WO1999024448A3 - Neuartige sophoroselipide, verfahren zu deren herstellung und verwendung - Google Patents

Neuartige sophoroselipide, verfahren zu deren herstellung und verwendung Download PDF

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Publication number
WO1999024448A3
WO1999024448A3 PCT/EP1998/006590 EP9806590W WO9924448A3 WO 1999024448 A3 WO1999024448 A3 WO 1999024448A3 EP 9806590 W EP9806590 W EP 9806590W WO 9924448 A3 WO9924448 A3 WO 9924448A3
Authority
WO
WIPO (PCT)
Prior art keywords
sophoroselipids
formula
ch2ch2ch3
alkanols
aforementioned
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/EP1998/006590
Other languages
English (en)
French (fr)
Other versions
WO1999024448A2 (de
Inventor
Siegmund Lang
Andreas Brakemeier
Dieter Wullbrandt
Andreas Seiffert-Stoeriko
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Aventis Research and Technologies GmbH and Co KG
Original Assignee
Aventis Research and Technologies GmbH and Co KG
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 Aventis Research and Technologies GmbH and Co KG filed Critical Aventis Research and Technologies GmbH and Co KG
Priority to EP98955474A priority Critical patent/EP1028969A2/de
Priority to US09/530,769 priority patent/US6433152B1/en
Priority to JP2000520456A priority patent/JP2001522597A/ja
Publication of WO1999024448A2 publication Critical patent/WO1999024448A2/de
Publication of WO1999024448A3 publication Critical patent/WO1999024448A3/de
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/667—Neutral esters, e.g. sorbitan esters
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
    • A01N43/16—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with oxygen as the ring hetero atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/60—Sugars; Derivatives thereof
    • A61K8/602—Glycosides, e.g. rutin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/02—Acyclic radicals, not substituted by cyclic structures
    • C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
    • 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
    • C12P19/00—Preparation of compounds containing saccharide radicals
    • C12P19/44—Preparation of O-glycosides, e.g. glucosides
    • C12P19/46—Preparation of O-glycosides, e.g. glucosides having an oxygen atom of the saccharide radical bound to a cyclohexyl radical, e.g. kasugamycin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/85—Products or compounds obtained by fermentation, e.g. yoghurt, beer, wine

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Veterinary Medicine (AREA)
  • Genetics & Genomics (AREA)
  • Biotechnology (AREA)
  • Biochemistry (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Dermatology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Dentistry (AREA)
  • Environmental Sciences (AREA)
  • Microbiology (AREA)
  • General Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Agronomy & Crop Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Molecular Biology (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Medicinal Preparation (AREA)
  • Cosmetics (AREA)
  • Saccharide Compounds (AREA)

Abstract

Die vorliegende Erfindung betrifft Sophoroselipide der Formel (I), worin R4 H, -CH¿2?CH3, -CH2CH2CH3, n eine ganze Zahl von 2 bis 27, R?1 und R2¿ unabhängig voneinander H oder Formel (II) und R3 H oder -OH bedeuten. Des weiteren wird ein Verfahren zur Herstellung von Sophoroselipiden gemäß Formel (I) offenbart, wobei die Reste R?1, R2 und R3¿ und n die oben genannte Bedeutung haben und R4 -CH3, -CH2CH3 oder -CH2CH2CH3 bedeutet, bei dem eine Hefe mit der Fähigkeit, Sophoroselipide in Form eines Lactons in den Kulturüberstand zu sezernieren, in einem Kulturmedium fermentiert wird, welches Glycerin, Succinat, ein Mono-, ein Di- und/oder ein Trisaccharid und einen Lipid-Precursor enthält, und anschließend das Sophoroselipid aus der Kulturlösung isoliert wird, dadurch gekennzeichnet, daß der Lipid-Precursor ein oder mehrere 3-Alkanole, 4-Alkanole oder Alkanone mit einer Kettenlänge von 6 bis 30 Kohlenstoffatomen oder Mischungen dieser Alkanole/Alkanone aufweist. Zusätzlich wird eine Variante des obigen Verfahrens zur Herstellung von Sophoroselipiden gemäß Formel (I) beschrieben, wobei die Reste R?1, R2 und R3¿ und n die oben genannte Bedeutung haben und R4 H, -CH¿3?, -CH2CH3 oder -CH2CH2CH3 bedeutet, bei dem das Kulturmedium während der Fermentation unter einer verminderten Sauerstoffkonzentration gehalten wird. Die neuartigen Sophoroselipide können beispielsweise als Tensid, Kosmetika, Desinfektionsmittel oder Pharmazeutikum verwendet werden.
PCT/EP1998/006590 1997-11-07 1998-10-17 Neuartige sophoroselipide, verfahren zu deren herstellung und verwendung Ceased WO1999024448A2 (de)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP98955474A EP1028969A2 (de) 1997-11-07 1998-10-17 Neuartige sophoroselipide, verfahren zu deren herstellung und verwendung
US09/530,769 US6433152B1 (en) 1997-11-07 1998-10-17 Sophoroselipids, method for their production and use
JP2000520456A JP2001522597A (ja) 1997-11-07 1998-10-17 新規ソホロース脂質、それらの製造法および使用法

