ES8706659A1 - Prodn. of diosmin from hesperidin - Google Patents
Prodn. of diosmin from hesperidinInfo
- Publication number
- ES8706659A1 ES8706659A1 ES555384A ES555384A ES8706659A1 ES 8706659 A1 ES8706659 A1 ES 8706659A1 ES 555384 A ES555384 A ES 555384A ES 555384 A ES555384 A ES 555384A ES 8706659 A1 ES8706659 A1 ES 8706659A1
- Authority
- ES
- Spain
- Prior art keywords
- prodn
- diosmin
- hesperidin
- solvent
- effected
- 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
- 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 title abstract 2
- 229960004352 diosmin Drugs 0.000 title abstract 2
- 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 title 2
- 239000001100 (2S)-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one Substances 0.000 title 1
- 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 title 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 title 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 title 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 title 1
- 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 title 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 title 1
- 229940025878 hesperidin Drugs 0.000 title 1
- 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 title 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 abstract 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- -1 poly(4-vinylpyridine) Polymers 0.000 abstract 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 abstract 1
- 229910052740 iodine Inorganic materials 0.000 abstract 1
- 239000011630 iodine Substances 0.000 abstract 1
- 150000007530 organic bases Chemical class 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 239000003880 polar aprotic solvent Substances 0.000 abstract 1
- 229920000075 poly(4-vinylpyridine) Polymers 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 239000002904 solvent Substances 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)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Prodn. of diosmine (I) is effected by treating esperidine (II) with iodine in an inert organic solvent and eliminatinq HI with an organic base. - Pref. reaction is effected at between room temp. and 120 deg.C. The solvent is a polar aprotic solvent, esp. DMF, dimethylacetamide or DMSO. The base is pyridine or poly(4-vinylpyridine).
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT8520974A IT1191620B (en) | 1985-05-30 | 1985-05-30 | PROCEDURE FOR THE PREPARATION OF DIOSMINE |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| ES555384A0 ES555384A0 (en) | 1987-07-16 |
| ES8706659A1 true ES8706659A1 (en) | 1987-07-16 |
Family
ID=11174849
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES555384A Expired ES8706659A1 (en) | 1985-05-30 | 1986-05-28 | Prodn. of diosmin from hesperidin |
Country Status (3)
| Country | Link |
|---|---|
| BE (1) | BE904614A (en) |
| ES (1) | ES8706659A1 (en) |
| IT (1) | IT1191620B (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2760016B1 (en) * | 1997-02-21 | 1999-05-28 | Innokem Sarl | PROCESS FOR THE INDUSTRIAL MANUFACTURE OF DIOSMINE FROM HESPERIDINE |
| FR2760015B1 (en) * | 1997-02-21 | 1999-05-28 | Innokem Sarl | PROCESS FOR THE INDUSTRIAL MANUFACTURE OF DIOSMINE FROM HESPERIDINE |
| 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 |
| EP3053930A1 (en) | 2015-02-03 | 2016-08-10 | Interquim, S.A. | Process for the preparation of diosmin |
| EP3321273B1 (en) * | 2016-08-30 | 2022-02-23 | Chengdu Okay Pharmaceutical Co., Ltd | Preparation method of diosmin |
-
1985
- 1985-05-30 IT IT8520974A patent/IT1191620B/en active
-
1986
- 1986-04-17 BE BE0/216543A patent/BE904614A/en not_active IP Right Cessation
- 1986-05-28 ES ES555384A patent/ES8706659A1/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ES555384A0 (en) | 1987-07-16 |
| BE904614A (en) | 1986-08-18 |
| IT8520974A0 (en) | 1985-05-30 |
| IT1191620B (en) | 1988-03-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Patent lapsed |
Effective date: 19960506 |