CH608245A5 - Process for obtaining and isolating solasodine - Google Patents

Process for obtaining and isolating solasodine

Info

Publication number: CH608245A5
Authority: CH; Switzerland
Prior art keywords: weight; mixture; fruits; parts; glycosides
Prior art date: 1973-02-09

Application number

CH523874A

Other languages

German (de)

English (en)

Inventor

Milton Guerrero

Original Assignee

Escuela Politecnica Nacional

Priority date (The priority date 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 date listed.)

1973-02-09

Filing date

1974-04-16

Publication date

1978-12-29

1974-02-08 Priority to AU65385/74A priority Critical patent/AU482516B2/en

1974-02-11 Priority to GB613774A priority patent/GB1465392A/en

1974-04-02 Priority to CA196,612A priority patent/CA1029010A/fr

1974-04-10 Priority to NL7404924A priority patent/NL7404924A/xx

1974-04-16 Application filed by Escuela Politecnica Nacional filed Critical Escuela Politecnica Nacional

1974-04-16 Priority to CH523874A priority patent/CH608245A5/de

1974-04-17 Priority to JP49043219A priority patent/JPS50135209A/ja

1974-04-23 Priority to DD178080A priority patent/DD113753A5/xx

1974-04-25 Priority to BE143603A priority patent/BE814177A/fr

1974-05-21 Priority to BR4139/74A priority patent/BR7404139A/pt

1974-06-04 Priority to US05/476,278 priority patent/US3960839A/en

1974-07-12 Priority to FR7424352A priority patent/FR2277820A1/fr

1978-12-29 Publication of CH608245A5 publication Critical patent/CH608245A5/de

Links

JXWLYDNHVXFBJA-UHFFFAOYSA-N solasodine Natural products CC1CCC2(NC1)NC3CC4C5CC=C6CC(O)CCC6(C)C5CCC4(C)C3C2C JXWLYDNHVXFBJA-UHFFFAOYSA-N 0.000 title claims abstract description 65
KWVISVAMQJWJSZ-VKROHFNGSA-N solasodine 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)CN1 KWVISVAMQJWJSZ-VKROHFNGSA-N 0.000 title claims abstract description 62
238000000034 method Methods 0.000 title claims description 67
229930182470 glycoside Natural products 0.000 claims abstract description 129
150000002338 glycosides Chemical class 0.000 claims abstract description 125
235000013399 edible fruits Nutrition 0.000 claims abstract description 102
239000000203 mixture Substances 0.000 claims abstract description 93
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims abstract description 90
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 55
239000012535 impurity Substances 0.000 claims abstract description 50
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 42
241000196324 Embryophyta Species 0.000 claims abstract description 37
241000207763 Solanum Species 0.000 claims abstract description 22
235000002634 Solanum Nutrition 0.000 claims abstract description 21
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 15
150000001298 alcohols Chemical class 0.000 claims abstract description 9
150000003431 steroids Chemical class 0.000 claims abstract description 9
239000003814 drug Substances 0.000 claims abstract description 6
229940079593 drug Drugs 0.000 claims abstract description 6
FUFLCEKSBBHCMO-UHFFFAOYSA-N 11-dehydrocorticosterone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 FUFLCEKSBBHCMO-UHFFFAOYSA-N 0.000 claims abstract description 3
