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WO2015044222A1 - Formulations stables pour colorer des boissons et des produits alimentaires - Google Patents

Formulations stables pour colorer des boissons et des produits alimentaires Download PDF

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Publication number
WO2015044222A1
WO2015044222A1 PCT/EP2014/070400 EP2014070400W WO2015044222A1 WO 2015044222 A1 WO2015044222 A1 WO 2015044222A1 EP 2014070400 W EP2014070400 W EP 2014070400W WO 2015044222 A1 WO2015044222 A1 WO 2015044222A1
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WO
WIPO (PCT)
Prior art keywords
formulation
range
dehydroplectaniaxanthin
stable
products
Prior art date
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Ceased
Application number
PCT/EP2014/070400
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English (en)
Inventor
Hansjoerg Grass
Andrea Hitzfeld
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DSM IP Assets BV
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DSM IP Assets BV
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Filing date
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Application filed by DSM IP Assets BV filed Critical DSM IP Assets BV
Publication of WO2015044222A1 publication Critical patent/WO2015044222A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Preparation or treatment thereof
    • A23L2/52—Adding ingredients
    • A23L2/58—Colouring agents
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L5/00—Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
    • A23L5/40—Colouring or decolouring of foods
    • A23L5/42—Addition of dyes or pigments, e.g. in combination with optical brighteners
    • A23L5/43—Addition of dyes or pigments, e.g. in combination with optical brighteners using naturally occurring organic dyes or pigments, their artificial duplicates or their derivatives
    • A23L5/44—Addition of dyes or pigments, e.g. in combination with optical brighteners using naturally occurring organic dyes or pigments, their artificial duplicates or their derivatives using carotenoids or xanthophylls
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23P—SHAPING OR WORKING OF FOODSTUFFS, NOT FULLY COVERED BY A SINGLE OTHER SUBCLASS
    • A23P10/00—Shaping or working of foodstuffs characterised by the products
    • A23P10/30—Encapsulation of particles, e.g. foodstuff additives

