CN106279199A - A kind of synthetic method of ellagic acid - Google Patents
A kind of synthetic method of ellagic acid Download PDFInfo
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- CN106279199A CN106279199A CN201610680283.8A CN201610680283A CN106279199A CN 106279199 A CN106279199 A CN 106279199A CN 201610680283 A CN201610680283 A CN 201610680283A CN 106279199 A CN106279199 A CN 106279199A
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- acid
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- synthetic method
- ellagic acid
- organic solvent
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- AFSDNFLWKVMVRB-UHFFFAOYSA-N Ellagic acid Chemical compound OC1=C(O)C(OC2=O)=C3C4=C2C=C(O)C(O)=C4OC(=O)C3=C1 AFSDNFLWKVMVRB-UHFFFAOYSA-N 0.000 title claims abstract description 34
- ATJXMQHAMYVHRX-CPCISQLKSA-N Ellagic acid Natural products OC1=C(O)[C@H]2OC(=O)c3cc(O)c(O)c4OC(=O)C(=C1)[C@H]2c34 ATJXMQHAMYVHRX-CPCISQLKSA-N 0.000 title claims abstract description 34
- 229920002079 Ellagic acid Polymers 0.000 title claims abstract description 34
- 235000004132 ellagic acid Nutrition 0.000 title claims abstract description 34
- 229960002852 ellagic acid Drugs 0.000 title claims abstract description 34
- FAARLWTXUUQFSN-UHFFFAOYSA-N methylellagic acid Natural products O1C(=O)C2=CC(O)=C(O)C3=C2C2=C1C(OC)=C(O)C=C2C(=O)O3 FAARLWTXUUQFSN-UHFFFAOYSA-N 0.000 title claims abstract description 34
- 238000010189 synthetic method Methods 0.000 title claims abstract description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 37
- LRBQNJMCXXYXIU-NRMVVENXSA-N tannic acid Chemical compound OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-NRMVVENXSA-N 0.000 claims abstract description 21
- TUSDEZXZIZRFGC-UHFFFAOYSA-N 1-O-galloyl-3,6-(R)-HHDP-beta-D-glucose Natural products OC1C(O2)COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC1C(O)C2OC(=O)C1=CC(O)=C(O)C(O)=C1 TUSDEZXZIZRFGC-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000001263 FEMA 3042 Substances 0.000 claims abstract description 18
- LRBQNJMCXXYXIU-PPKXGCFTSA-N Penta-digallate-beta-D-glucose Natural products OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-PPKXGCFTSA-N 0.000 claims abstract description 18
- 238000006243 chemical reaction Methods 0.000 claims abstract description 18
- 235000015523 tannic acid Nutrition 0.000 claims abstract description 18
- 229920002258 tannic acid Polymers 0.000 claims abstract description 18
- 229940033123 tannic acid Drugs 0.000 claims abstract description 18
- 239000000284 extract Substances 0.000 claims abstract description 9
- 239000001117 sulphuric acid Substances 0.000 claims abstract description 9
- 235000011149 sulphuric acid Nutrition 0.000 claims abstract description 9
- 239000000243 solution Substances 0.000 claims abstract description 8
- 239000007864 aqueous solution Substances 0.000 claims abstract description 7
- 239000003960 organic solvent Substances 0.000 claims abstract description 7
- 238000013517 stratification Methods 0.000 claims abstract description 7
- 208000035126 Facies Diseases 0.000 claims abstract description 6
- 239000000376 reactant Substances 0.000 claims abstract description 6
- 239000008346 aqueous phase Substances 0.000 claims abstract description 3
- 239000003054 catalyst Substances 0.000 claims abstract description 3
- 238000001816 cooling Methods 0.000 claims abstract description 3
- 238000001914 filtration Methods 0.000 claims abstract description 3
- 238000001953 recrystallisation Methods 0.000 claims abstract description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- 239000011521 glass Substances 0.000 claims description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- 238000000605 extraction Methods 0.000 claims description 3
- 238000012805 post-processing Methods 0.000 claims description 3
- 238000005984 hydrogenation reaction Methods 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 238000000034 method Methods 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
- 238000003810 ethyl acetate extraction Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 230000002087 whitening effect Effects 0.000 description 3
- XUMBMVFBXHLACL-UHFFFAOYSA-N Melanin Chemical compound O=C1C(=O)C(C2=CNC3=C(C(C(=O)C4=C32)=O)C)=C2C4=CNC2=C1C XUMBMVFBXHLACL-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 description 2
- 238000005903 acid hydrolysis reaction Methods 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 230000006837 decompression Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- 241001597008 Nomeidae Species 0.000 description 1
- 102000003992 Peroxidases Human genes 0.000 description 1
- 102000003425 Tyrosinase Human genes 0.000 description 1
