CN109293617A - EGCG crystal form I and preparation method thereof - Google Patents
EGCG crystal form I and preparation method thereof Download PDFInfo
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- CN109293617A CN109293617A CN201811387339.6A CN201811387339A CN109293617A CN 109293617 A CN109293617 A CN 109293617A CN 201811387339 A CN201811387339 A CN 201811387339A CN 109293617 A CN109293617 A CN 109293617A
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- 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 61
- 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 61
- 239000013078 crystal Substances 0.000 title claims abstract description 43
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- 239000003480 eluent Substances 0.000 claims abstract description 24
- 244000269722 Thea sinensis Species 0.000 claims abstract description 17
- 235000009569 green tea Nutrition 0.000 claims abstract description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000000634 powder X-ray diffraction Methods 0.000 claims abstract description 9
- 239000004952 Polyamide Substances 0.000 claims abstract description 8
- 238000010828 elution Methods 0.000 claims abstract description 8
- 239000012501 chromatography medium Substances 0.000 claims abstract description 6
- 229920002647 polyamide Polymers 0.000 claims abstract description 5
- 239000000178 monomer Substances 0.000 claims abstract description 4
- 238000002844 melting Methods 0.000 claims abstract description 3
- 230000008018 melting Effects 0.000 claims abstract description 3
- 239000007788 liquid Substances 0.000 claims description 5
- 239000000843 powder Substances 0.000 claims description 5
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 3
- 206010028980 Neoplasm Diseases 0.000 claims description 3
- 208000026106 cerebrovascular disease Diseases 0.000 claims description 3
- 206010012601 diabetes mellitus Diseases 0.000 claims description 3
- 230000002526 effect on cardiovascular system Effects 0.000 claims description 3
- 201000011510 cancer Diseases 0.000 claims description 2
- 229940094952 green tea extract Drugs 0.000 claims 2
- 235000020688 green tea extract Nutrition 0.000 claims 2
- 229910017488 Cu K Inorganic materials 0.000 claims 1
- 229910017541 Cu-K Inorganic materials 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 238000000113 differential scanning calorimetry Methods 0.000 claims 1
- 230000005855 radiation Effects 0.000 claims 1
- 238000003809 water extraction Methods 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 12
- -1 and eluant Substances 0.000 abstract description 10
- 238000004458 analytical method Methods 0.000 abstract description 7
- 239000012153 distilled water Substances 0.000 abstract description 5
- 238000000605 extraction Methods 0.000 abstract description 5
- 239000012535 impurity Substances 0.000 abstract description 5
- 238000001953 recrystallisation Methods 0.000 abstract description 5
- 238000000746 purification Methods 0.000 abstract 1
- 238000005303 weighing Methods 0.000 abstract 1
- 229940030275 epigallocatechin gallate Drugs 0.000 description 40
- 239000000243 solution Substances 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000013558 reference substance Substances 0.000 description 5
- 235000019441 ethanol Nutrition 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000012085 test solution Substances 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 235000013824 polyphenols Nutrition 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 150000001765 catechin Chemical class 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
- 150000002206 flavan-3-ols Chemical class 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
- 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
- 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 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 240000003152 Rhus chinensis Species 0.000 description 1
- 235000014220 Rhus chinensis Nutrition 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
- 208000011775 arteriosclerosis disease Diseases 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- QZHPTGXQGDFGEN-UHFFFAOYSA-N chromene Chemical compound C1=CC=C2C=C[CH]OC2=C1 QZHPTGXQGDFGEN-UHFFFAOYSA-N 0.000 description 1
- 229950001002 cianidanol Drugs 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 235000011987 flavanols Nutrition 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 229940074391 gallic acid Drugs 0.000 description 1
- 235000004515 gallic acid Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 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
- 230000002218 hypoglycaemic effect Effects 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 150000002596 lactones Chemical group 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000001151 other effect Effects 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000001612 separation test Methods 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 235000013616 tea Nutrition 0.000 description 1
Classifications
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- 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
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- 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
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Diabetes (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Hematology (AREA)
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- Biomedical Technology (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The present invention relates to EGCG crystal form I and preparation method thereof, belong to field of pharmaceutical chemistry technology, and the present invention provides a kind of EGCG crystal forms, are named as EGCG crystal form I, use Cu-KαIt radiates, λ=1.5405A, diffraction peak intensity is 100% at 2 position θ 24.481 of X-ray powder diffraction, and dsc analysis crystal form I melting temperature is 83.12 DEG C.EGCG crystal form I's prepares purification process the following steps are included: weighing green tea, and appropriate distilled water is added, and heats 60 ~ 80 DEG C of extractions, obtains green tea extractive liquor；Green tea extractive liquor makees chromatography media using polyamide, and eluant, eluent is acetone, and eluant, eluent pH2.5 ~ 4.5, eluant, eluent 1.0 ~ 2.0mL/min of flow velocity, elution time 100min can obtain the EGCG monomer of high-purity, by the freeze-dried recrystallization of eluent to get EGCG crystal form I.Preparation method of the present invention is easy to operate, can stablize the EGCG crystal form I for obtaining that impurity content is seldom, solution rate is fast.
