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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
—— 1-Piperidinepropionic acid, alpha-di-2-thienylmethylene-, ethyl ester, picrate 102952-40-9 C25H26N4O9S2
1-Piperidinepropionic acid, alpha-di-2-thienylmethylene-, ethyl ester, picrate
—— Ethanethioic acid, S-(2-(2-(2-(2-hydroxyphenyl)ethyl)-3-thiazolidinyl)-2-oxoethyl) ester 103195-82-0 C15H19NO3S2
Ethanethioic acid, S-(2-(2-(2-(2-hydroxyphenyl)ethyl)-3-thiazolidinyl)-2-oxoethyl) ester
—— TA-064 metabolite M-3 87081-59-2 C18H23NO5
TA-064 metabolite M-3
—— 2-(3-methoxy-4-hydroxyphenyl)-3-(4-bromophenyl)-4-thiazolidinone 1086685-56-4 C16H14BrNO3S
2-(3-methoxy-4-hydroxyphenyl)-3-(4-bromophenyl)-4-thiazolidinone
—— N-benzyl-5-(4-hydroxyphenyl)-3-methyl-4,5-dihydropyrazole-1-carboxamide 1107065-24-6 C18H19N3O2
N-benzyl-5-(4-hydroxyphenyl)-3-methyl-4,5-dihydropyrazole-1-carboxamide
—— (Z)-5-(4-hydroxy-3,5-dimethylbenzylidene)-3-(1-methylcyclohexylmethyl)thiazolidine-2,4-dione 1020066-83-4 C20H25NO3S
(Z)-5-(4-hydroxy-3,5-dimethylbenzylidene)-3-(1-methylcyclohexylmethyl)thiazolidine-2,4-dione
—— (5Z)-5-[(3,5-dibromo-4-hydroxyphenyl)methylidene]-3-[(1-methylcyclohexyl)methyl]-1,3-thiazolidine-2,4-dione 1020066-81-2 C18H19Br2NO3S
(5Z)-5-[(3,5-dibromo-4-hydroxyphenyl)methylidene]-3-[(1-methylcyclohexyl)methyl]-1,3-thiazolidine-2,4-dione
—— (Z)-5-(4-hydroxy-3-nitrobenzylidene)-3-(1-methylcyclohexylmethyl)thiazolidine-2,4-dione 1020066-78-7 C18H20N2O5S
(Z)-5-(4-hydroxy-3-nitrobenzylidene)-3-(1-methylcyclohexylmethyl)thiazolidine-2,4-dione
—— (Z)-5-(3-bromo-4-hydroxybenzylidene)-3-(1-methylcyclohexylmethyl)thiazolidine-2,4-dione 1020066-79-8 C18H20BrNO3S
(Z)-5-(3-bromo-4-hydroxybenzylidene)-3-(1-methylcyclohexylmethyl)thiazolidine-2,4-dione
—— (Z)-5-(4-hydroxy-3-methoxybenzylidene)-3-(1-methylcyclohexylmethyl)thiazolidine-2,4-dione 1020066-80-1 C19H23NO4S
(Z)-5-(4-hydroxy-3-methoxybenzylidene)-3-(1-methylcyclohexylmethyl)thiazolidine-2,4-dione
—— 4-Chloro-2-[1-(2-ethyl-1,3-dithian-2-yl)pent-4-en-2-yl]phenol 1015689-78-7 C17H23ClOS2
4-Chloro-2-[1-(2-ethyl-1,3-dithian-2-yl)pent-4-en-2-yl]phenol
—— 3-(1-methyl-3,6-dihydro-2H-pyridin-4-yl)phenol;hydrochloride 1012886-73-5 C12H15NO*ClH
3-(1-methyl-3,6-dihydro-2H-pyridin-4-yl)phenol;hydrochloride
—— 1,4-bis[(4-tert-butylsulfanylphenyl)ethynyl]-2,3-dihydroxybenzene 1030625-62-7 C30H30O2S2
