PL219961B1 - Optically pure (+)-trans-4 (S)-methyl-5 (R) - (3-methylbutyl)-tetrahydrofuran-2-one and a method for producing optically pure (+)-trans-4 (S)-methyl-5 - (R) - (3-methylbutyl)-tetrahydrofuran-2-one - Google Patents
Optically pure (+)-trans-4 (S)-methyl-5 (R) - (3-methylbutyl)-tetrahydrofuran-2-one and a method for producing optically pure (+)-trans-4 (S)-methyl-5 - (R) - (3-methylbutyl)-tetrahydrofuran-2-oneInfo
- Publication number
- PL219961B1 PL219961B1 PL404760A PL40476013A PL219961B1 PL 219961 B1 PL219961 B1 PL 219961B1 PL 404760 A PL404760 A PL 404760A PL 40476013 A PL40476013 A PL 40476013A PL 219961 B1 PL219961 B1 PL 219961B1
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- Poland
- Prior art keywords
- trans
- methylbutyl
- tetrahydrofuran
- methyl
- optically pure
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- PRTUUPVWXOAEDV-DTWKUNHWSA-N (3S,5R)-3-methyl-5-(3-methylbutyl)oxolan-2-one Chemical compound C[C@@H]1C(O[C@@H](C1)CCC(C)C)=O PRTUUPVWXOAEDV-DTWKUNHWSA-N 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 238000000034 method Methods 0.000 claims description 19
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical group ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- 239000000758 substrate Substances 0.000 claims description 6
- 241000223253 Rhodotorula glutinis Species 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 4
- 240000004808 Saccharomyces cerevisiae Species 0.000 claims description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- 238000004587 chromatography analysis Methods 0.000 claims description 4
- 239000012043 crude product Substances 0.000 claims description 4
- 239000003480 eluent Substances 0.000 claims description 4
- KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 claims description 4
- 239000000741 silica gel Substances 0.000 claims description 4
- 229910002027 silica gel Inorganic materials 0.000 claims description 4
- 230000009466 transformation Effects 0.000 claims description 4
- 238000000605 extraction Methods 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 claims description 2
- 230000012010 growth Effects 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 238000000746 purification Methods 0.000 claims description 2
- 230000002906 microbiologic effect Effects 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- 125000000457 gamma-lactone group Chemical group 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- -1 isoprenoid lactones Chemical class 0.000 description 2
- 230000000813 microbial effect Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- NDMRRMAGZYCGRA-UHFFFAOYSA-N 3,7-dimethyl-4-oxooctanoic acid Chemical compound CC(C)CCC(=O)C(C)CC(O)=O NDMRRMAGZYCGRA-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 235000009499 Vanilla fragrans Nutrition 0.000 description 1
- 244000263375 Vanilla tahitensis Species 0.000 description 1
- 235000012036 Vanilla tahitensis Nutrition 0.000 description 1
- 230000003698 anagen phase Effects 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000001887 anti-feedant effect Effects 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000005695 dehalogenation reaction Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 150000001261 hydroxy acids Chemical class 0.000 description 1
- 150000004715 keto acids Chemical class 0.000 description 1
- 238000007273 lactonization reaction Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000013048 microbiological method Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000006340 racemization Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 235000019565 spicy aroma Nutrition 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000003419 tautomerization reaction Methods 0.000 description 1
- 230000001131 transforming effect Effects 0.000 description 1
- DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Description
Opis wynalazkuDescription of the invention
Przedmiotem wynalazku jest optycznie czysty (+)-trans-4(S)-metylo-5(R)-(3-metylobutylo)-tetrahydrofuran-2-on o wzorze 2 przedstawionym na rysunku i sposób jego wytwarzania.The subject of the invention is optically pure (+) - trans-4 (S) -methyl-5 (R) - (3-methylbutyl) -tetrahydrofuran-2-one of the formula 2 shown in the drawing and the method of its preparation.
Związek ten charakteryzuje się interesującym zapachem przyprawowym z nutą wanilii. Wynalazek może mieć zastosowanie w przemyśle kosmetycznym oraz spożywczym do wytwarzania dodatków do żywności.This compound is characterized by an interesting spicy aroma with a hint of vanilla. The invention may be used in the cosmetics and food industries for the production of food additives.
