GB875164A - New hydroxyflavones, their production and use as anti-oxidants - Google Patents
New hydroxyflavones, their production and use as anti-oxidantsInfo
- Publication number
- GB875164A GB875164A GB24031/56A GB2403156A GB875164A GB 875164 A GB875164 A GB 875164A GB 24031/56 A GB24031/56 A GB 24031/56A GB 2403156 A GB2403156 A GB 2403156A GB 875164 A GB875164 A GB 875164A
- Authority
- GB
- United Kingdom
- Prior art keywords
- groups
- positions
- hydroxy
- alkyl
- substituted
- 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
- HVQAJTFOCKOKIN-UHFFFAOYSA-N flavonol Chemical class O1C2=CC=CC=C2C(=O)C(O)=C1C1=CC=CC=C1 HVQAJTFOCKOKIN-UHFFFAOYSA-N 0.000 title abstract 3
- 239000003963 antioxidant agent Substances 0.000 title abstract 2
- 235000006708 antioxidants Nutrition 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 6
- 125000003545 alkoxy group Chemical group 0.000 abstract 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 4
- 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 4
- SULYEHHGGXARJS-UHFFFAOYSA-N 2',4'-dihydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1O SULYEHHGGXARJS-UHFFFAOYSA-N 0.000 abstract 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- 229930003944 flavone Natural products 0.000 abstract 3
- 235000011949 flavones Nutrition 0.000 abstract 3
- 230000003647 oxidation Effects 0.000 abstract 3
- 238000007254 oxidation reaction Methods 0.000 abstract 3
- 125000006239 protecting group Chemical group 0.000 abstract 3
- FZHSPPYCNDYIKD-UHFFFAOYSA-N 5-methoxysalicylaldehyde Chemical compound COC1=CC=C(O)C(C=O)=C1 FZHSPPYCNDYIKD-UHFFFAOYSA-N 0.000 abstract 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 2
- UILPJVPSNHJFIK-UHFFFAOYSA-N Paeonol Chemical compound COC1=CC=C(C(C)=O)C(O)=C1 UILPJVPSNHJFIK-UHFFFAOYSA-N 0.000 abstract 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 2
- 239000003513 alkali Substances 0.000 abstract 2
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 abstract 2
- 150000002213 flavones Chemical class 0.000 abstract 2
- 235000013305 food Nutrition 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 238000010348 incorporation Methods 0.000 abstract 2
- 230000001590 oxidative effect Effects 0.000 abstract 2
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 abstract 2
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 abstract 1
- 239000001149 (9Z,12Z)-octadeca-9,12-dienoate Substances 0.000 abstract 1
- WTTJVINHCBCLGX-UHFFFAOYSA-N (9trans,12cis)-methyl linoleate Natural products CCCCCC=CCC=CCCCCCCCC(=O)OC WTTJVINHCBCLGX-UHFFFAOYSA-N 0.000 abstract 1
- BCEPNLMYVYJIHU-UHFFFAOYSA-N 1-(2-hydroxy-3,4-dimethoxyphenyl)ethanone Chemical compound COC1=CC=C(C(C)=O)C(O)=C1OC BCEPNLMYVYJIHU-UHFFFAOYSA-N 0.000 abstract 1
- HNTGIJLWHDPAFN-UHFFFAOYSA-N 1-bromohexadecane Chemical compound CCCCCCCCCCCCCCCCBr HNTGIJLWHDPAFN-UHFFFAOYSA-N 0.000 abstract 1
- MIINHRNQLVVCEW-UHFFFAOYSA-N 132-16-1 Chemical compound [Fe+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 MIINHRNQLVVCEW-UHFFFAOYSA-N 0.000 abstract 1
- QAWXSXIDGKPHQF-UHFFFAOYSA-N 2,3,4-trihydroxy-1-phenyloctadecan-1-one Chemical compound OC(C(=O)C1=CC=CC=C1)C(C(CCCCCCCCCCCCCC)O)O QAWXSXIDGKPHQF-UHFFFAOYSA-N 0.000 abstract 1
- MPNYEOHUDBSABW-UHFFFAOYSA-N 2,5-bis(phenylmethoxy)benzaldehyde Chemical compound C=1C=C(OCC=2C=CC=CC=2)C(C=O)=CC=1OCC1=CC=CC=C1 MPNYEOHUDBSABW-UHFFFAOYSA-N 0.000 abstract 1
- CLFRCXCBWIQVRN-UHFFFAOYSA-N 2,5-dihydroxybenzaldehyde Chemical compound OC1=CC=C(O)C(C=O)=C1 CLFRCXCBWIQVRN-UHFFFAOYSA-N 0.000 abstract 1
- QIQZAISWDRNIFG-UHFFFAOYSA-N 2-hydroxy-5-phenylmethoxybenzaldehyde Chemical compound C1=C(C=O)C(O)=CC=C1OCC1=CC=CC=C1 QIQZAISWDRNIFG-UHFFFAOYSA-N 0.000 abstract 1
