WO2013037818A9 - Boisson contenant des glycolipides en tant que conservateurs - Google Patents

Boisson contenant des glycolipides en tant que conservateurs Download PDF

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Publication number
WO2013037818A9
WO2013037818A9 PCT/EP2012/067823 EP2012067823W WO2013037818A9 WO 2013037818 A9 WO2013037818 A9 WO 2013037818A9 EP 2012067823 W EP2012067823 W EP 2012067823W WO 2013037818 A9 WO2013037818 A9 WO 2013037818A9
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WO
WIPO (PCT)
Prior art keywords
glycolipid
glycolipids
preservative
formula
formulas
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PCT/EP2012/067823
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German (de)
English (en)
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WO2013037818A2 (fr
WO2013037818A3 (fr
Inventor
Thomas Schloesser
Sven JAKUPOVIC
Werner KATZER
Grit KLUGE
Karsten Siems
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Wacker Chemie Ag
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Publication of WO2013037818A2 publication Critical patent/WO2013037818A2/fr
Publication of WO2013037818A9 publication Critical patent/WO2013037818A9/fr
Publication of WO2013037818A3 publication Critical patent/WO2013037818A3/fr

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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
    • C12P19/00—Preparation of compounds containing saccharide radicals
    • C12P19/44—Preparation of O-glycosides, e.g. glucosides
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/10—Organic substances
    • A23K20/158—Fatty acids; Fats; Products containing oils or fats
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/10—Organic substances
    • A23K20/163—Sugars; Polysaccharides
    • 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
    • A23L3/00—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
    • A23L3/34—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals
    • A23L3/3454—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals in the form of liquids or solids
    • A23L3/3463—Organic compounds; Microorganisms; Enzymes
    • 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
    • A23L3/00—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
    • A23L3/34—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals
    • A23L3/3454—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals in the form of liquids or solids
    • A23L3/3463—Organic compounds; Microorganisms; Enzymes
    • A23L3/3481—Organic compounds containing oxygen
    • 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
    • A23L3/00—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
    • A23L3/34—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals
    • A23L3/3454—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals in the form of liquids or solids
    • A23L3/3463—Organic compounds; Microorganisms; Enzymes
    • A23L3/3544—Organic compounds containing hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
    • C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
    • C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
    • C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
    • 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

