MD4209C1 - Process for producing sclareoloxide - Google Patents

Process for producing sclareoloxide

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Publication number
MD4209C1
MD4209C1 MDA20120036A MD20120036A MD4209C1 MD 4209 C1 MD4209 C1 MD 4209C1 MD A20120036 A MDA20120036 A MD A20120036A MD 20120036 A MD20120036 A MD 20120036A MD 4209 C1 MD4209 C1 MD 4209C1
Authority
MD
Moldova
Prior art keywords
sclareoloxide
sclareol
extraction
producing
catalyst
Prior art date
Application number
MDA20120036A
Other languages
Romanian (ro)
Russian (ru)
Other versions
MD4209B1 (en
Inventor
Вячеслав КУЛЧИТСКИЙ
Георге ДУКА
Никон УНГУР
Татьяна СЫРБУ
Михаил КОЛЦА
Ирина ГОЛОСОВ
Original Assignee
Институт Химии Академии Наук Молдовы
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 Институт Химии Академии Наук Молдовы filed Critical Институт Химии Академии Наук Молдовы
Priority to MDA20120036A priority Critical patent/MD4209C1/en
Publication of MD4209B1 publication Critical patent/MD4209B1/en
Publication of MD4209C1 publication Critical patent/MD4209C1/en

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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention deals with a process for producing sclareoloxide (1) - a compound of great utility as ingredient of different aromatization compositions, as well as intermediate in the synthesis of other valuable odorants of terpenic structure.The readily available labdanic diterpenoid sclareol (2), which is a by-product of sage (Salvia sclarea L.) essential oil production, is used as raw material.The process includes a single operation of oxidative degradation of sclareol lateral chain on ozonolysis in the presence of a co-oxidant catalyst in a homogeneous acetone-water solvent mixture at a temperature of -20°C…+15°C. Product isolation includes acetone distillation, extraction of the resulting suspension with a suitable solvent, followed by its evaporation at reduced pressure. Catalyst transformation products can be easily isolated from the aqueous phase resulting after extraction and further recycled.The produced crude sclareoloxide has a purity of at least 97% and can be used without additional purification operations.
MDA20120036A 2012-03-30 2012-03-30 Process for producing sclareoloxide MD4209C1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
MDA20120036A MD4209C1 (en) 2012-03-30 2012-03-30 Process for producing sclareoloxide

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
MDA20120036A MD4209C1 (en) 2012-03-30 2012-03-30 Process for producing sclareoloxide

Publications (2)

Publication Number Publication Date
MD4209B1 MD4209B1 (en) 2013-03-31
MD4209C1 true MD4209C1 (en) 2013-10-31

Family

ID=48045141

Family Applications (1)

Application Number Title Priority Date Filing Date
MDA20120036A MD4209C1 (en) 2012-03-30 2012-03-30 Process for producing sclareoloxide

Country Status (1)

Country Link
MD (1) MD4209C1 (en)

Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB589650A (en) * 1947-12-29 1947-06-26
US5247100A (en) * 1989-12-21 1993-09-21 Henkel Kommanditgesellschaft Auf Aktien Process for the production of sclareolide
MD217C2 (en) * 1992-07-15 1995-08-31 Институт Химии Академии Наук Молдовы Composition for smoking tobacco aromatization
EP0822191A1 (en) * 1996-08-02 1998-02-04 Quest International B.V. Preparation of intermediates for norlabdane oxide
US5821375A (en) * 1996-08-02 1998-10-13 Quest International B.V. Preparation of norlabdane oxide
US6380404B1 (en) * 1999-04-16 2002-04-30 Quest International B.V. Preparation of norlabdane oxide
MD2253C2 (en) * 2003-02-03 2004-03-31 "Тутун-Стс" С.А. Smoking aromatizing tobacco product, process for obtaining thereof, aromatic composition (variants), process for obtaining compositions for tobacco products (variants)
MD2349C2 (en) * 2003-02-03 2004-07-31 "Тутун-Стс" С.А. Aromatizing composition for the tobacco blend and process for obtaining of the aromatized tobacco blend
US7335796B2 (en) * 2005-04-05 2008-02-26 Symrise Gmbh & Co., Kg Process for the preparation of ketones by ozonolysis
US20080319232A1 (en) * 2005-09-28 2008-12-25 Symrise Gmbh & Co. Kg Synthesis of Aldehydes by Ozonolysis of Secondary Allyl