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19749413.7 1997-11-07
DE19749413A DE19749413A1 (de) 1997-11-07 1997-11-07 Neuartige Sophoroselipide, Verfahren zu deren Herstellung und Verwendung

Publications (2)

Publication Number Publication Date
WO1999024448A2 WO1999024448A2 (de) 1999-05-20
WO1999024448A3 true WO1999024448A3 (de) 1999-08-19

Family

ID=7848037

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1998/006590 Ceased WO1999024448A2 (de) 1997-11-07 1998-10-17 Neuartige sophoroselipide, verfahren zu deren herstellung und verwendung

Country Status (5)

Country Link
US (1) US6433152B1 (de)
EP (1) EP1028969A2 (de)
JP (1) JP2001522597A (de)
DE (1) DE19749413A1 (de)
WO (1) WO1999024448A2 (de)

Families Citing this family (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20060094089A1 (en) * 1988-09-07 2006-05-04 Martek Biosciences Corporation Process for the heterotrophic production of microbial products with high concentrations of omega-3 highly unsaturated fatty acids
US5340742A (en) * 1988-09-07 1994-08-23 Omegatech Inc. Process for growing thraustochytrium and schizochytrium using non-chloride salts to produce a microfloral biomass having omega-3-highly unsaturated fatty acids
CN105112463A (zh) * 2000-01-28 2015-12-02 Dsmip资产公司 通过在发酵罐中高密度培养真核微生物来增加含有多烯脂肪酸的脂质的产生
JP2003013093A (ja) * 2001-06-27 2003-01-15 Saraya Kk 低泡性洗浄剤組成物
JP4714377B2 (ja) * 2001-06-29 2011-06-29 サラヤ株式会社 ソホロースリピッドの精製方法
US20040242501A1 (en) * 2003-03-20 2004-12-02 Gross Richard A. Spermicidal and virucidal properties of various forms of sophorolipids
WO2007073371A1 (en) * 2004-12-22 2007-06-28 Polytechnic University Sophorolipids as protein inducers and inhibitors in fermentation medium
CA2600693A1 (en) * 2005-03-24 2006-09-28 Dsm Ip Assets B.V. Process for microbial production of a valuable compound
EP1953237A1 (de) * 2007-02-01 2008-08-06 Ecover N.V. Verfahren zur Herstellung von kurzkettigen Glycolipiden
US8148108B2 (en) * 2007-03-30 2012-04-03 The University Of Akron Process for producing cellulase
US8530206B2 (en) 2008-05-21 2013-09-10 Ecover Coordination Center N.V. Method for the production of medium-chain sophorolipids
JP5676267B2 (ja) * 2008-10-28 2015-02-25 株式会社カネカ ソホロースリピドの製造方法
US20110151100A1 (en) * 2009-12-19 2011-06-23 Satyanarayana Ganti Green Process for Production of Biosurfactants or Biopolymers through Waste Oil Utilization
GB201009882D0 (en) 2010-06-11 2010-07-21 Univ Gent Yeast strains modified in their sophorolipid production and uses thereof
US10287615B2 (en) * 2011-06-06 2019-05-14 Ecover Co-Ordination Center N.V. Sophorolactone production
WO2013003291A2 (en) 2011-06-25 2013-01-03 Tom Tao Huang Chemically modified sophorolipids and uses thereof
BR112014032940A2 (pt) 2012-07-20 2017-06-27 Sophoro Biotechnologies Llc ésteres de carboidratos como indutores de expressão de genes
JP6053124B2 (ja) * 2012-10-18 2016-12-27 花王株式会社 糖脂質の製造方法
JP6323940B2 (ja) * 2013-12-26 2018-05-16 花王株式会社 アルキルポリグリコシドの製造方法
WO2020016097A1 (en) * 2018-07-17 2020-01-23 Unilever Plc Use of a rhamnolipid in a surfactant system
WO2026077787A1 (en) * 2024-10-07 2026-04-16 Henkel Ag & Co. Kgaa Biosurfactant composition

