MD4209C1 - Procedeu de obţinere a sclareoloxidului - Google Patents
Procedeu de obţinere a sclareoloxidului Download PDFInfo
- 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
- sclareol
- sclareoloxide
- acetone
- extraction
- product
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 21
- LAEIZWJAQRGPDA-CIRFHOKZSA-N (4ar,6as,10as,10br)-3,4a,7,7,10a-pentamethyl-1,5,6,6a,8,9,10,10b-octahydrobenzo[f]chromene Chemical compound CC1(C)CCC[C@]2(C)[C@H]3CC=C(C)O[C@]3(C)CC[C@H]21 LAEIZWJAQRGPDA-CIRFHOKZSA-N 0.000 title claims abstract description 15
- XVULBTBTFGYVRC-HHUCQEJWSA-N sclareol Chemical compound CC1(C)CCC[C@]2(C)[C@@H](CC[C@](O)(C)C=C)[C@](C)(O)CC[C@H]21 XVULBTBTFGYVRC-HHUCQEJWSA-N 0.000 claims abstract description 28
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 18
- XVULBTBTFGYVRC-UHFFFAOYSA-N Episclareol Natural products CC1(C)CCCC2(C)C(CCC(O)(C)C=C)C(C)(O)CCC21 XVULBTBTFGYVRC-UHFFFAOYSA-N 0.000 claims abstract description 14
- LAEIZWJAQRGPDA-UHFFFAOYSA-N Manoyloxid Natural products CC1(C)CCCC2(C)C3CC=C(C)OC3(C)CCC21 LAEIZWJAQRGPDA-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000000203 mixture Substances 0.000 claims abstract description 12
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 claims abstract 2
- 238000006385 ozonation reaction Methods 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- PNZVFASWDSMJER-UHFFFAOYSA-N acetic acid;lead Chemical compound [Pb].CC(O)=O PNZVFASWDSMJER-UHFFFAOYSA-N 0.000 claims description 8
- 239000000047 product Substances 0.000 abstract description 7
- 150000001875 compounds Chemical class 0.000 abstract description 6
- 239000007800 oxidant agent Substances 0.000 abstract description 5
- 239000002904 solvent Substances 0.000 abstract description 5
- 244000182022 Salvia sclarea Species 0.000 abstract description 3
- 235000002911 Salvia sclarea Nutrition 0.000 abstract description 3
- 239000008346 aqueous phase Substances 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract description 3
- 239000003054 catalyst Substances 0.000 abstract description 3
- 238000004821 distillation Methods 0.000 abstract description 3
- 238000000605 extraction Methods 0.000 abstract description 3
- 239000003205 fragrance Substances 0.000 abstract description 3
- 239000004615 ingredient Substances 0.000 abstract description 3
- 238000002955 isolation Methods 0.000 abstract description 3
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 238000010525 oxidative degradation reaction Methods 0.000 abstract description 2
- 239000000341 volatile oil Substances 0.000 abstract description 2
- 238000005899 aromatization reaction Methods 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 abstract 1
- 150000004141 diterpene derivatives Chemical class 0.000 abstract 1
- 238000001704 evaporation Methods 0.000 abstract 1
- 230000008020 evaporation Effects 0.000 abstract 1
- 238000005949 ozonolysis reaction Methods 0.000 abstract 1
- 238000011403 purification operation Methods 0.000 abstract 1
- 239000002994 raw material Substances 0.000 abstract 1
- 235000002020 sage Nutrition 0.000 abstract 1
- 239000011877 solvent mixture Substances 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 1
- 230000009466 transformation Effects 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- 238000003776 cleavage reaction Methods 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 238000004064 recycling Methods 0.000 description 3
- 230000007017 scission Effects 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000004880 explosion Methods 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 239000012286 potassium permanganate Substances 0.000 description 2
- 150000003303 ruthenium Chemical class 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- XOBKSJJDNFUZPF-UHFFFAOYSA-N Methoxyethane Chemical compound CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000002051 biphasic effect Effects 0.000 description 1
- 238000010504 bond cleavage reaction Methods 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- 238000007172 homogeneous catalysis Methods 0.000 description 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical class ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 150000002611 lead compounds Chemical class 0.000 description 1
- JEHCHYAKAXDFKV-UHFFFAOYSA-J lead tetraacetate Chemical compound CC(=O)O[Pb](OC(C)=O)(OC(C)=O)OC(C)=O JEHCHYAKAXDFKV-UHFFFAOYSA-J 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- -1 peroxide compounds Chemical class 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011946 reduction process Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 231100000925 very toxic Toxicity 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| MDA20120036A MD4209C1 (ro) | 2012-03-30 | 2012-03-30 | Procedeu de obţinere a sclareoloxidului |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| MDA20120036A MD4209C1 (ro) | 2012-03-30 | 2012-03-30 | Procedeu de obţinere a sclareoloxidului |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| MD4209B1 MD4209B1 (en) | 2013-03-31 |
| MD4209C1 true MD4209C1 (ro) | 2013-10-31 |
Family
ID=48045141
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MDA20120036A MD4209C1 (ro) | 2012-03-30 | 2012-03-30 | Procedeu de obţinere a sclareoloxidului |
Country Status (1)
| Country | Link |
|---|---|
| MD (1) | MD4209C1 (mo) |
Citations (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB589650A (mo) * | 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 (ro) * | 1992-07-15 | 1995-08-31 | Институт Химии Академии Наук Молдовы | Compoziţie pentru aromatizarea tutunului de fumat |
| 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 (ro) * | 2003-02-03 | 2004-03-31 | "Тутун-Стс" С.А. | Produs aromatizant pentru tutun de fumat, procedeu de obţinere a lui, compoziţie aromatică (variante), procedeu de obţinere a compoziţiei pentru produsele de tutunărie (variante) |
| MD2349C2 (ro) * | 2003-02-03 | 2004-07-31 | "Тутун-Стс" С.А. | Compoziţie de aromatizare a amestecului de tutun şi procedeu de obţinere a amestecului de tutun aromatizat |
| 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 |
-
2012
- 2012-03-30 MD MDA20120036A patent/MD4209C1/ro not_active IP Right Cessation
Patent Citations (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB589650A (mo) * | 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 (ro) * | 1992-07-15 | 1995-08-31 | Институт Химии Академии Наук Молдовы | Compoziţie pentru aromatizarea tutunului de fumat |
| 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 (ro) * | 2003-02-03 | 2004-03-31 | "Тутун-Стс" С.А. | Produs aromatizant pentru tutun de fumat, procedeu de obţinere a lui, compoziţie aromatică (variante), procedeu de obţinere a compoziţiei pentru produsele de tutunărie (variante) |
| MD2349C2 (ro) * | 2003-02-03 | 2004-07-31 | "Тутун-Стс" С.А. | Compoziţie de aromatizare a amestecului de tutun şi procedeu de obţinere a amestecului de tutun aromatizat |
| 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)
| 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 * |
Also Published As
| Publication number | Publication date |
|---|---|
| MD4209B1 (en) | 2013-03-31 |
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| Date | Code | Title | Description |
|---|---|---|---|
| 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 |