BE509837A - - Google Patents
Info
- Publication number
- BE509837A BE509837A BE509837DA BE509837A BE 509837 A BE509837 A BE 509837A BE 509837D A BE509837D A BE 509837DA BE 509837 A BE509837 A BE 509837A
- Authority
- BE
- Belgium
- Prior art keywords
- acetoxy
- compound
- epoxide
- methyl
- acid
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 98
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 65
- 239000002253 acid Substances 0.000 claims description 52
- 238000002360 preparation method Methods 0.000 claims description 48
- 150000002118 epoxides Chemical class 0.000 claims description 38
- 238000000034 method Methods 0.000 claims description 29
- PNEYBMLMFCGWSK-UHFFFAOYSA-N AI2O3 Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 28
- 230000000875 corresponding Effects 0.000 claims description 28
- -1 ergosterol D epoxide Chemical class 0.000 claims description 26
- 239000002904 solvent Substances 0.000 claims description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 18
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 16
- DNVPQKQSNYMLRS-LNHMRCHQSA-N Ergosterol Natural products O[C@@H]1CC=2[C@@](C)([C@@H]3C([C@H]4[C@@](C)([C@H]([C@@H](/C=C/[C@H](C(C)C)C)C)CC4)CC3)=CC=2)CC1 DNVPQKQSNYMLRS-LNHMRCHQSA-N 0.000 claims description 14
- 150000002148 esters Chemical class 0.000 claims description 14
- 239000003463 adsorbent Substances 0.000 claims description 13
- KRVSOGSZCMJSLX-UHFFFAOYSA-L Chromic acid Chemical compound O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 claims description 12
- XSMGJKKUFBTARU-MJXYXNKESA-N Ergosterol D Chemical compound C1[C@@H](O)CC[C@]2(C)C3=CC[C@]4(C)[C@@H]([C@H](C)/C=C/[C@H](C)C(C)C)CC[C@H]4C3=CC[C@H]21 XSMGJKKUFBTARU-MJXYXNKESA-N 0.000 claims description 10
- 150000004967 organic peroxy acids Chemical class 0.000 claims description 10
- HCHKCACWOHOZIP-UHFFFAOYSA-N zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 10
- 230000002378 acidificating Effects 0.000 claims description 9
- 125000002252 acyl group Chemical group 0.000 claims description 9
- 125000003700 epoxy group Chemical group 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 7
- 229910052725 zinc Inorganic materials 0.000 claims description 7
- 239000011701 zinc Substances 0.000 claims description 7
- 238000009835 boiling Methods 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 6
- 230000003647 oxidation Effects 0.000 claims description 6
- 238000007254 oxidation reaction Methods 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- 239000004593 Epoxy Substances 0.000 claims description 5
- 125000000468 ketone group Chemical group 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- BFMNMQAWCBSBRV-ADGVWNIHSA-N CC(C)[C@@H](C)C=C[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CCC4CCCC[C@]4(C)[C@H]3CC[C@]12C Chemical compound CC(C)[C@@H](C)C=C[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CCC4CCCC[C@]4(C)[C@H]3CC[C@]12C BFMNMQAWCBSBRV-ADGVWNIHSA-N 0.000 claims description 4
- 150000003431 steroids Chemical class 0.000 claims description 4
- CHNRSYCQARCWBK-JDOOSZNNSA-N CC(C)[C@@H](C)C=C[C@@H](C)[C@H]1CC[C@H]2C=3CCC4CCCC[C@]4(C)C=3CC[C@]12C Chemical compound CC(C)[C@@H](C)C=C[C@@H](C)[C@H]1CC[C@H]2C=3CCC4CCCC[C@]4(C)C=3CC[C@]12C CHNRSYCQARCWBK-JDOOSZNNSA-N 0.000 claims description 3
- 125000004423 acyloxy group Chemical group 0.000 claims description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 3
- 210000004940 Nucleus Anatomy 0.000 claims description 2
- 229910052782 aluminium Inorganic materials 0.000 claims description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminum Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 2
