原儿茶酸(PCA)即3,4-二羟基苯甲酸,是一种简单的酚酸。它是合成其他复杂分子的前体,例如花青素 3-O-β-D-葡萄糖苷和香兰素。这种物质存在于多种可食用的植物中,包括蔬菜、水果、坚果、糙米、山核桃、茶叶、木槿花以及一些中草药。
原儿茶酸针对不同的分子靶点具有多种多样的生物活性。它能够发挥抗菌、抗氧化、抗炎、抗高血糖和神经保护等作用,并且具有潜在的化学防护功能,能够抑制体外的化学致癌物质以及在不同方面产生促凋亡和抗增殖的作用。目前,原儿茶酸已在临床上用于治疗烧伤、小儿肺炎、菌痢、急性肾盂肾炎、急性胰腺炎及某些溃疡病。
药理作用原儿茶酸是复杂多酚类的代谢产物,在植物和水果中含量很高。它们能够被动物和人类吸收,据估算,人们每天摄入的花青素比其他多酚类要高得多。因此,原儿茶酸的营养价值逐渐得到认可。
功效与作用研究已证实,原儿茶酸具有抗菌、抗氧化、抗炎、抗高血糖以及神经保护等多种生物活性,并且能够抑制体外的化学致癌物质,在不同方面产生促凋亡和抗增殖的作用。
制备方法采用胡椒醛作原料制备原儿茶酸。首先将12 g胡椒醛与300 ml水加入到1000 ml三颈瓶中,加热至70~80℃,剧烈搅拌下滴加5%的高锰酸钾溶液(18 g高锰酸钾加360 ml水),约30 min后继续搅拌至紫色褪去。趁热过滤、洗涤滤饼,并母液酸化得到胡椒酸。再将4 g三氯化铝加入到150 ml硝基苯中,搅拌溶解并分批加入10 g胡椒酸,在室温下搅拌3~5小时。反应液倒入100 ml水中分离水层,向该水溶液通入二氧化硫析出原儿茶酸,总收率为81%,熔点200~201℃。
提取方法从紫丁香叶中提取原儿茶酸的方法如下:
(1)样品前处理:将干燥、去杂后的紫丁香叶片通过粉碎机粉碎成细粉。 (2)原儿茶酸的提取:称取过40目筛的紫丁香叶片粉末2.0 g,在设定工艺条件下以无水乙醇为提取剂进行提取。滤过后弃去药渣,回收乙醇得粗提物。将粗提物与50 ml乙醚和3 ml 0.1 mol/L盐酸振摇溶解,转入分液漏斗中,用0.1 mol/L氢氧化钠溶液分次(每次50 ml)提取3次。洗涤后的氢氧化钠溶液分别用10 ml乙醚洗涤并合并后加入3 ml 1 mol/L盐酸,再用水重复提取3次。将三次提取的乙醚层分别用水洗涤,合并后调pH值为6.0并蒸干得几近白色的粉末状晶体。
化学性质原儿茶酸呈白色至微棕色针状结晶状,熔点约200℃(分解)。它溶于热水、乙醇和乙醚,微溶于冷水而不溶于苯。在沸水中会分解并放出二氧化碳。水溶液遇三氯化铁呈绿色,遇碳酸氢钠则呈暗红色。
用途原儿茶酸可用作染料、医药的中间体以及分析试剂(检定铁)。此外,它还适用于体内研究4-香豆酸和3,4-二羟基苯甲酸对大鼠结肠黏膜基础氧化性DNA损伤的影响,并可用于壳聚糖树脂的衍生化。原儿茶酸也可由香草醛经碱熔、酸化而得。
生产方法原儿茶酸可通过香草醛经碱熔、酸化制备得到。
中文名称 | 英文名称 | CAS号 | 化学式 | 分子量 |
---|---|---|---|---|
3-羟基-4-甲氧基苯甲酸 | Isovanillic acid | 645-08-9 | C8H8O4 | 168.149 |
香草酸 | 3-methoxy-4-hydroxybenzoic acid | 121-34-6 | C8H8O4 | 168.149 |
间羟基苯甲酸 | 3-Carboxyphenol | 99-06-9 | C7H6O3 | 138.123 |
3,4-二羟基苯甲酸乙酯 | Ethyl protocatechuate | 3943-89-3 | C9H10O4 | 182.176 |
藜芦酸 | Veratric acid | 93-07-2 | C9H10O4 | 182.176 |
3-羟基-4-甲氧基苯甲酸甲酯 | 3-hydroxy-4-methoxybenzoate | 6702-50-7 | C9H10O4 | 182.176 |
3,4-二羟基苄醇 | 4-(hydroxymethyl)benzene-1,2-diol | 3897-89-0 | C7H8O3 | 140.139 |
香草酸甲酯 | 4-hydroxy-3-methoxybenzoic acid methyl ester | 3943-74-6 | C9H10O4 | 182.176 |
3,4-二羟基苯甲醛 | 3,4-dihydroxybenzaldehyde | 139-85-5 | C7H6O3 | 138.123 |
4-乙氧基-3-甲氧基苯甲酸 | 4-ethoxy-3-methoxybenzoic acid | 3535-30-6 | C10H12O4 | 196.203 |
3-甲氧基苯甲酸 | 3-Methoxybenzoic acid | 586-38-9 | C8H8O3 | 152.15 |
对羟基苯甲酸 | 4-hydroxy-benzoic acid | 99-96-7 | C7H6O3 | 138.123 |
胡椒酸 | Piperonylic acid | 94-53-1 | C8H6O4 | 166.133 |
