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WO2025206390A1 - Composition contenant du carotène et son procédé de production - Google Patents

Composition contenant du carotène et son procédé de production

Info

Publication number
WO2025206390A1
WO2025206390A1 PCT/JP2025/013005 JP2025013005W WO2025206390A1 WO 2025206390 A1 WO2025206390 A1 WO 2025206390A1 JP 2025013005 W JP2025013005 W JP 2025013005W WO 2025206390 A1 WO2025206390 A1 WO 2025206390A1
Authority
WO
WIPO (PCT)
Prior art keywords
carotene
containing composition
value
particles
color
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.)
Pending
Application number
PCT/JP2025/013005
Other languages
English (en)
Japanese (ja)
Inventor
圭剛 木下
剛 三内
優月 林
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.)
San Ei Gen FFI Inc
Original Assignee
San Ei Gen FFI Inc
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 San Ei Gen FFI Inc filed Critical San Ei Gen FFI Inc
Publication of WO2025206390A1 publication Critical patent/WO2025206390A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

Links

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
    • 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
    • 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
    • A61K8/31—Hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B61/00—Dyes of natural origin prepared from natural sources, e.g. vegetable sources
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0001—Post-treatment of organic pigments or dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0001—Post-treatment of organic pigments or dyes
    • C09B67/0003—Drying, e.g. sprax drying; Sublimation of the solvent
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0001—Post-treatment of organic pigments or dyes
    • C09B67/0014—Influencing the physical properties by treatment with a liquid, e.g. solvents
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/006—Preparation of organic pigments

Definitions

  • the present invention relates to a carotene-containing composition having a specific color tone and a method for producing the same.
  • Carotene is a typical carotenoid that ranges in color from red to yellow.
  • Known types include beta-carotene, which has a beta ring on both ends of the carotenoid skeleton, and alpha-carotene, which has a beta ring on one end. These are used as colorants (pigments) due to their color, and because they are converted into vitamin A (retinol) in the animal body and function as vitamin A, they are also used for nutritional fortification as provitamin A.
  • Carotene pigments are classified by their origin (synthetic, plant-derived, or algae-derived). Of these, synthetic carotene is beta-carotene, and in Japan it is treated as a designated food additive (INS160a(i)/E160a). Also in Japan, carrot carotene and palm oil carotene, which are plant-derived carotenes, and Dunaliella carotene, which is an algae-derived carotene, are approved as food, beverage, or pharmaceutical colorants (additives).
  • Carrot carotene and palm oil carotene contain approximately 60-70% beta-carotene, and are mixtures that also contain carotenoids such as lutein, zeaxanthin, canthaxanthin, and beta-cryptoxanthin.
  • Dunaliella carotene is 95% beta-carotene, and also contains alpha-carotene, lutein, zeaxanthin, etc.
  • Carotene is insoluble in water and only slightly soluble in fats and oils. For this reason, carotene is not suitable for uniformly or sufficiently coloring water-soluble substances (such as water-soluble foods and beverages), and even when administered to the body as provitamin A, there is the problem that the desired bioavailability is not achieved.
  • Patent Document 1 describes a method for reducing the crystal size of carotene by pulverizing carotene using a colloid mill to reduce the crystal size to a particle size of 2 to 10 ⁇ m.
  • Patent Documents 3 and 4 also describe a method for preparing a carotenoid-containing dry powder by dissolving one or more carotenoids or oxidized carotenoids in a water-miscible organic solvent or a mixed solvent of water and a water-miscible organic solvent, or by dissolving the resulting solution in a water-immiscible organic solvent and then dispersing the resulting solution in an aqueous solution of a mixture of lactose and at least one soy protein, removing water and other solvents from the resulting dispersion, and then drying the resulting dispersion.
  • Patent Document 5 describes a method for preparing a colored formulation of finely divided carotenoids by the steps of: (a) forming a suspension of carotenoids using a water-immiscible organic solvent, optionally containing an antioxidant and/or oil; (b) feeding the formed suspension into a heat exchanger and heating the suspension to 100-250°C; (c) rapidly cooling the prepared solution to 20-100°C; (d) removing the organic solvent; and converting the resulting dispersion into a powder formulation.
  • a water-immiscible organic solvent optionally containing an antioxidant and/or oil
  • Patent Document 6 also describes a method for producing a carotenoid dispersion by dispersing a carotenoid in dimethyl ether, a C4 hydrocarbon, or a mixture thereof in an aqueous phase in a supercritical or near-critical state, decompressing the mixture, and separating the dispersion from the gaseous solvent.
  • Patent Document 7 describes a method for producing a powdered carotenoid composition that is easily dispersed in an aqueous medium without using an organic solvent and/or a solubilizing oil, and that has high coloring power as well as good stability and bioavailability.
  • Patent Document 7 describes the following steps as a method for preparing a solid carotenoid powder containing 10 to 25% by weight of carotenoid particles having an average size of 0.1 to 0.5 ⁇ m: a) melting an aqueous suspension containing 10-25% carotenoid crystals by weight of the final powder and 0.1-6% surfactant by weight of the final powder by heating at a temperature sufficient to melt the carotenoid crystals; b) homogenizing the molten aqueous carotenoid suspension at a pressure ranging from 96.6 to 2759 bar (1400 to 40,000 psi) to obtain said carotenoid particles; c) drying the homogenized and molten aqueous carotenoid suspension to obtain said solid carotenoid powder.
  • a second object of the present invention is to provide a carotene-containing composition that has the specific color tone described above and also has emulsion stability (storage stability), turbidity, UHT sterilization resistance, acid resistance, salt resistance, and/or shaking resistance, as well as a method for producing the same.
  • a carotene-containing composition having spherical particles with a median diameter ( D50 ) of 0.15 to 0.55 ⁇ m can be obtained by crushing carotene crystals in the presence of water and an emulsifier without using organic solvents or oils until the median diameter ( D50 ) is 0.55 ⁇ m or less, and then treating the resulting particles with subcritical water to melt them and then cooling them.