- KOEXDWWDLABQCN-UHFFFAOYSA-N 3,4-dibenzyl-2,5-dihydroxybenzaldehyde Chemical compound C(C1=CC=CC=C1)C=1C(=C(C(C=O)=CC1O)O)CC1=CC=CC=C1 KOEXDWWDLABQCN-UHFFFAOYSA-N 0.000 abstract 1
- LNJCGNRKWOHFFV-UHFFFAOYSA-N 3-(2-hydroxyethylsulfanyl)propanenitrile Chemical compound OCCSCCC#N LNJCGNRKWOHFFV-UHFFFAOYSA-N 0.000 abstract 1
- HIJMTZFDBPBKHN-UHFFFAOYSA-N 3-hydroxy-7-methoxy-2-phenyl-5-phenylmethoxychromen-4-one Chemical compound C(C1=CC=CC=C1)OC1=C2C(C(=C(OC2=CC(=C1)OC)C1=CC=CC=C1)O)=O HIJMTZFDBPBKHN-UHFFFAOYSA-N 0.000 abstract 1
- HFTOVESXIIKQFL-UHFFFAOYSA-N 4,5,6-trihydroxy-1-phenylicosan-1-one Chemical compound OC(CCC(=O)C1=CC=CC=C1)C(C(CCCCCCCCCCCCCC)O)O HFTOVESXIIKQFL-UHFFFAOYSA-N 0.000 abstract 1
- -1 5 - n - hexyl Chemical group 0.000 abstract 1
- KJRQQECDVUXBCO-UHFFFAOYSA-N 7,8-dimethoxyflavone Chemical compound COC=1C(OC)=CC=C(C(C=2)=O)C=1OC=2C1=CC=CC=C1 KJRQQECDVUXBCO-UHFFFAOYSA-N 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- PKIXXJPMNDDDOS-UHFFFAOYSA-N Methyl linoleate Natural products CCCCC=CCCC=CCCCCCCCC(=O)OC PKIXXJPMNDDDOS-UHFFFAOYSA-N 0.000 abstract 1
- 235000021355 Stearic acid Nutrition 0.000 abstract 1
- 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
- WJGAPUXHSQQWQF-UHFFFAOYSA-N acetic acid;hydrochloride Chemical compound Cl.CC(O)=O WJGAPUXHSQQWQF-UHFFFAOYSA-N 0.000 abstract 1
- 238000006640 acetylation reaction Methods 0.000 abstract 1
- 230000001476 alcoholic effect Effects 0.000 abstract 1
- 150000005215 alkyl ethers Chemical class 0.000 abstract 1
- 230000003078 antioxidant effect Effects 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- AMFIJXSMYBKJQV-UHFFFAOYSA-L cobalt(2+);octadecanoate Chemical compound [Co+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O AMFIJXSMYBKJQV-UHFFFAOYSA-L 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000010411 cooking Methods 0.000 abstract 1
- 230000017858 demethylation Effects 0.000 abstract 1
- 238000010520 demethylation reaction Methods 0.000 abstract 1
- 239000000839 emulsion Substances 0.000 abstract 1
- 239000003925 fat Substances 0.000 abstract 1
- 235000019197 fats Nutrition 0.000 abstract 1
- 239000010685 fatty oil Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- 150000002632 lipids Chemical class 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 230000011987 methylation Effects 0.000 abstract 1
- 238000007069 methylation reaction Methods 0.000 abstract 1
- VYQNWZOUAUKGHI-UHFFFAOYSA-N monobenzone Chemical compound C1=CC(O)=CC=C1OCC1=CC=CC=C1 VYQNWZOUAUKGHI-UHFFFAOYSA-N 0.000 abstract 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 abstract 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 abstract 1
- KLAKIAVEMQMVBT-UHFFFAOYSA-N p-hydroxy-phenacyl alcohol Natural products OCC(=O)C1=CC=C(O)C=C1 KLAKIAVEMQMVBT-UHFFFAOYSA-N 0.000 abstract 1
- 229940079877 pyrogallol Drugs 0.000 abstract 1
- 239000008117 stearic acid Substances 0.000 abstract 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 abstract 1
- VHBFFQKBGNRLFZ-UHFFFAOYSA-N vitamin p Natural products O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- 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
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B5/00—Preserving by using additives, e.g. anti-oxidants
- C11B5/0021—Preserving by using additives, e.g. anti-oxidants containing oxygen
- C11B5/0035—Phenols; Their halogenated and aminated derivates, their salts, their esters with carboxylic acids
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Pyrane Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises (a) 7-alkyl ether derivatives of 3:7:21:51-tetrahydroxyflavone, which may be substituted at one or more of the 5-, 6-, 8-, 31-, 41- and 61- positions by alkyl groups and which have alkoxy or aralkoxy groups in place of the hydroxy groups in the 21- and 51- positions; (b) 3:7:21:51-tetra hydroxyflavone derivatives substituted at the 5-, 6-, 8-, 31-, 41-, and 61- positions by one o more alkyl groups; and (c) 3:7:8:21:51-pentahydroxyflavone and 7- and/or 8- and/or 21-and/or 51-alkyl ether derivatives thereof which may be substituted at the 5-, 6-, 31-, 41-, and 61- positions by one or more alkyl groups, together with their preparation by oxidising a chalkone of the general formula:- <FORM:0875164/IV (b)/1> <FORM:0875164/IV (b)/2> wherein X and/or X1 are protecting groups (e.g. benzyl, isopropyl or methyl) which can subsequently be removed or are hydrogen atoms, R is alkoxy and R1 is hydrogen, alkyl, or alkoxy, and any unoccupied position in either ring may be substituted by alkyl, and thereafter if necessary removing the protecting groups and/or converting R and R1 into hydroxy groups. The oxidation is preferably carried out with alcoholic potassium hydroxide and hydrogen peroxide, and the protecting groups may be removed by treatment with HCl or HBr and acetic acid or HI and phenol. In Examples:- (1) gentisaldehyde is benzylated and the dibenzyl ether condensed with 2-hydroxy-4-methoxyacetophenone in aqueous ethanolic alkali giving 2,5-bis(benzyloxy)-21-hydroxy-41-methoxy chalkone, which is oxidised with H2O2 in alcoholi KOH to 21,51-bis (benzyloxy)-3 - hydroxy - 7 - methoxy flavone, characterized as its acetate, and debenzylated with HCl-acetic acid to 3,21,51-trihydroxy-7-methoxyflavone; (2) 2,5-bis(benzyloxy)-41-n-butoxy-2-hydroxychalkone prepared as in (1) is oxidised and debenzylated to 7-n-butoxy-3,21,51-trihydroxyflavone, characterized as its 7,8-dimethoxyflavone is refluxed with aqueous HBr giving 3,7,8,21,51-pentahydroxyflavone; (4) paenol is condensed with 2-hydroxy-5-methoxybenzaldehyde and the resulting chalkone oxidised to 3,21-dihydroxy-7,51-dimethoxyflavone; (5) resacetophenone is monoetherified with cetyl bromide and condensed with 2,5-dibenzyloxybenzaldehyde, the chalkone oxidised with H2O2 and debenzylated to 7-cetyloxy-3,2151-trihydroxyflavone, characterized as its triacetate; (6) 5 - ethyl - 2,4 - dihydroxyacetophenone is monomethylated and then treated as in (4) giving 3,21-dihydroxy-7,51-dimethoxy-6-ethylflavone and its diacetate; (7) demethylation yields 6-ethyl-3,7,21,51-tetrahydroxyflavone; (8) and (9), 3,4-dimethoxy-5-ethyl-2-hydroxyacetophenone and 5 - n - hexyl - 2 - hydroxy-4-methoxyacetophenone similarly give 6-ethyl-3,7,8,21,51-pentahydroxyflavone and 6-n-hexyl-3,7,21,51-tetrahydroxyflavone respectively; (10) O-benzylhydroquinone is treated with chloroform and alkali giving 5-benzyloxy-2-hydroxybenzaldehyde, which is methylated and condensed with 2-hydroxy-3,4-dimethoxy-5-stearylacetophenone (prepared from pyrogallol by treatment with stearic acid and BF3, reduction of the resulting 2,3,4-trihydroxystearophenone, C-acetylation with BF3 of the 4-stearylpyrogallol and methylation of the 2,3,4-trihydroxystearylacetophenone) giving a chalkone which on oxidation yields 3,51-dihydroxy-7,8,21-trimethoxy-6-stearylflavone and is then demethylated with HI in phenol; (11) 3,7,21,51-tetrahydroxy-6-stearyl flavone is similarly obtained; (12) 2-hydroxy-3,4-dimethoxyacetophenone and dibenzylgentisaldehyde as in (1) yield 3,21,51-trihydroxy-7,8-dimethoxyflavone.ALSO:Fatty oils, fats and other liquids subject to oxidative rancidity are protected against oxidation by the incorporation therein of a small proportion of one or more hydroxy flavones selected from the following:-(a) 7-alkyl ethers of 