Definitions

  • the invention relates to drinks containing glycolipids as natural preservatives and to processes for producing these drinks.
  • Preservatives are substances that protect a solid or liquid from spoiling due to microorganism attack.
  • microorganisms can be, for example, yeasts, molds, Gram-positive or Gram-negative bacteria.
  • yeasts, molds, Gram-positive or Gram-negative bacteria Particularly in the food industry, food infestation by yeasts, molds or bacteria must be prevented in order to ensure the safety of the products over a limited period of time.
  • Consumers' desire to consume a safe and limited-life food is offset by the desire for the greatest possible naturalness of the food. The consumer would like to forego the addition of chemically synthesized food additives.
  • natural alternatives to synthetic additives are increasingly being offered on the market.
  • a good example is the replacement of synthetic dyes in foods with dyes of natural origin.
  • Glycolipids are molecules in which one or more mono- or oligosaccharides are glycosidically bound to a lipid molecule.
  • the saccharide residue in the glycolipid is responsible for naming the various glycolipid classes. If, for example, the disaccharide sophorose is part of a glyco-lipid, it is called sophoroselipids.
  • sophoroselipids Also known in the literature are rhamnoselipids, trehaloselipids, cellobioselipids and mannosylerythritollipids.
  • Ustilago maydis ⁇ U. maydis) is a fungus of the genus U-stilaginomycete that can infest corn plants. Especially in Mexico U. maydis is considered food and is eaten there as a delicacy.
  • the genus Pseudozyma is also a member of the Usitilaginomyceten and is closely related to Ustilago.
  • R s is H or OH
  • R 7 is H or OH or -0
  • the beverage preferably contains as preservative a glycolipid of the formula (II)
  • Ri is H or COCH 3 represents
  • R 2 is the same or different and H or
  • R 3 is the same or different and is H or OH and
  • R 4 is OH or OCH 3
  • glycolipid or a salt of the glycolipid.
  • the beverage contains on its own a glycolipid of the formulas (III) to (XXV) ⁇
  • the salt is preferably an alkali or alkaline earth salt.
  • glycolipid of the formulas (XI), (XV), (IX) or (XIII) or one of their mixtures Preference is given to a glycolipid of the formulas (XI), (XV), (IX) or (XIII) or one of their mixtures, more preferably a glycolipid of the formulas (XI) or ⁇ XIII) or one of their mixtures, where again a Mixture of the glycolipids of the formulas (XI) and (XIII) is particularly preferred.
  • drinks contain at least one of said glycolipids in an amount of 10 to 4000 ppm.
  • drinks contain at least one of the glycolipids mentioned in each case in an amount of 10 to 1000 ppm.
  • drinks contain at least one of the glycolipids mentioned in each case in an amount of 10 to 100 ppm.
  • the beverages are juices, nectars, soft drinks, milk-based products, whey-containing drinks or yoghurt drinks.
  • the invention further relates to a process for the preparation of the beverages according to the invention.
  • the glycolipids or mixtures of the glycolipids according to formula (I) or formula (II) to (XXV) are either added directly to the beverage or added via Vo solutions in water or ethanol to the drink.
  • a preliminary solution of the glycolipids or mixtures of the glycolipids in beverage bases or emulsion bases for drinks is possible.
  • the glycolipids or mixtures of the glycolipids are either added directly to the beverage base or beverage emulsion base, or to the beverage base or beverage base via pre-solutions in water or ethanol.
  • the glycolipids according to formulas ⁇ I) to (XVII) and ⁇ XXV) can be prepared by cultivating the microorganism U. maydis in a nutrient medium, the glycolipids being formed by the microorganism and subsequently isolating the glycolipids from the medium getting cleaned.
  • the glycolipids according to formulas (XVIII) to (XXIV) can be prepared by culturing the microorganism Pseudozyma sp. In a nutrient medium, wherein the glycolipids are formed by the microorganism and the glycolipids are subsequently isolated from the medium and purified.
  • the preparation of the glycolipids of the formulas (I) to (XVII) and (XXV) with the aid of a 17th maydis strain is preferably carried out in a shake flask or a fermenter by methods known to the person skilled in the art.
  • the preparation of the glycolipids of the formulas (XVIII) to (XXIV) with the aid of a Pseudozyma sp, strain is preferably carried out in a shake flask or a fermenter by methods known to the person skilled in the art.
  • the carbon source is preferably sugar, sugar alcohols or organic acids. Glucose, lactose, sucrose, maltose, D-mannitol or glycerol are particularly preferably used as carbon sources.
  • the nitrogen source used is preferably ammonia, ammonium salts, amino acids, urea or protein hydrolysates.
  • salts of the elements phosphorus, chlorine, sodium, magnesium, nitrogen, potassium, calcium, iron, and in trace ⁇ i. in ⁇ concentrations ⁇ salts of the elements molybdenum, boron, cobalt, manganese, zinc, copper and nickel can be added.
  • organic acids e.g., acetate, citrate
  • amino acids e.g., L-isoleucine, D / L-methionine
  • vitamins e.g., vitamin B1, vitamin B6, vitamin B12
  • the pH of the medium during the cultivation is preferably in the pH range of 2.0 to 10.0, particularly preferably in the pH range of 2.0 to 8.5.
  • the incubation of the U. maydis strain and the Pseudozyma sp. Strain is preferably carried out under aerobic conditions over a period of 20 hours to 300 hours and in the region of the optimal growth temperature for the respective strain.
