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酚类

酚类是一大类化合物,它们主要特征是分子中含有一个羟基(-OH)直接连接在苯环上。这类化合物广泛存在于自然界中,并且具有重要的生物、医药及工业应用价值。

结构与分类

酚类化合物的基本结构为苯环上的氧原子与羟基相连。根据羟基的位置不同,可将酚分为单酚和多酚两大类:

  • 单酚:每个分子仅有一个酚羟基。
  • 多酚:含有两个或多个酚羟基的化合物。
生物学意义
  1. 天然来源:酚广泛存在于植物、动物以及微生物中,如咖啡因中的茶酚、儿茶素等。
  2. 抗氧化作用:许多酚类物质具有较强的抗氧化性,能够清除体内的自由基,保护细胞免受氧化损伤。
  3. 抗菌活性:部分酚类化合物展示出显著的抗菌效果,可用于食品保鲜或开发抗生素。
工业应用
  1. 农药和杀虫剂:利用某些酚类化合物对特定昆虫的选择性毒性进行害虫控制。
  2. 染料工业:许多天然及合成染料都基于酚结构设计而成。
  3. 医药领域:作为原料或药物成分,例如阿司匹林的核心成分水杨酸就属于苯酚衍生物。
工业生产

酚类可以通过多种途径制备:

  • 通过煤焦油蒸馏或石油裂解得到的粗酚进行精炼获得。
  • 以苯或其他芳烃为原料,在催化剂作用下与水反应生成苯酚,此过程称为菲林斯勒反应(Fischer–Strassmann反应)。
注意事项

