NO314627B1 - Fremgangsmåte for fremstilling av stabilisert karnosinsyre i höy konsentrasjon - Google Patents
Fremgangsmåte for fremstilling av stabilisert karnosinsyre i höy konsentrasjon Download PDFInfo
- Publication number
- NO314627B1 NO314627B1 NO19994852A NO994852A NO314627B1 NO 314627 B1 NO314627 B1 NO 314627B1 NO 19994852 A NO19994852 A NO 19994852A NO 994852 A NO994852 A NO 994852A NO 314627 B1 NO314627 B1 NO 314627B1
- Authority
- NO
- Norway
- Prior art keywords
- acid
- carnosic acid
- concentration
- aqueous solution
- aqueous
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 36
- 239000002253 acid Substances 0.000 title claims description 18
- 230000008569 process Effects 0.000 title claims description 15
- QRYRORQUOLYVBU-VBKZILBWSA-N carnosic acid Chemical compound CC([C@@H]1CC2)(C)CCC[C@]1(C(O)=O)C1=C2C=C(C(C)C)C(O)=C1O QRYRORQUOLYVBU-VBKZILBWSA-N 0.000 claims description 123
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 48
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 24
- 239000012071 phase Substances 0.000 claims description 24
- 238000000605 extraction Methods 0.000 claims description 22
- 241001529742 Rosmarinus Species 0.000 claims description 20
- 239000000243 solution Substances 0.000 claims description 15
- 239000003921 oil Substances 0.000 claims description 13
- 235000019198 oils Nutrition 0.000 claims description 13
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 12
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 12
- 239000008158 vegetable oil Substances 0.000 claims description 12
- 125000005233 alkylalcohol group Chemical group 0.000 claims description 10
- 239000007864 aqueous solution Substances 0.000 claims description 10
- 229910021538 borax Inorganic materials 0.000 claims description 8
- AJFXNBUVIBKWBT-UHFFFAOYSA-N disodium;boric acid;hydrogen borate Chemical compound [Na+].[Na+].OB(O)O.OB(O)O.OB(O)O.OB([O-])[O-] AJFXNBUVIBKWBT-UHFFFAOYSA-N 0.000 claims description 8
- 235000010339 sodium tetraborate Nutrition 0.000 claims description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 239000008346 aqueous phase Substances 0.000 claims description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 2
- 235000019441 ethanol Nutrition 0.000 claims 4
- 239000007853 buffer solution Substances 0.000 claims 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims 1
- 239000012062 aqueous buffer Substances 0.000 claims 1
- 239000007790 solid phase Substances 0.000 claims 1
- 239000000284 extract Substances 0.000 description 11
- 239000002028 Biomass Substances 0.000 description 9
- 238000003828 vacuum filtration Methods 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 7
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000000872 buffer Substances 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- 230000003078 antioxidant effect Effects 0.000 description 3
- 239000011668 ascorbic acid Substances 0.000 description 3
- 235000010323 ascorbic acid Nutrition 0.000 description 3
- 229960005070 ascorbic acid Drugs 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000008601 oleoresin Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- XUSYGBPHQBWGAD-PJSUUKDQSA-N Carnosol Chemical compound CC([C@@H]1C2)(C)CCC[C@@]11C(=O)O[C@@H]2C2=C1C(O)=C(O)C(C(C)C)=C2 XUSYGBPHQBWGAD-PJSUUKDQSA-N 0.000 description 1
- MMFRMKXYTWBMOM-UHFFFAOYSA-N Carnosol Natural products CCc1cc2C3CC4C(C)(C)CCCC4(C(=O)O3)c2c(O)c1O MMFRMKXYTWBMOM-UHFFFAOYSA-N 0.000 description 1
- 241001530490 Salvia rosmarinus Species 0.000 description 1
- 244000182022 Salvia sclarea Species 0.000 description 1
- 241000295644 Staphylococcaceae Species 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 235000004654 carnosol Nutrition 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 208000002925 dental caries Diseases 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 229930004069 diterpene Natural products 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- -1 phenolic diterpene Chemical class 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000003244 pro-oxidative effect Effects 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 235000015639 rosmarinus officinalis Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/48—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Plant Substances (AREA)
- Saccharide Compounds (AREA)
- Fats And Perfumes (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Compounds Of Unknown Constitution (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO19994852A NO314627B1 (no) | 1997-04-16 | 1999-09-23 | Fremgangsmåte for fremstilling av stabilisert karnosinsyre i höy konsentrasjon |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/IL1997/000125 WO1998046554A1 (en) | 1997-04-16 | 1997-04-16 | A novel process to produce stabilized carnosic acid in high concentration |
| NO19994852A NO314627B1 (no) | 1997-04-16 | 1999-09-23 | Fremgangsmåte for fremstilling av stabilisert karnosinsyre i höy konsentrasjon |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO994852D0 NO994852D0 (no) | 1999-09-23 |
