RU2001129789A - Способ получения оксида линалоола или содержащих оксид линалоола смесей - Google Patents
Способ получения оксида линалоола или содержащих оксид линалоола смесей Download PDFInfo
- Publication number
- RU2001129789A RU2001129789A RU2001129789/13A RU2001129789A RU2001129789A RU 2001129789 A RU2001129789 A RU 2001129789A RU 2001129789/13 A RU2001129789/13 A RU 2001129789/13A RU 2001129789 A RU2001129789 A RU 2001129789A RU 2001129789 A RU2001129789 A RU 2001129789A
- Authority
- RU
- Russia
- Prior art keywords
- linalool
- enzymes
- oxidizing agent
- linalool oxide
- solvent
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 22
- 239000001278 2-(5-ethenyl-5-methyloxolan-2-yl)propan-2-ol Substances 0.000 title claims 5
- BRHDDEIRQPDPMG-UHFFFAOYSA-N Linalyl oxide Chemical compound CC(C)(O)C1CCC(C)(C=C)O1 BRHDDEIRQPDPMG-UHFFFAOYSA-N 0.000 title claims 5
- 239000000203 mixture Substances 0.000 title claims 4
- 108090000790 Enzymes Proteins 0.000 claims 7
- 102000004190 Enzymes Human genes 0.000 claims 7
- 229940088598 enzyme Drugs 0.000 claims 7
- 239000007800 oxidant agent Substances 0.000 claims 6
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 claims 4
- CDOSHBSSFJOMGT-JTQLQIEISA-N (R)-linalool Natural products CC(C)=CCC[C@@](C)(O)C=C CDOSHBSSFJOMGT-JTQLQIEISA-N 0.000 claims 4
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 claims 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- 239000012429 reaction media Substances 0.000 claims 3
- 239000002904 solvent Substances 0.000 claims 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 2
- 239000004366 Glucose oxidase Substances 0.000 claims 2
- 108010015776 Glucose oxidase Proteins 0.000 claims 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims 2
- 241001661345 Moesziomyces antarcticus Species 0.000 claims 2
- 240000004808 Saccharomyces cerevisiae Species 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- 229940116332 glucose oxidase Drugs 0.000 claims 2
- 235000019420 glucose oxidase Nutrition 0.000 claims 2
- 229930007744 linalool Natural products 0.000 claims 2
- 230000003647 oxidation Effects 0.000 claims 2
- 238000007254 oxidation reaction Methods 0.000 claims 2
- 241000894006 Bacteria Species 0.000 claims 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims 1
- 241001373560 Humicola sp. Species 0.000 claims 1
- 239000004367 Lipase Substances 0.000 claims 1
- 102000004882 Lipase Human genes 0.000 claims 1
- 108090001060 Lipase Proteins 0.000 claims 1
- 241000589774 Pseudomonas sp. Species 0.000 claims 1
- 241000235403 Rhizomucor miehei Species 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 150000001733 carboxylic acid esters Chemical class 0.000 claims 1
- 235000019421 lipase Nutrition 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 239000000341 volatile oil Substances 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
- C12N9/14—Hydrolases (3)
- C12N9/16—Hydrolases (3) acting on ester bonds (3.1)
- C12N9/18—Carboxylic ester hydrolases (3.1.1)
- C12N9/20—Triglyceride splitting, e.g. by means of lipase
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/02—Oxygen as only ring hetero atoms
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/205—Heterocyclic compounds
- A23L27/2052—Heterocyclic compounds having oxygen or sulfur as the only hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/12—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/10—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0069—Heterocyclic compounds
- C11B9/0073—Heterocyclic compounds containing only O or S as heteroatoms
- C11B9/0076—Heterocyclic compounds containing only O or S as heteroatoms the hetero rings containing less than six atoms
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0069—Heterocyclic compounds
- C11B9/0073—Heterocyclic compounds containing only O or S as heteroatoms
- C11B9/008—Heterocyclic compounds containing only O or S as heteroatoms the hetero rings containing six atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Zoology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Genetics & Genomics (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Microbiology (AREA)
- Biotechnology (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Nutrition Science (AREA)
- Medicinal Chemistry (AREA)
- Biomedical Technology (AREA)
- General Chemical & Material Sciences (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Seasonings (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Claims (18)
1. Способ получения оксида линалоола или содержащих оксид линалоола смесей, отличающийся тем, что линалоол или линалоолсодержащие смеси окисляют в присутствии фермента.