尽管酚类化合物具有广泛的应用前景,但它们也可能带来毒性问题。例如强酸性的酚类物质会对皮肤造成刺激甚至腐蚀。因此在使用时需注意安全防护措施。

以上是对酚类的简单介绍,涵盖了其基本定义、生物学意义及工业应用等方面的内容。

中文名称 英文名称 CAS号 化学式 结构式图片
—— 4-hydroxy-3-methoxybenzyl pentanoate 1073340-79-0 C13H18O4
4-hydroxy-3-methoxybenzyl pentanoate
—— 4-hydroxy-3-methoxybenzyl heptanoate 916911-63-2 C15H22O4
4-hydroxy-3-methoxybenzyl heptanoate
—— 4,4'-((1E,3E,5E)-hexa-1,3,5-triene-1,6-diyl)bis(2-methoxyphenol) 1443299-31-7 C20H20O4
4,4'-((1E,3E,5E)-hexa-1,3,5-triene-1,6-diyl)bis(2-methoxyphenol)
—— (S)-normetanephrine 35778-41-7 C9H13NO3
(S)-normetanephrine
—— (4,4'-((prop-2-yn-1-ylazanediyl)bis(methylene))bis(2,6-dimethoxyphenol)) 1246672-86-5 C21H25NO6
(4,4'-((prop-2-yn-1-ylazanediyl)bis(methylene))bis(2,6-dimethoxyphenol))
—— 2,5-bis(4-hydroxy-3,5-dimethoxy benzylidene)cyclopentanone 56720-22-0 C23H24O7
2,5-bis(4-hydroxy-3,5-dimethoxy benzylidene)cyclopentanone
—— 6-hydroxy-6-(3',5'-dimethoxy-4'-hydroxyphenyl)-1-hexene 116911-83-2 C14H20O4
6-hydroxy-6-(3',5'-dimethoxy-4'-hydroxyphenyl)-1-hexene
—— 5-(4-hydroxy-3,5-dimethoxybenzylidene)-1,3-dimethyl pyrimidine-2,4,6 (1H,3H,5H)-trione 328243-71-6 C15H16N2O6
5-(4-hydroxy-3,5-dimethoxybenzylidene)-1,3-dimethyl pyrimidine-2,4,6 (1H,3H,5H)-trione
—— 3,5-bis(4-hydroxy-3,5-dimethoxybenzylidene)tetrahydropyran-4-one 1334668-88-0 C23H24O8
3,5-bis(4-hydroxy-3,5-dimethoxybenzylidene)tetrahydropyran-4-one
—— (E)-4-((2-(benzo[d]thiazol-2-yl)-2-methylhydrazono)methyl)-2,6-dimethoxyphenol 1621252-74-1 C17H17N3O3S
(E)-4-((2-(benzo[d]thiazol-2-yl)-2-methylhydrazono)methyl)-2,6-dimethoxyphenol
—— (E)-benzyl-2-(4-hydroxy-3,5-dimethoxybenzylidene)hydrazinecarboxylate 1234475-46-7 C17H18N2O5
(E)-benzyl-2-(4-hydroxy-3,5-dimethoxybenzylidene)hydrazinecarboxylate
—— (2Z,5Z)-5-(4-hydroxy-3,5-dimethoxybenzylidene)-2-(4-methoxyphenylimino)-3-phenylthiazolidin-4-one 1194838-23-7 C25H22N2O5S
(2Z,5Z)-5-(4-hydroxy-3,5-dimethoxybenzylidene)-2-(4-methoxyphenylimino)-3-phenylthiazolidin-4-one
—— 9-(4-Hydroxy-3,5-dimethoxy-phenyl)-6,9-dihydro-1,3,5,7-tetraoxa-dicyclopenta[b,g]naphthalen-8-one 191023-05-9 C20H16O8
9-(4-Hydroxy-3,5-dimethoxy-phenyl)-6,9-dihydro-1,3,5,7-tetraoxa-dicyclopenta[b,g]naphthalen-8-one
—— 2.6-Dimethoxy-4-(2<i>t</i>-nitro-vinyl-(1<i>r</i>))-phenol 70622-87-6 C10H11NO5
2.6-Dimethoxy-4-(2<i>t</i>-nitro-vinyl-(1<i>r</i>))-phenol
—— cis-4-propenylsyringol 26624-13-5 C11H14O3
cis-4-propenylsyringol
—— (Z)-5-((Z)-4-hydroxy-3,5-dimethoxybenzylidene)-3-(4-methoxyphenyl)-2-(phenylimino)thiazolidin-4-one 1082953-72-7 C25H22N2O5S
(Z)-5-((Z)-4-hydroxy-3,5-dimethoxybenzylidene)-3-(4-methoxyphenyl)-2-(phenylimino)thiazolidin-4-one
—— (E)-N'-(4-hydroxy-3,5-dimethoxybenzylidene)isonicotinohydrazide 1064312-68-0 C15H15N3O4
