WO2006015811A3 - Technologisch hergestelltes dihydrocoumarin - Google Patents

Technologisch hergestelltes dihydrocoumarin Download PDF

Info

Publication number
WO2006015811A3
WO2006015811A3 PCT/EP2005/008512 EP2005008512W WO2006015811A3 WO 2006015811 A3 WO2006015811 A3 WO 2006015811A3 EP 2005008512 W EP2005008512 W EP 2005008512W WO 2006015811 A3 WO2006015811 A3 WO 2006015811A3
Authority
WO
WIPO (PCT)
Prior art keywords
coumarin
dihydrocoumarin
biotransformation
enzymes
natural
Prior art date
Application number
PCT/EP2005/008512
Other languages
English (en)
French (fr)
Other versions
WO2006015811A2 (de
Inventor
Hans Henning Wenk
Wilfried Schwab
Katrin Haeser
Original Assignee
Maxens Gmbh
Hans Henning Wenk
Wilfried Schwab
Katrin Haeser
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 Maxens Gmbh, Hans Henning Wenk, Wilfried Schwab, Katrin Haeser filed Critical Maxens Gmbh
Priority to EP05774348A priority Critical patent/EP1778852A2/de
Priority to US11/659,595 priority patent/US20080171123A1/en
Priority to JP2007524291A priority patent/JP2008508870A/ja
Publication of WO2006015811A2 publication Critical patent/WO2006015811A2/de
Publication of WO2006015811A3 publication Critical patent/WO2006015811A3/de

Links

Classifications

    • 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
    • C12P7/40—Preparation of oxygen-containing organic compounds containing a carboxyl group including Peroxycarboxylic acids
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/10—Natural spices, flavouring agents or condiments; Extracts thereof
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/206—Dairy flavours
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/28—Coffee or cocoa flavours
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/29—Fruit flavours
    • 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
    • C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
    • C07D311/20—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 hydrogenated in the hetero ring
    • 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
    • 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
    • C12P7/40—Preparation of oxygen-containing organic compounds containing a carboxyl group including Peroxycarboxylic acids
    • C12P7/42—Hydroxy-carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Y—ENZYMES
    • C12Y103/00—Oxidoreductases acting on the CH-CH group of donors (1.3)
    • C12Y103/01—Oxidoreductases acting on the CH-CH group of donors (1.3) with NAD+ or NADP+ as acceptor (1.3.1)
    • C12Y103/01011—2-Coumarate reductase (1.3.1.11)
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Polymers & Plastics (AREA)
  • Food Science & Technology (AREA)
  • Nutrition Science (AREA)
  • Genetics & Genomics (AREA)
  • Biochemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Microbiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Biotechnology (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Seasonings (AREA)

Abstract

Beansprucht wird ein technologisch durch Biotransformation aus Coumarin hergestelltes Dihydrocoumarin und damit zusammenhängende Herstellungsvarianten, die mit Hilfe isolierter Enzyme und/oder Mikroorganismen durchgeführt werden. Als Ausgangsmaterialien können sowohl reines Coumarin, als auch aus einem Pflanzenextrakt isoliertes Coumarin oder aber Coumarin-haltige Pflanzenextrakte eingesetzt werden. Ausgewählte Stämme von Saccharomyces, Arthrobacter, Pseudomonas, Bacillus, Basidiomycetes und Fusarium können direkt für die Biotransformation eingesetzt werden oder aber die dafür benötigten Enzyme liefern. Bevorzugte Enzyme sind Coumarat- und Coumarin-Reduktasen. Beansprucht wird weiterhin eine Verfahrensvariante, die von Coumarin ausgeht, und entweder über o-Coumarsäure, oder aber über intermediär gebildetes Dihydrocoumarin, zur nachfolgenden Melilotsäure führt, welche anschliessend zum Dihydrocoumarin dehydratisiert wird. Das so erhaltene Dihydrocoumarin erfüllt sämtliche Kriterien eines natürlichen Rohstoffes, weshalb das Produkt auch als natürlicher Aromastoff oder zur Herstellung bzw. als Bestandteil von natürlichen, naturidentischen und synthetischen Aromen eingesetzt werden kann, wie sie typischerweise in Backwaren, Süsswaren, Getränken, Cremes, Getreideprodukten und Milcherzeugnissen Verwendung finden.
PCT/EP2005/008512 2004-08-06 2005-08-05 Technologisch hergestelltes dihydrocoumarin WO2006015811A2 (de)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP05774348A EP1778852A2 (de) 2004-08-06 2005-08-05 Technologisch hergestelltes dihydrocoumarin
US11/659,595 US20080171123A1 (en) 2004-08-06 2005-08-05 Technically Produced Dihydrocoumarin
JP2007524291A JP2008508870A (ja) 2004-08-06 2005-08-05 工業的に製造されたジヒドロクマリン

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102004038154.2 2004-08-06
DE102004038154A DE102004038154A1 (de) 2004-08-06 2004-08-06 Technologisch hergestelltes Dihydrocoumarin

Publications (2)

Publication Number Publication Date
WO2006015811A2 WO2006015811A2 (de) 2006-02-16
WO2006015811A3 true WO2006015811A3 (de) 2006-04-06

Family

ID=35610111

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2005/008512 WO2006015811A2 (de) 2004-08-06 2005-08-05 Technologisch hergestelltes dihydrocoumarin

Country Status (5)

Country Link
US (1) US20080171123A1 (de)
EP (1) EP1778852A2 (de)
JP (1) JP2008508870A (de)
DE (1) DE102004038154A1 (de)
WO (1) WO2006015811A2 (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5700913B2 (ja) * 2008-09-30 2015-04-15 小林製薬株式会社 芳香性組成物
CN113584099B (zh) * 2021-07-28 2023-11-14 南京先进生物材料与过程装备研究院有限公司 一种采用微流场反应技术制备二氢香豆素或其衍生物的方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3442910A (en) * 1967-06-22 1969-05-06 Eastman Kodak Co Preparation of hydrocoumarin,coumarin and alkyl substituted derivatives
US5874398A (en) * 1997-04-10 1999-02-23 Haarmann & Reimer Gmbh Ethylvanillin isobutyrate
US6462203B2 (en) * 2000-09-01 2002-10-08 Haarmann & Reimer Gmbh Process for the preparation of dihydrocoumarin by hydrogenating coumarin

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU5347999A (en) * 1998-08-12 2000-03-06 Maxygen, Inc. Dna shuffling of monooxygenase genes for production of industrial chemicals
EP1208193A1 (de) * 1999-08-12 2002-05-29 Maxygen, Inc. Dna-shuffling von dioxygenase gene zur herstellung von industrielle chemikalien

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3442910A (en) * 1967-06-22 1969-05-06 Eastman Kodak Co Preparation of hydrocoumarin,coumarin and alkyl substituted derivatives
US5874398A (en) * 1997-04-10 1999-02-23 Haarmann & Reimer Gmbh Ethylvanillin isobutyrate
US6462203B2 (en) * 2000-09-01 2002-10-08 Haarmann & Reimer Gmbh Process for the preparation of dihydrocoumarin by hydrogenating coumarin

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
KOSUGE T ET AL: "The metabolism of aromatic compounds in higher plants. V. Purification and properties of dihydrocoumarin hydrolase of Melilotus alba.", THE JOURNAL OF BIOLOGICAL CHEMISTRY. MAY 1962, vol. 237, May 1962 (1962-05-01), pages 1653 - 1656, XP002365187, ISSN: 0021-9258 *
LEVY C C ET AL: "THE METABOLISM OF COUMARIN BY A MICROORGANISM. II. THE REDUCTION OF O-COUMARIC ACID TO MELILOTIC ACID.", BIOCHEMISTRY. DEC 1964, vol. 3, December 1964 (1964-12-01), pages 1944 - 1947, XP002365188, ISSN: 0006-2960 *
NAKAYAMA Y ET AL: "THE METABOLISM OF COUMARIN BY A PSEUDOMONAS-SP", AGRICULTURAL AND BIOLOGICAL CHEMISTRY, vol. 37, no. 6, 1973, pages 1423 - 1437, XP008059131, ISSN: 0002-1369 *
SHIEH H S ET AL: "Use of coumarin by soil fungi.", CANADIAN JOURNAL OF MICROBIOLOGY. JUN 1969, vol. 15, no. 6, June 1969 (1969-06-01), pages 647 - 648, XP008059134, ISSN: 0008-4166 *