Definitions

  • the present invention is directed to stable formulations comprising 2'-dehydro- plectaniaxanthin embedded in a matrix of modified food starch.
  • Such formulations are compositions which cannot be found in nature as such and which may preferably be manufactured as disclosed in EP-A 937 412, EP-A 807 431 and EP-A 1 008 380.
  • the formulations, as well as the beverages and the food products containing such formulations do not contain any artificial azo dyes. Furthermore it is desired that the color of such beverages and food products containing natural colorants is the same or nearly the same color of the beverages and food products that contained the artificial azo dyes. Thus, the color appearance of such beverages and food products should be maintained and not changed.
  • the 2' -dehydroplectaniaxanthin formulations according to the present invention whereby the 2'-dehydroplectaniaxanthin is embedded in a matrix of modified food starch.
  • the 2'-dehydroplectaniaxanthin is protected against degradation by oxidation.
  • these formulations give an intense orange color to beverages and food products they are incorporated in.
  • the color hue of the 2'-dehydroplectaniaxanthin formulations of the present invention is in the range of from 55 to 75 if said formulation is mixed with water so that the mixture contains 5 to 10 ppm of 2'-dehydroplectaniaxanthin. In this concentration the mixture with water looks orange. If the 2'- dehydroplectaniaxanthin is, however, used in a concentration of 50 ppm, such mixture looks red. Therefore, the formulations of the present invention can be used to color beverages and food products with an orange to red color.
  • 2'-Dehydroplectaniaxanthin is the compound of formula I.
  • the term "2'-dehydro- plectaniaxanthin” not only encompasses the (all-E)-isomer, but also any of its mono-, oligo- or poly-(Z)-isomers. It can be obtained from natural sources or by chemical synthesis.
  • plectaniaxanthin (compound of formula II) has been described in e.g. yeast, including e.g. Basidiomycetes, in particular Dioszegia sp. (Madhour et al., Phytochemistry 2005, 66, 2617-2626), wherein lycopene is transformed via ⁇ - carotene and torulene to plectaniaxanthin. Plectaniaxanthin can then be oxidized to 2'-dehydroplectaniaxanthin. A chemical synthesis of 2' -dehydroplectaniaxanthin is e.g. described in EP-A 630 578.
  • the formulation according to the present invention comprises preferably 0.1 to 25 weight-%, more preferably 0.5 to 20.0 weight-%, even more preferably 1 to 15.0 weight-%, most preferably 5.0 to 10.0 weight-%, of 2'-dehydroplectaniaxanthin, based on the total weight of the formulation.
  • a modified food starch is a food starch that has been chemically modified by known methods to have a chemical structure which provides it with a hydrophilic and a lipophilic portion.
  • the modified food starch has a long hydrocarbon chain as part of its structure (preferably C5-C18).
  • At least one modified food starch is preferably used to make a formulation of this invention, but it is possible to use a mixture of two or more different modified food starches in one formulation.
  • Starches are hydrophilic and therefore do not have emulsifying capacities.
  • modified food starches are made from starches substituted by known chemical methods with hydrophobic moieties.
  • starch may be treated with cyclic dicarboxylic acid anhydrides such as succinic anhydrides, substituted with a hydrocarbon chain (see 0. B. Wurzburg (editor), "Modified Starches:
  • a particularly preferred modified food starch of this invention has the following formula (I)
  • St is a starch
  • R is an alkylene radical
  • R ' is a hydrophobic group
  • R is a lower alkylene radical such as dimethylene or trimethylene.
  • R ' may be an alkyl or alkenyl group, preferably having 5 to 18 carbon atoms.
  • a preferred compound of formula (I) is an "OSA-starch” (starch sodium octenyl succinate).
  • the degree/extent of substitution, i.e. the number of esterified hydroxyl groups to the number of free non -esterified hydroxyl groups usually varies in a range of from 0.1% to 10%, preferably in a range of from 0.5% to 4%, more preferably in a range of from 3% to 4%.
  • OSA-starch denotes any starch (from any natural source such as corn, waxy maize, waxy corn, wheat, tapioca and potato or synthesized) that was treated with octenyl succinic anhydride (OSA).
  • the degree/extent of substitution i.e. the number of hydroxyl groups esterified with OSA to the number of free non- esterified hydroxyl groups usually varies in a range of from 0.1% to 10%, preferably in a range of from 0.5% to 4%, more preferably in a range of from 3% to 4%.
  • OSA- starches are also known under the expression "modified food starch".
  • OSA-starches encompasses also such starches that are commercially available e.g. from National Starch /Ingredion under the tradenames HiCap 100, Capsul, Capsul HS, Purity Gum 2000, Clear Gum Co03, UNI-PURE, HYLON VII; from National Starch /Ingredion and Roquette Freres, respectively; from CereStar under the tradename C * EmCap or from Tate & Lyle.
  • a commercially available modified food starch such as e.g. HiCap 100 (from National Starch/lngredion) and ClearGum Co03 (from Roquette Freres) is used. It is especially advantageous if such a starch or an OSA starch in general is further improved according to a process as disclosed in WO 2007/090614, especially according to a procedure as described in examples 28, 35 and/or 36 of WO 2007/090614.
  • centrifuged as an aqueous solution or suspension before use has been centrifuged as an aqueous solution or suspension before use.