Description
Technical field
The invention belongs to field of pharmaceutical chemistry technology, specifically, are related to EGCG crystal form I and preparation method thereof.
Background technique
EGCG (Epigallocatechin gallate) i.e. Epigallo-catechin gallate (EGCG), is Green Tea Polyphenols
Main constituents.EGCG is the distinctive catechin of tealeaves, and amount highest accounts for the 40%~50% of tea polyphenols product.It is
2- connects the ester that phenylol chromene and gallic acid are formed, and has the versatility of phenol antioxidant, while because in its structure
There are 6 ortho position phenolic hydroxyl groups and there are many properties better than other catechins.
EGCG is typical flavanols compounds, therefore the spectral signature with flavanols.Nutgall catechin class is removed
Have outside absorption peak in 240-280nm, in 350nm appearance due to it is with lactone structure, and usually there are two above peak position,
The molecular weight of EGCG is 458, and more stable in room temperature and water, pH value is lower, and stability is better.
It is a large amount of research shows that: EGCG has antibacterial, antiviral, anti-oxidant, anti arteriosclerosis, antithrombus formation, anti-blood
Pipe hyperplasia, anti-inflammatory and antitumor action, can remove free radical, the protection to kidney and liver, decompression, lipid-loweringing, hypoglycemic, suppression
B16 cell processed and other effects.EGCG has prevention & protection to a variety of disorders such as cancers, cardiovascular and cerebrovascular disease, diabetes, inflammation etc.
Effect.And up to the present, it is domestic still to be reported without the crystal form of open EGCG.
Summary of the invention
In order to solve the problems, such as background technique, the present invention provides a kind of EGCG new, that solution rate is fast is brilliant
Type I and preparation method thereof, is soluble in ethyl alcohol, it is water-soluble in, and impurity content is low.
To achieve the above object, the present invention is achieved through the following technical solutions:
The EGCG crystal form I, uses Cu-KαRadiation, λ=1.5405A, the X-ray powder diffraction indicated with 2 θ angles
In figure 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 have X-ray powder diffraction peak.
The X-ray powder diffraction figure of EGCG crystal form I is substantially as shown in Figure 1.
Diffraction peak intensity is 100% at 2 position θ 24.481 of X-ray powder diffraction of EGCG crystal form I, and dsc analysis is molten
Melting temperature is 83.12 DEG C ± 0.25；Its IR (KBr, cm-1) data substantially such as Fig. 2.
The preparation method of the EGCG crystal form I, comprising the following steps: green tea is weighed, is added appropriate distilled water, heating 60~
80 DEG C of extractions, obtain green tea extractive liquor；Green tea extractive liquor makees chromatography media using polyamide, and eluant, eluent is acetone, eluant, eluent pH2.5
~4.5, eluant, eluent 1.0~2.0mL/min of flow velocity, elution time 100min can obtain the EGCG monomer of high-purity, eluent passed through
Freeze-drying recrystallization is to get the EGCG crystal form I.
