PL222196B1 - Method for obtaining 1-(2-hydroxyphenyl)-3-phenylpropane-1-one - Google Patents
Method for obtaining 1-(2-hydroxyphenyl)-3-phenylpropane-1-oneInfo
- Publication number
- PL222196B1 PL222196B1 PL409817A PL40981714A PL222196B1 PL 222196 B1 PL222196 B1 PL 222196B1 PL 409817 A PL409817 A PL 409817A PL 40981714 A PL40981714 A PL 40981714A PL 222196 B1 PL222196 B1 PL 222196B1
- Authority
- PL
- Poland
- Prior art keywords
- strain
- flavanone
- hydroxyphenyl
- medium
- obtaining
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 18
- JCPGMXJLFWGRMZ-UHFFFAOYSA-N 1-(2-hydroxyphenyl)-3-phenylpropan-1-one Chemical compound OC1=CC=CC=C1C(=O)CCC1=CC=CC=C1 JCPGMXJLFWGRMZ-UHFFFAOYSA-N 0.000 title claims description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- ZONYXWQDUYMKFB-UHFFFAOYSA-N flavanone Chemical compound O1C2=CC=CC=C2C(=O)CC1C1=CC=CC=C1 ZONYXWQDUYMKFB-UHFFFAOYSA-N 0.000 claims description 8
- 230000000813 microbial effect Effects 0.000 claims description 8
- 230000009466 transformation Effects 0.000 claims description 6
- 239000002609 medium Substances 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 4
- 241000223221 Fusarium oxysporum Species 0.000 claims description 3
- 238000004587 chromatography analysis Methods 0.000 claims description 3
- 238000003776 cleavage reaction Methods 0.000 claims description 3
- 230000007017 scission Effects 0.000 claims description 3
- 230000003698 anagen phase Effects 0.000 claims description 2
- 239000013630 prepared media Substances 0.000 claims description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 235000013305 food Nutrition 0.000 description 6
- BJGDMOPWBQPTDI-UHFFFAOYSA-N 3-cyclohexa-2,4-dien-1-yl-1-(2-hydroxyphenyl)prop-2-en-1-one Chemical compound OC1=CC=CC=C1C(=O)C=CC1C=CC=CC1 BJGDMOPWBQPTDI-UHFFFAOYSA-N 0.000 description 5
- 235000003599 food sweetener Nutrition 0.000 description 5
- 239000003765 sweetening agent Substances 0.000 description 4
- 241000228245 Aspergillus niger Species 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000002255 enzymatic effect Effects 0.000 description 3
- 229930003949 flavanone Natural products 0.000 description 3
- 150000002208 flavanones Chemical class 0.000 description 3
- 235000011981 flavanones Nutrition 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- ITVGXXMINPYUHD-CUVHLRMHSA-N neohesperidin dihydrochalcone Chemical group C1=C(O)C(OC)=CC=C1CCC(=O)C(C(=C1)O)=C(O)C=C1O[C@H]1[C@H](O[C@H]2[C@@H]([C@H](O)[C@@H](O)[C@H](C)O2)O)[C@@H](O)[C@H](O)[C@@H](CO)O1 ITVGXXMINPYUHD-CUVHLRMHSA-N 0.000 description 3
- 235000010434 neohesperidine DC Nutrition 0.000 description 3
- JECYUBVRTQDVAT-UHFFFAOYSA-N 2-acetylphenol Chemical compound CC(=O)C1=CC=CC=C1O JECYUBVRTQDVAT-UHFFFAOYSA-N 0.000 description 2
- 239000001329 FEMA 3811 Substances 0.000 description 2
- -1 Flavone Compounds Chemical class 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 235000009508 confectionery Nutrition 0.000 description 2
