GB797186A - Improvements in or relating to bismuth salts - Google Patents
Improvements in or relating to bismuth saltsInfo
- Publication number
- GB797186A GB797186A GB3611656A GB3611656A GB797186A GB 797186 A GB797186 A GB 797186A GB 3611656 A GB3611656 A GB 3611656A GB 3611656 A GB3611656 A GB 3611656A GB 797186 A GB797186 A GB 797186A
- Authority
- GB
- United Kingdom
- Prior art keywords
- bismuth
- aqueous
- solution
- quercetin
- salt
- 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
- 150000001621 bismuth Chemical class 0.000 title abstract 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 6
- REFJWTPEDVJJIY-UHFFFAOYSA-N Quercetin Chemical compound C=1C(O)=CC(O)=C(C(C=2O)=O)C=1OC=2C1=CC=C(O)C(O)=C1 REFJWTPEDVJJIY-UHFFFAOYSA-N 0.000 abstract 6
- HVQAJTFOCKOKIN-UHFFFAOYSA-N flavonol Natural products O1C2=CC=CC=C2C(=O)C(O)=C1C1=CC=CC=C1 HVQAJTFOCKOKIN-UHFFFAOYSA-N 0.000 abstract 5
- SOEDEYVDCDYMMH-UHFFFAOYSA-N robinetin Chemical compound C=1C(O)=CC=C(C(C=2O)=O)C=1OC=2C1=CC(O)=C(O)C(O)=C1 SOEDEYVDCDYMMH-UHFFFAOYSA-N 0.000 abstract 5
- 239000000243 solution Substances 0.000 abstract 5
- 229910052784 alkaline earth metal Chemical class 0.000 abstract 4
- 229910052797 bismuth Inorganic materials 0.000 abstract 4
- ZVOLCUVKHLEPEV-UHFFFAOYSA-N Quercetagetin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=C(O)C(O)=C(O)C=C2O1 ZVOLCUVKHLEPEV-UHFFFAOYSA-N 0.000 abstract 3
- HWTZYBCRDDUBJY-UHFFFAOYSA-N Rhynchosin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=CC(O)=C(O)C=C2O1 HWTZYBCRDDUBJY-UHFFFAOYSA-N 0.000 abstract 3
- MWDZOUNAPSSOEL-UHFFFAOYSA-N kaempferol Natural products OC1=C(C(=O)c2cc(O)cc(O)c2O1)c3ccc(O)cc3 MWDZOUNAPSSOEL-UHFFFAOYSA-N 0.000 abstract 3
- 239000000203 mixture Substances 0.000 abstract 3
- 235000005875 quercetin Nutrition 0.000 abstract 3
- 229960001285 quercetin Drugs 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- ZZLQHXCRRMUGQJ-UHFFFAOYSA-N 2'-Hydroxyflavone Natural products OC1=CC=CC=C1C1=CC(=O)C2=CC=CC=C2O1 ZZLQHXCRRMUGQJ-UHFFFAOYSA-N 0.000 abstract 2
- HWSISDHAHRVNMT-UHFFFAOYSA-N Bismuth subnitrate Chemical compound O[NH+]([O-])O[Bi](O[N+]([O-])=O)O[N+]([O-])=O HWSISDHAHRVNMT-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- 239000003513 alkali Chemical class 0.000 abstract 2
- 150000001342 alkaline earth metals Chemical class 0.000 abstract 2
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 abstract 2
- -1 bismuth quercetin salt Chemical class 0.000 abstract 2
- XHEFDIBZLJXQHF-UHFFFAOYSA-N fisetin Chemical compound C=1C(O)=CC=C(C(C=2O)=O)C=1OC=2C1=CC=C(O)C(O)=C1 XHEFDIBZLJXQHF-UHFFFAOYSA-N 0.000 abstract 2
- 150000007946 flavonol Chemical class 0.000 abstract 2
- 235000011957 flavonols Nutrition 0.000 abstract 2
- 239000002244 precipitate Substances 0.000 abstract 2
- VZZHAYFWMLLWGG-UHFFFAOYSA-K triazanium;bismuth;2-hydroxypropane-1,2,3-tricarboxylate Chemical compound [NH4+].[NH4+].[NH4+].[Bi+3].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O VZZHAYFWMLLWGG-UHFFFAOYSA-K 0.000 abstract 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 1
- QYIGOGBGVKONDY-UHFFFAOYSA-N 1-(2-bromo-5-chlorophenyl)-3-methylpyrazole Chemical compound N1=C(C)C=CN1C1=CC(Cl)=CC=C1Br QYIGOGBGVKONDY-UHFFFAOYSA-N 0.000 abstract 1
- BNGQZUVOCHUVHD-UHFFFAOYSA-N [Bi].O1C(=C(C(=O)C2=CC=CC=C12)O)C1=CC=CC=C1 Chemical compound [Bi].O1C(=C(C(=O)C2=CC=CC=C12)O)C1=CC=CC=C1 BNGQZUVOCHUVHD-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 229940049676 bismuth hydroxide Drugs 0.000 abstract 1
- 229960001482 bismuth subnitrate Drugs 0.000 abstract 1
- HHYMEKJYIHGLST-OLXYHTOASA-L bismuth;potassium;(2r,3r)-2,3-dioxidobutanedioate Chemical compound [K+].[Bi+3].[O-]C(=O)[C@H]([O-])[C@@H]([O-])C([O-])=O HHYMEKJYIHGLST-OLXYHTOASA-L 0.000 abstract 1
- YPQBHUDKOKUINZ-OLXYHTOASA-L bismuth;sodium;(2r,3r)-2,3-dioxidobutanedioate Chemical compound [Na+].[Bi+3].[O-]C(=O)[C@H]([O-])[C@@H]([O-])C([O-])=O YPQBHUDKOKUINZ-OLXYHTOASA-L 0.000 abstract 1
- TZSXPYWRDWEXHG-UHFFFAOYSA-K bismuth;trihydroxide Chemical compound [OH-].[OH-].[OH-].[Bi+3] TZSXPYWRDWEXHG-UHFFFAOYSA-K 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 235000011990 fisetin Nutrition 0.000 abstract 1
- RXPAJWPEYBDXOG-UHFFFAOYSA-N hydron;methyl 4-methoxypyridine-2-carboxylate;chloride Chemical compound Cl.COC(=O)C1=CC(OC)=CC=N1 RXPAJWPEYBDXOG-UHFFFAOYSA-N 0.000 abstract 1
- 230000007935 neutral effect Effects 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- LJCNRYVRMXRIQR-OLXYHTOASA-L potassium sodium L-tartrate Chemical compound [Na+].[K+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O LJCNRYVRMXRIQR-OLXYHTOASA-L 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 239000001476 sodium potassium tartrate Substances 0.000 abstract 1
- 235000011006 sodium potassium tartrate Nutrition 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 238000003756 stirring Methods 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
- C07D311/30—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only not hydrogenated in the hetero ring, e.g. flavones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/94—Bismuth compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises bismuth salts of mono- and poly-hydroxy-flavones, particularly of flavonol (3-hydroxy-), quercetin (3,5,7,31,41-pentahydroxy-), robinetin (3,7,31,41,51-pentahydroxy-), fisetin (3,7,31,41-tetrahydroxy-), and quercetagin (3,5,6,7,31,41-hexahydroxyflavone), and their preparation by reaction of a water-soluble salt of bismuth (which may be a complex salt) with the free hydroxyflavone or an alkali or alkaline earth metal derivative thereof. Preferably the free hydroxyflavones are reacted with complex salts, e.g. bismuth ammonium citrate, bismuth potassium tartrate, and bismuth sodium tartrate, in a water-miscible organic solvent, e.g. methanol, ethanol, and dioxan, at the boiling-point of the solvent; whereas the alkali or alkaline earth metal derivatives are preferably reacted in aqueous solution with e.g. bismuth acetate or subnitrate, the bismuth salt being kept in solution by means of acid if required. The proportions of reactants are normally such that the resulting compounds contain one gram-atom of bismuth per gram-mol. of the hydroxyflavone. In examples: (1) quercetin in boiling methanol is treated with aqueous bismuth ammonium citrate, when the bismuth-quercetin salt precipitates; (2) quercetin is dissolved in a solution of sodium potassium tartrate and bismuth subnitrate in aqueous NaOH, and the mixture poured with stirring into aqueous acetic acid, when the bismuth quercetin salt separates from the neutral solution; (3) a solution of bismuth hydroxide in aqueous acetic acid is run into aqueous NaOH containing robinetin, the mixture stirred and the precipitated bismuth robinetin compound isolated; (4) bismuth nitrate in aqueous acetic acid is added to a solution of flavonol in aqueous ethanolic NaOH, the pH adjusted to 7, and mixture heated, when the flavonol bismuth compound precipitates.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC13258A DE1003751B (en) | 1956-06-23 | 1956-06-23 | Process for the preparation of bismuth salts of oxyflavone compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB797186A true GB797186A (en) | 1958-06-25 |