In polyamide chromatography separation, effect is best when eluant, eluent pH 3.5, flow velocity 1.0mL/min.
Application of the EGCG crystal form I in treating cancer, cardiovascular and cerebrovascular disease, diabetes.
Beneficial effects of the present invention:
I purity is high of EGCG crystal form provided by the invention, impurity content is seldom, and solution rate is fast, is soluble in ethyl alcohol, dissolves in
In water.Preparation method of the present invention is easy to operate, can stablize and obtain target crystal form.
Detailed description of the invention
Fig. 1 is the X-ray powder diffraction figure of EGCG crystal form I.
Fig. 2 is the DSC figure of EGCG crystal form I.
Fig. 3 is the infrared spectrogram of EGCG crystal form I.
Fig. 4 is the microscope figure of EGCG crystal form I.
Fig. 5 is the EGCG standard items (a) of 1mg/ml and the HPLC comparative diagram of EGCG crystal form I (b).
Specific embodiment
It, below will be to preferred reality of the invention in order to keep the purpose of the present invention, technical scheme and beneficial effects clearer
It applies example to be described in detail, to facilitate the technical staff to understand.
Embodiment 1
Green tea is taken, appropriate distilled water is added, 60~80 DEG C of extractions is heated, obtains green tea extractive liquor；Green tea extractive liquor is using poly-
Amide makees chromatography media, and eluant, eluent is acetone, eluant, eluent pH 2.5, eluant, eluent flow velocity 1.0mL/min, elution time 100min,
By the freeze-dried recrystallization of eluent to get EGCG crystal.Yield 93%.
Embodiment 2
Green tea is taken, appropriate distilled water is added, 60~80 DEG C of extractions is heated, obtains green tea extractive liquor；Green tea extractive liquor is using poly-
Amide makees chromatography media, and eluant, eluent is acetone, eluant, eluent pH 3.5, eluant, eluent flow velocity 1.0mL/min, elution time 100min,
By the freeze-dried recrystallization of eluent to get EGCG crystal.Yield 97%.
Embodiment 3
Green tea is taken, appropriate distilled water is added, 60~80 DEG C of extractions is heated, obtains green tea extractive liquor；Green tea extractive liquor is using poly-
Amide makees chromatography media, and eluant, eluent is acetone, eluant, eluent pH 4.5, eluant, eluent flow velocity 1.0mL/min, elution time 100min,
By the freeze-dried recrystallization of eluent to get EGCG crystal.Yield 91%.
Experimental analysis
1, in polyamide chromatography separation test, effect is best when eluant, eluent pH 3.5, flow velocity 1.0mL/min, EGCG stream
It concentrates between 85-150min out, EGCG elution reaches maximum value when 100min, can obtain the EGCG monomer of high-purity, yield at this time
97%.
2, X-ray diffraction analysis is carried out to white crystalline powder obtained in embodiment (EGCG crystal)
Instrument: Rigaku instrument, D/Max-2200X ray powder diffractometer；Scanning range (° 2Theta): 5 °~
60°；Scanning step (° 2Theta): 0.02；Scanning speed (°/min): 10
The white crystalline powder that Example 2 obtains is analyzed, the result is shown in Figure 1 and table 1.
Table 1
Its differential scanning calorimeter figure (DSC figure) is as shown in Figure 2；Its infrared spectrogram (IR) is as shown in Figure 3；Its microscope
Figure is as shown in Figure 4.
The analysis result of embodiment 1,3 and the analysis result no significant difference of embodiment 2.
3, the assay of EGCG
Chromatographic condition: using first alcohol and water as mobile phase；Flow velocity is 1ml per minute；40 DEG C of column temperature；Detection wavelength 280nm.
The preparation of reference substance solution takes EGCG reference substance 1mg, accurately weighed, is dissolved in it in UP water of 1ml, makes to compare
Product solution concentration is 1mg/ml.
The preparation of test solution takes EGCG test sample 1mg, accurately weighed, is dissolved in it in UP water of 1ml, makes for examination
Product solution concentration is 1mg/ml.
Measuring method is accurate respectively to draw reference substance solution and each 10 microlitres of test solution, injects liquid chromatograph, measures,
To obtain the final product.
