ES2195777A1 - Production of amergris from amaro plant consists of two stage reaction with potassium and sodium derivatives respectively, with or without cyclising - Google Patents

Production of amergris from amaro plant consists of two stage reaction with potassium and sodium derivatives respectively, with or without cyclising

Info

Publication number
ES2195777A1
ES2195777A1 ES200200685A ES200200685A ES2195777A1 ES 2195777 A1 ES2195777 A1 ES 2195777A1 ES 200200685 A ES200200685 A ES 200200685A ES 200200685 A ES200200685 A ES 200200685A ES 2195777 A1 ES2195777 A1 ES 2195777A1
Authority
ES
Spain
Prior art keywords
amaro
cyclising
potassium
production
amergris
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.)
Granted
Application number
ES200200685A
Other languages
Spanish (es)
Other versions
ES2195777B1 (en
Inventor
Barrero Alejandro Fernandez
Manzaneda R Enrique J Alvarez
Rachid Chahboun
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Universidad de Granada
Original Assignee
Universidad de Granada
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Universidad de Granada filed Critical Universidad de Granada
Priority to ES200200685A priority Critical patent/ES2195777B1/en
Publication of ES2195777A1 publication Critical patent/ES2195777A1/en
Application granted granted Critical
Publication of ES2195777B1 publication Critical patent/ES2195777B1/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11BPRODUCING, 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
    • C11B9/00Essential oils; Perfumes
    • C11B9/0069Heterocyclic compounds
    • C11B9/0073Heterocyclic compounds containing only O or S as heteroatoms
    • C11B9/0076Heterocyclic compounds containing only O or S as heteroatoms the hetero rings containing less than six atoms

Abstract

The production of ambergris from amaro plant material comprises treatment of amaro plant with potassium permanganate and potassium bisulfate to yield 13,14,15,16-tetranorlabdano-8a,12-g-lactone (nor-ambreinolide). This is reduced directly to (-)-ambrox by sodium borohydride treatment in the presence of boro-etherate trifluoride or indirectly by cyclising with carbon bromotrichloride and triphenyl phosphine.
ES200200685A 2002-03-22 2002-03-22 PROCEDURE FOR OBTAINING SMELLY PRODUCTS TYPE AMBER GRAY FROM ESCLAREOL. Expired - Fee Related ES2195777B1 (en)

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 true ES2195777A1 (en) 2003-12-01
ES2195777B1 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)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2284370A1 (en) * 2006-01-19 2007-11-01 Universidad De Granada Method for preparation of -ambrose-(ambracetal), particularly bisnorlabdane compound from sclareol, involves utilizing ketoester
ES2324761A1 (en) * 2009-03-12 2009-08-13 Universidad De Granada Method for obtaining fragrant products from the plant bellardia trixago
US9260404B1 (en) * 2014-08-12 2016-02-16 National Taiwan University Preparation of ambrox from labdanes of Dysoxylum hongkongense, and the preparation of new diterpenoids from Dysoxylum hongkongense
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
WO2017068400A1 (en) * 2015-10-23 2017-04-27 Universidad Michoacana De San Nicolás De Hidalgo Method for synthesising ambroxide from 13,14,15,16-tetranor-8α,12-labdanodiol
WO2019138216A1 (en) 2018-01-08 2019-07-18 University Court Of The University Of St Andrews Manganese-catalysed hydrogenation of esters

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0165458A2 (en) * 1984-05-14 1985-12-27 T. Hasegawa Company, Ltd. (+)-Ambrox, process for production thereof and use thereof
JPS6133184A (en) * 1984-07-24 1986-02-17 Takasago Corp Preparation of l-ambrox
US4814469A (en) * 1985-03-26 1989-03-21 Firmenich, Sa Novel hydroperoxide and use of same as intermediate for the preparation of 3a,6,69a-tetramethylperhydronaphtho[2,1-b]furan
FR2676229A1 (en) * 1991-05-07 1992-11-13 Roure Sa Process for the preparation of [3aR-(3a alpha ,5ass,9a alpha ,9bss)]-dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b ]furan

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0165458A2 (en) * 1984-05-14 1985-12-27 T. Hasegawa Company, Ltd. (+)-Ambrox, process for production thereof and use thereof
JPS6133184A (en) * 1984-07-24 1986-02-17 Takasago Corp Preparation of l-ambrox
US4814469A (en) * 1985-03-26 1989-03-21 Firmenich, Sa Novel hydroperoxide and use of same as intermediate for the preparation of 3a,6,69a-tetramethylperhydronaphtho[2,1-b]furan
FR2676229A1 (en) * 1991-05-07 1992-11-13 Roure Sa Process for the preparation of [3aR-(3a alpha ,5ass,9a alpha ,9bss)]-dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b ]furan

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
CAPLUS [en línea] [recuperado el 15.10.2003]. Recuperado de STN International, Columbus, Ohio (EE.UU.). Nö de acceso 105:134193 & JP 61033184 A (TAKASAGO PERFUMERY CO., LTD.) 17.02.1986 (resumen) *

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2284370A1 (en) * 2006-01-19 2007-11-01 Universidad De Granada Method for preparation of -ambrose-(ambracetal), particularly bisnorlabdane compound from sclareol, involves utilizing ketoester
ES2324761A1 (en) * 2009-03-12 2009-08-13 Universidad De Granada Method for obtaining fragrant products from the plant bellardia trixago
WO2010103145A1 (en) * 2009-03-12 2010-09-16 Universidad De Granada Method for obtaining fragrant products from the plant bellardia trixago
US9260404B1 (en) * 2014-08-12 2016-02-16 National Taiwan University Preparation of ambrox from labdanes of Dysoxylum hongkongense, and the preparation of new diterpenoids from Dysoxylum hongkongense
WO2017068400A1 (en) * 2015-10-23 2017-04-27 Universidad Michoacana De San Nicolás De Hidalgo Method for synthesising ambroxide from 13,14,15,16-tetranor-8α,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
WO2019138216A1 (en) 2018-01-08 2019-07-18 University Court Of The University Of St Andrews Manganese-catalysed hydrogenation of esters

Also Published As

Publication number Publication date
ES2195777B1 (en) 2005-03-16

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