CN115850228A - Egcg晶型i的制备方法 - Google Patents
Egcg晶型i的制备方法 Download PDFInfo
- Publication number
- CN115850228A CN115850228A CN202211625707.2A CN202211625707A CN115850228A CN 115850228 A CN115850228 A CN 115850228A CN 202211625707 A CN202211625707 A CN 202211625707A CN 115850228 A CN115850228 A CN 115850228A
- Authority
- CN
- China
- Prior art keywords
- egcg
- eluent
- crystal form
- preparation
- green tea
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- WMBWREPUVVBILR-WIYYLYMNSA-N (-)-Epigallocatechin-3-o-gallate Chemical compound O([C@@H]1CC2=C(O)C=C(C=C2O[C@@H]1C=1C=C(O)C(O)=C(O)C=1)O)C(=O)C1=CC(O)=C(O)C(O)=C1 WMBWREPUVVBILR-WIYYLYMNSA-N 0.000 title claims abstract description 48
- WMBWREPUVVBILR-UHFFFAOYSA-N GCG Natural products C=1C(O)=C(O)C(O)=CC=1C1OC2=CC(O)=CC(O)=C2CC1OC(=O)C1=CC(O)=C(O)C(O)=C1 WMBWREPUVVBILR-UHFFFAOYSA-N 0.000 title claims abstract description 42
- 239000013078 crystal Substances 0.000 title claims abstract description 26
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- 239000003480 eluent Substances 0.000 claims abstract description 16
- 244000269722 Thea sinensis Species 0.000 claims abstract description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 14
- 235000009569 green tea Nutrition 0.000 claims abstract description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000004952 Polyamide Substances 0.000 claims abstract description 7
- 238000010828 elution Methods 0.000 claims abstract description 7
- 229920002647 polyamide Polymers 0.000 claims abstract description 7
- 239000012501 chromatography medium Substances 0.000 claims abstract description 6
- 238000004108 freeze drying Methods 0.000 claims abstract description 6
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 6
- 229910017488 Cu K Inorganic materials 0.000 claims description 2
- 229910017541 Cu-K Inorganic materials 0.000 claims description 2
- 230000005855 radiation Effects 0.000 claims description 2
- 239000000243 solution Substances 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 6
- 239000012088 reference solution Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000012085 test solution Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 229940094952 green tea extract Drugs 0.000 description 3
- 235000020688 green tea extract Nutrition 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 235000013824 polyphenols Nutrition 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000012488 sample solution Substances 0.000 description 3
- CITFYDYEWQIEPX-UHFFFAOYSA-N Flavanol Natural products O1C2=CC(OCC=C(C)C)=CC(O)=C2C(=O)C(O)C1C1=CC=C(O)C=C1 CITFYDYEWQIEPX-UHFFFAOYSA-N 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- ADRVNXBAWSRFAJ-UHFFFAOYSA-N catechin Natural products OC1Cc2cc(O)cc(O)c2OC1c3ccc(O)c(O)c3 ADRVNXBAWSRFAJ-UHFFFAOYSA-N 0.000 description 2
- 235000005487 catechin Nutrition 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 235000011987 flavanols Nutrition 0.000 description 2
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 2