Impurity determination: it takes this product appropriate (being equivalent to reference substance 1mg), is placed in EP pipe, adds 1ml UP water, as test sample
Solution.Precision measures test sample 1mg, is dissolved in 1ml UP water, as reference substance solution.According to the chromatostrip under [assay] item
Part takes 10 microlitres of contrast solution, injects liquid chromatograph, adjusts detection sensitivity, measures the peak height of principal component chromatographic peak completely
The 10% of journey, then accurate measurement test solution and each 10 microlitres of contrast solution, are injected separately into liquid chromatograph, record chromatogram
To 2.5 times of principal component peak retention time.In test solution chromatography, the sum of other compositions peak area is not greater than contrast solution
2 times of main peak peak area.
As shown in figure 5, the content of EGCG is up in the white crystalline powder (EGCG crystal form I) that the embodiment of the present invention 2 obtains
97% or more.
The analysis result of embodiment 1,3 and the analysis result no significant difference of embodiment 2.
Preparation method provided by the invention is easy to operate, can stablize and obtain target crystal form.I purity is high of EGCG crystal form, impurity
Content is seldom, and solution rate is fast, is soluble in ethyl alcohol, it is water-soluble in.
Finally, it is stated that preferred embodiment above is only used to illustrate the technical scheme of the present invention rather than limits, although logical
It crosses above preferred embodiment the present invention is described in detail, however, those skilled in the art should understand that, can be
Various changes are made to it in form and in details, without departing from claims of the present invention limited range.
Claims (7)
Priority Applications (2)
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|---|---|---|---|
| CN201811387339.6A CN109293617A (en) | 2018-11-21 | 2018-11-21 | EGCG crystal form I and preparation method thereof |
| CN202211625707.2A CN115850228A (en) | 2018-11-21 | 2018-11-21 | Preparation method of EGCG crystal form I |
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| CN201811387339.6A CN109293617A (en) | 2018-11-21 | 2018-11-21 | EGCG crystal form I and preparation method thereof |
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| CN202211625707.2A Division CN115850228A (en) | 2018-11-21 | 2018-11-21 | Preparation method of EGCG crystal form I |
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| CN201811387339.6A Pending CN109293617A (en) | 2018-11-21 | 2018-11-21 | EGCG crystal form I and preparation method thereof |
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Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4613672A (en) * | 1983-07-05 | 1986-09-23 | Mitsu Norin Co., Ltd. | Process for the production of tea catechins |
| US20030083270A1 (en) * | 1999-08-16 | 2003-05-01 | Roche Vitamins, Inc. | Process for the production of (-)-epigallocatechin gallate |
| CN1465572A (en) * | 2002-06-21 | 2004-01-07 | 浙江大学 | Purification method of epigallocatechin gallate monomer |
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| US20100173984A1 (en) * | 2007-06-06 | 2010-07-08 | University Of South Florida | Epigallocatechin-3-gallate crystal compositions |
| CN104447668A (en) * | 2014-12-12 | 2015-03-25 | 中国医科大学 | Method for preparing high-purity EGCG from hydrogen-bonded macroporous resin |
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-
2018
- 2018-11-21 CN CN202211625707.2A patent/CN115850228A/en active Pending
- 2018-11-21 CN CN201811387339.6A patent/CN109293617A/en active Pending
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|---|---|---|---|---|
| US4613672A (en) * | 1983-07-05 | 1986-09-23 | Mitsu Norin Co., Ltd. | Process for the production of tea catechins |
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| US20100173984A1 (en) * | 2007-06-06 | 2010-07-08 | University Of South Florida | Epigallocatechin-3-gallate crystal compositions |
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| US20180289715A1 (en) * | 2015-09-01 | 2018-10-11 | Amri Ssci, Llc | Polymorphs of cocrystals of epigallocatechin gallate and caffeine |
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| Title |
|---|
| 杨性民 等: "茶多酚中EGCG分离纯化工艺优化", 《中国食品学报》 * |
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| CN115850228A (en) | 2023-03-28 |
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