WO2019111861A1 - Composition de pigment rouge dérivé d'un composé iridoïde et procédé pour sa production - Google Patents

Composition de pigment rouge dérivé d'un composé iridoïde et procédé pour sa production Download PDF

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WO2019111861A1
WO2019111861A1 PCT/JP2018/044449 JP2018044449W WO2019111861A1 WO 2019111861 A1 WO2019111861 A1 WO 2019111861A1 JP 2018044449 W JP2018044449 W JP 2018044449W WO 2019111861 A1 WO2019111861 A1 WO 2019111861A1
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Prior art keywords
iridoid
compound
pigment composition
red
red pigment
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PCT/JP2018/044449
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English (en)
Japanese (ja)
Inventor
敬子 泉田
浜崎　孝治
貴正 横山
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三栄源エフ・エフ・アイ株式会社
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Priority to JP2019558203A priority Critical patent/JPWO2019111861A1/ja
Publication of WO2019111861A1 publication Critical patent/WO2019111861A1/fr

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    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/22—Heterocyclic compounds, e.g. ascorbic acid, tocopherol or pyrrolidones
    • 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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • 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
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • 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

Definitions

  • the present invention relates to an iridoid compound-derived red pigment composition and a method for producing the same. More specifically, the present invention relates to a technology for producing a red-pigment composition derived from an iridoid compound having a color tone and a combination of light-redness, which can be used in various fields.
  • Gardenia red pigment is a pigment exhibiting a red color tone produced from a gardenia fruit extract, and is a natural pigment having relatively high stability to light and heat.
  • the gardenia red pigment is a pigment compound obtained by reacting the aglycone of the iridoid compound contained in the gardenia fruit extract with an amino group-containing compound.
  • the pigment having a red color tone has been developed by improving a part of the process of producing the blue pigment which is a pigment compound having a structure derived from an iridoid compound (patented) Literature 1).
  • gardenia red pigment also overlaps with the consumer's safety intention in recent years because it is derived from plant raw materials, and instead of insect-derived cochineal pigment and other synthetic red pigment etc., food, drink, cosmetics, quasi-drugs and medicine Demand in many fields such as is expanding.
  • the gardenia red pigment is used as an excellent pigment material which can also be used in the food and beverage field.
  • the conventional gardenia red pigment generally tends to exhibit a bluish dark purple red tone, but is not suitable for coloring a food material to be bright red.
  • the characteristic regarding the said color is a place which does not raise a problem in particular if the color assumed the dark red or muddy purple system or the target material itself is originally dark color, etc., while milk white food materials such as dairy products and paste products Also, its use is difficult in applications where the beverage etc. is colored bright red etc.
  • Patent Document 2 As a prior art related to lightening of a gardenia red pigment, a technology related to Patent Document 2 is disclosed.
  • a method of using a specific amino acid or a salt thereof as a primary amino group-containing substance and adding an excessive amount of a specific organic acid at the time of red color development in the production process ( Patent Document 2).
  • excessive addition of citric acid or the like is one of the solution means (Patent Document 2 left column, lines 3 to 8 and lines 30 to 32; Example 1, Tables 1 and 2 and the like)
  • Patent Document 2 left column, lines 3 to 8 and lines 30 to 32; Example 1, Tables 1 and 2 and the like Example 1, Tables 1 and 2 and the like
  • Patent Document 3 a method of adding a sulfite ion such as sodium pyrosulfite or potassium pyrosulfite in the formation reaction of the pigment composition
  • Patent Document 4 a method of adding a taurine-containing substance
  • Patent Document 4 a method of adding the substance of patent document 4
  • the lightening effects of these compounds in Patent Document 3 and Patent Document 4 are high in L value but low in b value and strong in bluish color (Patent Document 3 paragraph 0027 and Example, Patent Document 4 paragraph 0035) And, it can not be recognized as a color tone that can achieve the vivid red color tone which is the subject of the present application.
  • sulfite ions such as sodium metabisulfite and potassium pyrosulfite used in the technology according to Patent Document 3 are compounds that are concerned about the effects when used in food and drink applications, and removal processing was performed in the subsequent steps. It is also recognized as a technology that can be avoided for the current consumer who is highly security oriented.
  • the taurine-containing substance used in the technology according to Patent Document 4 is a substance whose price per unit weight is so expensive that it can not be compared with ordinary organic acids etc., there is a problem in the point of raw material acquisition. It is also recognized.
  • the present invention has been made in view of the circumstances of the prior art described above, and the subject of the present invention is a technique relating to the production of an iridoid compound-derived red pigment composition, and in terms of the safety of the produced pigment composition.
  • a suitable technology and a technology for producing a red pigment composition having a combination of redness and lightness that can be used in various fields including milky white products, beverages, etc., not simply improvement in lightness.
  • the purpose is
  • the inventors of the present invention conducted intensive studies in the state of the above-mentioned prior art, and found that ascorbic acid was used in the step of performing red color development accompanied by the action of iridoid aglycone having a carboxyl group at position 4 of iridoid skeleton and an amino group containing compound. I conceived the method of adding excess. The inventors of the present invention developed a red color by the method based on the above idea, and thus a beautiful red iridoid compound-derived red pigment composition having both bright redness and bright redness whose color tone was shifted to the yellow side was prepared. I found that.
  • the present inventors intensively researched, when the ascorbic acid addition amount in the organic acid added in red color development is more than fixed, the above-mentioned "color tone excellent in reddishness" is achieved. I found it to be done. And when the total amount of all the organic acids containing ascorbic acid in the said red color development is more than fixed, it discovered that it became a color tone to which lightness and chroma were fully provided. In addition, the present inventors can prepare a red pigment composition with variations in color tone by changing the ratio of ascorbic acid and other organic acids to be added together with the above conditions. Found out.
