ES465156A1 - Procedure for preparing glycosides with an unsaturated aglicon. (Machine-translation by Google Translate, not legally binding) - Google Patents
Procedure for preparing glycosides with an unsaturated aglicon. (Machine-translation by Google Translate, not legally binding)Info
- Publication number
- ES465156A1 ES465156A1 ES465156A ES465156A ES465156A1 ES 465156 A1 ES465156 A1 ES 465156A1 ES 465156 A ES465156 A ES 465156A ES 465156 A ES465156 A ES 465156A ES 465156 A1 ES465156 A1 ES 465156A1
- Authority
- ES
- Spain
- Prior art keywords
- glycosides
- aglicon
- unsaturated
- translation
- procedure
- 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.)
- Expired
Links
- 229930182470 glycoside Natural products 0.000 title abstract 5
- 150000002338 glycosides Chemical class 0.000 title abstract 3
- 238000000034 method Methods 0.000 title 1
- GZSOSUNBTXMUFQ-YFAPSIMESA-N diosmin Chemical compound C1=C(O)C(OC)=CC=C1C(OC1=C2)=CC(=O)C1=C(O)C=C2O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO[C@H]2[C@@H]([C@H](O)[C@@H](O)[C@H](C)O2)O)O1 GZSOSUNBTXMUFQ-YFAPSIMESA-N 0.000 abstract 3
- VUYDGVRIQRPHFX-UHFFFAOYSA-N hesperidin Natural products COc1cc(ccc1O)C2CC(=O)c3c(O)cc(OC4OC(COC5OC(O)C(O)C(O)C5O)C(O)C(O)C4O)cc3O2 VUYDGVRIQRPHFX-UHFFFAOYSA-N 0.000 abstract 3
- ARGKVCXINMKCAZ-UHFFFAOYSA-N neohesperidine Natural products C1=C(O)C(OC)=CC=C1C1OC2=CC(OC3C(C(O)C(O)C(CO)O3)OC3C(C(O)C(O)C(C)O3)O)=CC(O)=C2C(=O)C1 ARGKVCXINMKCAZ-UHFFFAOYSA-N 0.000 abstract 3
- GZSOSUNBTXMUFQ-NJGQXECBSA-N 5,7,3'-Trihydroxy-4'-methoxyflavone 7-O-rutinoside Natural products O(C[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@H](Oc2cc(O)c3C(=O)C=C(c4cc(O)c(OC)cc4)Oc3c2)O1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@H](C)O1 GZSOSUNBTXMUFQ-NJGQXECBSA-N 0.000 abstract 2
- ZONYXWQDUYMKFB-UHFFFAOYSA-N SJ000286395 Natural products O1C2=CC=CC=C2C(=O)CC1C1=CC=CC=C1 ZONYXWQDUYMKFB-UHFFFAOYSA-N 0.000 abstract 2
- GAMYVSCDDLXAQW-AOIWZFSPSA-N Thermopsosid Natural products O(C)c1c(O)ccc(C=2Oc3c(c(O)cc(O[C@H]4[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O4)c3)C(=O)C=2)c1 GAMYVSCDDLXAQW-AOIWZFSPSA-N 0.000 abstract 2
- 229960004352 diosmin Drugs 0.000 abstract 2
- IGBKNLGEMMEWKD-UHFFFAOYSA-N diosmin Natural products COc1ccc(cc1)C2=C(O)C(=O)c3c(O)cc(OC4OC(COC5OC(C)C(O)C(O)C5O)C(O)C(O)C4O)cc3O2 IGBKNLGEMMEWKD-UHFFFAOYSA-N 0.000 abstract 2
- 229930003949 flavanone Natural products 0.000 abstract 2
- -1 flavanone glycoside Chemical class 0.000 abstract 2
- 235000011981 flavanones Nutrition 0.000 abstract 2
- 229930003944 flavone Natural products 0.000 abstract 2
- 235000011949 flavones Nutrition 0.000 abstract 2
- VHBFFQKBGNRLFZ-UHFFFAOYSA-N vitamin p Natural products O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 abstract 2
- 239000001100 (2S)-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one Substances 0.000 abstract 1
- 239000001606 7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)chroman-4-one Substances 0.000 abstract 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 1
- VCCNKWWXYVWTLT-DGQSHKQTSA-N Diosmetin 7-neohesperidoside Natural products O([C@@H]1[C@@H](O)[C@H](O)[C@H](CO)O[C@H]1Oc1cc(O)c2C(=O)C=C(c3cc(O)c(OC)cc3)Oc2c1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](C)O1 VCCNKWWXYVWTLT-DGQSHKQTSA-N 0.000 abstract 1
