FI110868B - Förfarande för avskiljning och rening av sekoisolarisiresinoldiglykosid (SDG) från linfrön - Google Patents
Förfarande för avskiljning och rening av sekoisolarisiresinoldiglykosid (SDG) från linfrön Download PDFInfo
- Publication number
- FI110868B FI110868B FI20010127A FI20010127A FI110868B FI 110868 B FI110868 B FI 110868B FI 20010127 A FI20010127 A FI 20010127A FI 20010127 A FI20010127 A FI 20010127A FI 110868 B FI110868 B FI 110868B
- Authority
- FI
- Finland
- Prior art keywords
- sdg
- process according
- lower alcohol
- methanol
- column
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 24
- 235000004426 flaxseed Nutrition 0.000 title claims description 19
- 238000000746 purification Methods 0.000 title description 6
- 238000000926 separation method Methods 0.000 title description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 66
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 35
- 238000000605 extraction Methods 0.000 claims description 19
- MJYQFWSXKFLTAY-OVEQLNGDSA-N (2r,3r)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]butane-1,4-diol;(2r,3r,4s,5s,6r)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O.C1=C(O)C(OC)=CC(C[C@@H](CO)[C@H](CO)CC=2C=C(OC)C(O)=CC=2)=C1 MJYQFWSXKFLTAY-OVEQLNGDSA-N 0.000 claims description 18
- 230000008569 process Effects 0.000 claims description 16
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 8
- 239000006228 supernatant Substances 0.000 claims description 8
- 239000003480 eluent Substances 0.000 claims description 7
- 235000012054 meals Nutrition 0.000 claims description 7
- 239000000843 powder Substances 0.000 claims description 7
- 239000001569 carbon dioxide Substances 0.000 claims description 5
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 5
- 238000003818 flash chromatography Methods 0.000 claims description 5
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 claims description 4
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 238000004587 chromatography analysis Methods 0.000 claims description 3
- 239000002245 particle Substances 0.000 claims description 3
- FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 239000012141 concentrate Substances 0.000 claims 1
- 229940107657 flaxseed extract Drugs 0.000 claims 1
- 235000020704 flaxseed extract Nutrition 0.000 claims 1
- 230000003472 neutralizing effect Effects 0.000 claims 1
- SBVBJPHMDABKJV-PGCJWIIOSA-N secoisolariciresinol diglucoside Chemical compound C1=C(O)C(OC)=CC(C[C@@H](CO[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)[C@H](CO[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)CC=2C=C(OC)C(O)=CC=2)=C1 SBVBJPHMDABKJV-PGCJWIIOSA-N 0.000 description 40
- SBVBJPHMDABKJV-UHFFFAOYSA-N secoisolariciresinol diglycoside Natural products C1=C(O)C(OC)=CC(CC(COC2C(C(O)C(O)C(CO)O2)O)C(COC2C(C(O)C(O)C(CO)O2)O)CC=2C=C(OC)C(O)=CC=2)=C1 SBVBJPHMDABKJV-UHFFFAOYSA-N 0.000 description 40
- 229930013686 lignan Natural products 0.000 description 22
- 235000009408 lignans Nutrition 0.000 description 22
- 150000005692 lignans Chemical class 0.000 description 22
- 235000004431 Linum usitatissimum Nutrition 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- 241000208202 Linaceae Species 0.000 description 7
- 238000002955 isolation Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 241000196324 Embryophyta Species 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 239000003643 water by type Substances 0.000 description 4
- 235000018734 Sambucus australis Nutrition 0.000 description 3
- 244000180577 Sambucus australis Species 0.000 description 3