| NO994852L NO994852L (no) | 1999-11-24 |
| NO314627B1 true NO314627B1 (no) | 2003-04-22 |
Family
ID=11061993
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19994852A NO314627B1 (no) | 1997-04-16 | 1999-09-23 | Fremgangsmåte for fremstilling av stabilisert karnosinsyre i höy konsentrasjon |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US6335373B1 (de) |
| EP (1) | EP0975572B1 (de) |
| JP (1) | JP2001518072A (de) |
| AT (1) | ATE255556T1 (de) |
| AU (1) | AU726687B2 (de) |
| BR (1) | BR9714605A (de) |
| CA (1) | CA2286801C (de) |
| DE (1) | DE69726612T2 (de) |
| ES (1) | ES2210511T3 (de) |
| IL (1) | IL132370A0 (de) |
| NO (1) | NO314627B1 (de) |
| WO (1) | WO1998046554A1 (de) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE390852T1 (de) * | 2001-09-19 | 2008-04-15 | Conagra Grocery Prod Co | Verfahren zur herstellung von tomatenpaste durch fraktionierung und konzentrierung |
| US20050260313A1 (en) * | 2004-05-21 | 2005-11-24 | Conagra Grocery Products Company | Method for producing tomato paste and powder using reverse osmosis and evaporation |
| CA2666461A1 (en) * | 2006-10-10 | 2008-09-12 | Burnham Institute For Medical Research | Neuroprotective compositions and methods |
| US20100040758A1 (en) * | 2006-12-28 | 2010-02-18 | Chitra Vasant Savngikar | Integrated production of phytochemical rich plant products or isolates from green vegetation |
| US9220295B2 (en) * | 2010-12-01 | 2015-12-29 | R.J. Reynolds Tobacco Company | Tobacco separation process for extracting tobacco-derived materials, and associated extraction systems |
| CN102604640B (zh) * | 2011-01-19 | 2014-02-26 | 广州合诚三先生物科技有限公司 | 迷迭香的综合提取与制备脂溶性速溶抗氧化剂的方法 |
| ITGE20110041A1 (it) * | 2011-04-12 | 2012-10-13 | Ct Di Sperimentazione Ed Assist Enza Agricola | Metodo di ottenimento di acido carnosico e triterpeni, come composti puri o come fitocomplessi arricchiti, da piante della famiglia delle lamiaceae |
| JP6344597B2 (ja) * | 2014-03-27 | 2018-06-20 | シーシーアイホールディングス株式会社 | 細胞増殖抑制剤 |
| GB201717712D0 (en) * | 2017-10-27 | 2017-12-13 | Naturex Sa | Compositions |
| CN110467528A (zh) * | 2019-08-23 | 2019-11-19 | 吴俊� | 一种从迷迭香中提取鼠尾草酸的方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2124706A (en) | 1935-03-14 | 1938-07-26 | Nat Biscuit Co | Stabilized fats and method for preventing rancidity |
| CH579354A5 (de) * | 1973-10-26 | 1976-09-15 | Nestle Sa | |
| JPS5675066A (en) | 1979-11-24 | 1981-06-20 | Lion Corp | Production of fried food |
| US4450097A (en) | 1981-02-26 | 1984-05-22 | Lion Corporation | Antioxidative compound, method of extracting same from rosemary, and use of same |
| US4450047A (en) | 1983-01-28 | 1984-05-22 | Penwalt Corporation | Process for recovering anhydrous alkanesulfonic acids by reduced pressure, falling film evaporation |
| CA1297718C (en) * | 1985-12-20 | 1992-03-24 | Paul H. Todd, Jr. | Herb flavoring and/or antioxidant composition and process |
| ATE184789T1 (de) * | 1990-10-06 | 1999-10-15 | Nestle Sa | Verwendung von carnosolsäure wegen seiner anticarcinogenen und antiviralen eigenschaften |
| CA2119265C (en) | 1991-09-20 | 2001-03-20 | Uy Nguyen | Antioxidant oleoresin compositions and a process for their production |
| CA2220223C (en) * | 1995-05-05 | 2008-07-29 | Hauser Inc. | High purity carnosic acid from rosemary and sage extracts by ph-controlled precipitation |
-
1997
- 1997-04-16 US US09/403,099 patent/US6335373B1/en not_active Expired - Lifetime
- 1997-04-16 WO PCT/IL1997/000125 patent/WO1998046554A1/en not_active Application Discontinuation
- 1997-04-16 IL IL13237097A patent/IL132370A0/xx unknown
- 1997-04-16 EP EP97915667A patent/EP0975572B1/de not_active Expired - Lifetime
- 1997-04-16 ES ES97915667T patent/ES2210511T3/es not_active Expired - Lifetime
- 1997-04-16 DE DE69726612T patent/DE69726612T2/de not_active Expired - Lifetime
- 1997-04-16 BR BR9714605-6A patent/BR9714605A/pt unknown
- 1997-04-16 CA CA002286801A patent/CA2286801C/en not_active Expired - Fee Related
- 1997-04-16 AU AU23059/97A patent/AU726687B2/en not_active Ceased
- 1997-04-16 JP JP51106798A patent/JP2001518072A/ja active Pending
- 1997-04-16 AT AT97915667T patent/ATE255556T1/de not_active IP Right Cessation
-
1999
- 1999-09-23 NO NO19994852A patent/NO314627B1/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US6335373B1 (en) | 2002-01-01 |
| NO994852L (no) | 1999-11-24 |
| NO994852D0 (no) | 1999-09-23 |
| DE69726612D1 (de) | 2004-01-15 |
| JP2001518072A (ja) | 2001-10-09 |
| BR9714605A (pt) | 2002-05-21 |
| AU2305997A (en) | 1998-11-11 |
| IL132370A0 (en) | 2001-03-19 |
| EP0975572B1 (de) | 2003-12-03 |
| AU726687B2 (en) | 2000-11-16 |
| DE69726612T2 (de) | 2004-09-16 |
| ES2210511T3 (es) | 2004-07-01 |
| WO1998046554A1 (en) | 1998-10-22 |
| EP0975572A1 (de) | 2000-02-02 |
| CA2286801C (en) | 2006-03-14 |
| CA2286801A1 (en) | 1998-10-22 |
| ATE255556T1 (de) | 2003-12-15 |
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