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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
—— 8-bromo-7-n-butoxy-6-nitroflavonol 135878-89-6 C19H16BrNO6
8-bromo-7-n-butoxy-6-nitroflavonol
—— 5,7-hydroxy-8-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-2-(4-methylphenyl)-4H-chromen-4-one 1128053-57-5 C22H21NO4
5,7-hydroxy-8-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-2-(4-methylphenyl)-4H-chromen-4-one
—— 4-Oxo-2-phenyl-chroman-7-ol anion 144383-24-4 C15H11O3
4-Oxo-2-phenyl-chroman-7-ol anion
—— 3-hydroxy-5-[2-(3,4,5-trimethoxy-phenyl)-furo[3,2-b]pyridin-7-yl]-benzoic acid methyl ester 1360909-12-1 C24H21NO7
3-hydroxy-5-[2-(3,4,5-trimethoxy-phenyl)-furo[3,2-b]pyridin-7-yl]-benzoic acid methyl ester
—— 7,7''-Biflavonyloxymethan 24532-00-1 C31H20O6
7,7''-Biflavonyloxymethan
—— 2-(2,5-dimethylphenyl)chroman-4-one 1428926-07-1 C17H16O2
2-(2,5-dimethylphenyl)chroman-4-one
—— (2S,3R)-trans-3',4'-methylenedioxyflavan-3-ol 1196870-37-7 C16H14O4
(2S,3R)-trans-3',4'-methylenedioxyflavan-3-ol
—— epicatechin-(4β->8,2β->O->7)-epicatechin-(4β->8)-dryopterin 135308-93-9 C47H36O19
epicatechin-(4β->8,2β->O->7)-epicatechin-(4β->8)-dryopterin
—— 1362479-34-2 C18H15NO
—— 9-methyl-5-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-11,12-dihydro-5H-6,13-dioxa-benzo[3,4]cyclohepta[1,2-a]naphthalen-2-ol 554431-54-8 C31H33NO4
9-methyl-5-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-11,12-dihydro-5H-6,13-dioxa-benzo[3,4]cyclohepta[1,2-a]naphthalen-2-ol
—— 2-(3-Methoxy-4-oxo-2-p-tolyl-4H-chromen-6-yl)-propionic acid methyl ester 141070-55-5 C21H20O5
2-(3-Methoxy-4-oxo-2-p-tolyl-4H-chromen-6-yl)-propionic acid methyl ester
—— 6-(2,3,4,5,6-Pentamethylphenyl)-2,2-diphenylchromene 1322004-72-7 C32H30O
6-(2,3,4,5,6-Pentamethylphenyl)-2,2-diphenylchromene
—— 7a-(4-Trifluoromethyl-phenyl)-1a,7a-dihydro-1H-7-oxa-cyclopropa[b]naphthalen-2-one 128814-97-1 C17H11F3O2
7a-(4-Trifluoromethyl-phenyl)-1a,7a-dihydro-1H-7-oxa-cyclopropa[b]naphthalen-2-one
—— 2-(2-chlorophenyl)-8-(3-ethylmethylamino-2-hydroxypropyl)-5,7-dimethoxy-4H-1-benzopyran-4-one 952678-04-5 C23H26ClNO5
2-(2-chlorophenyl)-8-(3-ethylmethylamino-2-hydroxypropyl)-5,7-dimethoxy-4H-1-benzopyran-4-one
—— 7,8-Dimethoxy-2-phenyl-3,4-dihydro-2H-benzo[b]oxepin-5-one 128814-99-3 C18H18O4
7,8-Dimethoxy-2-phenyl-3,4-dihydro-2H-benzo[b]oxepin-5-one
—— 62596-39-8 C27H24O7
—— 2-(2-allyloxy-phenyl)-4-oxo-4<i>H</i>-chromene-6-carboxylic acid 66848-76-8 C19H14O5
2-(2-allyloxy-phenyl)-4-oxo-4<i>H</i>-chromene-6-carboxylic acid
—— Acetic acid 8-(4,7-diacetoxy-2-isopropylidene-2,3-dihydro-benzofuran-5-yl)-2,2-dimethyl-6-oxo-2H,6H-pyrano[3,2-g]chromen-5-yl ester 64379-39-1 C31H28O10