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 claims abstract description 3
MFYSYFVPBJMHGN-UHFFFAOYSA-N Cortisone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)(O)C(=O)CO)C4C3CCC2=C1 MFYSYFVPBJMHGN-UHFFFAOYSA-N 0.000 claims abstract description 3
229960004544 cortisone Drugs 0.000 claims abstract description 3
239000003163 gonadal steroid hormone Substances 0.000 claims abstract description 3
238000006460 hydrolysis reaction Methods 0.000 claims description 76
230000007062 hydrolysis Effects 0.000 claims description 75
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 63
238000000605 extraction Methods 0.000 claims description 31
239000006286 aqueous extract Substances 0.000 claims description 30
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 29
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 27
239000003513 alkali Substances 0.000 claims description 19
239000000463 material Substances 0.000 claims description 19
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 18
238000004519 manufacturing process Methods 0.000 claims description 14
238000004821 distillation Methods 0.000 claims description 13
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 13
229910000041 hydrogen chloride Inorganic materials 0.000 claims description 13
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 12
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 12
WQLVFSAGQJTQCK-UHFFFAOYSA-N diosgenin Natural products CC1C(C2(CCC3C4(C)CCC(O)CC4=CCC3C2C2)C)C2OC11CCC(C)CO1 WQLVFSAGQJTQCK-UHFFFAOYSA-N 0.000 claims description 10
238000002955 isolation Methods 0.000 claims description 9
DWCSNWXARWMZTG-UHFFFAOYSA-N Trigonegenin A Natural products CC1C(C2(CCC3C4(C)CCC(O)C=C4CCC3C2C2)C)C2OC11CCC(C)CO1 DWCSNWXARWMZTG-UHFFFAOYSA-N 0.000 claims description 8
239000012675 alcoholic extract Substances 0.000 claims description 8
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 claims description 8
230000005070 ripening Effects 0.000 claims description 8
241000894007 species Species 0.000 claims description 8
INLFWQCRAJUDCR-IQVMEADQSA-N (1R,2S,4S,5'S,6R,7S,8R,9S,12S,13S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane] Chemical compound O([C@@H]1[C@@H]([C@]2(CC[C@@H]3[C@@]4(C)CCCCC4CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@H](C)CO1 INLFWQCRAJUDCR-IQVMEADQSA-N 0.000 claims description 6
241000234272 Dioscoreaceae Species 0.000 claims description 6
229910000027 potassium carbonate Inorganic materials 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 6
229910000029 sodium carbonate Inorganic materials 0.000 claims description 6
239000002243 precursor Substances 0.000 claims description 5
238000005406 washing Methods 0.000 claims description 5
235000007056 Dioscorea composita Nutrition 0.000 claims description 4
241000156497 Dioscorea composita Species 0.000 claims description 4
241000234280 Liliaceae Species 0.000 claims description 4
238000005903 acid hydrolysis reaction Methods 0.000 claims description 4
238000010438 heat treatment Methods 0.000 claims description 4
-1 solasodine glycosides Chemical class 0.000 claims description 4
239000004615 ingredient Substances 0.000 claims description 3
239000002994 raw material Substances 0.000 claims description 3