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (N-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 claims 1
- FBVMQOYYGXIUEU-JINGVYKBSA-N C(C)(=O)OC1CC2CC[C@H]3[C@@H]4CC[C@H]([C@@H](CC[C@@H](C(=C)C)C)C)[C@]4(CC([C@@H]3[C@]2(CC1)C)=O)C Chemical compound C(C)(=O)OC1CC2CC[C@H]3[C@@H]4CC[C@H]([C@@H](CC[C@@H](C(=C)C)C)C)[C@]4(CC([C@@H]3[C@]2(CC1)C)=O)C FBVMQOYYGXIUEU-JINGVYKBSA-N 0.000 claims 1
- 125000004432 carbon atoms Chemical group C* 0.000 claims 1
- 238000005352 clarification Methods 0.000 claims 1
- 239000003638 reducing agent Substances 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 153
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 101
- 229920001098 polystyrene-block-poly(ethylene/propylene) Polymers 0.000 description 88
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 78
- 239000000243 solution Substances 0.000 description 68
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 66
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 66
- 238000002844 melting Methods 0.000 description 48
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 46
- 239000000203 mixture Substances 0.000 description 42
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 34
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 33
- 239000000047 product Substances 0.000 description 31
- 238000004458 analytical method Methods 0.000 description 30
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 26
- 238000001953 recrystallisation Methods 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 20
- 239000000155 melt Substances 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- 229960000583 Acetic Acid Drugs 0.000 description 18
- XCRBXWCUXJNEFX-UHFFFAOYSA-N Peroxybenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1 XCRBXWCUXJNEFX-UHFFFAOYSA-N 0.000 description 18
- 238000003756 stirring Methods 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 15
- MTHSVFCYNBDYFN-UHFFFAOYSA-N Diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 238000001914 filtration Methods 0.000 description 12
- 239000012362 glacial acetic acid Substances 0.000 description 11
- PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 11
- 239000003208 petroleum Substances 0.000 description 11
- 235000011118 potassium hydroxide Nutrition 0.000 description 11
- 229910052938 sodium sulfate Inorganic materials 0.000 description 11
- 235000011152 sodium sulphate Nutrition 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- 239000000727 fraction Substances 0.000 description 8
- 239000000523 sample Substances 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- 238000002425 crystallisation Methods 0.000 description 7
- 230000005712 crystallization Effects 0.000 description 7
- WGLPBDUCMAPZCE-UHFFFAOYSA-N trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 7
- BRMYZIKAHFEUFJ-UHFFFAOYSA-L Mercury(II) acetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 description 6
- 239000003518 caustics Substances 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 238000005292 vacuum distillation Methods 0.000 description 6
- YXHKONLOYHBTNS-UHFFFAOYSA-N diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L mgso4 Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- GLVYLTSKTCWWJR-UHFFFAOYSA-N 2-carbonoperoxoylbenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1C(O)=O GLVYLTSKTCWWJR-UHFFFAOYSA-N 0.000 description 4
- DNVPQKQSNYMLRS-APGDWVJJSA-N Ergosterol Chemical compound C1[C@@H](O)CC[C@]2(C)[C@@H](CC[C@@]3([C@@H]([C@H](C)/C=C/[C@H](C)C(C)C)CC[C@H]33)C)C3=CC=C21 DNVPQKQSNYMLRS-APGDWVJJSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- WRYNUJYAXVDTCB-UHFFFAOYSA-M acetyloxymercury Chemical compound CC(=O)O[Hg] WRYNUJYAXVDTCB-UHFFFAOYSA-M 0.000 description 4
- 238000007792 addition Methods 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 150000004702 methyl esters Chemical class 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 229920000647 polyepoxide Polymers 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M Sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- WPUJEWVVTKLMQI-UHFFFAOYSA-N benzene;ethoxyethane Chemical compound CCOCC.C1=CC=CC=C1 WPUJEWVVTKLMQI-UHFFFAOYSA-N 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 229940117975 chromium trioxide Drugs 0.000 description 3
- 239000002178 crystalline material Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000010828 elution Methods 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 230000004927 fusion Effects 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 230000001264 neutralization Effects 0.000 description 3
- CBENFWSGALASAD-UHFFFAOYSA-N ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 3
- 150000004965 peroxy acids Chemical class 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- HVYWMOMLDIMFJA-DPAQBDIFSA-N (3β)-Cholest-5-en-3-ol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- KPRGOTLNGIBVFL-GINZOMEDSA-N 7-Keto-DHEA Chemical group C1[C@@H](O)CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3C(=O)C=C21 KPRGOTLNGIBVFL-GINZOMEDSA-N 0.000 description 2
- BHQCQFFYRZLCQQ-OELDTZBJSA-N Cholic acid Chemical class C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 BHQCQFFYRZLCQQ-OELDTZBJSA-N 0.000 description 2
- WQLVFSAGQJTQCK-VKROHFNGSA-N Diosgenin Chemical compound O([C@@H]1[C@@H]([C@]2(CC[C@@H]3[C@@]4(C)CC[C@H](O)CC4=CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@@H](C)CO1 WQLVFSAGQJTQCK-VKROHFNGSA-N 0.000 description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N Phenethyl alcohol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000002026 chloroform extract Substances 0.000 description 2
- 235000019416 cholic acid Nutrition 0.000 description 2
- 150000001844 chromium Chemical class 0.000 description 2
- 238000010908 decantation Methods 0.000 description 2
- 150000002131 ergostadienes Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000006011 modification reaction Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000012454 non-polar solvent Substances 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000004576 sand Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 230000001225 therapeutic Effects 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- XNLICIUVMPYHGG-UHFFFAOYSA-N 2-Pentanone Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 1
- HIAJCGFYHIANNA-QIZZZRFXSA-N 3b-Hydroxy-5-cholenoic acid Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@@H](CCC(O)=O)C)[C@@]1(C)CC2 HIAJCGFYHIANNA-QIZZZRFXSA-N 0.000 description 1
- 210000000941 Bile Anatomy 0.000 description 1
- UTCNDDQZGMAJOY-JINGVYKBSA-N C(C)(=O)OC1CC2CC[C@H]3[C@@H]4CC[C@H]([C@@H](C=C[C@@H](C(C)C)C)C)[C@]4(CC([C@@H]3[C@]2(CC1)C)=O)C Chemical compound C(C)(=O)OC1CC2CC[C@H]3[C@@H]4CC[C@H]([C@@H](C=C[C@@H](C(C)C)C)C)[C@]4(CC([C@@H]3[C@]2(CC1)C)=O)C UTCNDDQZGMAJOY-JINGVYKBSA-N 0.000 description 1
- RZERMLCGRJKRCR-IAFKBQHOSA-N C(CC[C@@H](C)[C@H]1CC[C@H]2C3=CCC4CCCC[C@]4(C)C3=CC[C@]12C)(=O)O Chemical compound C(CC[C@@H](C)[C@H]1CC[C@H]2C3=CCC4CCCC[C@]4(C)C3=CC[C@]12C)(=O)O RZERMLCGRJKRCR-IAFKBQHOSA-N 0.000 description 1
- YBWPFLHAFLZVCE-IAFKBQHOSA-M C(CC[C@@H](C)[C@H]1CC[C@H]2C=3CCC4CCCC[C@]4(C)C=3CC[C@]12C)(=O)[O-] Chemical compound C(CC[C@@H](C)[C@H]1CC[C@H]2C=3CCC4CCCC[C@]4(C)C=3CC[C@]12C)(=O)[O-] YBWPFLHAFLZVCE-IAFKBQHOSA-M 0.000 description 1
- SLJSDFAOYWBALZ-UHFFFAOYSA-N C(Cl)(Cl)Cl.C(C)(=O)OCC.CC(=O)C.CO Chemical compound C(Cl)(Cl)Cl.C(C)(=O)OCC.CC(=O)C.CO SLJSDFAOYWBALZ-UHFFFAOYSA-N 0.000 description 1
- 229940107161 Cholesterol Drugs 0.000 description 1
- 239000004380 Cholic acid Substances 0.000 description 1
- MFYSYFVPBJMHGN-ZPOLXVRWSA-N Cortisone Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 MFYSYFVPBJMHGN-ZPOLXVRWSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- DGMKFQYCZXERLX-UHFFFAOYSA-N N(2)-benzoyl-N,N-dipropyl-α-glutamine Chemical compound CCCN(CCC)C(=O)C(CCC(O)=O)NC(=O)C1=CC=CC=C1 DGMKFQYCZXERLX-UHFFFAOYSA-N 0.000 description 1
- WKSGKUYVQIETQT-UYGRXWDCSA-N OC1CC2CC[C@H]3[C@@H]4CC[C@H]([C@@H](C=C[C@@H](C(C)C)C)C)[C@]4(CC([C@@H]3[C@]2(CC1)C)=O)C Chemical compound OC1CC2CC[C@H]3[C@@H]4CC[C@H]([C@@H](C=C[C@@H](C(C)C)C)C)[C@]4(CC([C@@H]3[C@]2(CC1)C)=O)C WKSGKUYVQIETQT-UYGRXWDCSA-N 0.000 description 1
- 241000690470 Plantago princeps Species 0.000 description 1
- GMBQZIIUCVWOCD-WWASVFFGSA-N Sarsapogenine Chemical compound O([C@@H]1[C@@H]([C@]2(CC[C@@H]3[C@@]4(C)CC[C@H](O)C[C@H]4CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@H](C)CO1 GMBQZIIUCVWOCD-WWASVFFGSA-N 0.000 description 1
- 229940083599 Sodium Iodide Drugs 0.000 description 1
- KIEOKOFEPABQKJ-UHFFFAOYSA-N Sodium dichromate Chemical compound [Na+].[Na+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KIEOKOFEPABQKJ-UHFFFAOYSA-N 0.000 description 1
- 229940032091 Stigmasterol Drugs 0.000 description 1
- HCXVJBMSMIARIN-MFBJGPNFSA-N Stigmasterol Natural products O[C@@H]1CC=2[C@@](C)([C@@H]3[C@H]([C@H]4[C@@](C)([C@H]([C@@H](/C=C/[C@@H](C(C)C)CC)C)CC4)CC3)CC=2)CC1 HCXVJBMSMIARIN-MFBJGPNFSA-N 0.000 description 1
- GMBQZIIUCVWOCD-MFRNJXNGSA-N Tigogenin Natural products O([C@@H]1[C@@H]([C@]2(CC[C@@H]3[C@@]4(C)CC[C@H](O)C[C@@H]4CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@@H](C)CO1 GMBQZIIUCVWOCD-MFRNJXNGSA-N 0.000 description 1
- SHIYKHFFMRDJJC-UHFFFAOYSA-L [Na+].[Na+].[O-]O[O-] Chemical compound [Na+].[Na+].[O-]O[O-] SHIYKHFFMRDJJC-UHFFFAOYSA-L 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000001919 adrenal Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 239000000538 analytical sample Substances 0.000 description 1
- 235000020127 ayran Nutrition 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 235000012970 cakes Nutrition 0.000 description 1
- 150000001721 carbon Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000002036 chloroform fraction Substances 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- OAIVIYSBZFEOIU-UHFFFAOYSA-N chloroform;propan-2-one Chemical compound CC(C)=O.ClC(Cl)Cl OAIVIYSBZFEOIU-UHFFFAOYSA-N 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 229960002471 cholic acid Drugs 0.000 description 1
- 239000002812 cholic acid derivative Substances 0.000 description 1
- 150000001842 cholic acids Chemical class 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
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Landscapes
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Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE509837A true BE509837A (nl) |
Family
ID=149137
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE509837D BE509837A (nl) |
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| Country | Link |
|---|---|
| BE (1) | BE509837A (nl) |
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0
- BE BE509837D patent/BE509837A/fr unknown
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