PL421045A1 - 7-dodecanoxy-naringenin and 7,4'-didodecanoxy-naringenin and method for simultaneously obtaining 7-dodecanoxy-naringenin and 7,4'-didodecanoxy-naringenin - Google Patents
7-dodecanoxy-naringenin and 7,4'-didodecanoxy-naringenin and method for simultaneously obtaining 7-dodecanoxy-naringenin and 7,4'-didodecanoxy-naringeninInfo
- Publication number
- PL421045A1 PL421045A1 PL421045A PL42104517A PL421045A1 PL 421045 A1 PL421045 A1 PL 421045A1 PL 421045 A PL421045 A PL 421045A PL 42104517 A PL42104517 A PL 42104517A PL 421045 A1 PL421045 A1 PL 421045A1
- Authority
- PL
- Poland
- Prior art keywords
- naringenin
- organic solvent
- didodecanoxy
- dodecanoxy
- evaporated
- Prior art date
Links
- 229940117954 naringenin Drugs 0.000 title abstract 5
- 238000000034 method Methods 0.000 title abstract 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 abstract 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 abstract 3
- 239000003960 organic solvent Substances 0.000 abstract 3
- 229910000027 potassium carbonate Inorganic materials 0.000 abstract 2
- 238000003756 stirring Methods 0.000 abstract 2
- FTVWIRXFELQLPI-ZDUSSCGKSA-N (S)-naringenin Chemical compound C1=CC(O)=CC=C1[C@H]1OC2=CC(O)=CC(O)=C2C(=O)C1 FTVWIRXFELQLPI-ZDUSSCGKSA-N 0.000 abstract 1
- GCDPERPXPREHJF-UHFFFAOYSA-N 1-iodododecane Chemical compound CCCCCCCCCCCCI GCDPERPXPREHJF-UHFFFAOYSA-N 0.000 abstract 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 abstract 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 abstract 1
- 238000004440 column chromatography Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000000605 extraction Methods 0.000 abstract 1
- WGEYAGZBLYNDFV-UHFFFAOYSA-N naringenin Natural products C1(=O)C2=C(O)C=C(O)C=C2OC(C1)C1=CC=C(CC1)O WGEYAGZBLYNDFV-UHFFFAOYSA-N 0.000 abstract 1
- 235000007625 naringenin Nutrition 0.000 abstract 1
- 235000015320 potassium carbonate Nutrition 0.000 abstract 1
- 235000011181 potassium carbonates Nutrition 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 239000011780 sodium chloride Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000000758 substrate Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Abstract
Przedmiotem zgłoszenia jest 7-dodekanoksynaringenina oraz 7,4'-didodekanoksynaringenina oraz sposób wytwarzania tych związków. Wynalazek polega na tym, że do substratu, którym jest naringenina o wzorze 1 dodaje się, węglan potasu K2CO3 oraz 1-jodododekan w stosunku molowym co najmniej 1:1,5:5 oraz minimalną ilość rozpuszczalnika organicznego, co stanowi mieszaninę reakcyjną, którą zabezpiecza się przed dostępem światła i pozostawia w temperaturze od 40°C do 50°C na okres od 48 do 72 godzin przy ciągłym mieszaniu, po czym rozpuszczalnik organiczny odparowuje się, dodaje się nasyconego roztworu chlorku sodu NaCl, a następnie prowadzi się ekstrakcję rozpuszczalnikiem organicznym niemieszającym się z wodą, osusza bezwodnym siarczanem magnezu i/lub bezwodnym siarczanem sodu, rozpuszczalnik odparowuje się, następnie otrzymany ekstrakt oczyszcza się na kolumnie chromatograficznej.The subject of the application is 7-dodecanoxynaringenin and 7,4'-didodecanoxynaringenin and a method for preparing these compounds. The invention consists in the addition of K2CO3 potassium carbonate and 1-iodododecane in a molar ratio of at least 1: 1.5: 5 to the substrate which is naringenin of formula 1 and a minimum amount of organic solvent, which is the reaction mixture it protects before exposure to light and left at a temperature of 40 ° C to 50 ° C for a period of 48 to 72 hours with continuous stirring, after which the organic solvent is evaporated, saturated sodium chloride NaCl solution is added, followed by extraction with a non-stirring organic solvent with water, dried over anhydrous magnesium sulfate and / or anhydrous sodium sulfate, the solvent is evaporated off, then the obtained extract is purified by column chromatography.