[go: up one dir, main page]

WO2012167813A1 - Production améliorée de sophorolactone - Google Patents

Production améliorée de sophorolactone Download PDF

Info

Publication number
WO2012167813A1
WO2012167813A1 PCT/EP2011/059306 EP2011059306W WO2012167813A1 WO 2012167813 A1 WO2012167813 A1 WO 2012167813A1 EP 2011059306 W EP2011059306 W EP 2011059306W WO 2012167813 A1 WO2012167813 A1 WO 2012167813A1
Authority
WO
WIPO (PCT)
Prior art keywords
sophorolactone
composition
water
process according
substrate
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/EP2011/059306
Other languages
English (en)
Inventor
Dirk Develter
Steve Fleurackers
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.)
Ecover Coordination Center NV
Original Assignee
Ecover Coordination Center NV
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 Ecover Coordination Center NV filed Critical Ecover Coordination Center NV
Priority to PCT/EP2011/059306 priority Critical patent/WO2012167813A1/fr
Priority to EP12725824.2A priority patent/EP2718454A1/fr
Priority to US14/123,858 priority patent/US10287615B2/en
Priority to PCT/EP2012/060744 priority patent/WO2012168325A1/fr
Priority to BE2012/0386A priority patent/BE1019942A3/nl
Publication of WO2012167813A1 publication Critical patent/WO2012167813A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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
    • C12P19/00—Preparation of compounds containing saccharide radicals
    • C12P19/12—Disaccharides
    • 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
    • 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
    • C11D1/662—Carbohydrates or derivatives
    • 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
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2096—Heterocyclic compounds
    • 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
    • C12P17/18—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms containing at least two hetero rings condensed among themselves or condensed with a common carbocyclic ring system, e.g. rifamycin
    • C12P17/181—Heterocyclic compounds containing oxygen atoms as the only ring heteroatoms in the condensed system, e.g. Salinomycin, Septamycin
    • 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
    • C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
    • 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
    • C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
    • C12P7/6436—Fatty acid esters

Definitions

  • R' is hydrogen and R" is an acetyl group, or 4. both R' and R" are hydrogen, or 5. both R' and R" are acetyl groups.
  • the molecules of formula I are lactonic sophorolipids, also called sophorolactones.
  • the molecules of formula II are open ring sophorolipids, also called sophorolipids in acid form.
  • This process has the disadvantage that a group of numerous homologs is formed. Moreover the formation ratio of these homologs varies as a function of their substrate, e.g . a hydrocarbon source, as well as the fermentation conditions. The production of a product having a g iven ratio using a fermentation process is difficult. This also hampers product development as properties and function of the sophorolipid varies with ratios of the homologs.
  • the sugar and substrate are fed to the pre-cultivated cells in a fed batch mode.
  • the fatty acid level of the reaction mixture is suppressed below 10 g/l, preferably below 8 g/l, more preferably between 1-5 g/l, expressed in weight of acid per liter of reaction mixture.
  • the invention provides a method for the preparation of a ⁇ hydroxy fatty acid of formula CH20H-CH2-(CH2)n-COOH or a ⁇ -l hydroxy fatty acid of formula CH3-CHOH-(CH2)n-COOH, wherein the acid is derived from a sophorolipid as described in any of claims 1 to 18 or 25, with n corresponding to an integer between 2 and 16, comprising the step of:
  • the invention provides sophorose obtained by a method according to an embodiment of the invention.
  • the substrate comprises a carbon chain length lower than C14, preferably between C8 and C14
  • the fermentation medium comprises cells of a Candida species modified to improve the conversion of said substrate with short carbon chain length into sophorolactone.
  • Candida species are for instance the Candida bombicola mutant strain M 18, M30 or M33; preferably Candida bombicola M30.
  • Use of these modified species has for effect that the sophorolactones will be produced with a corresponding chain length in their fatty acid moiety at an improved yield. Yield will be improved as these species have been genetically modified so that the beta-oxidation pathway is blocked.
  • a side reaction wherein a substrate comprising a carbon chain length below C14 is metabolized rather than converted into a sophorolipid is blocked.
  • Example 12 Previous attempts of obtaining crystalline sophorolipids from a crude sophorolactone composition containing considerable amounts of residual fatty acid failed. Such sophorolipid mixtures among others were obtained from fermentations that had to be terminated prematurely or when the oil feeding rate exceeded the consumption rate and accumulation of fatty acids had occurred. In order to define the maximal fatty acid content for optimal lactone isolation the following experiment was set up.
  • Table 10 summarizes the data for all hydrolysates. From the results in Table 10 it follows that the double acetylated lactone form gradually disappears upon partial hydrolysis and from 0.8 equivalents onwards some fully hydrolysed material was present.
  • the static surface tension of the partial hydrolysates obtained in the above described experiment was measured according to the pending drop method on a Kruss DSA100 tensiometer. The results are provided in Table 10. From this table it can be concluded that the 0.6 equivalent partial hydrolysate was most effective in lowering the surface tension.
  • the surfactant was formulated in the following base formula : 9.43% sodium citrate.2H 2 0; 3.08% percarbonate; 2.72% sodium carbonate; 2.05% sodium silicate; 1.05% sodium bicarbonate; 0.77% sodium polyaspartate; 0.62% TAED + 1.4 % surfactant. 20 gram of the base formula was dosed in a ZDF211 dishwasher. Program D 50°C eco was run.
  • Table 13 Storage stability data of samples with varying levels of oleic acid, measured at different temperatures.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Genetics & Genomics (AREA)
  • General Health & Medical Sciences (AREA)
  • Biotechnology (AREA)
  • Biochemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Microbiology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Molecular Biology (AREA)
  • Emergency Medicine (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)

