TR201912820A2 - Karnosi̇k asi̇t, karnosol ve rozmari̇ni̇k asi̇t i̇zolasyon yöntemi̇ - Google Patents
Karnosi̇k asi̇t, karnosol ve rozmari̇ni̇k asi̇t i̇zolasyon yöntemi̇Info
- Publication number
- TR201912820A2 TR201912820A2 TR2019/12820A TR201912820A TR201912820A2 TR 201912820 A2 TR201912820 A2 TR 201912820A2 TR 2019/12820 A TR2019/12820 A TR 2019/12820A TR 201912820 A TR201912820 A TR 201912820A TR 201912820 A2 TR201912820 A2 TR 201912820A2
- Authority
- TR
- Turkey
- Prior art keywords
- acid
- carnosol
- carnosic
- extract
- rosmarinic acid
- Prior art date
Links
- 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 title abstract 12
- DOUMFZQKYFQNTF-WUTVXBCWSA-N (R)-rosmarinic acid Chemical compound C([C@H](C(=O)O)OC(=O)\C=C\C=1C=C(O)C(O)=CC=1)C1=CC=C(O)C(O)=C1 DOUMFZQKYFQNTF-WUTVXBCWSA-N 0.000 title abstract 8
- 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 title abstract 4
- MMFRMKXYTWBMOM-UHFFFAOYSA-N Carnosol Natural products CCc1cc2C3CC4C(C)(C)CCCC4(C(=O)O3)c2c(O)c1O MMFRMKXYTWBMOM-UHFFFAOYSA-N 0.000 title abstract 4
- ZZAFFYPNLYCDEP-HNNXBMFYSA-N Rosmarinsaeure Natural products OC(=O)[C@H](Cc1cccc(O)c1O)OC(=O)C=Cc2ccc(O)c(O)c2 ZZAFFYPNLYCDEP-HNNXBMFYSA-N 0.000 title abstract 4
- 235000004654 carnosol Nutrition 0.000 title abstract 4
- DOUMFZQKYFQNTF-MRXNPFEDSA-N rosemarinic acid Natural products C([C@H](C(=O)O)OC(=O)C=CC=1C=C(O)C(O)=CC=1)C1=CC=C(O)C(O)=C1 DOUMFZQKYFQNTF-MRXNPFEDSA-N 0.000 title abstract 4
- TVHVQJFBWRLYOD-UHFFFAOYSA-N rosmarinic acid Natural products OC(=O)C(Cc1ccc(O)c(O)c1)OC(=Cc2ccc(O)c(O)c2)C=O TVHVQJFBWRLYOD-UHFFFAOYSA-N 0.000 title abstract 4
- 238000002955 isolation Methods 0.000 title 1
- 238000000034 method Methods 0.000 abstract 4
- 230000003078 antioxidant effect Effects 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- 241001529742 Rosmarinus Species 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 238000004440 column chromatography Methods 0.000 abstract 1
- 239000002537 cosmetic Substances 0.000 abstract 1
- 238000004332 deodorization Methods 0.000 abstract 1
- 229930004069 diterpene Natural products 0.000 abstract 1
- 125000000567 diterpene group Chemical group 0.000 abstract 1
- 238000001035 drying Methods 0.000 abstract 1
- 239000000945 filler Substances 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 238000005374 membrane filtration Methods 0.000 abstract 1
- 230000020477 pH reduction Effects 0.000 abstract 1
- 150000007965 phenolic acids Chemical class 0.000 abstract 1
- 239000000843 powder Substances 0.000 abstract 1
- 238000001556 precipitation Methods 0.000 abstract 1
- 229940092258 rosemary extract Drugs 0.000 abstract 1
- 235000020748 rosemary extract Nutrition 0.000 abstract 1
- 239000001233 rosmarinus officinalis l. extract Substances 0.000 abstract 1
- 238000000926 separation method Methods 0.000 abstract 1
Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/365—Lactones
- A61K31/366—Lactones having six-membered rings, e.g. delta-lactones
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
- B01D15/08—Selective adsorption, e.g. chromatography
- B01D15/26—Selective adsorption, e.g. chromatography characterised by the separation mechanism
- B01D15/265—Adsorption chromatography
