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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
—— (5R)-1,2-O-isopropylidene-3-O-methyl-5-(2-hydroxyphenyl)-α-D-xylofuranose 124738-88-1 C15H20O6
(5R)-1,2-O-isopropylidene-3-O-methyl-5-(2-hydroxyphenyl)-α-D-xylofuranose
—— (5S)-1,2-O-isopropylidene-3-O-methyl-5-(2-hydroxyphenyl)-α-D-xylofuranose 124738-87-0 C15H20O6
(5S)-1,2-O-isopropylidene-3-O-methyl-5-(2-hydroxyphenyl)-α-D-xylofuranose
—— 5-chlorosalicylaldehyde guanylhydrazone 15996-57-3 C8H9ClN4O
5-chlorosalicylaldehyde guanylhydrazone
—— (E)-1-(2-Hydroxy-5-methyl-phenyl)-3-thiophen-2-yl-propenone 51956-77-5 C14H12O2S
(E)-1-(2-Hydroxy-5-methyl-phenyl)-3-thiophen-2-yl-propenone
—— 2,3,4-trihydroxy-5-hydroxymethylbenzaldehyde 84018-87-1 C8H8O5
2,3,4-trihydroxy-5-hydroxymethylbenzaldehyde
—— 3-(2-furyl)-1-(2'-hydroxy-5'-methylphenyl)-2-propen-1-one 40664-94-6 C14H12O3
3-(2-furyl)-1-(2'-hydroxy-5'-methylphenyl)-2-propen-1-one
—— 4-(3-amino-5-phenyl-1,2,4-triazin-6-yl)-2,6-dimethylphenol 1321513-22-7 C17H16N4O
4-(3-amino-5-phenyl-1,2,4-triazin-6-yl)-2,6-dimethylphenol
—— 4-(3-amino-5-phenyl-1,2,4-triazin-6-yl)-2-chlorophenol 1321513-23-8 C15H11ClN4O
4-(3-amino-5-phenyl-1,2,4-triazin-6-yl)-2-chlorophenol
—— ethyl (2S)-2-(3,4-dihydroxyphenyl)-3,3,3-trifluoro-2-hydroxypropanoate 1016638-56-4 C11H11F3O5
ethyl (2S)-2-(3,4-dihydroxyphenyl)-3,3,3-trifluoro-2-hydroxypropanoate
—— 2-hydroxybenzaldehyde 20286-84-4 C13H19NO3
2-hydroxybenzaldehyde
—— 2,6-bis<N-(2'-hydroxyethyl)-N-methylaminomethyl>-4-nitrophenol 121836-26-8 C14H23N3O5
2,6-bis<N-(2'-hydroxyethyl)-N-methylaminomethyl>-4-nitrophenol
—— ethyl 4-(3-bromo-4-hydroxyphenyl)butanoate 246219-29-4 C12H15BrO3
ethyl 4-(3-bromo-4-hydroxyphenyl)butanoate
—— (Z)-5-(2-hydroxy-5-methoxybenzylidene)-2,3-dimethyl-3,5-dihydro-4H-imidazol-4-one 1338081-21-2 C13H14N2O3
(Z)-5-(2-hydroxy-5-methoxybenzylidene)-2,3-dimethyl-3,5-dihydro-4H-imidazol-4-one
—— 5-Methylvanillylalkohol 37987-18-1 C9H12O3
5-Methylvanillylalkohol
—— 4-phenyldimethylsilylphenole 74027-99-9 C14H16OSi
4-phenyldimethylsilylphenole
—— 4-chloro-3-trimethylsilanylphenol 1004322-73-9 C9H13ClOSi
4-chloro-3-trimethylsilanylphenol
—— 2-bromo-5-methoxy-3-[(Z)-pentadec-10-enyl]phenol 148808-18-8 C22H35BrO2
2-bromo-5-methoxy-3-[(Z)-pentadec-10-enyl]phenol
—— 4-<3-(1-pyrazolyl)propyl>phenol hydrochloride 88670-70-6 C12H14N2O*ClH