- 230000009982 effect on human Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229940089953 neohesperidin dihydrochalcone Drugs 0.000 description 2
- ARGKVCXINMKCAZ-UHFFFAOYSA-N neohesperidine Natural products C1=C(O)C(OC)=CC=C1C1OC2=CC(OC3C(C(O)C(O)C(CO)O3)OC3C(C(O)C(O)C(C)O3)O)=CC(O)=C2C(=O)C1 ARGKVCXINMKCAZ-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- AETKQQBRKSELEL-UHFFFAOYSA-N (2E)-1-(2-hydroxyphenyl)-3-phenylprop-2-en-1-one Natural products OC1=CC=CC=C1C(=O)C=CC1=CC=CC=C1 AETKQQBRKSELEL-UHFFFAOYSA-N 0.000 description 1
- 239000001100 (2S)-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one Substances 0.000 description 1
- FTVWIRXFELQLPI-ZDUSSCGKSA-N (S)-naringenin Chemical compound C1=CC(O)=CC=C1[C@H]1OC2=CC(O)=CC(O)=C2C(=O)C1 FTVWIRXFELQLPI-ZDUSSCGKSA-N 0.000 description 1
- 229940002520 2'-hydroxyacetophenone Drugs 0.000 description 1
- AETKQQBRKSELEL-ZHACJKMWSA-N 2'-hydroxychalcone Chemical compound OC1=CC=CC=C1C(=O)\C=C\C1=CC=CC=C1 AETKQQBRKSELEL-ZHACJKMWSA-N 0.000 description 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- DQFBYFPFKXHELB-UHFFFAOYSA-N Chalcone Natural products C=1C=CC=CC=1C(=O)C=CC1=CC=CC=C1 DQFBYFPFKXHELB-UHFFFAOYSA-N 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
- 241001337904 Gordonia <angiosperm> Species 0.000 description 1
- QUQPHWDTPGMPEX-UHFFFAOYSA-N Hesperidine Natural products C1=C(O)C(OC)=CC=C1C1OC2=CC(OC3C(C(O)C(O)C(COC4C(C(O)C(O)C(C)O4)O)O3)O)=CC(O)=C2C(=O)C1 QUQPHWDTPGMPEX-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 208000008589 Obesity Diseases 0.000 description 1
- 241000909534 Penicillium chermesinum Species 0.000 description 1
- 241000228150 Penicillium chrysogenum Species 0.000 description 1
- 241000984202 Peperomia obtusifolia Species 0.000 description 1
- 241000316848 Rhodococcus <scale insect> Species 0.000 description 1
- 241000187562 Rhodococcus sp. Species 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- GAMYVSCDDLXAQW-AOIWZFSPSA-N Thermopsosid Natural products O(C)c1c(O)ccc(C=2Oc3c(c(O)cc(O[C@H]4[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O4)c3)C(=O)C=2)c1 GAMYVSCDDLXAQW-AOIWZFSPSA-N 0.000 description 1
- 241000235015 Yarrowia lipolytica Species 0.000 description 1
- QUQPHWDTPGMPEX-UTWYECKDSA-N aurantiamarin Natural products COc1ccc(cc1O)[C@H]1CC(=O)c2c(O)cc(O[C@@H]3O[C@H](CO[C@@H]4O[C@@H](C)[C@H](O)[C@@H](O)[C@H]4O)[C@@H](O)[C@H](O)[C@H]3O)cc2O1 QUQPHWDTPGMPEX-UTWYECKDSA-N 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 230000036983 biotransformation Effects 0.000 description 1
- 235000019658 bitter taste Nutrition 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 235000005513 chalcones Nutrition 0.000 description 1
- 150000001789 chalcones Chemical class 0.000 description 1
- APSNPMVGBGZYAJ-GLOOOPAXSA-N clematine Natural products COc1cc(ccc1O)[C@@H]2CC(=O)c3c(O)cc(O[C@@H]4O[C@H](CO[C@H]5O[C@@H](C)[C@H](O)[C@@H](O)[C@H]5O)[C@@H](O)[C@H](O)[C@H]4O)cc3O2 APSNPMVGBGZYAJ-GLOOOPAXSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- PXLWOFBAEVGBOA-UHFFFAOYSA-N dihydrochalcone Natural products OC1C(O)C(O)C(CO)OC1C1=C(O)C=CC(C(=O)CC(O)C=2C=CC(O)=CC=2)=C1O PXLWOFBAEVGBOA-UHFFFAOYSA-N 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 125000004387 flavanoid group Chemical group 0.000 description 1
