BE424905A - - Google Patents

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Publication number: BE424905A
Authority: BE; Belgium
Prior art keywords: acid; solution; products; desc; acids
Prior art date

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Publication of BE424905A publication Critical patent/BE424905A/fr

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150000001875 compounds Chemical class 0.000 claims description 15
-1 polycarbonyl Polymers 0.000 claims description 10
230000002378 acidificating Effects 0.000 claims description 6
238000000034 method Methods 0.000 claims description 6
230000001264 neutralization Effects 0.000 claims description 5
238000000926 separation method Methods 0.000 claims description 4
239000000126 substance Substances 0.000 claims description 3
239000000243 solution Substances 0.000 description 30
239000000047 product Substances 0.000 description 20
RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
230000003647 oxidation Effects 0.000 description 17
238000007254 oxidation reaction Methods 0.000 description 17
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 13
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 12
239000003613 bile acid Substances 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
239000002253 acid Substances 0.000 description 11
229960000583 Acetic Acid Drugs 0.000 description 9
239000000203 mixture Substances 0.000 description 8
239000011780 sodium chloride Substances 0.000 description 7
KRVSOGSZCMJSLX-UHFFFAOYSA-L Chromic acid Chemical compound O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
150000007513 acids Chemical class 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 6
239000003795 chemical substances by application Substances 0.000 description 6
RUVUHIUYGJBLGI-XJZKHKOHSA-N β-sitostenone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CC[C@@H](CC)C(C)C)[C@@]1(C)CC2 RUVUHIUYGJBLGI-XJZKHKOHSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
210000004940 Nucleus Anatomy 0.000 description 5
GGCLNOIGPMGLDB-GYKMGIIDSA-N cholest-5-en-3-one Chemical compound C1C=C2CC(=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 GGCLNOIGPMGLDB-GYKMGIIDSA-N 0.000 description 5
239000012362 glacial acetic acid Substances 0.000 description 5
238000002844 melting Methods 0.000 description 5
239000007800 oxidant agent Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
239000007857 degradation product Substances 0.000 description 4
VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
150000002576 ketones Chemical class 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
WGLPBDUCMAPZCE-UHFFFAOYSA-N trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 4
HCHKCACWOHOZIP-UHFFFAOYSA-N zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
AEMFNILZOJDQLW-QAGGRKNESA-N Androstenedione Chemical class O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 AEMFNILZOJDQLW-QAGGRKNESA-N 0.000 description 3
DUIOPKIIICUYRZ-UHFFFAOYSA-N Semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 3
230000001476 alcoholic Effects 0.000 description 3
150000001735 carboxylic acids Chemical class 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
238000003776 cleavage reaction Methods 0.000 description 3
239000000284 extract Substances 0.000 description 3
BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 3
238000000260 fractional sublimation Methods 0.000 description 3
229910052736 halogen Inorganic materials 0.000 description 3
239000001301 oxygen Substances 0.000 description 3
MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 3
229910052760 oxygen Inorganic materials 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
230000001131 transforming Effects 0.000 description 3
RAJWOBJTTGJROA-RNQTWYFASA-N Androstanedione Chemical compound C1C(=O)CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC21 RAJWOBJTTGJROA-RNQTWYFASA-N 0.000 description 2
229960005471 Androstenedione Drugs 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N Perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
210000002356 Skeleton Anatomy 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
DBJUEJCZPKMDPA-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O DBJUEJCZPKMDPA-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
238000007792 addition Methods 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
230000015556 catabolic process Effects 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
229940117975 chromium trioxide Drugs 0.000 description 2
230000004059 degradation Effects 0.000 description 2
238000006731 degradation reaction Methods 0.000 description 2
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
125000005594 diketone group Chemical group 0.000 description 2
238000007865 diluting Methods 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000001640 fractional crystallisation Methods 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
239000008079 hexane Substances 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
150000002431 hydrogen Chemical class 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
230000001590 oxidative Effects 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
238000000746 purification Methods 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
239000002904 solvent Substances 0.000 description 2
238000001256 steam distillation Methods 0.000 description 2
HCXVJBMSMIARIN-PHZDYDNGSA-N stigmasterol 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)/C=C/[C@@H](CC)C(C)C)[C@@]1(C)CC2 HCXVJBMSMIARIN-PHZDYDNGSA-N 0.000 description 2
