EP3551640A1 - Procédé de préparation de compositions tensioactives comprenant des l-iduronamides, d-glucuronamides et l-rhamnosides d'alkyle à partir d'ulvanes - Google Patents
Procédé de préparation de compositions tensioactives comprenant des l-iduronamides, d-glucuronamides et l-rhamnosides d'alkyle à partir d'ulvanesInfo
- Publication number
- EP3551640A1 EP3551640A1 EP17821978.8A EP17821978A EP3551640A1 EP 3551640 A1 EP3551640 A1 EP 3551640A1 EP 17821978 A EP17821978 A EP 17821978A EP 3551640 A1 EP3551640 A1 EP 3551640A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- alkyl
- acid
- formula
- composition
- surfactant
- 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.)
- Withdrawn
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 91
- 239000004094 surface-active agent Substances 0.000 title claims abstract description 62
- 238000000034 method Methods 0.000 title claims abstract description 43
- -1 alkyl l-iduronamides Chemical class 0.000 title claims description 49
- 150000008451 L-rhamnosides Chemical class 0.000 title description 8
- JRIOKBXQMHEJOZ-QTBDOELSSA-N (2s,3s,4s,5r)-2,3,4,5-tetrahydroxy-6-oxohexanamide Chemical class NC(=O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O JRIOKBXQMHEJOZ-QTBDOELSSA-N 0.000 title 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 22
- 230000008569 process Effects 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 17
- 229920006395 saturated elastomer Polymers 0.000 claims description 15
- 230000000844 anti-bacterial effect Effects 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 150000001412 amines Chemical class 0.000 claims description 12
- 239000012429 reaction media Substances 0.000 claims description 12
- 241000195628 Chlorophyta Species 0.000 claims description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 11
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical group CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 11
- 239000003995 emulsifying agent Substances 0.000 claims description 11
- 230000001804 emulsifying effect Effects 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 238000007098 aminolysis reaction Methods 0.000 claims description 10
- 238000006386 neutralization reaction Methods 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- 230000002829 reductive effect Effects 0.000 claims description 9
- 230000000843 anti-fungal effect Effects 0.000 claims description 8
- 238000005918 transglycosylation reaction Methods 0.000 claims description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 7
- 150000007513 acids Chemical class 0.000 claims description 7
- 230000006098 transglycosylation Effects 0.000 claims description 7
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 claims description 6
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 claims description 6
- 238000006206 glycosylation reaction Methods 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 5
- 239000003377 acid catalyst Substances 0.000 claims description 4
- 229940121375 antifungal agent Drugs 0.000 claims description 4
- 239000002585 base Substances 0.000 claims description 4
- 230000005496 eutectics Effects 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 3
- 239000003599 detergent Substances 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 150000002739 metals Chemical class 0.000 claims description 3
- RYVMUASDIZQXAA-UHFFFAOYSA-N pyranoside Natural products O1C2(OCC(C)C(OC3C(C(O)C(O)C(CO)O3)O)C2)C(C)C(C2(CCC3C4(C)CC5O)C)C1CC2C3CC=C4CC5OC(C(C1O)O)OC(CO)C1OC(C1OC2C(C(OC3C(C(O)C(O)C(CO)O3)O)C(O)C(CO)O2)O)OC(CO)C(O)C1OC1OCC(O)C(O)C1O RYVMUASDIZQXAA-UHFFFAOYSA-N 0.000 claims description 3
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 claims description 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 2
- 239000003242 anti bacterial agent Substances 0.000 claims description 2
- 239000003429 antifungal agent Substances 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- ALSTYHKOOCGGFT-UHFFFAOYSA-N cis-oleyl alcohol Natural products CCCCCCCCC=CCCCCCCCCO ALSTYHKOOCGGFT-UHFFFAOYSA-N 0.000 claims description 2
- 238000005187 foaming Methods 0.000 claims description 2
- 239000004088 foaming agent Substances 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 230000003165 hydrotropic effect Effects 0.000 claims description 2
- 239000007764 o/w emulsion Substances 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 230000003381 solubilizing effect Effects 0.000 claims description 2
- 238000009736 wetting Methods 0.000 claims description 2
- 239000000080 wetting agent Substances 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 239000007762 w/o emulsion Substances 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- SHZGCJCMOBCMKK-UHFFFAOYSA-N D-mannomethylose Natural products CC1OC(O)C(O)C(O)C1O SHZGCJCMOBCMKK-UHFFFAOYSA-N 0.000 description 25
- 241000894006 Bacteria Species 0.000 description 22
- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 description 17
- 239000000839 emulsion Substances 0.000 description 17
- PNNNRSAQSRJVSB-UHFFFAOYSA-N L-rhamnose Natural products CC(O)C(O)C(O)C(O)C=O PNNNRSAQSRJVSB-UHFFFAOYSA-N 0.000 description 16
- 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 description 14
- 150000001408 amides Chemical class 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 239000003921 oil Substances 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 10
- 239000002609 medium Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- AEMOLEFTQBMNLQ-WAXACMCWSA-N alpha-D-glucuronic acid Chemical compound O[C@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-WAXACMCWSA-N 0.000 description 9
- 230000005764 inhibitory process Effects 0.000 description 9
- 235000019198 oils Nutrition 0.000 description 9
- 235000000346 sugar Nutrition 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 8
- 230000001580 bacterial effect Effects 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 229920001817 Agar Polymers 0.000 description 7