- 108060008724 Tyrosinase Proteins 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000000701 coagulant Substances 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 235000004515 gallic acid Nutrition 0.000 description 1
- 229940074391 gallic acid Drugs 0.000 description 1
- 229920001461 hydrolysable tannin Polymers 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 108040007629 peroxidase activity proteins Proteins 0.000 description 1
- 210000002381 plasma Anatomy 0.000 description 1
- -1 polyphenol compounds Chemical class 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000000473 propyl gallate Substances 0.000 description 1
- 229940075579 propyl gallate Drugs 0.000 description 1
- 235000010388 propyl gallate Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229920001864 tannin Polymers 0.000 description 1
- 235000018553 tannin Nutrition 0.000 description 1
- 239000001648 tannin Substances 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/06—Peri-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
The present invention discloses the synthetic method of a kind of ellagic acid, it is characterised in that: react in pressurized reactor, 1) catalyst that hydrolyzes as tannic acid (II) using sulphuric acid, sulphuric acid is configured to aqueous solution；2) reaction mass that tannic acid is mixed homogeneously with sulfuric acid solution carries out compressive reaction；3), after reaction terminates, reactant liquor is neutralized；4) reactant liquor neutralized extracts with organic solvent, stratification, separates aqueous phase and organic facies, and organic facies is concentrated, cooling, crystallize, filtration, recrystallization purifying, be dried to obtain ellagic acid.
Description
Technical field
The present invention relates to a kind of method preparing ellagic acid with tannic acid in pressurized reactor, belong to field of fine chemical
The preparation method of antioxidant.
Background technology
Ellagic acid (2,3,7,8-tetrahydroxy benzopyrano [5,4,3-cde]-
Benzopyran-5,10-dione) it is a kind of natural polyphenol compounds, it is widely present in plant tissue.Its
Free form is the dimerization derivant of gallic acid, it is also possible to be condensed into the form of elladitannin.
Free form ellagic acid has following purposes: be used clinically for the separation of blood plasma as coagulant；Have is anti-
Oxidisability is possible to prevent the oxidation of mixed oil, vegetable oil, animal oil, and life such as tieed up by the antioxidant that its oxidation resistance is better than commonly using
Element E and propylgallate；It it is one of department of dermatologry MA spendable whitening effect composition.For skin whitening, press down
Tyrosinase activity processed, blocks melanin and generates, have whitening and the effect of light speckle.In recent years, the antitumaous effect of ellagic acid
Research also result in bigger concern.The multiduty commodity value of ellagic acid makes it continuous in the demand of international and domestic market
Rise.
At present, the method that prepared by ellagic acid is gone through following several:
Jurd report [J.Am.Chem.Soc.1956,78,3445-3448.] in 1956, at high temperature with sulphuric acid hydrolysis tan
Flower tannin, the productivity preparing ellagic acid can reach 40%.Due to high temperature, the technique of strong acid, controlling process complicated, risk is relatively big,
Institute is the most never commercially produced employing.
Mayer in 1984 etc. report [Liebigs Ann.Chem., 1984,929-938.], do not have with peroxidase oxidization
Gallate-based prepares ellagic acid, but the yield of ellagic acid only has 20～30%, and post processing is loaded down with trivial details, and by-product is many, it is difficult to purification.
The report such as nineteen ninety Khac [Phytochemistry, 1990,29 (1), 251～256], from containing a small amount of ellagic acid
Plant in extract.Highly purified ellagic acid can be obtained, but extraction ratio is 1%.Minority enterprise is had to use this method in the world,
Its ellagic acid product price is high, and yield is the least.
Nineteen ninety, marshy land has been waited with Japanese Patent flat 2-255686 patent disclosure at room temperature, normal pressure, weak basic condition clearly
Under, the method preparing ellagic acid with oxidizing elladitannin, from technique, there is relatively quantum jump.Its yield can reach 50
～60%.
Above-mentioned visible, the preparation method of ellagic acid, and will be using elladitannin extract as former still in low yield state
Material, then through traditional hydrolysis or oxidizing process, ellagic acid could be prepared with higher yields.