1,4-bis[(4-tert-butylsulfanylphenyl)ethynyl]-2,3-dihydroxybenzene
—— (2R,5S)-3-acetyl-2-(2-hydroxyphenyl)-5-(D-arabino-tetritol-1-yl)oxazolidine 1008747-47-4 C15H21NO7
(2R,5S)-3-acetyl-2-(2-hydroxyphenyl)-5-(D-arabino-tetritol-1-yl)oxazolidine
—— cytosporone F 1004540-64-0 C18H22O5
cytosporone F
—— (E)-3,4,5-trimethoxystyryl-3-hydroxy-4-methoxybenzylsulfone 1005494-43-8 C19H22O7S
(E)-3,4,5-trimethoxystyryl-3-hydroxy-4-methoxybenzylsulfone
—— tris(3,4-dihydroxybenzyl)amine 633700-33-1 C21H21NO6
tris(3,4-dihydroxybenzyl)amine
—— 3,5-dihydroxybenzylamine hydrochloride 957864-31-2 C7H9NO2*ClH
3,5-dihydroxybenzylamine hydrochloride
—— 5-(4-hydroxy-3-methoxybenzylidene)-3-(4-methoxyphenyl)-2-thioxo-1,3-oxazolidin-4-one 1275574-72-5 C18H15NO5S
5-(4-hydroxy-3-methoxybenzylidene)-3-(4-methoxyphenyl)-2-thioxo-1,3-oxazolidin-4-one
—— N-[2-(4-Hydroxyphenyl)ethyl]-3-methylbutanamide 921607-20-7 C13H19NO2
N-[2-(4-Hydroxyphenyl)ethyl]-3-methylbutanamide
—— N-Cyclohexanoyl tyramine 727732-91-4 C15H21NO2
N-Cyclohexanoyl tyramine
—— 2-(4-Hydroxy-3-nitrophenyl)acetohydrazide 952183-03-8 C8H9N3O4
2-(4-Hydroxy-3-nitrophenyl)acetohydrazide
—— 2,3,4-trihydroxybenzylamine hydroiodide 79490-80-5 C7H9NO3*HI
2,3,4-trihydroxybenzylamine hydroiodide
—— 4-[1-Bromo-2-(methylamino)ethyl]benzene-1,2-diol;hydrobromide 7464-98-4 C9H13Br2NO2
4-[1-Bromo-2-(methylamino)ethyl]benzene-1,2-diol;hydrobromide
—— 2-[(2-Chloroethylamino)methyl]-4-nitrophenol;hydrochloride 56538-05-7 C9H12Cl2N2O3
2-[(2-Chloroethylamino)methyl]-4-nitrophenol;hydrochloride
—— 78899-79-3 C14H22NaO
—— 4-[Bis(2-chloroethyl)amino]benzene-1,2-diol;hydrochloride 3865-97-2 C10H14Cl3NO2
4-[Bis(2-chloroethyl)amino]benzene-1,2-diol;hydrochloride
—— 4-(5,6-Dihydroimidazo[2,1-b][1,3]thiazol-3-yl)phenol;hydrobromide 23224-08-0 C11H11BrN2OS
4-(5,6-Dihydroimidazo[2,1-b][1,3]thiazol-3-yl)phenol;hydrobromide
—— 1-Methyl-5-aza-1-azoniabicyclo[3.2.2]nonane;2,4,6-trinitrophenolate;dihydrobromide —— C14H21Br2N5O7
1-Methyl-5-aza-1-azoniabicyclo[3.2.2]nonane;2,4,6-trinitrophenolate;dihydrobromide
—— 2,4-Dinitrobenzene-1,3-diol;iron 6337-90-2 C6H4FeN2O6
2,4-Dinitrobenzene-1,3-diol;iron
—— Benzenemethanesulfonic acid,2-dihydroxy-, monosodium salt 4445-76-5 C7H8NaO5S+
Benzenemethanesulfonic acid,2-dihydroxy-, monosodium salt
—— 2,5-Trichloro-6-nitrophenol sodium salt 7361-14-0 C6H2Cl3NNaO3+
2,5-Trichloro-6-nitrophenol sodium salt
—— 4-(1-Hydroxy-2-pyrrolidin-1-ylethyl)benzene-1,2-diol;hydrochloride 5450-77-1 C12H18ClNO3
4-(1-Hydroxy-2-pyrrolidin-1-ylethyl)benzene-1,2-diol;hydrochloride
—— (4-hydroxy-3-nitro-phenyl)-trimethyl-arsonium; bromide 6333-55-7 Br*C9H13AsNO3
(4-hydroxy-3-nitro-phenyl)-trimethyl-arsonium; bromide
—— ethyl 2-amino-4-(3-hydroxyphenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylate 401464-53-7 C20H23NO5
ethyl 2-amino-4-(3-hydroxyphenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylate
—— Phenol, 2,3,4,6-tetrachloro-, sodium salt (1:1) 131-61-3 C6H2Cl4NaO+
Phenol, 2,3,4,6-tetrachloro-, sodium salt (1:1)
—— 2-Methoxy-4-((E)-3-methyl-but-1-enyl)-phenol 51346-42-0 C12H16O2
2-Methoxy-4-((E)-3-methyl-but-1-enyl)-phenol
—— 3-Nitro-4-hydroxy-N-(n-propyl)-benzamid 27519-71-7 C10H12N2O4
3-Nitro-4-hydroxy-N-(n-propyl)-benzamid
—— Monopotassium hydroquinone 52688-73-0 C6H5KO2
Monopotassium hydroquinone
—— 4-(1-Amino-2-hydroxyethyl)-2,6-dimethoxyphenol 1270526-85-6 C10H15NO4
4-(1-Amino-2-hydroxyethyl)-2,6-dimethoxyphenol
—— 4-(1-amino-2,2,2-trifluoroethyl)-2,6-dimethylphenol 511522-43-3 C10H12F3NO
4-(1-amino-2,2,2-trifluoroethyl)-2,6-dimethylphenol
—— 2-Methyl-4-(methylamino)phenol;sulfuric acid 35271-57-9 C8H13NO5S
2-Methyl-4-(methylamino)phenol;sulfuric acid
—— N-(diaminomethylideneamino)-3-hydroxy-4,5-dimethoxybenzamide;sulfuric acid 35607-24-0 C10H16N4O8S
N-(diaminomethylideneamino)-3-hydroxy-4,5-dimethoxybenzamide;sulfuric acid
—— Sodium trinitrophenolate 3324-58-1 C6H3N3NaO7+
Sodium trinitrophenolate
—— 2-Amino-3-chloro-4-nitro-phenol 78593-88-1 C6H5ClN2O3
2-Amino-3-chloro-4-nitro-phenol
—— 2-(4-Hydroxy-2-methylphenyl)guanidine 247234-45-3 C8H11N3O
2-(4-Hydroxy-2-methylphenyl)guanidine
—— N-[2-(4-Hydroxyphenyl)ethyl]-2-methylpropanamide 921607-19-4 C12H17NO2
N-[2-(4-Hydroxyphenyl)ethyl]-2-methylpropanamide
—— 1-Chloro-3-[4-[2-(2-propen-1-yloxy)ethyl]phenoxy]-2-propanol 884340-62-9 C14H19ClO3
1-Chloro-3-[4-[2-(2-propen-1-yloxy)ethyl]phenoxy]-2-propanol
—— 1-<4-Hydroxy-3-methoxy-phenyl>-hexan-3-on 53172-00-2 C13H18O3
1-<4-Hydroxy-3-methoxy-phenyl>-hexan-3-on
—— 6-(3-Chloro-4-hydroxyphenoxy)hexyl 2-propenoate 620970-28-7 C15H19ClO4
6-(3-Chloro-4-hydroxyphenoxy)hexyl 2-propenoate