- 150000008442 polyphenolic compounds Chemical class 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- 235000013616 tea Nutrition 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- XMOCLSLCDHWDHP-SWLSCSKDSA-N (+)-Epigallocatechin Natural products C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC(O)=C(O)C(O)=C1 XMOCLSLCDHWDHP-SWLSCSKDSA-N 0.000 description 1
- PFTAWBLQPZVEMU-DZGCQCFKSA-N (+)-catechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-DZGCQCFKSA-N 0.000 description 1
- 206010003210 Arteriosclerosis Diseases 0.000 description 1
- KYNSBQPICQTCGU-UHFFFAOYSA-N Benzopyrane Chemical compound C1=CC=C2C=CCOC2=C1 KYNSBQPICQTCGU-UHFFFAOYSA-N 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- XMOCLSLCDHWDHP-UHFFFAOYSA-N L-Epigallocatechin Natural products OC1CC2=C(O)C=C(O)C=C2OC1C1=CC(O)=C(O)C(O)=C1 XMOCLSLCDHWDHP-UHFFFAOYSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 208000007536 Thrombosis Diseases 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 208000011775 arteriosclerosis disease Diseases 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 150000001765 catechin Chemical class 0.000 description 1
- 208000026106 cerebrovascular disease Diseases 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 229950001002 cianidanol Drugs 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- XMOCLSLCDHWDHP-IUODEOHRSA-N epi-Gallocatechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2O)=CC(O)=C(O)C(O)=C1 XMOCLSLCDHWDHP-IUODEOHRSA-N 0.000 description 1
- DZYNKLUGCOSVKS-UHFFFAOYSA-N epigallocatechin Natural products OC1Cc2cc(O)cc(O)c2OC1c3cc(O)c(O)c(O)c3 DZYNKLUGCOSVKS-UHFFFAOYSA-N 0.000 description 1
- 229940030275 epigallocatechin gallate Drugs 0.000 description 1
- 150000002148 esters Chemical group 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 150000002206 flavan-3-ols Chemical class 0.000 description 1
- -1 flavanol compound Chemical class 0.000 description 1
- 229940074391 gallic acid Drugs 0.000 description 1
- 235000004515 gallic acid Nutrition 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 206010020718 hyperplasia Diseases 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 125000000686 lactone group Chemical group 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 230000008099 melanin synthesis Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000001000 micrograph Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000002000 scavenging effect Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000001757 thermogravimetry curve Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/60—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with aryl radicals attached in position 2
- C07D311/62—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with aryl radicals attached in position 2 with oxygen atoms directly attached in position 3, e.g. anthocyanidins
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Diabetes (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