  • the carotene-containing composition also has the desired color tone (hue angle ⁇ , a * value, and b * value) described above.
  • the carotene-containing composition has emulsion stability (storage stability), turbidity, UHT sterilization resistance, acid resistance, salt resistance, and/or shaking resistance.
  • emulsion stability storage stability
  • turbidity UHT sterilization resistance
  • acid resistance salt resistance
  • shaking resistance emulsion stability
  • turbidity UHT sterilization resistance
  • (I-5) The production method according to any one of (I-1) to (I-4), wherein the subcritical water treatment step in Step 2 is carried out in the presence of an emulsifier, and the emulsifier is at least gum ghatti.
  • (I-6) The production method according to any one of (I-1) to (I-5), wherein the subcritical water treatment step of step 2 is a step of treating the pulverized mixture prepared in step 1 at a temperature of 158 to 240°C and at a pressure equal to or greater than the saturated water vapor pressure for 0.1 to 60 seconds.
  • (II-2) A carotene-containing composition produced by any one of the production methods (I-1) to (I-9),
  • the carotene-containing composition is characterized in that, when the color tone of an aqueous solution of the carotene-containing composition adjusted with water to a carotene concentration of 10 ppm is evaluated using the L * a * b * color space color system, the hue angle ⁇ is 50° to 65°, the a * value is 20 to 40, and the b * value is 40 to 52.
  • (II-3) The carotene-containing composition according to (II-1) or (II-2), wherein the lightness L * value of an aqueous solution of the carotene-containing composition adjusted to a carotene concentration of 10 ppm is 70 to 85, preferably 73 to 80, more preferably 75 to 80.
  • (II-4) The carotene-containing composition according to any one of (II-1) to (II-3), wherein the chroma C value of an aqueous solution of the carotene-containing composition adjusted to a carotene concentration of 10 ppm is 50 to 65, preferably 53 to 62, and more preferably 53 to 60.
  • (II-5) A carotene-containing composition according to any one of (II-1) to (II-4), which contains 13-cis beta-carotene, 9-cis beta-carotene, and all-trans beta-carotene, and the proportion of all-trans beta-carotene relative to the total amount of these components (100% by mass) is 50% by mass or more.
  • (II-6) A carotene-containing composition according to any one of (II-1) to (II-5), which is used as an additive for foods and beverages, cosmetics, pharmaceuticals and/or quasi-drugs.
  • (II-7) The carotene-containing composition according to (II-6), wherein the additive is a pigment preparation.
  • (II-8) A carotene-containing composition according to any one of (II-1) to (II-7), which is a solid formulation.
  • (III) Composition colored with a carotene-containing composition
  • III-1 A colored composition containing the carotene-containing composition described in any one of (II-1) to (II-8).
  • III-2) The coloring composition according to (III-1), which is a food or drink, a cosmetic, a pharmaceutical, or a quasi-drug.
  • III-3) The coloring composition according to (III-1), wherein the coloring composition is an aqueous food or drink, cosmetic, pharmaceutical, or quasi-drug.
  • the present invention provides a carotene-containing composition having a specific color similar to that of CI FOOD YELLOW 3 (Sunset Yellow FCF, CAS RN: 2783-94-0) (Disodium 6-hydroxy-5-(4-sulfonatophenylazo)-2-naphthalene-sulfonate), and a method for producing the same.
  • the present invention provides a carotene-containing composition having a hue angle ⁇ of 50° to 65°, an a * value of 20 to 40, and a b * value of 40 to 52 when the color tone of an aqueous solution obtained by adjusting the carotene-containing composition with water so that the carotene concentration is 10 ppm is evaluated using the L * a*b * color space color system.
  • the present invention can provide a carotene-containing composition that has the specific color tone and also has emulsion stability (storage stability), turbidity, UHT sterilization resistance, acid resistance, salt resistance, and/or shaking resistance, as well as a method for producing the same.
  • emulsion stability storage stability
  • turbidity turbidity
  • UHT sterilization resistance acid resistance, salt resistance, and/or shaking resistance
  • a carotene-containing composition having the above-mentioned properties can be produced through a continuous and simple operation without using organic solvents and/or oils and fats.
  • beta-carotene exists in multiple cis-trans stereoisomers, including all-trans beta-carotene, 9-cis beta-carotene, 13-cis beta-carotene, 15-cis beta-carotene, 9,13-disis beta-carotene, and 9,13'-disis beta-carotene.
  • the carotene-containing composition of the present invention is sufficient as long as it contains at least all-trans beta-carotene as beta-carotene, and may contain other stereoisomers as well.
  • beta-carotene other than all-trans beta-carotene is preferably 9-cis beta-carotene and 13-cis beta-carotene.
  • ⁇ to ⁇ ( ⁇ and ⁇ are arbitrary numbers, but ⁇ > ⁇ ) means a range of "greater than ⁇ and less than ⁇ .”
  • the preferred ranges of the hue angle ⁇ , a * value, and b * value are as follows: Hue angle ⁇ : preferably 50° to 62°, more preferably 52° to 62°, even more preferably 53° to 62°, and still more preferably 53° to 61°. a * value: preferably 22 to 40, more preferably 22 to 36, even more preferably 23 to 35, even more preferably 24 to 35, and even more preferably 25 to 35. b * value: preferably 40 to 51, more preferably 41 to 51, even more preferably 42 to 50, even more preferably 42 to 49, and even more preferably 42 to 48. These hue angle ⁇ , a * value, and b * value can be arbitrarily selected and combined.
  • the combinations of the hue angle ⁇ , the a * value, and the b * value include all of the combinations shown in Table 1.
  • the combinations include a combination of the hue angle ⁇ , the a * value, and the b * value all in the same column, and may also be combinations in different columns.
