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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
—— 5.7-Dihydroxy-6-allyl-flavon 15013-81-7 C18H14O4
5.7-Dihydroxy-6-allyl-flavon
—— 1389319-76-9 C18H14ClNO4
—— 14,14-Bis(4-methoxyphenyl)-1',1'-dimethyl-21,21-di(propan-2-yl)spiro[15,20-dioxa-22-thiahexacyclo[15.7.0.02,10.03,8.011,16.019,23]tetracosa-1(24),2(10),3,5,7,11(16),12,17,19(23)-nonaene-9,4'-cyclohexane] 1398417-06-5 C48H50O4S
14,14-Bis(4-methoxyphenyl)-1',1'-dimethyl-21,21-di(propan-2-yl)spiro[15,20-dioxa-22-thiahexacyclo[15.7.0.02,10.03,8.011,16.019,23]tetracosa-1(24),2(10),3,5,7,11(16),12,17,19(23)-nonaene-9,4'-cyclohexane]
—— (Z)-1-(1-(3-benzylidene-1,3-dihydroisobenzofuran-1-yl)cyclopropyl)-3-cyclopropylisoquinoline 1589566-19-7 C30H25NO
(Z)-1-(1-(3-benzylidene-1,3-dihydroisobenzofuran-1-yl)cyclopropyl)-3-cyclopropylisoquinoline
—— 6-Acetyl-2-phenyl-3-propan-2-ylchromen-4-one 92757-75-0 C20H18O3
6-Acetyl-2-phenyl-3-propan-2-ylchromen-4-one
—— 3-(4-chloro-phenyl)-1-phenyl-(3ar,8bc)-3a,8b-dihydro-1H-benzo[4,5]furo[3,2-c]pyrazole 40277-68-7 C21H15ClN2O
3-(4-chloro-phenyl)-1-phenyl-(3ar,8bc)-3a,8b-dihydro-1H-benzo[4,5]furo[3,2-c]pyrazole
—— (2S,3S,4R,8S,9R)-2,8-Bis-(3,4-dihydroxy-phenyl)-4-(2,4-dihydroxy-phenyl)-3,4,9,10-tetrahydro-2H,8H-pyrano[2,3-f]chromene-3,5,9-triol 130932-45-5 C30H26O11
(2S,3S,4R,8S,9R)-2,8-Bis-(3,4-dihydroxy-phenyl)-4-(2,4-dihydroxy-phenyl)-3,4,9,10-tetrahydro-2H,8H-pyrano[2,3-f]chromene-3,5,9-triol
—— 4'-Carboxy-5.6-benzoflavon 20093-93-0 C20H12O4
4'-Carboxy-5.6-benzoflavon
—— 1415657-65-6 C23H18O3
—— 6,8-Dinitro-7-<2-amino-ethoxy>-flavon 3427-70-1 C17H13N3O7
6,8-Dinitro-7-<2-amino-ethoxy>-flavon
—— 8-Jod-flavonol 92424-56-1 C15H9IO3
8-Jod-flavonol
—— 8-Fluor-4'-methoxy-flavanon 844-83-7 C16H13FO3
8-Fluor-4'-methoxy-flavanon
—— 2,2'-((((((4,4'-(((2-(2-(4-(4-oxo-4H-chromen-2-yl)phenoxy)ethoxy)ethyl)azanediyl)bis(methylene))bis(1H-1,2,3-triazole-4,1-diyl))bis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(4,1-phenylene))bis(4H-chromen-4-one) 1451741-52-8 C48H49N7O10
2,2'-((((((4,4'-(((2-(2-(4-(4-oxo-4H-chromen-2-yl)phenoxy)ethoxy)ethyl)azanediyl)bis(methylene))bis(1H-1,2,3-triazole-4,1-diyl))bis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(4,1-phenylene))bis(4H-chromen-4-one)
—— 5-hydroxy-4-oxo-2-phenyl-4H-chromene-6,8-disulfonic acid-dianilide 103035-79-6 C27H20N2O7S2
5-hydroxy-4-oxo-2-phenyl-4H-chromene-6,8-disulfonic acid-dianilide
—— 2-(6-methoxynaphthalen-2-yl)-2H-chromene 1532560-26-1 C20H16O2
2-(6-methoxynaphthalen-2-yl)-2H-chromene
—— methyl 5-((2S,4S)-2-(3-(((R)-1-(4-fluoro-3-methoxyphenyl)ethyl)amino)propyl)chroman-4-yl)-2-methylbenzoate 1451372-86-3 C30H34FNO4
methyl 5-((2S,4S)-2-(3-(((R)-1-(4-fluoro-3-methoxyphenyl)ethyl)amino)propyl)chroman-4-yl)-2-methylbenzoate