  • the color tone excellent in reddish color is that “a value, b value, and CHROMA value in the Hunter Lab color system show high values due to“ action of ascorbic acid ”in red color development.
  • the lightness (L value) is bluish even though the lightness (L value) is improved compared to before the increase.
  • it exhibits a dark color tone, and a gardenia red pigment having both bright redness and lightness is not realized (Examples 1 and 2 of the present specification).
  • Patent Document 2 which is the prior art as described above, ascorbic acid is described as one of them in the paragraph of the list of examples of organic acids (Patent Document 2 p2 right column, lines 2-3),
  • Patent Document 2 is only parallel writing of the citric acid etc. which do not show the reddishness which concerns on this invention.
  • Patent Document 2 an example using ascorbic acid is only described as a comparative example as one of usage examples in the case where lightness is not sufficient (Patent Document 2 p3 right side Table 1 and No. 1 Lines 19-21).
  • Patent Documents 3 and 4 Although ascorbic acid is listed and listed as an example of an organic acid also in patent documents 3 and 4 (patent document 3 paragraph 0036, patent document 4 paragraph 0030), also in these descriptions, the bright redness concerning the present invention is mentioned.
  • Patent Documents 3 and 4 only the example in which citric acid is added as an organic acid is disclosed.
  • Patent Documents 2 to 4 are only documents disclosing inventions based on technical ideas different from the present invention, and even when the descriptions of these documents are taken into consideration, It can not be understood that the excellent bright red tone which can not be achieved by other organic acids such as citric acid can be realized when the acid is added at the time of red color development.
  • Step 1 In a method of producing an iridoid compound-derived red pigment composition, (Step 1) Red coloration accompanied by the action of an iridoid aglycone having a carboxyl group at the 4-position of the iridoid skeleton and an amino group-containing compound, The organic acid containing ascorbic acid, its analogous compound, or two or more compounds selected from these is carried out in a solution containing 4 molar equivalents or more in total of organic acids relative to the total molar equivalents of iridoid compounds, Producing a red pigment compound having a color forming property having bright redness and lightness, A method for producing an iridoid compound-derived red pigment composition, comprising: [Section 2] The step of performing the red coloration described in the above (Step 1) is In addition to ascorbic acid, its analogous compounds, or two or more
  • Step 3 The step of performing the red coloration described in the above (Step 1) is It is carried out in a solution containing one molar equivalent or more of ascorbic acid, an analogue thereof, or two or more compounds selected therefrom with respect to the total molar equivalent of the iridoid compound.
  • the manufacturing method of the iridoid compound origin red pigment composition as described in claim 1 or 2.
  • the step of performing the red coloration described in the above (Step 1) is As a molar ratio with respect to the total amount of organic acids, it is carried out in a solution containing 12.5% or more of ascorbic acid, its analogous compounds, or two or more compounds selected therefrom.
  • Item 4. A method for producing an iridoid compound-derived red dye composition according to any one of Items 1 to 3.
  • the step of performing the red coloration described in the above (Step 1) is The organic acid may be selected from citric acid, succinic acid, malic acid, lactic acid, tartaric acid, fumaric acid, or similar compounds thereof, in addition to ascorbic acid, its analogous compounds, or two or more compounds selected therefrom.
  • the step described in the above (Step 1) is carried out prior to and / or in parallel with the formation of a red color, from the formation of iridoid aglycone from iridoid glucoside by ⁇ -glycosidic bond hydrolysis.
  • Item 1 shows a pigment composition prepared in the same manner as 1-1).
  • Item 8 An iridoid compound-derived red pigment composition obtained by the method according to any one of Items 1 to 7.
  • Item 11 Item 11.
  • a dye preparation comprising the iridoid compound-derived red dye composition according to item 9 or 10.
  • Section 12 Item 11.
  • Item 8 Item 8.
  • a pigment preparation, a food or drink, a cosmetic, a medicine, a quasi-drug comprising a step of containing the iridoid compound-derived red pigment composition obtained by the method according to any one of items 1 to 7 , Sanitation daily necessities, or methods of producing feed.
  • the present invention is a technique relating to the production of an iridoid compound-derived red pigment composition, which is a suitable technique from the viewpoint of the safety of the pigment composition produced, and includes various products including milky white products, beverages, etc. It is possible to provide a red pigment composition having a combination of redness and lightness that can be used in various fields. According to the present invention, it becomes possible to provide, for example, a gardenia red pigment having a bright redness and a light colorability that can be used also for bright red coloring of milky white products, beverages etc., and it is difficult with conventional gardenia red pigment It can be widely used for various applications and products.
  • FIG. 6 is a diagram showing the plotting results on the a-axis and b-axis orthogonal coordinates of the Hunter Lab color system in the evaluation of coloring properties of the gardenia red pigment composition according to Example 1.
  • the present invention relates to a red pigment composition derived from an iridoid compound having both bright redness and lightness, a method for producing the same, and use thereof.
  • a red pigment composition derived from an iridoid compound having both bright redness and lightness a method for producing the same, and use thereof.
  • embodiments of the present invention will be described in detail.
  • This application is an application accompanied by a priority claim based on Japanese Patent Application No. 2017-233021 filed by the present applicant in Japan, the entire contents of which are incorporated by reference into the present application.
  • the iridoid compound derived red pigment composition according to the present invention can be prepared and manufactured according to the process described below.
  • the manufacturing method according to the present invention unless it substantially interferes with the function and effect exerted by the technical feature according to the present invention, excluding including other steps other than the steps described below. Absent.
  • the technical scope concerning this invention is not limited to the aspect including all the following processes except an essential process.
  • the process for producing the iridoid compound-derived red pigment composition according to the present invention comprises: (Step 1) ascorbic acid, red color development accompanied by the action of iridoid aglycone having a carboxyl group at the 4-position of iridoid skeleton and an amino group containing compound;
  • the reddish color is obtained by a solution containing an organic acid containing the similar compound or two or more compounds selected from these, in a total amount of the organic acid of 4 molar equivalents or more to the total molar equivalent of the iridoid compound.
  • a step of producing a red dye compound having a color forming property having lightness is
  • the "iridoid compound” refers to a compound having an iridoid skeleton.
  • a compound having an iridoid skeleton refers to a compound including a structure comprising a 5-membered ring fused to a hetero 6-membered ring containing oxygen, and more specifically, a basic skeleton represented by the structural formula (I) It refers to a compound having a structure.
  • structural formula (I) the ring structure is given to the iridoid skeleton constituent atoms by numbering.
  • the iridoid compound in the present specification is used as a term including not only iridoid glycosides but also the aglycone iridoid aglycone. Moreover, as an iridoid compound in this specification, the thing of the ionic state at the time of melt
  • dissolution is also included.
  • R 1 , R 2 , R 3 , R 4 , and R 5 in the structural formulas refer to any functional groups, but in the reaction substrate for red color development according to the present invention, R 1 is a carboxyl group It becomes. When R 1 is a lower alkylated functional group such as a methyl ester group, it can be used as a reaction substrate by converting it to a carboxyl group via ester hydrolysis.
  • the iridoid compounds contained in plants and fruits usually have an inactive and stable glycoside structure in many cases.
  • R 2 is a sugar molecule linked via a ⁇ -glycosidic bond.
  • aglycone which is a reaction substrate for red color development according to the present invention, it has a structure in which a hydroxyl group (—OH) is added to the 1 position of the iridoid skeleton. Specifically, the structure is represented by Structural Formula (II).
  • R 3 , R 4 , and R 5 have many compounds containing a hydrogen atom (—H) as a functional group but have a hydroxyl group, an alkyl group, or a functional compound containing a phenyl compound are also reported. ing. Also, although there are many examples where R 3 and R 4 are a hydrogen atom (—H), examples of compounds such as an alkyl group or an alkyl alcohol group are also reported for R 3 and R 5 .
  • a structure having a double bond shown in structural formula (III) or structural formula (IV) also included.
  • the carbons at positions 6 and 7 of the iridoid skeleton and / or the carbons at positions 7 and 8 of the iridoid skeleton may be bonded via a common atom or molecular structure.
  • structures such as structural formula (V), structural formula (VI) and the like bonded via oxygen can be mentioned.
  • an embodiment in which the compound is provided with various functional groups is acceptable as long as the stability and coloring properties of the red dye composition according to the present invention are not substantially impaired.
  • the method for producing a red pigment composition according to the present invention is a method for performing red color development accompanied by the action of an iridoid aglycone having a carboxyl group at the 4-position of the iridoid skeleton and an amino group-containing compound.
  • an iridoid aglycone having a carboxyl group at the 4-position of the iridoid skeleton refers to an aglycone produced from an iridoid glycoside having a carboxyl group at the fourth position in the iridoid skeleton.
  • Specific examples of the compound include genipinic acid and the like.
  • Genipinic acid is an aglycone of geniposidic acid which is abundantly contained in gardenia fruits. It is also a compound obtained by hydrolyzing the 4-position methyl ester group of the iridoid skeleton of genipin to a carboxyl group.
  • Raw material plant As a manufacturing method of the red pigment composition concerning the present invention, it is suitable to use a plant containing an iridoid compound as a raw material as a raw material.
  • raw materials according to the present invention for example, gardenia, wit (genipa americana), catalpa, silkworm, and the like can be mentioned.
  • part of a plant body although it is also possible to use any site
  • gardenia jasminoides can be mentioned in detail.
  • plants belonging to gardenia also include hybrids with these close relatives and close relatives.
  • plants belonging to gardenia mention may be made in particular of Gardenia jasminoides.
  • the iridoid compound containing extract from a plant body can be used as a raw material.
  • the extraction method of the iridoid compound from the plant can be performed by a known method and is not particularly limited, but it is preferable to adopt a method in which the yield of the iridoid compound is increased.
  • preparation of an extract from a plant body for example, the raw material is crushed, crushed, ground, crushed, crushed, powdered, dried and the like, and then treated with water, water-containing alcohol, alcohol or the like. What was extracted and processed, such as filtration and refinement
  • the red coloration according to the present invention is carried out by using an iridoid aglycone having a carboxyl group at the 4-position of the iridoid skeleton as a reaction substrate.
  • an iridoid aglycone having a carboxyl group at position 4 of the iridoid skeleton as a raw material, but i) when using an iridoid compound having an alkyl ester group at position 4 of the iridoid skeleton as a precursor.
  • a methyl ester group is preferable.
  • iridoid glucoside as a precursor ii)
  • ester hydrolysis treatment to position 4 of the iridoid skeleton It is preferable to carry out the reaction of decomposing into carboxyl groups.
  • the ester hydrolysis treatment according to the present invention may be any means involving a reaction of hydrolyzing an alkyl ester group to a carboxyl group at the 4-position of the iridoid skeleton, for example, treatment with an alkaline solution, treatment with an ion exchange resin, Means such as enzyme treatment having esterase activity can be employed.
  • an ester hydrolysis treatment can be carried out by preparing an alkaline solution of about pH 10 to 13 with sodium hydroxide or the like and heating in the solution at about 40 to 70 ° C.
  • the precursor iridoid glucoside is used as a raw material in the method for producing a red pigment composition according to the present invention
  • ii) the iridoid aglycone is formed by hydrolyzing the ⁇ -glycosidic bond at position 1 of the iridoid skeleton It is preferable to carry out the reaction.
  • the hydrolysis treatment of the ⁇ -glycosidic bond may be any means involving a reaction to hydrolyze the ⁇ -glycosidic bond at position 1 of the iridoid skeleton, for example, an enzyme treatment having ⁇ -glucosidase activity, a microorganism having ⁇ -glucosidase activity Means such as treatment or treatment using an acidic solution can be employed.
  • an aglycone production reaction can be carried out by preparing an enzyme solution having ⁇ -glucosidase activity of about pH 3 to 6 and treating it in the solution.
  • the enzyme having ⁇ -glucosidase activity can be used without particular limitation, and for example, cellulase can be used.
  • cellulase T “Amano”
  • cellulase A “Amano”
  • Driselase KSM Multifect A40
  • cellulase GC220 above Genene Core Kyowa Co., Ltd.
  • cellulase GODO-TCL Cellulase GODO TCD-H Besselex
  • Cellulase GODO-ACD manufactured by Kyodo Shuseki Co., Ltd.
  • Cellulase manufactured by Toyobo Co., Ltd.
  • Cellulase Cellulase XL-522
  • Cell soft, Deni Max (more than Novozymes), cellulosin AC40, cellulosin AL, more cellulosin T2 (more than H), cellulase
  • the precursor treatment described in the above i) and ii) is preferably carried out by a treatment method suitable for the substance and composition depending on the kind of the raw material compound and the raw material composition used as the precursor.
  • a treatment method suitable for the substance and composition depending on the kind of the raw material compound and the raw material composition used as the precursor.
  • the compound include geniposide and gardenoside, which are iridoid glycosides having a methyl ester group at the 4-position of the iridoid skeleton.
  • geniposide that is abundantly contained in gardenia fruit is suitable.
  • geniposidic acid which is abundant in gardenia fruit, is suitable.
  • geniposidic acid is a compound obtained by hydrolyzing the methyl ester group at the 4-position of the iridoid skeleton of geniposide, which is abundantly contained in gardenia fruit, to a carboxyl group.
  • iridoid aglycone having an alkyl ester group at the 4-position of the iridoid skeleton When iridoid aglycone having an alkyl ester group at the 4-position of the iridoid skeleton is used as a precursor, the treatment of i) above is necessary.
  • the compound include genipin which is an iridoid aglycone having a methyl ester group at the 4-position of the iridoid skeleton.
  • the content of iridoid glucoside having a methyl ester group at position 4 of the iridoid skeleton corresponding to the precursor is large. It is preferred to carry out both treatments of) and ii) to form iridoid aglycone which is a substrate for red color development.
  • the relationship between the structure of the iridoid compound and the treatment step in the production method according to the present invention is shown in the table with an example of an iridoid compound, i.
  • the method for producing a red dye composition according to the present invention is a method of performing red color development accompanied by the action of an amino group-containing compound on iridoid aglycone having a carboxyl group at the 4-position of the above-described iridoid skeleton.
  • red color development refers to a series of reactions that proceed with the action of the iridoid aglycone and the amino group-containing compound.
  • the action of iridoid aglycone and an amino group-containing compound means that the oxygen atom at position 2 of the iridoid skeleton is substituted by the nitrogen atom derived from the amino group-containing compound, and the amino group-containing compound is bound to the iridoid compound Refers to a complex reaction consisting of a reaction to be conducted and an oxidation polymerization reaction of iridoid compounds (see Japanese Patent Publication No. 55-5778).
  • water is preferably used as a solvent of the solution such as a solvent for performing red color development according to the present invention. More preferably, it is preferable to use purified water, distilled water, ultrapure water or the like, but if it is a grade of water used for food and drink manufacture, pigment preparation and the like, it can be used without problems as the solvent. Further, as the solvent, it is possible to use an aqueous solution containing various salts, organic acids, pH adjusters, pH buffers, lower alcohols and the like, as long as the red coloring is not substantially inhibited.
  • the red color development according to the present invention is carried out under the condition that an organic acid containing ascorbic acid and / or its analogous compound is present as an organic acid in the reaction solution.
  • an organic acid containing ascorbic acid and / or its analogous compound is present as an organic acid in the reaction solution.
  • the structure of the red pigment compound produced and / or the composition of the red pigment composition are changed, and the compositional A bright reddish yellowish tone is imparted to the color tone of the red pigment composition produced by the features. This achieves beautiful color development characteristics with "brightness" in the produced red pigment composition.
  • the red coloration according to the present invention is carried out in a solution containing ascorbic acid, its analogous compound, or two or more compounds selected therefrom as a reaction liquid.
  • ascorbic acid is used as a term referring to L-ascorbic acid in the present specification.
  • ascorbic acid is inexpensive as a raw material.
  • it is a substance that has high water solubility and is easy to handle with regard to handling in manufacturing processes such as addition.
  • as ascorbic acid in this specification the thing of the ion state at the time of melt
  • L-ascorbic acid which is ascorbic acid, but it is also possible to use similar compounds.
  • an analogue thereof refers to an analogue of ascorbic acid and which exhibits a brightening property equal to or higher than that of ascorbic acid when used in this step.
  • Analogues of ascorbic acid include optical isomers and stereoisomers of L-ascorbic acid.
  • an optical isomer D-xyloascorbic acid can be mentioned.
  • alaboisoascorbic acid can be mentioned, and erythorbic acid which is D-araboisoascorbic acid is also included in the stereoisomer.
  • a derivative of ascorbic acid or a derivative of an isomer thereof is also included.
  • the derivative refers to a compound or the like in which a functional group is substituted while maintaining the basic skeleton structure of ascorbic acid or an isomer thereof, and among them, when used in this step, it is compared with ascorbic acid. It is possible to use any compound which exerts no reddening effect or an equal or more brightening effect.
  • examples of compounds similar to ascorbic acid also include compounds such as salts of ascorbic acid, compounds such as salts of the compounds exemplified above, and the like.
  • an ascorbic acid analogue compound the thing of the ion state at the time of melt
  • the amount of ascorbic acid and / or its analog compound to be contained in the reaction solution in the red color development according to the present invention needs to be larger than the amount usually expected to the iridoid compound contained in the reaction solution. is there.
  • the presence of ascorbic acid and / or a similar compound thereof in a certain amount or more in the reaction solution realizes color development characteristics with "brightness" in the produced red pigment composition.
  • the blending amount of ascorbic acid and / or its analog compound to be contained in the reaction liquid is 1 molar equivalent or more to the total molar equivalent of the iridoid compound contained in the reaction liquid. .
  • it is at least 2 molar equivalents, preferably at least 3 molar equivalents, more preferably at least 4 molar equivalents, still more preferably at least 4.5 molar equivalents, particularly preferably 5 molar equivalents relative to the total molar equivalents of the iridoid compound contained in the reaction solution.
  • a molar equivalent of at least 6, more preferably at least 6 molar equivalents, particularly preferably at least 6 molar equivalents is preferred from the viewpoint of imparting the reddishness of the resulting red pigment composition.
  • the upper limit of the blending amount of ascorbic acid and / or its analogous compound is not particularly limited, but, for example, 30 molar equivalents or less, preferably 25 molar equivalents or less, relative to the total molar equivalents of iridoid compounds contained in the reaction solution Preferably, 20 molar equivalents or less can be mentioned.
  • total molar equivalent of the iridoid compound refers to the amount corresponding to the total moles (the total number of moles of all the compounds having an iridoid skeleton) of all the iridoid compounds contained in the reaction solution.
  • molar equivalent to total molar equivalent of iridoid compound indicates a molar ratio to an amount corresponding to the total moles of all iridoid compounds contained in the reaction solution.
  • the composition of the red pigment composition changes, and the compositional feature of the composition imparts to the color tone of the red pigment composition a bright and bright lighted red color tone.
  • the total amount of the organic acids contained in the reaction solution is preferably 4 molar equivalents or more with respect to the total molar equivalents of the iridoid compound contained in the reaction solution. In particular, it is at least 5 molar equivalents, more preferably at least 5.8 molar equivalents, still more preferably at least 6 molar equivalents, still more preferably at least 6 molar equivalents relative to the total molar equivalents of the iridoid compound contained in the reaction solution It is preferable from the viewpoint of imparting the bright redness and lightness of the red dye composition to be produced if it is preferably at least 6.5 molar equivalents, particularly preferably at least 7 molar equivalents.
  • the upper limit of the total amount of organic acids is not particularly limited, but for example, it is 30 molar equivalents or less, preferably 25 molar equivalents or less, more preferably 20 molar equivalents or less based on the total molar equivalents of the iridoid compound contained in the reaction solution. It can be mentioned.
  • the "total amount of organic acid” is indicated in molar equivalents relative to the total molar equivalent of the iridoid compound contained in the reaction solution.
  • the organic compound to be contained in the reaction liquid in the range where i) the blending amount of ascorbic acid and / or its analogous compound and ii) the total amount of organic acids satisfy the above conditions As the acid, an embodiment in which an organic acid other than ascorbic acid and / or its analog compound is contained in the solution can be adopted. That is, in the present invention, in the step of performing red color development described in the above (Step 1), as the organic acid, ascorbic acid, its analogous compounds, or two or more compounds selected therefrom It is possible to adopt an aspect of carrying out with a solution containing an acid.
  • the red pigment composition according to the present invention can be obtained with variations in color tone. It becomes possible to prepare a product. That is, in the present invention, by changing the ratio of the organic acid in the range satisfying the above conditions i) and ii), it is possible to adjust the color tone of the obtained red pigment composition.
  • the “ratio" of ascorbic acid and / or a similar compound thereof to another organic acid it is preferred that the content ratio of ascorbic acid and / or a similar compound to the total amount of organic acids is a certain value or more. Is preferable in terms of beautiful color development characteristics. That is, in the present invention, ascorbic acid, as a molar ratio to the total amount of organic acids (total number of moles of all organic acids) contained in the reaction liquid, in the step of performing red color development described in (Step 1) above.
  • the molar ratio of ascorbic acid and the like to the total amount of organic acids contained in the reaction liquid can be calculated using the molar equivalent to the total molar equivalent of the iridoid compound contained in the reaction liquid as an index.
  • the total molar equivalent of the iridoid compound contained in the reaction liquid is a molar equivalent of ascorbic acid, its analogous compound, or two or more compounds selected therefrom with respect to the total molar equivalent of the iridoid compound contained in the reaction liquid
  • the total amount (unit: molar equivalent) of the organic acid to can be calculated as a denominator.
  • ascorbic acid, its analogous compounds, or two or more compounds selected therefrom are preferably 55% or more, more preferably 60 It is preferable to use a solution containing at least%, more preferably at least 62.5%, particularly preferably at least 70%, more preferably at least 75%.
  • a solution containing at least%, more preferably at least 62.5%, particularly preferably at least 70%, more preferably at least 75% in terms of coexistence of bright red color tone and color tone variation, ascorbic acid, a compound similar thereto, or two or more compounds selected from these as a molar ratio with respect to the total amount of organic acids contained in the reaction liquid. 5 to 95%, preferably 25 to 95%, more preferably 35 to 90%, still more preferably 37.5 to 90%, particularly preferably 40 to 90%, more preferably 50 to 87.5%. Solution can be mentioned suitably.