4-<3-(1-pyrazolyl)propyl>phenol hydrochloride
—— 1-(4-propylcyclohexyl)-2-(4-hydroxyphenyl)ethane 133151-86-7 C17H26O
1-(4-propylcyclohexyl)-2-(4-hydroxyphenyl)ethane
—— 2-Hydroxy-acetophenon-(dimethyl-hydrazon) 5757-89-1 C10H14N2O
2-Hydroxy-acetophenon-(dimethyl-hydrazon)
—— tris(3-tert-butyl-5-methoxy-2-hydroxybenzyl)amine 1226976-99-3 C36H51NO6
tris(3-tert-butyl-5-methoxy-2-hydroxybenzyl)amine
—— 1-(2-hydroxy-5-methylphenyl)-1-methylcyclohex-2-ene 142688-23-1 C14H18O
1-(2-hydroxy-5-methylphenyl)-1-methylcyclohex-2-ene
—— 4-nitro-2,6-bis(pyrrolidin-1'-ylmethyl)phenol 121836-29-1 C16H23N3O3
4-nitro-2,6-bis(pyrrolidin-1'-ylmethyl)phenol
—— 2-(2,2-dimethyl-[1,3]dioxan-5-yl)-5-methyl-phenol 896745-82-7 C13H18O3
2-(2,2-dimethyl-[1,3]dioxan-5-yl)-5-methyl-phenol
—— Ethyl 3-(3,5-dibromo-4-hydroxyphenyl)-2-ethoxypropanoate 544478-45-7 C13H16Br2O4
Ethyl 3-(3,5-dibromo-4-hydroxyphenyl)-2-ethoxypropanoate
—— 1-(5''-hydroxy-2''-methoxyphenyl)-4-(3',4'-dimethoxyphenyl)butane 144849-34-3 C19H24O4
1-(5''-hydroxy-2''-methoxyphenyl)-4-(3',4'-dimethoxyphenyl)butane
—— 5-N-(β-hydroxyethyl)amino-4-merthoxy-2-methylphenol 137290-86-9 C10H15NO3
5-N-(β-hydroxyethyl)amino-4-merthoxy-2-methylphenol
—— Ethyl 3-(3-bromo-4-hydroxyphenyl)-2-ethoxypropanoate 544478-44-6 C13H17BrO4
Ethyl 3-(3-bromo-4-hydroxyphenyl)-2-ethoxypropanoate
—— 4-(2-{(1R,2R,3R)-3-Hydroxy-2-[(E)-(S)-3-hydroxy-4-(4-hydroxy-3-methyl-phenyl)-but-1-enyl]-5-oxo-cyclopentyl}-ethylsulfanyl)-butyric acid methyl ester 256382-09-9 C23H32O6S
4-(2-{(1R,2R,3R)-3-Hydroxy-2-[(E)-(S)-3-hydroxy-4-(4-hydroxy-3-methyl-phenyl)-but-1-enyl]-5-oxo-cyclopentyl}-ethylsulfanyl)-butyric acid methyl ester
—— 3-chloro-4-hydroxy-6-methoxy-2-methylbenzaldehyde 777090-48-9 C9H9ClO3
3-chloro-4-hydroxy-6-methoxy-2-methylbenzaldehyde
—— 4-trifluoromethoxy-2-(α-hydroxyethyl)phenol 146575-63-5 C9H9F3O3
4-trifluoromethoxy-2-(α-hydroxyethyl)phenol
—— 2-Chloro-3-(2-hydroxy-4,5-dimethoxyphenyl)-6-methoxy-5-methylcyclohexa-2,5-diene-1,4-dione 180912-30-5 C16H15ClO6
2-Chloro-3-(2-hydroxy-4,5-dimethoxyphenyl)-6-methoxy-5-methylcyclohexa-2,5-diene-1,4-dione
—— 4-Aethoxyresorcinol 55085-14-8 C8H10O3
4-Aethoxyresorcinol
—— α-tert.-Butylaminomethyl-4-hydroxy-3-(1,2-dihydroxyethyl)benzylalkohol 63296-03-7 C14H23NO4
α-tert.-Butylaminomethyl-4-hydroxy-3-(1,2-dihydroxyethyl)benzylalkohol
