PL439090A1 - 4'-Hydroxymethyl-flavan-4-ol and method for producing 4'-hydroxymethyl-flavan-4-ol - Google Patents

4'-Hydroxymethyl-flavan-4-ol and method for producing 4'-hydroxymethyl-flavan-4-ol

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Publication number
PL439090A1
PL439090A1 PL439090A PL43909021A PL439090A1 PL 439090 A1 PL439090 A1 PL 439090A1 PL 439090 A PL439090 A PL 439090A PL 43909021 A PL43909021 A PL 43909021A PL 439090 A1 PL439090 A1 PL 439090A1
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PL
Poland
Prior art keywords
flavan
hydroxymethyl
formula
hours
organic solvent
Prior art date
Application number
PL439090A
Other languages
Polish (pl)
Other versions
PL247575B1 (en
Inventor
Agnieszka Krawczyk-Łebek
Edyta Kostrzewa-Susłow
Monika Dymarska
Tomasz Janeczko
Original Assignee
Uniwersytet Przyrodniczy we Wrocławiu
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Publication date
Application filed by Uniwersytet Przyrodniczy we Wrocławiu filed Critical Uniwersytet Przyrodniczy we Wrocławiu
Priority to PL439090A priority Critical patent/PL247575B1/en
Publication of PL439090A1 publication Critical patent/PL439090A1/en
Publication of PL247575B1 publication Critical patent/PL247575B1/en

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    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
    • C12P17/02—Oxygen as only ring hetero atoms
    • C12P17/06—Oxygen as only ring hetero atoms containing a six-membered hetero ring, e.g. fluorescein
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
    • C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
    • C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
    • C07D311/32—2,3-Dihydro derivatives, e.g. flavanones
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/02—Preparation of oxygen-containing organic compounds containing a hydroxy group
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12R—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES C12C - C12Q, RELATING TO MICROORGANISMS
    • C12R2001/00—Microorganisms ; Processes using microorganisms
    • C12R2001/645—Fungi ; Processes using fungi

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Zoology (AREA)
  • Biotechnology (AREA)
  • Microbiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Przedmiotem zgłoszenia jest 4'-hydroksymetylo-flawan-4-ol o wzorze 2 oraz sposób wytwarzania 4'-hydroksymetylo-flawan-4-olu polegający na tym, że do podłoża odpowiedniego dla grzybów strzępkowych wprowadza się szczep Isaria fumosorosea KCH J2, następnie po upływie co najmniej 72 godzin do hodowli wprowadza się substrat, którym jest 4'-metyloflawanon o wzorze 1, rozpuszczony w rozpuszczalniku organicznym mieszającym się z wodą, transformację prowadzi się w temperaturze od 20 do 30 stopni Celsjusza, przy ciągłym wstrząsaniu, co najmniej 96 godzin, po czym produkt ekstrahuje się rozpuszczalnikiem organicznym niemieszającym się z wodą i oczyszcza chromatograficznie, przy czym 4'-hydroksymetylo-flawan-4-ol o wzorze 2 znajduje się we frakcji o pośredniej polarności, w czwartym paśmie od linii startu.The subject of the application is 4'-hydroxymethyl-flavan-4-ol of the formula 2 and a method for the production of 4'-hydroxymethyl-flavan-4-ol in which the strain Isaria fumosorosea KCH J2 is introduced into a medium suitable for filamentous fungi, followed by after at least 72 hours, the substrate, which is 4'-methylflavanone of the formula 1, dissolved in an organic solvent miscible with water, is introduced into the culture, the transformation is carried out at a temperature of 20 to 30 degrees Celsius, with continuous shaking, for at least 96 hours , the product is then extracted with a water-immiscible organic solvent and purified by chromatography, the 4'-hydroxymethyl-flavan-4-ol of formula 2 being in the intermediate polarity fraction in the fourth band from the starting line.

PL439090A 2021-09-30 2021-09-30 4'-Hydroxymethyl-flavan-4-ol and method for preparing 4'-hydroxymethyl-flavan-4-ol PL247575B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
PL439090A PL247575B1 (en) 2021-09-30 2021-09-30 4'-Hydroxymethyl-flavan-4-ol and method for preparing 4'-hydroxymethyl-flavan-4-ol

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PL439090A PL247575B1 (en) 2021-09-30 2021-09-30 4'-Hydroxymethyl-flavan-4-ol and method for preparing 4'-hydroxymethyl-flavan-4-ol

Publications (2)

Publication Number Publication Date
PL439090A1 true PL439090A1 (en) 2023-04-03
PL247575B1 PL247575B1 (en) 2025-07-28

Family

ID=85784013

Family Applications (1)

Application Number Title Priority Date Filing Date
PL439090A PL247575B1 (en) 2021-09-30 2021-09-30 4'-Hydroxymethyl-flavan-4-ol and method for preparing 4'-hydroxymethyl-flavan-4-ol

Country Status (1)

Country Link
PL (1) PL247575B1 (en)

Also Published As

Publication number Publication date
PL247575B1 (en) 2025-07-28

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