本发明涉及EGCG晶型I的制备方法，属于药物化学技术领域。本发明提供了一种EGCG晶型I的制备方法，包括以下步骤：绿茶经水提获得绿茶提取液；将所述绿茶提取液采用聚酰胺作层析介质，洗脱剂为丙酮，洗脱时间为100min，得到洗脱液；所述洗脱剂的pH值为3.5，洗脱剂的流速为1.0mL/min；将所述洗脱液经冷冻干燥重结晶，即得EGCG晶型Ⅰ。本发明提供的制备方法操作简单，EGCG晶型Ⅰ的收率高。
Description
本申请是申请日为2018年11月21日、申请号为201811387339.6、发明名称为《EGCG晶型I及其制备方法》的发明专利的分案申请。
技术领域
本发明属于药物化学技术领域，具体的说，涉及EGCG晶型I的制备方法。
背景技术
EGCG(Epigallocatechin gallate)即表没食子儿茶素没食子酸酯，是绿茶茶多酚的主要组成成分。EGCG是茶叶特有的儿茶素，其量最高，占茶多酚制品的40％～50％。它是2-连苯酚基苯并吡喃与没食子酸形成的酯，具有酚类抗氧化剂的通用性，同时因其结构中有6个邻位酚羟基而有优于其他儿茶素的许多性质。
EGCG是典型的黄烷醇类化合物，因此具有黄烷醇的光谱特征。没食子儿茶素类除在240-280nm有吸收峰外，因其具有内酯结构而在350nm出峰，且通常有两个以上的峰位，EGCG的分子量为458，在室温和水中较稳定，pH值越低，稳定性越好。
大量的研究表明：EGCG具有抗菌、抗病毒、抗氧化、抗动脉硬化、抗血栓形成、抗血管增生、抗炎以及抗肿瘤作用，能清除自由基，对肾脏和肝脏的保护，降压、降脂、降血糖、抑制黑色素合成等功效。EGCG对多种疾病如癌症、心脑血管疾病、糖尿病、炎症等有预防保护作用。但是目前现有的制备方法中EGCG晶型I的收率较低。
发明内容
本发明提供了一种EGCG晶型I的制备方法，本发明提供的制备方法能够提高EGCG晶型I的收率。
为实现上述目的，本发明是通过如下技术方案实现的：
本发明提供了一种EGCG晶型I的制备方法，包括以下步骤：
绿茶经水提获得绿茶提取液；
将所述绿茶提取液采用聚酰胺作层析介质，洗脱剂为丙酮，洗脱时间为100min，得到洗脱液；所述洗脱剂的pH值为3.5，洗脱剂的流速为1.0mL/min；
将所述洗脱液经冷冻干燥重结晶，即得EGCG晶型Ⅰ；
所述EGCG晶型I使用Cu-Kα辐射，λ＝1.5405A，其以2θ角度表示的X-射线粉末衍射图中在5.197、8.481、10.357、12.121、15.601、17.04、19.501、20.74、21.481、22.443、23.778、24.481、25.919、26.438、28.162、28.899、29.501、30.839、31.401、35.481、36.901、38.739±0.2具有X-射线粉末衍射峰。
在本发明中，所述EGCG晶型I的X-射线粉末衍射2θ位置24.481处衍射峰强度为100％。
在本发明中，所述EGCG晶型I的DSC分析熔融温度为83.12±0.25℃。
本发明的有益效果：
本发明提供的EGCG晶型Ⅰ纯度高，杂质含量很少，溶解速度快，易溶于乙醇，可溶于水中。本发明涉及的制备方法操作简单，可稳定获得目标晶型，且收率高。
附图说明
图1是EGCG晶型Ⅰ的X-射线粉末衍射图；
图2是EGCG晶型Ⅰ的DSC图；
图3是EGCG晶型Ⅰ的红外光谱图；
图4是EGCG晶型Ⅰ的显微镜图；
图5是1mg/mL的EGCG标准品(a)与EGCG晶型Ⅰ(b)的HPLC对照图。
具体实施方式
为了使本发明的目的、技术方案和有益效果更加清楚，下面将对本发明的优选实施例进行详细的说明，以方便技术人员理解。
实施例1
取绿茶，加入适量蒸馏水，加热60～80℃提取，得绿茶提取液；绿茶提取液采用聚酰胺作层析介质，洗脱剂为丙酮，洗脱剂pH 2.5，洗脱剂流速1.0mL/min，洗脱时间100min，将洗脱液经冷冻干燥重结晶，即得EGCG晶体。收率93％。
实施例2
取绿茶，加入适量蒸馏水，加热60～80℃提取，得绿茶提取液；绿茶提取液采用聚酰胺作层析介质，洗脱剂为丙酮，洗脱剂pH 3.5，洗脱剂流速1.0mL/min，洗脱时间100min，将洗脱液经冷冻干燥重结晶，即得EGCG晶体。收率97％。
实施例3
取绿茶，加入适量蒸馏水，加热60～80℃提取，得绿茶提取液；绿茶提取液采用聚酰胺作层析介质，洗脱剂为丙酮，洗脱剂pH 4.5，洗脱剂流速1.0mL/min，洗脱时间100min，将洗脱液经冷冻干燥重结晶，即得EGCG晶体。收率91％。
实验分析
1、在聚酰胺层析分离试验中，洗脱剂pH 3.5、流速1.0mL/min时效果最佳，EGCG流出集中在85-150min之间，100min时EGCG洗脱达最大值，此时可获高纯度的EGCG单体，收率97％。
2、对实施例中得到的白色结晶粉末(EGCG晶体)进行x-射线衍射分析
仪器：日本理学仪器，D/Max-2200X射线粉末衍射仪；扫描范围(°2Theta)：5°～60°；扫描步长(°2Theta)：0.02；扫描速度(°/min)：10
取实施例2得到的白色结晶粉末进行分析，结果见图1和表1。
表1
其差示扫描热分析图(DSC图)如图2所示；其红外光谱图(IR)如图3所示；其显微镜图如图4所示。
实施例1、3的分析结果与实施例2的分析结果无明显差异。
3、EGCG的含量测定
色谱条件：以甲醇和水为流动相；流速为每分钟1mL；柱温40℃；检测波长280nm。
对照品溶液的制备，取EGCG对照品1mg，精密称定，使其溶于1mL的UP水中，使对照品溶液浓度为1mg/mL。
供试品溶液的制备，取EGCG供试品1mg，精密称定，使其溶于1mL的UP水中，使供试品溶液浓度为1mg/mL。
测定法分别精密吸取对照品溶液和供试品溶液各10微升，注入液相色谱仪，测定，即得。
杂质测定：取本品适量(相当于对照品1mg)，置于EP管中，加1mLUP水，作为供试品溶液。精密量取供试品1mg，溶于1mLUP水中，作为对照品溶液。照[含量测定]项下的色谱条件，取对照溶液10微升，注入液相色谱仪，调节检测灵敏度，使主成分色谱峰的峰高为满量程的10％，再精密量取供试品溶液与对照溶液各10微升，分别注入液相色谱仪，记录色谱图至主成分峰保留时间的2.5倍。供试品溶液色谱中，其他成分峰面积的和不得大于对照溶液主峰峰面积的2倍。
如图5所示，本发明实施例2得到的白色结晶粉末(EGCG晶型Ⅰ)中EGCG的含量高达97％以上。
实施例1、3的分析结果与实施例2的分析结果无明显差异。
本发明提供的制备方法操作简单，可稳定获得目标晶型。EGCG晶型Ⅰ纯度高，杂质含量很少，溶解速度快，易溶于乙醇，可溶于水中。
最后说明的是，以上优选实施例仅用于说明本发明的技术方案而非限制，尽管通过上述优选实施例已经对本发明进行了详细的描述，但本领域技术人员应当理解，可以在形式上和细节上对其作出各种各样的改变，而不偏离本发明权利要求书所限定的范围。
Claims (1)
1.一种EGCG晶型I的制备方法，其特征在于，包括以下步骤：
绿茶经水提获得绿茶提取液；
将所述绿茶提取液采用聚酰胺作层析介质，洗脱剂为丙酮，洗脱时间为100min，得到洗脱液；所述洗脱剂的pH值为3.5，洗脱剂的流速为1.0mL/min；