Acetic acid 8-(4,7-diacetoxy-2-isopropylidene-2,3-dihydro-benzofuran-5-yl)-2,2-dimethyl-6-oxo-2H,6H-pyrano[3,2-g]chromen-5-yl ester
—— (E)-1-{4-[(2S,3R,4S,5R,6R)-4,5-Dihydroxy-6-hydroxymethyl-3-((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-2-hydroxy-phenyl}-3-(4-hydroxy-phenyl)-propenone 67322-12-7 C27H32O13
(E)-1-{4-[(2S,3R,4S,5R,6R)-4,5-Dihydroxy-6-hydroxymethyl-3-((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-2-hydroxy-phenyl}-3-(4-hydroxy-phenyl)-propenone
—— 8-Methoxy-13,13-bis(4-methoxyphenyl)-1',1',5',5'-tetramethylspiro[6,12-dioxahexacyclo[15.7.0.02,10.03,7.011,16.019,24]tetracosa-1(17),2,7,9,11(16),14,19,21,23-nonaene-18,3'-cyclohexane] 1259400-45-7 C46H46O5
8-Methoxy-13,13-bis(4-methoxyphenyl)-1',1',5',5'-tetramethylspiro[6,12-dioxahexacyclo[15.7.0.02,10.03,7.011,16.019,24]tetracosa-1(17),2,7,9,11(16),14,19,21,23-nonaene-18,3'-cyclohexane]
—— 4'-Ethoxy-4-deuteroxyflavan 72594-31-1 C17H18O3
4'-Ethoxy-4-deuteroxyflavan
—— 3,6,8-tribromo-2-phenyl-2,3-dihydrochromen-4-one 102260-65-1 C15H9Br3O2
3,6,8-tribromo-2-phenyl-2,3-dihydrochromen-4-one
—— 8-Bromo-7-butoxy-2-(4-hydroxy-3-methoxy-phenyl)-6-nitro-chromen-4-one 135878-88-5 C20H18BrNO7
8-Bromo-7-butoxy-2-(4-hydroxy-3-methoxy-phenyl)-6-nitro-chromen-4-one
—— 1175534-08-3 C19H16ClNO9
—— 3-Benzyloxy-6-butyryl-2-(4-chloro-phenyl)-chromen-4-one 173469-82-4 C26H21ClO4
3-Benzyloxy-6-butyryl-2-(4-chloro-phenyl)-chromen-4-one
—— 2',3',4',5,5',6,7,8-octamethoxyflavanone 96344-55-7 C23H28O10
2',3',4',5,5',6,7,8-octamethoxyflavanone
—— 2-(2-Chlorophenyl)-6-(6-(4-hydroxypiperidinyl)hexoxy)-4H-1-benzopyran-4-one hydrochloride 139652-92-9 C26H30ClNO4*ClH
2-(2-Chlorophenyl)-6-(6-(4-hydroxypiperidinyl)hexoxy)-4H-1-benzopyran-4-one hydrochloride
—— (E)-3-[(dipropylamino)methylene]-2-phenylchroman-4-one 1268460-01-0 C22H25NO2
(E)-3-[(dipropylamino)methylene]-2-phenylchroman-4-one
—— 7-(2-chloro-acetylamino)-3-methyl-2-phenyl-chromen-4-one 56822-75-4 C18H14ClNO3
7-(2-chloro-acetylamino)-3-methyl-2-phenyl-chromen-4-one
—— 6,8-Dibrom-5-hydroxy-7,4'-diacetoxy-flavon 3162-17-2 C20H14Br2O8
6,8-Dibrom-5-hydroxy-7,4'-diacetoxy-flavon
—— 5,7,8-triacetoxy-3-methoxy-2-phenyl-chromen-4-one 33803-39-3 C22H18O9
5,7,8-triacetoxy-3-methoxy-2-phenyl-chromen-4-one
—— rac-(2R,3S)-5-methyl-3-phenyl-3H-spiro[benzofuran-2,1'-cyclohexan]-2'-en-3-ol 141883-80-9 C20H20O2
rac-(2R,3S)-5-methyl-3-phenyl-3H-spiro[benzofuran-2,1'-cyclohexan]-2'-en-3-ol
—— (Z)-2-[2-(4-Methoxy-phenyl)-3-nitro-chroman-4-yl]-3-methylamino-but-2-enoic acid methyl ester 133765-30-7 C22H24N2O6
