DEU0002026MA - - Google Patents

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Publication number

DEU0002026MA

DEU0002026MA DEU0002026MA DE U0002026M A DEU0002026M A DE U0002026MA DE U0002026M A DEU0002026M A DE U0002026MA

Authority

DE

Germany

Prior art keywords

fungus

testosterone

acetone

chloroform

oxytestosterone

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.)

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• MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 claims description 14
• 238000000034 method Methods 0.000 claims description 8
• 229960003604 testosterone Drugs 0.000 claims description 7
• 241000233866 Fungi Species 0.000 claims description 6
• 150000003431 steroids Chemical class 0.000 claims description 6
• 102000004190 Enzymes Human genes 0.000 claims description 4
• 108090000790 Enzymes Proteins 0.000 claims description 4
• 241000235388 Mucorales Species 0.000 claims description 4
• 230000001590 oxidative effect Effects 0.000 claims description 4
• 241001623528 Mucor circinelloides f. griseocyanus Species 0.000 claims description 3
• 241000235395 Mucor Species 0.000 claims description 2
• 238000000605 extraction Methods 0.000 claims description 2
• 239000007800 oxidant agent Substances 0.000 claims description 2
• 241000894007 species Species 0.000 claims description 2
• 238000002360 preparation method Methods 0.000 claims 1
• 238000000926 separation method Methods 0.000 claims 1
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
• 239000002904 solvent Substances 0.000 description 6
• 239000000284 extract Substances 0.000 description 5
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
• 238000001704 evaporation Methods 0.000 description 2
• 230000008020 evaporation Effects 0.000 description 2
• 238000001914 filtration Methods 0.000 description 2
• 239000001963 growth medium Substances 0.000 description 2
• 238000004519 manufacturing process Methods 0.000 description 2
• 239000001301 oxygen Substances 0.000 description 2
• 229910052760 oxygen Inorganic materials 0.000 description 2
• 238000001953 recrystallisation Methods 0.000 description 2
• 239000000126 substance Substances 0.000 description 2
• 238000009423 ventilation Methods 0.000 description 2
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
• 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 1
• 239000005909 Kieselgur Substances 0.000 description 1
• 229910002651 NO3 Inorganic materials 0.000 description 1
• NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
• 240000008042 Zea mays Species 0.000 description 1
• 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
• 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
• 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
• 239000003795 chemical substances by application Substances 0.000 description 1
• 229940117975 chromium trioxide Drugs 0.000 description 1
• WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
• GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 1
• 239000004927 clay Substances 0.000 description 1
• 150000001875 compounds Chemical class 0.000 description 1
• 235000005822 corn Nutrition 0.000 description 1
• 239000008121 dextrose Substances 0.000 description 1
• 238000002845 discoloration Methods 0.000 description 1
• 238000004821 distillation Methods 0.000 description 1
• 238000001035 drying Methods 0.000 description 1
• 230000002255 enzymatic effect Effects 0.000 description 1
• 150000002148 esters Chemical class 0.000 description 1
• 239000000706 filtrate Substances 0.000 description 1
• 238000004362 fungal culture Methods 0.000 description 1
• 239000001257 hydrogen Substances 0.000 description 1
• 229910052739 hydrogen Inorganic materials 0.000 description 1
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
• 238000011534 incubation Methods 0.000 description 1
• 238000002329 infrared spectrum Methods 0.000 description 1
• 239000000543 intermediate Substances 0.000 description 1
• XCOBTUNSZUJCDH-UHFFFAOYSA-B lithium magnesium sodium silicate Chemical compound [Li+].[Li+].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Na+].[Na+].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3 XCOBTUNSZUJCDH-UHFFFAOYSA-B 0.000 description 1
• 230000008018 melting Effects 0.000 description 1
• 238000002844 melting Methods 0.000 description 1
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
• 239000000203 mixture Substances 0.000 description 1
• 230000003287 optical effect Effects 0.000 description 1
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
• 239000011734 sodium Substances 0.000 description 1
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
• 235000017557 sodium bicarbonate Nutrition 0.000 description 1
• 229910000033 sodium borohydride Inorganic materials 0.000 description 1
• 239000012279 sodium borohydride Substances 0.000 description 1
• 239000007787 solid Substances 0.000 description 1
• 238000010561 standard procedure Methods 0.000 description 1
• 238000003756 stirring Methods 0.000 description 1
• 239000008399 tap water Substances 0.000 description 1
• 235000020679 tap water Nutrition 0.000 description 1
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1