  • the centrifugation may be carried out at 1000 to 20000 g depending on the dry mass content of the modified food starch in the aqueous solution or suspension. If the dry mass content of the modified food starch in the aqueous solution or suspension is high, the applied centrifugation force is also high. For example for an aqueous solution or suspension with a dry mass content of the modified food starch of 30 weight-% a centrifugation force of 12000 g may be suitable to achieve the desired separation.
  • the centrifugation may be carried out at dry matter contents in the range of from 0.1 -60 weight-%, preferably in the range of from 10-50 weight-%, most preferably in the range of from 15-40 weight-% at temperatures in the range of from 2-99 °C, preferably in the range of from 10-75°C, most preferably in the range of from 40- 60°C.
  • the formulation according to the present invention comprises preferably 60 to 99.8 weight-%, more preferably 70 to 90 weight-%, of modified food starch based on the total weight of the formulation, whereby the preferred modified food starch is commercially available OSA-starch, which is preferably further improved by separating off insoluble parts as disclosed e.g. in WO 2007/090614 (examples for centrifugation and microfiltration). If a mixture of two or more modified food starches is present the total amount is also in the ranges as given above.
  • Suitable fat-soluble antioxidants are known to the person skilled in the art.
  • fat-soluble antioxidants are used that are approved for their application in food products and beverages.
  • Preferred fat-soluble antioxidants are selected from the group consisting of tocopherols, e.g. dl-a-tocopherol (i.e. synthetic tocopherol), d-a-tocopherol (i.e. natural tocopherol), ⁇ - or ⁇ -tocopherol, or a mixture of two or more of these.
  • tocopherols e.g. dl-a-tocopherol (i.e. synthetic tocopherol), d-a-tocopherol (i.e. natural tocopherol), ⁇ - or ⁇ -tocopherol, or a mixture of two or more of these.
  • the most preferred fat-soluble antioxidant is dl-a-tocopherol.
  • the total amount of the fat-soluble antioxidants in the formulation according to the present invention is in the range of from 0 to 1.5 weight-%, more preferably it is in the range of from 0.01 to 1 .0 weight-%, most preferably it is in the range of from 0.1 to 0.5 weight-%, based on the total weight of the
  • Suitable water-soluble antioxidants are known to the person skilled in the art. Preferably water-soluble antioxidants are used that are approved for their application in food products and beverages. Preferred water-soluble antioxidants are selected from the group consisting of citric acid, citric acid salts, ascorbic acid, ascorbic acid salts (preferably sodium ascorbate), as well as any mixture thereof. Preferred water-soluble antioxidants are ascorbic acid, sodium ascorbate and citric acid.
  • the total amount of the water-soluble antioxidants in the formulation according to the present invention is in the range of from 0.1 to 4.0 weight-%, more preferably it is in the range of from 0.1 to 2.0 weight-%, based on the total weight of the formulation.
  • a preferred embodiment of the present invention is a stable formulation consisting of 2'-dehydroplectaniaxanthin, a starch that was treated with octenyl succinic anhydride, and an antioxidant, whereby the antioxidant can be fat-soluble or water-soluble, with the preferred amounts as given above.
  • Such formulation shows an intense orange or red color or a color shade in between.
  • the formulations of the present invention may further contain an oil.
  • the amount of said oil is preferably in the range of from 0 to 5.0 weight-%, more preferably in range of from 0.01 to 1 .0 weight-%, most preferably in the range of from 0.5 to 1 .0 weight-%, based on the total weight of the formulation.
  • oil in the context of the present invention encompasses glycerol and any triglyceride such as vegetable oils or fats like corn oil, sunflower oil, soybean oil, safflower oil, rapeseed oil, peanut oil, palm oil, palm kernel oil, cotton seed oil, olive oil or coconut oil.
  • oils can be from any origin. They can be natural, modified or synthetic, whereby natural oils are preferred. If the oils are natural they can be plant or animal oils, whereby plant oils are preferred.
  • the present invention is further related to a process for the manufacture of a formulation according to the present invention comprising the following steps: a) forming a solution of 2'-dehydroplectaniaxanthin in an organic solvent, optionally adding a fat-soluble antioxidant and /or an oil;
  • step c) emulsifying the solution obtained in step a) into the matrix obtained in step b) to obtain an emulsion
  • step d) removing the organic solvent from the emulsion obtained in step c) to obtain a liquid formulation
  • step e) optionally drying the liquid formulation obtained in step d) to obtain the solid formulation.
  • An oil can also be added. If it is, however, added, the amount is chosen so that the final amount of the oil in the resulting formulation after having performed all steps is as described above.
  • the amounts of 2'-dehydroplectania- xanthin and the fat-soluble antioxidant (if present) are chosen so that the final amounts of these compounds in the resulting formulation after having performed all steps is as described above.
  • the amount of the solvent and the dissolution temperature are chosen so as to dissolve the 2'-dehydroplectaniaxanthin, the fat-soluble antioxidant, if present, and the oil, if present, completely. Usually it is necessary to heat up the suspension obtained when mixing all compounds present in this step to get a solution.
  • the temperature to which the suspension is heated up is in the range of from 40 to 90 °C, more preferably that temperature is in the range of from 40 to 86 °C. After having obtained the solution it is usually kept at the temperature it was before heated up to. Step b)
  • this step is performed at a temperature in the range of 50 to 70° C, more preferably at a temperature in the range of 55°C to 67°C, even more preferably at a temperature of around 60 °C.
