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黄酮类化合物

黄酮类化合物 定义与结构特征

黄酮类化合物是一大类天然存在的有机化合物,属于酚类衍生物。它们的分子结构通常包含两个苯环(A和B环)和一个三碳环(C环),形成一个基本骨架。该骨架由多个亚结构组成,包括黄烷醇、黄酮、黄酮醇等。

生物来源

黄酮类化合物广泛存在于植物界中,常见于许多蔬菜、水果及中药中。例如,在大豆、柑橘、茶叶和甘草中都可以找到它们的身影。

化学性质 亲水性与溶解度

由于其分子结构中含有多个酚羟基,因此具有一定的亲水性和良好的溶解性,这使得黄酮类化合物在药物设计中扮演重要角色。

稳定性与光敏性

大多数黄酮类化合物相对稳定,在适宜条件下不易发生降解。但某些类型的黄酮对光照比较敏感,容易被氧化,导致颜色变化。

生理活性与药用价值

黄酮类化合物因其丰富的生理活性而备受关注,主要包括:

  • 抗氧化作用:可有效清除体内自由基,保护细胞免受损伤。
  • 抗炎效应:有助于减轻炎症反应,缓解症状。
  • 心血管保护:可能通过多种机制改善心脑血管健康。
  • 抗癌潜力:研究表明某些黄酮类物质具有抑制肿瘤生长的能力。
应用领域 食品工业

