WO2003029358A1 - Preparation de colorant bleu de jasmin du cap a ton ameliore - Google Patents

Preparation de colorant bleu de jasmin du cap a ton ameliore Download PDF

Info

Publication number
WO2003029358A1
WO2003029358A1 PCT/JP2002/010100 JP0210100W WO03029358A1 WO 2003029358 A1 WO2003029358 A1 WO 2003029358A1 JP 0210100 W JP0210100 W JP 0210100W WO 03029358 A1 WO03029358 A1 WO 03029358A1
Authority
WO
WIPO (PCT)
Prior art keywords
gardenia
blue pigment
color tone
gardenia blue
polyphenol
Prior art date
Application number
PCT/JP2002/010100
Other languages
English (en)
Japanese (ja)
Inventor
Chiyoki Yukawa
Takahito Ichi
Kuniyuki Shinbo
Original Assignee
San-Ei Gen F.F.I., 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 F.F.I., Inc. filed Critical San-Ei Gen F.F.I., Inc.
Priority to JP2003532591A priority Critical patent/JP4374494B2/ja
Publication of WO2003029358A1 publication Critical patent/WO2003029358A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
    • C12P17/02—Oxygen as only ring hetero atoms
    • C12P17/06—Oxygen as only ring hetero atoms containing a six-membered hetero ring, e.g. fluorescein
    • 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
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P1/00—Preparation of compounds or compositions, not provided for in groups C12P3/00 - C12P39/00, by using microorganisms or enzymes