- 239000008272 agar Substances 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- AEMOLEFTQBMNLQ-CLQWQSTFSA-N l-iduronic acid Chemical compound O[C@H]1O[C@H](C(O)=O)[C@H](O)[C@@H](O)[C@@H]1O AEMOLEFTQBMNLQ-CLQWQSTFSA-N 0.000 description 7
- 238000005259 measurement Methods 0.000 description 7
- 150000002772 monosaccharides Chemical class 0.000 description 7
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 6
- 241000194031 Enterococcus faecium Species 0.000 description 6
- 241000893983 Ulva linza Species 0.000 description 6
- 238000010790 dilution Methods 0.000 description 6
- 239000012895 dilution Substances 0.000 description 6
- 150000002338 glycosides Chemical class 0.000 description 6
- 241000222122 Candida albicans Species 0.000 description 5
- 241000588724 Escherichia coli Species 0.000 description 5
- 235000019486 Sunflower oil Nutrition 0.000 description 5
- 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 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 150000002243 furanoses Chemical class 0.000 description 5
- 229930182470 glycoside Natural products 0.000 description 5
- 239000002054 inoculum Substances 0.000 description 5
- 150000003214 pyranose derivatives Chemical class 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 238000010898 silica gel chromatography Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000002600 sunflower oil Substances 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 241000191967 Staphylococcus aureus Species 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 4
- 229940095731 candida albicans Drugs 0.000 description 4
- 150000001720 carbohydrates Chemical class 0.000 description 4
- 229940097043 glucuronic acid Drugs 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
- 229920001282 polysaccharide Polymers 0.000 description 4
- 239000005017 polysaccharide Substances 0.000 description 4
- 150000004804 polysaccharides Chemical class 0.000 description 4
- 238000004064 recycling Methods 0.000 description 4
- 150000008265 rhamnosides Chemical class 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 150000008163 sugars Chemical class 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- JRIOKBXQMHEJOZ-SKNVOMKLSA-N (2R,3S,4S,5R)-2,3,4,5-tetrahydroxy-6-oxohexanamide Chemical class NC(=O)[C@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O JRIOKBXQMHEJOZ-SKNVOMKLSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
- AEMOLEFTQBMNLQ-HNFCZKTMSA-N L-idopyranuronic acid Chemical compound OC1O[C@@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-HNFCZKTMSA-N 0.000 description 3
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 241000196252 Ulva Species 0.000 description 3
- 241000196251 Ulva arasakii Species 0.000 description 3
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 3
- 235000014633 carbohydrates Nutrition 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 230000002538 fungal effect Effects 0.000 description 3
- 239000008103 glucose Substances 0.000 description 3
- 230000013595 glycosylation Effects 0.000 description 3
- 239000001963 growth medium Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- KYCQOKLOSUBEJK-UHFFFAOYSA-M 1-butyl-3-methylimidazol-3-ium;bromide Chemical compound [Br-].CCCCN1C=C[N+](C)=C1 KYCQOKLOSUBEJK-UHFFFAOYSA-M 0.000 description 2
- KVGOXGQSTGQXDD-UHFFFAOYSA-N 1-decane-sulfonic-acid Chemical compound CCCCCCCCCCS(O)(=O)=O KVGOXGQSTGQXDD-UHFFFAOYSA-N 0.000 description 2
- LDMOEFOXLIZJOW-UHFFFAOYSA-N 1-dodecanesulfonic acid Chemical compound CCCCCCCCCCCCS(O)(=O)=O LDMOEFOXLIZJOW-UHFFFAOYSA-N 0.000 description 2
- AEMOLEFTQBMNLQ-YMDCURPLSA-N D-galactopyranuronic acid Chemical compound OC1O[C@H](C(O)=O)[C@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-YMDCURPLSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 241000192125 Firmicutes Species 0.000 description 2
- 229920002488 Hemicellulose Polymers 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- MSFSPUZXLOGKHJ-UHFFFAOYSA-N Muraminsaeure Natural products OC(=O)C(C)OC1C(N)C(O)OC(CO)C1O MSFSPUZXLOGKHJ-UHFFFAOYSA-N 0.000 description 2
- 108010013639 Peptidoglycan Proteins 0.000 description 2
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 2
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical compound OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- PNNNRSAQSRJVSB-BXKVDMCESA-N aldehydo-L-rhamnose Chemical compound C[C@H](O)[C@H](O)[C@@H](O)[C@@H](O)C=O PNNNRSAQSRJVSB-BXKVDMCESA-N 0.000 description 2
- 229920000615 alginic acid Polymers 0.000 description 2
- 235000010443 alginic acid Nutrition 0.000 description 2
- 150000003973 alkyl amines Chemical class 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
- AEMOLEFTQBMNLQ-UHFFFAOYSA-N beta-D-galactopyranuronic acid Natural products OC1OC(C(O)=O)C(O)C(O)C1O AEMOLEFTQBMNLQ-UHFFFAOYSA-N 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000000356 contaminant Substances 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- AEMOLEFTQBMNLQ-YBSDWZGDSA-N d-mannuronic acid Chemical compound O[C@@H]1O[C@@H](C(O)=O)[C@H](O)[C@@H](O)[C@H]1O AEMOLEFTQBMNLQ-YBSDWZGDSA-N 0.000 description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
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- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
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- 229910052742 iron Inorganic materials 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
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- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
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- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- JRIOKBXQMHEJOZ-MBMOQRBOSA-N (2s,3s,4s,5s)-2,3,4,5-tetrahydroxy-6-oxohexanamide Chemical compound NC(=O)[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)C=O JRIOKBXQMHEJOZ-MBMOQRBOSA-N 0.000 description 1
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- FHDQNOXQSTVAIC-UHFFFAOYSA-M 1-butyl-3-methylimidazol-3-ium;chloride Chemical compound [Cl-].CCCCN1C=C[N+](C)=C1 FHDQNOXQSTVAIC-UHFFFAOYSA-M 0.000 description 1
- IQQRAVYLUAZUGX-UHFFFAOYSA-N 1-butyl-3-methylimidazolium Chemical compound CCCCN1C=C[N+](C)=C1 IQQRAVYLUAZUGX-UHFFFAOYSA-N 0.000 description 1
- XIYUIMLQTKODPS-UHFFFAOYSA-M 1-ethyl-3-methylimidazol-3-ium;acetate Chemical compound CC([O-])=O.CC[N+]=1C=CN(C)C=1 XIYUIMLQTKODPS-UHFFFAOYSA-M 0.000 description 1
- NJMWOUFKYKNWDW-UHFFFAOYSA-N 1-ethyl-3-methylimidazolium Chemical compound CCN1C=C[N+](C)=C1 NJMWOUFKYKNWDW-UHFFFAOYSA-N 0.000 description 1
- TYTGWHZODQKWEF-UHFFFAOYSA-N 1-o-dodecyl 4-o-sulfo butanedioate Chemical compound CCCCCCCCCCCCOC(=O)CCC(=O)OS(O)(=O)=O TYTGWHZODQKWEF-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- PTWCXQAFLPJHJQ-UHFFFAOYSA-N 2-decyl-2-sulfobutanedioic acid Chemical compound CCCCCCCCCCC(S(O)(=O)=O)(C(O)=O)CC(O)=O PTWCXQAFLPJHJQ-UHFFFAOYSA-N 0.000 description 1
- MJJJJEUEZVGFLW-UHFFFAOYSA-N 2-dodecyl-2-sulfobutanedioic acid Chemical compound CCCCCCCCCCCCC(S(O)(=O)=O)(C(O)=O)CC(O)=O MJJJJEUEZVGFLW-UHFFFAOYSA-N 0.000 description 1
- 238000012584 2D NMR experiment Methods 0.000 description 1
- 238000005084 2D-nuclear magnetic resonance Methods 0.000 description 1
- GLKSLQGFGAMTOV-UHFFFAOYSA-N 4-decoxy-4-oxo-3-sulfobutanoic acid Chemical compound CCCCCCCCCCOC(=O)C(S(O)(=O)=O)CC(O)=O GLKSLQGFGAMTOV-UHFFFAOYSA-N 0.000 description 1
- 241001185285 Boergesenia forbesii Species 0.000 description 1
- 239000007848 Bronsted acid Substances 0.000 description 1
- 241001290347 Caulerpa taxifolia Species 0.000 description 1
- 241000983537 Chara globularis Species 0.000 description 1
- 241000923152 Charophyceae Species 0.000 description 1
- 241001147674 Chlorarachniophyceae Species 0.000 description 1
- 241000899898 Chlorokybophyceae Species 0.000 description 1
- 102100026735 Coagulation factor VIII Human genes 0.000 description 1
- 241001195759 Coleochaetales Species 0.000 description 1
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- 101000911390 Homo sapiens Coagulation factor VIII Proteins 0.000 description 1
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- 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
- 241000899859 Klebsormidiophyceae Species 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 241000382425 Mesostigmatophyceae Species 0.000 description 1
- 239000012901 Milli-Q water Substances 0.000 description 1
- 241000199919 Phaeophyceae Species 0.000 description 1
- 241000589516 Pseudomonas Species 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 108010059993 Vancomycin Proteins 0.000 description 1
- 241000899931 Zygnemophyceae Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- IAJILQKETJEXLJ-SKNVOMKLSA-N aldehydo-L-iduronic acid Chemical class O=C[C@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O IAJILQKETJEXLJ-SKNVOMKLSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 229920001586 anionic polysaccharide Polymers 0.000 description 1
- 150000004836 anionic polysaccharides Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- KTUQUZJOVNIKNZ-UHFFFAOYSA-N butan-1-ol;hydrate Chemical compound O.CCCCO KTUQUZJOVNIKNZ-UHFFFAOYSA-N 0.000 description 1
- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 229960000484 ceftazidime Drugs 0.000 description 1
- NMVPEQXCMGEDNH-TZVUEUGBSA-N ceftazidime pentahydrate Chemical compound O.O.O.O.O.S([C@@H]1[C@@H](C(N1C=1C([O-])=O)=O)NC(=O)\C(=N/OC(C)(C)C(O)=O)C=2N=C(N)SC=2)CC=1C[N+]1=CC=CC=C1 NMVPEQXCMGEDNH-TZVUEUGBSA-N 0.000 description 1
- 230000030833 cell death Effects 0.000 description 1
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- 210000002421 cell wall Anatomy 0.000 description 1
- 239000007806 chemical reaction intermediate Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
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- 238000009792 diffusion process Methods 0.000 description 1
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- 239000012153 distilled water Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 210000002889 endothelial cell Anatomy 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000000374 eutectic mixture Substances 0.000 description 1
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- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000005614 guluronate group Chemical group 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 238000003919 heteronuclear multiple bond coherence Methods 0.000 description 1
- 210000005260 human cell Anatomy 0.000 description 1
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- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 210000002510 keratinocyte Anatomy 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 229940071180 lauryl sulfosuccinate Drugs 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 229910001510 metal chloride Inorganic materials 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- 238000000199 molecular distillation Methods 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 239000013642 negative control Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
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- 238000007254 oxidation reaction Methods 0.000 description 1
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- 239000012071 phase Substances 0.000 description 1
- 230000000243 photosynthetic effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- HWLDNSXPUQTBOD-UHFFFAOYSA-N platinum-iridium alloy Chemical compound [Ir].[Pt] HWLDNSXPUQTBOD-UHFFFAOYSA-N 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 210000004927 skin cell Anatomy 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000019635 sulfation Effects 0.000 description 1
- 238000005670 sulfation reaction Methods 0.000 description 1
- FZUJWWOKDIGOKH-UHFFFAOYSA-N sulfuric acid hydrochloride Chemical compound Cl.OS(O)(=O)=O FZUJWWOKDIGOKH-UHFFFAOYSA-N 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
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- 230000009466 transformation Effects 0.000 description 1
- 238000002495 two-dimensional nuclear magnetic resonance spectrum Methods 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
- MYPYJXKWCTUITO-LYRMYLQWSA-N vancomycin Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)NC)[C@H]1C[C@](C)(N)[C@H](O)[C@H](C)O1 MYPYJXKWCTUITO-LYRMYLQWSA-N 0.000 description 1