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB589650A (en) * 1947-12-29 1947-06-26
US5247100A (en) * 1989-12-21 1993-09-21 Henkel Kommanditgesellschaft Auf Aktien Process for the production of sclareolide
MD217C2 (en) * 1992-07-15 1995-08-31 Институт Химии Академии Наук Молдовы Composition for smoking tobacco aromatization
EP0822191A1 (en) * 1996-08-02 1998-02-04 Quest International B.V. Preparation of intermediates for norlabdane oxide
US5821375A (en) * 1996-08-02 1998-10-13 Quest International B.V. Preparation of norlabdane oxide
US6380404B1 (en) * 1999-04-16 2002-04-30 Quest International B.V. Preparation of norlabdane oxide
MD2253C2 (en) * 2003-02-03 2004-03-31 "Тутун-Стс" С.А. Smoking aromatizing tobacco product, process for obtaining thereof, aromatic composition (variants), process for obtaining compositions for tobacco products (variants)
MD2349C2 (en) * 2003-02-03 2004-07-31 "Тутун-Стс" С.А. Aromatizing composition for the tobacco blend and process for obtaining of the aromatized tobacco blend
US7335796B2 (en) * 2005-04-05 2008-02-26 Symrise Gmbh & Co., Kg Process for the preparation of ketones by ozonolysis
US20080319232A1 (en) * 2005-09-28 2008-12-25 Symrise Gmbh & Co. Kg Synthesis of Aldehydes by Ozonolysis of Secondary Allyl

Non-Patent Citations (8)

* Cited by examiner, † Cited by third party
Title
Alvarez-Manzaneda E.J., Chahboun R., Cano M.J., Cabrera Torres E., Alvarez E., Alvarez-Manzaneda R., Haidoura A., Ramos Lopez J.M. O3/Pb(OAc)4: a new and efficient system for the oxidative cleavage of allyl alcohols. Tetrahedron Letters, 2006, 47, 6619-6622 *
Castro Juan M., Salido Sofia, Altarejos Joachin, Nogueras Manuel and Sanches Adolfo. 8a,13-Epoxy-14,15-dinorlabd-12-ene (Sclareol Oxide) [(+)-(4aR,6aS,10aS,10bR)-3,4a,7,7,10a-Pentamethyl-4a,5,6,6a,7,8,9,10,10a,10b-decahydro-1H-benzo[f]chromene]. Molbank 2003 M304, Published 8 March 2003. Regăsit în Internet la 2013.01.01, url: http://www.mdpi.org/molbank/molbank2003/m0304.htm vezi documentul integral *
Enrique & Chahboun, Rachid & Alvarez, Esteban & Fernández, Antonio & Alvarez-Manzaneda, Ramón & Haidour, Ali & Ramos, Jose Miguel & Akhaouzan, Ali. (Published online 2011-11-09). First enantiospecific synthesis of marine sesquiterpene quinol akaol A. Chemical communications (Cambridge, England), . PMID: 22073392; doi: 10.1039/c1cc14608d. Regăsit la 2013.01.01, url: http://www.biomedsearch.com/nih/First-enantiospecific-synthesis-marine-sesquiterpene/22073392.html sau http://www.ncbi.nlm.nih.gov/pubmed/22073392Alvarez-Manzaneda, *
Frija Luis M.T., Frade Raquel F.M. and Afonso Carlos F.M. Isolation, Chemical, and Biotransformation Routes of Labdane-type Diterpenes. Chem. Reviews. dx.doi.org/10.1021-crl 00258k/ Regăsit în Internet la 2013.01.01, url: http://www.scribd.com/doc/97013211/cr100258k *
Marjon G. Bolster, Ben J.M. Jansen and Aede de Groot. The synthesis of (-) Ambrox starting from labdanolic acid. Tetrahedron 57(2001), 5657-5662 vezi pag. 5660, coloniţa dreapta, metodica 3.1.5 *
Ruzicka L., Seidel C.F., Engel L.L. Zur kenntnis der diterpene. Oxydation des sclareols mit kaliumpermanganat. Helv.Chim.Acta., 1942, 621 *
Schiaffo C.E., Dussault P.H. Ozonolysis in Solvent/Water Mixtures: Direct Conversion of Alkenes to Aldehydes and Ketones. J. Org. Chem., 2008, 73, 4688-4690 *
Влад П.Ф., Колца М.Н. Синтез и применение душистых веществ из лабдановых дитерпеноидов, Кишинев, Штиинца, 1988, с. 182 vezi pag. 102 *

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Publication number Publication date
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FG4A Patent for invention issued
KA4A Patent for invention lapsed due to non-payment of fees (with right of restoration)
MM4A Patent for invention definitely lapsed due to non-payment of fees