Family
ID=7015399
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3611656A Expired GB797186A (en) | 1956-06-23 | 1956-11-26 | Improvements in or relating to bismuth salts |
| GB1936357A Expired GB815877A (en) | 1956-06-23 | 1957-06-19 | Improvements in or relating to bismuth salts |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1936357A Expired GB815877A (en) | 1956-06-23 | 1957-06-19 | Improvements in or relating to bismuth salts |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE1003751B (en) |
| FR (1) | FR1160936A (en) |
| GB (2) | GB797186A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112494402A (en) * | 2020-12-22 | 2021-03-16 | 广东丸美生物技术股份有限公司 | Iris root extract and preparation method and application thereof |
-
1956
- 1956-06-23 DE DEC13258A patent/DE1003751B/en active Pending
- 1956-11-26 GB GB3611656A patent/GB797186A/en not_active Expired
- 1956-11-28 FR FR1160936D patent/FR1160936A/en not_active Expired
-
1957
- 1957-06-19 GB GB1936357A patent/GB815877A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112494402A (en) * | 2020-12-22 | 2021-03-16 | 广东丸美生物技术股份有限公司 | Iris root extract and preparation method and application thereof |
| CN112494402B (en) * | 2020-12-22 | 2022-07-01 | 广东丸美生物技术股份有限公司 | Iris root extract and preparation method and application thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1160936A (en) | 1958-08-13 |
| GB815877A (en) | 1959-07-01 |
| DE1003751B (en) | 1957-03-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB1108975A (en) | New sulphonic acid and process for its production | |
| GB797186A (en) | Improvements in or relating to bismuth salts | |
| SE439482B (en) | Method of producing p- hydroxyphenylglycine | |
| US2370592A (en) | Sulphauro compounds and processes for their production | |
| ES319653A1 (en) | A procedure for the preparation of imidazole derivatives. (Machine-translation by Google Translate, not legally binding) | |
| US2370593A (en) | Sulphauro compounds and processes for their production | |
| US2791590A (en) | Novel pyran compounds | |
| SE8600912D0 (en) | PROCEDURE FOR THE PREPARATION OF A POWDER-SHEET IRON TARTRATE SODIUM COMPLEX | |
| GB1318298A (en) | 0,0-dialkyllthiophosphoric and 0,0-dialkyl-dithiophosphoric esters of oxadiazoles | |
| GB845649A (en) | 6-deoxytetracycline and 6-deoxyoxytetracycline | |
| GB584196A (en) | Improvements in and relating to the manufacture of derivatives of disubstituted methane compounds | |
| CA1150276A (en) | Process for the preparation of benzoxazolone | |
| US4237295A (en) | Process for the production of 17-hydroxysparteine by oxidation of sparteine with a permanganate | |
| GB932523A (en) | Process for the production of lead hydroxide oxide of the formula 5 pbo.2ho | |
| GB816236A (en) | Improvements in the preparation of phenanthridine compounds | |
| SU405890A1 (en) | In P T B,.> &. ^ ••• ^. •; '1; • -, |! ? n-jTt V ^ 1 t ^ -TI | |
| US2463819A (en) | Preparation of acylguanylthioureas | |
| GB1197137A (en) | Substituted Indanones and their Preparation and Reactions | |
| US1667237A (en) | Process for the preparation of organic arsenic compounds | |
| Moore et al. | ι-Aurothio Fatty Acids and their Salts | |
| GB1219848A (en) | NOVEL N-SUBSTITUTED-o-PHENYLENE AMINES, AND PROCESSES FOR THEIR PREPARATION | |
| GB559338A (en) | Thiazyl sulphides | |
| JPS5821636B2 (en) | Diumycin A Diumycin A; | |
| ES464461A1 (en) | Ammelide derivative and its preparation | |
| Galinowski et al. | 437. Products of nitration of some derivatives of dimethylaniline, auramine, and crystal-violet |