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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
—— 5,8-diacetoxy-7-benzyloxy-3-methoxy-2-phenyl-chromen-4-one 33803-34-8 C27H22O8
5,8-diacetoxy-7-benzyloxy-3-methoxy-2-phenyl-chromen-4-one
—— N',N'''-(((3H-benzo[f]chromene-3,3-diyl)bis(4,1-phenylene))bis(methaneylylidene))bis(4-methylbenzohydrazide) 1352172-06-5 C43H34N4O3
N',N'''-(((3H-benzo[f]chromene-3,3-diyl)bis(4,1-phenylene))bis(methaneylylidene))bis(4-methylbenzohydrazide)
—— 5,7-dimethoxyflavanone oxime 1193346-73-4 C17H17NO4
5,7-dimethoxyflavanone oxime
—— tri-tert-butyl ((2R,3S)-2-(2,4-difluoro-5-hydroxyphenyl)chromane-3,5,7-triyl) tricarbonate 1256550-74-9 C30H36F2O11
tri-tert-butyl ((2R,3S)-2-(2,4-difluoro-5-hydroxyphenyl)chromane-3,5,7-triyl) tricarbonate
—— 4-oxo-2-(4-fluorophenyl)-4H-1-benzopyran-8-acetic acid 127768-48-3 C17H11FO4
4-oxo-2-(4-fluorophenyl)-4H-1-benzopyran-8-acetic acid
—— cis 3-nitro-2-phenyl-3,4-dihydro-2H-<1>benzopyran 81289-22-7 C15H13NO3
cis 3-nitro-2-phenyl-3,4-dihydro-2H-<1>benzopyran
—— 5,7-di-O-(2-nitrobenzenesulfonyl)catechin 1203550-42-8 C27H20N2O14S2
5,7-di-O-(2-nitrobenzenesulfonyl)catechin
—— ((2R,3S,4S)-3,5,7-tris(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)-4-(2-ethoxyethoxy)chroman-8-yl)boronic acid 1352123-21-7 C54H53BO10
((2R,3S,4S)-3,5,7-tris(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)-4-(2-ethoxyethoxy)chroman-8-yl)boronic acid
—— 8-(3-amino-3-methylbutyl)-3,5,7-trihydroxy-2-(4-methoxyphenyl)-4H-chromen-4-one hydrochloride 1192136-06-3 C21H23NO6*ClH
8-(3-amino-3-methylbutyl)-3,5,7-trihydroxy-2-(4-methoxyphenyl)-4H-chromen-4-one hydrochloride
—— 3,5,7-trihydroxy-2-(3,4,5-trimethoxy-phenyl)-chromenylium; chloride 72117-71-6 C18H17O7*Cl
3,5,7-trihydroxy-2-(3,4,5-trimethoxy-phenyl)-chromenylium; chloride
—— 4α,5,7,3',4'-pentamethoxyflavan 88363-07-9 C20H24O6
4α,5,7,3',4'-pentamethoxyflavan
—— rac-2-(3,4-difluorophenyl)-2H-chromene-3-carboxylic acid 1204754-87-9 C16H10F2O3
rac-2-(3,4-difluorophenyl)-2H-chromene-3-carboxylic acid
—— 2-(3-fluoro-4-methoxyphenyl)-6-[(3S)-3-methylpiperazin-1-yl]-4H-chromen-4-one 1459286-14-6 C21H21FN2O3
2-(3-fluoro-4-methoxyphenyl)-6-[(3S)-3-methylpiperazin-1-yl]-4H-chromen-4-one
—— (2R,3S)-5-(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)-7-(methoxymethoxy)chroman-3-yl propionate 1365537-61-6 C41H40O8
(2R,3S)-5-(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)-7-(methoxymethoxy)chroman-3-yl propionate
—— 3'4'-O-dioctanoyl-(+)-D-catechin 904705-92-6 C31H42O8
3'4'-O-dioctanoyl-(+)-D-catechin
—— (2R,3S)-5-(benzyloxy)-2-(4-(benzyloxy)-3-methoxyphenyl)-7-(methoxymethoxy)chroman-3-yl propionate 1365537-60-5 C35H36O8
(2R,3S)-5-(benzyloxy)-2-(4-(benzyloxy)-3-methoxyphenyl)-7-(methoxymethoxy)chroman-3-yl propionate
—— 3-O-[2-O-benzyl-3,4-di-O-acetyl-β-L-arabinopyranosyl-(1->4)-2,3-di-O-acetyl-α-L-rhamnopyranoside]-4'-O-benzyl-7-O-allylkaempferol 1307876-19-2 C51H52O18