- 229930003944 flavone Natural products 0.000 description 1
- 235000011949 flavones Nutrition 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- QUQPHWDTPGMPEX-QJBIFVCTSA-N hesperidin Chemical compound C1=C(O)C(OC)=CC=C1[C@H]1OC2=CC(O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO[C@H]4[C@@H]([C@H](O)[C@@H](O)[C@H](C)O4)O)O3)O)=CC(O)=C2C(=O)C1 QUQPHWDTPGMPEX-QJBIFVCTSA-N 0.000 description 1
- VUYDGVRIQRPHFX-UHFFFAOYSA-N hesperidin Natural products COc1cc(ccc1O)C2CC(=O)c3c(O)cc(OC4OC(COC5OC(O)C(O)C(O)C5O)C(O)C(O)C4O)cc3O2 VUYDGVRIQRPHFX-UHFFFAOYSA-N 0.000 description 1
- 229940025878 hesperidin Drugs 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- RTRZOHKLISMNRD-UHFFFAOYSA-N isoflavanone Chemical compound C1OC2=CC=CC=C2C(=O)C1C1=CC=CC=C1 RTRZOHKLISMNRD-UHFFFAOYSA-N 0.000 description 1
- 230000000873 masking effect Effects 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 230000002906 microbiologic effect Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- WGEYAGZBLYNDFV-UHFFFAOYSA-N naringenin Natural products C1(=O)C2=C(O)C=C(O)C=C2OC(C1)C1=CC=C(CC1)O WGEYAGZBLYNDFV-UHFFFAOYSA-N 0.000 description 1
- 235000007625 naringenin Nutrition 0.000 description 1
- 229940117954 naringenin Drugs 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- ARGKVCXINMKCAZ-UZRWAPQLSA-N neohesperidin Chemical compound C1=C(O)C(OC)=CC=C1[C@H]1OC2=CC(O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O[C@H]3[C@@H]([C@H](O)[C@@H](O)[C@H](C)O3)O)=CC(O)=C2C(=O)C1 ARGKVCXINMKCAZ-UZRWAPQLSA-N 0.000 description 1
- 239000000879 neohesperidine DC Substances 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 102220201851 rs143406017 Human genes 0.000 description 1
- 235000019643 salty taste Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- VHBFFQKBGNRLFZ-UHFFFAOYSA-N vitamin p Natural products O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Description
POLSKAPOLAND
Urząd Patentowy Rzeczypospolitej Polskiej (12) OPIS PATENTOWY (19) PL (11) 222196 (13) B1 (21) Numer zgłoszenia: 409817 (51) Int.Cl. Patent Office of the Republic of Poland (12) PATENT DESCRIPTION (19) PL (11) 222196 (13) B1 (21) Application number: 409817 (51) Int.Cl.
C12P 7/26 (2006.01) C07C 49/82 (2006.01) C12R 1/77 (2006.01) (22) Data zgłoszenia: 16.10.2014 (54) Sposób otrzymywania 1-(2-hydroksyfenylo)-3-fenylopropan-1-onuC12P 7/26 (2006.01) C07C 49/82 (2006.01) C12R 1/77 (2006.01) (22) Date of notification: 16.10.2014 (54) Method for obtaining 1- (2-hydroxyphenyl) -3-phenylpropan-1-one
PL 222 196 B1PL 222 196 B1
Opis wynalazkuDescription of the invention
Przedmiotem wynalazku jest sposób otrzymywania 1-(2-hydroksyfenylo)-3-fenylopropan-1-onu o wzorze 2 przedstawionym na rysunku.The subject of the invention is a process for the preparation of 1- (2-hydroxyphenyl) -3-phenylpropan-1-one of the formula 2 shown in the drawing.