Związek ten w formie mieszaniny racemicznej jest znany w literaturze i został uzyskany chemicznie na drodze reduktywnej dehalogenacji odpowiedniego σ-jodo-y-laktonu prowadzonej za pomocą wodorku tri-n-butylocyny i opisanej przez Wawrzeńczyka C. i wsp. (Wawrzeńczyk C., Dams I., Szumny A., Szczepanik M., Nawrot J., Prądzyńska A., Gabryś B., Dancewicz K., Magnucka E., Gawdzik B., Obara R., Wzorek A. Synthesis and evaluation of antifeedant, antifungal and antibacterial activity of isoprenoid lactones. Pol. J. Environ. Stud. 2005, 14 (lI), 69-84).This compound in the form of a racemic mixture is known in the literature and was obtained chemically by reductive dehalogenation of the appropriate σ-iodo-γ-lactone carried out with tri-n-butyltin hydride and described by Wawrzeńczyk C. et al. (Wawrzeńczyk C., Dams I., Szumny A., Szczepanik M., Nawrot J., Prądzyńska A., Gabryś B., Dancewicz K., Magnucka E., Gawdzik B., Obara R., Wzorek A. Synthesis and evaluation of antifeedant, antifungal and antibacterial activity of isoprenoid lactones. Pol. J. Environ. Stud. 2005, 14 (lI), 69-84).
Enancjomerycznie czysta postać (+)-(4S,5R)-trans γ-laktonu o wzorze 2 jest połączeniem nowym, nieopisanym do tej pory w literaturze. Element nowości stanowi również mikrobiologiczna metoda pozyskiwania omawianego γ-laktonu na drodze transformacji ketokwasu o wzorze 1 w kulturze drożdży Rhodotorula glutinis.The enantiomerically pure form of (+) - (4S, 5R) -trans of the γ-lactone of the formula 2 is a novel combination, not described so far in the literature. Another element of novelty is the microbiological method of obtaining the γ-lactone in question by transforming the keto acid of formula 1 in the Rhodotorula glutinis yeast culture.
Istotą wynalazku jest optycznie czysty (+)-trans-4(S)-metylo-5(R)-(3-metylobutylo)-tetrahydrofuran-2-on.The essence of the invention is optically pure (+) - trans-4 (S) -methyl-5 (R) - (3-methylbutyl) -tetrahydrofuran-2-one.
Istotą sposobu według wynalazku jest to, że drożdże z gatunku Rhodotorula glutinis, namnaża się w płynnym podłożu mikrobiologicznym, charakterystycznym dla tego rodzaju, przy ciągłym mieszaniu reagentów, w temperaturze od 20 do 30°C do momentu osiągnięcia przez nie fazy logarytmicznego wzrostu. Do narośniętej hodowli dodaje się kwas 3,7-dimetylo-4-oksooktanowy w stężeniu od 150 mg/L do 350 mg/L i dalej prowadzi się proces przy ciągłym wstrząsaniu, aż do całkowitego przereagowania substratu. Po zakończeniu reakcji roztwór transformacyjny zakwasza się do pH od 3,5 do 4,5 za pomocą 1-molowego roztworu kwasu chlorowodorowego, a następnie ekstrahuje się rozpuszczalnikami organicznymi niemieszającymi się z wodą, oddziela frakcję organiczną, osusza, odparowuje rozpuszczalnik i tak otrzymany surowy produkt oczyszcza się za pomocą technik chromatograficznych.The essence of the process according to the invention is that yeasts of the Rhodotorula glutinis species are grown in a liquid microbial medium characteristic of this type, with continuous mixing of the reagents, at a temperature of 20 to 30 ° C until they reach the logarithmic growth phase. 3,7-dimethyl-4-oxo-octanoic acid is added to the grown culture in a concentration from 150 mg / L to 350 mg / L and the process is continued with continuous shaking until the substrate is completely converted. After completion of the reaction, the transformation solution is acidified to a pH of 3.5 to 4.5 with 1 molar hydrochloric acid solution, then it is extracted with water-immiscible organic solvents, the organic fraction is separated, dried, the solvent is evaporated and the crude product thus obtained purified by chromatographic techniques.
Korzystnie jest, gdy proces prowadzi się w temperaturze 28°C.It is preferable that the process is carried out at a temperature of 28 ° C.
Korzystnie także jest, gdy do hodowli dodaje się substrat w stężeniu 200 mg/L.It is also preferred that the substrate is added to the culture in a concentration of 200 mg / L.