(E)-N'-(4-hydroxy-3,5-dimethoxybenzylidene)isonicotinohydrazide
—— [(E)-2-(4-Hydroxy-3,5-dimethoxy-phenyl)-vinyl]-phosphonothioic acid S-(2-acetylamino-ethyl) ester O-ethyl ester 872426-24-9 C16H24NO6PS
[(E)-2-(4-Hydroxy-3,5-dimethoxy-phenyl)-vinyl]-phosphonothioic acid S-(2-acetylamino-ethyl) ester O-ethyl ester
—— 4-[[[4-[[Bis[(4-hydroxy-3,5-dimethoxyphenyl)methyl]amino]methyl]phenyl]methyl-[(4-hydroxy-3,5-dimethoxyphenyl)methyl]amino]methyl]-2,6-dimethoxyphenol 1201916-25-7 C44H52N2O12
4-[[[4-[[Bis[(4-hydroxy-3,5-dimethoxyphenyl)methyl]amino]methyl]phenyl]methyl-[(4-hydroxy-3,5-dimethoxyphenyl)methyl]amino]methyl]-2,6-dimethoxyphenol
—— t-butyl 4-((2Z,5Z)-5-(4-hydroxy-3,5-dimethoxybenzylidene)-4-oxo-2-(phenylimino)thiazolidin-3-yl)butanoate 1082953-70-5 C26H30N2O6S
t-butyl 4-((2Z,5Z)-5-(4-hydroxy-3,5-dimethoxybenzylidene)-4-oxo-2-(phenylimino)thiazolidin-3-yl)butanoate
—— 4-Heptadecyl-2,6-dimethoxy-phenol 148665-93-4 C25H44O3
4-Heptadecyl-2,6-dimethoxy-phenol
—— 2-(3,5-dimethoxy-4-hydroxyphenyl)-3-(3-chloropropyl)-1,3-thiazolidin-4-one 180090-57-7 C14H18ClNO4S
2-(3,5-dimethoxy-4-hydroxyphenyl)-3-(3-chloropropyl)-1,3-thiazolidin-4-one
—— 4-[2-[Methyl(2-phenylethyl)amino]ethyl]benzene-1,2-diol 70044-84-7 C17H21NO2
4-[2-[Methyl(2-phenylethyl)amino]ethyl]benzene-1,2-diol
—— tert-butyl 4-((Z)-((Z)-5-(4-hydroxy-3,5-dimethoxybenzylidene)-4-oxo-2-phenylthiazolidin-3-ylidene)amino)benzylcarbamate 1082953-55-6 C30H31N3O6S
tert-butyl 4-((Z)-((Z)-5-(4-hydroxy-3,5-dimethoxybenzylidene)-4-oxo-2-phenylthiazolidin-3-ylidene)amino)benzylcarbamate
—— 2-[1-(4-hydroxy-3,5-dimethoxy-phenyl)-meth-(Z)-ylidene]-6-pyridin-4-yl-imidazo[2,1-b]thiazol-3-one 1567848-17-2 C19H15N3O4S
2-[1-(4-hydroxy-3,5-dimethoxy-phenyl)-meth-(Z)-ylidene]-6-pyridin-4-yl-imidazo[2,1-b]thiazol-3-one
—— 5-(4-hydroxy-3,5-dimethoxybenzylidene)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione 330567-17-4 C13H12N2O5S
5-(4-hydroxy-3,5-dimethoxybenzylidene)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione
—— (4-hydroxy-3,5-dimethoxybenzylidene)-2-iminothiazolidin-4-one 327031-31-2 C12H12N2O4S
(4-hydroxy-3,5-dimethoxybenzylidene)-2-iminothiazolidin-4-one
—— (4-hydroxy-3,5-dimethoxybenzylidene)thiazolidine-2,4-one 127378-45-4 C12H11NO5S
(4-hydroxy-3,5-dimethoxybenzylidene)thiazolidine-2,4-one
—— 4-(2-cyanoethyl)-2,6-dimethoxyphenol 54738-27-1 C11H13NO3
4-(2-cyanoethyl)-2,6-dimethoxyphenol
—— (E)-benzyl 2-(4-hydroxy-3,5-dimethoxybenzylidene)-1-methylhydrazinecarboxylate hydrochloride 1621252-69-4 C18H20N2O5*ClH
(E)-benzyl 2-(4-hydroxy-3,5-dimethoxybenzylidene)-1-methylhydrazinecarboxylate hydrochloride
—— (Z)-5-(4-hydroxy-3,5-dimethoxybenzylidene)-2-thioxothiazolidin-4-one 99988-74-6 C12H11NO4S2