  • the matrix obtained after having performed step b) is then preferably kept at a temperature in the range of 25 to 65 °C, more preferably at a temperature in the range of 29°C to 66°C, even more preferably at a temperature in the range of 29 to 56°C.
  • this step is performed at a mixing temperature in the range of 25 to 100°C, more preferably at a mixing temperature in the range of 30 to 80°C, even more preferably at a mixing temperature in the range of 35° C to 75° C to obtain an emulsion.
  • the emulsification can be achieved by using a rotor-stator device or a high pressure homogenizer or both. Other devices known to the person skilled in the art may also be used. If rotor-stator device and/or a high pressure homogenizer is used, a pressure drop in the range of 100 to 1000 bar, more preferably in the range of 150 to 300 bar, is preferably applied. Step d)
  • the organic solvent may e.g. be removed by using a thin film evaporator cascade (preferred). Other methods known to the person skilled in the art are also applicable.
  • the resulting liquid formulations can already also be incorporated in beverages and food products to color them with an intense orange color.
  • the resulting liquid formulations after having performed steps a) to d) can also be dried by any method known to the person skilled in the art, e.g. by spray-drying, spray-drying in combination with fluidised bed granulation or by a powder-catch technique, whereby the sprayed emulsion droplets are caught in a bed of an absorbent, such as starch, and subsequently dried.
  • any method known to the person skilled in the art e.g. by spray-drying, spray-drying in combination with fluidised bed granulation or by a powder-catch technique, whereby the sprayed emulsion droplets are caught in a bed of an absorbent, such as starch, and subsequently dried.
  • formulations of the present invention are prepared according to the process of the present invention.
  • the present invention is also directed to the formulation as obtained by the process as described above.
  • formulations according to the present invention are used for the enrichment, fortification and /or coloration of beverages and food products; said use being a further aspect of the invention.
  • Beverages wherein the formulations of the present invention can be used as a colorant or a functional ingredient can be non-alcoholic, flavoured drinks, e.g. flavoured seltzer waters, soft drinks, mineral drinks, flavoured waters, fruit juices, fruit nectars, fruit punches and concentrated forms of these beverages. They may be based on natural fruit or vegetable juices or on artificial juice flavours, and they may be carbonated or non-carbonated. Alcoholic beverages, instant beverage powders, sugar-containing beverages and diet beverages containing non-calorific or artificial sweeteners are further examples of beverages which, by virtue of their containing the 2'-dehydroplectaniaxanthin formulations, are embraced by the present invention.
  • flavoured drinks e.g. flavoured seltzer waters, soft drinks, mineral drinks, flavoured waters, fruit juices, fruit nectars, fruit punches and concentrated forms of these beverages. They may be based on natural fruit or vegetable juices or on artificial juice flavours, and they may be carbonated or
  • the final concentration of the 2'-dehydroplectaniaxanthin which is added via the formulations of the present invention to beverages may be from 0.1 to 200 ppm (from 0.1 to 100 ppm, from 0.1 to 50 ppm), particularly from 1 to 30 ppm, more preferably from 3 to 20 ppm, based on the total weight of the beverage and depending on the particular beverage to be colored or fortified and the intended grade of coloration or fortification.
  • sweet products containing the 2'-dehydroplectaniaxanthin as a coloring agent said sweet products including sugar coated confectionery products, e.g. chocolate lentils, boiled sweets, gums, chewing gums, jellies, toffees, hard sugar candies, soft sugar candies, and fudges, as well as chocolate confectionary products; and desserts, including frozen desserts, e.g. sorbets, puddings, instant pudding powders and preserves.
  • fruit preparations used for dairy products and cereals may also be colored with the 2' -dehydroplectaniaxanthin formulations, and such colored fruit preparations are also food products in accordance with the present invention.
  • Sweet products especially hard and soft sugar candies, and beverages are especially preferred.
  • dairy products obtained from natural sources are within the scope of the food products in which the 2'-dehydroplectaniaxanthin formulations are present, and as such embraced by the present invention.
  • dairy products are milk drinks, butter, cheese, ice cream, yoghurt, yoghurt drinks and the like.
  • Milk substitute products such as soy milk products and synthetically produced milk substitute products are also included in the food products containing the 2'-dehydroplectaniaxanthin formulations according to the present invention.
  • fat-based products e.g. spreads, including low fat spreads and margarine; low calorific food products containing natural or synthetically produced fat replacers; cereals and cereal products, e.g. cookies, cakes and pasta; and snacks, e.g. extruded or non-extruded potato-based products, all of which contain the 2'-dehydroplectaniaxanthin formulations as a coloring or fortifying agent.
  • Still further food products which can be colored with 2'-dehydroplectaniaxanthin formulations are such miscellaneous products as soups; sauces, e.g. mayonnaise and salad dressings; seasonings; and tofu products; and any compounded foods which contain one or more of the above-mentioned food products.
  • the total concentration of the 2'-dehydroplectaniaxanthin used as a coloring agent in the food products in accordance with the present invention may be from 0.1 to 500 ppm, preferably from 1 to 50 ppm, based on the total weight of the food product.