235000008499 Canella winterana Nutrition 0.000 claims description 2
235000004868 Dioscorea macrostachya Nutrition 0.000 claims description 2
235000010240 Paullinia pinnata Nutrition 0.000 claims description 2
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 2
238000009395 breeding Methods 0.000 claims description 2
230000001488 breeding effect Effects 0.000 claims description 2
238000003306 harvesting Methods 0.000 claims description 2
239000003960 organic solvent Substances 0.000 claims description 2
238000011084 recovery Methods 0.000 claims description 2
JUVIOZPCNVVQFO-HBGVWJBISA-N rotenone Chemical compound O([C@H](CC1=C2O3)C(C)=C)C1=CC=C2C(=O)[C@@H]1[C@H]3COC2=C1C=C(OC)C(OC)=C2 JUVIOZPCNVVQFO-HBGVWJBISA-N 0.000 claims description 2
NWMIYTWHUDFRPL-UHFFFAOYSA-N sapogenin Natural products COC(=O)C1(CO)C(O)CCC2(C)C1CCC3(C)C2CC=C4C5C(C)(O)C(C)CCC5(CCC34C)C(=O)O NWMIYTWHUDFRPL-UHFFFAOYSA-N 0.000 claims description 2
229930182490 saponin Natural products 0.000 claims description 2
150000007949 saponins Chemical class 0.000 claims description 2
235000017709 saponins Nutrition 0.000 claims description 2
238000001179 sorption measurement Methods 0.000 claims description 2
241001283970 Dioscorea mexicana Species 0.000 claims 1
239000000284 extract Substances 0.000 abstract description 6
239000002253 acid Substances 0.000 abstract description 2
239000000413 hydrolysate Substances 0.000 abstract 1
239000002244 precipitate Substances 0.000 description 52
239000000047 product Substances 0.000 description 23
239000007788 liquid Substances 0.000 description 12
238000002474 experimental method Methods 0.000 description 9
239000000706 filtrate Substances 0.000 description 9
238000001914 filtration Methods 0.000 description 8
TWCMVXMQHSVIOJ-UHFFFAOYSA-N Aglycone of yadanzioside D Natural products COC(=O)C12OCC34C(CC5C(=CC(O)C(O)C5(C)C3C(O)C1O)C)OC(=O)C(OC(=O)C)C24 TWCMVXMQHSVIOJ-UHFFFAOYSA-N 0.000 description 7
PLMKQQMDOMTZGG-UHFFFAOYSA-N Astrantiagenin E-methylester Natural products CC12CCC(O)C(C)(CO)C1CCC1(C)C2CC=C2C3CC(C)(C)CCC3(C(=O)OC)CCC21C PLMKQQMDOMTZGG-UHFFFAOYSA-N 0.000 description 7
PFOARMALXZGCHY-UHFFFAOYSA-N homoegonol Natural products C1=C(OC)C(OC)=CC=C1C1=CC2=CC(CCCO)=CC(OC)=C2O1 PFOARMALXZGCHY-UHFFFAOYSA-N 0.000 description 7
OYNIUJOJEWHJPN-UHFFFAOYSA-N Solasodiene Chemical compound CC1C(C2(CCC3C4(C)CCC=CC4=CCC3C2C2)C)C2OC11CCC(C)CN1 OYNIUJOJEWHJPN-UHFFFAOYSA-N 0.000 description 6
238000001556 precipitation Methods 0.000 description 6
238000010992 reflux Methods 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
238000001035 drying Methods 0.000 description 5
239000012467 final product Substances 0.000 description 5
210000004209 hair Anatomy 0.000 description 5
239000011344 liquid material Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
239000007858 starting material Substances 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 4
239000012065 filter cake Substances 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
238000000926 separation method Methods 0.000 description 4
239000007787 solid Substances 0.000 description 4
