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
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WO
WIPO (PCT)
Prior art keywords
sophoroselipids
formula
ch2ch2ch3
alkanols
aforementioned
Prior art date
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
Original Assignee
Aventis Res & Tech Gmbh & Co
Siegmund Lang
Andreas Brakemeier
Dieter Wullbrandt
Seiffert Stoeriko Andreas
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 Res & Tech Gmbh & Co, Siegmund Lang, Andreas Brakemeier, Dieter Wullbrandt, Seiffert Stoeriko Andreas filed Critical Aventis Res & Tech Gmbh & Co
Priority to US09/530,769 priority Critical patent/US6433152B1/en
Priority to EP98955474A priority patent/EP1028969A2/de
Priority to JP2000520456A priority patent/JP2001522597A/ja
Publication of WO1999024448A2 publication Critical patent/WO1999024448A2/de
Publication of WO1999024448A3 publication Critical patent/WO1999024448A3/de

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    • 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

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  • 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)
  • Animal Behavior & Ethology (AREA)
  • Genetics & Genomics (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Microbiology (AREA)
  • Dentistry (AREA)
  • General Engineering & Computer Science (AREA)
  • Dermatology (AREA)
  • Molecular Biology (AREA)
  • Plant Pathology (AREA)
  • Environmental Sciences (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Saccharide Compounds (AREA)
  • Medicinal Preparation (AREA)
  • Cosmetics (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 WO1999024448A2 (de)

Priority Applications (3)

Application Number Priority Date Filing Date Title
US09/530,769 US6433152B1 (en) 1997-11-07 1998-10-17 Sophoroselipids, method for their production and use
EP98955474A EP1028969A2 (de) 1997-11-07 1998-10-17 Neuartige sophoroselipide, verfahren zu deren herstellung und verwendung
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 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 (20)

* 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
KR20090064603A (ko) * 2000-01-28 2009-06-19 마텍 바이오싸이언스스 코포레이션 발효기 내에서 진핵 미생물의 고밀도 배양에 의한 고도불포화 지방산을 함유하는 지질의 증진된 생산 방법
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
US9012194B2 (en) * 2004-12-22 2015-04-21 Synthezyme Llc Sophorolipids as protein inducers and inhibitors in fermentation medium
AU2006226304B2 (en) * 2005-03-24 2012-03-15 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
WO2009141407A2 (en) * 2008-05-21 2009-11-26 Ecolife B.V. A method for the production of medium-chain sophorolipids
US8664373B2 (en) 2008-10-28 2014-03-04 Kaneka Corporation Method for producing sophorose lipid
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
WO2012168325A1 (en) * 2011-06-06 2012-12-13 Ecover Co-Ordination Center N.V. Improved sophorolactone production
US9206407B2 (en) 2011-06-25 2015-12-08 Sophoro Biotechnologies, Llc Chemically modified sophorolipids and uses thereof
CN106977558B (zh) 2012-07-20 2020-06-09 青岛蔚蓝生物集团有限公司 一种生产槐糖酯化合物的方法
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
CN112513236A (zh) * 2018-07-17 2021-03-16 联合利华知识产权控股有限公司 鼠李糖脂在表面活性剂体系中的用途

Citations (3)

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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)

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Also Published As

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

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