BE546747A

BE546747A -

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Publication number: BE546747A
Authority: BE; Belgium
Prior art keywords: steroid; keto; androstene; weight; parts
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English (en)

French (fr)

Publication of BE546747A publication Critical patent/BE546747A/fr

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238000000034 method Methods 0.000 claims description 31
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 30
-1 lithium aluminum hydride Chemical compound 0.000 claims description 21
150000001875 compounds Chemical class 0.000 claims description 18
125000003118 aryl group Chemical group 0.000 claims description 7
IHHKCVMULSSIQO-DPKMYYEESA-N (8S,9S,10R,13R,14S)-3-hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,17-dodecahydrocyclopenta[a]phenanthren-16-one Chemical compound C[C@@]12CC(=O)C[C@H]1[C@@H]1CC=C3CC(O)CC[C@]3(C)[C@H]1CC2 IHHKCVMULSSIQO-DPKMYYEESA-N 0.000 claims description 6
150000002148 esters Chemical class 0.000 claims description 6
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 6
AKRBLZKRYPEVIK-RVKDVGHASA-N (8R,9S,10R,13S,14S)-3,17-dihydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,17-dodecahydrocyclopenta[a]phenanthren-16-one Chemical compound C[C@]12CC[C@H]3[C@@H](CC=C4CC(O)CC[C@]34C)[C@@H]1CC(=O)C2O AKRBLZKRYPEVIK-RVKDVGHASA-N 0.000 claims description 5
239000012280 lithium aluminium hydride Substances 0.000 claims description 4
239000012279 sodium borohydride Substances 0.000 claims description 4
229910000033 sodium borohydride Inorganic materials 0.000 claims description 4
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 3
230000001476 alcoholic effect Effects 0.000 claims description 3
150000008044 alkali metal hydroxides Chemical class 0.000 claims description 3
JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 claims description 3
OGNVQLDIPUXYDH-ZPKKHLQPSA-N (2R,3R,4S)-3-(2-methylpropanoylamino)-4-(4-phenyltriazol-1-yl)-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid Chemical compound CC(C)C(=O)N[C@H]1[C@H]([C@H](O)[C@H](O)CO)OC(C(O)=O)=C[C@@H]1N1N=NC(C=2C=CC=CC=2)=C1 OGNVQLDIPUXYDH-ZPKKHLQPSA-N 0.000 claims description 2
SBNLPRGISFUZQE-VMXHOPILSA-N (8s,9s,10r,13s,14s)-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthrene Chemical group C1C=C2CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CCC[C@@]1(C)CC2 SBNLPRGISFUZQE-VMXHOPILSA-N 0.000 claims description 2
NBOGSUYFHPMYOO-PGDLUIMUSA-N C(C1=CC=CC=C1)OC1CC2=CC[C@H]3[C@@H]4CC(C[C@@]4(C)CC[C@@H]3[C@]2(CC1)C)=O Chemical compound C(C1=CC=CC=C1)OC1CC2=CC[C@H]3[C@@H]4CC(C[C@@]4(C)CC[C@@H]3[C@]2(CC1)C)=O NBOGSUYFHPMYOO-PGDLUIMUSA-N 0.000 claims description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
125000004185 ester group Chemical group 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
230000007062 hydrolysis Effects 0.000 claims description 2
238000006460 hydrolysis reaction Methods 0.000 claims description 2
ZKQNRRLCBJUEBC-UHFFFAOYSA-N oxo-[[1-[[4-(oxoazaniumylmethylidene)pyridin-1-yl]methyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CN1C=CC(=C[NH+]=O)C=C1 ZKQNRRLCBJUEBC-UHFFFAOYSA-N 0.000 claims description 2
DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 claims description 2
KVUXYQHEESDGIJ-UHFFFAOYSA-N 10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthrene-3,16-diol Chemical compound C1CC2CC(O)CCC2(C)C2C1C1CC(O)CC1(C)CC2 KVUXYQHEESDGIJ-UHFFFAOYSA-N 0.000 claims 1
LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 claims 1
BDLYNEBJXDHISO-DHSGYYQHSA-N C(C)(=O)OC1CC2=CC[C@H]3[C@@H]4CC(C[C@@]4(C)CC[C@@H]3[C@]2(CC1)C)=O Chemical compound C(C)(=O)OC1CC2=CC[C@H]3[C@@H]4CC(C[C@@]4(C)CC[C@@H]3[C@]2(CC1)C)=O BDLYNEBJXDHISO-DHSGYYQHSA-N 0.000 claims 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 1
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
150000002923 oximes Chemical class 0.000 claims 1
125000000913 palmityl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
229920002554 vinyl polymer Polymers 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 71
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical group O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 41
239000000203 mixture Substances 0.000 description 35
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
239000000243 solution Substances 0.000 description 33
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 30
