CA1109865A - Procede de purification d'anthocyanes - Google Patents
Procede de purification d'anthocyanesInfo
- Publication number
- CA1109865A CA1109865A CA295,491A CA295491A CA1109865A CA 1109865 A CA1109865 A CA 1109865A CA 295491 A CA295491 A CA 295491A CA 1109865 A CA1109865 A CA 1109865A
- Authority
- CA
- Canada
- Prior art keywords
- solution
- anthocyanins
- adsorbent
- silica
- metal oxide
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims abstract description 23
- 238000000746 purification Methods 0.000 title claims 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 68
- 239000000243 solution Substances 0.000 claims abstract description 60
- 239000000377 silicon dioxide Substances 0.000 claims abstract description 34
- 239000004410 anthocyanin Substances 0.000 claims abstract description 33
- 235000010208 anthocyanin Nutrition 0.000 claims abstract description 33
- 229930002877 anthocyanin Natural products 0.000 claims abstract description 33
- 150000004636 anthocyanins Chemical class 0.000 claims abstract description 33
- 239000003463 adsorbent Substances 0.000 claims abstract description 28
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims abstract description 26
- 229910044991 metal oxide Inorganic materials 0.000 claims abstract description 16
- 150000004706 metal oxides Chemical class 0.000 claims abstract description 14
- 229920000642 polymer Polymers 0.000 claims abstract description 14
- 239000007864 aqueous solution Substances 0.000 claims abstract description 11
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 21
- 239000000178 monomer Substances 0.000 claims description 21
- 238000010828 elution Methods 0.000 claims description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 238000004132 cross linking Methods 0.000 claims description 6
- 238000001179 sorption measurement Methods 0.000 claims description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 6
- 229920002554 vinyl polymer Polymers 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 229920001577 copolymer Polymers 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 3
- 238000001704 evaporation Methods 0.000 claims description 3
- 230000008020 evaporation Effects 0.000 claims description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- MPMBRWOOISTHJV-UHFFFAOYSA-N but-1-enylbenzene Chemical class CCC=CC1=CC=CC=C1 MPMBRWOOISTHJV-UHFFFAOYSA-N 0.000 claims description 2
- 150000001993 dienes Chemical class 0.000 claims description 2
- 238000006116 polymerization reaction Methods 0.000 claims description 2
- QROGIFZRVHSFLM-UHFFFAOYSA-N prop-1-enylbenzene Chemical class CC=CC1=CC=CC=C1 QROGIFZRVHSFLM-UHFFFAOYSA-N 0.000 claims description 2
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 claims description 2
- 239000002594 sorbent Substances 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- 238000005470 impregnation Methods 0.000 claims 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims 1
- 238000000935 solvent evaporation Methods 0.000 claims 1
- 239000010936 titanium Substances 0.000 claims 1
- 229910052719 titanium Inorganic materials 0.000 claims 1
- 239000001045 blue dye Substances 0.000 abstract description 2
- 235000013305 food Nutrition 0.000 abstract description 2
- 239000001044 red dye Substances 0.000 abstract description 2
- 239000000284 extract Substances 0.000 description 20
- 238000004040 coloring Methods 0.000 description 11
- 235000019441 ethanol Nutrition 0.000 description 9
- 239000002245 particle Substances 0.000 description 7
- 238000000926 separation method Methods 0.000 description 7
- 239000000454 talc Substances 0.000 description 6
- 229910052623 talc Inorganic materials 0.000 description 6
- 239000004793 Polystyrene Substances 0.000 description 5
- 229920002223 polystyrene Polymers 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 4
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 230000001476 alcoholic effect Effects 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 239000011148 porous material Substances 0.000 description 3
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000005325 percolation Methods 0.000 description 2
- 235000020095 red wine Nutrition 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical group O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 1
- 239000004641 Diallyl-phthalate Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 1
- 238000000889 atomisation Methods 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 1
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 235000013365 dairy product Nutrition 0.000 description 1
- 125000004386 diacrylate group Chemical group 0.000 description 1
- -1 diluted or not Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000002864 food coloring agent Nutrition 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000035800 maturation Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- OINMATXWPCYGSR-UHFFFAOYSA-N n-methylidenebuta-2,3-dienamide Chemical compound C=NC(=O)C=C=C OINMATXWPCYGSR-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000014594 pastries Nutrition 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 235000011962 puddings Nutrition 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000011514 vinification Methods 0.000 description 1