- QUQPHWDTPGMPEX-UHFFFAOYSA-N Hesperidine Natural products C1=C(O)C(OC)=CC=C1C1OC2=CC(OC3C(C(O)C(O)C(COC4C(C(O)C(O)C(C)O4)O)O3)O)=CC(O)=C2C(=O)C1 QUQPHWDTPGMPEX-UHFFFAOYSA-N 0.000 abstract 1
- 239000013543 active substance Substances 0.000 abstract 1
- 239000012670 alkaline solution Substances 0.000 abstract 1
- RPMNUQRUHXIGHK-PYXJVEIZSA-N apigenin 7-O-neohesperidoside Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=C2C(=O)C=C(C=3C=CC(O)=CC=3)OC2=C1 RPMNUQRUHXIGHK-PYXJVEIZSA-N 0.000 abstract 1
- 229930034861 apigenin-7-O-neohesperidoside Natural products 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- QUQPHWDTPGMPEX-UTWYECKDSA-N aurantiamarin Natural products COc1ccc(cc1O)[C@H]1CC(=O)c2c(O)cc(O[C@@H]3O[C@H](CO[C@@H]4O[C@@H](C)[C@H](O)[C@@H](O)[C@H]4O)[C@@H](O)[C@H](O)[C@H]3O)cc2O1 QUQPHWDTPGMPEX-UTWYECKDSA-N 0.000 abstract 1
- 210000002421 cell wall Anatomy 0.000 abstract 1
- APSNPMVGBGZYAJ-GLOOOPAXSA-N clematine Natural products COc1cc(ccc1O)[C@@H]2CC(=O)c3c(O)cc(O[C@@H]4O[C@H](CO[C@H]5O[C@@H](C)[C@H](O)[C@@H](O)[C@H]5O)[C@@H](O)[C@H](O)[C@H]4O)cc3O2 APSNPMVGBGZYAJ-GLOOOPAXSA-N 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 150000002208 flavanones Chemical class 0.000 abstract 1
- 150000002212 flavone derivatives Chemical class 0.000 abstract 1
- QUQPHWDTPGMPEX-QJBIFVCTSA-N hesperidin Chemical compound C1=C(O)C(OC)=CC=C1[C@H]1OC2=CC(O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO[C@H]4[C@@H]([C@H](O)[C@@H](O)[C@H](C)O4)O)O3)O)=CC(O)=C2C(=O)C1 QUQPHWDTPGMPEX-QJBIFVCTSA-N 0.000 abstract 1
- 229940025878 hesperidin Drugs 0.000 abstract 1
- 229910052740 iodine Inorganic materials 0.000 abstract 1
- 239000011630 iodine Substances 0.000 abstract 1
- 210000004185 liver Anatomy 0.000 abstract 1
- DFPMSGMNTNDNHN-ZPHOTFPESA-N naringin Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@H]1[C@H](OC=2C=C3O[C@@H](CC(=O)C3=C(O)C=2)C=2C=CC(O)=CC=2)O[C@H](CO)[C@@H](O)[C@@H]1O DFPMSGMNTNDNHN-ZPHOTFPESA-N 0.000 abstract 1
- 229930019673 naringin Natural products 0.000 abstract 1
- 229940052490 naringin Drugs 0.000 abstract 1
- VCCNKWWXYVWTLT-UHFFFAOYSA-N neodiosmin Natural products C1=C(O)C(OC)=CC=C1C(OC1=C2)=CC(=O)C1=C(O)C=C2OC1C(OC2C(C(O)C(O)C(C)O2)O)C(O)C(O)C(CO)O1 VCCNKWWXYVWTLT-UHFFFAOYSA-N 0.000 abstract 1
- ARGKVCXINMKCAZ-UZRWAPQLSA-N neohesperidin Chemical compound C1=C(O)C(OC)=CC=C1[C@H]1OC2=CC(O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O[C@H]3[C@@H]([C@H](O)[C@@H](O)[C@H](C)O3)O)=CC(O)=C2C(=O)C1 ARGKVCXINMKCAZ-UZRWAPQLSA-N 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 230000020477 pH reduction Effects 0.000 abstract 1
- 230000035699 permeability Effects 0.000 abstract 1
- 230000001376 precipitating effect Effects 0.000 abstract 1
- 230000001681 protective effect Effects 0.000 abstract 1
- RPMNUQRUHXIGHK-SBDOOABHSA-N rhoifolin Natural products O([C@@H]1[C@@H](O)[C@H](O)[C@H](CO)O[C@H]1Oc1cc(O)c2C(=O)C=C(c3ccc(O)cc3)Oc2c1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@H](C)O1 RPMNUQRUHXIGHK-SBDOOABHSA-N 0.000 abstract 1
- 230000001256 tonic effect Effects 0.000 abstract 1
- 210000003462 vein Anatomy 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/06—Benzopyran radicals
- C07H17/065—Benzo[b]pyrans