3-O-[2-O-benzyl-3,4-di-O-acetyl-β-L-arabinopyranosyl-(1->4)-2,3-di-O-acetyl-α-L-rhamnopyranoside]-4'-O-benzyl-7-O-allylkaempferol
—— 2-[2-(3,4-Dimethoxyphenyl)-4-oxochromen-8-yl]acetonitrile 87626-97-9 C19H15NO4
2-[2-(3,4-Dimethoxyphenyl)-4-oxochromen-8-yl]acetonitrile
—— (R,S)-5,7-dimethoxymethoxy-8-(1'-geranyl)flavanone 261758-71-8 C29H36O6
(R,S)-5,7-dimethoxymethoxy-8-(1'-geranyl)flavanone
—— 3-O-acetyl-6-methoxymethyl-5,7,3',4'-tetra-O-methyl-(+)-catechin 101751-82-0 C23H28O8
3-O-acetyl-6-methoxymethyl-5,7,3',4'-tetra-O-methyl-(+)-catechin
—— 2-phenylchroman-4-one [4-(methylsulfonyl)phenyl]hydrazone 906461-55-0 C22H20N2O3S
2-phenylchroman-4-one [4-(methylsulfonyl)phenyl]hydrazone
—— (2R,3R)-5,7-bis(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)chroman-3-yl (1s,4S)-4-((tert-butyldimethylsilyl)oxy)cyclohexane-1-carboxylate 1608504-14-8 C56H62O8Si
(2R,3R)-5,7-bis(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)chroman-3-yl (1s,4S)-4-((tert-butyldimethylsilyl)oxy)cyclohexane-1-carboxylate
—— 2-(2-aminophenyl)-5,7-dimethoxychromen-4-one 182220-42-4 C17H15NO4
2-(2-aminophenyl)-5,7-dimethoxychromen-4-one
—— 6-acetoxy-3-O-acetyl-3',4',5,7-tetra-O-methyl-(+)-catechin 69275-28-1 C23H26O9
6-acetoxy-3-O-acetyl-3',4',5,7-tetra-O-methyl-(+)-catechin
—— (R)-<5,8>-(+)-mesquitol-(+)-catechin 109671-62-7 C42H46O14
(R)-<5,8>-(+)-mesquitol-(+)-catechin
—— (3R,4S)-3,4-trans-4-<(2R,3S)-2,3-trans-3-acetoxy-3',4',5,7-tetramethoxyflavan-6-yl>-2',3',7-trimethoxyisoflavan 95541-50-7 C39H42O11
(3R,4S)-3,4-trans-4-<(2R,3S)-2,3-trans-3-acetoxy-3',4',5,7-tetramethoxyflavan-6-yl>-2',3',7-trimethoxyisoflavan
—— 7β-D-Glucopyranosyloxy-5-hydroxy-2'-methoxy-flavanon 27960-44-7 C22H24O10
7β-D-Glucopyranosyloxy-5-hydroxy-2'-methoxy-flavanon
—— cinnamtannin B1 4''-benzylthioether 114586-49-1 C52H42O18S
cinnamtannin B1 4''-benzylthioether
—— (2R,3R,4R)-2,3-cis-3,4-trans-3',4',7,8-tetrahydroxy-4-<(2R,3S)-2,3-trans-3,3',4',5,7-pentahydroxyflavan-8-yl>flavan 78139-53-4 C30H26O11
(2R,3R,4R)-2,3-cis-3,4-trans-3',4',7,8-tetrahydroxy-4-<(2R,3S)-2,3-trans-3,3',4',5,7-pentahydroxyflavan-8-yl>flavan
—— (2R,3R)-5,7-bis(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)chroman-3-yl cyclohexanecarboxylate 1608504-34-2 C50H48O7
(2R,3R)-5,7-bis(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)chroman-3-yl cyclohexanecarboxylate
—— 6-methoxy-3-(6-methoxy-4-oxo-2,3-dihydrochromen-2-yl)chromen-4-one 90368-65-3 C20H16O6
6-methoxy-3-(6-methoxy-4-oxo-2,3-dihydrochromen-2-yl)chromen-4-one
—— (2R,3R)-2-(3-((tert-butoxycarbonyl)oxy)-4,5-dihydroxyphenyl)chromane-3,5,7-triyl tri-tert-butyl tricarbonate 1304014-19-4 C35H46O15
(2R,3R)-2-(3-((tert-butoxycarbonyl)oxy)-4,5-dihydroxyphenyl)chromane-3,5,7-triyl tri-tert-butyl tricarbonate
—— 3-O-benzyl-3',4',5,7-tetra-O-methyl-(+)-catechin 78376-75-7 C26H28O6
3-O-benzyl-3',4',5,7-tetra-O-methyl-(+)-catechin