Definitions

  • the present invention relates to a pigment preparation of a gardenia blue pigment having a bright blue color with a reduced red-purple tinge or a greenish bright blue tone compared to a conventional gardenia blue pigment.
  • gardenia blue pigment has been widely used as a blue colorant for edible natural pigments.
  • Such gardenia blue pigments are generally added to iridid glycosides obtained by extracting from fruits of gardenia gardenia ((3 ⁇ 4 / '3 augus ta MERRILL var. Grandi flora HORT., Gardenia jasminoides ELL IS); It is prepared by reacting dalcosidase and a compound containing a primary amino group (for example, an amino acid or a protein degradation product) and separating a blue pigment fraction from the obtained product (Japanese Patent Application Laid-Open No.
  • the gardenia blue pigment obtained by such a method originally has a reddish to purpleish color (“red” in the present specification). It is also known that these conventional gardenia blue pigments change color over time to a color with a more reddish to purple tint over time. ing.
  • Japanese Patent Application Laid-Open No. 7-111896 discloses an iridide glycoside.
  • a process for aerobically coexisting with a primary amino group-containing compound containing at least 10% phosphorus in the presence of ⁇ -darcosidase to produce a gardenia blue pigment, in which polyphenol coexists in these raw materials There has been proposed a method in which a dye is added or a polyphenol is added to the obtained dye.
  • the primary amino group-containing compound used for producing a gardenia blue pigment having a light red color and a light blue color is limited to taurine or a compound containing 10% or more thereof. There's a problem.
  • the present invention changes the color of the gardenia blue pigment from a conventional red-purple blue to a light blue with little red-purple or a bright blue green.
  • the purpose is to improve.
  • an object of the present invention is to provide a gardenia blue pigment preparation prepared to have a bright blue color with little red to purple, or to have a greenish light blue color. Further, the present invention provides a method for producing a gardenia blue pigment preparation having a bright blue color having a reduced red to violet color compared to a conventional gardenia blue pigment, or having a bright blue color recording. With the goal.
  • the present inventors have conducted intensive studies in order to achieve the above object, and obtained a method for producing a gardenia blue pigment by allowing ⁇ -dalcosidase and a protein hydrolyzate to act on an ylidido glycoside.
  • a method for producing a gardenia blue pigment by allowing ⁇ -dalcosidase and a protein hydrolyzate to act on an ylidido glycoside.
  • the present invention is a gardenia blue pigment preparation having an improved color tone to a bright blue with little red to purple or a bright blue with a greenish color listed in 1 to 6 below.
  • Extracted iridid glycosides from the fruits of Gardenia gardenia A pigment preparation of a gardenia blue pigment having an improved color tone, which is prepared by blending polyphenol with a gardenia blue pigment prepared by treating with ⁇ -darcosidase in the presence of evening protein degradation products.
  • the 0-dalcosidase treatment is preferably performed under aerobic conditions.
  • the iridoid glycosides obtained by extracting the fruits of the gardenia pears are treated with ⁇ -Darcosidase in the presence of degraded protein and polyphenol to obtain a color tone.
  • An improved gardenia blue pigment preparation is provided.
  • the / 3—dalcosidase treatment is performed under aerobic conditions.
  • polyphenol is at least one selected from the group consisting of tannic acid, ellagic acid, catechin, gallic acid, myricitrine, enzyme-treated rutin, and enzyme-treated isoquercitrin A gardenia blue pigment preparation.
  • the gardenia blue pigment having an improved color tone according to any one of 1 to 4, wherein the protein hydrolyzate is a hydrolyzate of a plant, animal or microorganism-derived protein.
  • Gardenia blue pigment with improved color tone has a L value of 70 or more and an a value of negative value than -5 in Hanter Lab display (Lab value), any of 1 to 5 A pigment preparation of a gardenia blue pigment according to Crab.
  • a gardenia blue pigment having an improved color tone refers to an iridide glycoside obtained by extracting from the fruits of the gardenia prunus gardenia, which is obtained by subjecting the ylidoid glycoside to treatment with / 3-darcosidase in the presence of a protein digest.
  • Gardenia blue pigment whose color tone has been changed or improved from the red-purple blue color of the prepared gardenia blue pigment to the light blue or greenish blue with little red-purple color. .
  • the present invention also provides a method for producing a gardenia blue pigment having an improved color tone, having a bright blue with a little red-purple color or a bright blue with a greenish color, as described in 7 to 10 below.
  • Polyphenol is added to the gardenia blue pigment prepared by treating the iridide glycoside obtained from the fruits of the gardenia gardenia in the presence of proteolytic products with 3-dalcosidase, or Gardenia blue pigment preparation with improved color tone, comprising the step of treating iridido glycosides extracted from gardenia fruits with ⁇ -darcosidase in the presence of proteolysates and polyphenols Manufacturing method.
  • the j3-dalcosidase treatment is preferably performed under aerobic conditions.