- 238000013375 chromatographic separation Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 235000013861 fat-free Nutrition 0.000 description 3
- 210000001035 gastrointestinal tract Anatomy 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- OGFXBIXJCWAUCH-UHFFFAOYSA-N meso-secoisolariciresinol Natural products C1=2C=C(O)C(OC)=CC=2CC(CO)C(CO)C1C1=CC=C(O)C(OC)=C1 OGFXBIXJCWAUCH-UHFFFAOYSA-N 0.000 description 3
- 229940056692 resinol Drugs 0.000 description 3
- GRONZTPUWOOUFQ-UHFFFAOYSA-M sodium;methanol;hydroxide Chemical compound [OH-].[Na+].OC GRONZTPUWOOUFQ-UHFFFAOYSA-M 0.000 description 3
- 238000003815 supercritical carbon dioxide extraction Methods 0.000 description 3
- 238000002211 ultraviolet spectrum Methods 0.000 description 3
- DWONJCNDULPHLV-HOTGVXAUSA-N Enterodiol Chemical compound C([C@@H](CO)[C@H](CO)CC=1C=C(O)C=CC=1)C1=CC=CC(O)=C1 DWONJCNDULPHLV-HOTGVXAUSA-N 0.000 description 2
- AOJXPBNHAJMETF-UHFFFAOYSA-N Enterodiol Natural products OCC(Cc1ccc(O)cc1)C(CO)Cc2ccc(O)cc2 AOJXPBNHAJMETF-UHFFFAOYSA-N 0.000 description 2
- HVDGDHBAMCBBLR-UHFFFAOYSA-N Enterolactone Natural products OC1=CC=CC(CC2C(C(=O)OC2)CC=2C=C(O)C=CC=2)=C1 HVDGDHBAMCBBLR-UHFFFAOYSA-N 0.000 description 2
- 239000012675 alcoholic extract Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 150000001720 carbohydrates Chemical group 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- HVDGDHBAMCBBLR-WMLDXEAASA-N enterolactone Chemical compound OC1=CC=CC(C[C@@H]2[C@H](C(=O)OC2)CC=2C=C(O)C=CC=2)=C1 HVDGDHBAMCBBLR-WMLDXEAASA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 229930182470 glycoside Natural products 0.000 description 2
- 150000002338 glycosides Chemical class 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 230000000813 microbial effect Effects 0.000 description 2
- 239000008363 phosphate buffer Substances 0.000 description 2
- 239000003075 phytoestrogen Substances 0.000 description 2
- 238000000194 supercritical-fluid extraction Methods 0.000 description 2
- MATGKVZWFZHCLI-LSDHHAIUSA-N (-)-matairesinol Chemical compound C1=C(O)C(OC)=CC(C[C@@H]2[C@H](C(=O)OC2)CC=2C=C(OC)C(O)=CC=2)=C1 MATGKVZWFZHCLI-LSDHHAIUSA-N 0.000 description 1
- FJBQYOWYDLEAKI-UHFFFAOYSA-N (2,3-dimethyl-4-phenylbutyl)benzene Chemical group C=1C=CC=CC=1CC(C)C(C)CC1=CC=CC=C1 FJBQYOWYDLEAKI-UHFFFAOYSA-N 0.000 description 1
- TWCMVXMQHSVIOJ-UHFFFAOYSA-N Aglycone of yadanzioside D Natural products COC(=O)C12OCC34C(CC5C(=CC(O)C(O)C5(C)C3C(O)C1O)C)OC(=O)C(OC(=O)C)C24 TWCMVXMQHSVIOJ-UHFFFAOYSA-N 0.000 description 1
- PLMKQQMDOMTZGG-UHFFFAOYSA-N Astrantiagenin E-methylester Natural products CC12CCC(O)C(C)(CO)C1CCC1(C)C2CC=C2C3CC(C)(C)CCC3(C(=O)OC)CCC21C PLMKQQMDOMTZGG-UHFFFAOYSA-N 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 240000006240 Linum usitatissimum Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 239000012491 analyte Substances 0.000 description 1
- 230000000922 anti-bactericidal effect Effects 0.000 description 1
- 230000003217 anti-cancerogenic effect Effects 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000008260 defense mechanism Effects 0.000 description 1
- 238000005238 degreasing Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 102000038379 digestive enzymes Human genes 0.000 description 1
- 108091007734 digestive enzymes Proteins 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
- 238000010828 elution Methods 0.000 description 1
- -1 ethanol Chemical compound 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 235000013376 functional food Nutrition 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 239000003163 gonadal steroid hormone Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- PFOARMALXZGCHY-UHFFFAOYSA-N homoegonol Natural products C1=C(OC)C(OC)=CC=C1C1=CC2=CC(CCCO)=CC(OC)=C2O1 PFOARMALXZGCHY-UHFFFAOYSA-N 0.000 description 1