将所述洗脱液经冷冻干燥重结晶，即得EGCG晶型Ⅰ；
所述EGCG晶型I使用Cu-Kα辐射，λ＝1.5405A，其以2θ角度表示的X-射线粉末衍射图中在5.197、8.481、10.357、12.121、15.601、17.04、19.501、20.74、21.481、22.443、23.778、24.481、25.919、26.438、28.162、28.899、29.501、30.839、31.401、35.481、36.901、38.739±0.2具有X-射线粉末衍射峰。
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202211625707.2A CN115850228A (zh) | 2018-11-21 | 2018-11-21 | Egcg晶型i的制备方法 |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202211625707.2A CN115850228A (zh) | 2018-11-21 | 2018-11-21 | Egcg晶型i的制备方法 |
| CN201811387339.6A CN109293617A (zh) | 2018-11-21 | 2018-11-21 | Egcg晶型i及其制备方法 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201811387339.6A Division CN109293617A (zh) | 2018-11-21 | 2018-11-21 | Egcg晶型i及其制备方法 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN115850228A true CN115850228A (zh) | 2023-03-28 |
Family
ID=65143796
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202211625707.2A Pending CN115850228A (zh) | 2018-11-21 | 2018-11-21 | Egcg晶型i的制备方法 |
| CN201811387339.6A Pending CN109293617A (zh) | 2018-11-21 | 2018-11-21 | Egcg晶型i及其制备方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201811387339.6A Pending CN109293617A (zh) | 2018-11-21 | 2018-11-21 | Egcg晶型i及其制备方法 |
Country Status (1)
| Country | Link |
|---|---|
| CN (2) | CN115850228A (zh) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1465572A (zh) * | 2002-06-21 | 2004-01-07 | 浙江大学 | 表没食子儿茶素没食子酸酯单体纯化方法 |
| CN104447668A (zh) * | 2014-12-12 | 2015-03-25 | 中国医科大学 | 一种用氢键型大孔树脂制备高纯度egcg的方法 |
| US20180289715A1 (en) * | 2015-09-01 | 2018-10-11 | Amri Ssci, Llc | Polymorphs of cocrystals of epigallocatechin gallate and caffeine |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6013780A (ja) * | 1983-07-05 | 1985-01-24 | Mitsui Norin Kk | 茶カテキン類の製造方法 |
| ATE346059T1 (de) * | 1999-08-16 | 2006-12-15 | Dsm Ip Assets Bv | Verfahren zu herstellung von epigallocatechin gallate |
| US7510736B2 (en) * | 2004-02-06 | 2009-03-31 | UNIVERSITé LAVAL | Method for selectively and sequentially extracting catechins from green tea leaf |
| US8471044B2 (en) * | 2007-06-06 | 2013-06-25 | University Of South Florida | Epigallocatechin-3-gallate crystal compositions |
| CN109851604A (zh) * | 2017-11-30 | 2019-06-07 | 江苏天晟药业股份有限公司 | 一种表没食子儿茶素没食子酸酯晶型i及其制备方法 |
-
2018
- 2018-11-21 CN CN202211625707.2A patent/CN115850228A/zh active Pending
- 2018-11-21 CN CN201811387339.6A patent/CN109293617A/zh active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1465572A (zh) * | 2002-06-21 | 2004-01-07 | 浙江大学 | 表没食子儿茶素没食子酸酯单体纯化方法 |
| CN104447668A (zh) * | 2014-12-12 | 2015-03-25 | 中国医科大学 | 一种用氢键型大孔树脂制备高纯度egcg的方法 |
| US20180289715A1 (en) * | 2015-09-01 | 2018-10-11 | Amri Ssci, Llc | Polymorphs of cocrystals of epigallocatechin gallate and caffeine |
Non-Patent Citations (1)
| Title |
|---|
| 杨性民 等: "茶多酚中EGCG分离纯化工艺优化", 中国食品学报, vol. 6, no. 5, pages 77 - 80 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN109293617A (zh) | 2019-02-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Zhou et al. | Antioxidant homoisoflavonoids from Polygonatum odoratum | |
