PL432129A1 - Sposób wytwarzania ksantohumolu - Google Patents
Sposób wytwarzania ksantohumoluInfo
- Publication number
- PL432129A1 PL432129A1 PL432129A PL43212919A PL432129A1 PL 432129 A1 PL432129 A1 PL 432129A1 PL 432129 A PL432129 A PL 432129A PL 43212919 A PL43212919 A PL 43212919A PL 432129 A1 PL432129 A1 PL 432129A1
- Authority
- PL
- Poland
- Prior art keywords
- chalcone
- xanthohumol
- group
- naringenin
- flavone
- Prior art date
Links
- YKGCBLWILMDSAV-GOSISDBHSA-N Isoxanthohumol Natural products O(C)c1c2C(=O)C[C@H](c3ccc(O)cc3)Oc2c(C/C=C(\C)/C)c(O)c1 YKGCBLWILMDSAV-GOSISDBHSA-N 0.000 title abstract 5
- FUSADYLVRMROPL-UHFFFAOYSA-N demethylxanthohumol Natural products CC(C)=CCC1=C(O)C=C(O)C(C(=O)C=CC=2C=CC(O)=CC=2)=C1O FUSADYLVRMROPL-UHFFFAOYSA-N 0.000 title abstract 5
- ORXQGKIUCDPEAJ-YRNVUSSQSA-N xanthohumol Chemical compound COC1=CC(O)=C(CC=C(C)C)C(O)=C1C(=O)\C=C\C1=CC=C(O)C=C1 ORXQGKIUCDPEAJ-YRNVUSSQSA-N 0.000 title abstract 5
- UVBDKJHYMQEAQV-UHFFFAOYSA-N xanthohumol Natural products OC1=C(CC=C(C)C)C(OC)=CC(OC)=C1C(=O)C=CC1=CC=C(O)C=C1 UVBDKJHYMQEAQV-UHFFFAOYSA-N 0.000 title abstract 5
- 235000008209 xanthohumol Nutrition 0.000 title abstract 5
- 238000004519 manufacturing process Methods 0.000 title 1
- DQFBYFPFKXHELB-UHFFFAOYSA-N Chalcone Natural products C=1C=CC=CC=1C(=O)C=CC1=CC=CC=C1 DQFBYFPFKXHELB-UHFFFAOYSA-N 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- 235000005513 chalcones Nutrition 0.000 abstract 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 3
- DQFBYFPFKXHELB-VAWYXSNFSA-N trans-chalcone Chemical compound C=1C=CC=CC=1C(=O)\C=C\C1=CC=CC=C1 DQFBYFPFKXHELB-VAWYXSNFSA-N 0.000 abstract 3
- 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 2
- 230000010933 acylation Effects 0.000 abstract 2
- 238000005917 acylation reaction Methods 0.000 abstract 2
- -1 chalcone compound Chemical class 0.000 abstract 2
- VHBFFQKBGNRLFZ-UHFFFAOYSA-N flavone Chemical group O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- 229940117954 naringenin Drugs 0.000 abstract 2
- 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 2
- 235000007625 naringenin Nutrition 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 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 238000005804 alkylation reaction Methods 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000004185 ester group Chemical group 0.000 abstract 1
- 229930003944 flavone Natural products 0.000 abstract 1
- 150000002212 flavone derivatives Chemical class 0.000 abstract 1
- 235000011949 flavones Nutrition 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 230000000269 nucleophilic effect Effects 0.000 abstract 1
- 239000003880 polar aprotic solvent Substances 0.000 abstract 1
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 1
- 238000006467 substitution reaction Methods 0.000 abstract 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Przedmiotem zgłoszenia jest sposób wytwarzania ksantohumolu (XN) charakteryzujący się tym, że ksantohumol wytwarza się z naringeniny w procesie, w którym: acyluje się grupy hydroksylowe przy atomach węgla 7 i 4' ugrupowania flawonowego naringeniny uzyskując produkt acylowania, produkt acylowania poddaje się reakcji alkilowania wolnego ugrupowania hydroksylowego do alkoksylowego i reakcji przekształcenia ugrupowania flawonowego do ugrupowania chalkonowego, w obecności nienukleofilowej zasady, w polarnym rozpuszczalniku aprotycznym, uzyskując związek chalkonowy. Natomiast uzyskany związek chalkonowy poddaje się kolejno: reakcji hydrolizy jego grup estrowych przy atomach węgla 4, 4' i 6 ugrupowania chalkonowego do grup hydroksylowych oraz reakcji podstawienia ugrupowania prenylowego przy atomie węgla 5' ugrupowania chalkonowego, uzyskując ksantohumol.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL432129A PL239472B1 (pl) | 2019-12-10 | 2019-12-10 | Sposób wytwarzania ksantohumolu |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL432129A PL239472B1 (pl) | 2019-12-10 | 2019-12-10 | Sposób wytwarzania ksantohumolu |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL432129A1 true PL432129A1 (pl) | 2021-06-14 |
| PL239472B1 PL239472B1 (pl) | 2021-12-06 |
Family
ID=76321280
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL432129A PL239472B1 (pl) | 2019-12-10 | 2019-12-10 | Sposób wytwarzania ksantohumolu |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL239472B1 (pl) |
-
2019
- 2019-12-10 PL PL432129A patent/PL239472B1/pl unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL239472B1 (pl) | 2021-12-06 |
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