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 20
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
239000000047 product Substances 0.000 description 16
238000010992 reflux Methods 0.000 description 16
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 15
235000019441 ethanol Nutrition 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
230000015572 biosynthetic process Effects 0.000 description 9
238000002844 melting Methods 0.000 description 9
230000008018 melting Effects 0.000 description 9
239000002244 precipitate Substances 0.000 description 9
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
229910052799 carbon Inorganic materials 0.000 description 8
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 8
238000001914 filtration Methods 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
238000001816 cooling Methods 0.000 description 7
239000005457 ice water Substances 0.000 description 7
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 6
239000013078 crystal Substances 0.000 description 6
238000004090 dissolution Methods 0.000 description 6
239000000262 estrogen Substances 0.000 description 6
239000011701 zinc Substances 0.000 description 6
229910052725 zinc Inorganic materials 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 5
238000007792 addition Methods 0.000 description 5
239000003098 androgen Substances 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 5
229960003399 estrone Drugs 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
239000003921 oil Substances 0.000 description 5
150000003431 steroids Chemical class 0.000 description 5
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
230000001548 androgenic effect Effects 0.000 description 4
239000003610 charcoal Substances 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
125000000468 ketone group Chemical group 0.000 description 4
239000007788 liquid Substances 0.000 description 4
238000007034 nitrosation reaction Methods 0.000 description 4
239000000126 substance Substances 0.000 description 4
239000002253 acid Substances 0.000 description 3
125000004429 atom Chemical group 0.000 description 3
238000009835 boiling Methods 0.000 description 3
230000001076 estrogenic effect Effects 0.000 description 3
230000009935 nitrosation Effects 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
239000002904 solvent Substances 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
FMGSKLZLMKYGDP-HQEMIIEJSA-N (8r,9s,10r,13s,14s)-3-hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one Chemical compound C1C(O)CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC=C21 FMGSKLZLMKYGDP-HQEMIIEJSA-N 0.000 description 2
VUQQUDLAAJRNMK-ZJPYXAASSA-N 3-Hydroxyestra-1,3,5(10)-trien-16-one Chemical compound C1CC2=CC(O)=CC=C2[C@@H]2[C@@H]1[C@@H]1CC(=O)C[C@@]1(C)CC2 VUQQUDLAAJRNMK-ZJPYXAASSA-N 0.000 description 2
XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 2
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 2
238000004061 bleaching Methods 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
238000004821 distillation Methods 0.000 description 2
230000008030 elimination Effects 0.000 description 2
238000003379 elimination reaction Methods 0.000 description 2
230000032050 esterification Effects 0.000 description 2
238000005886 esterification reaction Methods 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
239000011521 glass Substances 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
238000006317 isomerization reaction Methods 0.000 description 2
150000002576 ketones Chemical group 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
239000000155 melt Substances 0.000 description 2
238000002156 mixing Methods 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
238000000746 purification Methods 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
238000007127 saponification reaction Methods 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
238000005406 washing Methods 0.000 description 2
DNXHEGUUPJUMQT-UHFFFAOYSA-N (+)-estrone Natural products OC1=CC=C2C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 DNXHEGUUPJUMQT-UHFFFAOYSA-N 0.000 description 1
XFGUKBIUPHEOQN-MKKANBOJSA-N (8R,9S,10R,13S,14S)-16-hydroxyimino-3-methoxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-17-one Chemical compound N(O)=C1C([C@]2(C)[C@@H](C1)[C@@H]1CC=C3CC(CC[C@]3(C)[C@H]1CC2)OC)=O XFGUKBIUPHEOQN-MKKANBOJSA-N 0.000 description 1