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4215213A (en) * 1978-02-17 1980-07-29 Kao Soap Co., Ltd. Process for producing a glycolipid ester
JPH08283285A (ja) * 1995-04-12 1996-10-29 Nissin Food Prod Co Ltd 抗炎症作用を有する糖脂質
EP0745608A2 (de) * 1995-05-29 1996-12-04 Hoechst Aktiengesellschaft Neuartige Glukose- und Sophoroselipide, ein Verfahren zu deren Herstellung un deren Verwendung

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4215213A (en) * 1978-02-17 1980-07-29 Kao Soap Co., Ltd. Process for producing a glycolipid ester
JPH08283285A (ja) * 1995-04-12 1996-10-29 Nissin Food Prod Co Ltd 抗炎症作用を有する糖脂質
EP0745608A2 (de) * 1995-05-29 1996-12-04 Hoechst Aktiengesellschaft Neuartige Glukose- und Sophoroselipide, ein Verfahren zu deren Herstellung un deren Verwendung

Non-Patent Citations (6)

* Cited by examiner, † Cited by third party
Title
BRAKEMEIER A ET AL: "NOVEL SOPHOROSE LIPIDS FROM MICROBIAL CONVERSION OF 2-ALKANOLS", BIOTECHNOLOGY LETTERS, vol. 17, no. 11, 1 November 1995 (1995-11-01), pages 1183 - 1188, XP000566808 *
C.HÄLLGREN ET AL.: "Synthesis of Octyl-2-O-a-D-Mannopyranosyl-a-D-Mannopyranoside, its 6'-Phosphate and the Corresponding Monomethyl Phosphodiester : Intermediate Structures in the Biosynthesis of N-Linked Oligosaccharides in Dictyostelium Discoidium.", CARBOHYDRATE RESEARCH., vol. 260, no. 1, 4 July 1994 (1994-07-04), AMSTERDAM NL, pages 63 - 71, XP002106415 *
CHEMICAL ABSTRACTS, vol. 126, no. 9, 3 March 1997, Columbus, Ohio, US; abstract no. 118152z, K.MORIKAWA ET AL.: "Preparation of Oligosaccharide Glycosides as Antiinflammatory Agents." page 611; column 1; XP002106418 *
M.YUDA ET AL.: "Neolignan Glycosides from Roots of Codonopsis Tangshen", PHYTOCHEMISTRY, vol. 29, no. 6, 1990, pages 1989 - 1993, XP002106417 *
MATSUMURA S ET AL: "SURFACE ACTIVITIES, FOAM SUPPRESSION, BIODEGRADABILITY AND ANTIMICROBIAL PROPERTIES OF S-ALKYL GLUCOPYRANOSIDES", YUKAGAKU - JOURNAL OF THE JAPAN OIL CHEMISTS' SOCIETY, vol. 40, no. 9, 1 January 1991 (1991-01-01), pages 709 - 714, XP000653016 *
V.POZSGAY ET AL.: "Synthesis of a Pentasaccharide Fragment of Polysaccharide II of Mycobacterium tuberculosis.", CARBOHYDRATE RESEARCH., vol. 277, no. 1, 7 November 1995 (1995-11-07), AMSTERDAM NL, pages 51 - 66, XP002106416 *

Also Published As

Publication number Publication date
WO1999024448A2 (de) 1999-05-20
US6433152B1 (en) 2002-08-13
DE19749413A1 (de) 1999-05-12
EP1028969A2 (de) 2000-08-23
JP2001522597A (ja) 2001-11-20

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