  • the a * value when the hue angle ⁇ is in the range of one column, the a * value may be in one column and the b * value may be any combination selected from columns 2 to 6; the a * value may be in two columns and the b * value may be any combination selected from columns 1 to 6; the a * value may be in three columns and the b * value may be any combination selected from columns 1 to 6; the a * value may be in four columns and the b * value may be any combination selected from columns 1 to 6; the a * value may be in five columns and the b * value may be any combination selected from columns 1 to 6; or the a * value may be in six columns and the b * value may be any combination selected from columns 1 to 6.
  • the a * value can be any combination selected from column 1 and the b * value can be any combination selected from column 1 to column 6; the a * value can be any combination selected from column 2 and the b * value can be any combination selected from column 1 to column 6; the a * value can be any combination selected from column 3 and the b * value can be any combination selected from column 1 to column 6; the a * value can be any combination selected from column 4 and the b * value can be any combination selected from column 1 to column 6; the a * value can be any combination selected from column 5 and the b * value can be any combination selected from column 1 to column 6; or the a * value can be any combination selected from column 6 and the b * value can be any combination selected from column 1 to column 6.
  • the a * value can be any combination selected from column 1 and the b * value can be any combination selected from column 1 to column 6; the a * value can be any combination selected from column 2 and the b * value can be any combination selected from column 1 to column 6; the a * value can be any combination selected from column 3 and the b * value can be any combination selected from column 1 to column 6; the a * value can be any combination selected from column 4 and the b * value can be any combination selected from column 1 to column 6; the a * value can be any combination selected from column 5 and the b * value can be any combination selected from column 1 to column 6; or the a * value can be any combination selected from column 6 and the b * value can be any combination selected from column 1 to column 6.
  • the a * value can be any combination selected from column 1 and the b * value can be any combination selected from column 1 to column 6; the a * value can be any combination selected from column 2 and the b * value can be any combination selected from column 1 to column 6; the a * value can be any combination selected from column 3 and the b * value can be any combination selected from column 1 to column 6; the a * value can be any combination selected from column 4 and the b * value can be any combination selected from column 1 to column 6; the a * value can be any combination selected from column 5 and the b * value can be any combination selected from column 1 to column 6; or the a * value can be any combination selected from column 6 and the b * value can be any combination selected from column 1 to column 6.
  • the a * value can be any combination selected from 1 column and the b * value can be any combination selected from 1 to 6 columns; the a * value can be any combination selected from 2 columns and the b * value can be any combination selected from 1 to 6 columns; the a * value can be any combination selected from 3 columns and the b * value can be any combination selected from 1 to 6 columns; the a * value can be any combination selected from 4 columns and the b * value can be any combination selected from 1 to 6 columns; the a * value can be any combination selected from 5 columns and the b * value can be any combination selected from 1 to 6 columns; or the a * value can be any combination selected from 6 columns and the b * value can be any combination selected from 1 to 6 columns.
  • the carotene-containing composition may have any color tone in its aqueous solution (10 ppm) as described above in the L * a * b * color space color system, and the L * value, which indicates lightness, is not particularly limited, but is preferably 70 to 85, more preferably 72 to 83, and even more preferably 74 to 81.
  • the C value, which indicates saturation, is also not particularly limited, but is preferably 45 to 65, more preferably 46 to 63, more preferably 46 to 62, even more preferably 46 to 61, even more preferably 47 to 60, and even more preferably 50 to 60.
  • the median diameter ( D50 ) refers to the particle size at 50% of the cumulative value in the particle size distribution (volume basis) determined by a laser diffraction/scattering method.
  • the particle size at 50% of the cumulative value is the particle size at which 50% of the total number of particles is counted from the smallest particle size, and is also referred to as the " D50 value.”
  • spherical shape of the carotene particles contained in this carotene-containing composition can be confirmed using a microscope such as an optical microscope or a transmission electron microscope.
  • spherical does not mean a strict shape such as a perfect sphere, but rather a round shape like a ball. Irregular shapes whose shape cannot be identified are excluded.
  • this carotene-containing composition have a low proportion of coarse particles.
  • coarse particles means particles with a particle diameter of more than 1.3 ⁇ m.
  • the particle diameter referred to here is the volume-based particle diameter determined by laser diffraction/scattering method.
  • the carotene-containing composition described above can be produced by a method comprising the following steps: Step 1: wet-pulverizing carotene crystals in the presence of water and an emulsifier until the median diameter (D 50 ) is 0.55 ⁇ m or less to prepare a slurry-like pulverized mixture (pulverization step); Step 2: treating the pulverized mixture prepared in Step 1 with subcritical water to prepare a subcritical water-treated pulverized mixture (subcritical water treatment step); Step 3: A step of cooling the subcritical water-treated pulverized mixture prepared in step 2 to prepare a carotene-containing composition having spherical particles with a median diameter (D 50 ) of 0.15 to 0.55 ⁇ m (cooling step). By the cooling step of step 3, a carotene-containing composition in which spherical particles of fat-soluble carotene are dispersed in water is prepared.
  • the carotene-containing composition prepared in step 3 can be further subjected to the following step 4, if necessary.
  • step 4 a dried, solid carotene-containing composition can be prepared.
  • Step 4 A step of subjecting the carotene-containing composition prepared in step 3 to a drying treatment to prepare a solid carotene-containing composition. Therefore, the method for producing the carotene-containing composition is characterized by having the above steps 1 to 3 or steps 1 to 4.
  • the carotene crystals used as a raw material are solid carotenes, primarily composed of ⁇ -carotene. However, as described above, ⁇ -carotene, ⁇ -carotene, and/or lycopene may be contained in addition to ⁇ -carotene, as long as the effects of the present invention are not impaired.