(Z)-5-(4-hydroxy-3,5-dimethoxybenzylidene)-2-thioxothiazolidin-4-one
—— ethyl 4-(4-hydroxy-3,5-dimethoxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate 940809-75-6 C16H20N2O5S
ethyl 4-(4-hydroxy-3,5-dimethoxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
—— 4-(1-Hydroxy-heptyl)-2-methoxy-phenol 114515-50-3 C14H22O3
4-(1-Hydroxy-heptyl)-2-methoxy-phenol
—— (4-hydroxy-3,5-dimethoxy-phenyl)-glyoxylic acid 81947-97-9 C10H10O6
(4-hydroxy-3,5-dimethoxy-phenyl)-glyoxylic acid
—— 1-(4-hydroxy-3-methoxyphenyl)-4,4-dimethylpentan-3-one 106174-97-4 C14H20O3
1-(4-hydroxy-3-methoxyphenyl)-4,4-dimethylpentan-3-one
—— 4-hydroxy-3-methoxymandelic acid (phenylmethyl) ester 139473-89-5 C16H16O5
4-hydroxy-3-methoxymandelic acid (phenylmethyl) ester
—— 4-hydroxy-3-methoxyphenyl alpha acetoxyacetic acid 153750-09-5 C11H12O6
4-hydroxy-3-methoxyphenyl alpha acetoxyacetic acid
—— methyl vanillmandelate 2911-74-2 C10H12O5
methyl vanillmandelate
—— 4-ethyl-2-thiophen-3-yl-phenol 847345-47-5 C12H12OS
4-ethyl-2-thiophen-3-yl-phenol
—— hydron;4-[2-[pentyl(2-phenylethyl)amino]ethyl]benzene-1,2-diol;bromide —— C21H30BrNO2
hydron;4-[2-[pentyl(2-phenylethyl)amino]ethyl]benzene-1,2-diol;bromide
—— 4-[2-(Isopropyl-phenethyl-amino)-ethyl]-benzene-1,2-diol 70045-11-3 C19H25NO2
4-[2-(Isopropyl-phenethyl-amino)-ethyl]-benzene-1,2-diol
—— N-(3,4-Dihydroxy-phenethyl)-5-benzyloxy-3-indolacetamid 70265-25-7 C25H24N2O4
N-(3,4-Dihydroxy-phenethyl)-5-benzyloxy-3-indolacetamid
—— Phenethylamine, 3,4-dihydroxy-N-(p-nitrophenethyl)-N-propyl-, acetate 70045-05-5 C21H28N2O6
Phenethylamine, 3,4-dihydroxy-N-(p-nitrophenethyl)-N-propyl-, acetate
—— 4-(2-(N,N-Diphenethylamino)ethyl)pyrocatechol oxalate (2:1) 70045-18-0 C50H56N2O8
4-(2-(N,N-Diphenethylamino)ethyl)pyrocatechol oxalate (2:1)
—— hydron;4-[2-(2-phenylethylamino)ethyl]benzene-1,2-diol;bromide —— C16H20BrNO2
hydron;4-[2-(2-phenylethylamino)ethyl]benzene-1,2-diol;bromide
—— Pyrocatechol, 4-(2-(N-ethylphenethylamino)ethyl)-, oxalate (2:1) 70044-93-8 C38H48N2O8
Pyrocatechol, 4-(2-(N-ethylphenethylamino)ethyl)-, oxalate (2:1)
—— Pyrocatechol, 4-(2-(N-benzylphenethylamino)ethyl)-, oxalate (1:1) 70045-15-7 C25H27NO6
Pyrocatechol, 4-(2-(N-benzylphenethylamino)ethyl)-, oxalate (1:1)
—— 4-[2-[butyl(2-phenylethyl)amino]ethyl]benzene-1,2-diol;hydron;bromide —— C20H28BrNO2
4-[2-[butyl(2-phenylethyl)amino]ethyl]benzene-1,2-diol;hydron;bromide
—— Guaiacol, 4-(2-(phenethylamino)ethyl)-, hydrochloride 70044-81-4 C17H22ClNO2
Guaiacol, 4-(2-(phenethylamino)ethyl)-, hydrochloride
—— 4-(3-hydroxy-4,5-dimethoxy-thiobenzoyl)-morpholine 70733-91-4 C13H17NO4S
4-(3-hydroxy-4,5-dimethoxy-thiobenzoyl)-morpholine