—— 4-{(2R)-2-[({(2S)-2-hydroxy-3-[4-(2-methoxyethyl)phenoxy]propyl}amino)methyl]-3,4-dihydro-2H-chromen-6-yl}benzoic acid 437764-38-0 C29H33NO6
4-{(2R)-2-[({(2S)-2-hydroxy-3-[4-(2-methoxyethyl)phenoxy]propyl}amino)methyl]-3,4-dihydro-2H-chromen-6-yl}benzoic acid
—— 1-(2-ethoxyethyl)-4-methoxybenzene 174460-92-5 C11H16O2
1-(2-ethoxyethyl)-4-methoxybenzene
—— 4-chloro-6-pentyl-resorcinol 99858-01-2 C11H15ClO2
4-chloro-6-pentyl-resorcinol
—— 2-amino-3,4,5-trimethylphenol 114997-86-3 C9H13NO
2-amino-3,4,5-trimethylphenol
—— 2,15-bis-(4-hydroxy-3-methoxy-phenyl)-1,3,14,16-tetrathia-cyclohexacosane 124120-88-3 C36H56O4S4
2,15-bis-(4-hydroxy-3-methoxy-phenyl)-1,3,14,16-tetrathia-cyclohexacosane
—— (4-ethyl-1,6-dihydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid 1265355-04-1 C11H13BO5
(4-ethyl-1,6-dihydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid
—— 3-[1-(Pyrid-2-yl-Methyl)4-Piperidinylamino]-1-(4-Hydroxy-Phenoxy)-2-Propanol 252578-07-7 C20H27N3O3
3-[1-(Pyrid-2-yl-Methyl)4-Piperidinylamino]-1-(4-Hydroxy-Phenoxy)-2-Propanol
—— diethyl (hydroxy(2-hydroxy-5-nitrophenyl)methyl)phosphonate 204130-59-6 C11H16NO7P
diethyl (hydroxy(2-hydroxy-5-nitrophenyl)methyl)phosphonate
—— [4-(2-hydroxy(213C)ethyl)phenyl] acetate 208644-96-6 C10H12O3
[4-(2-hydroxy(213C)ethyl)phenyl] acetate
—— [8-13C]-4-hydroxyphenylethanol 208644-95-5 C8H10O2
[8-13C]-4-hydroxyphenylethanol
—— (S)-5-<(3,5-dichloro-2-hydroxy-6-methoxybenzamido)methyl>-1-ethyl-2-pyrrolidone 145351-55-9 C15H18Cl2N2O4
(S)-5-<(3,5-dichloro-2-hydroxy-6-methoxybenzamido)methyl>-1-ethyl-2-pyrrolidone
—— (1E,3E,5E)-1-(4-hydroxy-3,5-dimethoxyphenyl)-6-phenyl-1,3,5-hexatriene 1206103-29-8 C20H20O3
(1E,3E,5E)-1-(4-hydroxy-3,5-dimethoxyphenyl)-6-phenyl-1,3,5-hexatriene
—— 5-{[(3-hydroxy-4-methoxyphenyl)amino]methylene}-2,2-dimethyl-1,3-dioxane-4,6-dione 205448-27-7 C14H15NO6
5-{[(3-hydroxy-4-methoxyphenyl)amino]methylene}-2,2-dimethyl-1,3-dioxane-4,6-dione
—— 4-(4-Hydroxy-2-methyl-phenyl)-butanol-(1) 19143-97-6 C11H16O2
4-(4-Hydroxy-2-methyl-phenyl)-butanol-(1)
—— 4-(1,3-dithiolan-2-yl)benzene-1,2-diol 83521-70-4 C9H10O2S2
4-(1,3-dithiolan-2-yl)benzene-1,2-diol
—— (Z,Z)-5-(3,4-dihydroxybenzylidene)-2-isopropylimino-3-phenyl-thiazolidin-4-one 1228117-20-1 C19H18N2O3S
(Z,Z)-5-(3,4-dihydroxybenzylidene)-2-isopropylimino-3-phenyl-thiazolidin-4-one