Also Published As

Publication number Publication date
US20080171123A1 (en) 2008-07-17
DE102004038154A1 (de) 2006-03-16
WO2006015811A2 (de) 2006-02-16
JP2008508870A (ja) 2008-03-27
EP1778852A2 (de) 2007-05-02

Similar Documents

Publication Publication Date Title
WO2002065840A3 (en) Consumable product containing probiotics
CA2312938A1 (en) Pectin, method for its production, acidic protein foods incorporating it and method for their production
WO2004074352A3 (en) Carbonation of epoxidized vegetable oils and nonisocyanate-polyurethanes derived therefrom
ATE524074T1 (de) Getränke-vorprodukt und verahren zu seiner herstellung
WO2006044290A3 (en) Biosynthesis of philoroglucinol and preparation of 1,3-dihydroxybenzene therefrom
WO2007024770A3 (en) Methods of forming phytosterol-fortified cocoa powder and the product formed therefrom
MX2007002593A (es) Extracto natural que contiene xantohumol, asi como el procedimiento para su produccion y productos producidos a partir del mismo.
Gambato et al. Evaluation of productivity and antioxidant profile of solid-state cultivated macrofungi Pleurotus albidus and Pycnoporus sanguineus
WO2003054189A3 (de) Verfahren zur transformation von pflanzlichen plastiden
EP1407679A4 (de) Verfahren zur herstellung von pflanzenextrakthaltigem pflanzenpulver
WO1999042602A3 (en) Fermentative preparation process for cytostatics and crystal forms thereof
WO2004033421A3 (en) Improved production of bacterial strains
WO2007065023A3 (en) Processes for obtaining lignan extracts and compositions containing the lignan extracts
EP2127529A4 (de) Kuchen
EP1683805A4 (de) Neuer inhibitor für die bildung von advanced-glycation-endprodukten und aldosereduktaseinhibitor
TNSN02062A1 (en) Process for the preparation of racemic citalopram and/or s- or r -citalopram by separation of a mixture of r- and s-citalopram
WO2006015811A3 (de) Technologisch hergestelltes dihydrocoumarin
EP1491099A4 (de) Verfahren zur herstellung von schaltdiagramm und dieses enthaltende nahrungsmittel und getränke
WO2006012594A3 (en) Modification of lignin biosynthesis
WO2008114656A1 (ja) リパーゼ粉末製剤、その製造方法及び使用
WO2007011887A3 (en) Production of morphinan alkaloids and derivatives in plants
AU2001259929A1 (en) Method for producing sugar or products containing sugar from vegetal raw materials containing sugar
WO2007047085A3 (en) Acidified milk products containing pectin
WO2002012481A3 (en) Enhancement of industrial production by increasing substrate transport
WO2007121402A3 (en) Fruit product and method of manufacture of the fruit product

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A2

Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BW BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE EG ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KM KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NA NG NI NO NZ OM PG PH PL PT RO RU SC SD SE SG SK SL SM SY TJ TM TN TR TT TZ UA UG US UZ VC VN YU ZA ZM ZW

AL Designated countries for regional patents

Kind code of ref document: A2

Designated state(s): BW GH GM KE LS MW MZ NA SD SL SZ TZ UG ZM ZW AM AZ BY KG KZ MD RU TJ TM AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IS IT LT LU LV MC NL PL PT RO SE SI SK TR BF BJ CF CG CI CM GA GN GQ GW ML MR NE SN TD TG

DPE1 Request for preliminary examination filed after expiration of 19th month from priority date (pct application filed from 20040101)
121 Ep: the epo has been informed by wipo that ep was designated in this application
WWE Wipo information: entry into national phase

Ref document number: 2007524291

Country of ref document: JP

NENP Non-entry into the national phase

Ref country code: DE

WWE Wipo information: entry into national phase

Ref document number: 2005774348

Country of ref document: EP

WWP Wipo information: published in national office

Ref document number: 2005774348

Country of ref document: EP

WWE Wipo information: entry into national phase

Ref document number: 11659595

Country of ref document: US