Wynalazek ten może znaleźć zastosowanie w przemyśle spożywczym do wytwarzania środków słodzących.The invention may find application in the food industry for the production of sweeteners.
Zwiększone spożycie znanych związków o właściwościach słodzących, które często wywierają negatywny wpływ na zdrowie człowieka, sprzyjając otyłości lub miażdżycy (Mitchell H. 2006. Sweeteners and Sugar Alternatives in Food Technology. Wyd. Blackwell Publishing ltd.), spowodowało nasilenie badań ukierunkowanych na poszukiwanie nowych środków słodzących o korzystniejszym wpływie na zdrowie człowieka.Increased consumption of known sweetening compounds, which often have a negative effect on human health, promoting obesity or atherosclerosis (Mitchell H. 2006. Sweeteners and Sugar Alternatives in Food Technology. Ed. Blackwell Publishing Ltd.), has resulted in increased research aimed at finding new sweeteners with a better effect on human health.
Dihydrochalkony, otrzymywane z naturalnych flawanoidów, takich jak naryngenina, hesperydyna, neohesperydyna charakteryzują się wysokim poziomem słodkości i z powodzeniem mogą zastępować cukry w wielu produktach spożywczych (Shin W., Kim S.J., Shin S.J. 1995, Structure-Taste Correclations in Sweet Dihydrochalcone, Sweet Dihydroisocoumarin, and Bitter Flavone Compounds.,Dihydrochalcones, obtained from natural flavanoids such as naringenin, hesperidin, neohesperidin, are characterized by a high level of sweetness and can successfully replace sugars in many food products (Shin W., Kim SJ, Shin SJ 1995, Structure-Taste Correclations in Sweet Dihydrochalcone, Sweet Dihydroisocoumar , and Bitter Flavone Compounds.,
Journal of Medicinal Chemistry: 38, 4325-4331).Journal of Medicinal Chemistry: 38,4325-4331).
Na uwagę zasługuje dihydrochalkon neohesperydyny (NHDC). Jest on 667 razy słodszy od 10%-wego roztworu sacharozy, a wartość jego progu detekcji wynosi 1100 mmol/l (Belitz H.D., Grosch W., Schieberle P. 2009. Food Chemistry. Wyd Springer-Verlag Berlin Heidelberg). Wykazuje również właściwości maskujące smak słony i gorzki, charakteryzuje się trwałością w szerokim zakresie pH (1.0-7.0) i temperatury (30-60°C). Jest niskokaloryczny i może być spożywany przez osoby chore na cukrzycę (Bar A., Borrego F., Benavente O., Castillo J., Del Rio J.A. 1990. Neohesperidin dihydrochalcone: Properties and applications. Food Science and Technology: 23, 371-376). NHDC został dopuszczony przez Unię Europejską do stosowania w żywności, jako substancja słodząca o symbolu E 959 (Rozporządzenie Komisji (UE) nr 1129/2011 z dnia 11 listopada 2011 r. zmieniające załącznik II do rozporządzenia Parlamentu Europejskiego i Rady (WE) nr 1333/2008 poprzez ustanowienie unijnego wykazu dodatków do żywności). Na jego stosowanie zezwala się również w StanachNoteworthy is neohesperidin dihydrochalcone (NHDC). It is 667 times sweeter than a 10% sucrose solution and has a detection threshold of 1100 mmol / l (Belitz H.D., Grosch W., Schieberle P. 2009. Food Chemistry. Springer-Verlag Berlin Heidelberg Ed.). It also exhibits salty and bitter taste masking properties and is stable in a wide range of pH (1.0-7.0) and temperature (30-60 ° C). It is low in calories and can be consumed by people with diabetes (Bar A., Borrego F., Benavente O., Castillo J., Del Rio JA 1990. Neohesperidin dihydrochalcone: Properties and applications. Food Science and Technology: 23, 371-376 ). NHDC has been approved by the European Union for use in food as a sweetener with the symbol E 959 (Commission Regulation (EU) No 1129/2011 of November 11, 2011 amending Annex II to the Regulation of the European Parliament and of the Council (EC) No 1333 / 2008 by establishing the EU list of food additives). Its use is also permitted in the States
Zjednoczonych, Japonii oraz Nowej Zelandii.United States, Japan and New Zealand.
