BE421825A

BE421825A -

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Publication number: BE421825A
Authority: BE; Belgium
Prior art keywords: carbon; ketones; unsaturated; line; desc
Prior art date

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English (en)

French (fr)

Publication of BE421825A publication Critical patent/BE421825A/fr

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RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 92
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 58
229910052799 carbon Inorganic materials 0.000 claims description 48
150000001875 compounds Chemical class 0.000 claims description 46
LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 43
238000000034 method Methods 0.000 claims description 43
150000002576 ketones Chemical class 0.000 claims description 42
-1 organic acid salts Chemical class 0.000 claims description 41
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical class CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 40
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 33
125000002587 enol group Chemical group 0.000 claims description 30
239000003795 chemical substances by application Substances 0.000 claims description 26
230000000875 corresponding Effects 0.000 claims description 26
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 25
WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 25
150000003431 steroids Chemical class 0.000 claims description 25
125000000468 ketone group Chemical group 0.000 claims description 23
238000009835 boiling Methods 0.000 claims description 22
125000004432 carbon atoms Chemical group C* 0.000 claims description 22
LRHPLDYGYMQRHN-UHFFFAOYSA-N n-butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 22
150000002148 esters Chemical class 0.000 claims description 18
239000011541 reaction mixture Substances 0.000 claims description 18
229910052736 halogen Inorganic materials 0.000 claims description 17
150000002367 halogens Chemical class 0.000 claims description 17
238000000926 separation method Methods 0.000 claims description 15
239000011780 sodium chloride Substances 0.000 claims description 15
125000005843 halogen group Chemical group 0.000 claims description 14
238000004519 manufacturing process Methods 0.000 claims description 14
150000003839 salts Chemical class 0.000 claims description 14
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
239000007858 starting material Substances 0.000 claims description 13
OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 12
239000002253 acid Substances 0.000 claims description 11
125000004122 cyclic group Chemical group 0.000 claims description 11
150000002170 ethers Chemical class 0.000 claims description 11
QZLYKIGBANMMBK-UGCZWRCOSA-N 5α-Androstane Chemical compound C([C@@H]1CC2)CCC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CCC[C@@]2(C)CC1 QZLYKIGBANMMBK-UGCZWRCOSA-N 0.000 claims description 10
238000002425 crystallisation Methods 0.000 claims description 10
230000005712 crystallization Effects 0.000 claims description 10
238000002360 preparation method Methods 0.000 claims description 10
239000007795 chemical reaction product Substances 0.000 claims description 9
150000003128 pregnanes Chemical class 0.000 claims description 9
239000002904 solvent Substances 0.000 claims description 9
WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Chemical class OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 8
150000003432 sterols Chemical class 0.000 claims description 8
235000003702 sterols Nutrition 0.000 claims description 8
125000004429 atoms Chemical group 0.000 claims description 7
CPELXLSAUQHCOX-UHFFFAOYSA-M bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 7
125000001033 ether group Chemical group 0.000 claims description 7
239000004215 Carbon black (E152) Substances 0.000 claims description 6
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 claims description 6
238000006460 hydrolysis reaction Methods 0.000 claims description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
150000007513 acids Chemical class 0.000 claims description 5