2,3-二氢-1,4-苯并二噁烷-6-羧酸 | 2,3-dihydro-1,4-benzodioxin-6-carboxylic acid | 4442-54-0 | C9H8O4 | 180.16 |
4-甲酰-3-羟基苯甲酸 | 4-formyl-3-hydroxybenzoic acid | 619-12-5 | C8H6O4 | 166.133 |
大茴香酸 | 4-methoxybenzoic acid | 100-09-4 | C8H8O3 | 152.15 |
香草醛 | vanillin | 121-33-5 | C8H8O3 | 152.15 |
3-羟基-4-溴苯甲酸 | 4-bromo-3-hydroxybenzoic acid | 14348-38-0 | C7H5BrO3 | 217.019 |
4,5-二甲氧基邻苯二甲酸 | m-hemipinic acid | 577-68-4 | C10H10O6 | 226.186 |
—— | aristelegin-C | 24724-87-6 | C15H12O6 | 288.257 |
3,4-二乙酰氧基苯甲酸 | 3,4-Diacetoxy-benzoesaeure | 58534-64-8 | C11H10O6 | 238.197 |
4-乙氧基-3-羟基苯甲醛 | 4-ethoxy-3-hydroxybenzaldehyde | 2539-53-9 | C9H10O3 | 166.177 |
过氧化氢酶 | Ethyl 4-hydroxybenzoate | 120-47-8 | C9H10O3 | 166.177 |
对羟基苯甲酸苄酯 | Benzyl 4-hydroxybenzoate | 94-18-8 | C14H12O3 | 228.247 |
胡椒醇 | piperonol | 495-76-1 | C8H8O3 | 152.15 |
胡椒醛 | piperonal | 120-57-0 | C8H6O3 | 150.134 |
中文名称 | 英文名称 | CAS号 | 化学式 | 分子量 |
---|---|---|---|---|
没食子酸 | 3,4,5-trihydroxybenzoic acid | 149-91-7 | C7H6O5 | 170.122 |
3,4-二羟基苯甲酸甲酯 | 3,4-dihydroxybenzoic acid methyl ester | 2150-43-8 | C8H8O4 | 168.149 |
3-羟基-4-甲氧基苯甲酸 | Isovanillic acid | 645-08-9 | C8H8O4 | 168.149 |
没食子酸甲酯 | methyl galloate | 99-24-1 | C8H8O5 | 184.149 |
香草酸 | 3-methoxy-4-hydroxybenzoic acid | 121-34-6 | C8H8O4 | 168.149 |
3,4-二羟基苯甲酸乙酯 | Ethyl protocatechuate | 3943-89-3 | C9H10O4 | 182.176 |
—— | 4-ethoxy-3-hydroxy-benzoic acid | 90536-50-8 | C9H10O4 | 182.176 |
藜芦酸 | Veratric acid | 93-07-2 | C9H10O4 | 182.176 |
—— | benzyl 3,4-dihydroxybenzoate | 80003-86-7 | C14H12O4 | 244.247 |
原儿茶酸异丙酯 | protocatechuic acid i-propyl ester | 105603-53-0 | C10H12O4 | 196.203 |
—— | allyl 3,4-dihydroxybenzoate | 93506-73-1 | C10H10O4 | 194.187 |
3-羟基-4-甲氧基苯甲酸甲酯 | 3-hydroxy-4-methoxybenzoate | 6702-50-7 | C9H10O4 | 182.176 |
—— | propyl 3,4-dihydroxybenzoate | 37757-42-9 | C10H12O4 | 196.203 |
—— | propargyl 3,4-dihydroxybenzoate | —— | C10H8O4 | 192.171 |
—— | 3,4-dihydroxy-benzoic acid-(2-methoxy-ethyl ester) | —— | C10H12O5 | 212.202 |
2-甲基-2-丙基3,4-二羟基苯甲酸酯 | 3,4-Dihydroxy-benzoic acid tert-butyl ester | 760947-24-8 | C11H14O4 | 210.23 |
—— | 3,4-dihydroxybenzoic anhydride | 1037309-72-0 | C14H10O7 | 290.229 |