- 230000003054 hormonal effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 239000012633 leachable Substances 0.000 description 1
- 230000003859 lipid peroxidation Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000002101 lytic effect Effects 0.000 description 1
- 235000000055 matairesinol Nutrition 0.000 description 1
- RNXYRAQIZQGUIK-UHFFFAOYSA-N matairesinol Natural products COc1cc(CC2OCC(=O)C2Cc3ccc(O)c(OC)c3)ccc1O RNXYRAQIZQGUIK-UHFFFAOYSA-N 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 239000000401 methanolic extract Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000004808 supercritical fluid chromatography Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 208000019553 vascular disease Diseases 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/18—Acyclic radicals, substituted by carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07G—COMPOUNDS OF UNKNOWN CONSTITUTION
- C07G1/00—Lignin; Lignin derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07G—COMPOUNDS OF UNKNOWN CONSTITUTION
- C07G3/00—Glycosides
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Medicines Containing Plant Substances (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Saccharide Compounds (AREA)
Claims (10)
1. Förfarande för att isolera secoisolarisiresinoldiglykosid (SDG) fran linfrö, kännetecknat därav, att man 20 a) avlägsnar fett frän kallpressat linfrögröpe med superkritisk koldioxidextraktion, b) malar det erhällna, väsentligen fettfria linfrögröpet tili finfördelat pulver, '1 ‘ ‘ c) extraherar SDG frän det erhällna pulvret i en basisk lägalkohol, ' ; d) centrifugerar den erhällna lägalkohollösningen, och neutraliserar supematanten, e) tillvaratar supematanten, som koncentreras och blandas med Cl8-materialet, och ’ ' . 25 avdunstar lösningsmedlet tili närä torrhet, , · · ·. f) fraktionerar den erhällna blandningen flash-kromatografiskt, g) tillvaratar de SDG-rika fraktionema, och : ’ ·, · h) renar de SDG-rika fraktionema i en öppen C18-kolonn. : 1. ·. 30
2. Förfarande enligt patentkravet 1, kännetecknat därav, att man använder lägalkohol som : “1; hjälpmedel för den superkritiska koldioxiden i slutskedet av extraheringen. Π 110868
3. Förfarande enligt patentkravet 2, kännetecknat därav, att lagalkoholen är etanol.
4. Förfarande enligt patentkravet 1, kännetecknat därav, att man i steget b) malar linfrögröpet tili ett pulver med en partikelstorlek av under 0,55 mm. 5
5. Förfarande enligt patentkravet 1, kännetecknat därav, att den basiska lagalkoholen är vattenfri metanol eller etanol, i vilken man har upplöst natriumhydroxid.
6. Förfarande enligt patentkravet 5, kännetecknat därav, att koncentrationen av 10 natriumhydroxid i lagalkoholen är 0,05 - 1 M.
7. Förfarande enligt patentkravet 1, kännetecknat därav, att steget d) utförs antingen sä, att (i) lägalkohollösningen centrifiigeras, varefter supematanten neutraliseras genom att reglera dess pH tili ett värde 6-7 med en stark syra, eller (ii) lägalkohollösningen 15 neutraliseras genom att reglera dess pH tili ett värde 6-7 med en stark syra, och centrifiigeras därefter.
8. Förfarande enligt patentkravet 1, kännetecknat därav, att i steget f) fraktioneras blandningen flash-kromatografiskt med en C18-kolonn genom att använda vatten-metanol 20 eller vatten-etanol som elueringslösning. 1
' 9. Förfarande enligt patentkravet 1, kännetecknat därav, att i steget h) fraktioneras • « » ‘ ; blandningen C18-kromatografiskt i en öppen C18-kolonn genom att använda lagalkohol ... ^ som elueringslösning. 25 ," .