作为一种天然色素和抗氧化剂,被广泛应用于食品加工中以提高其保质期及营养价值。

化妆品行业

利用其良好的生物相容性和抗衰老特性,在化妆品配方中应用广泛。

药物开发

由于黄酮类化合物展现出广泛的药理活性,已成为新药研发的重要候选目标之一。

中文名称 英文名称 CAS号 化学式 结构式图片
—— dihydrokaemferol 3-O-α-L-rhamnoside-5-O-β-D-glucoside 135545-93-6 C27H32O15
dihydrokaemferol 3-O-α-L-rhamnoside-5-O-β-D-glucoside
—— 2-[6-(2-(3-hydroxyphenyl)chroman-6-yloxy)pyridin-3-ylcarbamoyl]-(S)-pyrrolidine-1-carboxylic acid tert-butyl ester 728936-02-5 C30H33N3O6
2-[6-(2-(3-hydroxyphenyl)chroman-6-yloxy)pyridin-3-ylcarbamoyl]-(S)-pyrrolidine-1-carboxylic acid tert-butyl ester
—— 1333408-76-6 C26H17Cl2FO4
—— 1333408-73-3 C27H21FO4
—— 6,8-Dibrom-7-hydroxy-flavon 10445-94-0 C15H8Br2O3
6,8-Dibrom-7-hydroxy-flavon
—— 2,3-dimethoxy-2-(4-methoxy-phenyl)-chroman-4-one 854244-59-0 C18H18O5
2,3-dimethoxy-2-(4-methoxy-phenyl)-chroman-4-one
—— 3-hydroxy-2-(3-hydroxy-phenyl)-4-oxo-4<i>H</i>-chromene-6-carboxylic acid 58539-89-2 C16H10O6
3-hydroxy-2-(3-hydroxy-phenyl)-4-oxo-4<i>H</i>-chromene-6-carboxylic acid
—— (7S,8R,9R)-7-hydroxy-2,3-dimethyl-9-phenyl-7-vinyl-8,9-dihydro-7H-imidazo[1,2-a]pyrano[2,3-c]pyridin-8-yl pivalate 1027002-83-0 C25H28N2O4
(7S,8R,9R)-7-hydroxy-2,3-dimethyl-9-phenyl-7-vinyl-8,9-dihydro-7H-imidazo[1,2-a]pyrano[2,3-c]pyridin-8-yl pivalate
—— 6-acetyl-5,7-dihydroxy-3',4'-dimethoxyflavone 848734-07-6 C19H16O7
6-acetyl-5,7-dihydroxy-3',4'-dimethoxyflavone
—— (+)-(2R,3S)-5,7-bis(benzyloxy)-2-[3',5'-bis(benzyloxy)-4'-methoxyphenyl]chroman-3-ol 901125-38-0 C44H40O7
(+)-(2R,3S)-5,7-bis(benzyloxy)-2-[3',5'-bis(benzyloxy)-4'-methoxyphenyl]chroman-3-ol
—— 7-<(2-Hydroxy-propyl)-carbamoylmethoxy>-4-oxo-2-phenyl-4H-chromen 89169-05-1 C20H19NO5
7-<(2-Hydroxy-propyl)-carbamoylmethoxy>-4-oxo-2-phenyl-4H-chromen
—— 2-[6-(2-phenylchroman-6-yloxy)pyridin-3-ylcarbamoyl]-(S)-pyrrolidine-1-carboxylic acid tert-butyl ester 728935-77-1 C30H33N3O5
2-[6-(2-phenylchroman-6-yloxy)pyridin-3-ylcarbamoyl]-(S)-pyrrolidine-1-carboxylic acid tert-butyl ester
—— 7-{2-[1-(4-methylpiperazin-1-yl)-2-oxopropylidene]hydrazinyl}-2-phenyl-4H-chromen-4-one 1394154-22-3 C23H24N4O3
7-{2-[1-(4-methylpiperazin-1-yl)-2-oxopropylidene]hydrazinyl}-2-phenyl-4H-chromen-4-one
—— 2-(4-Chloro-phenyl)-6-methoxy-3-nitro-chromen-4-one 143468-25-1 C16H10ClNO5
2-(4-Chloro-phenyl)-6-methoxy-3-nitro-chromen-4-one
—— 5,7-dibenzyloxy-2-(2,2-diphenylbenzo[d][1,3]dioxol-5-yl)-3-β-D-[2'',3''-di-O-(4-propylbenzoyl)-4'',6''-O-isopropylidene]glucosyl-4H-chromen-4-one 1246840-50-5 C71H64O14
5,7-dibenzyloxy-2-(2,2-diphenylbenzo[d][1,3]dioxol-5-yl)-3-β-D-[2'',3''-di-O-(4-propylbenzoyl)-4'',6''-O-isopropylidene]glucosyl-4H-chromen-4-one
—— 6-acetyl-5,7-dihydroxy-4'-nitroflavone 848734-10-1 C17H11NO7
6-acetyl-5,7-dihydroxy-4'-nitroflavone
—— (2<i>R</i>)-2<i>r</i>-(3,4-Dimethoxy-phenyl)-3<i>c</i>,5,7-trimethoxy-chroman 120786-78-9 C20H24O6
(2<i>R</i>)-2<i>r</i>-(3,4-Dimethoxy-phenyl)-3<i>c</i>,5,7-trimethoxy-chroman
—— 2-(4-benzyloxy-3-methoxy-phenyl)-3-hydroxy-7-methyl-chroman-4-one 115293-43-1 C24H22O5
2-(4-benzyloxy-3-methoxy-phenyl)-3-hydroxy-7-methyl-chroman-4-one
—— 2'-[4-O-(α-D-glucopyranosyl)-β-D-glucopyranosyloxy]-6'-hydroxy-3-(5-benzo[b]furanyl)propiophenone 174456-47-4 C29H34O14
2'-[4-O-(α-D-glucopyranosyl)-β-D-glucopyranosyloxy]-6'-hydroxy-3-(5-benzo[b]furanyl)propiophenone
—— 2-(2'-chlorophenyl)-6-bromo-8-methyl-3-bromoflavone 106551-55-7 C16H9Br2ClO2
2-(2'-chlorophenyl)-6-bromo-8-methyl-3-bromoflavone
—— 2-(3-Chloro-phenyl)-3-dimethylaminomethyl-chroman-4-one; hydrochloride 77038-08-5 C18H18ClNO2*ClH
2-(3-Chloro-phenyl)-3-dimethylaminomethyl-chroman-4-one; hydrochloride
—— 1400900-18-6 C32H28ClNO4S
—— Procyanidin-octamethylaether 122741-80-4 C38H42O13
Procyanidin-octamethylaether
—— 7-carboxymethyloxy-3',4',5-trimethoxy flavone ethanolate 847909-47-1 C2H6O*C20H18O8
7-carboxymethyloxy-3',4',5-trimethoxy flavone ethanolate
—— 7-carboxymethyloxy-5-cyclopentyloxy-3',4'-dimethoxy flavone 203191-33-7 C24H24O8
7-carboxymethyloxy-5-cyclopentyloxy-3',4'-dimethoxy flavone
—— (2R,4R:2R,3S)-5,7,3'4'-tetra-O-methylflavan-3-one-4α->8-5,7,3',4'-tetra-O-methylflavan-3-ol 1052075-27-0 C38H40O12
(2R,4R:2R,3S)-5,7,3'4'-tetra-O-methylflavan-3-one-4α->8-5,7,3',4'-tetra-O-methylflavan-3-ol
—— 2-benzo[1,3]dioxol-5-yl-8-(2-bromo-propyl)-7-hydroxy-3-methoxy-chromen-4-one 111270-96-3 C20H17BrO6
2-benzo[1,3]dioxol-5-yl-8-(2-bromo-propyl)-7-hydroxy-3-methoxy-chromen-4-one
—— 3,7,3',4',2'',3'',4'',6''-octa-O-acetyl-(+)-catechin 5-O-β-D-glucoside 1209469-10-2 C37H40O19
3,7,3',4',2'',3'',4'',6''-octa-O-acetyl-(+)-catechin 5-O-β-D-glucoside
—— (2R,3S)-6-tert-Butyl-3-iodo-2-phenyl-chroman 76336-85-1 C19H21IO
(2R,3S)-6-tert-Butyl-3-iodo-2-phenyl-chroman
—— (2E)-1-(4-O-β-D-glucopyranosyl-3-methoxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one 1252793-94-4 C22H24O9
(2E)-1-(4-O-β-D-glucopyranosyl-3-methoxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one
—— 5-acetoxy-2,3-dihydro-7-dimethoxy-2-(4-methoxyphenyl)-6,8-dimethyl-4H-1-benzopyran-4-one 1352409-55-2 C21H22O6
5-acetoxy-2,3-dihydro-7-dimethoxy-2-(4-methoxyphenyl)-6,8-dimethyl-4H-1-benzopyran-4-one
—— 2-(6-{2-[3-(5-nitropyridin-2-yloxy)phenyl]chroman-6-yloxy}pyridin-3-ylcarbamoyl)-(S)-pyrrolidine-1-carboxylic acid tert-butyl ester 728936-04-7 C35H35N5O8
2-(6-{2-[3-(5-nitropyridin-2-yloxy)phenyl]chroman-6-yloxy}pyridin-3-ylcarbamoyl)-(S)-pyrrolidine-1-carboxylic acid tert-butyl ester