During the present invention utilizes high-temperature strong acid Hydrolysable Tannins processed with acid for ellagic acid according to nineteen fifty-seven, propose in pressurization anti-
Answer and device carries out this reaction, it is provided that a kind of easily controllable and ellagic acid preparation technology that yield is higher.
Summary of the invention
The present invention is to provide and a kind of add pyrohydrolysis with tannic acid through sulphuric acid in pressurized reactor and prepare ellagic acid.The method
Utilizing pressurization to be changed into the feature of ellagic acid after promoting tannic acid hydrolysis, productivity can reach more than 70%.
The technical scheme is that the synthetic method of a kind of ellagic acid, react in pressurized reactor,
1) catalyst hydrolyzed as tannic acid (II) using sulphuric acid, sulphuric acid is configured to aqueous solution；
2) reaction mass that tannic acid is mixed homogeneously with sulfuric acid solution carries out compressive reaction；
3), after reaction terminates, reactant liquor is neutralized；
4) reactant liquor neutralized extracts with organic solvent, stratification, separates aqueous phase and organic facies, organic facies is concentrated,
Cooling, crystallize, filtration, recrystallization purifying, it is dried to obtain ellagic acid.
The concentration of described described aqueous sulfuric acid is 10～60%；Tannic acid and sulfuric acid solution amount ratio are 1:10～1:
50, unit is kilogram/liter；Reaction temperature 40～100 DEG C.
Described tannic acid is mixed homogeneously in pressurized reactor with sulfuric acid solution, reaction pressure control be 0.1～
0.5MPa。
Described organic solvent is ethyl acetate, chloroform or dichloromethane.
Described pressurized reactor is high pressure resistant glass hydrogenation bottle.
The present invention uses and prepares the technique of ellagic acid in pressurized reactor compared with prior art, has the advantage that
1. tannic acid and sulfuric acid solution are directly synthesized ellagic acid, and reaction temperature is within 100 DEG C；
2., under identical material amount proportioning, the conversion ratio in pressurized reactor is all higher than conventional reactor；
The present invention is under sulphuric acid pyrohydrolysis process conditions, and the productivity of ellagic acid is more than 70%, close to 90%.
Detailed description of the invention
Embodiment 1
90% 5 grams of tannic acid and 50% aqueous sulfuric acid amount ratio are 50 milliliters, are placed in the glass pressurization of 100 milliliters of volumes
In reactor, react；Flow speed control is at 50mL/min, and pressure is shown as 0.5MPa, and temperature of reactor is set to 100 DEG C；Instead
Should terminate, neutralize with 50% sodium hydrate aqueous solution, add ethyl acetate extraction；Stratification, collected organic layer, reduces pressure dense
Contracting, concentrated extract is with high performance liquid chromatograph analysis.Analysis condition is enlightening horse C18 post, and flowing is acetonitrile mutually: 0.03% phosphoric acid=
20:80, monitors wavelength 254nm；Sending out calculated yield through ellagic acid standard substance external standard is 79%.
Embodiment 2
90% 5 grams of tannic acid and 60% aqueous sulfuric acid amount ratio are 50 milliliters, are placed in the glass pressurization of 100 milliliters of volumes
In reactor, react；Flow speed control is at 50mL/min, and pressure is shown as 0.5MPa, and temperature of reactor is set to 100 DEG C；Instead
Should terminate, neutralize with 50% sodium hydrate aqueous solution, add ethyl acetate extraction；Stratification, collected organic layer, reduces pressure dense
Contracting, concentrated extract is with high performance liquid chromatograph analysis；Analysis condition is with embodiment 1；Send out calculating through ellagic acid standard substance external standard to receive
Rate is 89%.
Embodiment 3
90% 2.5 grams of tannic acid and 60% aqueous sulfuric acid amount ratio are 50 milliliters, and the glass being placed in 100 milliliters of volumes adds
In pressure reactor, react；Flow speed control is at 50mL/min, and pressure is shown as 0.5MPa, and temperature of reactor is set to 100 DEG C；
Reaction terminates, and neutralizes with 50% sodium hydrate aqueous solution, adds ethyl acetate extraction；Stratification, collected organic layer, decompression
Concentrating, concentrated extract is with high performance liquid chromatograph analysis；Analysis condition is with embodiment 1；Calculating is sent out through ellagic acid standard substance external standard
Yield is 80%.