10. Förfarande enligt patentkravet 9, kännetecknat därav, att lagalkoholen är metanol.
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI20010127A FI110868B (sv) | 2001-01-22 | 2001-01-22 | Förfarande för avskiljning och rening av sekoisolarisiresinoldiglykosid (SDG) från linfrön |
| EP02710902A EP1362056A1 (en) | 2001-01-22 | 2002-01-21 | Process for isolating and purifying secoisolarisiresinol diglycoside (sdg) from flaxseed |
| CNB028039807A CN1294140C (zh) | 2001-01-22 | 2002-01-21 | 从亚麻子中分离和提纯开环异落叶松树脂酚二糖苷的方法 |
| PCT/FI2002/000045 WO2002062812A1 (en) | 2001-01-22 | 2002-01-21 | Process for isolating and purifying secoisolarisiresinol diglycoside (sdg) from flaxseed |
| US10/250,912 US20040030108A1 (en) | 2001-01-22 | 2002-01-21 | Process for isolating and purifying secoisolariciresinol diglcoside (sdg) from flaxseed |
| JP2002563164A JP4331482B2 (ja) | 2001-01-22 | 2002-01-21 | 亜麻種子からセコイソラリシレシノールジグリコシド（ｓｄｇ）を単離精製する方法 |
| AU2002229793A AU2002229793B2 (en) | 2001-01-22 | 2002-01-21 | Process for Isolating and Purifying Secoisolariciresinol Diglycoside (SDG) from Flaxseed |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI20010127A FI110868B (sv) | 2001-01-22 | 2001-01-22 | Förfarande för avskiljning och rening av sekoisolarisiresinoldiglykosid (SDG) från linfrön |
| FI20010127 | 2001-01-22 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI20010127A0 FI20010127A0 (sv) | 2001-01-22 |
| FI20010127L FI20010127L (sv) | 2002-07-23 |
| FI110868B true FI110868B (sv) | 2003-04-15 |
Family
ID=8560082
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI20010127A FI110868B (sv) | 2001-01-22 | 2001-01-22 | Förfarande för avskiljning och rening av sekoisolarisiresinoldiglykosid (SDG) från linfrön |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US20040030108A1 (sv) |
| EP (1) | EP1362056A1 (sv) |
| JP (1) | JP4331482B2 (sv) |
| CN (1) | CN1294140C (sv) |
| AU (1) | AU2002229793B2 (sv) |
| FI (1) | FI110868B (sv) |
| WO (1) | WO2002062812A1 (sv) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4684556B2 (ja) * | 2002-03-11 | 2011-05-18 | サントリーホールディングス株式会社 | Ｓｄｇの製法およびその配合飲食物 |
| CN100344642C (zh) * | 2005-04-20 | 2007-10-24 | 中国药科大学 | 亚麻籽木脂素总糖苷提取物的制备方法及其应用 |
| CN100365005C (zh) * | 2006-03-02 | 2008-01-30 | 江南大学 | 一种从亚麻籽中提取纯化开环异落叶松树脂酚二葡萄糖苷的方法 |
| CN100395222C (zh) * | 2006-05-12 | 2008-06-18 | 中国科学院山西煤炭化学研究所 | 一种由亚麻籽制备脱水开环异落叶松树脂酚的方法 |
| CN100395253C (zh) * | 2006-05-12 | 2008-06-18 | 中国科学院山西煤炭化学研究所 | 一种由亚麻籽制备开环异落叶松树脂酚二葡萄糖苷的方法 |
| CN101117641B (zh) * | 2007-07-27 | 2011-05-11 | 大连医诺生物有限公司 | 开环异落叶松树脂酚二葡萄糖苷的制备方法 |
| CN101139373B (zh) * | 2007-07-31 | 2010-12-29 | 中国科学院过程工程研究所 | 一种快速规模化提取和纯化亚麻木酚素的方法 |
| CN101759731B (zh) * | 2008-12-25 | 2011-10-19 | 中国科学院兰州化学物理研究所 | 亚麻籽胶和开环异落叶松树脂酚二葡萄糖苷的提取方法 |
| CN101723993A (zh) * | 2009-11-16 | 2010-06-09 | 山东大学威海分校 | 从亚麻籽皮中提取亚麻木酚素的方法 |
| CN102914601B (zh) * | 2012-09-03 | 2014-05-21 | 内蒙古大学 | 一种亚麻籽产品中有益及有害成分的检测方法 |
| CN102796148A (zh) * | 2012-09-13 | 2012-11-28 | 上海红马饲料有限公司 | 从亚麻饼粕中提取、分离和纯化亚麻木酚素的方法 |
| JP6321788B2 (ja) * | 2013-06-10 | 2018-05-09 | ザ トラスティーズ オブ ザ ユニバーシティ オブ ペンシルバニア | （ｓ，ｓ）−セコイソラリシレジノールジグルコシド及び（ｒ，ｒ）−セコイソラリシレジノールジグルコシドの製造 |
| CN103396461B (zh) * | 2013-08-12 | 2016-03-02 | 白心亮 | 一种亚麻木酚素的分离提纯方法 |
| CN103835005A (zh) * | 2013-12-08 | 2014-06-04 | 姜著川 | 一种罗布麻闪爆和超临界二氧化碳流体联合脱胶方法 |
| TWI849471B (zh) | 2017-05-24 | 2024-07-21 | 英商安諾特克有限公司 | 用於控制諧振器之裝置及方法 |
| US11909400B2 (en) | 2019-12-05 | 2024-02-20 | Anlotek Limited | Use of stable tunable active feedback analog filters in frequency synthesis |
| EP3890189A1 (en) | 2020-03-30 | 2021-10-06 | Anlotek Limited | Active feedback analog filters with coupled resonators |
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| US11955942B2 (en) | 2021-02-27 | 2024-04-09 | Anlotek Limited | Active multi-pole filter |
| EP4084333A1 (en) * | 2021-04-30 | 2022-11-02 | Anlotek Limited | Phase noise reduction in a variable analogue rf resonator with switched fixed value capacitors |
| WO2023041437A1 (en) | 2021-09-14 | 2023-03-23 | Basf Se | An extract of linum usitatissimum seeds |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US4495207A (en) * | 1982-10-25 | 1985-01-22 | The United States Of America As Represented By The Secretary Of Agriculture | Production of food-grade corn germ product by supercritical fluid extraction |
| US4493854A (en) * | 1983-09-20 | 1985-01-15 | The United States Of America As Represented By The Secretary Of Agriculture | Production of defatted soybean products by supercritical fluid extraction |
| US5705618A (en) * | 1995-03-31 | 1998-01-06 | Agriculture And Agri-Food Canada | Process for extracting lignans from flaxseed |
| US6264853B1 (en) * | 1999-06-21 | 2001-07-24 | Agriculture And Agri-Food Canada | Complex containing lignan, phenolic and aliphatic substances from flax and process for preparing |
-
2001
- 2001-01-22 FI FI20010127A patent/FI110868B/sv not_active IP Right Cessation
-
2002
- 2002-01-21 WO PCT/FI2002/000045 patent/WO2002062812A1/en active Application Filing
- 2002-01-21 EP EP02710902A patent/EP1362056A1/en not_active Withdrawn
- 2002-01-21 US US10/250,912 patent/US20040030108A1/en not_active Abandoned
- 2002-01-21 AU AU2002229793A patent/AU2002229793B2/en not_active Ceased
- 2002-01-21 CN CNB028039807A patent/CN1294140C/zh not_active Expired - Fee Related
- 2002-01-21 JP JP2002563164A patent/JP4331482B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| FI20010127L (sv) | 2002-07-23 |
| WO2002062812A1 (en) | 2002-08-15 |
| CN1294140C (zh) | 2007-01-10 |
| AU2002229793B2 (en) | 2006-04-27 |
| EP1362056A1 (en) | 2003-11-19 |
| CN1487948A (zh) | 2004-04-07 |
| JP2004518705A (ja) | 2004-06-24 |
| JP4331482B2 (ja) | 2009-09-16 |
| FI20010127A0 (sv) | 2001-01-22 |
| US20040030108A1 (en) | 2004-02-12 |
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