3,4-二羟基苄醇 | 4-(hydroxymethyl)benzene-1,2-diol | 3897-89-0 | C7H8O3 | 140.139 |
原儿茶酸异丁酯 | protocatechuic acid i-butyl ester | 105603-54-1 | C11H14O4 | 210.23 |
3-乙氧基-4-羟基-苯甲酸 | 3-ethoxy 4-hydroxy benzoic acid | 5438-38-0 | C9H10O4 | 182.176 |
—— | butyl protocatechuate | 37622-53-0 | C11H14O4 | 210.23 |
3,4-二羟基苯甲醛 | 3,4-dihydroxybenzaldehyde | 139-85-5 | C7H6O3 | 138.123 |
—— | (3,4-dihydroxybenzoyloxy)acetic acid | —— | C9H8O6 | 212.159 |
—— | pentyl 3,4-dihydroxybenzoate | 37622-54-1 | C12H16O4 | 224.257 |
—— | 3-methylbenzyl 3',4'-dihydroxybenzoate | 1070881-36-5 | C15H14O4 | 258.274 |
3,5-二羟基苯甲酸甲酯 | 1-carbomethoxy-3,5-dihydroxybenzene | 2150-44-9 | C8H8O4 | 168.149 |
—— | hexyl 3,4-dihydroxybenzoate | —— | C13H18O4 | 238.284 |
3,4-二甲氧基苯甲酸甲酯 | methyl 3,4-dimethoxybenzoate | 2150-38-1 | C10H12O4 | 196.203 |
—— | 6-(3,4-dihydroxy-benzoyl)oxyhexyl-3,4-dihydroxy-benzoate | 1234569-85-7 | C20H22O8 | 390.39 |
—— | heptyl protocatechuate | —— | C14H20O4 | 252.31 |
—— | 7-(3,4-dihydroxy-benzoyl)oxyheptyl-3,4-dihydroxy-benzoate | 1234569-88-0 | C21H24O8 | 404.417 |
—— | 3-(allyloxy)-4-hydroxybenzoic acid | —— | C10H10O4 | 194.187 |
—— | dodecyl protocatechuate | 80003-85-6 | C19H30O4 | 322.445 |
—— | hexadecyl protocatechuate | 31086-05-2 | C23H38O4 | 378.552 |
—— | nonyl 3,4-dihydroxybenzoate | —— | C16H24O4 | 280.364 |
—— | undecyl 3,4-dihydroxybenzoate | —— | C18H28O4 | 308.418 |
3,4-二羟基苯甲酸辛酯 | octyl 3,4-dihydroxybenzoate | 1152-47-2 | C15H22O4 | 266.337 |
—— | n-decyl-3,4-dihydroxybenzoate | 105603-52-9 | C17H26O4 | 294.391 |
—— | tetradecyl protocatechuate | —— | C21H34O4 | 350.499 |
—— | tridecyl 3,4-dihydroxybenzoate | —— | C20H32O4 | 336.472 |
—— | octadecyl protocatechuate | 31086-04-1 | C25H42O4 | 406.606 |
—— | 9-(3,4-dihydroxy-benzoyl)oxynonyl-3,4-dihydroxy-benzoate | 1234569-90-4 | C23H28O8 | 432.471 |
胡椒酸 | Piperonylic acid | 94-53-1 | C8H6O4 | 166.133 |
3,4-二乙氧基苯甲酸 | 3,4-diethoxybenzoic acid | 5409-31-4 | C11H14O4 | 210.23 |
—— | 3,4-dihydroxy-benzoic acid phenyl ester | 36081-00-2 | C13H10O4 | 230.22 |
—— | cis-2-nonen-1-yl 3,4-dihydroxybenzoate | —— | C16H22O4 | 278.348 |