Abstract

Cette invention concerne un procédé, comprenant les étapes suivantes : - précultiver des cellules de l'espèce Candida capables de produire de la sophorolactone, jusqu'à obtention d'une phase de croissance stationnaire, - cultiver lesdites cellules précultivées en présence d'au moins un sucre fermentable et d'un substrat, le mélange réactionnel du sucre, du substrat et des cellules précultivées étant présent en une quantité et dans des conditions telles que les cellules métabolisent le sucre et le substrat formant ainsi la sophorolactone et un acide gras, - abaisser la quantité d'acide gras qui s'est formé dans le mélange réactionnel au-dessous d'un niveau prédéfini pour cristalliser ainsi au moins une partie de la sophorolactone présente dans le mélange réactionnel, - chauffer le mélange réactionnel jusqu'à une température entre 60 et 90°C pour faire fondre ainsi les cristaux de sophorolactone, - laisser la sophorolactone à l'état fondu sédimenter et donner une composition de sophorolactone brute, et - séparer la composition de sophorolactone brute du reste du mélange réactionnel.
PCT/EP2011/059306 2011-06-06 2011-06-06 Production améliorée de sophorolactone Ceased WO2012167813A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
PCT/EP2011/059306 WO2012167813A1 (fr) 2011-06-06 2011-06-06 Production améliorée de sophorolactone
EP12725824.2A EP2718454A1 (fr) 2011-06-06 2012-06-06 Production de sophorolactone améliorée
US14/123,858 US10287615B2 (en) 2011-06-06 2012-06-06 Sophorolactone production
PCT/EP2012/060744 WO2012168325A1 (fr) 2011-06-06 2012-06-06 Production de sophorolactone améliorée
BE2012/0386A BE1019942A3 (nl) 2011-06-06 2012-06-06 Verbeterde sophorolacton samenstellingen, werkwijze voor de bereiding en gebruiken.

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/EP2011/059306 WO2012167813A1 (fr) 2011-06-06 2011-06-06 Production améliorée de sophorolactone

Publications (1)

Publication Number Publication Date
WO2012167813A1 true WO2012167813A1 (fr) 2012-12-13

Family

ID=46682602

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2011/059306 Ceased WO2012167813A1 (fr) 2011-06-06 2011-06-06 Production améliorée de sophorolactone

Country Status (1)

Country Link
WO (1) WO2012167813A1 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20150150251A1 (en) * 2012-06-06 2015-06-04 Soliance Biosolubilizer
CN114113352A (zh) * 2020-08-28 2022-03-01 深圳波顿香料有限公司 发酵液中内酯型槐糖酯含量的测定方法
US20220364136A1 (en) * 2019-12-20 2022-11-17 Locus Ip Company, Llc Improved Methods for Purification of Sophorolipids
CN115989085A (zh) * 2020-06-25 2023-04-18 佐治亚州立大学研究基金会公司 塑料聚合物生物转化过程
US20230304060A1 (en) * 2020-05-20 2023-09-28 Locus Solutions Ipco, Llc Methods of Producing Compositions Comprising Hydrophilic Sophorolipids