238000005893 bromination reaction Methods 0.000 claims description 5
238000005695 dehalogenation reaction Methods 0.000 claims description 5
125000005594 diketone group Chemical group 0.000 claims description 5
229910000042 hydrogen bromide Inorganic materials 0.000 claims description 5
150000007530 organic bases Chemical class 0.000 claims description 5
GWYFCOCPABKNJV-UHFFFAOYSA-M 3-Methylbutanoic acid Chemical class CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 claims description 4
239000005711 Benzoic acid Chemical class 0.000 claims description 4
239000003513 alkali Substances 0.000 claims description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
150000001441 androstanes Chemical class 0.000 claims description 4
239000002585 base Substances 0.000 claims description 4
235000010233 benzoic acid Nutrition 0.000 claims description 4
125000004185 ester group Chemical group 0.000 claims description 4
238000005658 halogenation reaction Methods 0.000 claims description 4
150000007524 organic acids Chemical class 0.000 claims description 4
235000005985 organic acids Nutrition 0.000 claims description 4
GWYFCOCPABKNJV-UHFFFAOYSA-N 3-Methylbutanoic acid Chemical class CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims description 3
MOIPGXQKZSZOQX-UHFFFAOYSA-N Carbonyl bromide Chemical class BrC(Br)=O MOIPGXQKZSZOQX-UHFFFAOYSA-N 0.000 claims description 3
239000003153 chemical reaction reagent Substances 0.000 claims description 3
229910052757 nitrogen Inorganic materials 0.000 claims description 3
230000003647 oxidation Effects 0.000 claims description 3
238000007254 oxidation reaction Methods 0.000 claims description 3
210000004940 Nucleus Anatomy 0.000 claims description 2
150000001298 alcohols Chemical class 0.000 claims description 2
239000003054 catalyst Substances 0.000 claims description 2
238000009833 condensation Methods 0.000 claims description 2
230000005494 condensation Effects 0.000 claims description 2
238000006251 dihalogenation reaction Methods 0.000 claims description 2
230000002140 halogenating Effects 0.000 claims description 2
230000003301 hydrolyzing Effects 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
230000001264 neutralization Effects 0.000 claims description 2
229910052709 silver Inorganic materials 0.000 claims description 2
239000004332 silver Substances 0.000 claims description 2
150000002440 hydroxy compounds Chemical class 0.000 claims 2
125000004043 oxo group Chemical group O=* 0.000 claims 2
150000001443 androstenes Chemical class 0.000 claims 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims 1
229910052737 gold Inorganic materials 0.000 claims 1
239000010931 gold Substances 0.000 claims 1
125000000623 heterocyclic group Chemical group 0.000 claims 1
125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
XLSMFKSTNGKWQX-UHFFFAOYSA-N hydroxyacetone Chemical class CC(=O)CO XLSMFKSTNGKWQX-UHFFFAOYSA-N 0.000 claims 1
125000003696 stearoyl group Polymers O=C([*])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])C([H])([H])C([H])([H])[H] 0.000 claims 1
150000003751 zinc Chemical class 0.000 claims 1
238000006243 chemical reaction Methods 0.000 description 39
HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 34
229960000583 Acetic Acid Drugs 0.000 description 25
239000000047 product Substances 0.000 description 25
SCVFZCLFOSHCOH-UHFFFAOYSA-M Potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 24
239000000203 mixture Substances 0.000 description 24
239000012362 glacial acetic acid Substances 0.000 description 21
CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 19
238000001914 filtration Methods 0.000 description 16
UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
238000002844 melting Methods 0.000 description 14
KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 14
238000001953 recrystallisation Methods 0.000 description 13
235000011056 potassium acetate Nutrition 0.000 description 12
238000007792 addition Methods 0.000 description 11
238000010992 reflux Methods 0.000 description 11
238000001816 cooling Methods 0.000 description 10
YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 10
