PL422924A1 - 7-propoxy-naringenin, 7,4'-dipropoxy-naringenin and method for simultaneously obtaining 7-propoxy-naringenin and 7,4'-dipropoxy-naringenin - Google Patents
7-propoxy-naringenin, 7,4'-dipropoxy-naringenin and method for simultaneously obtaining 7-propoxy-naringenin and 7,4'-dipropoxy-naringeninInfo
- Publication number
- PL422924A1 PL422924A1 PL422924A PL42292417A PL422924A1 PL 422924 A1 PL422924 A1 PL 422924A1 PL 422924 A PL422924 A PL 422924A PL 42292417 A PL42292417 A PL 42292417A PL 422924 A1 PL422924 A1 PL 422924A1
- Authority
- PL
- Poland
- Prior art keywords
- naringenin
- dipropoxy
- propoxy
- organic solvent
- evaporated
- Prior art date
Links
- 229940117954 naringenin Drugs 0.000 title abstract 5
- 238000000034 method Methods 0.000 title abstract 3
- 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
- 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
- PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 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-propoksynaringenina o wzorze 2 i sposób otrzymywania tego związku. Sposób ten polega na tym, że do substratu, którym jest naringenina o wzorze 1 dodaje się węglan potasu K2CO3 oraz 1-jodopropan 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 25°C do 45°C na okres od 24 do 72 godzin przy ciągłym mieszaniu, po czym rozpuszczalnik organiczny się odparowuje, 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, a rozpuszczalnik odparowuje się, następnie otrzymany ekstrakt oczyszcza się na kolumnie chromatograficznej.The subject of the application is 7-propoxynaringenin of formula 2 and the method of obtaining this compound. This method consists in the addition of K2CO3 potassium carbonate and 1-iodopropane 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 light and left at 25 ° C to 45 ° C for 24 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, and the solvent is evaporated off, then the obtained extract is purified by column chromatography.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL422924A PL233277B1 (en) | 2017-09-21 | 2017-09-21 | 7-propoxy-naringenin, 7,4'-dipropoxy-naringenin and method for simultaneously obtaining 7-propoxy-naringenin and 7,4'-dipropoxy-naringenin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL422924A PL233277B1 (en) | 2017-09-21 | 2017-09-21 | 7-propoxy-naringenin, 7,4'-dipropoxy-naringenin and method for simultaneously obtaining 7-propoxy-naringenin and 7,4'-dipropoxy-naringenin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL422924A1 true PL422924A1 (en) | 2019-03-25 |
| PL233277B1 PL233277B1 (en) | 2019-09-30 |
Family
ID=65799963
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL422924A PL233277B1 (en) | 2017-09-21 | 2017-09-21 | 7-propoxy-naringenin, 7,4'-dipropoxy-naringenin and method for simultaneously obtaining 7-propoxy-naringenin and 7,4'-dipropoxy-naringenin |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL233277B1 (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20090027412A (en) * | 2007-09-12 | 2009-03-17 | 건국대학교 산학협력단 | Novel flavonoid derivatives 7-O- (3-benzyloxypropyl) -5,4-O-dimethyl-apigenin having anticancer properties, preparations and anticancer compositions comprising the same |
-
2017
- 2017-09-21 PL PL422924A patent/PL233277B1/en unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20090027412A (en) * | 2007-09-12 | 2009-03-17 | 건국대학교 산학협력단 | Novel flavonoid derivatives 7-O- (3-benzyloxypropyl) -5,4-O-dimethyl-apigenin having anticancer properties, preparations and anticancer compositions comprising the same |
Non-Patent Citations (2)
| Title |
|---|
| SUN HEE MOON ET AL., ANTIMICROBIAL EFFECT OF 7-O-BUTYLNARINGENIN, A NOVEL FLAVONOID, AND VARIOUS NATURAL FLAVONOIDS AGAINST HELICOBACTER PYLORI STRAINS, 2013 * |
| SU-YOU LIU ET AL., SYNTHESIS AND ANTIPROLIFERATIVE PROPERTIES OF NOVEL NARINGENIN DERIVATIVES, 11 July 2017 (2017-07-11) * |
Also Published As
| Publication number | Publication date |
|---|---|
| PL233277B1 (en) | 2019-09-30 |
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