  • the ⁇ -carotene is preferably all-trans- ⁇ -carotene, but may also contain other stereoisomers (9-cis ⁇ -carotene, 13-cis ⁇ -carotene, 15-cis ⁇ -carotene, 9,13-disis- ⁇ -carotene, 9,13'-disis- ⁇ -carotene, etc.).
  • the ⁇ -carotene other than all-trans- ⁇ -carotene is preferably 9-cis ⁇ -carotene and 13-cis ⁇ -carotene.
  • the proportion of all-trans- ⁇ -carotene, when the total amount of all-trans- ⁇ -carotene, 9-cis ⁇ -carotene, and 13-cis ⁇ -carotene is taken as 100% by mass can be 50% by mass or more, preferably 75% by mass or more but less than 100% by mass, and more preferably 75% by mass or more but less than 99% by mass.
  • the raw material carotene crystals can be produced by known methods such as chemical synthesis, fermentation, and extraction from plants or algae.
  • the chemical synthesis method involves combining two molecules of ⁇ -ionone and ⁇ - C14 , C16 , C19 aldehyde via a Grignard reaction to form ⁇ - C40 -diol, which is then dehydrated and hydrogenated to produce ⁇ -carotene.
  • ⁇ -carotene with a content of 96% or more produced by chemical synthesis is approved for use as a designated additive in pharmaceuticals, quasi-drugs, and food and beverages.
  • carotene crystals are commercially available. Preferably, they have a high beta-carotene content of 96% by mass or more, and carotene prepared by chemical synthesis or fermentation can be suitably used.
  • Gum ghatti is a water-soluble polysaccharide prepared by drying and solidifying sap secreted from cracks in the trunk of Anogeissus latifolia Wall. (Combretaceae). This water-soluble polysaccharide is composed of arabinose, galactose, mannose, xylose, and glucuronic acid, and contains approximately 3% by mass of protein, forming a polysaccharide-protein complex.
  • the weight-average molecular weight of this gum ghatti is typically within the range of 0.6 x 10 to 2 x 10 , preferably 0.8 x 10 to 2 x 10 , and more preferably 0.8 x 10 to 1.2 x 10 .
  • Such gum ghatti is commercially available, and examples of commercially available gum ghatti products include "Gutti Gum SD" manufactured by San-Ei Gen F.F.I. Co., Ltd.
  • Low-molecular-weight gum ghatti is gum ghatti obtained by subjecting the aforementioned gum ghatti to low molecular weight treatment such as thermal decomposition, acid decomposition, and/or enzymatic decomposition.
  • the weight-average molecular weight of low-molecular-weight gum ghatti is not limited, but may be, for example, 0.020 x 10 to less than 0.60 x 10. It is preferably 0.025 x 10 to 0.50 x 10 , more preferably 0.030 x 10 to 0.40 x 10 , even more preferably 0.030 x 10 to 0.35 x 10 , and still more preferably 0.040 x 10 to 0.35 x 10 .
  • Low molecular weight gum ghatti can be prepared using the above-mentioned gum ghatti as a raw material, for example, according to the methods described in Japanese Patent No. 7358063 (Patent Document 8), Japanese Patent No. 7128461 (Patent Document 9), or Japanese Patent No. 7080818 (Patent Document 10), without being limited thereto.
  • the molecular weight and molecular weight distribution of gum ghatti and low-molecular-weight gum ghatti are measured by the following method. [Method for measuring molecular weight and molecular weight distribution] The molecular weight and molecular weight distribution are measured by GPC analysis under the following conditions. Detector: RI Mobile phase: 100mM K2SO4 Flow rate: 1.0ml/min Temperature: 40°C Column: TSKgel GMPWXL 30 cm (Guard PWXL) Injection: 100 ⁇ l Pullulan standard: Shodex STANDARD P-82.
  • Gum arabic is a polysaccharide obtained from the sap of Acacia plants (e.g., Acacia senegal, Acacia seyal, etc.), which are legumes. Although the molecular structure of gum arabic has not been fully elucidated, it is known that its constituent sugars are galactose, arabinose, rhamnose, and glucuronic acid. Gum arabic is commercially available, and examples of such products include "Gum Arabic SD" manufactured by San-Ei Gen F.F.I. Co., Ltd.
  • modified gum arabic obtained by modifying the gum arabic can also be used.
  • Modified gum arabic has a higher weight-average molecular weight and arabinogalactan protein content than regular gum arabic, and is therefore superior in emulsifying properties, and is gum arabic having a weight-average molecular weight of 1.5 million or more or an arabinogalactan protein content of 17% by weight or more.
  • the weight-average molecular weight and arabinogalactan protein content of gum arabic can be determined by gel permeation chromatography (GPC-MALLS) using a multi-angle light scattering (MALLS) photometer and an RI (refractive index) detector connected online.
  • Modified gum arabic is commercially available, and examples of such products include "SUPER GUM (trademark)" manufactured by San-Ei Gen F.F.I. Co., Ltd.
  • modified starches such as Ingredion's "Purity Gum BE.”
  • the grinding treatment can be carried out by wet-grinding the raw material carotene crystals in the presence of the above-mentioned emulsifier and water using a grinding method known per se, for example, a grinding device such as a ball mill or a bead mill, until the median diameter (D 50 ) is 0.55 ⁇ m or less.
  • the temperature condition during wet-grinding may be any temperature that allows the raw material carotene crystals to be ground in a solid state without melting, and is usually set and adjusted in the range of 0 to 80°C, preferably 5 to 60°C, more preferably 15 to 40°C.
  • the median diameter of the crushed carotene crystals is not limited as long as it is 0.55 ⁇ m or less, but is preferably 0.15 to 0.5 ⁇ m, more preferably 0.2 to 0.4 ⁇ m, and even more preferably 0.2 to 0.3 ⁇ m.