Korzystnie również jest, gdy rozpuszczalnikiem stosowanym do ekstrakcji jest chloroform.It is also preferred that the extraction solvent is chloroform.
Korzystnie także jest, gdy frakcję organiczną osusza się bezwodnym siarczanem magnezu.It is also preferred that the organic fraction is dried over anhydrous magnesium sulfate.
Dodatkowo, korzystnie jest, gdy oczyszczanie prowadzi się na żelu krzemionkowym, stosując jako eluent mieszaninę heksan-aceton 8:1.In addition, it is preferred that the purification is carried out on silica gel using an 8: 1 hexane-acetone mixture as eluent.
Postępując zgodnie z wynalazkiem, w wyniku działania układu enzymatycznego zawartego w żywych komórkach kultury Rhodotorula glutinis, następuje reakcja redukcji grupy karbonylowej jednego z enancjomerów ketokwasu z równoczesną racemizacją drugiego izomeru w procesie tautomeryzacji ketoenolowej, a następnie dochodzi do samorzutnej laktonizacji powstałego hydroksykwasu do izomeru (+)-(4S,5R)-trans nasyconego γ-laktonu.Proceeding according to the invention, as a result of the enzyme system contained in living cells of Rhodotorula glutinis culture, the carbonyl group reduction reaction of one of the keto acid enantiomers takes place with simultaneous racemization of the other isomer in the ketoenol tautomerization process, followed by spontaneous lactonization of the resulting hydroxy acid (+). - (4S, 5R) -trans saturated γ-lactone.
Zasadniczą zaletą wynalazku jest otrzymanie, w łagodnych warunkach, optycznie czystego (+)-trans-4(S)-metylo-5(R)-(3-metylobutylo)-tetrahydrofuran-2-on, jako jedynego produktu reakcji, z wydajnością 30,3%. Związek otrzymano w postaci oleistej cieczy o skręcalności właściwejThe main advantage of the invention is to obtain, under mild conditions, optically pure (+) - trans-4 (S) -methyl-5 (R) - (3-methylbutyl) -tetrahydrofuran-2-one as the only reaction product with a yield of 30 , 3%. The compound was obtained in the form of an oily liquid with specific rotation
[α] — = +46 (c = 0.49; CHCI3) z wysoką czystością optyczną - bliską 100%.[α] - = +46 (c = 0.49; CHCl 3 ) with high optical purity - close to 100%.
Wynalazek jest bliżej objaśniony w przykładach wykonania.The invention is explained in more detail in the working examples.
P r z y k ł a d 1P r z k ł a d 1
Do kolby o pojemności 300 cm3, w które znajduje się 100 cm3 sterylnej pożywki zawierającej 3 g glukozy i 1 g aminobaku, wprowadza się drożdże Rhodotorula glutinis. Po 2 dniach wzrostu drobnoustrojów w temperaturze 28°C i przy ciągłym wstrząsaniu, dodaje się 20 mg kwasu 3,7-dimetylo3 To a flask of 300 cm 3, which is 100 cm 3 of sterile medium containing 3 g of glucose and 1 g aminobaku introduced into the yeast Rhodotorula glutinis. After 2 days of microbial growth at 28 ° C and with continuous shaking, 20 mg of 3,7-dimethyl- 3 acid are added.
-4-oksooktanowego, o wzorze 1, rozpuszczonego w 1 cm3 acetonu, co oznacza, że stężenie substratu w mieszaninie reakcyjnej wynosi 200 mg/L. Transformację prowadzi się przy ciągłym wstrząsaniu przez 24 godziny. Następnie, uzyskany roztwór transformacyjny zakwasza się do pH około 4 za pomocą 1-molowego roztworu kwasu chlorowodorowego. Produkt ekstrahuje się trzykrotnie chloroformem, osusza siarczanem magnezu i odparowuje rozpuszczalnik. Otrzymuje się 12 mg surowego proPL 219 961 B1 duktu, który oczyszcza się chromatograficznie na żelu krzemionkowym, przy zastosowaniu, jako eluentu mieszaniny heksan-aceton w stosunku 8:1.-4-oxo-octane, of the formula I, dissolved in 1 cm 3 of acetone, which means that the concentration of the substrate in the reaction mixture is 200 mg / L. The transformation is carried out under continuous shaking for 24 hours. Thereafter, the resulting transformation solution is acidified to a pH of about 4 with a 1 molar hydrochloric acid solution. The product is extracted three times with chloroform, dried with magnesium sulfate and the solvent is evaporated off. 12 mg of crude product are obtained which are purified by chromatography on silica gel using an 8: 1 hexane-acetone mixture as eluent.