  • the incubation temperature is preferably 20-35 ° C, particularly preferred is an incubation temperature of 24-30 ° C. Particularly preferred is a cultivation time between 24 and 150 h.
  • the glycolipids can be purified by a process in which the glycolipids formed during the fermentation are omasse and culture supernatant isolated, and the compounds according to formula (I) to (XXV) are purified by chromatography, by selective extraction or by crystallization.
  • glycolipids from biomass and culture supernatant takes place in a known manner, for example by separation, centrifugation, adsorption or membrane administration.
  • solvents for example methanol, acetone, ethanol, isopropanol, methyl acetate, ethyl acetate, CO 2 , propane, butane, hexane, dichloromethane or ethyl methyl ketone, which can be used for extraction.
  • methanol is used for extraction.
  • the biomass may also be mechanically such as e.g. be pretreated by high-pressure homogenization or ultrasound.
  • the purification of the compounds can be carried out by chromatographic methods known to those skilled in the art, selective extraction, ion exchange or crystallization. Preference is given first to a coarse separation by means of medium pressure chromatography (MPLC) and subsequent fine separation by reversed phase high performance liquid chromatography (RP-HPLC).
  • MPLC medium pressure chromatography
  • RP-HPLC reversed phase high performance liquid chromatography
  • the invention also relates to the use of a glycolipid according to formula (I) to (XXV) or one of its salts as preservative in beverages, the above-mentioned preference of the different glycolipids and amounts also apply here.
  • glycolipids of the formulas (II) to (XXV) or one of their salts as preservatives in beverages is particularly preferred.
  • glycolipids of the formulas (III) to (XXV) or one of their salts are particularly preferred as preservatives in beverages, very particularly preferably in juices, nectars, soft drinks, milk-containing products, whey-containing drinks and yoghurt drinks.
  • the U. maydis strain ACD 04507fxxx000001 was isolated from spores of an affected corncob in September 2010. The sample comes from the federal state of Brandenburg in Germany. The
  • the strain was maintained by freezing a suspension in a glycerol-containing freezing solution at -80 ° C.
  • special 500 mL Erlenmeyer flasks 500 mL Erlenmeyer flasks with two opposing punctures are approximately 2.5 cm long, between 2 and 3 cm above the bottom of the flask and at an angle of 30 ° C to the horizontal
  • the preculture flasks were incubated on an orbital shaker with a 50 mm shaking radius at a shaking speed of 200 rpm and 24-25 ° C. for two days.
  • the main culture was carried out in just such Erlenmeyer flasks with 100 mL GLO1 medium (50 g / L glucose, 1.7 g / L Yeast Nitrogen base, pH 6.5, the glucose and Yeast Nitrogen Base solutions were separated autoclaved). The flasks were inoculated with 10 mL each of the preculture.
  • GLO1 medium 50 g / L glucose, 1.7 g / L Yeast Nitrogen base, pH 6.5, the glucose and Yeast Nitrogen Base solutions were separated autoclaved.
  • the flasks were inoculated with 10 mL each of the preculture.
  • the inoculated flasks were incubated on an orbital shaker with a 50 mm shaking radius at a shaking speed of 200 rpm and 24-25 ° C for five days.
  • Example 2 126 pistons of the main culture acc.
  • Example 2 were harvested in 1 L centrifuge beakers and centrifuged in a Heraeus Sepatech centrifuge at 5300 g for 20 min. The sediment thus obtained was frozen and lyophilized. The extraction was carried out with methanol and was supported by 15 min treatment in an ultrasonic bath and shaking for 15 min. After a filter ration, the sediment was again extracted in the same way with methanol.
  • the isolation of the compounds contained was carried out by a two-step process.
  • the extract grown on Celite was fractionated by medium pressure chromatography (MPLC) on RP-18 (200 x 50 mm) with a gradient (methanol-water) of 57-90% methanol at a flow rate of 30 mL / min (see Table 1).
  • MPLC medium pressure chromatography
  • DSM 2498 and DSM 62841 were frozen at ⁇ 80 ° C and used directly; the titer of the frozen suspensions was determined by plating on agar plates.
  • the inoculum was prepared from single colonies of freshly grown agar plates, typically overnight cultures.
  • the titer of the inoculum suspension is determined approximately by measuring the absorbance at 625 nm. If this corresponds to the absorption of McFarland Standard 0.5, a titer of 10 8 is assumed.
  • the test is carried out in U-bottom polystyrene 96well plates. Test substances are typically dissolved in DMSO, DMSO water or water. Table 7:
  • the calculated titre of the strains after inoculation is reproduced in Table 7. Anaerobically growing strains are grown using the BD GasPak EZ anaerobic system ⁇ BD, Tullastr. 8-12, 69126 Heidelberg, Germany). The BreathEasy Pole (Diversified Biotech, 65 Commerce Way, Dedham, MA 02026, USA) prevents contamination of adjacent wells with fungal spores.
  • the growth is evaluated by means of a binocular and other optical aids.
  • Aa Alicyclobacillus acidoterrestris DSM
  • Gl Gluconacetobacter liquefaciens DSM 5603
  • Aa Alicyclobacillus acidoterrestris DSM 2498
  • Gl Giuconacetobacter liquefaciens DSM 5603
  • Example 5 Various strains of microorganisms were incubated as set forth in Example 5 in the presence of various concentrations of the glycolipids (XIII), (V), (VIII), (IX), (XI), (XXII), and the glycolipid mixture AW-048 , In contrast to Example 5, the microorganisms were incubated in Getrankematrices. Table 10 lists the drinks used. By plating the inoculated drinks after 1 day, 1 week, 2 weeks and 4 weeks on suitable agar media, the preservative effect was checked. A substance was considered conservative if there was no increase in cell titer for 4 weeks. The mycel-forming fungi were additionally examined by binocular for hyphae growth.
  • Table 11 gives an overview of the preservative effects of the glycolipids and glycolipid mixtures.
  • Vitaperle energy 111 g / L sugar taurine, caffeine, B vitamins, carbon dioxide
  • Aa ⁇ licyclobacillus acidoterrestris DSM 2498
  • Gl Gluconacetobacter liguefaciens DSM 5603
  • 25, 100, 300 ... preserving effect at a concentration of 25, 100, 300 ... g / mL; > 600,> 1800 no preservative effect at the maximum used concentration of 600 g / mL or 1800 g / mL
  • the pseudozyma sp. Strain ACD 01658fxxxOOOOll was isolated from a soil sample in December 2002. The sample comes from the Rift Valley in Kenya. The strain was maintained by freezing a suspension in a glycerol-containing freezing solution at -80 ° C.
  • the strain ACD 01658fxxxOOOOll was on June 20, 2012 at the DSMZ (German Collection of Microorganisms and Cell Cultures GmbH, Inhoffenstr 7 B, D-38124 Braunschweig) under the number DSM 26076 according to Budapest Treaty by the company Analyticon Discovery GmbH (Hermannswerder house 17, 14473 Potsdam, Germany).
  • the main culture was carried out in special 500 mL Erlenmeyer flasks (500 mL Erlenmeyer flasks with two opposite punctures, the punctures being about 2.5 cm long, between 2 and 3 cm above the bottom of the flask and at an angle of 30 ° C Arranged horizontally; the flasks are sterile-capped with polyurethane foam stoppers of 50 mm in length and 40 mm in diameter) with 200 ml of SGCH1 medium (10 g / l L-glutamic acid monosodium salt monohydrate, 30 g / l sucrose, 0.15 g / l dihydrochloride).
  • the trace element solution contains 0.01 M sulfuric acid per liter of 1.5 g FeSO 4 .7H 2 O, 0.9 g ZnSO 4 .7H 2 O, 0.4 g MnS0 4 x H 2 0, 0.55 g CuS0 4 x 5 H 2 0, 0.6 g of Co (N0 3) 2 x 6 H 2 0, 0.25 g of boric acid and 0.2 g of Na 2 Mo0 4 x 2 H 2 0).
  • the main culture flasks were inoculated with 2.5 ml of homogenized preculture per Erlenemeyer flask and incubated on an orbital shaker with a 50 mm shaking radius at a shaking speed of 200 rpm and 24-25 ° C. for seven days.
  • Example 9 was shaken after addition of about 5% by volume of Diaion HP20 adsorbent resin after 45 minutes and then harvested in 1 L centrifuge beaker and centrifuged in a Heraeus Sepatech centrifuge at 5300 g for 20 min. The sediment thus obtained was extracted twice with acetone. The extraction was carried out with 15 min treatment in an ultrasonic bath and shaking for 15 min. After filtration, the sediment was again extracted in the same way with acetone.
  • Example 11 Isolation The isolation of the compounds contained was carried out by a two-step process.
  • the extract grown on celite was fractionated by medium pressure chromatography (MPLC) on RP-18 (200 x 50 mm) with a gradient (methanol-water) of 57-90% methanol at a flow rate of 30 mL / min (see Table 12).
  • MPLC medium pressure chromatography
  • the biomass sediment centrifuged from the fermentation of Ustilago maydis contains Ustilagin yarnren and Ustilipide.
  • the extraction with solvent, the precipitation from aqueous solution and a subsequent enrichment of the urstilaginic acids by degreasing were carried out to remove the ustilipids.
  • the extract is mixed with 50 ° C warm methanol, filtered and the resulting extract reduced in volume. After addition of 9 times the volume of water (preheated to 50 ° C.) precipitation takes place by cooling to room temperature and position. for two days at 4 ° C.
  • the urstilagic acid-containing precipitate is separated by means of a centrifuge, washed with cold water and dried after repeated degreasing with methyl tert-butyl ether (MTBE).
  • MTBE methyl tert-butyl ether
  • Example 13 Analytical data for AW-048 product
  • the content determination by HPLC-ELSD method gives> 99% U-stilaginic acids in total.
  • 1 shows the HPLC ELSD chromatogram of an enriched urstilagic acid fraction (glycolipid mixture AW-048 product).
  • Example 15 Olfactory assessment of the glycolipid-containing product AW-048
  • Example 16 Taste assessment of a solution of the substance NP-018256 (XI) Substance NP-018256 (purity 98.4% according to HPLC method 3, tabular details see above) was dissolved in a concentration of 50 ppm in still mineral water with heating to 60 ° C. The prepared solution, after cooling to room temperature, was evaluated by nine subjects according to the taste-and-spit method, and as a result, two subjects found no difference in comparison to water, and two other subjects described the solution as neutral were able to differentiate between the solution and water, the taste was not described as unpleasant and the substance did not adversely affect the taste of beverages at the concentration tested.
  • Example 17 Taste Assessment of AW-048 in Drinks AW-048 solutions of 50 ppm were prepared in various beverages as described in Example 15 for water. In addition to an apple spritzer, an orange platter and an ice tea, an energizer drink and a drink whey were also used. Three subjects were unable to discriminate between the original drinks and drinks with AW-048. In summary it could be stated that no taste impairment of the drinks by AW-048 takes place.
  • Example 18 Preparation of an apple spritzer with AW-048
  • Example 22 Preparation of a drinking whey with AW-048

