ES2195777B1 - PROCEDURE FOR OBTAINING SMELLY PRODUCTS TYPE AMBER GRAY FROM ESCLAREOL. - Google Patents
PROCEDURE FOR OBTAINING SMELLY PRODUCTS TYPE AMBER GRAY FROM ESCLAREOL.Info
- Publication number
- ES2195777B1 ES2195777B1 ES200200685A ES200200685A ES2195777B1 ES 2195777 B1 ES2195777 B1 ES 2195777B1 ES 200200685 A ES200200685 A ES 200200685A ES 200200685 A ES200200685 A ES 200200685A ES 2195777 B1 ES2195777 B1 ES 2195777B1
- Authority
- ES
- Spain
- Prior art keywords
- obtaining
- esclareol
- gray
- procedure
- ambrox
- 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 - Fee Related
Links
- 238000000034 method Methods 0.000 title abstract 2
- YPZUZOLGGMJZJO-UHFFFAOYSA-N ambrofix Natural products C1CC2C(C)(C)CCCC2(C)C2C1(C)OCC2 YPZUZOLGGMJZJO-UHFFFAOYSA-N 0.000 abstract 3
- YPZUZOLGGMJZJO-LQKXBSAESA-N ambroxan Chemical compound CC([C@@H]1CC2)(C)CCC[C@]1(C)[C@@H]1[C@]2(C)OCC1 YPZUZOLGGMJZJO-LQKXBSAESA-N 0.000 abstract 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 2
- 229910052700 potassium Inorganic materials 0.000 abstract 2
- 239000011591 potassium Substances 0.000 abstract 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 abstract 2
- UAYWVJHJZHQCIE-UHFFFAOYSA-L zinc iodide Chemical compound I[Zn]I UAYWVJHJZHQCIE-UHFFFAOYSA-L 0.000 abstract 2
- ZQXCQTAELHSNAT-UHFFFAOYSA-N 1-chloro-3-nitro-5-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC(Cl)=CC(C(F)(F)F)=C1 ZQXCQTAELHSNAT-UHFFFAOYSA-N 0.000 abstract 1
- JTNCEQNHURODLX-UHFFFAOYSA-N 2-phenylethanimidamide Chemical compound NC(=N)CC1=CC=CC=C1 JTNCEQNHURODLX-UHFFFAOYSA-N 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- IMKJGXCIJJXALX-SHUKQUCYSA-N Norambreinolide Chemical compound CC([C@@H]1CC2)(C)CCC[C@]1(C)[C@@H]1[C@]2(C)OC(=O)C1 IMKJGXCIJJXALX-SHUKQUCYSA-N 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- IMKJGXCIJJXALX-UHFFFAOYSA-N ent-Norambreinolide Natural products C1CC2C(C)(C)CCCC2(C)C2C1(C)OC(=O)C2 IMKJGXCIJJXALX-UHFFFAOYSA-N 0.000 abstract 1
- 229910000343 potassium bisulfate Inorganic materials 0.000 abstract 1
- 239000012286 potassium permanganate Substances 0.000 abstract 1
- 238000007363 ring formation reaction Methods 0.000 abstract 1
- 229910000033 sodium borohydride Inorganic materials 0.000 abstract 1
- 239000012279 sodium borohydride Substances 0.000 abstract 1
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
La presente invención consiste en sendos procedimientos para la obtención de (-)-8a,12-epoxi-13,14,15,16-tetranorlabdano, más conocido como (-)-Ambrox, a partir de esclareol. Mediante tratamiento de esclareol con permanganato potásico y bisulfato potásico se obtiene 13,14,15,16-tetranorlabdano-8a,12-g-lactona, también conocida como nor-ambreinolida, que se reduce directamente hasta (-)-ambrox mediante tratamiento con borohidruro sódico en presencia de yoduro de cinc o con borohidruro potásico en presencia de trifluoruro de boro-eterato. Alternativamente, la reducción de la g-lactona con borohidruro potásico o con vitride conduce a 13,14,15,16-tetranorlabdano- 8a,12-diol, cuya ciclación hasta (-)-ambrox se efectúa mediante tratamiento con bromotricloruro de carbono y trifenilfosfina.The present invention consists of two processes for obtaining (-) - 8a, 12-epoxy-13,14,15,16-tetranorlabdane, better known as (-) - Ambrox, from slareol. The treatment of slareol with potassium permanganate and