3:7:21:51-tetrahydroxyflavone, which may be substituted at one or more of the 5-, 6-, 8, 31, 41, and 61- positions by alky groups and which may have alkoxy or aralkoxy groups in place of the hydroxy groups in the 21- and 51- positions; (b) 3:7:21:51-tetrahydroxyflavone derivatives substituted at the 5-, 6-, 8-, 31, 41, and 61- positions by one or more alkyl groups; (c) 3:7:8:21:51-pentahydroxyflavone and 7- and/or 8- and/or 21-and/or 51- alkyl ether derivatives thereof which may be substituted at the 5-, 6-, 31-, 41-, and 61- positions by one or more alkyl groups. A table gives the anti-oxidant efficiencies of twenty-two flavones (including known compounds) in linoleic acid, methyl linoleate, their aqueous emulsions and benzene solutions using cobaltous stearate and ferrous phthalocyanine as catalysts.ALSO:Lipid-containing foods and feeds are protected against oxidative rancidity by the incorporation of a small proportion of one or more of the hydroxyflavones: (a) 7-alkyl ethers of 3 : 7 : 21 : 51 - tetrahydroxyflavone, which may be alkyl substituted at positions 5, 6, 8, 31, 41 or 61, and which may have alkoxy or aralkoxy groups in place of hydroxy groups at 21 and 51 positions; (b) 3 : 7 : 21 : 51 - tetrahydroxyflavones substituted at the 5, 6, 8, 31, 41 or 61 positions by one or more alkyl groups; (c) 3 : 7 : 8 : 21 : 51 - pentahydroxyflavone and its 7 and/or 8 and/or 21 and/or 51 alkyl ether derivatives, which may be substituted at 5, 6, 31, 41 or 61 positions by one or more alkyl groups. The flavones may be incorporated during cooking in food manufacture.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB24031/56A GB875164A (en) | 1956-08-03 | 1956-08-03 | New hydroxyflavones, their production and use as anti-oxidants |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB24031/56A GB875164A (en) | 1956-08-03 | 1956-08-03 | New hydroxyflavones, their production and use as anti-oxidants |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB875164A true GB875164A (en) | 1961-08-16 |
Family
ID=10205285
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB24031/56A Expired GB875164A (en) | 1956-08-03 | 1956-08-03 | New hydroxyflavones, their production and use as anti-oxidants |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB875164A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003031430A3 (en) * | 2001-10-04 | 2004-04-08 | Brane Tech S R L | Flavonoid compounds and their pharmaceutical uses |
| CN111303105A (en) * | 2019-04-19 | 2020-06-19 | 武汉万知化工医药有限公司 | Preparation method of 7, 8-dihydroxyflavone |
| CN114052247A (en) * | 2020-08-06 | 2022-02-18 | 晨光生物科技集团股份有限公司 | An antioxidant composition containing quercetagetin, 6-hydroxy kaempferol and gallic acid |
| CN117534680A (en) * | 2023-11-07 | 2024-02-09 | 广西中医药大学 | Chromone derivative, and preparation method and application thereof |
-
1956
- 1956-08-03 GB GB24031/56A patent/GB875164A/en not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003031430A3 (en) * | 2001-10-04 | 2004-04-08 | Brane Tech S R L | Flavonoid compounds and their pharmaceutical uses |
| CN111303105A (en) * | 2019-04-19 | 2020-06-19 | 武汉万知化工医药有限公司 | Preparation method of 7, 8-dihydroxyflavone |
| CN114052247A (en) * | 2020-08-06 | 2022-02-18 | 晨光生物科技集团股份有限公司 | An antioxidant composition containing quercetagetin, 6-hydroxy kaempferol and gallic acid |
| CN114052247B (en) * | 2020-08-06 | 2023-06-16 | 晨光生物科技集团股份有限公司 | An antioxidant composition containing quercetin, 6-hydroxy kaempferol and gallic acid |
| CN117534680A (en) * | 2023-11-07 | 2024-02-09 | 广西中医药大学 | Chromone derivative, and preparation method and application thereof |
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