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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
—— (3S)-1,7-bis(4'-hydroxyphenyl)-3-heptanol 30359-01-4 C19H24O3
(3S)-1,7-bis(4'-hydroxyphenyl)-3-heptanol
—— [6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,5-dihydroxy-4-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl]methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate 61303-13-7 C29H36O15
[6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,5-dihydroxy-4-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl]methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
—— cis-ε-viniferin 62218-08-0 C28H22O6
cis-ε-viniferin
—— (+)-7,8-di-epi-altholactone 124868-11-7 C13H12O4
(+)-7,8-di-epi-altholactone
—— 4-O-[β-D-xylopyranosyl]-3,3′-di-O-methylellagic acid 62218-23-9 C21H18O12
4-O-[β-D-xylopyranosyl]-3,3′-di-O-methylellagic acid
—— (3R,5R)-3,5-diacetoxy-1-(3,4-dihydroxyphenyl)-7-(4-hydroxyphenyl)heptane 1269839-26-0 C23H28O7
(3R,5R)-3,5-diacetoxy-1-(3,4-dihydroxyphenyl)-7-(4-hydroxyphenyl)heptane
—— [(2R,3R,4S,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,5-dihydroxy-4-[(3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate 61303-13-7 C29H36O15
[(2R,3R,4S,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,5-dihydroxy-4-[(3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
—— Alnusdiol 56973-51-4 C19H22O4
Alnusdiol
—— orcinol glucoside 21082-33-7 C13H18O7
orcinol glucoside
—— 2-[4-[(Z)-2-(3-hydroxy-5-methoxyphenyl)ethenyl]phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol 58762-96-2 C21H24O8
2-[4-[(Z)-2-(3-hydroxy-5-methoxyphenyl)ethenyl]phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
—— 3-Methoxy-4-prenylstilbene 64125-60-6 C20H22O
3-Methoxy-4-prenylstilbene
—— 1a-Hydroxytuberosone 95456-43-2 C20H18O6
1a-Hydroxytuberosone
—— 3-[(7R,8R)-5-hydroxy-2,2,7,8-tetramethyl-6-oxo-7,8-dihydropyrano[3,2-g]chromen-10-yl]hexanoic acid 34366-34-2 C22H28O6
3-[(7R,8R)-5-hydroxy-2,2,7,8-tetramethyl-6-oxo-7,8-dihydropyrano[3,2-g]chromen-10-yl]hexanoic acid
—— prim-O-glucosylangelicain 85889-15-2 C21H26O11
prim-O-glucosylangelicain
—— (8'Z)-5-(heptadeca-8'-enyl)benzene-1,3-diol 52483-19-9 C23H38O2
(8'Z)-5-(heptadeca-8'-enyl)benzene-1,3-diol
—— methyl 3-methoxy-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[(hydroxy)methyl]oxan-2-yl]oxy}benzoate 72500-11-9 C15H20O9
methyl 3-methoxy-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[(hydroxy)methyl]oxan-2-yl]oxy}benzoate
—— (Z)-2-(5-hydroxy-3-methoxyphenyl)-1-(4'-hydroxyphenyl)ethylene 42438-89-1 C15H14O3
(Z)-2-(5-hydroxy-3-methoxyphenyl)-1-(4'-hydroxyphenyl)ethylene
—— 2-(acetoxymethyl)-9-methoxy-6-oxo-2,3,4,4a,6,10b-hexahydropyrano[3,2-c]isochromene-3,4,8,10-tetrayl tetraacetate 14531-47-6 C24H26O14
2-(acetoxymethyl)-9-methoxy-6-oxo-2,3,4,4a,6,10b-hexahydropyrano[3,2-c]isochromene-3,4,8,10-tetrayl tetraacetate
—— chlorogenic acid 327-97-9 C16H18O9
chlorogenic acid
—— neochlorogenic acid 327-97-9 C16H18O9
neochlorogenic acid
—— 3‐caffeoylquinic acid 327-97-9 C16H18O9
3‐caffeoylquinic acid
—— caffeoylquinic acid 327-97-9 C16H18O9
caffeoylquinic acid
—— cis-3-caffeoylquinic acid 327-97-9 C16H18O9
cis-3-caffeoylquinic acid
—— 3-O-caffeoylqunic acid 327-97-9 C16H18O9
3-O-caffeoylqunic acid
—— (1<i>R</i>)-3<i>c</i>-[3<i>c</i>-(3,4-dihydroxy-phenyl)-acryloyloxy]-1,4<i>t</i>,5<i>t</i>-trihydroxy-cyclohexane-<i>r</i>-carboxylic acid 327-97-9 C16H18O9
(1<i>R</i>)-3<i>c</i>-[3<i>c</i>-(3,4-dihydroxy-phenyl)-acryloyloxy]-1,4<i>t</i>,5<i>t</i>-trihydroxy-cyclohexane-<i>r</i>-carboxylic acid
—— 4-O-galloylbergenin 82958-45-0 C21H20O13
4-O-galloylbergenin
—— 4-[5-(4-Hydroxy-3-methoxyphenyl)penta-1,4-dien-1-YL]-2-methoxyphenol 63644-68-8 C19H20O4
4-[5-(4-Hydroxy-3-methoxyphenyl)penta-1,4-dien-1-YL]-2-methoxyphenol
—— nordihydroguairetic acid 27686-84-6 C18H22O4
nordihydroguairetic acid
—— trans-δ-viniferin 62218-13-7 C28H22O6
trans-δ-viniferin
—— (+)-E-ε-viniferin 62218-08-0 C28H22O6
(+)-E-ε-viniferin
—— (+)-usnic acid 7562-61-0 C18H16O7
(+)-usnic acid
—— (+)-usnic acid 7562-61-0 C18H16O7
(+)-usnic acid
—— geraniin 60976-49-0 C41H28O27
geraniin
—— (5S)-1,7-bis(4-hydroxyphenyl)-5-hydroxyheptan-3-one 41137-85-3 C19H22O4
(5S)-1,7-bis(4-hydroxyphenyl)-5-hydroxyheptan-3-one
—— 2-hydroxy-3,8-dimethoxy-7-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)chromeno[5,4,3-cde]chromene-5,10-dione 51803-68-0 C22H20O13
2-hydroxy-3,8-dimethoxy-7-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)chromeno[5,4,3-cde]chromene-5,10-dione
—— 3,3'-di-O-methylellagic acid 4-O-glucoside 51803-68-0 C22H20O13
3,3'-di-O-methylellagic acid 4-O-glucoside
—— 5-(6-Hydroxy-1-benzofuran-2-yl)-2-(5-hydroxy-9-methyl-8-oxatricyclo[7.3.1.02,7]trideca-2(7),3,5,10-tetraen-11-yl)benzene-1,3-diol 89199-99-5 C27H22O6
5-(6-Hydroxy-1-benzofuran-2-yl)-2-(5-hydroxy-9-methyl-8-oxatricyclo[7.3.1.02,7]trideca-2(7),3,5,10-tetraen-11-yl)benzene-1,3-diol
—— 2,2'-Methylenebis(6-acetyl-3,5-dihydroxy-4,4-dimethyl-2,5-cyclohe xadien-1-one) 3570-40-9 C21H24O8
2,2'-Methylenebis(6-acetyl-3,5-dihydroxy-4,4-dimethyl-2,5-cyclohe xadien-1-one)
—— 3,6a-Dihydroxy-9-methoxy-10-prenylpterocarpan 74515-47-2 C21H22O5
3,6a-Dihydroxy-9-methoxy-10-prenylpterocarpan
—— (+/-)-5-hydroxy-1,7-bis-(4'-hydroxyphenyl)-3-heptanone 41137-85-3 C19H22O4
(+/-)-5-hydroxy-1,7-bis-(4'-hydroxyphenyl)-3-heptanone
—— Sakakin 21082-33-7 C13H18O7
Sakakin
—— 3,9-Dihydroxy-1-methoxy-10-prenylpterocarpan 65428-13-9 C21H22O5
3,9-Dihydroxy-1-methoxy-10-prenylpterocarpan
—— usnic acid 15853-98-2 C18H16O7
usnic acid
—— (-)-Maackiain 3-O-glucoside 6807-83-6 C22H22O10
(-)-Maackiain 3-O-glucoside
—— 8,15-Dihydroxy-3,16,17-trimethoxytricyclo[12.3.1.12,6]nonadeca-1(17),2,4,6(19),14(18),15-hexaen-9-one 56222-03-8 C22H26O6
8,15-Dihydroxy-3,16,17-trimethoxytricyclo[12.3.1.12,6]nonadeca-1(17),2,4,6(19),14(18),15-hexaen-9-one
—— Confluentinsaeure 6009-12-7 C28H36O8
Confluentinsaeure
—— 6a-Hydroxymedicarpin 61135-92-0 C16H14O5
6a-Hydroxymedicarpin
—— 3,7-Dihydroxy-15,16,17-trimethoxytricyclo[12.3.1.1~2,6~]nonadeca-1(18),2(19),3,5,14,16-hexaen-9-one 56222-03-8 C22H26O6
3,7-Dihydroxy-15,16,17-trimethoxytricyclo[12.3.1.1~2,6~]nonadeca-1(18),2(19),3,5,14,16-hexaen-9-one
—— 2-(Hydroxymethyl)-6-[4-(hydroxymethyl)-2,6-dimethoxyphenoxy]oxane-3,4,5-triol 64121-98-8 C15H22O9
2-(Hydroxymethyl)-6-[4-(hydroxymethyl)-2,6-dimethoxyphenoxy]oxane-3,4,5-triol
—— (4E,6E)-1,7-bis(4-hydroxyphenyl)-4,6-heptadien-3-one 332371-82-1 C19H18O3
(4E,6E)-1,7-bis(4-hydroxyphenyl)-4,6-heptadien-3-one