  • concentration range in any particular case depends on the particular food product to be colored and on the intended grade of coloration in such food product.
  • the beverages or food products of this invention are obtained by adding to or incorporating in the beverage or food product - at a suitable stage in its
  • the formulation of this invention can be used according to methods per se known for the application of water- or oil- dispersible solid or liquid forms to beverages or food products, as appropriate.
  • the 2'-dehydroplectaniaxanthin formulation may in general be added either as an aqueous stock solution, a dry powder mix or a pre-blend with other suitable food ingredients according to the specific application.
  • Mixing can be effected for example using a dry powder blender, a shear mixer or a homogenizer, depending on the required nature of the final food product or beverage.
  • the particular mixing procedure and amount of oily or aqueous ingredients may influence the color of the final food product or beverage. As will be readily apparent, such technicalities are within the skill of the expert in the art of beverage and food manufacture and formulation.
  • the beverages and food products colored by the 2'-dehydroplectaniaxanthin formulations show an intense orange or red color or a color shade in between. Furthermore such beverages show a low turbidity, preferably a turbidity of ⁇ 150 NTU, more preferably a turbidity of ⁇ 100 NTU.
  • (Amax-A650) means the value you get when you substract the Adsorption value measured at 650 nm ("A650”) wavelength from the value ("Amax”) that was measured at the maximum Adsorption in the UV-Spectrophotometer.
  • weight of sample the amount/weight of the beadlet that was used in [g]
  • content of product form in % "the amount of 2'-dehydroplectaniaxanthin in the beadlet in %” which is 5.2 in the present case.
  • E1 / 1 com. in H 2 0 ( ⁇ max) 755 (408 nm)
  • Example 1 may be repeated, but no corn oil added.
  • Example 3
  • Example 1 may be repeated, but a different oil may be used.
  • Example 4 Preparation of a soft drink with the formulation according to example 1
  • the soft drink has the following composition:
  • the soft drink was prepared as follows:
  • Potassium sorbate 1 was dissolved in water, the other ingredients 2) were added one after the other while the mixture was gently stirred. Then the resulting soft drink syrup was diluted with drink water in such an amount to result in 1000 ml of the soft drink.
  • the pH of the soft drink was in the range of 3.0 to 3.5.
  • the soft drink was then filled in a glass bottle and the bottle sealed with a metallic cap.
  • the bottle was pasteurized for approximately 1 min at 80 ° C using a tunnel pasteurizer (Miele, Switzerland).
  • Suspended solids are responsible for the turbid appearance of beverages containing juice. This turbid appearance can be evaluated by turbidity measurements. Turbidity depends on the light-scattering properties of such particles: their size, their shape and their refractive index.
  • turbidity measurements were conducted using a Turbidimeter (Hach 2100N IS®, USA) and turbidity values were given in NTU (nephelometric turbidity units). Neophelometer measures the light scattered by a sample in 90° from the incident light path.
  • Color measurements for the application in food are performed with a colorimeter (Hunter Lab Ultra Scan Pro) which can other than a spectrophotometer express color values according to the psychophysical perception of color by human eye. Color measurements are carried out after CIE guidelines (Commission International d'Eclairage). Values can be expressed either as planar coordinates L*a*b* with L* being the measuring value for lightness, with a*being the value on the red-green- axis and with b* being the value on the yellow-blue-axis.
  • a soft drink was prepared using ⁇ -carotene 10% CWS/S (commercially available from DSM Nutritional Products Ltd., Kaiseraugst, Switzerland), whereby the concentration of the ⁇ -carotene in the soft drink was also 10 ppm.
  • Example 4 The results of example 4 and the comparative example are also shown in Fig. 1 .
  • the soft drink prepared with the 2' -dehydroplectaniaxanthin formulation according to example 1 is much less turbid than the one prepared with ⁇ -carotene 10% CWS/S and of a similar color.
  • Example 5 Preparation of hard sugar candies with the formulation according to example 1
  • a 2'-dehydroplectaniaxanthin stock solution containing 15 g of the formulation according to example 1 and 85 g of de-ionized water are prepared. 10 g of this 2'- dehydroplectaniaxanthin stock solution are mixed with 490 g of a sugar solution (67-78° Brix) at a temperature of 65° C under stirring and kept at this temperature resulting in a colored syrup.
  • Chocolate lentils are pre-coated with a pure sugar solution (without 2'- dehydroplectaniaxanthin) thus providing chocolate lentils with a white center.
  • a white pigment like titaniumdioxide may be added to the pure sugar syrup and the chocolate lentils may be coated with 10 to 20 layers of this white sugar syrup before they are coated with the colored layers.
  • a small amount of colored syrup is poured over the lentils and homogenously distributed in the drum at moderate speed.
  • the thus colored lentils are dried with cold air (15 °C-18°C, relative humidity in the range of 40-50%) at moderate speed resulting in one layer. These steps are repeated (usually 20 to 50 times) until the desired color intensity (either orange or red depending on how many layers are put on) is achieved.
  • the hard panned candy has a smooth surface aspect which is enhanced by final glazing layers.
  • the external layers are made of crystalized sugar. According to the sugar layer thickness, the candy offers a lightly or hard crunchy bite.