Znany jest sposób otrzymywania 2'-hydroksydihydrochalkonu przy użyciu metod chemicznych. Przeprowadzono syntezę 2'-hydroksychalkonu poprzez zasadową kondensację 2'-hydroksyacetofenonu i benzaldehydu, a następnie uwodorniono z zastosowaniem katalizatora palladowo-węglowego (Tanaka T, Asai F, linuma M. (1998), Phenolic compounds from Peperomia obtusifolia. Phytochemistry, 49: 229-232).There is a known method of obtaining 2'-hydroxydihydrochalcone using chemical methods. The synthesis of 2'-hydroxychalcone was carried out by the basic condensation of 2'-hydroxyacetophenone and benzaldehyde, followed by hydrogenation with a palladium-carbon catalyst (Tanaka T, Asai F, linuma M. (1998), Phenolic compounds from Peperomia obtusifolia. Phytochemistry, 49: 229. -232).
Znane są sposoby otrzymywania ww. związku na drodze mikrobiologicznego rozszczepienia pierścienia C flawanonu. Powyższą metodą z flawanonu otrzymano 2'-hydroksydihydrochalkon z niską wydajnością 30% za pomocą kultury szczepu Penicillium chrysogenum 10002 K (Ibrahim A.-R., Abul-Hajj Y.J. (1990), Microbiological transformation of (±)-flavanone and (±)-isoflavanone. Journal of Natural Products, 53: 644-656), kultury Aspergillus niger MB w ciągu 9 dni z wydajnością 7,5% (Kostrzewa-Susłow E., Dmochowska-Gładysz K., Białońska A., Ciunik Z. (2008), Microbial transformation of flavanone by Aspergillus niger and Penicillium chermesinum cultures, Journal of Molecular Cathalysis B: Enzymatic, 52-53: 34-39), kultury szczepu Aspergillus niger SBJ z wydajnością 91%, również w ciągu 9 dni (Kostrzewa-Susłow E., Dmochowska-Gładysz J. Sposób wytwarzania 2'-hydroksydihydrochalkonu, Patent PL 208 577 B1) oraz 7-dniowej biotransformacji za pomocą kultury bakterii szczepu Rhodococcus sp. DSM 364 z wydajnością 13% (Stompor M., Potaniec B., Szumny A., Zieliński R, Żołnierczyk A.K., Anioł M. (2013), Microbial synthesis of dihydrochalcones using Rhodococcus and Gordonia species, Journal of Molecular Cathalysis B: Enzymatic, 97: 283-288).There are known methods of obtaining the above-mentioned the compound by microbial cleavage of the C-ring of the flavanone. By the above method, 2'-hydroxydihydrochalcone was obtained from flavanone with a low yield of 30% using the culture of the strain Penicillium chrysogenum 10002 K (Ibrahim A.-R., Abul-Hajj YJ (1990), Microbiological transformation of (±) -flavanone and (±) -isoflavanone. Journal of Natural Products, 53: 644-656), cultures of Aspergillus niger MB within 9 days with a yield of 7.5% (Kostrzewa-Susłow E., Dmochowska-Gładysz K., Białońska A., Ciunik Z. ( 2008), Microbial transformation of flavanone by Aspergillus niger and Penicillium chermesinum cultures, Journal of Molecular Cathalysis B: Enzymatic, 52-53: 34-39), cultures of Aspergillus niger SBJ strain with 91% yield, also within 9 days (Kostrzewa- Susłow E., Dmochowska-Gładysz J. Method for the production of 2'-hydroxydihydrochalcone, Patent PL 208 577 B1) and a 7-day biotransformation using a bacterial culture of the Rhodococcus sp. DSM 364 strain with an efficiency of 13% (Stompor M., Potaniec B., Szumny A., Zieliński R, Żołnierczyk AK, Anioł M. (2013), Microbial synthesis of dihydrochalcones using Rhodococcus and Gordonia species, Journal of Molecular Cathalysis B: Enzymatic, 97: 283-288).