- C07H17/07—Benzo[b]pyran-4-ones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
The flavone glycosides diosmin, neodiosmin or rhoifolin are prepared by oxidation of the flavanone glycosides hesperidin, neohesperidin or naringin by treating the flavanone glycoside with iodine in aqueous alkaline solution, subjecting the resulting intermediate to a treatment in strongly alkaline aqueous solution and then precipitating the flavone glycoside by acidification and removing it. The compounds are employed as pharmaceutical active substances. They have an effect on the permeability of cell walls. Diosmin can be employed as vein tonic and as liver protective.
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES465156A ES465156A1 (en) | 1977-12-16 | 1977-12-16 | Procedure for preparing glycosides with an unsaturated aglicon. (Machine-translation by Google Translate, not legally binding) |
| DE19782844454 DE2844454A1 (en) | 1977-12-16 | 1978-10-12 | METHOD FOR PRODUCING FLAVONE GLYCOSIDES |
| FR7835053A FR2411845A1 (en) | 1977-12-16 | 1978-12-13 | PROCESS FOR THE PREPARATION OF FLAVONE GLUCOSIDES |
| CH1274478A CH644132A5 (en) | 1977-12-16 | 1978-12-14 | Process for the preparation of the flavone glycosides diosmin, neodiosmin and rhoifolin |
| IT52295/78A IT1157742B (en) | 1977-12-16 | 1978-12-14 | PROCESS FOR THE PRODUCTION OF FLAVONGLICOSIDES |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES465156A ES465156A1 (en) | 1977-12-16 | 1977-12-16 | Procedure for preparing glycosides with an unsaturated aglicon. (Machine-translation by Google Translate, not legally binding) |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES465156A1 true ES465156A1 (en) | 1978-10-01 |
Family
ID=8475111
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES465156A Expired ES465156A1 (en) | 1977-12-16 | 1977-12-16 | Procedure for preparing glycosides with an unsaturated aglicon. (Machine-translation by Google Translate, not legally binding) |
Country Status (5)
| Country | Link |
|---|---|
| CH (1) | CH644132A5 (en) |
| DE (1) | DE2844454A1 (en) |
| ES (1) | ES465156A1 (en) |
| FR (1) | FR2411845A1 (en) |
| IT (1) | IT1157742B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2740950A1 (en) * | 1977-09-10 | 1979-03-22 | Merck Patent Gmbh | METHOD OF MANUFACTURING FLAVONS |
| FR2782518A1 (en) * | 1998-08-19 | 2000-02-25 | Innokem Sarl | Preparation of vasotropic diosmin from hesperidin by anhydrous reaction with iodine and pyridine with solid mineral base |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH602778A5 (en) * | 1975-05-16 | 1978-07-31 | Hommel Ag |
-
1977
- 1977-12-16 ES ES465156A patent/ES465156A1/en not_active Expired
-
1978
- 1978-10-12 DE DE19782844454 patent/DE2844454A1/en not_active Withdrawn
- 1978-12-13 FR FR7835053A patent/FR2411845A1/en active Granted
- 1978-12-14 CH CH1274478A patent/CH644132A5/en not_active IP Right Cessation
- 1978-12-14 IT IT52295/78A patent/IT1157742B/en active
Also Published As
| Publication number | Publication date |
|---|---|
| CH644132A5 (en) | 1984-07-13 |
| DE2844454A1 (en) | 1979-06-21 |
| IT1157742B (en) | 1987-02-18 |
| FR2411845B1 (en) | 1982-12-31 |
| FR2411845A1 (en) | 1979-07-13 |
| IT7852295A0 (en) | 1978-12-14 |
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