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  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Nutrition Science (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
  • Non-Alcoholic Beverages (AREA)

Abstract

La présente invention concerne des formulations stables comprenant le composé 2'-déshydro-plectaniaxanthine intégré dans une matrice d'amidon alimentaire modifié, des procédés de production de ces formulations, et leur utilisation pour colorer, enrichir ou fortifier des boissons et des produits alimentaires, ainsi que des boissons et des produits alimentaires présentant une couleur orange à rouge.
PCT/EP2014/070400 2013-09-24 2014-09-24 Formulations stables pour colorer des boissons et des produits alimentaires Ceased WO2015044222A1 (fr)

Applications Claiming Priority (2)

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CH01658/13 2013-09-24
CH16582013 2013-09-24

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WO2015044222A1 true WO2015044222A1 (fr) 2015-04-02

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4844934A (en) * 1986-03-26 1989-07-04 Basf Aktiengesellschaft Preparation of finely divided, water-dispersable carotenoid formulations
US5670548A (en) * 1993-06-24 1997-09-23 Roche Vitamins Inc. Pigmentation with carotenoids
EP0807431A2 (fr) * 1996-05-14 1997-11-19 F. Hoffmann-La Roche Ag Procédé pour la fabrication de compositions de caroténoides
US20080113076A1 (en) * 2006-07-07 2008-05-15 Sensient Food Colors Germany Gmbh & Co. Kg Method to Prepare a Stable High-Load Paprika Extract in Powder Form
EP1964479A1 (fr) * 2007-02-14 2008-09-03 DSMIP Assets B.V. Processus de fabrication d'une poudre contenant des caroténoides
WO2009071286A1 (fr) * 2007-12-05 2009-06-11 Dsm Ip Assets B.V. Formulation pulvérulente d'un ingrédient actif liposoluble

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4844934A (en) * 1986-03-26 1989-07-04 Basf Aktiengesellschaft Preparation of finely divided, water-dispersable carotenoid formulations
US5670548A (en) * 1993-06-24 1997-09-23 Roche Vitamins Inc. Pigmentation with carotenoids
EP0807431A2 (fr) * 1996-05-14 1997-11-19 F. Hoffmann-La Roche Ag Procédé pour la fabrication de compositions de caroténoides
US20080113076A1 (en) * 2006-07-07 2008-05-15 Sensient Food Colors Germany Gmbh & Co. Kg Method to Prepare a Stable High-Load Paprika Extract in Powder Form
EP1964479A1 (fr) * 2007-02-14 2008-09-03 DSMIP Assets B.V. Processus de fabrication d'une poudre contenant des caroténoides
WO2009071286A1 (fr) * 2007-12-05 2009-06-11 Dsm Ip Assets B.V. Formulation pulvérulente d'un ingrédient actif liposoluble

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