Znany jest też sposób otrzymywania 2'-hydroksydihydrochalkonu za pomocą kultury szczepu Yarrowia lipolytica KCh 71 w ciągu 3 dni z wydajnością 88,2% oraz konwersją wynoszącą 98% (Janeczko T, Gładkowski W., Kostrzewa-Susłow E. (2013), Microbial transformation of chalcones to produce food sweetener derivatives, Journal of Molecular Cathalysis B: Enzymatic, 98: 55-61).There is also a known method of obtaining 2'-hydroxydihydrochalcone using the culture of the Yarrowia lipolytica KCh 71 strain within 3 days with a yield of 88.2% and a conversion of 98% (Janeczko T, Gładkowski W., Kostrzewa-Susłow E. (2013), Microbial transformation of chalcones to produce food sweetener derivatives, Journal of Molecular Cathalysis B: Enzymatic, 98: 55-61).
Postępując zgodnie z wynalazkiem, otrzymuje się 1-(2-hydroksyfenylo)-3-fenylopropan-1-on na drodze mikrobiologicznego rozszczepienia pierścienia C racemicznego (±)-flawanonu.By following the invention, 1- (2-hydroxyphenyl) -3-phenylpropan-1-one is obtained by microbial cleavage of the C-ring of racemic (±) -flavanone.
Istota wynalazku polega na tym, że do przygotowanej pożywki wprowadza się szczep Fusarium oxysporum AM13. W momencie osiągnięcia przez szczep końcowej fazy logarytmicznego wzrostu, dodaje się racemiczny (±)-flawanon, w ilości od 30 mg na 400 ml pożywki do 150 mg na 400 ml pożywki. Proces transformacji mikrobiologicznej prowadzi się wodną kulturą szczepu przy ciągłymThe essence of the invention consists in introducing the Fusarium oxysporum AM13 strain into the prepared medium. When the strain has reached its final logarithmic growth phase, racemic (±) -flavanone is added in an amount from 30 mg per 400 ml of medium to 150 mg per 400 ml of medium. The microbial transformation process is carried out continuously with the aqueous strain
PL 222 196 B1 wstrząsaniu, w wyniku czego, otrzymuje się 2'-hydroksydihydrochalkon, który ekstrahuje się rozpuszczalnikiem organicznym niemieszającym się z wodą i oczyszcza chromatograficznie.After shaking, 2'-hydroxydihydroochalcone is obtained, which is extracted with a water-immiscible organic solvent and purified by chromatography.
Korzystnie jest, gdy proces prowadzi się w temperaturze od 15 do 35°C.Preferably, the process is carried out at a temperature of 15 to 35 ° C.
Korzystnie także jest, gdy rozpuszczalnikiem organicznym jest octan etylu.It is also preferred that the organic solvent is ethyl acetate.
Zasadniczą zaletą wynalazku jest otrzymanie 2'-hydroksydihydrochalkonu, z wydajnością wynoszącą 62% oraz konwersją wg GC 85%, w temperaturze pokojowej i przy pH naturalnym dla szczepu.The main advantage of the invention is the preparation of 2'-hydroxydihydrochalcone with a yield of 62% and a GC conversion of 85%, at room temperature and pH natural for the strain.
Wynalazek jest bliżej objaśniony na przykładzie wykonania.The invention is explained in more detail using an exemplary embodiment.