2. Способ по п.1, отличающийся тем, что используют D-линалоол, L-линалоол или эфирные масла, содержащие D-линалоол или L-линалоол, или смеси этих веществ.
3. Способ по одному из п.1 или 2, отличающийся тем, что используют ферменты из дрожжей или бактерий.
4. Способ по одному из пп.1-3, отличающийся тем, что используют ферменты из видов Candida antarctica, Pseudomonas sp., Humicola sp., Mucor miehei или смешанные культуры с этими дрожжами.
5. Способ по одному из пп.1-4, отличающийся тем, что используют ферменты из Candida antarctica.
6. Способ по одному из пп.1-5, отличающийся тем, что в качестве ферментов используют липазы.
7. Способ по одному из пп.1-6, отличающийся тем, что окисление проводят в присутствии одного или нескольких окислителей.
8. Способ по одному из пп.1-7, отличающийся тем, что окислитель добавляют до или во время проведения способа.
9. Способ по одному из пп.1-8, отличающийся тем, что окислитель получают в реакционной среде до или во время проведения способа.
10. Способ по одному из пп.1-9, отличающийся тем, что окислитель получают в присутствии катализатора до или во время процесса окисления.
11. Способ по п.10, отличающийся тем, что в качестве катализаторов используют ферменты.
12. Способ по п.11, отличающийся тем, что в качестве фермента используют глюкозооксидазу (GOD).
13. Способ по одному из пп.7-12, отличающийся тем, что окислитель добавляют в реакционную среду в количестве от 0,1 до 80%.
14. Способ по одному из пп.1-13, отличающийся тем, что в качестве окислителя используют пероксид водорода.
15. Способ по одному из пп.1-14, отличающийся тем, что в реакционную среду добавляют растворитель.
16. Способ по одному из пп.1-15, отличающийся тем, что в качестве растворителя используют карбоновую кислоту или эфиры карбоновой кислоты.
17. Способ по одному из пп.1-16, отличающийся тем. что в качестве растворителя используют этиловый эфир уксусной кислоты или уксусную кислоту.
18. Оксид линалоола, полученный способом по одному из пп.1-15.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10055092A DE10055092A1 (de) | 2000-11-07 | 2000-11-07 | Verfahren zur Herstellung von Linalooloxid oder von Linalooloxid enthaltenden Gemischen |
| DE10055092.4 | 2000-11-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2001129789A true RU2001129789A (ru) | 2003-10-10 |
Family
ID=7662395
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2001129789/13A RU2001129789A (ru) | 2000-11-07 | 2001-11-06 | Способ получения оксида линалоола или содержащих оксид линалоола смесей |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US6703218B2 (ru) |
| EP (1) | EP1205544A3 (ru) |
| JP (1) | JP2002191391A (ru) |
| KR (1) | KR20020035755A (ru) |
| CN (1) | CN1396262A (ru) |
| AU (1) | AU8922401A (ru) |
| BR (1) | BR0105071A (ru) |
| CA (1) | CA2361184A1 (ru) |
| DE (1) | DE10055092A1 (ru) |
| EE (1) | EE200100588A (ru) |
| HU (1) | HUP0104565A2 (ru) |
| IL (1) | IL146344A0 (ru) |
| MX (1) | MXPA01011280A (ru) |
| PL (1) | PL350512A1 (ru) |
| RU (1) | RU2001129789A (ru) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1925826A (zh) * | 2003-05-08 | 2007-03-07 | 弗莱克特瑞尔公司 | 新型芳香衍生物 |