DKVBOUDTNWVDEP-NJCHZNEYSA-N teicoplanin aglycone Chemical compound N([C@H](C(N[C@@H](C1=CC(O)=CC(O)=C1C=1C(O)=CC=C2C=1)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)OC=1C=C3C=C(C=1O)OC1=CC=C(C=C1Cl)C[C@H](C(=O)N1)NC([C@H](N)C=4C=C(O5)C(O)=CC=4)=O)C(=O)[C@@H]2NC(=O)[C@@H]3NC(=O)[C@@H]1C1=CC5=CC(O)=C1 DKVBOUDTNWVDEP-NJCHZNEYSA-N 0.000 description 4
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
239000002585 base Substances 0.000 description 3
238000009835 boiling Methods 0.000 description 3
238000005119 centrifugation Methods 0.000 description 3
238000001816 cooling Methods 0.000 description 3
230000000875 corresponding effect Effects 0.000 description 3
239000000155 melt Substances 0.000 description 3
235000000346 sugar Nutrition 0.000 description 3
235000013311 vegetables Nutrition 0.000 description 3
230000004580 weight loss Effects 0.000 description 3
101100347605 Arabidopsis thaliana VIII-A gene Proteins 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
241000208292 Solanaceae Species 0.000 description 2
PQUOYNVEQWXFHJ-UHFFFAOYSA-N Solanidin Natural products CC1CCC2C(C)C3(C)C4CCC5C(CC=C6CC(O)CCC56C)C4CC3N2C1 PQUOYNVEQWXFHJ-UHFFFAOYSA-N 0.000 description 2
LFYFMIISECOQEE-UHFFFAOYSA-N Solasodin Natural products N1CC(C)CCC11OC(CC2C3(CCC4C5(C)CCC(O)CC5=CCC42)C)C3C1 LFYFMIISECOQEE-UHFFFAOYSA-N 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
230000007423 decrease Effects 0.000 description 2
230000018044 dehydration Effects 0.000 description 2
238000006297 dehydration reaction Methods 0.000 description 2
150000001993 dienes Chemical class 0.000 description 2
230000005484 gravity Effects 0.000 description 2
230000021962 pH elevation Effects 0.000 description 2
239000011877 solvent mixture Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
239000008399 tap water Substances 0.000 description 2
235000020679 tap water Nutrition 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
241001164374 Calyx Species 0.000 description 1
244000169962 Dioscorea macrostachya Species 0.000 description 1
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
241001460678 Napo <wasp> Species 0.000 description 1
MBWUSSKCCUMJHO-ZGXDEBHDSA-N Solamargine Chemical compound O([C@@H]1[C@@H](CO)O[C@H]([C@@H]([C@H]1O)O[C@H]1[C@@H]([C@H](O)[C@@H](O)[C@H](C)O1)O)O[C@@H]1CC2=CC[C@H]3[C@@H]4C[C@H]5[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@@H]([C@]1(NC[C@H](C)CC1)O5)C)[C@@H]1O[C@@H](C)[C@H](O)[C@@H](O)[C@H]1O MBWUSSKCCUMJHO-ZGXDEBHDSA-N 0.000 description 1
MBWUSSKCCUMJHO-DVDUUUGDSA-N Solamargine Natural products O([C@@H]1[C@@H](O)[C@@H](O[C@H]2[C@H](O)[C@H](O)[C@@H](O)[C@H](C)O2)[C@H](CO)O[C@@H]1O[C@@H]1CC=2[C@@](C)([C@@H]3[C@H]([C@H]4[C@@](C)([C@H]5[C@@H](C)[C@@]6(O[C@H]5C4)NC[C@H](C)CC6)CC3)CC=2)CC1)[C@H]1[C@H](O)[C@H](O)[C@@H](O)[C@@H](C)O1 MBWUSSKCCUMJHO-DVDUUUGDSA-N 0.000 description 1
241000047051 Solanum marginatum Species 0.000 description 1
KNLOWJPFLKGYGQ-UHFFFAOYSA-N Solasodine 3-O-??-L-rhamnopyranosyl (1‘Â∆2)-O-[??-D-glucopyranosyl (1‘Â∆4)]-??-D-glucopyranoside Natural products O1C2(NCC(C)CC2)C(C)C(C2(CCC3C4(C)CC5)C)C1CC2C3CC=C4CC5OC(C(C1O)OC2C(C(O)C(O)C(C)O2)O)OC(CO)C1OC1OC(CO)C(O)C(O)C1O KNLOWJPFLKGYGQ-UHFFFAOYSA-N 0.000 description 1
QCTMYNGDIBTNSK-UHFFFAOYSA-N Solasonin Natural products O1C2(NCC(C)CC2)C(C)C(C2(CCC3C4(C)CC5)C)C1CC2C3CC=C4CC5OC(C1OC2C(C(O)C(O)C(C)O2)O)OC(CO)C(O)C1OC1OC(CO)C(O)C(O)C1O QCTMYNGDIBTNSK-UHFFFAOYSA-N 0.000 description 1