- 229960000834 vinyl ether Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B61/00—Dyes of natural origin prepared from natural sources, e.g. vegetable sources
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Treatment Of Liquids With Adsorbents In General (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR77.01890 | 1977-01-24 | ||
| FR7701890A FR2378040B1 (en, 2012) | 1977-01-24 | 1977-01-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1109865A true CA1109865A (fr) | 1981-09-29 |
Family
ID=9185825
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA295,491A Expired CA1109865A (fr) | 1977-01-24 | 1978-01-23 | Procede de purification d'anthocyanes |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4260388A (en, 2012) |
| JP (1) | JPS53111331A (en, 2012) |
| BE (1) | BE863208A (en, 2012) |
| CA (1) | CA1109865A (en, 2012) |
| DE (1) | DE2802789C3 (en, 2012) |
| ES (1) | ES466253A1 (en, 2012) |
| FR (1) | FR2378040B1 (en, 2012) |
| GB (1) | GB1544402A (en, 2012) |
| GR (1) | GR62641B (en, 2012) |
| IT (1) | IT7847746A0 (en, 2012) |
| NL (1) | NL167456C (en, 2012) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH642990A5 (de) | 1978-07-24 | 1984-05-15 | Parke Davis & Co | Verfahren zum faerben von gelatine fuer kapseln mit hilfe eines gegen den abbau durch licht oder oxidation stabilisierten natuerlichen farbstoffes. |
| US4500556A (en) * | 1982-03-31 | 1985-02-19 | General Foods Corporation | Anthocyanin colorant from grape pomace |
| JPS59223756A (ja) * | 1983-06-02 | 1984-12-15 | San Ei Chem Ind Ltd | アントシアニン色素の製造法 |
| JPS6136364A (ja) * | 1984-07-27 | 1986-02-21 | San Ei Chem Ind Ltd | 色素アントシアニンの精製法 |
| US4775541A (en) * | 1986-09-12 | 1988-10-04 | Mitco Water Laboratories, Inc. | Ion exchange method of treating liquid fermentation products to reduce the content of coloring matter therein |
| DE4005579A1 (de) * | 1990-02-22 | 1991-08-29 | Bayer Ag | Verfahren zum entfaerben und entsalzen von fruchtsaft und -most |
| ZA957770B (en) * | 1995-09-15 | 1996-05-29 | Dipten Putatunda | A process for manufacturing food grade colours from flowers typically hibiscus |
| FR2773150B1 (fr) * | 1997-12-30 | 2000-03-31 | Ferco | Procede d'obtention d'un tanin de raisin, tanin obtenu et utilisations |
| SE525503C2 (sv) * | 2001-11-07 | 2005-03-01 | Biosilvio Munkfors Ab | Förfarande för upprening av anthocyaniner/anthocyanidiner genom användning av hydrofob zeolit |
| WO2006066389A1 (en) | 2004-12-22 | 2006-06-29 | Colarôme Inc. | Natural water-insoluble encapsulation compositions and processes for preparing same |
| RU2360733C1 (ru) * | 2008-06-04 | 2009-07-10 | Государственное образовательное учреждение высшего профессионального образования "Белгородский государственный университет" | Способ получения композиционного сорбента для очистки и концентрирования биологически активных антоцианов из растительного сырья |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1303426A (en) * | 1919-05-13 | Edward j | ||
| US1337673A (en) * | 1917-05-18 | 1920-04-20 | Kalmus Comstock & Wescott Inc | Dye recovery |
| FR1291155A (fr) | 1961-05-13 | 1962-04-20 | Benckiser Gmbh Joh A | Procédé de préparation de colorants naturels à partir de fruits ou autres parties de plantes |
| FR6760M (en, 2012) | 1967-05-30 | 1969-03-03 | ||
| FR2205486B1 (en, 2012) | 1972-11-03 | 1976-01-30 | Anvar Fr | |
| US4082660A (en) * | 1972-11-03 | 1978-04-04 | Agence Nationale De Valorisation De La Recherche | Method of purification |
| FR2299385A1 (fr) | 1975-02-03 | 1976-08-27 | Finedoc Sica Sa | Procede d'extraction des anthocyanes des fruits |
-
1977
- 1977-01-24 FR FR7701890A patent/FR2378040B1/fr not_active Expired
-
1978
- 1978-01-19 US US05/870,856 patent/US4260388A/en not_active Expired - Lifetime
- 1978-01-21 GR GR55230A patent/GR62641B/el unknown
- 1978-01-23 IT IT7847746A patent/IT7847746A0/it unknown
- 1978-01-23 DE DE2802789A patent/DE2802789C3/de not_active Expired
- 1978-01-23 BE BE184548A patent/BE863208A/xx unknown
- 1978-01-23 GB GB2631/78A patent/GB1544402A/en not_active Expired
- 1978-01-23 ES ES466253A patent/ES466253A1/es not_active Expired
- 1978-01-23 NL NL7800799.A patent/NL167456C/xx not_active Application Discontinuation
- 1978-01-23 CA CA295,491A patent/CA1109865A/fr not_active Expired
- 1978-01-24 JP JP586778A patent/JPS53111331A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| NL167456B (nl) | 1981-07-16 |
| GB1544402A (en) | 1979-04-19 |
| DE2802789A1 (de) | 1978-07-27 |
| ES466253A1 (es) | 1978-10-01 |
| JPS5547060B2 (en, 2012) | 1980-11-27 |
| BE863208A (fr) | 1978-07-24 |
| DE2802789B2 (de) | 1979-03-01 |
| FR2378040A1 (en, 2012) | 1978-08-18 |
| JPS53111331A (en) | 1978-09-28 |
| DE2802789C3 (de) | 1979-10-25 |
| FR2378040B1 (en, 2012) | 1981-01-02 |
| US4260388A (en) | 1981-04-07 |
| NL167456C (nl) | 1981-12-16 |
| GR62641B (en) | 1979-05-15 |
| NL7800799A (nl) | 1978-07-26 |
| IT7847746A0 (it) | 1978-01-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |