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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
—— 6-Hydroxybentazone —— C10H12N2O4S
6-Hydroxybentazone
—— 5-hydroxyconiferyl alcohol —— C10H12O4
5-hydroxyconiferyl alcohol
—— dihydrotridentatol C —— C10H11NOS2
dihydrotridentatol C
—— 2,4-dinitro-3,5-diethylphenol —— C10H12N2O5
2,4-dinitro-3,5-diethylphenol
—— 20-O-methylavarol —— C22H32O2
20-O-methylavarol
—— 4-Methyl-2-(1-methyl-pentadecyl)-phenol —— C23H40O
4-Methyl-2-(1-methyl-pentadecyl)-phenol
—— N'-(2-hydroxy-3-methoxyphenylmethylidene)-3-pyridinecarbohydrazide —— C14H13N3O3
N'-(2-hydroxy-3-methoxyphenylmethylidene)-3-pyridinecarbohydrazide
—— 5-[4-hydroxy-2-(3-hydroxypentyl)-3,5,6-trimethylphenoxy]pentanoic acid —— C19H30O5
5-[4-hydroxy-2-(3-hydroxypentyl)-3,5,6-trimethylphenoxy]pentanoic acid
—— 5-[4-hydroxy-2-(3-oxopentyl)-3,5,6-trimethylphenoxy]pentanoic acid —— C19H28O5
5-[4-hydroxy-2-(3-oxopentyl)-3,5,6-trimethylphenoxy]pentanoic acid
—— 5-[4-hydroxy-2-(3-oxobutyl)-3,5,6-trimethylphenoxy]pentanoic acid —— C18H26O5
5-[4-hydroxy-2-(3-oxobutyl)-3,5,6-trimethylphenoxy]pentanoic acid
—— 3-bromo-4-methylbenzene-1,2-diol —— C7H7BrO2
3-bromo-4-methylbenzene-1,2-diol
—— N-[3-({4-[(3-aminopropyl)amino]butyl}amino)propyl]-3-(2-hydroxyphenyl)propanamide —— C19H34N4O2
N-[3-({4-[(3-aminopropyl)amino]butyl}amino)propyl]-3-(2-hydroxyphenyl)propanamide
—— 3,3'-bis[3-(2-hydroxyphenyl)]-N,N'-(4,9-diazadodecane-1,12-diyl)bis[propanamide] —— C28H42N4O4
3,3'-bis[3-(2-hydroxyphenyl)]-N,N'-(4,9-diazadodecane-1,12-diyl)bis[propanamide]
—— N1,N5,N10,N14-tetrakis[3-(4-hydroxyphenyl)propanoyl]-1,5,10,14-tetraazatetradecane —— C46H58N4O8
N1,N5,N10,N14-tetrakis[3-(4-hydroxyphenyl)propanoyl]-1,5,10,14-tetraazatetradecane
—— N-Hmb-Gly-OH —— C10H13NO4
N-Hmb-Gly-OH
—— N,N',N"-tris(3,4,5-trihydroxybenzoyl)spermidine —— C28H31N3O12
N,N',N"-tris(3,4,5-trihydroxybenzoyl)spermidine
—— 4-methyl-2-(2-hydroxyphenyl)oxazoline —— C10H11NO2
4-methyl-2-(2-hydroxyphenyl)oxazoline
—— 2-(4-ethyl-4,5-dihydrooxazol-2-yl)phenol —— C11H13NO2
2-(4-ethyl-4,5-dihydrooxazol-2-yl)phenol
—— 4-isoxazol-4-ylphenol —— C9H7NO2
4-isoxazol-4-ylphenol
—— 2-amino-4-hydroxy-5-methoxybenzonitrile —— C8H8N2O2
2-amino-4-hydroxy-5-methoxybenzonitrile
—— 5-(3-hydroxy-4-methoxyphenyl)-4-(3,4,5-trimethoxyphenyl)-3H-1,2-dithiole-3-thione —— C19H18O5S3
5-(3-hydroxy-4-methoxyphenyl)-4-(3,4,5-trimethoxyphenyl)-3H-1,2-dithiole-3-thione
—— 4-(1-hydroxy-1-trifluoromethyl-2,2,2-trifluoroethyl)-2-methylphenol —— C10H8F6O2
4-(1-hydroxy-1-trifluoromethyl-2,2,2-trifluoroethyl)-2-methylphenol
—— 3-(2-(diethylamino)-1-hydroxyethyl)phenol —— C12H19NO2
3-(2-(diethylamino)-1-hydroxyethyl)phenol
—— 4-oxo-4-(5-chloro-2-hydroxy-4-methyl-phenyl)-<i>trans</i>-crotonic acid —— C11H9ClO4
4-oxo-4-(5-chloro-2-hydroxy-4-methyl-phenyl)-<i>trans</i>-crotonic acid