QCTMYNGDIBTNSK-QCNFCIKQSA-N Solasonine Natural products O([C@@H]1[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@@H](O)[C@H](C)O2)[C@@H](O[C@@H]2CC=3[C@@](C)([C@@H]4[C@H]([C@H]5[C@@](C)([C@H]6[C@@H](C)[C@@]7(O[C@H]6C5)NC[C@H](C)CC7)CC4)CC=3)CC2)O[C@@H](CO)[C@@H]1O)[C@H]1[C@@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 QCTMYNGDIBTNSK-QCNFCIKQSA-N 0.000 description 1
241001428384 Zamora Species 0.000 description 1
230000002411 adverse Effects 0.000 description 1
230000032683 aging Effects 0.000 description 1
RCTKRNCKOYYRIO-UHFFFAOYSA-N alpha-Solamarine Natural products O1C2(NCC(C)CC2)C(C)C(C2(CCC3C4(C)CC5)C)C1CC2C3CC=C4CC5OC(C1O)OC(CO)C(O)C1OC1OC(CO)C(O)C(O)C1OC1OC(C)C(O)C(O)C1O RCTKRNCKOYYRIO-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
BLRFKPWRSOZROE-UHFFFAOYSA-N beta-Solamargin Natural products CC1CCC2(NC1)OC3CC4C5CC=C6CC(CCC6(C)C5CCC4(C)C3C2C)OC7OC(COC8OC(C)C(OC9OC(C)C(O)C(O)C9O)C(O)C8O)C(O)C(O)C7O BLRFKPWRSOZROE-UHFFFAOYSA-N 0.000 description 1
238000004364 calculation method Methods 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
230000004456 color vision Effects 0.000 description 1
239000000470 constituent Substances 0.000 description 1
238000011109 contamination Methods 0.000 description 1
238000010908 decantation Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
235000011869 dried fruits Nutrition 0.000 description 1
239000008098 formaldehyde solution Substances 0.000 description 1
238000000227 grinding Methods 0.000 description 1
239000005556 hormone Substances 0.000 description 1
229940088597 hormone Drugs 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
230000035800 maturation Effects 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
239000012071 phase Substances 0.000 description 1
239000011148 porous material Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000003825 pressing Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
230000000630 rising effect Effects 0.000 description 1
239000013049 sediment Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
BIMWFUACEQGSPS-UHFFFAOYSA-N solamargin Natural products CC1CCC2(NC1)OC3CC4C5CC=C6CC(CCC6(C)C5CCC4(C)C3C2C)OC7OC(COC8OC(C)C(O)C(O)C8O)C(O)C(O)C7OC9OC(C)C(O)C(O)C9O BIMWFUACEQGSPS-UHFFFAOYSA-N 0.000 description 1
238000003756 stirring Methods 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
UMFCIIBZHQXRCJ-NSCUHMNNSA-N trans-anol Chemical compound C\C=C\C1=CC=C(O)C=C1 UMFCIIBZHQXRCJ-NSCUHMNNSA-N 0.000 description 1
239000005418 vegetable material Substances 0.000 description 1
QCTMYNGDIBTNSK-XEAAVONHSA-N α-Solamarine Chemical compound O([C@H]1[C@@H](O)[C@@H](CO)O[C@H]([C@@H]1O[C@H]1[C@@H]([C@H](O)[C@@H](O)[C@H](C)O1)O)O[C@@H]1CC2=CC[C@H]3[C@@H]4C[C@H]5[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@@H]([C@]1(NC[C@H](C)CC1)O5)C)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O QCTMYNGDIBTNSK-XEAAVONHSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- C07J71/0005—Oxygen-containing hetero ring
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/81—Solanaceae (Potato family), e.g. tobacco, nightshade, tomato, belladonna, capsicum or jimsonweed

