1.0〜4.0、好ましくは1.2〜2.2である、請求項14〜16のいずれか1項に記載の方法。
- 請求項1〜9のいずれか1項に記載のバニリン並びに/又は請求項1〜4又は10〜13のいずれか1項に記載のエチルバニリンの、風味料又は香料としての、好ましくは産業における、より好ましくは食品、医薬品、又は化粧品産業における使用。
- 組成物であって、
− バイオベース炭素の含有率が75%〜100%であるバニリン及び/又はエチルバニリン;並びに
− 2−ヒドロキシ−2−(4−ヒドロキシ−3−メトキシフェニル)酢酸、4−ヒドロキシ−5−メトキシイソフタルアルデヒド、2,2’−(4−ヒドロキシ−5−メトキシ−1,3−フェニレン)ビス(2−ヒドロキシ酢酸)、2−ヒドロキシ−3−メトキシベンズアルデヒド、2−ヒドロキシ−2−(2−ヒドロキシ−3−メトキシフェニル)酢酸、2−(3−エトキシ−4−ヒドロキシフェニル)−2−ヒドロキシ酢酸、2−(3−エトキシ−2−ヒドロキシフェニル)−2−ヒドロキシ酢酸、2,2’−(5−エトキシ−4−ヒドロキシ−1,3−フェニレン)ビス(2−ヒドロキシ酢酸)、5−エトキシ−4−ヒドロキシイソフタルアルデヒド、3−エトキシ−2−ヒドロキシベンズアルデヒド、(E又はZ)−3−(4−ヒドロキシ−3−メトキシベンジリデン)−7−メトキシベンゾフラン−2(3H)−オン、(E又はZ)−7−エトキシ−3−(3−エトキシ−4−ヒドロキシベンジリデン)ベンゾフラン−2(3H)−オン、4−ヒドロキシ−3−メチルベンズアルデヒド、及び4−ヒドロキシ−3,5−ジメチルベンズアルデヒドからなる群から選択される少なくとも1つの化合物;
を含むか、又はこれから本質的になる組成物。 - 前記バニリン及び/又はエチルバニリンが前記組成物の主要な化合物を構成し、好ましくは前記組成物の総重量に対して50%超、より好ましくは70%超、更に好ましくは80%超を占める、請求項19に記載の組成物。
- 前記バニリン及び/又はエチルバニリンが、前記組成物の総重量に対して90%超、好ましくは95%超、より好ましくは96%超、より好ましくは99%超、最も好ましくは99.5%超を占める、請求項19又は20に記載の組成物。
- 前記不純物が、前記組成物の総重量に対して1ppm〜5000ppm、好ましくは1ppm〜500ppm、より好ましくは1ppm〜50ppm、最も好ましくは1ppm〜20ppmを占める、請求項19〜21のいずれか1項に記載の組成物。
- 前記不純物が、バニリン及び/又はエチルバニリンの総重量に対して1ppm〜100ppm、好ましくは1ppm〜50ppm、より好ましくは1ppm〜10ppmを占める、請求項19〜22のいずれか1項に記載の組成物。
- 前記組成物がバニリン及びエチルバニリンを含有し、前記バニリン/エチルバニリンモル比が2に等しい、請求項19〜23のいずれか1項に記載の組成物。
- 食品、飲料、化粧品製剤、医薬製剤、香料からなる群から選択される、請求項1〜9のいずれか1項に記載のバニリン並びに/又は請求項1〜4又は10〜13のいずれか1項に記載のエチルバニリンを含有する組成物。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US15/663,312 US20190031588A1 (en) | 2017-07-28 | 2017-07-28 | New vanillin and or ethylvanillin, process for their preparations and use thereof |
US15/663,312 | 2017-07-28 | ||
PCT/EP2018/070358 WO2019020773A1 (en) | 2017-07-28 | 2018-07-26 | NOVEL VANILLIN AND / OR ETHYLVANILLIN, PREPARATION METHOD AND USE THEREOF |
Publications (1)
Publication Number | Publication Date |
---|---|
JP2020528446A true JP2020528446A (ja) | 2020-09-24 |
Family
ID=63079903
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2020504399A Pending JP2020528446A (ja) | 2017-07-28 | 2018-07-26 | 新規なバニリン及び/又はエチルバニリン、それらの調製方法、並びにそれらの使用 |
Country Status (7)
Country | Link |
---|---|
US (1) | US20190031588A1 (ja) |
EP (1) | EP3658525A1 (ja) |
JP (1) | JP2020528446A (ja) |
CN (1) | CN110944969A (ja) |
AU (1) | AU2018305208B2 (ja) |
CA (1) | CA3068785A1 (ja) |
WO (1) | WO2019020773A1 (ja) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US11484052B2 (en) | 2017-07-28 | 2022-11-01 | Rhodia Operations | Vanillin and/or ethylvanillin, process for their preparations and use thereof |
FR3134582A1 (fr) | 2022-04-15 | 2023-10-20 | Rhodia Operations | Procédé de préparation d’un composé de formule (I) par fermentation |
FR3134583A1 (fr) | 2022-04-15 | 2023-10-20 | Rhodia Operations | Procédé continu de croissance d’un microorganisme |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DD301512A7 (de) * | 1989-12-13 | 1993-02-18 | Dresden Arzneimittel | Verfahren zur herstellung aromatischer hydroxyaldehyde |
JP2009221234A (ja) * | 2009-07-09 | 2009-10-01 | Takasago Internatl Corp | グリオキシル酸エステル二量体の製造方法及び新規グリオキシル酸エステル二量体 |
WO2014168473A1 (en) * | 2013-04-08 | 2014-10-16 | Stichting Dienst Landbouwkundig Onderzoek | Method for the depolymerization of lignin |
US20160251291A1 (en) * | 2012-07-26 | 2016-09-01 | Rhodia Operations | Method for producing alkoxyhydroxybenzaldehyde |
Family Cites Families (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2062205A (en) * | 1932-03-21 | 1936-11-24 | Boedecker Friedrich | Process of producing the m-alkylethers of protocatechuic aldehyde |