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL421045A PL236846B1 (en) | 2017-03-29 | 2017-03-29 | 7-dodecanoxy-naringenin and 7,4'-didodecanoxy-naringenin and method for simultaneously obtaining 7-dodecanoxy-naringenin and 7,4'-didodecanoxy-naringenin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL421045A PL236846B1 (en) | 2017-03-29 | 2017-03-29 | 7-dodecanoxy-naringenin and 7,4'-didodecanoxy-naringenin and method for simultaneously obtaining 7-dodecanoxy-naringenin and 7,4'-didodecanoxy-naringenin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL421045A1 true PL421045A1 (en) | 2018-10-08 |
| PL236846B1 PL236846B1 (en) | 2021-02-22 |
Family
ID=63688088
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL421045A PL236846B1 (en) | 2017-03-29 | 2017-03-29 | 7-dodecanoxy-naringenin and 7,4'-didodecanoxy-naringenin and method for simultaneously obtaining 7-dodecanoxy-naringenin and 7,4'-didodecanoxy-naringenin |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL236846B1 (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL443469A1 (en) * | 2023-01-13 | 2024-07-15 | Uniwersytet Przyrodniczy we Wrocławiu | 7,4'-Di-O-octylnaringenin and method for simultaneously obtaining 7,4'-di-O-octylnaringenin and 7-O-octylnaringenin |
| PL443472A1 (en) * | 2023-01-13 | 2024-07-15 | Uniwersytet Przyrodniczy we Wrocławiu | 7-O-Undecylnaringenin and 7,4'-di-O-undecylnaringenin and method of simultaneously obtaining 7-O-undecylnaringenin and 7,4'-di-O-undecylnaringenin |
| PL443468A1 (en) * | 2023-01-13 | 2024-07-15 | Uniwersytet Przyrodniczy we Wrocławiu | 7,4'-Di-O-nonylnaringenin and method of simultaneous preparation of 7,4'-di-O-nonylnaringenin and 7-O-nonylnaringenin. |
| PL443477A1 (en) * | 2023-01-13 | 2024-07-15 | Uniwersytet Przyrodniczy we Wrocławiu | 7,4'-di-O-undecylnaringenin oxime and method of obtaining 7,4'-di-O-undecylnaringenin oxime |
| PL443471A1 (en) * | 2023-01-13 | 2024-07-15 | Uniwersytet Przyrodniczy we Wrocławiu | 7-O-Heptylnaringenin and 7,4'-di-O-heptylnaringenin and method of simultaneous preparation of 7-O-heptylnaringenin and 7,4'-di-O-heptylnaringenin |
-
2017
- 2017-03-29 PL PL421045A patent/PL236846B1/en unknown
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL443469A1 (en) * | 2023-01-13 | 2024-07-15 | Uniwersytet Przyrodniczy we Wrocławiu | 7,4'-Di-O-octylnaringenin and method for simultaneously obtaining 7,4'-di-O-octylnaringenin and 7-O-octylnaringenin |
| PL443472A1 (en) * | 2023-01-13 | 2024-07-15 | Uniwersytet Przyrodniczy we Wrocławiu | 7-O-Undecylnaringenin and 7,4'-di-O-undecylnaringenin and method of simultaneously obtaining 7-O-undecylnaringenin and 7,4'-di-O-undecylnaringenin |
| PL443468A1 (en) * | 2023-01-13 | 2024-07-15 | Uniwersytet Przyrodniczy we Wrocławiu | 7,4'-Di-O-nonylnaringenin and method of simultaneous preparation of 7,4'-di-O-nonylnaringenin and 7-O-nonylnaringenin. |
| PL443477A1 (en) * | 2023-01-13 | 2024-07-15 | Uniwersytet Przyrodniczy we Wrocławiu | 7,4'-di-O-undecylnaringenin oxime and method of obtaining 7,4'-di-O-undecylnaringenin oxime |
| PL443471A1 (en) * | 2023-01-13 | 2024-07-15 | Uniwersytet Przyrodniczy we Wrocławiu | 7-O-Heptylnaringenin and 7,4'-di-O-heptylnaringenin and method of simultaneous preparation of 7-O-heptylnaringenin and 7,4'-di-O-heptylnaringenin |
| PL247539B1 (en) * | 2023-01-13 | 2025-07-21 | Univ Medyczny Im Piastow Slaskich We Wroclawiu | 7,4'-di-O-undecylonaringenin oxime and method for obtaining 7,4'-di-O-undecylonaringenin oxime |
| PL247535B1 (en) * | 2023-01-13 | 2025-07-21 | Univ Medyczny Im Piastow Slaskich We Wroclawiu | 7-O-Undecylnaringenin and 7,4'-di-O-undecylnaringenin and method for simultaneous preparation of 7-O-undecylnaringenin and 7,4'-di-O-undecylnaringenin |
| PL247534B1 (en) * | 2023-01-13 | 2025-07-21 | Univ Medyczny Im Piastow Slaskich We Wroclawiu | 7-O-Heptylonaringenin and 7,4'-di-O-heptylonaringenin and method for simultaneous preparation of 7-O-heptylonaringenin and 7,4'-di-O-heptylonaringenin |