  • the ratio of water to 1 part by mass of raw carotene crystals is not limited, but can typically be set in the range of 1 to 10,000 parts by mass. It is preferably in the range of 10 to 1,000 parts by mass, more preferably 15 to 1,000 parts by mass, and particularly preferably 15 to 500 parts by mass. If the water ratio is lower than the above-mentioned normal ratio, the viscosity of the milled mixture will increase significantly, which may significantly reduce handling in the milling, subcritical water treatment, and/or cooling processes, and may cause problems such as scorching or pipe blockage during subcritical water treatment.
  • the carotene concentration in the carotene-containing composition obtained by production will be too low, resulting in problems such as requiring a larger amount to be used or requiring concentration when used, which is undesirable.
  • the ratio of emulsifier to 100 parts by mass of raw carotene crystals is not limited, but can typically be set in the range of 1 to 100,000 parts by mass. It is preferably 50 to 10,000 parts by mass, more preferably 50 to 5,000 parts by mass, and especially preferably 50 to 3,000 parts by mass. If the ratio of emulsifier is lower than the above-mentioned normal ratio, it may not be possible to impart dispersion stability to the ground carotene particles, and problems such as aggregation and precipitation may occur.
  • the ratio of emulsifier is higher than the above-mentioned normal ratio, the viscosity of the ground mixture will increase significantly, significantly reducing handling in the grinding, subcritical water treatment, and/or cooling processes, and causing problems such as burning and pipe clogging during subcritical water treatment, which is undesirable.
  • the emulsifier can typically be used in a state dissolved in water to achieve the above-mentioned ratio.
  • the grinding process can also be carried out in the presence of stabilizing ingredients, such as antioxidants and preservatives, in addition to the water and emulsifiers, as long as the effects of the present invention are not impaired.
  • stabilizing ingredients such as antioxidants and preservatives, in addition to the water and emulsifiers, as long as the effects of the present invention are not impaired.
  • ingredients with antioxidant properties include antioxidants that can be incorporated into foods and beverages, such as vitamin E (tocopherol, tocotrienol), butylated hydroxytoluene, butylated hydroxyanisole, vitamin C and its derivatives (ascorbic acid, ascorbate, ascorbyl palmitate), BHT, BHA, enzyme-modified isoquercitrin, bayberry extract, and sunflower seed extract.
  • ingredients with preservative properties include preservatives that can be incorporated into foods and beverages, such as propylene glycol, glycerin, ethanol, benzoic acid, benzoates, parahydroxybenzoic acid esters, sorbic acid, and sorbates.
  • the pH of the composition to be subjected to the grinding process is not limited, but is in the range of pH 2 to 6, preferably pH 3 to 5.
  • the raw material carotene crystals can be blended with water, an emulsifier, and an edible organic acid such as citric acid, malic acid, tartaric acid, acetic acid, lactic acid, phosphoric acid, ascorbic acid, or phytic acid.
  • the prepared slurry-like ground mixture can be subjected to a homogenization process, if necessary.
  • a homogenization process By performing the homogenization process, the carotene crystal powder that has aggregated in the ground mixture can be uniformly dispersed.
  • the homogenization process can be carried out by a method known per se, for example, using a high-pressure homogenizer.
  • Step 2 is a step (subcritical water treatment step) in which the slurry-like ground mixture containing the carotene crystals (ground product) prepared in Step 1, water, and an emulsifier is subjected to subcritical water treatment to prepare a subcritical water-treated product.
  • a new emulsifier may be added to the pulverized mixture obtained in step 1. Since emulsifiers other than gum ghatti have low heat resistance, it is preferable to add gum ghatti newly during the subcritical water treatment, particularly when an emulsifier other than gum ghatti is used in step 1. Even when gum ghatti is used in step 1, gum ghatti may be added in step 2, if necessary.
  • the amount of gum ghatti added can be appropriately selected from the range of 0.1 to 5,000 parts by mass relative to 100 parts by mass of carotene in the ground mixture, or can be selected from the range of 0.1 to 50% by mass in terms of concentration in 100% by mass of the ground mixture.
  • subcritical water treatment refers to a process in which the slurry-like ground mixture prepared in step 1 is heated at a high temperature of 100°C or higher but lower than the critical temperature of water, and at a high pressure equal to or higher than the saturated water vapor pressure.
  • the subcritical water treatment can be carried out by placing the slurry-like pulverized mixture to be treated in a heat-resistant and pressure-resistant container made of metal, ceramics, or the like, sealing the container, and heating and pressurizing the pulverized mixture so that the water in the pulverized mixture becomes subcritical.
  • the subcritical water treatment can be carried out using various commercially available heat sterilization devices.
  • the pressure used in subcritical water treatment is not particularly limited, as long as it is equal to or greater than the saturated vapor pressure at each temperature used in the subcritical water treatment.
  • the pressure can be set in the range of 0.1 MPa to 30 MPa.
  • a range of 0.2 MPa to 20 MPa is preferred, a range of 0.3 MPa to 15 MPa is more preferred, a range of 0.5 MPa to 10 MPa is particularly preferred, and a range of 1.0 MPa to 5.0 MPa is even more preferred.
  • Subcritical water treatment pressures significantly below 0.1 MPa tend to cause the water to boil and not be heated sufficiently, which is undesirable.
  • increasing the pressure in subcritical water treatment to significantly above 30 MPa requires the equipment used to have a high level of pressure resistance, which incurs excessive costs and is undesirable.
  • the subcritical water treatment time varies depending on the amount of ground mixture being treated, the temperature, and the pressure conditions, but is generally preferably between 0.1 and 60 seconds (the holding time after the temperature and pressure for subcritical water treatment are reached). It is preferably 0.1 to 40 seconds, and more preferably 1 to 40 seconds. If the treatment time is shorter than 0.1 seconds, sufficient color change will not occur, while if the treatment time is longer than 60 seconds, carotene and gum ghatti may be decomposed.