—— 6-[2-(3-(5-aminopyridin-2-yloxy)phenyl)chroman-6-yloxy]-pyridin-3-yl-amine 728937-07-3 C25H22N4O3
6-[2-(3-(5-aminopyridin-2-yloxy)phenyl)chroman-6-yloxy]-pyridin-3-yl-amine
—— 7-O-mesylapigenin 1104802-75-6 C16H12O7S
7-O-mesylapigenin
—— 8-bromo-4',5,7-trimethoxy-flavanone ethylene ketal 119529-69-0 C20H21BrO6
8-bromo-4',5,7-trimethoxy-flavanone ethylene ketal
—— (+)-Afzelechin 3-O-α-L-rhamnopyranoside 142741-31-9 C21H24O9
(+)-Afzelechin 3-O-α-L-rhamnopyranoside
—— 2-(7-hydroxy-3-methoxy-4-oxo-4H-chromen-2-yl)-benzoic acid 710338-40-2 C17H12O6
2-(7-hydroxy-3-methoxy-4-oxo-4H-chromen-2-yl)-benzoic acid
—— 7-carboxymethyloxy-5-hydroxy-6-n-butyloxy-3',4'-dimethoxy flavone 203191-24-6 C23H24O9
7-carboxymethyloxy-5-hydroxy-6-n-butyloxy-3',4'-dimethoxy flavone
—— 8-(benzylamino)-6-chloro-2-(3-methoxy-2-nitrophenyl)-4H-chromen-4-one 1621457-96-2 C23H17ClN2O5
8-(benzylamino)-6-chloro-2-(3-methoxy-2-nitrophenyl)-4H-chromen-4-one
—— 1-(4-Methoxy-benzoyl)-3-(4-oxo-2-phenyl-4H-chromen-6-yl)-thiourea 159679-98-8 C24H18N2O4S
1-(4-Methoxy-benzoyl)-3-(4-oxo-2-phenyl-4H-chromen-6-yl)-thiourea
—— (2R,3S)-2-(4-(benzyloxy)phenyl)chroman-3-ol 1196870-50-4 C22H20O3
(2R,3S)-2-(4-(benzyloxy)phenyl)chroman-3-ol
—— 7-<(3-Hydroxy-propyl)-carbamoylmethoxy>-4-oxo-2-phenyl-4H-chromen 89169-06-2 C20H19NO5
7-<(3-Hydroxy-propyl)-carbamoylmethoxy>-4-oxo-2-phenyl-4H-chromen
—— 5,7-Dimethoxy-6-(methoxymethyl)-2-(4-methoxyphenyl)-8-methylchromen-4-one 101395-15-7 C21H22O6
5,7-Dimethoxy-6-(methoxymethyl)-2-(4-methoxyphenyl)-8-methylchromen-4-one
—— 4-(butylimino)-7-chloro-2-(3,4-dichlorophenyl)-4H-chromen-5-ol 1262129-56-5 C19H16Cl3NO2
4-(butylimino)-7-chloro-2-(3,4-dichlorophenyl)-4H-chromen-5-ol
—— 2-(4-Chloro-phenyl)-8-methoxy-3-nitro-chromen-4-one 143468-27-3 C16H10ClNO5
2-(4-Chloro-phenyl)-8-methoxy-3-nitro-chromen-4-one
—— 2,5-dihydro-10-methoxy-5-(3-(2-(N,N-dimethylaminocarbonyloxy)ethyl)phenyl)-2,2,4-trimethyl-1H-[1]benzopyrano[3,4-f]quinoline 239069-79-5 C31H34N2O4
2,5-dihydro-10-methoxy-5-(3-(2-(N,N-dimethylaminocarbonyloxy)ethyl)phenyl)-2,2,4-trimethyl-1H-[1]benzopyrano[3,4-f]quinoline
—— 8-Allyl-5,7-dihydroxy-2-methyl-3-phenyl-chroman-4-one 111354-94-0 C19H18O4
8-Allyl-5,7-dihydroxy-2-methyl-3-phenyl-chroman-4-one
—— (2R,3S,4S)-2-(3,4-Dimethoxy-phenyl)-7-methoxy-4-(2,4,6-trimethoxy-phenyl)-chroman-3-ol 78174-75-1 C27H30O8
(2R,3S,4S)-2-(3,4-Dimethoxy-phenyl)-7-methoxy-4-(2,4,6-trimethoxy-phenyl)-chroman-3-ol
—— 2-(3,4-dimethoxy-phenyl)-3-hydroxy-5,7-dimethoxy-chromenylium; chloride 20931-30-0 C19H19O6*Cl
2-(3,4-dimethoxy-phenyl)-3-hydroxy-5,7-dimethoxy-chromenylium; chloride
—— 3-[6-(5-aminopyridin-2-yloxy)chroman-2-yl]phenol 728935-38-4 C20H18N2O3
3-[6-(5-aminopyridin-2-yloxy)chroman-2-yl]phenol