| PL247533B1 (en) * | 2023-01-13 | 2025-07-21 | Univ Medyczny Im Piastow Slaskich We Wroclawiu | 7,4'-Di-O-nonylnaringenin and method for simultaneous preparation of 7,4'-di-O-nonylnaringenin and 7-O-nonylnaringenin |
| PL247911B1 (en) * | 2023-01-13 | 2025-09-15 | Univ Medyczny Im Piastow Slaskich We Wroclawiu | 7,4'-Di-O-octylnaringenin and method for simultaneously obtaining 7,4'-di-O-octylnaringenin and 7-O-octylnaringenin |
Also Published As
| Publication number | Publication date |
|---|---|
| PL236846B1 (en) | 2021-02-22 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| PL421030A1 (en) | 7-pentoxy-naringenin and 7,4'-dipentoxy-naringenin and method for simultaneously obtaining 7-pentoxy-naringenin and 7,4'-dipentoxy-naringenin | |
| BR112013003147A8 (en) | COMPOSITION AND METHOD OF CONTROLLING PLANT DISEASES COMPRISING A PYRIDAZINE COMPOUND | |
| PL422923A1 (en) | 7-isopropoxy-naringenin and 7,4'-diisopropoxy-naringenin and method for simultaneously obtaining 7-isopropoxy-naringenin and 7,4'-diisopropoxy-naringenin | |
| MX375261B (en) | SUBSTITUTED AROMATIC COMPOUNDS FOR THE TREATMENT OF PULMONARY FIBROSIS, LIVER FIBROSIS, SKIN FIBROSIS AND CARDIAC FIBROSIS. | |
| PE20160120A1 (en) | DERIVATIVES OF NUCLEOSIDE 4'-FLUORO-2'-METHYL SUBSTITUTED | |
| BR112021024039A2 (en) | Syntheses of substituted furans | |
| PH12021551495A1 (en) | Crystalline and salt forms of an organic compound and pharmaceutical compositions thereof | |
| PL421047A1 (en) | 7,4'-didodecanoxy-naringenin-oxime and method for obtaining 7,4'-didodecanoxy-naringenin-oxime | |
| PL422928A1 (en) | 7,4'-dibutoxy-naringenin and method for simultaneously obtaining 7,4'-dibutoxy-naringenin and 7-butoxy-naringenin | |
| PL422924A1 (en) | 7-propoxy-naringenin, 7,4'-dipropoxy-naringenin and method for simultaneously obtaining 7-propoxy-naringenin and 7,4'-dipropoxy-naringenin | |
| PL422929A1 (en) | 7,4'-didecanoxy-naringenin and method for simultaneously obtaining 7,4'-didecanoxy-naringenin and 7-decanoxy-naringenin | |
| BR112016026310A8 (en) | process for the reaction of chemical compounds | |
| PL443472A1 (en) | 7-O-Undecylnaringenin and 7,4'-di-O-undecylnaringenin and method of simultaneously obtaining 7-O-undecylnaringenin and 7,4'-di-O-undecylnaringenin | |
| PL443469A1 (en) | 7,4'-Di-O-octylnaringenin and method for simultaneously obtaining 7,4'-di-O-octylnaringenin and 7-O-octylnaringenin | |
| PL422925A1 (en) | 5,7,4'-tripropoxynaringenin and method for obtaining 5,7,4'-tripropoxynaringenin | |
| PL443468A1 (en) | 7,4'-Di-O-nonylnaringenin and method of simultaneous preparation of 7,4'-di-O-nonylnaringenin and 7-O-nonylnaringenin. | |
| PL443471A1 (en) | 7-O-Heptylnaringenin and 7,4'-di-O-heptylnaringenin and method of simultaneous preparation of 7-O-heptylnaringenin and 7,4'-di-O-heptylnaringenin | |
| PL434619A1 (en) | 7-O-Hexylnaringenin and 7,4'-di-O-hexylnaringenin and their simultaneous preparation | |
| EP3741764A4 (en) | SYNTHESIS OF BORONIC ACID ESTER COMPOUND, AND SODIUM SALT OF BORONIC ACID ESTER COMPOUND, AND PROCESS FOR SYNTHESIS | |
| PL422403A1 (en) | 2'-hydroxy-4-butylchalcone and method for obtaining 2'-hydroxy-4-butylchalcone | |
| PL421046A1 (en) | 7-dodecanoxy-naringenin-oxime and method for obtaining 7-dodecanoxy-naringenin-oxime | |
| PL419749A1 (en) | 3'-Amino-3-methoxy-4-benzyloxychalcone and method for obtaining 3'-amino-3-methoxy-4-benzyloxychalcone | |
| PL419746A1 (en) | 3'-Amino-4-ethylchalcone and method for obtaining 3'-amino-4-ethylchalcone | |
| PL431215A1 (en) | Crystalline form of azide bis(L-arginine)chlorine-copper(Il)bis(L-arginine)diazido-copper(II) hydrate 1/7 complex and method of its production | |
| PL419748A1 (en) | 3'-Amino-4-benzyloxychalcone and method for obtaining 3'-amino-4-benzyloxychalcone |