Landscapes

Health & Medical Sciences (AREA)
Natural Medicines & Medicinal Plants (AREA)
Chemical & Material Sciences (AREA)
General Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Medical Informatics (AREA)
Mycology (AREA)
Biotechnology (AREA)
Botany (AREA)
Engineering & Computer Science (AREA)
Medicinal Chemistry (AREA)
Microbiology (AREA)
Alternative & Traditional Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Saccharide Compounds (AREA)
Medicines Containing Plant Substances (AREA)

CH523874A 1973-02-09 1974-04-16 Process for obtaining and isolating solasodine CH608245A5 (en)

Priority Applications (11)

Application Number	Priority Date	Filing Date	Title
AU65385/74A AU482516B2 (en)	1973-02-09	1974-02-08	Process for recovering and isolating solasodine
GB613774A GB1465392A (en)	1973-02-09	1974-02-11	Process for obtaining solasodine and glycosides thereof
CA196,612A CA1029010A (fr)	1973-02-09	1974-04-02	Procede pour la recuperation et l'isolement de la solasodine
NL7404924A NL7404924A (nl)	1973-02-09	1974-04-10	Werkwijze voor het winnen en afscheiden van solasodine.
CH523874A CH608245A5 (en)	1973-02-09	1974-04-16	Process for obtaining and isolating solasodine
JP49043219A JPS50135209A (fr)	1973-02-09	1974-04-17
DD178080A DD113753A5 (fr)	1973-02-09	1974-04-23
BE143603A BE814177A (fr)	1973-02-09	1974-04-25	Procede d'extraction et de separation de la solasodine
BR4139/74A BR7404139A (pt)	1973-02-09	1974-05-21	Processo para recuperar e isolar solasodina
US05/476,278 US3960839A (en)	1973-02-09	1974-06-04	Process for recovering and isolating solasodine and glycosides thereof
FR7424352A FR2277820A1 (fr)	1973-02-09	1974-07-12	Procede d'extraction et de separation de la solasodine

Applications Claiming Priority (8)

Application Number	Priority Date	Filing Date	Title
US33100473A	1973-02-09	1973-02-09
CA196,612A CA1029010A (fr)	1973-02-09	1974-04-02	Procede pour la recuperation et l'isolement de la solasodine
NL7404924A NL7404924A (nl)	1973-02-09	1974-04-10	Werkwijze voor het winnen en afscheiden van solasodine.
CH523874A CH608245A5 (en)	1973-02-09	1974-04-16	Process for obtaining and isolating solasodine
JP49043219A JPS50135209A (fr)	1973-02-09	1974-04-17
DD178080A DD113753A5 (fr)	1973-02-09	1974-04-23
BR4139/74A BR7404139A (pt)	1973-02-09	1974-05-21	Processo para recuperar e isolar solasodina
FR7424352A FR2277820A1 (fr)	1973-02-09	1974-07-12	Procede d'extraction et de separation de la solasodine

Publications (1)

Publication Number	Publication Date
CH608245A5 true CH608245A5 (en)	1978-12-29

Family

ID=27570189

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH523874A CH608245A5 (en)	1973-02-09	1974-04-16	Process for obtaining and isolating solasodine

Country Status (9)

Country	Link
JP (1)	JPS50135209A (fr)
BE (1)	BE814177A (fr)
BR (1)	BR7404139A (fr)
CA (1)	CA1029010A (fr)
CH (1)	CH608245A5 (fr)
DD (1)	DD113753A5 (fr)
FR (1)	FR2277820A1 (fr)
GB (1)	GB1465392A (fr)
NL (1)	NL7404924A (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5259997A (en) *	1975-11-12	1977-05-17	Nippon Keibi Hosho Kk	Chemical fire extinguishing method
JPS5259996A (en) *	1975-11-12	1977-05-17	Nippon Keibi Hosho Kk	Chemical fire extinguishing method

1974
- 1974-02-11 GB GB613774A patent/GB1465392A/en not_active Expired
- 1974-04-02 CA CA196,612A patent/CA1029010A/fr not_active Expired
- 1974-04-10 NL NL7404924A patent/NL7404924A/xx not_active Application Discontinuation
- 1974-04-16 CH CH523874A patent/CH608245A5/de not_active IP Right Cessation
- 1974-04-17 JP JP49043219A patent/JPS50135209A/ja active Pending
- 1974-04-23 DD DD178080A patent/DD113753A5/xx unknown
- 1974-04-25 BE BE143603A patent/BE814177A/fr unknown
- 1974-05-21 BR BR4139/74A patent/BR7404139A/pt unknown
- 1974-07-12 FR FR7424352A patent/FR2277820A1/fr active Granted

Also Published As

Publication number	Publication date
DD113753A5 (fr)	1975-06-20
NL7404924A (nl)	1975-10-14
AU6538574A (en)	1975-08-14
FR2277820A1 (fr)	1976-02-06
GB1465392A (en)	1977-02-23
BE814177A (fr)	1974-10-25
CA1029010A (fr)	1978-04-04
JPS50135209A (fr)	1975-10-27
BR7404139A (pt)	1976-02-03
FR2277820B3 (fr)	1977-05-06

Legal Events

Date	Code	Title	Description
1980-12-31	PL	Patent ceased
2024-10-31	PL	Patent ceased

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