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0209783A1 (fr) 1985-07-24 1987-01-28 Wella Aktiengesellschaft Utilisation de sophoroselipid-lactone pour le traitement de pellicules et d'odeur corporelle
EP1411111A1 (fr) 2001-06-27 2004-04-21 Saraya Co., Ltd. Compositions detergentes peu moussantes
EP1953237A1 (fr) 2007-02-01 2008-08-06 Ecover N.V. Procédé de production de glycolipides en chaînes courtes
WO2009141407A2 (fr) * 2008-05-21 2009-11-26 Ecolife B.V. Procédé de production de sophorolipides à chaîne moyenne

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0209783A1 (fr) 1985-07-24 1987-01-28 Wella Aktiengesellschaft Utilisation de sophoroselipid-lactone pour le traitement de pellicules et d'odeur corporelle
EP1411111A1 (fr) 2001-06-27 2004-04-21 Saraya Co., Ltd. Compositions detergentes peu moussantes
EP1953237A1 (fr) 2007-02-01 2008-08-06 Ecover N.V. Procédé de production de glycolipides en chaînes courtes
WO2009141407A2 (fr) * 2008-05-21 2009-11-26 Ecolife B.V. Procédé de production de sophorolipides à chaîne moyenne

Non-Patent Citations (11)

* Cited by examiner, † Cited by third party
Title
CAVALERO D A ET AL: "The effect of medium composition on the structure and physical state of sophorolipids produced by Candida bombicola ATCC 22214", JOURNAL OF BIOTECHNOLOGY 20030612 NL LNKD- DOI:10.1016/S0168-1656(03)00067-1, vol. 103, no. 1, 12 June 2003 (2003-06-12), pages 31 - 41, XP002669185, ISSN: 0168-1656 *
FELSE ET AL: "Sophorolipid biosynthesis by Candida bombicola from industrial fatty acid residues", ENZYME AND MICROBIAL TECHNOLOGY, STONEHAM, MA, US, vol. 40, no. 2, 23 November 2006 (2006-11-23), pages 316 - 323, XP005777358, ISSN: 0141-0229, DOI: 10.1016/J.ENZMICTEC.2006.04.013 *
FLEURACKERS STEVE J J: "On the use of waste frying oil in the synthesis of sophorolipids", EUROPEAN JOURNAL OF LIPID SCIENCE AND TECHNOLOGY, vol. 108, no. 1, January 2006 (2006-01-01), pages 5 - 12, XP002669183, ISSN: 1438-7697 *
INGE N A VAN BOGAERT ET AL: "Microbial production and application of sophorolipids", APPLIED MICROBIOLOGY AND BIOTECHNOLOGY, SPRINGER, BERLIN, DE, vol. 76, no. 1, 3 May 2007 (2007-05-03), pages 23 - 34, XP019538805, ISSN: 1432-0614, DOI: 10.1007/S00253-007-0988-7 *
RAU U ET AL: "Sophorolipids: a source for novel compounds", INDUSTRIAL CROPS AND PRODUCTS, ELSEVIER, NL, vol. 13, 1 January 2001 (2001-01-01), pages 85 - 92, XP003001804, ISSN: 0926-6690, DOI: 10.1016/S0926-6690(00)00055-8 *
RICHARD D ASHBY ET AL: "The influence of increasing media methanol concentration on sophorolipid biosynthesis from glycerol-based feedstocks", BIOTECHNOLOGY LETTERS, SPRINGER NETHERLANDS, DORDRECHT, vol. 32, no. 10, 21 May 2010 (2010-05-21), pages 1429 - 1437, XP019813492, ISSN: 1573-6776 *
RICHARD D ASHBY ET AL: "The Use of Fatty Acid Esters to Enhance Free Acid Sophorolipid Synthesis", BIOTECHNOLOGY LETTERS, SPRINGER NETHERLANDS, DORDRECHT, vol. 28, no. 4, 1 February 2006 (2006-02-01), pages 253 - 260, XP019231208, ISSN: 1573-6776, DOI: 10.1007/S10529-005-5527-Y *
SOLAIMAN DANIEL K Y ET AL: "Production of sophorolipids by Candida bombicola grown on soy molasses as substrate", BIOTECHNOLOGY LETTERS, vol. 26, no. 15, August 2004 (2004-08-01), pages 1241 - 1245, XP002669184, ISSN: 0141-5492 *
STEVE FLEURACKERS, EUR. J. LIPID SCI. TECHN., vol. 108, no. 1, 2006, pages 5 - 12
VAN BOGAERT I ET AL: "Production of new-to-nature sophorolipids by cultivating the yeast Candida bombicola on unconventional hydrophobic substrates", BIOTECHNOLOGY AND BIOENGINEERING 2011 JOHN WILEY AND SONS INC. USA LNKD- DOI:10.1002/BIT.23004, vol. 108, no. 4, April 2011 (2011-04-01), pages 734 - 741, XP002669182, ISSN: 0006-3592 *
WILLIAMS, K..: "Biosurfactants for cosmetic application: Overcoming production challenges", MMG 445 BASIC BIOTECHNOLOGY EJOURNAL, vol. 5, 2009, pages 78 - 83, XP002669186, Retrieved from the Internet <URL:http://ejournal.vudat.msu.edu/index.php/mmg445/article/view/357/375> [retrieved on 20120208] *