JPS4924928A (ja) * | 1972-07-03 | 1974-03-05 | ||
US5219745A (en) | 1989-10-16 | 1993-06-15 | E. I. Du Pont De Nemours And Company | Production of glyoxylic acid from glycolic acid |
FR2693458B1 (fr) | 1992-07-10 | 1994-12-09 | Rhone Poulenc Chimie | Procédé de para-hydroxyalkylation de composés aromatiques hydroxylés. |
CA2238215A1 (en) | 1997-06-19 | 1998-12-19 | Markus Wetli | Process for the production of vanillin |
FR2779718B1 (fr) * | 1998-06-16 | 2000-12-29 | Rhodia Chimie Sa | Procede de preparation de composes p-hydroxymandeliques eventuellement substitues et derives |
FR2917085B1 (fr) * | 2007-06-06 | 2009-07-17 | Rhodia Recherches & Tech | Procede de preparation d'un aldehyde hydroxyaromatique. |
FR2925047B1 (fr) | 2007-12-18 | 2010-01-01 | Rhodia Operations | Procede de preparation de composes p-hydroxymandeliques eventuellement substitues et derives. |
US20130232852A1 (en) | 2012-03-09 | 2013-09-12 | Thesis Chemistry, Llc | Method for tiered production of biobased chemicals and biofuels from lignin |
FR2993881B1 (fr) | 2012-07-26 | 2014-08-15 | Rhodia Operations | Procede de preparation d'alkoxyphenol et d'alkoxyhydroxybenzaldehyde |
FR2993882B1 (fr) * | 2012-07-26 | 2014-08-15 | Rhodia Operations | Procede de preparation d'alkoxyhydroxybenzaldehyde sensiblement exempte d'alkyl-alkoxyhydroxybenzaldehyde |
JP6596009B2 (ja) | 2013-11-04 | 2019-10-23 | ビージーエヌ テック エルエルシー | 植物デヒドロゲナーゼを用いるオイゲノールからのフェルラ酸の微生物発酵を介してバニリンを製造する方法 |
FR3013351B1 (fr) | 2013-11-15 | 2016-01-01 | Rhodia Operations | Procede de preparation de compose aromatique mandelique et de compose aldehyde aromatique |
FR3014869B1 (fr) * | 2013-12-18 | 2016-01-01 | Rhodia Operations | Procede de separation de composes mandeliques sous forme salifiee et son utilisation pour la preparation d'aldehyde aromatique |
WO2015121379A2 (en) * | 2014-02-12 | 2015-08-20 | Evolva Sa | Methods of improving production of vanillin |
-
2017
- 2017-07-28 US US15/663,312 patent/US20190031588A1/en not_active Abandoned
-
2018
- 2018-07-26 WO PCT/EP2018/070358 patent/WO2019020773A1/en active Application Filing
- 2018-07-26 AU AU2018305208A patent/AU2018305208B2/en active Active
- 2018-07-26 EP EP18749327.5A patent/EP3658525A1/en active Pending
- 2018-07-26 CN CN201880048981.3A patent/CN110944969A/zh active Pending
- 2018-07-26 JP JP2020504399A patent/JP2020528446A/ja active Pending
- 2018-07-26 CA CA3068785A patent/CA3068785A1/en active Pending
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DD301512A7 (de) * | 1989-12-13 | 1993-02-18 | Dresden Arzneimittel | Verfahren zur herstellung aromatischer hydroxyaldehyde |
JP2009221234A (ja) * | 2009-07-09 | 2009-10-01 | Takasago Internatl Corp | グリオキシル酸エステル二量体の製造方法及び新規グリオキシル酸エステル二量体 |
US20160251291A1 (en) * | 2012-07-26 | 2016-09-01 | Rhodia Operations | Method for producing alkoxyhydroxybenzaldehyde |
WO2014168473A1 (en) * | 2013-04-08 | 2014-10-16 | Stichting Dienst Landbouwkundig Onderzoek | Method for the depolymerization of lignin |
Non-Patent Citations (9)
Title |
---|
BARROWS R D; ET AL: "ANALYSIS OF CHEMICAL INTERMEDIATES FROM LOW-TEMPERATURE STEAM GASIFICATION OF BIOMASS", FUEL, vol. VOL:63, NR:1, JPN5020009332, 1984, GB, pages 4 - 8, ISSN: 0004959266 * |
CHEMSUSCHEM, vol. 9, no. 22, JPN6022020743, 23 November 2016 (2016-11-23), pages 3220 - 3229, ISSN: 0004959273 * |
DURAK HALIL; ET AL: "STRUCTURAL ANALYSIS OF BIO-OILS FROM SUBCRITICAL AND SUPERCRITICAL HYDROTHERMAL 以下備考", THE JOURNAL OF SUPERCRITICAL FLUIDS, vol. 108, JPN5020009333, 27 October 2015 (2015-10-27), pages 123 - 135, ISSN: 0004959268 * |
LEOPOLD, BENGT; ET AL.: "Studies on Lignin. III. Oxidation of Wood from Picea abies (L.) Karst. (Norway Spruce) with Nitroben", ACTA CHEMICA SCANDINAVICA, vol. 6, JPN6022020746, 1952, pages 38 - 48, XP055477328, ISSN: 0004959265, DOI: 10.3891/acta.chem.scand.06-0038 * |
TENAILLEAU, EVE J. ET AL.: "Authentication of the origin of vanillin using quantitative natural abundance 13C NMR", JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, vol. 52(26), JPN6022020744, 2004, pages 7782 - 7787, ISSN: 0004959270 * |
XIE, SHANGXIAN ET AL.: "Advanced Chemical Design for Efficient Lignin Bioconversion", ACS SUSTAINABLE CHEMISTRY & ENGINEERING, vol. 5(3), JPN6022020745, 22 December 2016 (2016-12-22), pages 2215 - 2223, ISSN: 0004959267 * |
インド特許公開00636MU2010, JPN7022002396, 17 February 2012 (2012-02-17), ISSN: 0004959269 * |
印藤元一, 合成香料 化学と商品知識, JPN6022020742, 22 March 2005 (2005-03-22), pages 224 - 226, ISSN: 0004959271 * |
木材学会誌, vol. 14, no. 7, JPN6022020741, 1968, pages 382 - 386, ISSN: 0004959272 * |
Also Published As
Publication number | Publication date |
---|---|
CN110944969A (zh) | 2020-03-31 |
WO2019020773A1 (en) | 2019-01-31 |
AU2018305208B2 (en) | 2022-08-18 |
CA3068785A1 (en) | 2019-01-31 |
AU2018305208A1 (en) | 2020-01-30 |
US20190031588A1 (en) | 2019-01-31 |
EP3658525A1 (en) | 2020-06-03 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP3045444B1 (en) | Method of preparing vanillin | |
JP2020528446A (ja) | 新規なバニリン及び/又はエチルバニリン、それらの調製方法、並びにそれらの使用 | |
CN111187148B (zh) | 一种同时制备邻羟基苯乙醚和1,3-苯并二氧戊环-2-酮的方法 | |
Ren et al. | Clean synthesis of adipic acid catalyzed by complexes derived from heteropoly acid and glycine | |
KR101679717B1 (ko) | 알릴 알코올의 제조방법 및 이에 의하여 제조된 알릴 알코올 | |
US11484052B2 (en) | Vanillin and/or ethylvanillin, process for their preparations and use thereof | |
CN112225653B (zh) | 天然苯甲醛的绿色合成方法 | |
CN101973860B (zh) | 一种由多聚甲醛制备2,3-丁二酮的方法 | |
US20230416182A1 (en) | Process for preparing frambione | |
CN108129350B (zh) | 一种2,4-二氯苯腈的制备方法 | |
WO2007073240A1 (fr) | Catalyseur, procede de preparation et procede de fabrication de dihydroxy-alcanes | |
JP7413412B2 (ja) | 硝酸を使用してグリコールアルデヒドを酸化する方法 | |
CN112110812B (zh) | 一种γ-取代己二烯酸的制备方法 | |
CN113121323B (zh) | 一种对羟基苯甲醛的制备方法 | |
CN117486701A (zh) | 一种乙醛酸法合成香兰素的方法 | |
JPS6151572B2 (ja) | ||
CN102424650B (zh) | 一种乙酸苏合香酯的制备工艺 | |
CN107032971B (zh) | 一种3,7-二甲基-6-羰基-2-辛烯醛的制备方法 | |
CN108017558B (zh) | 一种大茴香腈的制备方法 | |
CN116670109A (zh) | 用于生产乙醇酸的方法 | |
Fridrich | Climbing the Bio-based Value Pyramid by Novel Transformations | |
CN115974677A (zh) | 戊二酸的制备方法 | |
TWI610912B (zh) | 2-氯甲基苯甲醛之製造方法、含2-氯甲基苯甲醛之組成物及其保管方法 | |
CN117430519A (zh) | 一种氯代高丝氨酸盐酸盐的制备方法 | |
WO2023144408A1 (en) | Bio-based methyl dihydrojasmonate, bio-based cyclopentanone, process for their preparation and use thereof |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20210628 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20220506 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20220531 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20220829 |
|
A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20230110 |