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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
—— (1,6-dihydroxy-4-methoxymethyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid 1265355-37-0 C11H13BO6
(1,6-dihydroxy-4-methoxymethyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid
—— 4-methoxy-3,5-bis(phenoxymethyl)phenol 848360-66-7 C21H20O4
4-methoxy-3,5-bis(phenoxymethyl)phenol
—— 28-Bromo-3,6,9,12,15,18,21,24-octaoxabicyclo[24.3.1]triaconta-1(29),26(30),27-trien-30-ol 946533-35-3 C22H35BrO9
28-Bromo-3,6,9,12,15,18,21,24-octaoxabicyclo[24.3.1]triaconta-1(29),26(30),27-trien-30-ol
—— (5S,13S)-21-hydroxy-5,13-diphenyl-3,6,9,12,15-pentaoxabicyclo[15.3.1]henicosa-1(20),17(21),18-triene 497107-22-9 C28H32O6
(5S,13S)-21-hydroxy-5,13-diphenyl-3,6,9,12,15-pentaoxabicyclo[15.3.1]henicosa-1(20),17(21),18-triene
—— ethyl 3-(3-hydroxy-5-methoxyphenyl)propanoate 628330-10-9 C12H16O4
ethyl 3-(3-hydroxy-5-methoxyphenyl)propanoate
—— (4S,14S)-4,14-diphenyl-3,6,9,12,15-pentaoxabicyclo[15.3.1]henicosa-1(21),17,19-trien-21-ol 189451-75-0 C28H32O6
(4S,14S)-4,14-diphenyl-3,6,9,12,15-pentaoxabicyclo[15.3.1]henicosa-1(21),17,19-trien-21-ol
—— (4S,14S)-19-bromo-4,14-diphenyl-3,6,9,12,15-pentaoxabicyclo[15.3.1]henicosa-1(20),17(21),18-trien-21-ol 189451-74-9 C28H31BrO6
(4S,14S)-19-bromo-4,14-diphenyl-3,6,9,12,15-pentaoxabicyclo[15.3.1]henicosa-1(20),17(21),18-trien-21-ol
—— 4-<<(S)-6-methyloctyl>oxy>phenol 114243-83-3 C15H24O2
4-<<(S)-6-methyloctyl>oxy>phenol
—— 22-Bromo-3,6,9,12,15,18-hexaoxabicyclo[18.3.1]tetracosa-1(23),20(24),21-trien-24-ol 946533-31-9 C18H27BrO7
22-Bromo-3,6,9,12,15,18-hexaoxabicyclo[18.3.1]tetracosa-1(23),20(24),21-trien-24-ol
—— 2,3,5‐trihydroxybenzaldehyde 74186-01-9 C7H6O4
2,3,5‐trihydroxybenzaldehyde
—— 4-(2-hydroxyethyl)-2-methoxyphenol acetate 1220703-45-6 C11H14O4
4-(2-hydroxyethyl)-2-methoxyphenol acetate
—— 5,5'-((1E,3E,5E)-hexa-1,3,5-triene-1,6-diyl)dibenzene-1,3-diol 1443299-34-0 C18H16O4
5,5'-((1E,3E,5E)-hexa-1,3,5-triene-1,6-diyl)dibenzene-1,3-diol
—— 1,3-dihydroxy-5-[(Z)-non-2'-enyl]benzene 253158-28-0 C15H22O2
1,3-dihydroxy-5-[(Z)-non-2'-enyl]benzene
—— N-[2-[[2-(3,5-dihydroxyphenyl)-2-hydroxyethyl]amino]ethyl]-2-methylpropanamide 56443-27-7 C14H22N2O4
N-[2-[[2-(3,5-dihydroxyphenyl)-2-hydroxyethyl]amino]ethyl]-2-methylpropanamide
—— 4-hydroxyphenylacetaldoxime 70365-12-7 C8H9NO2
4-hydroxyphenylacetaldoxime
—— p-hydroxyphenylacetaldehyde oxime 70365-10-5 C8H9NO2
p-hydroxyphenylacetaldehyde oxime
—— 2,5-di(cyclohex-1-en-3-yl)benzene-1,4-diol 1207096-42-1 C18H22O2
2,5-di(cyclohex-1-en-3-yl)benzene-1,4-diol
—— 5-((2S,3S,6R,8R,9S,11S)-8-(cyclohexylmethyl)-3,9,11-trimethyl-1,7-dioxaspiro[5.5]undecan-2-yl) benzene-1,3-diol 1297531-41-9 C25H38O4
5-((2S,3S,6R,8R,9S,11S)-8-(cyclohexylmethyl)-3,9,11-trimethyl-1,7-dioxaspiro[5.5]undecan-2-yl) benzene-1,3-diol
—— AG 83 118409-64-6 C10H6N2O2
AG 83
—— 4-[3-(1-hydroxy-2-piperidin-1-yl-ethyl)-isoxazol-5-yl]-phenol 53983-89-4 C16H20N2O3
4-[3-(1-hydroxy-2-piperidin-1-yl-ethyl)-isoxazol-5-yl]-phenol
—— 3-((3,5-dimethylphenylimino)methyl)benzene-1,2-diol 303769-54-2 C15H15NO2
3-((3,5-dimethylphenylimino)methyl)benzene-1,2-diol
—— 2-amino-2-(3,5-dihydroxyphenyl)acetonitrile 1208237-23-3 C8H8N2O2
2-amino-2-(3,5-dihydroxyphenyl)acetonitrile
—— 4-(1-Azido-3,3,3-trifluoropropyl)phenol 1602485-00-6 C9H8F3N3O
4-(1-Azido-3,3,3-trifluoropropyl)phenol
—— 2-hydroxy-5-methoxy-phenylacetonitrile 33901-23-4 C9H9NO2
2-hydroxy-5-methoxy-phenylacetonitrile
—— (Z)-5-(3,5-dihydroxybenzylidene)thiazolidine-2,4-dione 1362738-30-4 C10H7NO4S
(Z)-5-(3,5-dihydroxybenzylidene)thiazolidine-2,4-dione
—— 1-(3,4-dihydroxyphenyl)-2-(β-isobutyramidoethyl)aminoethanol 56443-18-6 C14H22N2O4
1-(3,4-dihydroxyphenyl)-2-(β-isobutyramidoethyl)aminoethanol
—— N-[2-[[3-(3,5-dihydroxyphenoxy)-2-hydroxypropyl]amino]ethyl]-2-methylpropanamide 76167-02-7 C15H24N2O5
N-[2-[[3-(3,5-dihydroxyphenoxy)-2-hydroxypropyl]amino]ethyl]-2-methylpropanamide
—— N-<2-<<2-hydroxy-2-(3-hydroxyphenyl)ethyl>amino>ethyl>-2-methylpropanamide 56443-16-4 C14H22N2O3
N-<2-<<2-hydroxy-2-(3-hydroxyphenyl)ethyl>amino>ethyl>-2-methylpropanamide
—— β-(3,4-dihydroxyphenyl)propionamide 1132-49-6 C9H11NO3
β-(3,4-dihydroxyphenyl)propionamide
—— Isosyringaalkohol 102370-08-1 C9H12O4
Isosyringaalkohol
—— (R)-(+)-4-hydroxyphenyloxirane 1176829-46-1 C8H8O2
(R)-(+)-4-hydroxyphenyloxirane
—— 2-ethyl-4-methyl-resorcinol 412018-53-2 C9H12O2
2-ethyl-4-methyl-resorcinol
—— (R,S)-2-cyano-3-(4-hydroxy-2',6'-dimethylphenyl)-propanoic acid ethyl ester 254102-29-9 C14H17NO3
(R,S)-2-cyano-3-(4-hydroxy-2',6'-dimethylphenyl)-propanoic acid ethyl ester
—— Phenol, 2-[2-[(1,1-dimethylethyl)sulfinyl]ethyl]- 62296-39-3 C12H18O2S
Phenol, 2-[2-[(1,1-dimethylethyl)sulfinyl]ethyl]-
—— N-[2-[3,5-bis(phenylmethoxy)phenyl]ethyl]-3-(3,4-dihydroxyphenyl)propanamide 188662-16-0 C31H31NO5
N-[2-[3,5-bis(phenylmethoxy)phenyl]ethyl]-3-(3,4-dihydroxyphenyl)propanamide
—— 4-(3,6,9,12-tetraoxatridec-1-yloxy)phenol 845910-52-3 C15H24O6
4-(3,6,9,12-tetraoxatridec-1-yloxy)phenol
—— trans-N-n-Hexyl-β-(3,4-dihydroxyphenoxy)acrylamide 136944-37-1 C15H21NO4
trans-N-n-Hexyl-β-(3,4-dihydroxyphenoxy)acrylamide
—— 4-[4-(4-Methoxyphenyl)-1,2-oxazol-5-yl]benzene-1,2-diol 1271728-03-0 C16H13NO4
4-[4-(4-Methoxyphenyl)-1,2-oxazol-5-yl]benzene-1,2-diol
—— 4-(2-phosphonoethyl)catechol 1194473-18-1 C8H11O5P
4-(2-phosphonoethyl)catechol
—— 3,4,4'-trihydroxypulvinone 131146-40-2 C17H12O6
3,4,4'-trihydroxypulvinone
—— danshensu isopropyl ester 950665-05-1 C12H16O5
danshensu isopropyl ester
—— (S)-isopropyl 2-hydroxy-3-(3,4-dihydroxyphenyl)propanoate 1280727-98-1 C12H16O5
(S)-isopropyl 2-hydroxy-3-(3,4-dihydroxyphenyl)propanoate
—— 4,5-dibenzyloxy-2-dimethylaminomethylphenol 157259-31-9 C23H25NO3
4,5-dibenzyloxy-2-dimethylaminomethylphenol
—— [4-(3,4-dihydrophenyl)-3-hydroxy-5-oxo-5H-furan-2-ylidene](4-hydroxyphenyl)acetic acid 25287-88-1 C18H12O8
[4-(3,4-dihydrophenyl)-3-hydroxy-5-oxo-5H-furan-2-ylidene](4-hydroxyphenyl)acetic acid
—— 4-nonylcatechol 123063-35-4 C15H24O2
4-nonylcatechol
—— 4-n-Tridecyl-brenzkatechin 78844-07-2 C19H32O2
4-n-Tridecyl-brenzkatechin
—— 2-[2-[4-Methoxy-2,6-bis(phenylmethoxy)phenyl]ethynyl]-4,5-bis(phenylmethoxy)phenol 344303-12-4 C43H36O6
2-[2-[4-Methoxy-2,6-bis(phenylmethoxy)phenyl]ethynyl]-4,5-bis(phenylmethoxy)phenol
—— 3-bromo-4-propoxyphenol 191983-34-3 C9H11BrO2
3-bromo-4-propoxyphenol
—— 2-amino-6-{[3-(4-hydroxyphenoxy)propyl]amino}-5-nitroso-4(3H)-pyrimidinone 100840-75-3 C13H15N5O4
2-amino-6-{[3-(4-hydroxyphenoxy)propyl]amino}-5-nitroso-4(3H)-pyrimidinone
—— 2-Methoxy-5-(propan-2-YL)phenol 499-79-6 C10H14O2
2-Methoxy-5-(propan-2-YL)phenol