  • the polyphenol is at least one selected from the group consisting of tannins, catechins, quercetin glycosides, gallic acid and myricitrine. Production of a gardenia blue pigment preparation having an improved color tone according to 7 above, Method. 9. The color tone as described in 7 above, wherein the polyphenol is at least one selected from the group consisting of tannic acid, ellagic acid, catechin, gallic acid, myricitrin, enzyme-treated rutin, and enzyme-treated isoquercitrin. A method for producing a pigment preparation of gardenia blue pigment.
  • Gardenia blue pigment with improved color tone has a L value of 70 or more in Hanter Lab display (b value) and a value of a value that is more negative than -5, any of 7 to 9 A method for producing a pigment preparation of a gardenia blue pigment according to the present invention.
  • the present invention provides the following from 12 to 16:
  • the polyphenol is a tannin, a catechin, a quercetin glycoside, at least one selected from the group consisting of gallic acid and myricitrin, wherein the gardenia blue pigment according to any one of the above items 12 to 14, How to improve color.
  • the gardenia blue pigment preparation of the present invention having an improved color tone can be conveniently prepared by reacting 13-darcosidase and a protein hydrolyzate with ylided glycoside to produce a gardenia blue pigment. It can be obtained by adding polyphenol to the obtained gardenia blue pigment.
  • the gardenia blue pigment targeted for the color improvement of the present invention is specifically obtained by extracting from the fruits of the gardenia japonica ( ⁇ Gardenia augus ta MERRILL var. Grandi flora HORT., Gardenia jasininoides ELL IS). Iridide distribution It can be obtained by treating a mixture of carbohydrates and degraded protein with / 3-dalcosidase and then separating the blue pigment fraction from the resulting product ( JP-A-52-53934 and JP-A-56-92792). The description of the document is incorporated herein as a part of the present invention.
  • the gardenia blue pigment obtained by such a method originally has a reddish-purple blue color.
  • the gardenia blue pigment changes its color tone to have a more reddish-purple color with time upon storage.
  • the iridide glycoside is not particularly limited as long as it is an iridide glycoside obtained by extracting from the fruits of the gardenia prunus, and those disclosed in JP-A-52-53934 may also be mentioned. it can. Specific examples include geniposide, gardenoside, genipin gentiopioside, geniposidic acid and methyl deacetylasperocidide.
  • gardenia fruits can be blanched or directly (raw) or dried, and then crushed as necessary, and then converted to water ( Immersion in 10-80 ° C, preferably 20-5 (TC), alcohol (for example, methanol, ethanol, isopropanol, preferably ethanol), acetone, or a mixed solution thereof.
  • the above-mentioned extraction solvent is preferably a mixed solution of water and alcohol (hydrous alcohol), particularly a mixed solution of water and ethanol (hydrous ethanol).
  • the extract obtained by the above-mentioned method is brought into contact with a synthetic adsorption resin, and the resin is applied to the genus Acena Of crocin and Iridido glycoside is yellow dye contained in the same in fruit adsorbed, and crocin and Iridido glycoside by concentration difference of solvents may also be used a method of eluting separated.
  • the protein hydrolyzate examples include a protein derived from a plant such as soybean or wheat, a protein derived from an animal such as casein or gelatin, or a hydrolyzate of a protein derived from a microorganism such as yeast. Any of these can be used commercially.
  • plant-derived tampa As a protein degradation product, Hainyut R * (made by Fuji Oil Co., Ltd., soybean protein degradation product) is used.
  • As a protein degradation product derived from animals extra Y * (made by Asahi Foods, a meat protein degradation product) is used. ), And Meiji CPP (Casein protein hydrolyzate manufactured by Meiji Seika Co., Ltd.).
  • microorganism-derived protein hydrolysates examples include yeast extract Kyowa (Kyowa Hakko, Yeast protein hydrolyzate). Among the above names, those marked with * are trademarks.
  • the i3-darcosidase which acts on the ylided glycoside and the protein hydrolyzate may be any one having ⁇ -darcosidase activity.
  • an almond extract For example, a crude enzyme solution having a -3-dalcosidase activity can be used.
  • naringinase manufactured by Amano Pharmaceutical
  • coclase SS manufactured by Sankyo
  • cellulase Nagase manufactured by Nagase Seikagaku
  • Sumiteam AC Sumiteam C
  • Separeth GF Commercial products such as (Joint sake refining) can be used.
  • the treatment with darkosidase is not particularly limited as long as it is a treatment method for producing gardenia blue pigment.
  • an iridoid glycoside, a protein degradation product, and i3-darcosidase coexist in the temperature range of 20 to 70 t: usually 30 minutes under the aerobic condition by the above stirring or shaking.
  • the processing method can be exemplified for about 24 hours.
  • Examples of the polyphenol used for the gardenia blue pigment obtained by the above method include tannin, catechins, quercetin glycoside, gallic acid, and myricitrine.
  • tannins include hydrolyzable tannins, which are generally hydrolyzed with an acid, and condensed tannins obtained by condensing a plurality of tekins, epicatechins and epiga oral techins, and any of these tannins is used in the present invention. You can do it.
  • tannic acid is used as the hydrolyzable tannin
  • apple polyphenol pudo is used as the condensed tannin.