—— 2-[3-Benzyloxy-2-(4-chloro-phenyl)-4-oxo-4H-chromen-6-yl]-propionic acid methyl ester 141070-60-2 C26H21ClO5
2-[3-Benzyloxy-2-(4-chloro-phenyl)-4-oxo-4H-chromen-6-yl]-propionic acid methyl ester
—— 5,7-dibenzyloxy-2-(2,2-diphenylbenzo[d][1,3]dioxol-5-yl)-3-β-D-[2'',3''-di-O-(4-fluorobenzoyl)-4'',6''-O-isopropylidene]glucosyl-4H-chromen-4-one 1246840-51-6 C65H50F2O14
5,7-dibenzyloxy-2-(2,2-diphenylbenzo[d][1,3]dioxol-5-yl)-3-β-D-[2'',3''-di-O-(4-fluorobenzoyl)-4'',6''-O-isopropylidene]glucosyl-4H-chromen-4-one
—— 3-Chloro-6-fluoro-2-phenyl-chromen-4-one 75595-41-4 C15H8ClFO2
3-Chloro-6-fluoro-2-phenyl-chromen-4-one
—— (Z)-3-((naphthalen-2-ylmethylamino)methylene)-2-o-tolylchroman-4-one 1430097-95-2 C28H23NO2
(Z)-3-((naphthalen-2-ylmethylamino)methylene)-2-o-tolylchroman-4-one
—— 6-[(3S)-3-methylpiperazin-1-yl]-2-[4-(trifluoromethoxy)phenyl]-4H-chromen-4-one 1459286-41-9 C21H19F3N2O3
6-[(3S)-3-methylpiperazin-1-yl]-2-[4-(trifluoromethoxy)phenyl]-4H-chromen-4-one
—— 7-Benzyloxy-5-hydroxy-6,4'-dimethoxy-flavon 5928-41-6 C24H20O6
7-Benzyloxy-5-hydroxy-6,4'-dimethoxy-flavon
—— (E)-3-(carbethoxymethylene)-2,7-dimethoxyflavanone 80907-15-9 C21H20O6
(E)-3-(carbethoxymethylene)-2,7-dimethoxyflavanone
—— 6-[(3R,5S)-3,5-dimethylpiperazin-1-yl]-2-(4-methoxy-3-methylphenyl)-4H-chromen-4-one 1459286-29-3 C23H26N2O3
6-[(3R,5S)-3,5-dimethylpiperazin-1-yl]-2-(4-methoxy-3-methylphenyl)-4H-chromen-4-one
—— 6-(1,4-diazepan-1-yl)-2-(pyridin-3-yl)-4H-chromen-4-one 1459285-82-5 C19H19N3O2
6-(1,4-diazepan-1-yl)-2-(pyridin-3-yl)-4H-chromen-4-one
—— [4-(3,5-Diacetyloxy-12-methoxy-17-methyl-8,10-dioxatetracyclo[7.7.1.02,7.011,16]heptadeca-2(7),3,5,11(16),12,14-hexaen-9-yl)phenyl] acetate 2657-08-1 C29H26O9
[4-(3,5-Diacetyloxy-12-methoxy-17-methyl-8,10-dioxatetracyclo[7.7.1.02,7.011,16]heptadeca-2(7),3,5,11(16),12,14-hexaen-9-yl)phenyl] acetate
—— 1343513-57-4 C16H10BrNO4
—— 3'-chloro-4',7-dihydroxyflavanone 1262526-68-0 C15H11ClO4
3'-chloro-4',7-dihydroxyflavanone
—— 3-Methyl-7-allyloxy-3',4'-dimethoxy-flavon 18651-24-6 C21H20O5
3-Methyl-7-allyloxy-3',4'-dimethoxy-flavon
—— 7-amino-3-[4-(1-amino-cyclobutyl)-phenyl]-8-hydroxy-2-phenyl-chromen-4-one 1279086-51-9 C25H22N2O3
7-amino-3-[4-(1-amino-cyclobutyl)-phenyl]-8-hydroxy-2-phenyl-chromen-4-one
—— 1333238-48-4 C24H13ClF2N2O2
—— 7-acetoxy-2-(3,4,5-triacetoxy-phenyl)-chromen-4-one 98411-67-7 C23H18O10
7-acetoxy-2-(3,4,5-triacetoxy-phenyl)-chromen-4-one
—— O<sup>5</sup>,O<sup>7</sup>,O<sup>3'</sup>,O<sup>4'</sup>,O<sup>5'</sup>-Pentamethyl-O<sup>3</sup>-tosyl-Derivat des 5'-Hydroxy-(-)-epicatechins ('3-Tosyl-5,7,3',4',5'-pentamethoxy-(-)-epicatechin') 17291-08-6 C27H30O9S
O<sup>5</sup>,O<sup>7</sup>,O<sup>3'</sup>,O<sup>4'</sup>,O<sup>5'</sup>-Pentamethyl-O<sup>3</sup>-tosyl-Derivat des 5'-Hydroxy-(-)-epicatechins ('3-Tosyl-5,7,3',4',5'-pentamethoxy-(-)-epicatechin')
—— 5-Amino-2-[4-(N-methoxycarbonylmethyl)amino]phenyl-4H-benzopyran-4-one 130599-71-2 C18H16N2O4
5-Amino-2-[4-(N-methoxycarbonylmethyl)amino]phenyl-4H-benzopyran-4-one
—— 7-((2-cyanobenzyl)oxy)-4-oxo-2-phenyl-4H-chromene-3,5-diyl diacetate 1254040-73-7 C27H19NO7
7-((2-cyanobenzyl)oxy)-4-oxo-2-phenyl-4H-chromene-3,5-diyl diacetate
—— 8-{1-Hydroxy-2-[4-(2-methylphenyl)-1-piperazinyl]-ethyl}-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran hydrochloride 152735-30-3 C29H30N2O3*ClH
8-{1-Hydroxy-2-[4-(2-methylphenyl)-1-piperazinyl]-ethyl}-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran hydrochloride
—— 6-Amino-8-{3-[4-(2-methoxyphenyl)-1-piperazinyl]propyl carbamoyl}-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran 152736-29-3 C31H34N4O4
6-Amino-8-{3-[4-(2-methoxyphenyl)-1-piperazinyl]propyl carbamoyl}-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran
—— 5-(N-Acetyl)amino-2-(4-dimethylamino)phenyl-4H-benzopyran-4-one 130599-56-3 C19H18N2O3
5-(N-Acetyl)amino-2-(4-dimethylamino)phenyl-4H-benzopyran-4-one
—— 4-(4-dimethylamino-phenyl)-2-phenyl-4H-chromen-4-ol 855463-30-8 C23H21NO2
4-(4-dimethylamino-phenyl)-2-phenyl-4H-chromen-4-ol
—— (+/-)-cis-4'-methylflavan-4-ol 89839-88-3 C16H16O2
(+/-)-cis-4'-methylflavan-4-ol
—— 128893-32-3 C80H82O24
—— 1415657-64-5 C22H15ClO3
—— (3aS,13bS,13cR)-4,11-Dimethoxy-8a-(5-methoxy-2,2-dimethyl-2H-chromen-8-yl)-2-methyl-1,8a,13b,13c-tetrahydro-3aH-8,9-dioxa-benzo[fg]naphthacene-6-carbaldehyde 137460-79-8 C35H34O7
(3aS,13bS,13cR)-4,11-Dimethoxy-8a-(5-methoxy-2,2-dimethyl-2H-chromen-8-yl)-2-methyl-1,8a,13b,13c-tetrahydro-3aH-8,9-dioxa-benzo[fg]naphthacene-6-carbaldehyde
—— 2-(3,4-dimethoxy-phenyl)-5-hydroxy-6,7-dimethoxy-8-morpholin-4-ylmethyl-chromen-4-one 71306-34-8 C24H27NO8
2-(3,4-dimethoxy-phenyl)-5-hydroxy-6,7-dimethoxy-8-morpholin-4-ylmethyl-chromen-4-one
—— tetrahydrokuwanon C tetramethyl ether 68754-21-2 C29H38O6
tetrahydrokuwanon C tetramethyl ether
—— 3,3',4'-Trihydroxy-flavylium-chlorid 97320-20-2 C15H11O4*Cl
3,3',4'-Trihydroxy-flavylium-chlorid
—— beta-hydroxyethyl 2'.3.4'-trimethylflavone-8-carboxylate 90102-20-8 C21H20O5
beta-hydroxyethyl 2'.3.4'-trimethylflavone-8-carboxylate
—— 7,8-dimethoxy-2-(2-methoxymethoxy-phenyl)-chroman-4-one 110048-33-4 C19H20O6
7,8-dimethoxy-2-(2-methoxymethoxy-phenyl)-chroman-4-one
—— (-)-[2R,3R]-5,7-bis-benzyloxy-2-(3,4,5-tris-benzyloxyphenyl)-chroman-3-yl-amine 760958-39-2 C50H45NO6
(-)-[2R,3R]-5,7-bis-benzyloxy-2-(3,4,5-tris-benzyloxyphenyl)-chroman-3-yl-amine
—— 5-(6-Methoxynaphthalen-2-yl)-2,2-diphenylchromene 933066-92-3 C32H24O2
5-(6-Methoxynaphthalen-2-yl)-2,2-diphenylchromene