W ten sposób otrzymuje się 5,5 mg (+)-trans-4(S)-metylo-5(R)-(3-metylobutylo)-tetrahydrofuran-2-on (wydajność 30,3%).Thus, 5.5 mg of (+) - trans-4 (S) -methyl-5 (R) - (3-methylbutyl) -tetrahydrofuran-2-one are obtained (30.3% yield).
P r z y k ł a d 2P r z k ł a d 2
Postępuje się jak w przykładzie 1 z tym, że stężenie substratu w mieszaninie reakcyjnej wynosi 350 mg/L. Otrzymuje się 21 mg surowego produktu, który oczyszcza się chromatograficznie na żelu krzemionkowym, stosując jako eluent mieszaninę heksan-aceton w stosunku 8:1.The procedure is as in example 1, except that the substrate concentration in the reaction mixture is 350 mg / L. 21 mg of crude product are obtained, which are purified by chromatography on silica gel using an 8: 1 hexane-acetone mixture as eluent.
W ten sposób otrzymuje się 9,6 mg (+)-trans-4(S)-metylo-5(R)-(3-metylobutylo)-tetrahydrofuran2-on (wydajność 30%).Thus, 9.6 mg of (+) - trans-4 (S) -methyl-5 (R) - (3-methylbutyl) -tetrahydrofuran-2-one are obtained (30% yield).
Uzyskany produkt charakteryzuje się następującymi danymi spektralnymi:The obtained product is characterized by the following spectral data:
IR (film, cm-1): 2958 (m), 1779 (s), 1457 (m), 1169 (s), 1001 (m);IR (film, cm -1 ): 2958 (m), 1779 (s), 1457 (m), 1169 (s), 1001 (m);
1H NMR (300 MHz, CDCI3) δ: 0.88 i 0.90 (dwa d, J = 6.6 Hz, 6H, -CH(CH3)2), 1.14 (d, J = 6.4 Hz, 3H, CH3-4), 1.22-1.28 (m, 2H, CH2-2'), 1.42 (m, 1H, jeden z CH2-1'), 1.563-1.63 (m, 2H, jeden z CH2-I', H-3'), 2.13-2.25 (m, 2H, jeden z CH2-3, H-4), 2.67 (m, 1H, jeden z CH2-3), 3.98 (td, J = 7.7,4.1 Hz, 1H, H-5). 1 H NMR (300 MHz, CDCl3) δ: 0.88 and 0.90 (two d, J = 6.6 Hz, 6H, CH (CH3) 2), 1.14 (d, J = 6.4 Hz, 3H, CH3-4), 1.22 -1.28 (m, 2H, CH 2 -2 '), 1.42 (m, 1H, one of CH 2 -1'), 1.563-1.63 (m, 2H, one of CH2-I ', H-3'), 2.13-2.25 (m, 2H, one of CH2-3, H-4), 2.67 (m, 1H, one of CH2-3), 3.98 (td, J = 7.7, 4.1 Hz, 1H, H-5).
13C NMR (150 MHz, CDCI3) δ: 17.68 (CH3-4), 22.47 i 22.63 (-CH(CH3)2), 28.02 (C-3'), 32.01 (C-2'), 34.81 (C-1'), 36.18 (C-4), 37.27 (C-3), 87.87 (C-5), 176.73 (C-2) 13 C NMR (150 MHz, CDCl3) δ: 17.68 (CH3-4), 22.47 and 22.63 (-CH (CH3) 2), 28.02 (C-3 '), 32.01 (C-2'), 34.81 (C- 1 '), 36.18 (C-4), 37.27 (C-3), 87.87 (C-5), 176.73 (C-2)
Claims (7)
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| PL404760A PL219961B1 (en) | 2013-07-18 | 2013-07-18 | Optically pure (+)-trans-4 (S)-methyl-5 (R) - (3-methylbutyl)-tetrahydrofuran-2-one and a method for producing optically pure (+)-trans-4 (S)-methyl-5 - (R) - (3-methylbutyl)-tetrahydrofuran-2-one |
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