—— Naringenin 7-O-(2'',6''-di-O-alpha-rhamnopyranosyl)-beta-glucopyranoside 98827-55-5 C33H42O18
Naringenin 7-O-(2'',6''-di-O-alpha-rhamnopyranosyl)-beta-glucopyranoside
—— 5,7-dihydroxy-2-(4-methoxy-2-((4-methoxybenzyl)oxy)phenyl)-3-(3-methylbut-2-en-1-yl)-6-(3-methylbutanoyl)-4H-chromen-4-one 1443276-34-3 C34H36O8
5,7-dihydroxy-2-(4-methoxy-2-((4-methoxybenzyl)oxy)phenyl)-3-(3-methylbut-2-en-1-yl)-6-(3-methylbutanoyl)-4H-chromen-4-one
—— 3,6,8-Trichlor-7-hydroxy-flavon 36752-38-2 C15H7Cl3O3
3,6,8-Trichlor-7-hydroxy-flavon
—— 4''',5,5''-Triacetoxy-4',7,7''-tri-O-methylcupressuflavon 32541-46-1 C39H30O13
4''',5,5''-Triacetoxy-4',7,7''-tri-O-methylcupressuflavon
—— 4-[4-[5,5-Bis(4-methoxyphenyl)-1',1',5',5'-tetramethyl-11-piperidin-1-ylspiro[6-oxapentacyclo[12.7.0.02,7.08,13.015,20]henicosa-1(14),2(7),3,8,10,12,15,17,19-nonaene-21,3'-cyclohexane]-10-yl]phenyl]morpholine 1278523-82-2 C58H62N2O4
4-[4-[5,5-Bis(4-methoxyphenyl)-1',1',5',5'-tetramethyl-11-piperidin-1-ylspiro[6-oxapentacyclo[12.7.0.02,7.08,13.015,20]henicosa-1(14),2(7),3,8,10,12,15,17,19-nonaene-21,3'-cyclohexane]-10-yl]phenyl]morpholine
—— 8-[2,3-Dimethoxy-5-(7-methoxy-4-oxo-4H-chromen-2-yl)-phenyl]-7-methoxy-2-(3,4,5-trimethoxy-phenyl)-chromen-4-one 98568-78-6 C37H32O11
8-[2,3-Dimethoxy-5-(7-methoxy-4-oxo-4H-chromen-2-yl)-phenyl]-7-methoxy-2-(3,4,5-trimethoxy-phenyl)-chromen-4-one
—— 6-methoxy-2-phenyl-5-(toluene-4-sulfonyloxy)-chromen-4-one 102593-82-8 C23H18O6S
6-methoxy-2-phenyl-5-(toluene-4-sulfonyloxy)-chromen-4-one
—— 5,7-Dimethoxy-4α-phenylsulfonylflavan 55539-45-2 C23H22O5S
5,7-Dimethoxy-4α-phenylsulfonylflavan
—— 3-Hydroxy-3'-methoxy-4'-benzyloxy-flavanon 35090-85-8 C23H20O5
3-Hydroxy-3'-methoxy-4'-benzyloxy-flavanon
—— (2R,3S,4S)-2,3-cis-3,4-trans-3,3',4',5,7-pentahydroxy-4-phenylthioflavan 86849-67-4 C21H18O6S
(2R,3S,4S)-2,3-cis-3,4-trans-3,3',4',5,7-pentahydroxy-4-phenylthioflavan
—— tri(tert-butyl) (2R,3S)-2-(2,2,4,4-tetraisopropylbenzo[f][1,3,5,2,4]trioxadisilepin-7-yl)chroman-3,5,7-triyl tricarbonate 1304014-13-8 C42H64O13Si2
tri(tert-butyl) (2R,3S)-2-(2,2,4,4-tetraisopropylbenzo[f][1,3,5,2,4]trioxadisilepin-7-yl)chroman-3,5,7-triyl tricarbonate
—— (4-oxo-2-phenyl-4H-chromen-7-yloxy)-acetic acid isopropyl ester 27654-56-4 C20H18O5
(4-oxo-2-phenyl-4H-chromen-7-yloxy)-acetic acid isopropyl ester
—— Epicatechin-(4β->8)-4α-benzylthioepicatechin 128900-23-2 C37H32O12S
Epicatechin-(4β->8)-4α-benzylthioepicatechin
—— 8,9-cis-9,10-trans-3,4,9,10-tetrahydro-2H,8H-pyrano<2,3-h>chromene 128428-20-6 C30H26O12
8,9-cis-9,10-trans-3,4,9,10-tetrahydro-2H,8H-pyrano<2,3-h>chromene
—— Acetic acid 4-oxo-2-phenyl-8-(1-phenyl-allyl)-4H-chromen-7-yl ester 132314-43-3 C26H20O4
Acetic acid 4-oxo-2-phenyl-8-(1-phenyl-allyl)-4H-chromen-7-yl ester
—— 3',4',7-Trichlorflavon 36774-80-8 C15H7Cl3O2
3',4',7-Trichlorflavon
—— 7-(benzyloxy)-3-hydroxy-2-(4-methoxyphenyl)-4H-chromen-4-one 35784-26-0 C23H18O5
7-(benzyloxy)-3-hydroxy-2-(4-methoxyphenyl)-4H-chromen-4-one