229940050390 Benzoate Drugs 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 9
PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
238000000354 decomposition reaction Methods 0.000 description 8
238000001704 evaporation Methods 0.000 description 8
CPELXLSAUQHCOX-UHFFFAOYSA-N hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 8
229940072033 potash Drugs 0.000 description 8
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
235000015320 potassium carbonate Nutrition 0.000 description 8
239000002994 raw material Substances 0.000 description 8
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
WPYMKLBDIGXBTP-UHFFFAOYSA-M benzoate Chemical compound [O-]C(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-M 0.000 description 7
238000010438 heat treatment Methods 0.000 description 7
239000000543 intermediate Substances 0.000 description 7
238000005406 washing Methods 0.000 description 7
239000012452 mother liquor Substances 0.000 description 6
230000001476 alcoholic Effects 0.000 description 5
239000000155 melt Substances 0.000 description 5
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 5
239000003960 organic solvent Substances 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
150000003222 pyridines Chemical class 0.000 description 5
238000007127 saponification reaction Methods 0.000 description 5
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
238000003756 stirring Methods 0.000 description 5
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 4
229940103091 Potassium Benzoate Drugs 0.000 description 4
XAEFZNCEHLXOMS-UHFFFAOYSA-M Potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 4
IOLCXVTUBQKXJR-UHFFFAOYSA-M Potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 4
150000001558 benzoic acid derivatives Chemical class 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
238000005755 formation reaction Methods 0.000 description 4
239000007788 liquid Substances 0.000 description 4
239000004300 potassium benzoate Substances 0.000 description 4
235000010235 potassium benzoate Nutrition 0.000 description 4
235000017550 sodium carbonate Nutrition 0.000 description 4
229910000029 sodium carbonate Inorganic materials 0.000 description 4
HFMWFEJAJZUPGE-SRTNJPEQSA-N (8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,5,6,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,4-dione Chemical compound C1CC2C(=O)C(=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 HFMWFEJAJZUPGE-SRTNJPEQSA-N 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 3
AEMFNILZOJDQLW-QAGGRKNESA-N Androstenedione Chemical compound 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
YEQGMMKSJLDZJR-AANOPSFLSA-N BrC1[C@H]2[C@@H]3C(C([C@@H]([C@]3(CC[C@@H]2[C@]2(CCCCC2C1)C)C)[C@H](C)CCCC(C)C)=O)(Br)Br Chemical compound BrC1[C@H]2[C@@H]3C(C([C@@H]([C@]3(CC[C@@H]2[C@]2(CCCCC2C1)C)C)[C@H](C)CCCC(C)C)=O)(Br)Br YEQGMMKSJLDZJR-AANOPSFLSA-N 0.000 description 3
229940093915 Gynecological Organic acids Drugs 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
150000008065 acid anhydrides Chemical class 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
239000007859 condensation product Substances 0.000 description 3
239000000463 material Substances 0.000 description 3
239000003208 petroleum Substances 0.000 description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
229910052700 potassium Inorganic materials 0.000 description 3
239000011591 potassium Substances 0.000 description 3
239000001187 sodium carbonate Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
JWMFYGXQPXQEEM-NUNROCCHSA-N 5β-pregnane Chemical compound C([C@H]1CC2)CCC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](CC)[C@@]2(C)CC1 JWMFYGXQPXQEEM-NUNROCCHSA-N 0.000 description 2
IVATWMMBMMIHMV-OMYOZJEQSA-N BrC1(C(C([C@@H]2[C@]1(C)CC[C@H]1[C@H]2CC[C@H]2CCCC[C@]12C)=O)=O)Br Chemical compound BrC1(C(C([C@@H]2[C@]1(C)CC[C@H]1[C@H]2CC[C@H]2CCCC[C@]12C)=O)=O)Br IVATWMMBMMIHMV-OMYOZJEQSA-N 0.000 description 2
210000001736 Capillaries Anatomy 0.000 description 2
229940107161 Cholesterol Drugs 0.000 description 2
DUIOPKIIICUYRZ-UHFFFAOYSA-N Semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 2