  • suitable subcritical water treatment conditions for the pulverized mixture can be, for example, a temperature of 158 to 180°C, a pressure of 0.1 to 5.0 MPa (but not less than the saturated vapor pressure at the temperature where the subcritical water treatment is performed), and a treatment time of 0.1 to 60 seconds.
  • Step 3 Cooling Step 3 is a step in which the subcritical water treated product prepared in step 2 is cooled to prepare a carotene-containing composition having spherical particles with a median diameter (D 50 ) of 0.15 to 0.55 ⁇ m.
  • the median diameter (D 50 ) of the carotene microparticles (spherical particles) prepared by such a cooling treatment is 0.15 to 0.55 ⁇ m, as described above. Although there are no particular limitations within this range, it is preferably 0.15 to 0.4 ⁇ m, and more preferably 0.2 to 0.3 ⁇ m.
  • the definition, measurement method, and method for confirming that the particles are spherical are as described above.
  • the cooling process can be carried out using, but is not limited to, a double-pipe heat exchanger, a multi-pipe heat exchanger, a plate-type heat exchanger, a coil-type heat exchanger, etc.
  • the carotene-containing composition thus prepared can be used as is in the form of a carotene-water dispersion or emulsion, but if necessary, it may also be prepared as a semi-solid or solid formulation by concentrating or drying it.
  • Step 4 Drying Step Step 4 is a step in which the carotene-containing composition prepared in step 3 is subjected to a drying treatment to prepare a solid carotene-containing composition.
  • the drying treatment can be carried out by a method known per se, such as forced air drying, spray drying, freeze drying, vacuum drying, or fluidized bed drying, as long as the effect of the present invention is not impaired.
  • antioxidants such as vitamin E (tocopherol, tocotrienol), butylated hydroxytoluene, butylated hydroxyanisole, vitamin C and its derivatives (ascorbic acid, ascorbate, ascorbyl palmitate), BHT, BHA, or enzyme-modified isoquercitrin, bayberry extract, sunflower seed extract, and stabilizers such as cyclodextrin may also be added to the carotene-containing composition.
  • the solid carotene-containing composition thus prepared can be further formulated into a desired dosage form (e.g., powder, granules, tablets, etc.). Although not limited thereto, a formulation in powder form (powder formulation) is preferred.
  • Fats and oils also include solid fats (e.g., meat fat and lard) and oils that are liquid at room temperature (e.g., vegetable oils such as sesame oil, corn oil, cottonseed oil, soybean oil, and peanut oil). Fats and oils also include esters of medium-chain vegetable fatty acids.
  • the carotene-containing composition thus prepared has the composition and properties described in (I).
  • this carotene-containing composition contains 0.01 to 10% by mass of beta-carotene.
  • the beta-carotene contains at least 13-cis beta-carotene, 9-cis beta-carotene, and all-trans-beta-carotene, and is characterized in that the proportion of all-trans-beta-carotene relative to the total amount (100% by mass) of these is 50% by mass or more, preferably 75% by mass or more but less than 100% by mass, and more preferably 75% by mass or more but less than 99% by mass.
  • the carotene-containing composition is characterized in that when it is dissolved (including dispersed) in water (distilled water) to a carotene concentration of 10 ppm, its chromaticity is red to yellow (neutral color) specified in the L * a * b * color space color system as a hue angle ⁇ of 50° to 65°, an a * value of 20 to 40, and a b * value of 40 to 52. Also included are compositions with a lightness L * value of 70 to 85 and a chroma C value of 45 to 65, particularly 50 to 65.
  • this carotene-containing composition is characterized by excellent emulsion stability, turbidity, acid resistance, salt resistance, shaking resistance, UHT sterilization resistance, and/or light resistance.
  • emulsion stability, turbidity, acid resistance, salt resistance, shaking resistance, UHT sterilization resistance, and/or light resistance are explained in the experimental examples described below, and these descriptions can be used as a reference.
  • This carotene-containing composition can be used as an ingredient in foods and beverages, cosmetics, pharmaceuticals, or quasi-drugs.
  • this carotene-containing composition has a neutral color between red and yellow, and is excellent in emulsion stability, turbidity, acid resistance, salt resistance, shaking resistance, UHT sterilization resistance, and/or light resistance, making it suitable for use as a colorant preparation (colorant, pigment) in foods and beverages, cosmetics, pharmaceuticals, or quasi-drugs.
  • compositions there are no particular restrictions on the composition to be colored (colored composition). Examples include foods and beverages, cosmetics, quasi-drugs, and pharmaceuticals. Acidic foods and beverages with a pH of 4.5 or less, and edible compositions used in the production of such foods and beverages, are preferred.
  • the present carotene-containing composition particularly the carotene-containing composition prepared using an emulsifier other than modified starch, significantly suppresses carotene aggregation or precipitation and adhesion to plastic containers such as PET, even in foods and beverages with a pH of 3.5 or less, allowing the target foods and beverages to be stably colored to the desired color tone.
  • HPLC device Nippon Bunkosha LC-2000 Plus Stationary phase: L-Colomn ODS (4.6 ⁇ 250 mm, 5 ⁇ m)
  • Flow rate 1mL/min
  • test solution final carotene concentration: 10 ppm
  • citric acid anhydrous
  • Test carotene-containing composition to be tested was adjusted with ion-exchanged water to a final carotene concentration of 10 ppm, and salt was added to the composition to a final concentration of 10% by mass to prepare a test solution for evaluating salt tolerance. This was heated at 95°C for 5 minutes, and the appearance of the test solution was visually observed to evaluate changes before and after heating.
  • a test solution final carotene concentration: 10 ppm (blank) prepared in the same manner but without adding salt was also heated under the same conditions, and changes before and after heating were evaluated.