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Abstract

L'invention concerne une boisson contenant, comme conservateur naturel, un glycolipide de formule (I), dans laquelle n = 1 ou n = 2, les radicaux R1 sont identiques ou différents et représentent H ou COCH3, les radicaux R2 sont identiques ou différents et représentent H ou (a), m valant 1, 2 ou 3, les radicaux R3 sont identiques ou différents et représentent H ou OH et les radicaux R4 représentent OH ou OCH3, les radicaux R5 représentent H (b) ou (a), m valant 1, 2 ou 3, les radicaux R6 représentent H ou OH, les radicaux R 7 représentent H ou OH ou =O, ou un sel du glycolipide.
PCT/EP2012/067823 2011-09-16 2012-09-12 Boisson contenant des glycolipides en tant que conservateurs WO2013037818A2 (fr)

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DE102011082891A DE102011082891A1 (de) 2011-09-16 2011-09-16 Konservierungsmittel enthaltend Glykolipide
DE102011082891.5 2011-09-16

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WO2013037818A9 true WO2013037818A9 (fr) 2013-05-10
WO2013037818A3 WO2013037818A3 (fr) 2014-04-17

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WO2014192682A1 (fr) * 2013-05-31 2014-12-04 東洋紡株式会社 Agent d'activation contenant un cellobiose lipide en tant qu'ingrédient actif et agent favorisant la production de collagène
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DE102018220913A1 (de) * 2018-12-04 2020-06-04 Beiersdorf Ag O/W-Emulsion mit Rhamnolipiden
EP4316459A1 (fr) 2022-08-05 2024-02-07 BRAIN Biotech AG Composition de conservation
WO2024029635A1 (fr) * 2022-08-05 2024-02-08 Suntory Holdings Limited Boisson présentant une inhibition de la croissance microbienne
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WO2013037818A3 (fr) 2014-04-17

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