- 229960003165 vancomycin Drugs 0.000 description 1
- MYPYJXKWCTUITO-UHFFFAOYSA-N vancomycin Natural products O1C(C(=C2)Cl)=CC=C2C(O)C(C(NC(C2=CC(O)=CC(O)=C2C=2C(O)=CC=C3C=2)C(O)=O)=O)NC(=O)C3NC(=O)C2NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(CC(C)C)NC)C(O)C(C=C3Cl)=CC=C3OC3=CC2=CC1=C3OC1OC(CO)C(O)C(O)C1OC1CC(C)(N)C(O)C(C)O1 MYPYJXKWCTUITO-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
- A01N43/16—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with oxygen as the ring hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
- A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/04—Dispersions; Emulsions
- A61K8/06—Emulsions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/60—Sugars; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
- A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
- A61K8/9706—Algae
- A61K8/9722—Chlorophycota or Chlorophyta [green algae], e.g. Chlorella
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/005—Antimicrobial preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/10—Washing or bathing preparations
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H7/00—Compounds containing non-saccharide radicals linked to saccharide radicals by a carbon-to-carbon bond
- C07H7/02—Acyclic radicals
- C07H7/033—Uronic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/49—Solubiliser, Solubilising system
Definitions
- the present invention relates to a new process for preparing compositions comprising alkyl L-iduronamides, alkyl L-rhamnosides and alkyl D-glucuronamides, directly from biosourced raw materials (ulvans, green algae). ) or biocompatible / biodegradable, the compositions obtained by said process and their uses.
- the present invention finds, for example, applications in the field of surfactants, in particular for cosmetics, phytosanitary, agri-food, detergency (industrial).
- references in brackets ([]) refer to the list of references at the end of the text.
- carbohydrate surfactants represent a large class of amphiphilic compounds whose increasing interest can be explained by functional, economic and environmental factors (Hill and Lehen-Ferrenbach, 2009) [1].
- the amide derivatives of sugars characterized by the presence of an amide function connecting the hydrophilic sugar head to the lipophilic chain have the advantage of being resistant to hydrolysis in neutral and alkaline media, especially compared to the derivatives esters (Laurent et al., 201 1) [2].
- amide surfactant is derived from the transformation of oligomers of D-mannuronic acid from the depolymerization of alginates.
- Ulvans are a family of polysaccharides that have recently been described in green algae of the Ulva or Enteromorpha type, species very present on the Mediterranean and Brittany coasts. These are polysaccharides whose composition is unique. They consist mainly of rhamnose and uronic acids (L-iduronic and D-glucuronic), elementary units to which are added glucose and xylose in the minority. The sulfation rate is generally high (5-30%). However, the use of ulvans as sources of L-iduronic and D-glucuronic acids and L-rhamnose for the potential preparation of monosaccharide surfactants has not been developed or even considered to date.
- esters sorbitan esters, sucroesters
- acetals alkylpolyglucosides
- amides alkyl glucamides
- the alkyl sucroamides are produced in two steps: reductive amination of a carbohydrate with an alkylamine, followed by the acylation of the resulting ⁇ -glycoside (International Application WO 92/06984, International Application WO 93/03004, EP Patent 0 536,939; US Patent 5,872,1 1 1) [3-6].
- gluconamides are obtained in two stages: the oxidation of a carbohydrate leading to a lactone or an aldonic acid followed by a reaction with alkylamines to form gluconamides (US Pat. No. 2,670,345) [7].
- Derivatives having an amide bond between the hydrophilic and lipophilic parts via a / V-glycoside linkage have been more recently developed (US Pat. No. 7,655,61 1) [8].
- Mannuronamide surfactants have been produced from oligomers of D-mannuronic acid (Benvegnu and Sassi, 2010, International Application WO 03/104248) [9, 10]. The process is based on the production of saturated oligomannuronates (acid depolymerization) which are then converted into a monosaccharide intermediate having two butyl chains. This synthon is then subjected to an aminolysis reaction using a fatty amine in a solvent such as methanol or isopropanol in the presence or absence of an organic base. The surfactant / V-acylated thus obtained has emulsifying properties.
- compositions comprising alkyl L-guluronamides or a mixture of alkyl L-guluronamides and alkyl D-mannuronamides have been produced from poly (oligo) guluronates, oligoalginates, alginates and the like. or brown algae, following a butanolysis and Fischer glycosylation step and an aminolysis step (Sari-Chmayssem et al., 2016) [13].
- the inventors have therefore developed a novel process, without solvent, using biocompatible / biodegradable reagents, to simply access surfactant compositions based on alkyl L-iduronamide, alkyl L-rhamnoside and Alkyl D-glucuronamide, directly from ulvans or green algae. Ulvans are for example extracted from the green alga Ulva lactuca or
- the subject of the present invention is therefore a process for the preparation of a composition
- a composition comprising a mixture of alkyl D-glucuronamides of formula (I) in the pyranoside form of formula (Ia) and of furanoside of formula (Ib), of L - Alkyl iduronamide of formula (II), and of alkyl L-rhamnoside of formula (III):
- Ri is an alkyl linear chain of 2 to 22 carbon atoms linear or branched, saturated or unsaturated;
- R2 is a hydrogen, Ri, a linear or branched, saturated or unsaturated alkyl chain of 2 to 22 carbon atoms containing an amino terminal function;
- step b) an aminolysis reaction step on the reaction medium resulting from step a), in the presence of an amine of formula R'Nh where R 'is composed of 2 to 22, preferably of 8 to 18, preferentially from 12 to 18 carbon atoms, linear or branched, saturated or unsaturated.
- the term "ulvans” is understood to mean sulfated anionic polysaccharides dissolved in water, extracted from green algae of the ulva or enteromorphic type.
- green algae in the sense of the present invention is meant a set of algae whose main photosynthetic pigments are chorophylls a and b. They include various organisms whose sizes can range from a few millimeters to more than one meter and whose aspects can be very diverse. Green algae are represented by the following groups: Euglenophyceae, Chlorarachniophyta, Chlorophytes, Chlorokybophyceae, Klebsormidiophyceae, Zygnematophyceae, Chaetosphaeridiophyta, Charophyceae, and Coleochaetales. Examples of green algae species include Caulerpa taxifolia, Chara globularis, Ulva lactuca, Ulva linza and Boergesenia forbesii.
- said method comprises, before step a), a step of preparing ulvans.
- the supernatant containing the ulvans is purified (elimination of polyphenol contaminants) by precipitation with ethanol (2.5 to 3 times the volume of the aqueous solution containing ulvans) and the precipitated ulvans are neutralized with an aqueous solution of 0.1 M NaOH and the solution is lyophilized to yield ulvans in the form of sodium salts (white solid).
- the chemical composition of ulvan is characterized for example by a molar mass of 565100 g.
- the butanolysis and glycosylation step of Fisher a) is carried out in the presence of (i) water and / or an ionic solvent and / or a eutectic solvent, (ii) a linear or branched, saturated or unsaturated ROH alcohol having 1 to 4 carbon atoms, preferably n-butanol, and (iii) an acidic catalyst such as, for example, hydrochloric acid sulfuric acid, an alkyl sulfuric acid such as decyl or lauryl sulfuric acid, a sulphonic acid such as benzenesulphonic acid, paratoluene sulphonic acid, camphorsulphonic acid, an alkylsulphonic acid such as methylsulphonic acid, (AMS), decylsulfonic acid, laurylsulfonic acid, sulfosuccinic acid or an alkyl sulfosuccinate such as decyl sulfo
- an acidic catalyst such as, for
- ionic solvent is understood to mean, for example, 1-butyl-3-methylimidazolium chloride [BMIM] CI, 1-butyl-3-methylimidazolium bromide [BMIM] Br, tris methylsulfate and the like. - (2-hydroxyethyl) methylammonium (HEMA) and 1-ethyl-3-methylimidazolium acetate [EMIM] AcO; said ionic solvent typically comprising up to 10% water.
- BMIM 1-butyl-3-methylimidazolium chloride
- BMIM 1-butyl-3-methylimidazolium bromide
- HEMA 2-hydroxyethyl) methylammonium
- EMIM 1-ethyl-3-methylimidazolium acetate
- eutectic solvent within the meaning of the present invention is meant systems formed of a eutectic mixture of bases or Lewis or Bronsted acids which may contain a variety of anionic species and / or cationic species.
- the first generation eutectic solvents were based on mixtures of quaternary ammonium salts with hydrogen bonding donors such as amines and carboxylic acids (eg quaternary ammonium salt and (hydrate of) metal chloride.
- This step a) is carried out, for example, by bringing into contact an equivalent of ulvan with a molar mass of between 150,000 and 3,600,000 g. mol "1 , preferably about 560000 g, mol- 1 , from Ulva linza or Ulva lactuca; 10 to 1000 molar equivalents of water, and preferably 500 molar equivalents; From 2 to 300 molar equivalents of an alcohol as defined above, for example n-butanol, and preferably 150 molar equivalents; 10 "3 to 10 molar equivalents of an acid catalyst, such as hydrochloric acid, sulfuric acid, an alkyl sulfuric acid such as decyl or lauryl sulfuric acid, a sulfonic acid such as benzenesulphonic acid, para-toluenesulfonic acid, camphorsulfonic acid, an alkylsulfonic acid such as methylsulfonic acid, decylsulfonic acid, lauryls
- composition thus formed consists mainly of (n-alkyl) -n-alkyl L-iduronate, (n-alkyl) -n-alkyl D-glucuronate and n-alkyl L-rhamnoside (with, for example, the alkyl group which corresponds to butyl in the case of the use of butanol).
- said method may further comprise a step a ') of neutralization of the reaction medium resulting from step a), and carried out before step b), leading to a final composition including a variable amount of residual fatty amine salt.
- the neutralization step is carried out in the presence of 1 M sodium hydroxide, up to a pH of 7.
- the reaction is carried out at a temperature of preferably 65-70 ° C and under reduced pressure for the recycling of the above-mentioned alcohol.
- the aminolysis reaction is carried out according to the two protocols below:
- R'Nh linear or branched, saturated or unsaturated where R 'is composed of 2 to 22 carbon atoms, and preferably 3 molar equivalents.
- the fatty amine is selected from the group consisting of dodecylamine and oleic amine.
- the reaction is conducted at a temperature of preferably 65-70 ° C and under reduced pressure for the recycle of the above-mentioned alcohol.
- the composition thus formed constitutes a product of use derived from L-iduronic acid and D-glucuronic acid in the form of amides and rhamnose in the form of glycoside as emulsifiers.
- the unreacted salts and sugars can be removed from this composition by taking up in an organic solvent, preferably diethyl ether, and then filtered and rinsed several times with the organic solvent.
- the filtrate containing the L-iduronamides, L-rhamnosides and alkyl D-glucuronamides is concentrated to give a composition enriched in products of interest which also constitutes a product of use such as an emulsifying agent having antibacterial and antifungal properties at the concentrations used for emulsion formation.
- the fatty amine is selected from the group consisting of dodecylamine and oleic amine.
- the reaction is conducted at a temperature of preferably 65-70 ° C and under reduced pressure for the recycling of the aforementioned alcohol.
- from 100 to 1000 molar equivalents of water, preferably 500 equivalents are added to the medium.
- the mixture is stirred for about 15 minutes at 65-70 ° C.
- the medium is left for about 10 minutes at this same temperature so that the organic products flocculate.
- the organic phase solidifies and it is then easy to remove the salt-laden water according to techniques well known to those skilled in the art.
- the preparation of a composition comprising L-iduronamide derivatives, L-rhamnosides and alkyl D-glucuronamides, where the alkyl chain is longer, is continued by a step c) trans-glycosylation carried out on this composition resulting from step b) or on one or more isolated / purified derivatives of this composition by means well known to those skilled in the art (eg silica gel column chromatography) , for example on L-rhamnoside derivatives, in the presence of an alcohol of formula R'OH, linear or branched, saturated or unsaturated, where R 'is composed of 2 to 22, preferably 8 to 18, preferably 12 at 18, carbon atoms.
- the alcohol R'OH is selected from the group consisting of linear, saturated or unsaturated fatty alcohols such as dodecanol and oleic alcohol.
- This trans-glycosylation step c) is carried out, for example, by introducing into the reaction medium resulting from step b) from 2 to 50 molar equivalents of an alcohol of formula R'OH as defined above, and preferably 15 molar equivalents; 10 "3-10 molar equivalents of an acid catalyst as defined above, and preferably from 0.1 to 10 molar equivalents of alkyl sulfonic acid, and preferably 1 molar equivalent of methanesulfonic acid.
- reaction trans-glycosylation is then continued to recycle the short-chain alcohol ROH previously used for the formation of the composition rich in (n-alkyl) -n-alkyl L-iduronate, (n-alkyl) -n-alkyl-D
- the reaction is carried out for 1 hour to 24 hours at a temperature preferably of 70 ° C. and under reduced pressure for the recycling of the above-mentioned alcohol.
- product derived from L-acid iduronic acid and D-glucuronic acid in the form of amides and rhamnose in the form of glycoside such as a hydrophone agent, a non-ionic detergent or an emulsifying agent.
- a neutralization step d) of the reaction medium resulting from stage c), once brought back to ambient temperature and at atmospheric pressure, can be carried out in the presence of (i) water and (ii) an M (OH) x base in which M is an alkali or alkaline earth metal, and x is valence.
- This step d) is carried out, for example, by introducing into the reaction medium resulting from stage c), once brought back to room temperature and at atmospheric pressure, from 0 to 19 molar equivalents of an aqueous solution containing a base of M (OH) x formula as defined above, and preferably 2.2 equivalents of a solution of sodium hydroxide (NaOH) 1 N; from 100 to 1000 molar equivalents of water and preferably 780 molar equivalents. Then, the whole is heated to 80 ° C with vigorous stirring for 15 min. Once the mixture has returned to room temperature, the aqueous phase is separated from the organic phase. The latter is finally dried by azeotropic distillation of the water using butanol.
- the excess alcohol of formula R'OH present in the organic crude may be partially or completely removed by molecular distillation. After a possible purification by chromatography on silica gel (ChbC / MeOH 97: 3 then 96: 4 then 90:10), a product mixture is obtained.
- the mass composition is about 10% alkyl L-iduronamides, 50% alkyl L-rhamnosides, and 40% alkyl D-glucuronamides.
- compositions thus formed by the process of the invention constitute useful products derived from L-iduronic acid and D-glucuronic acid in the form of amides and rhamnose in the form of glycosides, such as emulsifiers having anti-bacterial and / or antifungal properties at the concentrations used for emulsion formation.
- the present invention also relates to a composition obtained by a method according to the invention.
- the compositions of the invention consist of L-iduronic acid derivatives and D-glucuronic acid in the form of amides and rhamnose in glycoside form.
- the amide derivatives of the acid D-glucuronic acid are in the form of both pyranosides (6-membered ring) and furanosides (5-membered rings), whereas amide derivatives of L-iduronic acid and L-rhamnose glycosides are exclusively in the form of pyranoside.
- compositions of the invention are considered as emulsifiers for water-in-oil (W / O) or oil-in-water (O / W) emulsions. .
- they may have antibacterial and antifungal properties.
- the present invention also relates to the use of a composition according to the invention as a surfactant.
- said surfactant is selected from the group consisting of solubilizing, hydrotropic, wetting, foaming, emulsifying, emulsifying and / or detergent agents.
- composition according to the invention is also the use of a composition according to the invention as an antibacterial and / or antifungal agent.
- the present invention also relates to a surfactant comprising a composition according to the invention.
- Said surfactant may have the following properties:
- the present invention also relates to antifungal and / or antibacterial comprising a composition according to the invention.
- the process of the invention leads to novel surfactant compositions using exclusively biobased raw materials (ulvan, green algae) or biocompatible / biodegradable raw materials:
- the process of the invention thus makes it possible to produce compositions derived from L-iduronic acid and D-glucuronic acid in the form of amides and rhamnose in the form of glycoside which have the advantage of forming water emulsions. in oil (W / O) and oil in water (W / O) very stable in comparison with commercial emulsifiers, and possess antibacterial and antifungal properties at the concentrations used for the formation of emulsions.
- the process of the invention makes it possible at the same time to reduce the production costs of the surfactant compositions and to propose new compositions with a view to improving performance (emulsifying properties in particular).
- the presence of uronic sugars and rhamnose contributes to interesting biological activities in addition to surfactant properties.
- the presence of rhamnoside in the surfactant composition can therefore provide valuable biological activities in several fields and in particular in cosmetics.
- Other advantages may still appear to those skilled in the art on reading the examples below, illustrated by the appended figures, given for illustrative purposes.
- Figure 1 shows the measurement of the emulsifying power of the surfactant composition UlvC 4 Ni2 (A) W / O emulsion and (B) O / W emulsion, in comparison with commercial references Montanov ® and Xyliance ® .
- EXAMPLE 1 METHOD FOR OBTAINING COMPOSITIONS BASED ON ALKYL IDURONAMIDES, ALKYL D-GLUCURONAMIDES AND ALKYL L-RHAMNOSIDES FROM ULVANES
- pH 0.5 M hydrochloric acid
- the temperature of the medium was lowered to 60 ° C before adding 3 molar equivalents of C12H25NH2 dodecylamine (34.21 mmol, 7.86 grams) necessary to increase the pH to 8.5.
- the butanol was evaporated while reducing the pressure of 150 mbar at 6 mbar under a period of 1 hour.
- the medium was left under reduced pressure of 6 mbar and at 65 ° C. for 1.5 hours to ensure the evaporation of the traces of butanol which have formed.
- the residue obtained was taken up in diethyl ether and then filtered on sintered and rinsed several times with diethyl ether to remove the salts and the unreacted starting sugar.
- the filtrate (containing butyl rhamnoside, dodecyl glucuronamides and iduronamides) is concentrated in vacuo to give a dark brown oil.
- the surfactant composition UlvC 4 Ni 2 is then formed of n- (12-dodecyl) -n-butyl ⁇ -D-glucurofuranosiduronamide (47%), n- (12-dodecyl) -n-butyl ⁇ -D-glucuropyranosiduronamide (26%), n- (12-dodecyl) -n-butyl ⁇ -D-glucuropyranosiduronamide (7%), n- (12-dodecyl) -n-butyl aL-iduronopyranosiduronamide (20%).
- the proportions of the form furanose (a) and pyranose forms (a and ⁇ ) in the mixtures UlvC 4 Ni2 made it possible to evaluate a ratio pyranose / furanose.
- the value of the pyranose / furanose ratio is of the order of 1 .12 for the mixture UlvC 4 Ni2 indicating that the pyranose forms (a and ⁇ ) of n-dodecyl n-butyl D-glucuronamide and n-dodecyl n-butyl L-iduronamide are predominant with respect to the form furanose of n dodecyl n-butyl D-glucuronamide.
- N-Butyl ⁇ -Lhamnopyranoside (0.5 g, 2.27 mmol, 1 equiv.) Separated from the surfactant composition UlvC 4 Ni 2 by silica gel column chromatography was taken up in dodecanol (15 equiv.) In the presence of an equivalent of AMS (2.27 mmol, 148 ⁇ ). The transglycosylation was then carried out for 3 hours at 65 ° C. under reduced pressure (6 mbar) in a sufficiently diluted medium in order to avoid degradation of the butyl rhamnoside. At the end of the reaction, the reaction medium was allowed to cool and then neutralized with a solution of NaOH (0.1 M).
- the interfacial properties of the surfactant composition UlvC 4 Ni 2 were evaluated via the measurement of oil-water interfacial tensions.
- the surfactants were solubilized in sunflower oil at concentrations ranging from 0.12 to 0.46 g / L. In order to promote the solubility of the surfactants in the oil, the solutions were left in an ultrasonic bath for 10 minutes at 50 ° C. The interfacial tension measurements were made between Milli-Q water and the sample solutions in the oil.
- Measurements of the voltages at the interface between the oil and the water were carried out at 25 ° C. with a ring tensiometer (Kruss, model K 100C).
- the ring used was platinum iridium calibrated suspended horizontally. Before each measurement, the ring was thoroughly cleaned and flame dried.
- the bucket for sample is a cylindrical glass container placed in a thermoregulated chamber.
- the interfacial tension between sunflower oil (Carrefour brand) and water at 25 ° C varied between 24.71 and 25.04 mN / m.
- the apparatus For each concentration of the surfactant composition, the apparatus initially measured the surface tension of the sunflower oil containing the surfactant (low density liquid) and then the surface tension of the water (high density liquid). Finally, the oil was gently added to the water, while avoiding the formation of bubbles, the device began to measure the interfacial tension between sunflower oil and water (average of 10 measurements).
- the surfactant composition UlvC 4 Ni2 is capable of reducing the interfacial tension to a value of 10.32 mN / m at a concentration of 0.46 g / L to give the composition emulsifying powers.
- EXAMPLE 3 MEASURING THE EMULSIFYING POWER OF SURFACE-FREE COMPOSITIONS BASED ON L-IDURONAMIDES OF ALKYL AND D-GLUCURONAMIDES OF ALKYL FROM ULVANES
- the stability of the two types of O / W emulsions and W / O were evaluated by considering the two water / oil ratios 75/25 and 25/75 respectively in round bottom graduated tubes, 0.5% of the surfactant product is introduced ( 20 mg). Sunflower oil was introduced (1 or 3 mL), then the surfactants were solubilized in an ultrasonic bath for 10 minutes at 50 ° C. After solubilization of the emulsifier, the ultrapure water was added (1 or 3 ml).
- the two phases were then emulsified using an Ultraturraxika T18 basic ® homogenizer for 10 minutes at 1000 rpm.
- the emulsion was placed in a bath thermostated at 20 ° C.
- Figure 1 shows the results of analysis of the emulsifying power of the compositions of the invention.
- the surfactant composition UlvC 4 Ni 2 derived from dodecylamine has led to an O / W emulsion characterized by a high stability ranging from several weeks to several months.
- the W / O emulsion formed by the product UlvC 4 Ni 2 is very stable.
- EXAMPLE 4 ANTIBACTERIAL ACTIVITY OF SURFACTANT COMPOSITIONS BASED ON L-IDURONAMIDES OF ALKYL, OF D- ALKYL GLUCURONAMIDES AND ALKYL L-RHAMNOSIDES FROM ULVANES
- Protocol A Diffusion Method on Agar in Petri dishes
- the culture medium used was a mixture of 21 g / L Muller Hinton Broth and 10 g / L agar in water. This mixture was stirred and allowed to boil. Then, a step of autoclaving this mixture, for 30 minutes, was necessary in order to sterilize it before any manipulation. This culture medium was poured, hot, into petri dishes and then allowed to cool.
- the bacterial strains used were Pseudomonas aeruginoa,
- Escherichia coli, Enterococcus faecium and Staphylococcus aureus in addition to the fungal strain Candida albicans. June 10 bacteria were collected and transferred in a 0.9% NaCl solution. Each petri dish, containing Muller Hinton medium, was flooded with a different bacterial suspension.
- the positive controls used were ampicillin-soaked disks for
- Escherichia coli and Enterococcus faecium ceftazidime disks for Pseudomonas aeruginosa and vancomycin disks for Staphylococcus aureus.
- the Petri dishes were finally incubated at 37 ° C. in the oven for 24 hours.
- the antibacterial activity was evaluated by measuring the clarification zone in mm around the place of deposition of the different concentrations of the RhamOC 4 solution to be tested.
- Rhamnoside RhamOC 4 exhibited a very good ability to inhibit the growth of gram-positive bacteria Staphylococcus aureus and yeast Candida albicans. Its potency against Enterococcus faecium (6 mm at 5 mg.mL "1 ) was average, and rhamnoside RhamOC 4 showed an inhibitory activity of the gram negative bacterium Escherichia coli at concentrations 2.5 and 5 mg.mL " 1 with a weak inhibitory capacity of the growth of Pseudomonas aeruginosa.
- Protocol B Method for Evaluating Number of Living Bacteria The antibacterial and antifungal activities of the surfactant composition UlvC 4 Ni 2 were evaluated. In this context, the ability of this monosaccharide surfactant composition to kill bacteria has been studied by counting the number of living bacteria on Muller-Hinton agar.
- the inoculum was prepared at a turbidity equivalent to 0.5 MacFarland (Biomérieux France), then diluted to 1/100 (10 6 CFU / ml)
- each tube of the surfactant dilutions 1 ml of the bacterial inoculum was added. After incubation for 24 h at 36 ° C., 100 ⁇ l of each clear tube was spread on the surface of a Muller-Hinton agar followed by incubation for 24 hours at 37 ° C.
- the percentage of living bacteria was calculated: ⁇ 0 / ⁇ ⁇ 100.
- the minimum concentration of 100% inhibition of Enterococcus faecium and Candida albicans was of the order of 1.58 mg.mL -1 for the monosaccharide surfactant composition based on D-glucuronic and L-iduronic acids.
- very high concentrations of UlvC 4 Ni2 were required to 100% inhibit both these bacteria showing that UlvC 4 Ni2 (25.375 mg.mL "1 ) has a low antibacterial power against both types of bacteria.
- the hydrophobic carbon chain could interact with the lipid membrane of the gram-positive bacterium thus promoting its deformation and subsequently bacterial cell death (Reis et al., J. Brazilian Chem. Soc., 19 (6), 1065-1072, 2008) [12].
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FR1662342A FR3060005A1 (fr) | 2016-12-12 | 2016-12-12 | Procede de preparation de compositions tensioactives comprenant des l-iduronamides, d-glucuronamides et l-rhamnosides d'alkyle a partir d'ulvanes |
PCT/FR2017/053501 WO2018109348A1 (fr) | 2016-12-12 | 2017-12-11 | Procédé de préparation de compositions tensioactives comprenant des l-iduronamides, d-glucuronamides et l-rhamnosides d'alkyle à partir d'ulvanes |
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EP17821978.8A Withdrawn EP3551640A1 (fr) | 2016-12-12 | 2017-12-11 | Procédé de préparation de compositions tensioactives comprenant des l-iduronamides, d-glucuronamides et l-rhamnosides d'alkyle à partir d'ulvanes |
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US (1) | US20200045962A1 (fr) |
EP (1) | EP3551640A1 (fr) |
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US2670345A (en) | 1949-04-05 | 1954-02-23 | Charles L Mehltretter | Substituted gluconamides |
ES2103830T3 (es) | 1990-10-12 | 1997-10-01 | Procter & Gamble | Procedimiento para preparar n-alquilpolihidroxiaminas y amidas de acidos grasos de las mismas en disolventes hidroxi. |
ES2111077T3 (es) | 1991-07-26 | 1998-03-01 | Procter & Gamble | Procedimiento para preparar n-alquilpolihidroxialquilaminas en disolventes acuosos/hidroxi. |
GB9121279D0 (en) | 1991-10-08 | 1991-11-20 | Cerestar Holding Bv | Process for the production of aminopolyols |
US5872111A (en) | 1997-05-19 | 1999-02-16 | Lever Brothers Company, Division Of Conopco, Inc. | Compositions comprising glycosylamide surfactants |
FR2840306B1 (fr) | 2002-05-29 | 2005-07-01 | Ct D Etude Et De Valorisation | Derives d'acide(alkyl d-mannopyranoside) uronique, des procedes pour leur preparation, ainsi que leurs applications |
US7655611B2 (en) | 2004-12-14 | 2010-02-02 | The University Of Houston System | Structural family on non-ionic carbohydrate based surfactants (NICBS) and a novel process for their synthesis |
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- 2017-12-11 US US16/468,717 patent/US20200045962A1/en not_active Abandoned
- 2017-12-11 EP EP17821978.8A patent/EP3551640A1/fr not_active Withdrawn
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