  • Simulated Seasoning Liquid Test A simulated seasoning liquid (test liquid) (pH 2.5) was prepared containing 0.1% by mass of citric acid (anhydrous), 10% by mass of salt, 5% by mass of ethanol, a carotene-containing composition (adjusted to a final concentration of 10 ppm), and the remainder being ion-exchanged water. After heating this at 95°C for 5 minutes, the appearance of the test liquid was visually observed and the changes before and after heating were evaluated.
  • test liquid consisting of a carotene-containing composition (adjusted to a final concentration of 10 ppm) and the remainder being ion-exchanged water was prepared and heated under the same conditions, and the changes before and after heating were evaluated.
  • a carotene-containing composition with an absorbance (720 nmAbs) of more than 0.15 can be judged to have carotene particles uniformly dispersed in water, good emulsion stability, and stable color tone. Furthermore, as mentioned above, turbidity enhances the color development and coloring effects, improving the visual appeal of the final product. Therefore, a carotene-containing composition with an absorbance (720 nmAbs) of more than 0.15 has a high coloring effect and is useful as a pigment preparation.
  • step 4 Drying treatment (step 4) Of the prepared carotene-containing compositions, the carotene-containing composition of Example 2 was dried by spray drying (inlet 165°C, outlet 95°C) using a spray dryer L-8i (manufactured by Okawara Kakoki Co., Ltd.) to prepare a carotene-containing composition in a dry powder state (Example 2D). For comparison, the pulverized mixture 2 before the critical water treatment in Example 2 was also dried under the same spray drying conditions as above to prepare a dried product of pulverized mixture 2 (pulverized mixture 2D) (see Table 4).
  • the pulverized mixture 2 before critical water treatment i.e., pulverized mixture 2 itself
  • the carotene-containing composition after critical water treatment Example 2
  • JEM-3100FEF transmission electron microscope
  • raw carotene is wet-ground in the presence of an emulsifier (gum ghatti), and then subjected to subcritical water treatment in the presence of the emulsifier (gum ghatti) under pressure at a high temperature of 160°C or higher for a short period of time (within 60 seconds), followed by cooling.
  • an emulsifier gum ghatti
  • subcritical water treatment in the presence of the emulsifier (gum ghatti) under pressure at a high temperature of 160°C or higher for a short period of time (within 60 seconds), followed by cooling.
  • Example 2D Example 2D
  • Example 2D the dried product of Example 2 (Example 2D) was used to carry out the acid resistance evaluation test, salt tolerance evaluation test, and simulated seasoning liquid test described above.
  • the results are shown in Table 6.
  • the carotene-containing composition of the present invention exhibited good stability under acidic conditions, in the presence of salt, and in a simulated seasoning liquid.
  • the carotene-containing compositions (Examples 3-1 and 3-2) were confirmed to be stable, as they maintained almost the same particle size (D 50 ), proportion of coarse particles, color, and carotene content as before storage even after long-term storage.
  • raw carotene is wet-ground in the presence of an emulsifier (gum ghatti), and then subjected to subcritical water treatment in the presence of the emulsifier (gum ghatti) under pressure at a high temperature of 200°C or higher for a short period of time (within 10 seconds), followed by cooling.
  • an emulsifier gum ghatti
  • subcritical water treatment in the presence of the emulsifier (gum ghatti) under pressure at a high temperature of 200°C or higher for a short period of time (within 10 seconds), followed by cooling.
  • the carotene-containing compositions (Examples 5-1 to 5-4, Examples 6-1 and 6-2) were confirmed to be stable, as they maintained almost the same particle size (D 50 ), proportion of coarse particles, color, and carotene content as before storage even after long-term storage.
  • Example 4 Preparation of beverages and evaluation of beverages
  • a model beverage (pH 3) was prepared using the dried product of Example 2 (Example 2D), and a storage stability evaluation test, a UHT sterilization resistance test, a shaking resistance test, and a light resistance test were carried out.
  • Model Beverage A beverage (pH 3) consisting of 13.3% by mass of high fructose glucose syrup, 0.3% by mass of citric acid (anhydrous), 0.05% by mass of trisodium citrate, 0.04% by mass of L-ascorbic acid, a carotene-containing composition (Example 2D) (adjusted to a final concentration of 10 ppm), and the remainder being ion-exchanged water was hot-packed into a 500 mL PET bottle at 93°C, and the resulting beverage was used as a model beverage to carry out the following tests.
  • pH 3 consisting of 13.3% by mass of high fructose glucose syrup, 0.3% by mass of citric acid (anhydrous), 0.05% by mass of trisodium citrate, 0.04% by mass of L-ascorbic acid, a carotene-containing composition (Example 2D) (adjusted to a final concentration of 10 ppm), and the remainder being ion-exchanged
  • the median diameter ( D50 ) of the solid carotene (carotene crystals) contained in ground mixtures 7 and 8 and the proportion of coarse particles (particles larger than 1.3 ⁇ m) were adjusted by changing the grinding time so that they were in the range of 0.15 to 55 ⁇ m and 17% or less, respectively.
  • raw carotene is ground in the presence of an emulsifier (gum ghatti), and then subjected to subcritical water treatment in the presence of the emulsifier (gum ghatti) under pressure at a high temperature of 160°C or higher for a short period of time (within 60 seconds), followed by cooling.
  • an emulsifier gum ghatti
  • subcritical water treatment in the presence of the emulsifier (gum ghatti) under pressure at a high temperature of 160°C or higher for a short period of time (within 60 seconds), followed by cooling.
  • a carotene-containing composition having spherical carotene particles with a median diameter of 0.15 to 0.55 ⁇ m, with a proportion of coarse particles with a particle diameter of more than 1.3 ⁇ m of 17% or less; and a water - diluted solution of the carotene-containing composition (carotene concentration 10 ppm) has a hue angle ⁇ of 50° to 65 ° , an a * value of 20 to 40, and a b * value of 40 to 52 in the L *a* b* color space color system, and exhibits the desired color (an intermediate color between red and yellow).