Embodiment 4
90% 2.5 grams of tannic acid and 70% aqueous sulfuric acid amount ratio are 50 milliliters, and the glass being placed in 100 milliliters of volumes adds
In pressure reactor, react；Flow speed control is at 50mL/min, and pressure is shown as 0.5MPa, and temperature of reactor is set to 100 DEG C；
Reaction terminates, and neutralizes with 50% sodium hydrate aqueous solution, adds ethyl acetate extraction；Stratification, collected organic layer, decompression
Concentrating, concentrated extract is with high performance liquid chromatograph analysis；Analysis condition is with embodiment 1；Calculating is sent out through ellagic acid standard substance external standard
Yield is 75%.
Claims (5)
1. the synthetic method of an ellagic acid, it is characterised in that: react in pressurized reactor,
1) catalyst hydrolyzed as tannic acid (II) using sulphuric acid, sulphuric acid is configured to aqueous solution；
2) reaction mass that tannic acid is mixed homogeneously with sulfuric acid solution carries out compressive reaction；
3), after reaction terminates, reactant liquor is neutralized；
4) reactant liquor neutralized extracts with organic solvent, stratification, separates aqueous phase and organic facies, organic facies is concentrated, cooling,
Crystallize, filtration, recrystallization purifying, it is dried to obtain ellagic acid.
Synthetic method the most according to claim 1, it is characterised in that: the concentration of described aqueous sulfuric acid is 10～60%；
Tannic acid and sulfuric acid solution amount ratio are 1:10～1:50, and unit is kilogram/liter；Reaction temperature 40～100 DEG C.
Synthetic method the most according to claim 1, it is characterised in that: tannic acid and sulfuric acid solution are mixed in pressurized reactor
Closing uniformly, it is 0.1～0.5MPa that reaction pressure controls.
The post-processing approach of organic solvent the most according to claim 1 extraction, it is characterised in that: organic solvent is acetic acid second
Ester, chloroform or dichloromethane.
The post-processing approach of organic solvent the most according to claim 1 extraction, it is characterised in that: described pressurized reactor is
High pressure resistant glass hydrogenation bottle.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610680283.8A CN106279199A (en) | 2016-08-18 | 2016-08-18 | A kind of synthetic method of ellagic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610680283.8A CN106279199A (en) | 2016-08-18 | 2016-08-18 | A kind of synthetic method of ellagic acid |
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| Publication Number | Publication Date |
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| CN106279199A true CN106279199A (en) | 2017-01-04 |
Family
ID=57679067
Family Applications (1)
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| CN201610680283.8A Pending CN106279199A (en) | 2016-08-18 | 2016-08-18 | A kind of synthetic method of ellagic acid |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113717192A (en) * | 2021-08-25 | 2021-11-30 | 湖南华诚生物资源股份有限公司 | Method for separating ellagic acid from byproducts of rubusoside production |
| CN114656478A (en) * | 2020-12-23 | 2022-06-24 | 中国林业科学研究院资源昆虫研究所 | A kind of preparation method of ellagic acid |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101434608A (en) * | 2008-12-12 | 2009-05-20 | 桂林莱茵生物科技股份有限公司 | Preparation of high-purity ellagic acid |
-
2016
- 2016-08-18 CN CN201610680283.8A patent/CN106279199A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101434608A (en) * | 2008-12-12 | 2009-05-20 | 桂林莱茵生物科技股份有限公司 | Preparation of high-purity ellagic acid |
Non-Patent Citations (8)
| Title |
|---|
| LEONARD JDURD: "Plant Polyphenols. I. The Polyphenolic Constituents of the Pellicle of the Walnut(Jugluns regia)", 《J.AM.CHEM.SOC.》 * |
| MAKOTO ISHIMATSU，等: "Tannins and Related Compounds.LXXV.Isolation and Characterization of Novel Diastereoisomeric Ellagitannins,Nupharins A and B, and Their Homologues from Nuphar japonicum DC.", 《CHEM. PHARM. BULL.》 * |
| TAKASHI YOSHIDA等: "Heterophylliins A,B,C,D and E, Ellagitannin Monomers and Dimers from Corylus heterophylla Fisch", 《CHEM. PHARM. BULL.》 * |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114656478A (en) * | 2020-12-23 | 2022-06-24 | 中国林业科学研究院资源昆虫研究所 | A kind of preparation method of ellagic acid |
| CN114656478B (en) * | 2020-12-23 | 2023-08-18 | 中国林业科学研究院资源昆虫研究所 | A kind of preparation method of ellagic acid |
| CN113717192A (en) * | 2021-08-25 | 2021-11-30 | 湖南华诚生物资源股份有限公司 | Method for separating ellagic acid from byproducts of rubusoside production |
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Application publication date: 20170104 |