238000005292 vacuum distillation Methods 0.000 description 2
UIMGHSAOLFTOBF-UHFFFAOYSA-N 10,13-dimethyl-17-(6-methylheptan-2-yl)-2,3,6,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol Chemical compound C1CC2=CC(O)CCC2(C)C2C1C1CCC(C(C)CCCC(C)C)C1(C)CC2 UIMGHSAOLFTOBF-UHFFFAOYSA-N 0.000 description 1
KXGVEGMKQFWNSR-GPTTVZJUSA-N 4-[(3R,12S)-3,12-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid Chemical compound C1CC2C[C@H](O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)[C@@H](O)C2 KXGVEGMKQFWNSR-GPTTVZJUSA-N 0.000 description 1
XMRPGKVKISIQBV-BJMCWZGWSA-N 5α-Dihydroprogesterone Chemical compound C([C@@H]1CC2)C(=O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](C(=O)C)[C@@]2(C)CC1 XMRPGKVKISIQBV-BJMCWZGWSA-N 0.000 description 1
PESKGJQREUXSRR-UXIWKSIVSA-N 5α-cholestan-3-one Chemical compound C([C@@H]1CC2)C(=O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@H](C)CCCC(C)C)[C@@]2(C)CC1 PESKGJQREUXSRR-UXIWKSIVSA-N 0.000 description 1
XWJTYEGVQBFZHI-IMPNNSMHSA-N Apocholic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1C2=C2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 XWJTYEGVQBFZHI-IMPNNSMHSA-N 0.000 description 1
DOXNEWWEWLQJIH-OZWOBKTPSA-N BrC1C([C@@H]([C@]2(CC[C@@H]3[C@]4(CCCCC4CC[C@H]3[C@H]12)C)C)[C@H](C)CCCC(C)C)=O Chemical compound BrC1C([C@@H]([C@]2(CC[C@@H]3[C@]4(CCCCC4CC[C@H]3[C@H]12)C)C)[C@H](C)CCCC(C)C)=O DOXNEWWEWLQJIH-OZWOBKTPSA-N 0.000 description 1
MIQWSUWMPONGPJ-ZWUTWDRESA-N ClC(=C(C)C(CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CCC4CCCC[C@]4(C)[C@H]3CC[C@]12C)=O)Cl Chemical compound ClC(=C(C)C(CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CCC4CCCC[C@]4(C)[C@H]3CC[C@]12C)=O)Cl MIQWSUWMPONGPJ-ZWUTWDRESA-N 0.000 description 1
210000004246 Corpus Luteum Anatomy 0.000 description 1
JLTDJTHDQAWBAV-UHFFFAOYSA-N Dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
229940088597 Hormone Drugs 0.000 description 1
OZWKMVRBQXNZKK-UHFFFAOYSA-N Ketorolac Chemical class OC(=O)C1CCN2C1=CC=C2C(=O)C1=CC=CC=C1 OZWKMVRBQXNZKK-UHFFFAOYSA-N 0.000 description 1
JEHCHYAKAXDFKV-UHFFFAOYSA-J Lead(IV) acetate Chemical compound CC(=O)O[Pb](OC(C)=O)(OC(C)=O)OC(C)=O JEHCHYAKAXDFKV-UHFFFAOYSA-J 0.000 description 1
SMEROWZSTRWXGI-HVATVPOCSA-N Lithocholic acid Chemical compound C([C@H]1CC2)[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)CC1 SMEROWZSTRWXGI-HVATVPOCSA-N 0.000 description 1
ZJRFCEIUGPXQPH-PBDHEXIJSA-N O=C1CC2CC[C@H]3[C@@H]4CC[C@H]([C@@H](C=CC(=O)O)C)[C@]4(CC[C@@H]3[C@]2(CC1)C)C Chemical class O=C1CC2CC[C@H]3[C@@H]4CC[C@H]([C@@H](C=CC(=O)O)C)[C@]4(CC[C@@H]3[C@]2(CC1)C)C ZJRFCEIUGPXQPH-PBDHEXIJSA-N 0.000 description 1
WRMNZCZEMHIOCP-UHFFFAOYSA-N Phenethyl alcohol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 1
HKOOXMFOFWEVGF-UHFFFAOYSA-N Phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
229920001470 Polyketone Polymers 0.000 description 1
OFLXLNCGODUUOT-UHFFFAOYSA-N acetohydrazonic acid Chemical class C\C(O)=N\N OFLXLNCGODUUOT-UHFFFAOYSA-N 0.000 description 1
239000003929 acidic solution Substances 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910001516 alkali metal iodide Inorganic materials 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
HAMNKKUPIHEESI-UHFFFAOYSA-N aminoguanidine Chemical compound NNC(N)=N HAMNKKUPIHEESI-UHFFFAOYSA-N 0.000 description 1
BRWIZMBXBAOCCF-UHFFFAOYSA-N aminothiourea Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 description 1
239000002585 base Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
238000005893 bromination reaction Methods 0.000 description 1
230000003197 catalytic Effects 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
230000000875 corresponding Effects 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000005712 crystallization Effects 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
150000003997 cyclic ketones Chemical class 0.000 description 1
YADSGOSSYOOKMP-UHFFFAOYSA-N dioxolead Chemical compound O=[Pb]=O YADSGOSSYOOKMP-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
238000005194 fractionation Methods 0.000 description 1
239000005556 hormone Substances 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
AVXURJPOCDRRFD-UHFFFAOYSA-N hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
125000000468 ketone group Chemical group 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
238000010525 oxidative degradation reaction Methods 0.000 description 1
238000007248 oxidative elimination reaction Methods 0.000 description 1
NPDODHDPVPPRDJ-UHFFFAOYSA-N permanganate Chemical compound [O-][Mn](=O)(=O)=O NPDODHDPVPPRDJ-UHFFFAOYSA-N 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
229940067157 phenylhydrazine Drugs 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000000376 reactant Substances 0.000 description 1
150000007659 semicarbazones Chemical class 0.000 description 1
230000001568 sexual Effects 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000000859 sublimation Methods 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
KZJWDPNRJALLNS-VJSFXXLFSA-N β-Sitosterol 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)CC[C@@H](CC)C(C)C)[C@@]1(C)CC2 KZJWDPNRJALLNS-VJSFXXLFSA-N 0.000 description 1

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Steroid Compounds (AREA)

BE424905D BE424905A (fi)

Publications (1)

Publication Number	Publication Date
BE424905A true BE424905A (fi)

Family

ID=86023

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BE424905D BE424905A (fi)

Country Status (1)

Country	Link
BE (1)	BE424905A (fi)

0
- BE BE424905D patent/BE424905A/fr unknown

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