  • the median diameter ( D50 ) of the solid carotene (carotene crystals) contained in ground mixtures 9 and 10 and the proportion of coarse particles (particles larger than 1.3 ⁇ m) were adjusted by changing the grinding time to fall within the range of 0.15 to 0.55 ⁇ m and 17% or less, respectively (see Table 24).
  • raw carotene is ground in the presence of an emulsifier (gum ghatti), and then subjected to subcritical water treatment in the presence of the emulsifier (gum ghatti) under pressure at a high temperature of 158°C or higher for a short period of time (within 60 seconds), followed by cooling.
  • an emulsifier gum ghatti
  • subcritical water treatment in the presence of the emulsifier (gum ghatti) under pressure at a high temperature of 158°C or higher for a short period of time (within 60 seconds), followed by cooling.
  • a carotene-containing composition having spherical carotene particles with a median diameter of 0.15 to 0.55 ⁇ m and containing 17% or less coarse particles with a particle diameter of more than 1.3 ⁇ m; the composition has excellent turbidity; and a water - diluted solution of the carotene-containing composition (carotene concentration 10 ppm) has a hue angle ⁇ of 50° to 65°, an a * value of 20 to 40, and a b * value of 40 to 52 in the L *a* b * color space color system, exhibiting the desired color (an intermediate color between red and yellow).
  • Experimental Example 7 Preparation of the carotene-containing composition and evaluation of its color (part 6) (1) Production of the Carotene-Containing Composition (a) Preparation of a Ground Mixture of Carotene Crystals (Step 1) Mixtures prepared by mixing the raw materials listed in Table 26 were finely ground and then homogenized (500 kg/ cm2 x 5 times) in the same manner as in Experimental Example 1(1)(a) to prepare slurry-like ground mixtures (ground mixtures 11 to 15).
  • the median diameter ( D50 ) of the solid carotene (carotene crystals) contained in ground mixtures 11 to 13 and the proportion of coarse particles (particles larger than 1.3 ⁇ m) were adjusted by changing the grinding time to fall within the range of 0.15 to 55 ⁇ m and 17% or less, respectively.
  • Step 2 Subcritical water treatment (step 2) and cooling treatment (step 3)
  • the slurry-like pulverized mixtures 11 to 13 prepared above were mixed with the components listed in Table 27 to prepare compositions, which were then subjected to subcritical treatment in a nanoemulsion production apparatus in which the temperature and pressure conditions were set to produce a subcritical water state (see Table 28) (Step 2).
  • the prepared subcritical water treatment product was cooled to room temperature in a cooling device continuously attached to the above-mentioned device (Step 3), and various carotene-containing compositions in an emulsion state (Examples 11-1 to 11-2, Examples 12-1 to 12-2, and Examples 13-1 to 13-2) were collected.
  • the carotene-containing composition was confirmed to be stable, as it maintained the particle size (D 50 ), proportion of coarse particles, color, and carotene content before storage even after long-term storage.
  • Model beverages (pH 3) were prepared using the carotene-containing compositions in a dry powder state (Examples 9-2D, 10-2D, 11-1D, 11-2D, 14-1D, 14-2D, and 15-1D) in the same manner as in Experimental Example 4.
  • the carotene concentration in the beverage was adjusted to 10 ppm.

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Abstract

La présente invention concerne : une composition contenant du carotène ayant une couleur intermédiaire entre le rouge et le jaune ; et un procédé de production de la composition contenant du carotène. Une composition contenant du carotène selon la présente invention présente les propriétés caractéristiques suivantes.　Le diamètre médian (D50) des particules de carotène est de 0,15 µm à 0,55 µm bornes comprises ; la proportion de particules de carotène ayant chacune un diamètre de particule supérieur à 1,3 µm est de 17% ou moins pour 100% du volume total de toutes les particules de carotène ; et la teinte de couleur d'une solution aqueuse de la composition contenant du carotène, qui est ajustée de façon à avoir une concentration de carotène de 10 ppm, a un angle de teinte de couleur θ de 50° à 65°, une valeur * de 20 à 40, et une valeur b* de 40 à 52 dans un système d'espace colorimétrique L*a*b*.
PCT/JP2025/013005 2024-03-29 2025-03-28 Composition contenant du carotène et son procédé de production Pending WO2025206390A1 (fr)

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS57195161A (en) * 1981-05-15 1982-11-30 Basf Ag Manufacture of finely powdery cartinoid preparation or retinoid preparation
JPH0366615A (ja) * 1989-07-25 1991-03-22 F Hoffmann La Roche Ag コロイド分散カロチノイド調剤の新規製造方法
JP2001226262A (ja) * 1996-10-14 2001-08-21 F Hoffmann La Roche Ag 微粉状調製物の調製方法
WO2007046333A1 (fr) * 2005-10-19 2007-04-26 San-Ei Gen F.F.I., Inc. Agent emulsifiant et composition emulsifiee preparee avec ledit agent
WO2019208539A1 (fr) * 2018-04-23 2019-10-31 三栄源エフ・エフ・アイ株式会社 Composition d'émulsion

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS57195161A (en) * 1981-05-15 1982-11-30 Basf Ag Manufacture of finely powdery cartinoid preparation or retinoid preparation
JPH0366615A (ja) * 1989-07-25 1991-03-22 F Hoffmann La Roche Ag コロイド分散カロチノイド調剤の新規製造方法
JP2001226262A (ja) * 1996-10-14 2001-08-21 F Hoffmann La Roche Ag 微粉状調製物の調製方法
WO2007046333A1 (fr) * 2005-10-19 2007-04-26 San-Ei Gen F.F.I., Inc. Agent emulsifiant et composition emulsifiee preparee avec ledit agent
WO2019208539A1 (fr) * 2018-04-23 2019-10-31 三栄源エフ・エフ・アイ株式会社 Composition d'émulsion

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