  • seed polyphenol, oolong tea extract and the like seed polyphenol, oolong tea extract and the like.
  • humic acid or ellagic acid obtained by further hydrolyzing the above hydrolysable humic acid can be used.
  • Catechins include catechin, epicatechin, epigallocatechin, catechin gallate, epicatechin gallate and epigallocatechin gallate. Also, a polyphenol composed of a mixture of two or more of these can be used.
  • quercetin glycoside examples include rutin, isoquercitrin, enzyme-treated rutin, and enzyme-treated isoquercitrin.
  • polyphenol tannic acid, ellagic acid, catechin, enzyme-treated rutin, enzyme-treated isoquercitrin, gallic acid, and myricitrin are preferred.
  • the polyphenol can be used in the form of a composition containing not only the above-mentioned single compound but also the above-mentioned various polyphenols in any composition and ratio.
  • Embodiments of the latter compositions include plant extracts, such as herbs such as mouthsum, sage, anis, chamomile, elder, lemon balm, thyme, western saw, and karin. Extracts: Extracts of plants containing a large amount of flaponoids such as buckwheat, buckwheat, azuki, bayberry, eucalyptus and cucumber can be mentioned.
  • the extraction solvent for the plant extract include water, alcohols such as ethanol, and a mixture thereof.
  • these polyphenols may be separated and purified from natural products or artificially produced.
  • these polyphenols commercially available ones can be used simply.
  • tannic acid reagent (Wako Pure Chemical Industries) is used as tannic acid
  • sun catechin aqueous * is used as catechin
  • polyphenone G is used.
  • the mixing ratio of the gardenia blue dye obtained by the above-mentioned method and the above-mentioned polyphenol is not particularly limited, but for example, the color value ( E1M10 % ) at the maximum absorption wavelength near the blue absorption (wavelength 580 to 620 nm) is 0. It is desirable to mix the polyphenol in a ratio of 0.05 to 5 parts by weight, preferably 0.1 to 1 part by weight, with respect to 100 parts by weight of the gardenia blue pigment which is 1.
  • the color value (E li , lfl3 ⁇ 4 ) of 0.1 is defined as the absorbance (maximum near the blue absorption) of a 10 w / v% solution of gardenia blue dye measured at a liquid layer width (cell width) of 1 cm. Absorption wavelength) is 0.1.
  • the gardenia blue dye of the present invention can be produced by a method of producing a gardenia blue dye by reacting an iridoid glycoside with ⁇ -darcosidase and a protein degradation product (Japanese Patent Application Laid-Open Nos. 52-53934 and 52-53934).
  • a method of producing a gardenia blue dye by reacting an iridoid glycoside with ⁇ -darcosidase and a protein degradation product
  • the iridoid glycoside is converted into a proteolytic product in the above-mentioned method for producing the gardenia blue pigment.
  • It can also be prepared by blending a polyphenol in a treated product (crude product) containing a gardenia blue dye obtained by treating with 3-darcosidase in the presence of phenol.
  • the gardenia blue dye of the present invention can also be prepared by producing the gardenia blue dye by the above method in the presence of polyphenol. 10 You can. That is, the gardenia blue dye of the present invention is obtained by performing the / 3-darcosidase treatment in the presence of an iridide glycoside and a protein hydrolyzate in the presence of polyphenol in the process of producing the gardenia blue dye in the above method. It can be manufactured by doing.
  • the mixing time of the polyphenol is not particularly limited as long as it is as described above.
  • the gardenia blue pigment having an improved color tone of the present invention is obtained by adding / 3-darcosidase to a mixture of an iridide glycoside and a protein hydrolyzate obtained by extracting from the fruits of the gardenia prunus gardenia.
  • the enzymatic treatment with [3] -dalcosidase can be performed by performing the enzymatic treatment (] 3_darcosidase) in the presence of the formulated polyphenol without any limitation.
  • the j3-darcosidase treatment is not particularly limited, but i3-darcosidase is blended with the object to be treated and treated under stirring or shaking conditions (under aerobic conditions). This means that the treatment is carried out under aerobic conditions in a temperature range of 20 to 70 ° C., usually for about 30 minutes to 24 hours.
  • the production of the gardenia blue pigment of the present invention is not particularly limited to the reaction conditions, the operation method, the raw materials used, etc., except that porifenol is used as a material component in the production process. You can follow the method.
  • Ylidoid glycosides, proteolysates used with the said ylided glycosides, iridoid glycosides and Z or proteolysates) 3-Glucosidase can be used in the same manner as described above.
  • the gardenia blue pigment is a gardenia blue pigment-containing solution obtained by the above method.
  • filtration treatment, centrifugal separation treatment, resin treatment, membrane treatment and the like can be separated and adjusted according to a conventional method.
  • the gardenia blue pigment thus obtained can be provided as it is as a pigment preparation, or a diluent, carrier or other additives can be blended as another component and provided as a pigment preparation in that state. You can also.
  • diluents, carriers and additives include a wide variety of pigment preparations, especially those used in water-soluble pigment preparations, as long as they do not impair the effects of the present invention.
  • examples include sucrose, glucose, and the like. Dextrin, gum arabic, water, ethanol, propylene dalicol, glycerin, syrup and the like can be mentioned.
  • the form of the pigment preparation is not particularly limited, and it can be prepared in any form such as powder, granule, tablet, liquid, emulsion, paste and the like.
  • the color tone of the conventional gardenia blue pigment is red-purple blue
  • the gardenia blue pigment of the present invention obtained by the above method has an a value of Hunter Lab color system (Lab value). ⁇ 4, more preferably ⁇ 5, and the L value is 70 or more, preferably 72 or more.
  • the gardenia blue pigment of the present invention provides a bright blue or greenish blue with a small amount of red-purple blue compared to the red-purple blue of the conventional gardenia blue pigment. Have.
  • the Hunter Lab color system is a color system that forms a color solid composed of rectangular coordinates consisting of a and b axes indicating chromaticity and an L axis perpendicular to the coordinate system.
  • Increasing on the positive side increases redness
  • increasing on the negative side increases greenness
  • increasing b on the positive side increases yellowness
  • increasing on the negative side increases bluishness.
  • a gardenia blue dye obtained by the action of -dalcosidase on an yridide glycoside and a protein hydrolyzate described in JP-A-52-53934 and JP-A-56-92792
  • a pigment preparation of a gardenia blue pigment having an improved color tone, having a light blue color with a reduced red to violet color or a light blue color with a green color, as compared with the preparation, can be provided.
  • the gardenia blue pigment preparation of the present invention with improved color tone can be widely used as a coloring agent for foods, cosmetics, pharmaceuticals, quasi-drugs, feeds, and the like, according to common practice.
  • Example 1 Example 1
  • Gardenia blue pigment was prepared using enzyme-treated isoquercitrin, tannic acid or catechin as polyphenol, and the color value and color tone of the obtained gardenia blue pigment were examined.
  • a dye was obtained (maximum absorption wavelength: 594 nm).
  • Enzyme-treated isoquercitrin preparation [Sammeline AO-1007 * (15 Enzyme-treated isoquercitrin): Saneigen FFA Co., Ltd.], tannic acid preparation (100 ml of the dye solution) as a polyphenol A tannic acid reagent: Wako Pure Chemical Industries, Ltd.) or Kitekin preparation (Polyphenone G *: Mitsui Norin Co., Ltd.) was added at the ratio shown in Table 1, 2 or 3, respectively, and stirred at room temperature for 5 minutes. Thereafter, the color value and color tone of each dye solution were measured.
  • the measurement of the color value (E lem 1D, as the absorbance of the sample to be measured (wavelength 580 ⁇ 620Nra) is in the range of 0.3 to 0.7, the sample was precisely weighed, the ion-exchanged water In addition, the volume was adjusted to exactly 50 ml, and the absorbance at the maximum absorption region in the wavelength range of 580 to 620 ⁇ was measured using a cell with a liquid layer length of 1 cm. V560). The evaluation of color tone was performed visually using the Hunter La color system.
  • the measurement was carried out by measuring the spectral transmittance using a UV-visible spectrophotometer (V560, manufactured by 1ASC0).
  • Tables 1, 2, and 3 show the results of examining the color value and color tone (Hunter Lab color system) of gardenia blue pigment prepared using enzyme-treated isoquercitrin, tannic acid, and potassium techin as polyphenol, respectively. .
  • HUE means hue (HUE: , (: 10 ⁇ 3 ⁇ 48 is saturation (+ ') 1/2 ), DELTA-E ([(AL) 2 + (Aa) 2 + (Ab)] l / 2 ) is a unit that expresses the color difference
  • the values were reduced to -5, -6, and -7 or less, and the b value was similarly shifted to the negative side, and tended to decrease from the original value of -24.41.
  • the L value is And tended to be larger than 72, 01. From this, it can be seen that the color tone of the gardenia blue pigment has changed to a bright blue color with reduced red to purple or a bright blue color with a greenish tint.
  • the L value tended to be larger than the original 72.01. This also indicates that the color tone of the gardenia blue pigment has changed to a light blue color with a reduced red-purple color or a light blue color with a greenish tint.
  • Gardenia blue pigment was prepared by the following method, using enzyme-treated isoquercitrin, oxalic acid, or catechin as the polyphenol in the same manner as in Example 1.
  • 10.0 g of soybean protein hydrolyzate 10.0 g
  • 90 m 1 of water 1 g of darcosidase (manufactured by Oriental Yeast, 2000 uni ts) and 20 mg, 40 mg and 60 mg of polyphenol (enzyme-treated isoquercitrin, tannic acid, catechin)
  • the mixture is stirred at pH 6 to 8 and 40 to 60 ° C. for 24 hours to obtain a gardenia blue pigment.
  • Example 1 As a result, as in Example 1, as the amount of polyphenol added increases, the color tone of the gardenia blue pigment takes on a bright blue or green color in which red to purple is reduced from red to purplish blue. The color changed to a light blue color.
  • the present invention it is possible to provide a gardenia blue pigment preparation having a bright blue color with a light blue or greenish color with little red to purple.
  • the conventional gardenia blue pigment has a red-purple blue color tone.
  • the present invention can provide variety to the color tone of a gardenia blue pigment by providing a gardenia blue pigment having a color tone different from that of a conventional gardenia blue pigment.

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Zoology (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Biotechnology (AREA)
  • Microbiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Mycology (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)

Abstract

L'invention concerne une préparation de colorant bleu de jasmin du Cap (Gardenia jasminoides) présentant un ton lumineux de bleu ou de vert avec une couleur légèrement rougeâtre ou violacée. Cette préparation de colorant peut être obtenue par mélange d'un polyphénol avec un colorant bleu de jasmin du Cap préparé par traitement d'un iridoïde glycoside avec de la β-glucosidase, en présence d'un produit de digestion protéique, ou par traitement d'un iridoïde glycoside et d'un produit de digestion protéique avec de la β-glucosidase, en présence d'un polyphénol, au cours du procédé de fabrication de la préparation de colorant bleu de jasmin du Cap
PCT/JP2002/010100 2001-09-28 2002-09-27 Preparation de colorant bleu de jasmin du cap a ton ameliore WO2003029358A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2003532591A JP4374494B2 (ja) 2001-09-28 2002-09-27 色調が改善されたクチナシ青色素の色素製剤

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2001304559 2001-09-28
JP2001-304559 2001-09-28

Publications (1)

Publication Number Publication Date
WO2003029358A1 true WO2003029358A1 (fr) 2003-04-10

Family

ID=19124461

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2002/010100 WO2003029358A1 (fr) 2001-09-28 2002-09-27 Preparation de colorant bleu de jasmin du cap a ton ameliore

Country Status (2)

Country Link
JP (1) JP4374494B2 (fr)
WO (1) WO2003029358A1 (fr)

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2005213328A (ja) * 2004-01-28 2005-08-11 Maruzen Pharmaceut Co Ltd 天然系防曇剤、防曇剤組成物及び曇り防止方法
WO2006082922A1 (fr) * 2005-02-03 2006-08-10 San-Ei Gen F.F.I., Inc. Colorant bleu gardenia a ton ameliore et procede de fabrication associe
JP4605824B1 (ja) * 2010-08-10 2011-01-05 三井製糖株式会社 赤色素の製造方法及び当該赤色素を含む飲食品
WO2011132334A1 (fr) * 2010-04-20 2011-10-27 三井製糖株式会社 Procédé de production d'un pigment rouge, et aliments et boissons contenant ce pigment rouge
WO2012043173A1 (fr) * 2010-09-27 2012-04-05 理研ビタミン株式会社 Procédé pour la production de pigment bleu de gardénia
JP2012520828A (ja) * 2009-03-20 2012-09-10 ナチュラ コスメティコス ソシエダッド アノニマ チブサノキエキス沈澱から不溶性物質を得る方法、チブサノキエキス沈澱からの物質およびその用途
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
USRE46695E1 (en) 2008-03-28 2018-02-06 Wild Flavors, Inc. Stable natural color process, products and use thereof
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
WO2020213448A1 (fr) * 2019-04-16 2020-10-22 グリコ栄養食品株式会社 Pigment bleu de gardénia et procédé pour la production de celui-ci
US11174390B2 (en) 2015-09-29 2021-11-16 Riken Vitamin Co., Ltd. Gardenia pigment preparation
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
WO2024127616A1 (fr) * 2022-12-16 2024-06-20 グリコ栄養食品株式会社 Pigment bleu de gardénia et son procédé de production
JP7577751B2 (ja) 2020-08-28 2024-11-05 グリコ栄養食品株式会社 青色色素及びその製造方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH01179690A (ja) * 1987-12-30 1989-07-17 Narisu Keshohin:Kk 明色化された天然青色系色素の製造方法
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
JP2002322384A (ja) * 2001-04-25 2002-11-08 Mitsubishi Chemicals Corp 緑色用色素製剤

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH01179690A (ja) * 1987-12-30 1989-07-17 Narisu Keshohin:Kk 明色化された天然青色系色素の製造方法
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
JP2002322384A (ja) * 2001-04-25 2002-11-08 Mitsubishi Chemicals Corp 緑色用色素製剤

Cited By (34)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4502648B2 (ja) * 2004-01-28 2010-07-14 丸善製薬株式会社 天然系防曇剤、防曇剤組成物及び曇り防止方法
JP2005213328A (ja) * 2004-01-28 2005-08-11 Maruzen Pharmaceut Co Ltd 天然系防曇剤、防曇剤組成物及び曇り防止方法
WO2006082922A1 (fr) * 2005-02-03 2006-08-10 San-Ei Gen F.F.I., Inc. Colorant bleu gardenia a ton ameliore et procede de fabrication associe
JPWO2006082922A1 (ja) * 2005-02-03 2008-06-26 三栄源エフ・エフ・アイ株式会社 色調が改善されたクチナシ青色素とその製造方法
JP4637896B2 (ja) * 2005-02-03 2011-02-23 三栄源エフ・エフ・アイ株式会社 色調が改善されたクチナシ青色素とその製造方法
USRE46695E1 (en) 2008-03-28 2018-02-06 Wild Flavors, Inc. Stable natural color process, products and use thereof
JP2012520828A (ja) * 2009-03-20 2012-09-10 ナチュラ コスメティコス ソシエダッド アノニマ チブサノキエキス沈澱から不溶性物質を得る方法、チブサノキエキス沈澱からの物質およびその用途
JP2016065047A (ja) * 2009-03-20 2016-04-28 ナチュラ コスメティコス ソシエダッド アノニマ チブサノキエキス沈澱から不溶性物質を得る方法、チブサノキエキス沈澱からの物質およびその用途
WO2011132334A1 (fr) * 2010-04-20 2011-10-27 三井製糖株式会社 Procédé de production d'un pigment rouge, et aliments et boissons contenant ce pigment rouge
CN102300477A (zh) * 2010-04-20 2011-12-28 三井制糖株式会社 红色素的制造方法及含有该红色素的饮食品
JP2012036334A (ja) * 2010-08-10 2012-02-23 Mitsui Sugar Co Ltd 赤色素の製造方法及び当該赤色素を含む飲食品
JP4605824B1 (ja) * 2010-08-10 2011-01-05 三井製糖株式会社 赤色素の製造方法及び当該赤色素を含む飲食品
WO2012043173A1 (fr) * 2010-09-27 2012-04-05 理研ビタミン株式会社 Procédé pour la production de pigment bleu de gardénia
JP2012067241A (ja) * 2010-09-27 2012-04-05 Riken Vitamin Co Ltd クチナシ青色素の製造方法
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
EA028521B1 (ru) * 2011-11-07 2017-11-30 Уайлд Флэйворс, Инк. Богатый генипином материал и его применение
WO2013070682A1 (fr) * 2011-11-07 2013-05-16 Wild Flavors, Inc. Matériau riche en génipine et son utilisation
USRE47153E1 (en) 2011-11-07 2018-12-11 Wild Flavors, Inc. Genipin-rich material and its use
CN113142466A (zh) * 2011-11-07 2021-07-23 天然香料公司 富含京尼平的材料及其用途
EP3238550A1 (fr) * 2011-11-07 2017-11-01 Wild Flavors, Inc. Matériau riche en génipine et son utilisation
US11174390B2 (en) 2015-09-29 2021-11-16 Riken Vitamin Co., Ltd. Gardenia pigment preparation
CN113748169B (zh) * 2019-04-16 2024-05-17 格力高营养食品株式会社 栀子蓝色素及其制造方法
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
WO2020213448A1 (fr) * 2019-04-16 2020-10-22 グリコ栄養食品株式会社 Pigment bleu de gardénia et procédé pour la production de celui-ci
CN113748169A (zh) * 2019-04-16 2021-12-03 格力高营养食品株式会社 栀子蓝色素及其制造方法
EP3957690A4 (fr) * 2019-04-16 2023-01-25 Glico Nutrition Co., Ltd. Pigment bleu de gardénia et procédé pour la production de celui-ci
EP3957689A4 (fr) * 2019-04-16 2023-01-25 Glico Nutrition Co., Ltd. Pigment bleu de gardénia et son procédé de production
JP7558154B2 (ja) 2019-04-16 2024-09-30 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
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
EP4206288A1 (fr) * 2020-08-28 2023-07-05 Glico Nutrition Co., Ltd. Pigment bleu et son procédé de production
EP4206288A4 (fr) * 2020-08-28 2024-09-18 Glico Nutrition Co Ltd Pigment bleu et son procédé de production
CN115996992A (zh) * 2020-08-28 2023-04-21 格力高营养食品株式会社 蓝色色素及其制造方法
JP7577751B2 (ja) 2020-08-28 2024-11-05 グリコ栄養食品株式会社 青色色素及びその製造方法
WO2024127616A1 (fr) * 2022-12-16 2024-06-20 グリコ栄養食品株式会社 Pigment bleu de gardénia et son procédé de production

Also Published As

Publication number Publication date
JP4374494B2 (ja) 2009-12-02
JPWO2003029358A1 (ja) 2005-01-13

Similar Documents

Publication Publication Date Title
Fan et al. Composition and colour stability of anthocyanins extracted from fermented purple sweet potato culture
JP4637896B2 (ja) 色調が改善されたクチナシ青色素とその製造方法
EP3536166B1 (fr) Procédé de couleur naturelle stable
WO2003029358A1 (fr) Preparation de colorant bleu de jasmin du cap a ton ameliore
Hurtado et al. Colour, pH stability and antioxidant activity of anthocyanin rutinosides isolated from tamarillo fruit (Solanum betaceum Cav.)
Roobha et al. The effect of light, temperature, pH on stability of anthocyanin pigments in Musa acuminata bract.
Sadilova et al. Matrix dependent impact of sugar and ascorbic acid addition on color and anthocyanin stability of black carrot, elderberry and strawberry single strength and from concentrate juices upon thermal treatment
Aishah et al. Anthocyanins from Hibiscus sabdariffa, Melastoma malabathricum and Ipomoea batatas and its color properties.
Burtch et al. Reaction kinetics of monomeric anthocyanin conversion to polymeric pigments and their significance to color in interspecific hybrid wines
Sira et al. A laboratory scale method for isolation of starch from pigmented sorghum
CN103958614A (zh) 花青素基着色剂
US8425960B2 (en) Modification of the color hue of anthocyanins for the obtention of coloring substances
Abdullah et al. Multiple color and pH stability of floral anthocyanin extract: Clitoria ternatea
Gennaro et al. High-performance liquid chromatography of food colours and its relevance in forensic chemistry
Burin et al. Phenolic composition, colour, antioxidant activity and mineral profile of Cabernet Sauvignon wines
Żbik et al. Comparison of the effects of extraction method and solvents on biological activities of phytochemicals from selected violet and blue pigmented flowers
JP5514602B2 (ja) 紅麹色素組成物、紅麹色素の退色防止方法、紅麹製造方法、紅麹又はその抽出物、それらを含む食品及び化粧品
KR101054624B1 (ko) 적색소의 제조 방법과 이 적색소를 포함하는 음식품
US20050208189A1 (en) Extract of by-products of the treatment of nuts and pulses, method for the production thereof and use of the same
Wattanuruk et al. Total phenolics, flavonoids, anthocyanins and antioxidant activities of Khaow-Mak extracts from various colored rice
Wesche-Ebeling et al. Stabilization mechanisms for anthocyanin: the case for copolymerization reactions
WO2022044291A1 (fr) Pigment bleu et son procédé de production
JPH10110109A (ja) 耐光性を改善した紅麹色素および耐光性改善方法
CN116686934B (zh) 一种食用色素-蛋白多糖复合物及其制备方法
JP2000119549A (ja) 耐光性を改善した紅麹色素、紅麹およびその製造法

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AE AG AL AM AT AU AZ BA BB BG BY BZ CA CH CN CO CR CU CZ DE DM DZ EC EE ES FI GB GD GE GH HR HU ID IL IN IS JP KE KG KR KZ LK LR LS LT LU LV MA MD MG MK MW MX MZ NO NZ OM PH PL PT RO SD SE SG SI SK SL TJ TM TN TR TT UA UG US UZ VC VN YU ZA ZM

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): GH GM KE LS MW MZ SD SL SZ UG ZM ZW AM AZ BY KG KZ RU TJ TM AT BE BG CH CY CZ DK EE ES FI FR GB GR IE IT LU MC PT SE SK TR BF BJ CF CG CI GA GN GQ GW ML MR NE SN TD TG

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
121 Ep: the epo has been informed by wipo that ep was designated in this application
WWE Wipo information: entry into national phase

Ref document number: 2003532591

Country of ref document: JP

122 Ep: pct application non-entry in european phase