potassium bisulfate yields 13,14,15,16-tetranorlabdano-8a, 12-g-lactone, also known as nor-ambreinolide, which is directly reduced to (-) - ambrox by treatment with sodium borohydride in the presence of zinc iodide or with potassium borohydride in the presence of boron-etherate trifluoride. Alternatively, the reduction of g-lactone with potassium borohydride or with vitride leads to 13,14,15,16-tetranorlabdano-8a, 12-diol, whose cyclization to (-) - ambrox is effected by treatment with carbon bromotricloride and triphenylphosphine
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES200200685A ES2195777B1 (en) | 2002-03-22 | 2002-03-22 | PROCEDURE FOR OBTAINING SMELLY PRODUCTS TYPE AMBER GRAY FROM ESCLAREOL. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES200200685A ES2195777B1 (en) | 2002-03-22 | 2002-03-22 | PROCEDURE FOR OBTAINING SMELLY PRODUCTS TYPE AMBER GRAY FROM ESCLAREOL. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| ES2195777A1 ES2195777A1 (en) | 2003-12-01 |
| ES2195777B1 true ES2195777B1 (en) | 2005-03-16 |
Family
ID=29763008
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES200200685A Expired - Fee Related ES2195777B1 (en) | 2002-03-22 | 2002-03-22 | PROCEDURE FOR OBTAINING SMELLY PRODUCTS TYPE AMBER GRAY FROM ESCLAREOL. |
Country Status (1)
| Country | Link |
|---|---|
| ES (1) | ES2195777B1 (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2284370B1 (en) * | 2006-01-19 | 2008-11-01 | Universidad De Granada | PROCEDURES FOR THE PREPARATION OF (-) AMBROX AND (+) - AMBRACETAL FROM (-) ESCLAREOL. |
| ES2324761B1 (en) * | 2009-03-12 | 2010-07-07 | Universidad De Granada | PROCEDURE FOR OBTAINING SMELLY PRODUCTS FROM THE BELLARDIA TRIXAGO PLANT. |
| TWI527805B (en) * | 2014-08-12 | 2016-04-01 | 國立臺灣大學 | The preparation of ambrox from labdanes of dysoxylum hongkongense, and the preparation of novel diterpenoids from dysoxylum hongkongense |
| MX2015014942A (en) * | 2015-10-23 | 2017-04-24 | Univ Michoacana De San Nicolás De Hidalgo | Method for synthesising ambroxide from 13,14,15,16-tetranor-8?,12 -labdanodiol. |
| CN105693667A (en) * | 2016-03-11 | 2016-06-22 | 山东睿鹰先锋制药有限公司 | Method for synthesizing sclareolide under catalysis of immobilized epoxidase |
| GB201800276D0 (en) | 2018-01-08 | 2018-02-21 | Univ Court Univ St Andrews | Maganese-catalysed hydrogenation of esters |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60239481A (en) * | 1984-05-14 | 1985-11-28 | T Hasegawa Co Ltd | Preparation of (+-) ambrox and utilization thereof |
| JPS6133184A (en) * | 1984-07-24 | 1986-02-17 | Takasago Corp | Preparation of l-ambrox |
| CH661724A5 (en) * | 1985-03-26 | 1987-08-14 | Firmenich & Cie | HYDROPEROXIDES USEFUL AS INTERMEDIATES FOR OBTAINING 3A, 6,6,9A-TETRAMETHYLPERHYDRONAPHTO (2,1-B) FURANNE AND PROCESS FOR OBTAINING THEM. |
| FR2676229B1 (en) * | 1991-05-07 | 1995-03-03 | Roure Sa | PROCESS FOR THE PREPARATION OF [3AR- (3AALPHA, 5ABETA, 9AALPHA, 9BBETA)] - DODECAHYDRO-3A, 6,6,9A-TETRAMETHYLNAPHTO [2,1-B] FURANE. |
-
2002
- 2002-03-22 ES ES200200685A patent/ES2195777B1/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| ES2195777A1 (en) | 2003-12-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FG2A | Definitive protection |
Ref document number: 2195777B1 Country of ref document: ES |
|
| FD2A | Announcement of lapse in spain |
Effective date: 20220629 |