FTVVRNPVTQSSQO-PZNIFIQVSA-N (8R,9S,10R,13S,14S)-17-hydroxy-3-methoxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,17-dodecahydrocyclopenta[a]phenanthren-16-one Chemical compound COC1CC[C@]2(C)[C@H]3CC[C@]4(C)C(O)C(=O)C[C@H]4[C@@H]3CC=C2C1 FTVVRNPVTQSSQO-PZNIFIQVSA-N 0.000 description 1
YWQFPAUGLVZHQW-SXXOCOEKSA-N (8S,9S,10R,13R,14S)-3-methoxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,17-dodecahydrocyclopenta[a]phenanthren-16-one Chemical compound COC1CC2=CC[C@H]3[C@@H]4CC(C[C@@]4(C)CC[C@@H]3[C@]2(CC1)C)=O YWQFPAUGLVZHQW-SXXOCOEKSA-N 0.000 description 1
VMYTXBKVYDESSJ-HQEMIIEJSA-N (8r,9s,10r,13s,14s)-3-hydroxy-10,13-dimethyl-1,2,3,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one Chemical compound OC1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 VMYTXBKVYDESSJ-HQEMIIEJSA-N 0.000 description 1
YJDYCULVYZDESB-HQEMIIEJSA-N (8r,9s,10s,13s,14s)-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-17-one Chemical compound C1CCC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC21 YJDYCULVYZDESB-HQEMIIEJSA-N 0.000 description 1
LKORCFVIUNVYRI-IKMRJCJTSA-N (9R,10S,13S)-13-methyl-1,2,3,4,5,6,9,10,11,12-decahydrocyclopenta[a]phenanthrene-3,16,17-triol Chemical compound C[C@@]12C(=C(C=C1C1=CCC3CC(CC[C@@H]3[C@H]1CC2)O)O)O LKORCFVIUNVYRI-IKMRJCJTSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
241000206761 Bacillariophyta Species 0.000 description 1
OXHIQOFZFIQRIE-JPBALBCUSA-N C[C@@]12CC(C[C@H]1[C@@H]1CC=C3CC(O)CC[C@]3(C)[C@H]1CC2)=NO Chemical compound C[C@@]12CC(C[C@H]1[C@@H]1CC=C3CC(O)CC[C@]3(C)[C@H]1CC2)=NO OXHIQOFZFIQRIE-JPBALBCUSA-N 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
101100408384 Danio rerio piwil2 gene Proteins 0.000 description 1
FMGSKLZLMKYGDP-UHFFFAOYSA-N Dehydroepiandrosterone Natural products C1C(O)CCC2(C)C3CCC(C)(C(CC4)=O)C4C3CC=C21 FMGSKLZLMKYGDP-UHFFFAOYSA-N 0.000 description 1
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
WKRLQDKEXYKHJB-UHFFFAOYSA-N Equilin Natural products OC1=CC=C2C3CCC(C)(C(CC4)=O)C4C3=CCC2=C1 WKRLQDKEXYKHJB-UHFFFAOYSA-N 0.000 description 1
DNXHEGUUPJUMQT-CBZIJGRNSA-N Estrone Chemical compound OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 DNXHEGUUPJUMQT-CBZIJGRNSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
229930194542 Keto Natural products 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
HKUKRSLIEVXDMS-APDHKMKFSA-N [(8r,9s,13s,14s)-13-methyl-17-oxo-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthren-3-yl] benzoate Chemical compound C([C@@H]1[C@@H](C2=CC=3)CC[C@]4([C@H]1CCC4=O)C)CC2=CC=3OC(=O)C1=CC=CC=C1 HKUKRSLIEVXDMS-APDHKMKFSA-N 0.000 description 1
229940030486 androgens Drugs 0.000 description 1
239000010425 asbestos Substances 0.000 description 1
229940077388 benzenesulfonate Drugs 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
FMGSKLZLMKYGDP-USOAJAOKSA-N dehydroepiandrosterone Chemical compound C1[C@@H](O)CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC=C21 FMGSKLZLMKYGDP-USOAJAOKSA-N 0.000 description 1
SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Natural products CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 1
150000002009 diols Chemical class 0.000 description 1
229940011871 estrogen Drugs 0.000 description 1
125000001033 ether group Chemical group 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
239000011491 glass wool Substances 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
OWFXIOWLTKNBAP-UHFFFAOYSA-N isoamyl nitrite Chemical compound CC(C)CCON=O OWFXIOWLTKNBAP-UHFFFAOYSA-N 0.000 description 1
239000000463 material Substances 0.000 description 1
239000000401 methanolic extract Substances 0.000 description 1
239000011707 mineral Substances 0.000 description 1
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IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
CUQOHAYJWVTKDE-UHFFFAOYSA-N potassium;butan-1-olate Chemical compound [K+].CCCC[O-] CUQOHAYJWVTKDE-UHFFFAOYSA-N 0.000 description 1
229960002847 prasterone Drugs 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
238000005057 refrigeration Methods 0.000 description 1
229910052895 riebeckite Inorganic materials 0.000 description 1
150000007659 semicarbazones Chemical class 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
230000009897 systematic effect Effects 0.000 description 1
239000003760 tallow Substances 0.000 description 1