P r z y k ł a d. Do kolby o pojemności 2000 cm3, w której znajduje się 400 cm3 sterylnej pożywki zawierającej 4 g aminobaku i 12 g glukozy, wprowadza się szczep Fusarium oxysporum AM13. Po godzinach jego wzrostu dodaje się 120 mg racemicznego (±)-flawanonu, o wzorze 1, rozpuszczo3 nego w 10 cm3 acetonu. Transformację prowadzi się w 25 stopniach Celsjusza przy ciągłym wstrząsaniu przez dziewięć dni. Następnie mieszaninę poreakcyjną ekstrahuje się trzykrotnie octanem etylu, osusza bezwodnym siarczanem magnezu, po czym odparowuje się rozpuszczalnik. Otrzymany ekstrakt oczyszcza się chromatograficznie, używając jako eluentu mieszaniny heksanu i acetonu w stosunku 15:1.Example d. To a flask with a capacity of 2000 cm 3, which is 400 cm 3 of sterile medium consisting of 4 g aminobaku and 12 g of glucose, is introduced into a strain of Fusarium oxysporum ÄM13. Late its growth is added to 120 mg of racemic (±) -flawanonu of formula 1, rozpuszczo nego 3 in 10 cm 3 of acetone. The transformation is carried out at 25 degrees Celsius with continuous shaking for nine days. The reaction mixture was then extracted three times with ethyl acetate, dried with anhydrous magnesium sulfate, and then the solvent was evaporated. The extract obtained is purified by chromatography using a mixture of hexane and acetone in the ratio of 15: 1 as the eluent.
Na tej drodze otrzymuje się 75 mg 2'-hydroksydihydrochalkonu (1-(2-hydroksyfenylo)-3-fenylopropan-1-onu) o wydajności 62% (konwersja wg GC 85%).In this way, 75 mg of 2'-hydroxydihydrochalcone (1- (2-hydroxyphenyl) -3-phenylpropan-1-one) are obtained with a yield of 62% (GC conversion 85%).
Uzyskany produkt charakteryzuje się następującymi danymi spektralnymi.The obtained product is characterized by the following spectral data.
1H NMR (300 MHz) (CDCI3) δ (ppm): 3,08 (t, 2H, J = 7,7 Hz, H-3); 3,34 (t, 1H, J = 7,6 Hz, H-2); 6,88 (ddd, 1H, J = 8,1; 7,2 i 1,0 Hz, H-5'); 6,99 (dd, 1H, J = 8,5; 1,0 Hz, H-3'); 7,20-7,35 (m, 5H, H-2”, H-3”, H-4”, H-5”, H-6”); 7,47 (ddd, 1H, J = 8,5; 7,2 i 1,6 Hz, H-4'); 7,75 (dd, 1H, J = 8,1; 1,6 Hz, H-6'); 12,32 (s, 1H, 2'-OH). 1 H NMR (300 MHz) (CDCl 3) δ (ppm): 3.08 (t, 2H, J = 7.7 Hz, H-3); 3.34 (t, 1H, J = 7.6Hz, H -2); 6.88 (ddd, 1H, J = 8.1, 7.2 and 1.0 Hz, H-5 '); 6.99 (dd, 1H, J = 8.5, 1.0 Hz, H-3 '); 7.20-7.35 (m, 5H, H-2 ", H-3", H-4 ", H-5", H-6 "); 7.47 (ddd, 1H, J = 8.5, 7.2 and 1.6 Hz, H-4 '); 7.75 (dd, 1H, J = 8.1, 1.6Hz, H-6 '); 12.32 (s, 1H, 2'-OH).
13C NMR (75,5 MHz, CDCI3) δ = 30,0 (C-3), 40,0 (C-2), 118,5 (C-3'), 118,9 (C-5'), 119,2 (C-1'), 126,3 (C-4”), 128,4 i 128,6 (C-2”, C-3”, C-5”, C-6”), 129,8 (C-6'), 136,3 (C-4'), 140,7 (C-1”), 162,4 (C-2'), 205,3 (C=O). 13 C NMR (75.5 MHz, CDCl3) δ = 30.0 (C-3), 40.0 (C-2), 118.5 (C-3 '), 118.9 (C-5') , 119.2 (C-1 '), 126.3 (C-4 "), 128.4 and 128.6 (C-2", C-3 ", C-5", C-6 "), 129.8 (C-6 '), 136.3 (C-4'), 140.7 (C-1 "), 162.4 (C-2 '), 205.3 (C = O).