| JP2008133233A (ja) * | 2006-11-29 | 2008-06-12 | Noevir Co Ltd | Ｗｎｔ５ａ産生促進剤、養毛剤 |
| EP2075320A1 (de) * | 2007-12-17 | 2009-07-01 | Symrise GmbH & Co. KG | Verfahren zur Herstellung eines Aromakonzentrates sowie ein Aromakonzentrat |
| US8158180B2 (en) | 2007-12-17 | 2012-04-17 | Symrise Gmbh & Co. Kg | Process for the preparation of a flavoring concentrate |
| KR101664355B1 (ko) * | 2014-07-24 | 2016-10-11 | 농업회사법인조인주식회사 | 오일의 오메가-3 지방산 함량을 증가시키는 칸디다 안타르티카 5k-11 균주 및 이를 이용하여 제조된 발효 오일 |
| US20170191086A1 (en) * | 2015-12-30 | 2017-07-06 | Natura Cosméticos S.A. | Process for the transformation of essential oils comprising linalol |
| CN107129475B (zh) * | 2017-04-27 | 2019-05-31 | 上海应用技术大学 | 一种呋喃型氧化芳樟醇的制备方法 |
| CN109734554B (zh) * | 2019-02-25 | 2021-11-23 | 江苏暨明医药科技有限公司 | 一种反式-薄荷基-2,8-二烯-1-醇的合成工艺 |
| CN114058650A (zh) * | 2021-11-16 | 2022-02-18 | 北京化工大学 | 一种双酶偶联反应系统制备环氧植物油的方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59225176A (ja) | 1983-06-07 | 1984-12-18 | Taiyo Koryo Kk | リナロ−ルオキサイドの製造法 |
| AU639494B2 (en) | 1989-09-12 | 1993-07-29 | Novo Nordisk A/S | A process for preparing peroxycarboxylic acids using an enzyme catalyst |
-
2000
- 2000-11-07 DE DE10055092A patent/DE10055092A1/de not_active Withdrawn
-
2001
- 2001-10-25 EP EP01124390A patent/EP1205544A3/de not_active Withdrawn
- 2001-10-29 HU HU0104565A patent/HUP0104565A2/hu unknown
- 2001-10-31 JP JP2001334356A patent/JP2002191391A/ja active Pending
- 2001-11-02 CA CA002361184A patent/CA2361184A1/en not_active Abandoned
- 2001-11-02 US US10/000,426 patent/US6703218B2/en not_active Expired - Fee Related
- 2001-11-05 IL IL14634401A patent/IL146344A0/xx unknown
- 2001-11-05 PL PL01350512A patent/PL350512A1/xx not_active Application Discontinuation
- 2001-11-06 KR KR1020010068715A patent/KR20020035755A/ko not_active Application Discontinuation
- 2001-11-06 RU RU2001129789/13A patent/RU2001129789A/ru not_active Application Discontinuation
- 2001-11-06 AU AU89224/01A patent/AU8922401A/en not_active Abandoned
- 2001-11-06 BR BR0105071-0A patent/BR0105071A/pt not_active Application Discontinuation
- 2001-11-06 MX MXPA01011280A patent/MXPA01011280A/es unknown
- 2001-11-07 CN CN01137810A patent/CN1396262A/zh active Pending
- 2001-11-07 EE EEP200100588A patent/EE200100588A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL350512A1 (en) | 2002-05-20 |
| US6703218B2 (en) | 2004-03-09 |
| EP1205544A3 (de) | 2002-05-22 |
| IL146344A0 (en) | 2002-07-25 |
| JP2002191391A (ja) | 2002-07-09 |
| BR0105071A (pt) | 2002-12-10 |
| US20020086376A1 (en) | 2002-07-04 |
| CN1396262A (zh) | 2003-02-12 |
| AU8922401A (en) | 2002-05-09 |
| HUP0104565A2 (en) | 2002-08-28 |
| DE10055092A1 (de) | 2002-05-08 |
| MXPA01011280A (es) | 2002-05-14 |
| EE200100588A (et) | 2002-06-17 |
| CA2361184A1 (en) | 2002-05-07 |
| EP1205544A2 (de) | 2002-05-15 |
| HU0104565D0 (en) | 2002-01-28 |
| KR20020035755A (ko) | 2002-05-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FA93 | Acknowledgement of application withdrawn (no request for examination) |
Effective date: 20050111 |