| Zheng et al. | Polyphenols from longan seeds and their radical-scavenging activity | |
| Xie et al. | Separation and purification of echinacoside from Penstemon barbatus (Can.) Roth by recycling high-speed counter-current chromatography | |
| JP4941991B2 (ja) | プロアントシアニジンオリゴマーの製造方法 | |
| Chen et al. | Isolation, identification and antioxidative capacity of water-soluble phenylpropanoid compounds from Rhodiola crenulata | |
| JP5439644B2 (ja) | ウーロン茶又は紅茶から抽出された血糖値上昇抑制剤及びミトコンドリア膜電位上昇剤 | |
| X Liu et al. | Extraction and characterization of proanthocyanidins from grape seeds | |
| Xiao et al. | Preparation of flavonoids and diarylheptanoid from Alpinia katsumadai hayata by microwave-assisted extraction and high-speed counter-current chromatography | |
| de Beer et al. | Use of countercurrent chromatography during isolation of 6-hydroxyluteolin-7-O-β-glucoside, a major antioxidant of Athrixia phylicoides | |
| CN102617672B (zh) | 一种金花茶黄酮苷及其制备方法和用途 | |
| Jia et al. | Flavonoids isolated from the fresh sweet fruit of Averrhoa carambola, commonly known as star fruit | |
| Schaufelberger et al. | Chemistry and pharmacology of Gentiana lactea | |
| Peng et al. | Separation and purification of four phenolic compounds from persimmon by high-speed counter-current chromatography | |
| Esatbeyoglu et al. | Semisynthetic preparation and isolation of dimeric procyanidins B1–B8 from roasted hazelnut skins (Corylus avellana L.) on a large scale using countercurrent chromatography | |
| Yang et al. | Two tetrahydroisoquinoline alkaloids from the fruit of Averrhoa carambola | |
| Zhu et al. | Lipase catalyzed acetylation of EGCG, a lipid soluble antioxidant, and preparative purification by high-speed counter-current chromatography (HSCCC) | |
| Wu et al. | Determination of caffeoylquinic acid derivatives in Azolla imbricata by chitosan-based matrix solid-phase dispersion coupled with HPLC–PDA | |
| Liu et al. | Simultaneous determination of three diarylheptanoids and an α-tetralone derivative in the green walnut husks (Juglans regia L.) by high-performance liquid chromatography with photodiode array detector | |
| Adams et al. | HPLC-profiling for antiplasmodial compounds—3-Methoxycarpachromene from Pistacia atlantica | |
| Kumar et al. | Separation of proanthocyanidins isolated from tea leaves using high-speed counter-current chromatography | |
| Feng et al. | Cytotoxic constitutents from Cryptocarya maclurei | |
| Yang et al. | Exploring and comparing two means of preparing and fractionating oligomeric proanthocyanidins from mangosteen pericarp: gel filtration chromatography and progressive solvent precipitation | |
| Yang et al. | Flavan-3-ols and 2-diglycosyloxybenzoates from the leaves of Averrhoa carambola | |
| Dalsgaard et al. | Noniosides E-H, new trisaccharide fatty acid esters from the fruit of Morinda citrifolia (Noni) | |
| CN110483541B (zh) | 一种异戊烯基化黄酮类化合物及其制备方法和应用 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination |