WO2006082922A1 - Colorant bleu gardenia a ton ameliore et procede de fabrication associe - Google Patents

Colorant bleu gardenia a ton ameliore et procede de fabrication associe Download PDF

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Publication number
WO2006082922A1
WO2006082922A1 PCT/JP2006/301861 JP2006301861W WO2006082922A1 WO 2006082922 A1 WO2006082922 A1 WO 2006082922A1 JP 2006301861 W JP2006301861 W JP 2006301861W WO 2006082922 A1 WO2006082922 A1 WO 2006082922A1
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Prior art keywords
value
blue pigment
gardenia blue
gardenia
degradation product
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PCT/JP2006/301861
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English (en)
Japanese (ja)
Inventor
Koichi Nakashima
Hiromitsu Aoki
Kuniyuki Shinbo
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San-Ei Gen F.F.I., Inc.
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Application filed by San-Ei Gen F.F.I., Inc. filed Critical San-Ei Gen F.F.I., Inc.
Priority to JP2007501643A priority Critical patent/JP4637896B2/ja
Publication of WO2006082922A1 publication Critical patent/WO2006082922A1/fr

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    • 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

Definitions

  • the present invention relates to a gardenia blue pigment having a light blue color with a red to purple color reduction or a bright blue color tone with respect to a conventional gardenia blue pigment and a pigment preparation thereof. Furthermore, the present invention relates to a method for producing a gardenia blue pigment.
  • gardenia blue pigments are widely used as blue coloring agents for food pigments.
  • Such gardenia blue pigment is generally an amino acid containing a primary amino group in an iridoid glycoside obtained by extraction from the fruit of Gardenia augusta MERRILL var. Grandiflora HORT., Gardenia jasminoides ELLIS. It is prepared by allowing ⁇ -dalcosidase to act in the presence of protein degradation products and the like, and separating the blue pigment fraction from the obtained product (Patent Documents 1 and 2).
  • the gardenia blue pigment obtained by such a method has a reddish to purple-colored blue (also referred to as “red to purple” in the present specification). Furthermore, it is known that the conventional gardenia blue pigment changes its color to a color with a further increase in red-purple color with time.
  • the iridoid glycoside contains a primary amino group
  • polyphenol is coexisting or produced.
  • a method of adding polyphenol to the gardenia blue pigment obtained later is known (see Patent Documents 3 and 4). However, these methods require polyphenols to obtain the desired gardenia blue pigment, and there is a simpler method. It has been demanded.
  • Patent Document 1 JP-A 52-53934
  • Patent Document 2 JP-A-56-92792
  • Patent Document 3 WO 03/029358 A1
  • Patent Document 4 Japanese Patent Laid-Open No. 7-111896
  • the color tone of the blue pear blue pigment that meets the needs of the industry described above is changed from the conventional red to purple-tinged blue power. Red to purple-colored bright blue or greenish bright blue. It aims to improve. That is, the present invention provides a gardenia blue pigment having a bright or blue color having a red to purple color less than that of a conventional gardenia blue pigment, or having a bright or blue color, and a pigment preparation thereof. Objective. Another object of the present invention is to provide a method for producing a gardenia blue pigment having an improved color tone. Means for solving the problem
  • the present invention has the following aspects:
  • Item 1 Gardenia blue pigment prepared by treating / 3 darcosidase with an iridoid glycoside derived from the fruit of Arachnaceae gardenia in the presence of a casein degradation product treated with a proline-specific endoprotease.
  • Item 2 The product according to Item 1, wherein the casein degradation product is an oligopeptide having 2 to: LO amino acid residues. Chinese pear blue pigment.
  • Item 3 The gardenia blue pigment according to Item 1, wherein the casein degradation product contains oligopeptides having a molecular weight of 200 to 3000 in a proportion of 50% by weight or more.
  • Item 2 The gardenia blue pigment according to Item 1, which has a negative color tone.
  • Item 6 A blue pigment preparation containing the gardenia blue pigment according to Item 1 or 5.
  • Item 7 A coloring composition containing the gardenia blue pigment described in Item 1 or 5.
  • Item 8 The colored composition according to claim 7, which is a food, cosmetic, pharmaceutical product, quasi-drug, or feed.
  • Item 9 A method for producing a gardenia blue pigment comprising a step of treating an iridoid glycoside derived from a fruit of a succulent family gardenia by / 3 darcosidase in the presence of a casein degradation product treated with a proline-specific endoprotease.
  • Item 10 The method for producing a gardenia blue pigment according to Item 9, wherein the casein degradation product is an oligopeptide having 2 to 2 amino acid residues: LO.
  • Item 11 casein decomposition product, the production method of claim 9, wherein the oligopeptide having a molecular weight of 200 to 3000 in a total amount is intended to include a proportion of 50 weight 0/0 above.
  • Item 10 The production method according to Item 9, which is a method for obtaining a gardenia blue pigment having a negative color tone.
  • Item 14 The use according to Item 13, wherein the casein degradation product is an oligopeptide having a number of amino acid residues of 2 to LO.
  • Claim 15 casein decomposition product, the use of claim 13, wherein the oligopeptide having a molecular weight of 200 to 3000 in a total amount is intended to include a proportion of 50 weight 0/0 above.
  • Item 14 The use according to Item 13, wherein the pigment is a gardenia blue pigment having a color tone in which the a value is more negative than 7 and the b value is more negative than 19.
  • the gardenia blue pigment to which the present invention is intended to improve the color tone is an iridoid glycoside derived from the fruit of Gamenia augusta MERRILL var. Granaifiora HORT., Gamenia jasmi noides ELLIS. Can be obtained by treating with j8-darcosidase in the presence of a protein degradation product containing a primary amino group, and separating the blue pigment fraction from the resulting reaction product (Patent Literature). 1, 2).
  • Patent Literature 1, 2
  • the description of the said literature is used in this specification as what comprises a part of this invention.
  • Gardenia blue pigment (hereinafter referred to as “conventional gardenia blue pigment” for convenience in the present specification) obtained by the method described in the literature has a red to purpleish blue color, and further, over time. It is known that the color changes from red to purple.
  • the gardenia blue pigment of the present invention improves the color tone of such a conventional gardenia blue pigment and has a bright red / purple color! /, Has a blue color! /, Has a greenish brightness and a blue color tone. It is characterized by this.
  • the gardenia blue pigment of the present invention is obtained by simply treating an iridoid glycoside with j8-darcosidase in the presence of a casein degradation product obtained by treatment with a proline-specific endoprotease. be able to.
  • the iridoid glycoside is not particularly limited as long as it is an iridoid glycoside derived from the fruit of a succulent family gardenia! Iridoid Glycosides in the Fruits of Rubiaceae Gardenia Specific examples thereof include geposide, gardenoside, gepingentiopioside, zabiposide acid and methyl deacetylasperoside.
  • the iridoid glycoside may be a single product or a combination of two or more.
  • the iridoid glycoside may be a purified product or a crude purified product. As will be described later, crushed material, juice, extract, or iridoid composition obtained from these fruits. It may be a composition containing an iridoid glycoside, such as a sugar-containing fraction.
  • the extraction solvent is not particularly limited, but for example, water or warm water (10 to 80 ° C, preferably 20 to 50 ° C), lower alcohol (for example, alcohol having 1 to 4 carbon atoms such as methanol, ethanol, isopropanol, etc., preferably May be ethanol), acetone, or a mixed solution thereof.
  • the extraction solvent is preferably a mixed solution of water and alcohol (hydrous alcohol), particularly a mixed solution of water and ethanol (hydrous ethanol).
  • iridoid glycosides eg, geposide, gardenoside, gepingentopioside, geposide acid, methyl deacetylase perosidide, etc.
  • a powerful extract can be used as an iridoid glycoside-containing product as it is or after removing insolubles, concentrating or drying.
  • the iridoid glycoside-containing product can be used after removing insoluble components or purifying as necessary.
  • water or a hydroalcoholic extract of the Acariaceae gardenia fruit obtained by the above method is used as a synthetic adsorbent resin having a porous polymer structure with an intermediate polarity (for example, a methacrylate ester).
  • an intermediate polarity for example, a methacrylate ester.
  • Polymer Diaion HP-2MG: manufactured by Mitsubishi Kaisei Co., Ltd.
  • polymer of acrylic ester Amberlite XAD-7, XAD-8: manufactured by Rohm and Nose etc.
  • a method of separating crocin (yellow pigment) and iridoid glycosides contained in the extract using the alcohol concentration difference of the eluent can also be used (see, for example, JP-A-57-151657). .
  • the degradation product of casein used in the present invention is obtained by purifying casein, which is a protein derived from milk. It is a proteolysate obtained by treatment with a specific endoprotease.
  • casein-derived protein was decomposed by treatment with a proline-specific endoprotease until the number of amino acid residues was 2 to 10, preferably 2 to 5, more preferably 2 to 4, particularly preferably 2 to 3.
  • An oligopeptide is preferred.
  • Such a casein degradation product is obtained by treating casein with a proline-specific endoprotease and then treating the product with a molecular weight of 100 to 10,000, preferably ⁇ is a molecular weight of 200 to 3000, and more preferably is a molecular weight of 200 to 200. : LOOO, more preferably by collecting fractions with a molecular weight of 300-600.
  • the oligopeptide having these molecular weight may include 100%, but may contain a proportion of at least 50 weight 0/0. The amount is preferably 70% by weight or more, more preferably 80% by weight or more, and still more preferably 90% by weight or more.
  • Fractions in the range of high molecular weight can be obtained according to a conventional method, and examples thereof include fractionation methods using membranes such as gel filtration chromatography and ultrafiltration membranes.
  • the casein degradation product (oligopeptide) used in the present invention is prepared by treating casein with an enzyme other than proline-specific endoprotease, or by acid hydrolysis instead of the casein. It can also be obtained by treating a casein partial degradation product (casein protein degradation product) (molecular weight 20000 or more) with a proline-specific endoprotease. Therefore, the casein degradation product used in the present invention may be an oligopeptide (molecular weight: 100 to 10,000) obtained by treating casein or its partial degradation product with a proline-specific endoprotease! it can.
  • the proline-specific endoprotease used to obtain a strong casein degradation product is an endoprotease capable of cleaving a peptide or polypeptide at the carboxy-terminal side of a proline residue, and is widely used in animals, plants and microorganisms. It is an enzyme that exists.
  • proline-specific endoproteases include prolyl oligopeptidase [EC 3.4.21.2 6], dipeptidinoleveptidase [EC 3.4.14.5], lysosome Pro-X canoleboxypeptidase [EC 3.4.16.2] Serine-enzyme-type proline-specific beptases such as prolylaminopeptidase [EC 3.4.11.5]; metalloenzyme-type proline-specific such as aminopeptidase P [EC 3.4.11.9] and prolidase [EC 3.4.13.9] Can give sex beptidase (Protein 'Nucleic Acid' Enzyme 42,2198-2204 (1997)). A serine enzyme type proline-specific 'peptidase is preferred.
  • the origin of the proline-specific endoprotease is not particularly limited.
  • the genus Aspergillus eg Aspergillus oryzae, Aspergillus niger
  • Flavobaterum eg Flavobacterium meningocepticum
  • Aeromonas Zanthomonas
  • it is a proline-specific endopeptidase derived from a microorganism belonging to the genus Batateroid, and more preferably a proline-specific endoprotease derived from a microorganism belonging to the genus Aspergillus.
  • casein in preparing the casein degradation product, casein can be treated by using a microorganism that produces the above-mentioned proline-specific endoprotease instead of proline-specific endoprotease.
  • the casein degradation product used in the present invention can be obtained by treating casein or a partial degradation product thereof under the treatment conditions such as pH and temperature according to each microorganism.
  • the ⁇ -darcosidase used in the present invention only needs to have at least ⁇ -darcosidase activity. Regardless of whether the enzyme is a purified enzyme or a crudely purified enzyme, a crude enzyme solution having ⁇ -darcosidase activity such as an almond extract can also be used.
  • Naringinase (Amano Enzym Co., Ltd., Japan); Coclase SS (Sankyo Co., Ltd., Japan); Cellulase Nagase (Nagase Seikagaku Co., Ltd., Japan); Sumitim AC, Sumiteam C (above, Shin Nippon Chemical Industry Co., Ltd., Japan); Separase GF (Goddo Seisei Co., Ltd., Japan), etc.)
  • a commercially available enzyme having 8-darcosidase activity can be used.
  • the treatment with ⁇ -darcosidase is not particularly limited as long as it is a treatment method for producing gardenia blue pigment. Specifically, there can be mentioned a method in which ⁇ -darcosidase is added to the aforementioned iridoid glycoside or a mixture thereof and a casein degradation product, followed by stirring or shaking treatment. Preferably, the treatment is carried out for 30 minutes to 24 hours under the conditions of 20 to 70 ° C. and pH 4 to 6 in the presence of iridoid glycosides or their contents, casein degradation products and j8-darcosidase. Can be illustrated.
  • the temperature condition is preferably 30 to 70 ° C, more preferably 40 to 60 ° C, and the pH condition is preferably pH 4 to 5. More preferably, the pH is 4.2 to 4.8.
  • Aerobic conditions can be set by blowing a molecular oxygen-containing gas such as air in addition to mechanical methods such as stirring and shaking.
  • the casein degradation product in which the iridoid compound or its content is preferably used in a proportion of 2 to 15% by weight in the reaction is based on 100 parts by weight of the strong iridoid compound. 10 to: LOO parts by weight, preferably 50 to 80 parts by weight. ⁇ -Dalcosidase is preferably used in the range of 1 to 10 parts by weight per 100 parts by weight of the iridoid compound.
  • the gardenia blue pigment of the present invention is obtained by heating the reaction solution (gardenia blue pigment-containing solution) obtained by the above reaction to about 70 to 120 ° C to deactivate the enzyme, followed by filtration or centrifugation. It can be obtained by removing insoluble matter by separation treatment or the like.
  • the gardenia blue pigment has the form of a solution thus obtained, but has a concentrate or a powder form obtained by drying by any method (vacuum drying, freeze drying, spray drying, etc.) It can be a thing.
  • the solution obtained above can be prepared by subjecting it to a conventional purification treatment such as a resin treatment or a membrane treatment.
  • the gardenia blue pigment thus obtained can be provided as a pigment preparation as it is, or a diluent, carrier or other additive is blended as another component, and the pigment formulation in that state. Can also be provided.
  • the form of the pigment preparation is not particularly limited, and can be prepared in any form such as powder, granule, tablet, liquid, emulsion, or paste.
  • the color tone of the conventional gardenia blue pigment is red to purpleish blue, whereas the gardenia blue pigment of the present invention obtained by the above method has a maximum absorption wavelength higher than 600 nm. , Preferably around 605 nm, with Hunter Lab color system (Lab value), color value (E 10
  • the gardenia blue pigment of the present invention is brighter with less red-purple and brighter than the red-purple blue color of conventional gardenia blue pigments! It has a blue color.
  • the conventional gardenia blue pigment has a maximum absorption wavelength lower than 600 nm, preferably around 585 to 595 nm, and has a Hunter Lab color system (Lab value) and a color value (E 1
  • the a value at 0% ) 0.05 is in the range of -5 or more, and the L value is in the range of 71 or less.
  • the Hunter Lab color system is a color system that forms a color solid composed of orthogonal coordinates consisting of a and b axes indicating chromaticity and an L axis perpendicular to the coordinates.
  • a increases on the positive side it means reddish, when it increases on the negative side, greenishness increases.
  • b increases on the positive side it means yellowish, and when it increases on the negative side, it means that blueness increases.
  • red-purple taste is obtained as compared with gardenia blue pigment obtained by the conventional method described in, for example, JP-A-52-53934 and JP-A-56-92792. It is possible to provide a pigment preparation of gardenia blue pigment having an improved color tone and having a reduced bright blue or greenish bright blue color.
  • the pigment preparation of gardenia blue pigment of the present invention can be widely used as a coloring agent for foods, cosmetics, pharmaceuticals, quasi-drugs, feeds and the like according to common usage. Therefore, the present invention provides colored compositions such as foods, cosmetics, pharmaceuticals, quasi-drugs, and feeds colored using the above gardenia blue pigment or a pigment preparation thereof.
  • foods include confectionery such as frozen confectionery, fresh confectionery, Japanese confectionery, and Western confectionery: beverages such as beverages and alcoholic beverages; processed agricultural products such as dried vegetables and pickles; processed marine products: or processed meat products be able to.
  • Cosmetics include cosmetics (eye shadow, mascara, lipstick and lip balm, lotion, etc.), sarcophagus, shampoo, rinse, detergent, toothpaste and mouthwash, and pharmaceuticals include tablets (such as sugar-coated tablets) A granule, a liquid agent, a capsule etc. can be mentioned.
  • the ratio of gardenia blue pigment blended in these coloring compositions is not limited, but the absorbance of the coloring composition at the maximum absorption wavelength of gardenia blue pigment around 605 nm.
  • the ratio can be increased to 0.01 to 1.
  • casein proteolysate manufactured by Meiji Dairies Co., Ltd.
  • proline-specific endoprotease derived from Aspergillus oryzae was added at a rate of 1% of the substrate casein proteolysate and reacted at 45 ° C and pH 7 for 24 hours.
  • the resulting reaction solution was inactivated at 90 ° C for 30 minutes, then returned to room temperature, passed through a UF membrane (Daisen Membrane Systems Co., Ltd., FU Y03A1), and the eluted amino acid residues consisted of 2-5 The fraction containing the oligopeptide (fractional molecular weight 100-10000) was separated.
  • Gardenia blue pigment was prepared using the above casein degradation product, and the color value and color tone of the gardenia blue pigment obtained were examined.
  • iridoid glycosides gels obtained by separating the yellow component and the iridoid glycosides using a synthetic adsorption resin such as HP-20 (Mitsubishi Chemical Corporation).
  • -Poside) 5g, ⁇ -Dalcosidase (Oriental Yeast, 2000units) lg was added to a mixture consisting of 10g of the above casein degradation product and 80ml of water, pH 4-5, 40-60.
  • Gardenia blue pigment (in solution) was obtained by stirring with C for 24 hours (maximum absorption wavelength: 605 nm).
  • the color value (E 1 (>% )) is measured by measuring the absorbance (wavelength 580 to 620 nm) of the sample to be 0.3 to 0
  • the sample diluted with a predetermined amount of ion-exchanged water was measured by measuring the spectral transmittance using an ultraviolet-visible spectrophotometer (JASCO, V560) equipped with an integrating sphere. The results are shown in Table 1.
  • a gardenia blue pigment was prepared according to Example 1 using a commercially available protein degradation product (see Table 1), and the color value and color tone of the gardenia blue pigment obtained were examined.
  • “Powdered amino acid A-2” (manufactured by Semba Sugar Co., Ltd.) used in Comparative Example 1 is an acid degradation product of plant protein
  • “Enzap V” used in Comparative Example 2 (Dainippon Meiji Seika ( Co., Ltd.) was a protease decomposition product of wheat dartene
  • “Noy-Uto®” Fluji Oil Co., Ltd.) used in Comparative Example 3 was used as a protease decomposition product of soybean protein and Comparative Example 4.
  • “SK Yeast Extract HU” (manufactured by Enomoto Paper Co., Ltd.) is an acid degradation product of yeast.
  • the gardenia blue pigment using the casein degradation product of Example 1 has an L value (lightness) of 74 or more and an a value of 11
  • the b value is It was a vivid sky blue with a low value of 22 or less.
  • a protein degradation product a plant protein acid degradation product ("powdered amino acid A-2"), a wheat dartene protease degradation product (“Enzap V "), or a yeast acid degradation product (“SK yeast extract HU”)
  • SK yeast extract HU a yeast acid degradation product
  • Gardenia blue pigments prepared using have a dark red hue, as the L value (brightness) is 70 or less and darkens because the a value is positive (plus).
  • gardenia blue pigment prepared using a protease degradation product of soybean protein (“Noyute-Uto R”) as a protein degradation product has an L value (lightness) of 71 or more and a value of negative (minus). However, it had a dark reddish color (Comparative Example 3). Also, regarding the maximum absorption wavelength, gardenia blue dye using the casein degradation product of Example 1 (average number of amino acid residues 2 to 5) is less than 600 nm compared to any of Comparative Examples 1 to 4. In order to support the shift to the higher wavelength side, it was a reddish, greenish and fresh blue.
  • the casein protein degradation product (Meiji Dairy CPP-III, manufactured by Meiji Dairy Co., Ltd.) used for the preparation was used in the same manner as in Example 1 to remove the gardenia blue pigment. As a result of preparation, although some blue pigments were produced, they were gelled and no practical dye was obtained.
  • the present invention it is possible to provide a gardenia blue pigment having a red-purple lightness! /, A blue or greenish brightness !, and a blue color tone, and a pigment preparation thereof.
  • the conventional gardenia blue pigment has a red-purple blue color tone
  • the gardenia blue pigment of the present invention has the above-mentioned color tone different from that of the conventional gardenia blue pigment. As a result, diversity can be imparted to the color tone of gardenia blue pigment.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)

Abstract

L’invention concerne un colorant bleu gardénia d’une couleur bleu vif ou bleu verdâtre ne présentant aucun ton allant du rougeâtre au violacé. Ce colorant bleu gardénia peut être produit grâce au procédé consistant à traiter l’iridoïde de glycoside avec la β-glucosidase en présence d’un produit de digestion protéique de façon à préparer le colorant bleu gardénia où est utilisé un produit de digestion protéique provenant d’une caséine, plus particulièrement un produit préparé en conduisant la digestion à l’aide d’une endoprotéase spécifique de la proline, et ce afin d’obtenir entre 2 et 10 résidus d’acides aminés.
PCT/JP2006/301861 2005-02-03 2006-02-03 Colorant bleu gardenia a ton ameliore et procede de fabrication associe WO2006082922A1 (fr)

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JP2007501643A JP4637896B2 (ja) 2005-02-03 2006-02-03 色調が改善されたクチナシ青色素とその製造方法

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JP2005-028282 2005-02-03

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WO2009120579A1 (fr) * 2008-03-28 2009-10-01 Wild Flavors, Inc. Procédé de couleur naturelle stable, produits et utilisation apparentés
JP2011217728A (ja) * 2010-03-25 2011-11-04 Riken Vitamin Co Ltd クチナシ赤色素およびその製造方法
CN102311980A (zh) * 2011-08-02 2012-01-11 云南瑞宝生物科技有限公司 一种制备天然栀子蓝色素的方法
JP2012067241A (ja) * 2010-09-27 2012-04-05 Riken Vitamin Co Ltd クチナシ青色素の製造方法
JP2012135222A (ja) * 2010-12-24 2012-07-19 Meiji Co Ltd ペプチド組成物、およびその製造方法
WO2012164396A2 (fr) * 2011-06-03 2012-12-06 E.P.C. (Beijing) Plant Pharmaceutical Technology Co., Ltd. Compositions de laque d'aluminium jaune
CN103060077A (zh) * 2011-10-20 2013-04-24 中国科学院兰州化学物理研究所 同步反应制备栀子油、栀子绿和栀子蓝的方法
WO2013070682A1 (fr) * 2011-11-07 2013-05-16 Wild Flavors, Inc. Matériau riche en génipine et son utilisation
CN105017806A (zh) * 2015-08-31 2015-11-04 桂林茗兴生物科技有限公司 一种从栀子中制备栀子蓝色素的方法
CN105624198A (zh) * 2016-03-10 2016-06-01 河南中大恒源生物科技股份有限公司 一种制备不同色调高纯度栀子蓝色素的工艺
CN106993687A (zh) * 2017-05-09 2017-08-01 福建岳海水产食品有限公司 一种栀子茶的制备方法
WO2018181008A1 (fr) * 2017-03-27 2018-10-04 グリコ栄養食品株式会社 Composition de coloration capillaire
WO2020213447A1 (fr) 2019-04-16 2020-10-22 グリコ栄養食品株式会社 Pigment bleu de gardénia et son procédé de production
JP2020174552A (ja) * 2019-04-16 2020-10-29 グリコ栄養食品株式会社 クチナシ青色素及びその製造方法
CN112741185A (zh) * 2020-12-25 2021-05-04 内蒙古蒙牛乳业（集团）股份有限公司 巧克力用色素组合物、蓝色巧克力、蓝色混合巧克力、冷冻饮品及制备方法
WO2022045151A1 (fr) * 2020-08-24 2022-03-03 天野エンザイム株式会社 Procédé de production d'une protéine modifiée
WO2022044291A1 (fr) 2020-08-28 2022-03-03 グリコ栄養食品株式会社 Pigment bleu et son procédé de production
EP4203708A4 (fr) * 2020-08-26 2024-10-09 Archer Daniels Midland Co Procédés de production de colorants de diverses teintes à partir de fruit de huito

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JPH07111896A (ja) * 1993-10-19 1995-05-02 Taito Kk 明色化された青色色素の製造方法
WO2003029358A1 (fr) * 2001-09-28 2003-04-10 San-Ei Gen F.F.I., Inc. Preparation de colorant bleu de jasmin du cap a ton ameliore

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JPS5253934A (en) * 1975-10-29 1977-04-30 Taito Kk Preparation of pigment composition
JPH07111896A (ja) * 1993-10-19 1995-05-02 Taito Kk 明色化された青色色素の製造方法
WO2003029358A1 (fr) * 2001-09-28 2003-04-10 San-Ei Gen F.F.I., Inc. Preparation de colorant bleu de jasmin du cap a ton ameliore

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