—— | trans-2-nonen-1-yl 3,4-dihydroxybenzoate | —— | C16H22O4 | 278.348 |
—— | (3,4-dihydroxybenzoyloxy)acetic acid methyl ester | —— | C10H10O6 | 226.186 |
—— | 3,4-dihydroxy-benzoic acid-(2-ethyl-butyl ester) | 5438-57-3 | C13H18O4 | 238.284 |
—— | phenethyl 3,4-dihydroxybenzoate | 100981-80-4 | C15H14O4 | 258.274 |
3-溴-4,5-二羟基苯甲酸 | 3-bromo-4,5-dihydroxybenzoic acid | 61203-46-1 | C7H5BrO4 | 233.018 |
3,4-二甲氧基苯甲酸乙酯 | ethyl veratrate | 3943-77-9 | C11H14O4 | 210.23 |
—— | 3,4-dihydroxy-benzoic acid-(2,3-dichloro-propyl ester) | 5438-43-7 | C10H10Cl2O4 | 265.093 |
—— | 3,4-bis(methoxymethoxy)benzoic acid | 149220-87-1 | C11H14O6 | 242.229 |
—— | 3,4-dipropoxybenzoic acid | 794582-28-8 | C13H18O4 | 238.284 |
—— | methyl 4-butyloxy-3-hydroxybenzoate | 849029-93-2 | C12H16O4 | 224.257 |
2,3-二氢-1,4-苯并二噁烷-6-羧酸 | 2,3-dihydro-1,4-benzodioxin-6-carboxylic acid | 4442-54-0 | C9H8O4 | 180.16 |
—— | 3,4-dihydroxy-benzoic acid-(2-phenoxy-ethyl ester) | —— | C15H14O5 | 274.273 |
—— | 3,4-(bis-allyloxy)benzoic acid allyl ester | 664334-20-7 | C13H14O4 | 234.252 |
—— | 3-phenylpropyl 3,4-dihydroxybenzoate | 1425795-77-2 | C16H16O4 | 272.301 |
—— | 3,4-bis(prop-2-yn-1-yloxy)benzoic acid | 766509-48-2 | C13H10O4 | 230.22 |
3-乙酰氧基-4-羟基-苯甲酸 | 3-acetoxy-4-hydroxy-benzoic acid | 104056-02-2 | C9H8O5 | 196.16 |
4-(苄氧基)-3-羟基苯甲酸甲酯 | methyl 4-(benzyloxy)-3-hydroxybenzoate | 87687-75-0 | C15H14O4 | 258.274 |
3,4,5-三甲氧基苯甲酸甲酯 | 3,4,5-trimethoxybenzoic acid methyl ester | 1916-07-0 | C11H14O5 | 226.229 |
—— | geranyl 3,4-dihydroxybenzoate | —— | C17H22O4 | 290.359 |
—— | neryl 3,4-dihydroxybenzoate | —— | C17H22O4 | 290.359 |
—— | methyl 3-(allyloxy)-4-hydroxybenzoate | —— | C11H12O4 | 208.214 |
—— | 3,4-dibutoxy-benzoic acid | 206536-14-3 | C15H22O4 | 266.337 |
—— | cyclohexmethyl 3,4-dihydroxybenzoate | —— | C14H18O4 | 250.295 |
甲基 1,3-苯并二恶唑-5-羧酸酯 | methyl 3,4-methylenedioxybenzoate | 326-56-7 | C9H8O4 | 180.16 |
—— | 2-nonanyl 3,4-dihydroxybenzoate | —— | C16H24O4 | 280.364 |
—— | 3,4-dihydroxyphenethyl 3,4-dihydroxybenzoate | 1227465-31-7 | C15H14O6 | 290.273 |
3-甲氧基苯甲酸甲酯 | methyl 3-methoxybenzoate | 5368-81-0 | C9H10O3 | 166.177 |
3-羟基-4-磺基氧基苯甲酸 | 3-hydroxybenzoic acid-4-sulfate | 76496-12-3 | C7H6O7S | 234.186 |
阿考替胺杂质39 | 4,5-dihydroxy-2-methoxybenzoic acid | 27867-46-5 | C8H8O5 | 184.149 |
—— | 3-Ethoxy-4-hexoxybenzoic acid | 938342-71-3 | C15H22O4 | 266.337 |
—— | 3,4-bis-pentyloxy-benzoic acid | 179166-72-4 | C17H26O4 | 294.391 |
3,4-二(苄氧基)苯甲酸 | 3,4-bis(benzyloxy)benzoic acid | 1570-05-4 | C21H18O4 | 334.372 |
—— | 3,4-Dihexyloxybenzoic acid | 121925-05-1 | C19H30O4 | 322.445 |
—— | methyl 3-butoxy-4-hydroxybenzoate | 484018-40-8 | C12H16O4 | 224.257 |
—— | 3,4-bis(isopentyloxy)benzoic acid | —— | C17H26O4 | 294.391 |
—— | 3,4-bis(4-Methoxybenzyloxy)benzoic acid | 134368-28-8 | C23H22O6 | 394.424 |
—— | 3,4-bis(heptyloxy)benzoic acid | 131525-55-8 | C21H34O4 | 350.499 |
苯甲酸,3,4-二(十二烷氧基)- | 3,4-didodecyloxybenzoic acid | 131525-58-1 | C31H54O4 | 490.767 |
—— | 3,4-Didecyloxybenzoic acid | 120878-42-4 | C27H46O4 | 434.66 |
—— | 3,4-dioctyloxybenzoic acid | 131525-56-9 | C23H38O4 | 378.552 |
—— | 3,4-Dinonyloxybenzoic acid | 131525-57-0 | C25H42O4 | 406.606 |
—— | 3,4-bis(tetradecyloxy)benzoic acid | 131525-60-5 | C35H62O4 | 546.875 |
苯甲酸,3,4-二(十六烷氧基)- | 3,4-Dihexadecyloxybenzoic acid | 180678-33-5 | C39H70O4 | 602.982 |
—— | 3,4-dihydroxy-benzoic acid-(2-phenylseleno-ethyl ester) | —— | C15H14O4Se | 337.234 |
—— | 3-nonanyl 3,4-dihydroxybenzoate | —— | C16H24O4 | 280.364 |
4-苄氧基-3-羟基苯甲酸乙酯 | ethyl 4-benzyloxy-3-hydroxybenzoate | 177429-27-5 | C16H16O4 | 272.301 |
—— | 3-bromo-4,5-dihydroxybenzoic acid methyl ester | 65841-10-3 | C8H7BrO4 | 247.045 |
3,4-二甲氧基苄醇 | (3,4-dimethoxyphenyl)methanol | 93-03-8 | C9H12O3 | 168.192 |
苯并二氧六环-6-甲酸甲酯 | 2,3-dihydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester | 20197-75-5 | C10H10O4 | 194.187 |
3,5-二甲氧基苯甲酸甲酯 | methyl 3,5-dimethoxybenzoate | 2150-37-0 | C10H12O4 | 196.203 |
3,4-二乙氧基苯甲酸乙酯 | 3,4-diethoxybenzoic acid ethyl ester | 75332-44-4 | C13H18O4 | 238.284 |
—— | methyl 3,4-bis(allyloxy)benzoate | —— | C14H16O4 | 248.279 |
3-(环丙基甲氧基)-4-羟基苯甲酸甲酯 | methyl 3-(cyclopropylmethoxy)-4-hydroxybenzoate | 848574-60-7 | C12H14O4 | 222.241 |
—— | methyl 3,4-dihydro-2H-benzo[b][1,4]dioxepine-7-carboxylate | 773876-04-3 | C11H12O4 | 208.214 |