—— 2,4-dinitro-phenol; compound with hydrazine —— C6H4N2O5*H4N2
2,4-dinitro-phenol; compound with hydrazine
—— 3-hydroxy-2-hydroxyamino-6-nitro-benzonitrile —— C7H5N3O4
3-hydroxy-2-hydroxyamino-6-nitro-benzonitrile
—— 2-bromo-4-chloro-3-methylphenol —— C7H6BrClO
2-bromo-4-chloro-3-methylphenol
—— N-linoleoyl dopamine —— C26H41NO3
N-linoleoyl dopamine
—— 3'-O-methyl-N-oleoyl-dopamine —— C27H45NO3
3'-O-methyl-N-oleoyl-dopamine
—— 4-(4-hydroxy-3-methoxyphenyl)-but-2-enal —— C11H12O3
4-(4-hydroxy-3-methoxyphenyl)-but-2-enal
—— 3-(2,4-dihydroxyphenyl) propionaldehyde —— C9H10O3
3-(2,4-dihydroxyphenyl) propionaldehyde
—— 3-(3-hydroxy-4-methylphenyl) propionaldehyde —— C10H12O2
3-(3-hydroxy-4-methylphenyl) propionaldehyde
—— 3,5-diacetyl-2,6-dimethyl-4-(4'-hydroxyphenyl)-1,4-dihydropyridine —— C17H19NO3
3,5-diacetyl-2,6-dimethyl-4-(4'-hydroxyphenyl)-1,4-dihydropyridine
—— 5-(1-Hydroxyprop-2-en-1-yl)-2-methoxyphenol —— C10H12O3
5-(1-Hydroxyprop-2-en-1-yl)-2-methoxyphenol
—— 4-amino-2-fluoro-3-hydroxyphenylacetic acid —— C8H8FNO3
4-amino-2-fluoro-3-hydroxyphenylacetic acid
—— 3-(2-benzoylguanidino)-1-(4-hydroxybutyl)pyrazole picrate —— C6H3N3O7*C15H19N5O2
3-(2-benzoylguanidino)-1-(4-hydroxybutyl)pyrazole picrate
—— ethyl 4-amino-3-fluoro-5-hydroxyphenylacetate —— C10H12FNO3
ethyl 4-amino-3-fluoro-5-hydroxyphenylacetate
—— 4-(3-(tert-butylamino)-2-hydroxypropyl)-2-methoxyphenol —— C14H23NO3
4-(3-(tert-butylamino)-2-hydroxypropyl)-2-methoxyphenol
—— 4-(2-hydroxy-3-(phenylamino)propyl)-2-methoxyphenol —— C16H19NO3
4-(2-hydroxy-3-(phenylamino)propyl)-2-methoxyphenol
—— 4-(3-{4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl}-4,5-dihydroisoxazol-5-ylmethyl)-2-methoxyphenol —— C26H28N2O4
4-(3-{4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl}-4,5-dihydroisoxazol-5-ylmethyl)-2-methoxyphenol
—— 6-[4-(4-hydroxy-3-methoxyphenyl)but-2-enyl]-3,6-dihydropyran-2-one —— C16H18O4
6-[4-(4-hydroxy-3-methoxyphenyl)but-2-enyl]-3,6-dihydropyran-2-one
—— methyl 4-(4-hydroxy-3-methoxyphenyl)butanoate —— C12H16O4
methyl 4-(4-hydroxy-3-methoxyphenyl)butanoate
—— 4-(4-hydroxy-3-methoxyphenyl)but-2-en-1-ol —— C11H14O3
4-(4-hydroxy-3-methoxyphenyl)but-2-en-1-ol
—— ferulic acid —— C11H12O4
ferulic acid
—— 1,4-bis(3-methoxy-4-hydroxyphenyl)-but-2-ene —— C18H20O4
1,4-bis(3-methoxy-4-hydroxyphenyl)-but-2-ene
—— 2-methoxy-4-[(R)-1-oxiranylmethyl]phenol —— C10H12O3
2-methoxy-4-[(R)-1-oxiranylmethyl]phenol
—— 2-methoxy-4-[(S)-1-oxiranylmethyl]phenol —— C10H12O3
2-methoxy-4-[(S)-1-oxiranylmethyl]phenol
—— 4-(3-(1,1,1,3,5,5,5-heptamethyltrisiloxan-3-yl)propyl)-2-methoxyphenol —— C17H34O4Si3
4-(3-(1,1,1,3,5,5,5-heptamethyltrisiloxan-3-yl)propyl)-2-methoxyphenol
—— 4-allyl-2-chloro-6-methoxy-phenol —— C10H11ClO2
4-allyl-2-chloro-6-methoxy-phenol
—— 2-bromo-6-methyl-4-nitroso-phenol —— C7H6BrNO2
2-bromo-6-methyl-4-nitroso-phenol