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20150150251A1 (en) * 2012-06-06 2015-06-04 Soliance Biosolubilizer
US20220364136A1 (en) * 2019-12-20 2022-11-17 Locus Ip Company, Llc Improved Methods for Purification of Sophorolipids
JP2023507987A (ja) * 2019-12-20 2023-02-28 ローカス アイピー カンパニー リミテッド ライアビリティ カンパニー 改善されたソホロ脂質精製方法
US12344883B2 (en) * 2019-12-20 2025-07-01 Locus Solutions Ipco, Llc Methods for purification of sophorolipids
US20230304060A1 (en) * 2020-05-20 2023-09-28 Locus Solutions Ipco, Llc Methods of Producing Compositions Comprising Hydrophilic Sophorolipids
US12460238B2 (en) * 2020-05-20 2025-11-04 Locus Solutions Ipco, Llc Methods of producing compositions comprising hydrophilic sophorolipids
CN115989085A (zh) * 2020-06-25 2023-04-18 佐治亚州立大学研究基金会公司 塑料聚合物生物转化过程
CN114113352A (zh) * 2020-08-28 2022-03-01 深圳波顿香料有限公司 发酵液中内酯型槐糖酯含量的测定方法

Similar Documents

Publication Publication Date Title
US10287615B2 (en) Sophorolactone production
Fleurackers On the use of waste frying oil in the synthesis of sophorolipids
Van Bogaert et al. Microbial synthesis of sophorolipids
WO2012167813A1 (fr) Production améliorée de sophorolactone
EP1953237A1 (fr) Procédé de production de glycolipides en chaînes courtes
JP2016000017A (ja) ソフォロリピッドの製造方法
JP2002045195A (ja) ソホロースリピッドの発酵生産法
JP7418321B2 (ja) 少なくとも２種の炭素源を使用する、ラムノリピドの向上した生産
AU2021269323B2 (en) Fatty acid esters against infections in fermentations
EP2718454A1 (fr) Production de sophorolactone améliorée
WO2022210011A1 (fr) Nouveau dérivé de sophorolipide
FR2692593A1 (fr) Procédé de production de sophorolipides acétyles sous leur forme acide à partir d&#39;un substrat consistant et une huile ou un ester.
Develter et al. Sophorolipids and rhamnolipids
JP2025512090A (ja) バイオサーファクタントの発酵生産のためのプロセス
Drummond et al. Sugar fatty acid esters
JP2015104381A (ja) ソフォロリピッドの製造方法
EP0784696B1 (fr) Procede de preparation de glycosides d&#39;alkyle a chaine longue
Ashby et al. Sophorolipids: Unique microbial glycolipids with vast application potential
US6037151A (en) Process for the preparation of long-chain alkyl glycosides
Ashby et al. Glycolipids with Vast Application
JP2023053549A (ja) 新規ソホロリピッド誘導体
JP2022155726A (ja) 新規ソホロリピッド誘導体
JP2008301748A (ja) 糖脂質の製造方法
CN101878287A (zh) 洗衣产品
CN101878288A (zh) 洗衣产品

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 11725675

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 11725675

Country of ref document: EP

Kind code of ref document: A1