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 description 2
WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
239000003610 charcoal Substances 0.000 description 2
235000012000 cholesterol Nutrition 0.000 description 2
238000004821 distillation Methods 0.000 description 2
238000000605 extraction Methods 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
235000011118 potassium hydroxide Nutrition 0.000 description 2
VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
239000001632 sodium acetate Substances 0.000 description 2
235000017281 sodium acetate Nutrition 0.000 description 2
235000011121 sodium hydroxide Nutrition 0.000 description 2
WGLPBDUCMAPZCE-UHFFFAOYSA-N trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 2
VMNRNUNYBVFVQI-QYXZOKGRSA-N (5S,8S,9S,10S,13S,14S)-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one Chemical compound C([C@@H]1CC2)C(=O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CCC[C@@]2(C)CC1 VMNRNUNYBVFVQI-QYXZOKGRSA-N 0.000 description 1
LNGLEOIUQBVRRY-JYQHCDCXSA-N (8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,4,5,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,6-dione Chemical compound C1C(=O)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 LNGLEOIUQBVRRY-JYQHCDCXSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
229940076134 Benzene Drugs 0.000 description 1
KKJWFSABJAEQDW-RJNQIKOBSA-N BrC1(C([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)Br Chemical compound BrC1(C([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)Br KKJWFSABJAEQDW-RJNQIKOBSA-N 0.000 description 1
VPJQKYVRISQHDC-KOKUEQTASA-N BrC1C(C(C2CC[C@H]3[C@@H]4CCC([C@@]4(C)CC[C@@H]3[C@]2(C1)C)=O)Br)=O Chemical compound BrC1C(C(C2CC[C@H]3[C@@H]4CCC([C@@]4(C)CC[C@@H]3[C@]2(C1)C)=O)Br)=O VPJQKYVRISQHDC-KOKUEQTASA-N 0.000 description 1
HJFFLJUEFIYEPI-JYSOYWRPSA-N BrC1CC(C2CC[C@H]3[C@@H]4CC([C@@H]([C@]4(CC[C@@H]3[C@]2(C1)C)C)[C@H](C)CCCC(C)C)=O)Br Chemical compound BrC1CC(C2CC[C@H]3[C@@H]4CC([C@@H]([C@]4(CC[C@@H]3[C@]2(C1)C)C)[C@H](C)CCCC(C)C)=O)Br HJFFLJUEFIYEPI-JYSOYWRPSA-N 0.000 description 1
229960005069 Calcium Drugs 0.000 description 1
229960003563 Calcium Carbonate Drugs 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate dianion Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
229960001701 Chloroform Drugs 0.000 description 1
KRVSOGSZCMJSLX-UHFFFAOYSA-L Chromic acid Chemical compound O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
ROXSVUDAPGCQQS-NXPPOZPUSA-N ClC1(C([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)Br Chemical compound ClC1(C([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)Br ROXSVUDAPGCQQS-NXPPOZPUSA-N 0.000 description 1
DNEBQEUNDBOLHD-OZWOBKTPSA-N ClC1C([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 ClC1C([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 DNEBQEUNDBOLHD-OZWOBKTPSA-N 0.000 description 1
JLTDJTHDQAWBAV-UHFFFAOYSA-N Dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
DMBHHRLKUKUOEG-UHFFFAOYSA-N Diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 1
229940035422 Diphenylamine Drugs 0.000 description 1
QZRGKCOWNLSUDK-UHFFFAOYSA-N Iodochlorine Chemical compound ICl QZRGKCOWNLSUDK-UHFFFAOYSA-N 0.000 description 1
RBTARNINKXHZNM-UHFFFAOYSA-K Iron(III) chloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
241000229754 Iva xanthiifolia Species 0.000 description 1
XAMUDJHXFNRLCY-UHFFFAOYSA-N Phenthoate Chemical compound CCOC(=O)C(SP(=S)(OC)OC)C1=CC=CC=C1 XAMUDJHXFNRLCY-UHFFFAOYSA-N 0.000 description 1
RJKFOVLPORLFTN-STHVQZNPSA-N Progesterone Natural products O=C(C)[C@@H]1[C@@]2(C)[C@H]([C@H]3[C@@H]([C@]4(C)C(=CC(=O)CC4)CC3)CC2)CC1 RJKFOVLPORLFTN-STHVQZNPSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
RJKFOVLPORLFTN-LEKSSAKUSA-N Syngestrets Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 description 1
229960003604 Testosterone Drugs 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
150000003855 acyl compounds Chemical class 0.000 description 1
238000004220 aggregation Methods 0.000 description 1
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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