Claims (3)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL409817A PL222196B1 (en) | 2014-10-16 | 2014-10-16 | Method for obtaining 1-(2-hydroxyphenyl)-3-phenylpropane-1-one |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL409817A PL222196B1 (en) | 2014-10-16 | 2014-10-16 | Method for obtaining 1-(2-hydroxyphenyl)-3-phenylpropane-1-one |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL409817A1 PL409817A1 (en) | 2015-06-08 |
| PL222196B1 true PL222196B1 (en) | 2016-07-29 |
Family
ID=53269213
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL409817A PL222196B1 (en) | 2014-10-16 | 2014-10-16 | Method for obtaining 1-(2-hydroxyphenyl)-3-phenylpropane-1-one |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL222196B1 (en) |
-
2014
- 2014-10-16 PL PL409817A patent/PL222196B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL409817A1 (en) | 2015-06-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Fayek et al. | A multifunctional study of naturally occurring pyrazines in biological systems; formation mechanisms, metabolism, food applications and functional properties | |
| Zha et al. | Extraction, purification and antioxidant activities of the polysaccharides from maca (Lepidium meyenii) | |
| PH12019500037A1 (en) | Method of making a flavoured sweetener and uses thereof | |
| Munir et al. | L-Asparaginase potential in acrylamide mitigation from foodstuff: a mini-review | |
| PL215429B1 (en) | Process for the preparation of dihydrochalcone | |
| JP2009067755A (en) | Method for extracting polymetoxyflavonoid | |
| PL222193B1 (en) | Method for obtaining 1-(2-hydroxyphenyl)-3-phenylpropane-1-one | |
| PL222185B1 (en) | Method for obtaining 1-(2-hydroxyphenyl)-3-(4-hydroxyphenyl)-propane-1-one | |
| EP3000334B1 (en) | Enzyme modification of sweet blackberry leaves | |
| JP6531892B2 (en) | Process for producing processed spices | |
| JP2013059353A (en) | Method for reducing oral cavity stimulating substance of sprouted grain | |
| CN104982875B (en) | Salt tolerant Acid-tolerant yeasts extract and its preparation method and application | |
| JP6346435B2 (en) | Method for producing a koji mold fermented extract containing a high content of 14-dehydroergosterol | |
| PL234136B1 (en) | 7-O-β-D-4'''-O-methyl-glucopyranosyl-5.4'-dihydroxyflavanone and method for obtaining 7-O-β-D-4'''-O-methyl-glucopyranosyl-5.4'-dihydroxyflavanone | |
| Mouhli et al. | Metabolism, Mechanisms of Antioxidants in Plants, Microbes and Animals | |
| JP6841412B2 (en) | Potassium ollotate-containing composition and method for producing the same | |
| JP2006028086A5 (en) | ||
| PL237330B1 (en) | Method for producing 3-O-β-D-glucopyranosyl-3',4',5,7-trihydroxyflavone | |
| PL236832B1 (en) | Method for obtaining 3'-O-β-D-glucopyranosyl-5.7-dihydroxy-4'-methoxyflavanone | |
| Siranjothi et al. | Gamma Irradiated Oat Glucan. | |
| JP2015007016A (en) | Method of producing novel resveratrol derivative-containing extracts | |
| Marković et al. | The effects of Detoxin-V on weight gain of broilers fed contaminated feed | |
| KR20170005397A (en) | A Functional Salt containing eatable insects and it's manufacturing method | |
| KR100811392B1 (en) | Corn licorice production method | |
| PL208578B1 (en) | Method for the manufacture of 4, 2'-dihydroxy-4'-methoxydihydrochalcone |