(Z)-2-[2-(4-Methoxy-phenyl)-3-nitro-chroman-4-yl]-3-methylamino-but-2-enoic acid methyl ester
—— 7-{(diisopropylphosphoryl)-methyloxy}-3',4',5-trimethoxyflavone 1092093-75-8 C25H31O9P
7-{(diisopropylphosphoryl)-methyloxy}-3',4',5-trimethoxyflavone
—— 5'-Chloro-3,5,7,2'-tetramethoxyflavone 95055-82-6 C19H17ClO6
5'-Chloro-3,5,7,2'-tetramethoxyflavone
—— 6,8-di-C-(β-D-xylopyranosyl)-5,7,3',4'-tetrahydroxyflavone 1253227-41-6 C25H26O14
6,8-di-C-(β-D-xylopyranosyl)-5,7,3',4'-tetrahydroxyflavone
—— 4-ethoxy-2-(2-methylphenyl)-2H-chromene 81635-41-8 C18H18O2
4-ethoxy-2-(2-methylphenyl)-2H-chromene
—— 2-(4-hydroxy-phenyl)-6,6,10,10-tetramethyl-2,3,7,8,11,12-hexahydro-6<i>H</i>,10<i>H</i>-dipyrano[2,3-<i>f</i>;2',3'-<i>h</i>]chromen-4-one 68634-17-3 C25H28O5
2-(4-hydroxy-phenyl)-6,6,10,10-tetramethyl-2,3,7,8,11,12-hexahydro-6<i>H</i>,10<i>H</i>-dipyrano[2,3-<i>f</i>;2',3'-<i>h</i>]chromen-4-one
—— 7-butyloxy-5-hydroxyflavothione 1203579-89-8 C19H18O3S
7-butyloxy-5-hydroxyflavothione
—— 1206902-70-6 C17H13F3O6S
—— 2-(2-hydroxy-phenyl)-7,8-dimethoxy-chroman-4-one 109248-41-1 C17H16O5
2-(2-hydroxy-phenyl)-7,8-dimethoxy-chroman-4-one
—— 8-Brom-5-hydroxy-7,4'-diacetoxy-flavon 3486-97-3 C19H13BrO7
8-Brom-5-hydroxy-7,4'-diacetoxy-flavon
—— 3-acetoxy-7-acetylamino-2-(4-acetylamino-phenyl)-chromen-4-one 102311-87-5 C21H18N2O6
3-acetoxy-7-acetylamino-2-(4-acetylamino-phenyl)-chromen-4-one
—— 1416325-78-4 C61H59NO4S
—— 3-(4-Methylphenyl)-3-phenylbenzo[f]chromene 194712-95-3 C26H20O
3-(4-Methylphenyl)-3-phenylbenzo[f]chromene
—— (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(3,5-dihydroxy-4-(3-(4-hydroxyphenyl)propanoyl)phenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 1133352-99-4 C29H32O14
(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(3,5-dihydroxy-4-(3-(4-hydroxyphenyl)propanoyl)phenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate
—— 2',5,7-trimethyldatiscetin 33874-85-0 C18H16O6
2',5,7-trimethyldatiscetin
—— 5,5-Difluoro-8-methoxy-13,13-bis(4-methoxyphenyl)-1',1',5',5'-tetramethylspiro[6,12-dioxahexacyclo[15.7.0.02,10.03,7.011,16.019,24]tetracosa-1(17),2,7,9,11(16),14,19,21,23-nonaene-18,3'-cyclohexane] 1259401-16-5 C46H44F2O5
5,5-Difluoro-8-methoxy-13,13-bis(4-methoxyphenyl)-1',1',5',5'-tetramethylspiro[6,12-dioxahexacyclo[15.7.0.02,10.03,7.011,16.019,24]tetracosa-1(17),2,7,9,11(16),14,19,21,23-nonaene-18,3'-cyclohexane]
—— 3',4'-diacetyloxy-3,5,6,7-tetramethoxyflavone 124458-92-0 C23H22O10
3',4'-diacetyloxy-3,5,6,7-tetramethoxyflavone
—— 3-(4-oxo-2-phenyl-4<i>H</i>-chromen-6-yl)-propionic acid 66849-06-7 C18H14O4
3-(4-oxo-2-phenyl-4<i>H</i>-chromen-6-yl)-propionic acid