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/192—Carboxylic acids, e.g. valproic acid having aromatic groups, e.g. sulindac, 2-aryl-propionic acids, ethacrynic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/216—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acids having aromatic rings, e.g. benactizyne, clofibrate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/53—Lamiaceae or Labiatae (Mint family), e.g. thyme, rosemary or lavender
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/53—Lamiaceae or Labiatae (Mint family), e.g. thyme, rosemary or lavender
- A61K36/537—Salvia (sage)
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D11/00—Solvent extraction
- B01D11/02—Solvent extraction of solids
- B01D11/028—Flow sheets
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D11/00—Solvent extraction
- B01D11/02—Solvent extraction of solids
- B01D11/0288—Applications, solvents
-
- 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
- C07C51/47—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/56—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
-
- 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
- C07D493/08—Bridged systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D11/00—Solvent extraction
- B01D11/02—Solvent extraction of solids
- B01D11/0261—Solvent extraction of solids comprising vibrating mechanisms, e.g. mechanical, acoustical
- B01D11/0265—Applying ultrasound
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biotechnology (AREA)
- Mycology (AREA)
- Microbiology (AREA)
- Medical Informatics (AREA)
- Botany (AREA)
- Alternative & Traditional Medicine (AREA)
- Emergency Medicine (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
Abstract
Buluş Biberiye bitkisinin antioksidan özelliğe sahip etken maddeleri olarak tanımlanan diterpenler olan karnosik asit ve karnosol ile fenolik asit olan rozmarinik asitin, kolon kromatografi yöntemiyle, fraksiyonlanarak ayrılması yöntemi ile ilgilidir. Üretim prosesi; uygun çözgen içinde elde edilen biberiye ekstresinin uygun dolgu maddesiyle doldurulmuş kolondan çözgen geçirerek karnosik asit ve karnosolce zengin kısmın ayrılmasını ve sonrasında kurutularak, deodorize toz ürün elde edilmesini kapsar. Proses sırasında yüksek antioksidan aktiviteye sahip rozmarinik asit içeren ekstre de elde edilmektedir. Buluş, bu şekliyle asitlendirme, çöktürme, membran filtrasyonu ve deodorizasyon gibi ek işlemlere gerek duymadan ve tek seferde elde edilen karnosik asit ve karnosolce zengin ekstrenin, rozmarinik asit içeren ekstrenin gıda, ilaç ve kozmetik uygulamalarında kullanımına izin verir.
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
TR2019/12820A TR201912820A2 (tr) | 2019-08-26 | 2019-08-26 | Karnosi̇k asi̇t, karnosol ve rozmari̇ni̇k asi̇t i̇zolasyon yöntemi̇ |
EP20756966.6A EP4021607B1 (en) | 2019-08-26 | 2020-07-29 | Carnosic acid, carnosol and rosmarinic acid isolation method |
PCT/IB2020/057159 WO2021038340A1 (en) | 2019-08-26 | 2020-07-29 | Carnosic acid, carnosol and rosmarinic acid isolation method |
US17/638,067 US20220313655A1 (en) | 2019-08-26 | 2020-07-29 | Carnosic acid, carnosol and rosmarinic acid isolation method |
ES20756966T ES2972699T3 (es) | 2019-08-26 | 2020-07-29 | Procedimiento de aislamiento de ácido carnósico, de carnosol y de ácido rosmarínico |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
TR2019/12820A TR201912820A2 (tr) | 2019-08-26 | 2019-08-26 | Karnosi̇k asi̇t, karnosol ve rozmari̇ni̇k asi̇t i̇zolasyon yöntemi̇ |
Publications (1)
Publication Number | Publication Date |
---|---|
TR201912820A2 true TR201912820A2 (tr) | 2021-03-22 |
Family
ID=72086927
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
TR2019/12820A TR201912820A2 (tr) | 2019-08-26 | 2019-08-26 | Karnosi̇k asi̇t, karnosol ve rozmari̇ni̇k asi̇t i̇zolasyon yöntemi̇ |
Country Status (5)
Country | Link |
---|---|
US (1) | US20220313655A1 (tr) |
EP (1) | EP4021607B1 (tr) |
ES (1) | ES2972699T3 (tr) |
TR (1) | TR201912820A2 (tr) |
WO (1) | WO2021038340A1 (tr) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN113461531A (zh) * | 2021-06-09 | 2021-10-01 | 湖南鑫利生物科技有限公司 | 一种提取迷迭香酸的方法 |
CN114736123B (zh) * | 2021-12-28 | 2023-10-03 | 海南舒普生物科技有限公司 | 一种高纯度迷迭香酸的提取方法 |
CN114773425B (zh) * | 2022-06-07 | 2024-01-26 | 晨光生物科技集团股份有限公司 | 一种液液萃取分离鼠尾草酸和熊果酸的方法与应用 |
CN115724901A (zh) * | 2022-12-09 | 2023-03-03 | 湖南一科生物科技有限公司 | 一种从迷迭香中提取迷迭香酸、鼠尾草酸和熊果酸的方法 |
Family Cites Families (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3950266A (en) | 1973-11-28 | 1976-04-13 | Rutgers Research And Educational Foundation | Method of producing an antioxidant composition from rosemary and sage |
ATE111434T1 (de) | 1990-10-06 | 1994-09-15 | Nestle Sa | Verfahren zur gewinnung von carnosäure. |
CA2220223C (en) | 1995-05-05 | 2008-07-29 | Hauser Inc. | High purity carnosic acid from rosemary and sage extracts by ph-controlled precipitation |
US6855349B2 (en) | 1998-12-07 | 2005-02-15 | Kemin Industries, Inc. | Method for simultaneous extraction of essential oils and antioxidants from Labiatae species and the extract products thereof |
SI20143B (sl) | 1999-02-16 | 2008-04-30 | Vitiva Prizvodnja In Storitve D.D. | Postopek za pridobivanje naravnih antioksidantov iz rastlin |
CN102199092A (zh) * | 2010-03-26 | 2011-09-28 | 禹州市森源本草天然产物有限公司 | 一种从迷迭香获得两种抗氧化剂的生产工艺 |
ES2581592T3 (es) | 2010-10-25 | 2016-09-06 | Kalamazoo Holdings, Inc. | Procedimiento sencillo para producir y separar composiciones aromatizantes antioxidantes solubles en aceite y solubles en agua de hierbas de Labiatae usando disolventes verdes |
CN102115442B (zh) * | 2011-01-05 | 2013-10-16 | 曾健青 | 一种从迷迭香叶提取物中分离鼠尾草酸的方法 |
CN102432469B (zh) | 2011-12-08 | 2013-02-20 | 长沙卫一生物科技有限公司 | 一种从迷迭香中提取分离迷迭香酸和熊果酸的方法 |
CN103319495B (zh) * | 2013-07-20 | 2016-03-02 | 高政 | 高纯度鼠尾草酚的制备方法 |
CN104939267B (zh) * | 2014-03-25 | 2019-07-23 | 湖南今汉药业有限公司 | 一种迷迭香提取组合物及其作为保鲜剂的应用 |
CN108070453A (zh) | 2016-11-11 | 2018-05-25 | 长沙卫生物科技有限公司 | 一种从迷迭香中提取分离迷迭香精油、迷迭香酸、熊果酸和鼠尾草酸的方法 |
CN108338406B (zh) * | 2018-02-13 | 2020-07-28 | 玉溪开元金蓝生物科技有限责任公司 | 一种迷迭香抗氧化剂爆珠及其在卷烟滤棒中的应用 |
CN108420849A (zh) * | 2018-03-19 | 2018-08-21 | 启东创绿绿化工程有限公司 | 一种制备迷迭香提取物的方法 |
-
2019
- 2019-08-26 TR TR2019/12820A patent/TR201912820A2/tr unknown
-
2020
- 2020-07-29 EP EP20756966.6A patent/EP4021607B1/en active Active
- 2020-07-29 ES ES20756966T patent/ES2972699T3/es active Active
- 2020-07-29 US US17/638,067 patent/US20220313655A1/en active Pending
- 2020-07-29 WO PCT/IB2020/057159 patent/WO2021038340A1/en active Search and Examination
Also Published As
Publication number | Publication date |
---|---|
US20220313655A1 (en) | 2022-10-06 |
EP4021607B1 (en) | 2023-11-15 |
WO2021038340A1 (en) | 2021-03-04 |
ES2972699T3 (es) | 2024-06-14 |
EP4021607A1 (en) | 2022-07-06 |
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