  • ascorbic acid a compound similar thereto, or a compound selected from these as a molar ratio to the total amount of organic acids contained in the reaction liquid It is suitable to carry out with a solution containing 5% or more, preferably 10% or more, more preferably 12.5% or more of organic acids other than the above compounds.
  • ascorbic acid ascorbic acid, its analogous compounds, or organic acids other than two or more compounds selected therefrom 5 to 90%, preferably 5 to 87.5%, more preferably 5 to 75%, still more preferably 10 to 65%, particularly preferably 10 to 62.5%, more preferably 12.5 to 50.
  • the solution containing at% can be mentioned suitably.
  • organic acid added together with ascorbic acid and / or its analog compound in the red color development of the present invention is an organic acid which realizes the color tone according to the present invention and can impart color variation. If it is, it is possible to use without particular limitation. In addition, it is possible to use an organic acid which achieves the colorability according to the present invention and has no or substantially no influence on the color tone without particular limitation.
  • citric acid, succinic acid, malic acid, lactic acid and tartaric acid can be specifically mentioned as other organic acids which can realize the coloring characteristics of the bright red color tone and can impart color tone variation according to the present invention.
  • Fumaric acid, etc. can be mentioned. It is also possible to adopt these similar compounds.
  • these similar compounds there can be mentioned compounds which exhibit a comparable function to those of these organic acids when used in this step.
  • Examples of these similar compounds include derivatives of the above-described organic acids, isomers of the above-described organic acids, or derivatives of the above-mentioned isomers.
  • compounds such as salts of these compounds and those in an ionic state at the time of dissolution are also included.
  • citric acid, succinic acid, malic acid as the organic acid, in addition to ascorbic acid, its analogous compounds, or two or more compounds selected therefrom. It is possible to carry out in a solution containing lactic acid, tartaric acid, fumaric acid, their analogous compounds, or two or more compounds selected therefrom.
  • another acid is used as citric acid, succinic acid, their analogous compounds, or two or more compounds selected therefrom, it is particularly preferable in combination with ascorbic acid. It is preferable because the color development characteristics can be achieved.
  • the color value of the red pigment composition produced may be improved with respect to the unit weight of the iridoid compound which is the raw material, depending on the kind of the above-mentioned other organic acids to be blended.
  • the color value of the manufactured red pigment composition tends to be high, and the unit weight of the iridoid compound used as the raw material used The amount of color obtained around will improve.
  • the red color development according to the present invention is carried out using iridoid aglycone having a carboxyl group at the 4-position of the iridoid skeleton as a reaction substrate.
  • iridoid aglycone an aglycone such as the geniposide ester hydrolyzate described above (eg, geniposidic acid, etc.), the Gardenoside ester hydrolyzate, etc. can be used.
  • the geniposide ester hydrolyzate aglycone having a carboxyl group at the 4-position of the iridoid skeleton is aglycone and / or geniposidic acid aglycone.
  • the total amount of iridoid compounds contained in the solution is 0.1 to 75% by mass, preferably 0.5 to 50% by mass, based on the total mass of the solution in which the reaction is performed. The amount can be mentioned.
  • the solution may contain a substance derived from a raw material other than the iridoid compound, as long as it does not substantially inhibit red color development.
  • the red color development according to the present invention is a reaction involving the reaction of the amino group-containing compound with the iridoid compound by substitution of the oxygen atom at position 2 of the iridoid skeleton with the nitrogen atom of the amino group of the amino group-containing compound.
  • the amino group-containing compound suitable for the reaction a composition containing an amino acid or an amino acid that is a primary amino group-containing compound can be used.
  • protein hydrolysates, peptides and the like can be used.
  • the protein hydrolyzate for example, hydrolysates of various proteins such as wheat protein, soy protein, milk protein, collagen and the like can be used.
  • amino acids such as glutamic acid, serine, arginine, lysine, aspartic acid and glycine can be used.
  • sodium salts such as sodium glutamate and the like can also be suitably used.
  • the amount of the amino group-containing compound to be contained in the reaction solution is not particularly limited, but in terms of the preferred red color development characteristics, for example, a concentration of 0.7 molar equivalent or more as the amino acid relative to the total molar equivalent of the iridoid compound Is desirable, and it is desirable to add a concentration that results in one or more molar equivalents.
  • the upper limit of the amount of the amino group-containing compound to the total molar equivalent of the iridoid compound is also not particularly limited, but may be, for example, 10 molar equivalents or less, more preferably 8 molar equivalents or less, still more preferably 6 molar equivalents or less.
  • the red coloration according to the present invention is preferably carried out with the reaction solution under an inert gas atmosphere in view of the red coloration characteristics of the produced dye composition.
  • an inert gas which can be used in the present reaction
  • any inert gas which does not substantially inhibit the progress of the present reaction can be used without particular limitation.
  • nitrogen gas, argon gas, helium gas etc. may be used. it can.
  • nitrogen gas or the like is used.
  • the red color development according to the present invention is preferably carried out under acidic conditions in terms of the red color development characteristics of the produced dye composition.
  • the pH condition for red color development is preferably about pH 3 to 6, more preferably about pH 4 to 5.
  • the reaction is carried out at a pH of neutral or alkaline conditions, the resulting pigment composition tends to be bluish and reddish, which is not preferable.
  • a pH adjustment means to acidic conditions the well-known means to mix
  • the reaction solution is acidified by blending the above-mentioned organic acid.
  • pH adjustment means in the usual direction of alkalization may be performed, and it is not particularly limited.
  • blend sodium hydroxide, sodium carbonate, potassium hydroxide, trisodium phosphate etc. can be mentioned.
  • the red color development according to the present invention can be performed at room temperature of about 1 to 30 ° C. or at normal temperature of about 15 to 25 ° C.
  • the heat treatment conditions are 50 ° C. or more, preferably 60 ° C. or more, and more preferably 70 ° C. or more.
  • the upper limit can mention the boiling point of aqueous solution, in the case of the aqueous solution under normal pressure, 100 degrees C or less and 150 degrees C or less are suitable in the aqueous solution under pressure conditions.
  • the temperature is 50 to 150 ° C., preferably 50 to 100 ° C.
  • the reaction time may be an element which is determined according to the temperature conditions and the like, and may be appropriately determined. However, if the reaction temperature is room temperature or normal temperature, it is preferable to perform for several hours to several days.
  • the heating conditions may be, for example, in the range of about 1 minute to 96 hours, preferably about 10 minutes to 72 hours. If the reaction conditions are insufficient due to the combination of the above temperature and / or time, the amount of the red dye compound formed is too small to be suitable. In addition, in the case where the reaction conditions are too excessive due to the combination of the above temperature and / or time, unnecessary decomposition and the like may occur, which is not preferable.
  • the reaction step is performed a plurality of times as desired.
  • an embodiment is also possible in which various compounds and substances to be added to the reaction solution are added in plural times during the reaction.
  • the reaction liquid obtained by the above operation can be used as an iridoid compound-derived red pigment composition, but solid-liquid separation, purification treatment, concentration treatment depending on the application It is desirable to obtain an iridoid compound-derived red pigment composition which is subjected to dilution treatment, pH adjustment, drying treatment, sterilization treatment and the like to obtain a desired quality and / or form.
  • These steps can be appropriately performed not only at the final stage after red color development but also after the above-described respective steps and treatments. Further, it is also possible to perform desired processing in combination, and it is also possible to perform desired processing multiple times.
  • the means for solid-liquid separation in the production process according to the present invention can be performed by a conventional method. For example, filtration, suction filtration, coprecipitation, centrifugation and the like can be performed to remove solids, aggregated insolubles and the like. Moreover, when filtering, it is also suitable to use a filter aid (for example, diatomaceous earth etc.). In addition, it is also possible to perform the said solid-liquid separation process in multiple times as desired.
  • a filter aid for example, diatomaceous earth etc.
  • the purification treatment in the production method according to the present invention can be performed using conventional techniques as long as separation and purification of the dye compound are possible. For example, it can be carried out by adsorption treatment using silica gel, porous ceramic, styrenic or aromatic synthetic resin or the like. Moreover, it can also carry out by the ion exchange process using cationic resin or anionic resin.
  • the membrane separation treatment can be performed using a membrane filter membrane, an ultrafiltration membrane, a reverse osmosis membrane, an electrodialysis membrane, a functional polymer membrane, or the like.
  • a purification means for removing unreacted low molecular weight compounds or decomposition products from the produced red pigment composition.
  • a purification treatment that enables removal of low molecular weight molecules having a molecular weight cut off of 3,000 or less, preferably 2,000 or less.
  • the operation of processing such as concentration, dilution, drying and the like can be carried out by a conventional method.
  • purification treatment can be performed in the same manner as the above paragraph.
  • sterilization can also be performed by a conventional method.
  • means for sterilization include heat treatment, high pressure treatment, high pressure heat treatment, sterilization filter treatment, ultraviolet irradiation treatment, chemical treatment with a sterilizing agent, and the like.
  • sterilization is preferably performed by heat treatment or high-pressure heat treatment.
  • temperature conditions at the time of performing sterilization heating 60 ° C or more, preferably 70 ° C or more, more preferably 80 ° C or more can be mentioned, for example.
  • the upper limit temperature is not particularly limited as long as the stability imparting functional component is not adversely affected, but may be 140 ° C. or less under pressure conditions, 100 ° C. or less under normal pressure, preferably 95 ° C. or less.
  • Ascorbic acid or the like added at the time of red color development in the present invention does not substantially affect the equilibrium state of the reaction and the like. That is, it is recognized that the method for producing the red pigment composition according to the present invention is a technique comparable to the prior art in terms of the production yield with respect to the raw materials.
  • the iridoid compound-derived red pigment composition produced in the production process of the iridoid compound-derived red pigment composition according to the present invention has a beautiful color forming property having both bright redness and lightness. It becomes possible to grant. That is, in the present invention, the iridoid compound-derived red pigment composition produced in the production process of the iridoid compound-derived red pigment composition is characterized in that the iridoid compound-derived red pigment composition produced is brighter and brighter A method is provided to impart chromogenic properties.
  • the ratio of ascorbic acid and / or its similar compound to the total amount of organic acids in the red colored solution, the ratio of other organic acids to the total amount of organic acids, the type and combination of other organic acids By doing this, it is also possible to impart a coloration variation to the produced iridoid compound-derived red pigment composition while having both reddishness and lightness. That is, in the present invention, the iridoid compound-derived red pigment composition produced in the production process of the iridoid compound-derived red pigment composition is characterized in that the iridoid compound-derived red pigment composition produced is brighter and brighter And a method of applying a color tone change.
  • the iridoid compound-derived red pigment composition according to the present invention is a pigment composition provided with the features described below.
  • the point to be emphasized as the characteristics of the red pigment composition according to the present invention is the point of being excellent in bright redness and lightness and bright different from the bluish dark tone of ordinary gardenia red pigment etc. A color development characteristic of bright red tone is realized.
  • the red pigment composition according to the present invention unless it substantially interferes with the function and effect exerted by the technical features according to the present invention, it is excluded that the other features other than the features described below are included. Absent. Further, the technical scope of the present invention is not limited to the embodiment including all the following features except the essential technical features.
  • the iridoid compound-derived red pigment composition according to the present invention comprises the above-mentioned paragraph 1. It is possible to obtain by the manufacturing method as described in.
  • red color development according to the present invention a compound of a dye compound is formed by an overall result of a plurality of reaction systems, but its action mechanism is not completely elucidated, and a compound which realizes red color development The details of the structure and composition are unknown.
  • expensive equipment such as a mass spectrometer is required, which is economical It is difficult to identify the compound structure even if these devices are used.
  • the red pigment composition according to the present invention is a composition comprising a compound obtained by oxidation polymerization of a reaction product of an iridoid aglycone having a carboxyl group at the 4-position of the iridoid skeleton and an amino group-containing composition. That is, the color forming property of the red dye composition according to the present invention is exhibited by a compound obtained by oxidation polymerization of a reaction product of an iridoid aglycone having a carboxyl group at the 4-position of the iridoid skeleton and an amino group-containing composition. .
  • the compound composition constituting the red pigment composition according to the present invention does not necessarily include ascorbic acid and / or a similar compound thereof or another organic acid. That is, the color forming properties of the red pigment composition according to the present invention are not exhibited by the inclusion of the organic acid in the composition produced after red color development, but after the production of the organic acid added in the production process. Even if it is removed from the composition, it does not affect the color development characteristics of the red pigment composition according to the present invention. Further, as the form of the red pigment composition according to the present invention, for example, liquid form, paste form, gel form, semi-solid form, solid form or powder form may be mentioned, but the form is not particularly limited.
  • iridoid compound before the reaction to be a constituent unit of the red pigment compound according to the present invention Mention may be made of the aglycone of the iridoid compounds having a carboxyl group at the 4-position of the iridoid skeleton described in 1.
  • aglycone preferably, geniposide ester hydrolyzate aglycone and / or geniposidic acid aglycone can be mentioned.
  • genipinic acid can be mentioned.
  • the composition characteristic of the composition constitutes a pigment composition exhibiting bright redness and lightness. Specifically, while the iridoid compound-derived red pigment according to the prior art tends to be bluish to exhibit purple or dark red tone, the iridoid compound-derived red pigment composition according to the present invention exhibits a bright and bright red tone. .
  • the iridoid compound-derived red pigment composition according to the present invention is a pigment composition exhibiting a unique bright red tone.
  • the a value and the b value in the Hunter Lab color system be in the following ranges when measured according to the method described below.
  • the iridoid compound-derived red pigment composition according to the present invention has the following features:
  • a 1 and b 1 in the formula respectively indicate the a value and the b value in the Hunter Lab color system in the aqueous solution containing the iridoid compound-derived red pigment composition.
  • a 0 and b 0 respectively indicate the a value and the b value in the aqueous solution prepared in the same manner as described above except that a standard dye is blended instead of the iridoid compound-derived red dye composition.
  • the standard dye is the above-mentioned paragraph 1.
  • a red pigment composition prepared by blending 4.3 molar equivalents of citric acid with respect to the total molar equivalent of the iridoid compound contained in the reaction solution and performing a red color development step can be used as a standard pigment.
  • a dye prepared in the same manner as Sample 1-1 described in Example 1 herein can be used as a standard dye.
  • the value on the right side of the (formula 1) in the present invention is a value indicating that the color tone of the red pigment composition is on the red side and / or the yellow side as compared with the case where only citric acid is used as the prior art. It is.
  • the color tone of the red dye composition produced by the combination of ascorbic acid and / or its analog compound shows a value in which the b value is shifted to the yellow side.
  • the a value indicates a value shifted to the red side.
  • the shift on the yellow side of the b value and / or the shift on the red side of the a value tends to be further intensified.
  • the value of the right side of the (formula 1) in the present invention is preferably 2.5 or more, more preferably 3 or more, still more preferably 3.5 or more, particularly preferably 4 or more, the red color is more vivid It becomes a color tone and is further suitable as a coloring characteristic.
  • the upper limit of the value may be, for example, 30 or less, preferably 20 or less, but the value is not particularly limited.
  • the combination of ascorbic acid and / or a similar compound shows that the color tone of the red dye composition produced is shifted to the yellow side as compared with the case of using other organic acids. It becomes a thing.
  • the b value in the Hunter Lab color system is preferably in the range shown below when measured according to the method described below.
  • the iridoid compound-derived red pigment composition according to the present invention has the following features:
  • the following (formula 2) is satisfied:
  • b 1 in the formula represents the b value in the Hunter Lab color system in the aqueous solution containing the iridoid compound-derived red pigment composition.
  • b c represents the b value in the aqueous solution prepared in the same manner as described above except that a comparative dye was blended instead of the iridoid compound-derived red dye composition.
  • a comparative dye in the aspect which does not use another organic acid together in red color development, the thing similar to the standard dye as described in said (Formula 1) can be used.
  • ascorbic acid and / or a similar compound thereof is mixed with the same molar equivalent of other organic acids in the total amount of organic acids. It is desirable to use a red pigment composition prepared by performing a red color development step as the comparative pigment.
  • blending 8 molar equivalents only with a succinic acid can be made into the comparison pigment.
  • the value on the right side of the (formula 2) in the present invention is a yellow color of the red color tone of the red pigment composition as compared with the case where only citric acid which is the prior art is blended or an equivalent amount of other organic acids. It is a value indicating that the shift to the side is characteristic. Furthermore, in the red color development according to the present invention, the increase of ascorbic acid and / or its analogues tends to further improve the shift to the yellow side of the produced red pigment composition.
  • the value of the right side of the (formula 2) in the present invention is preferably 2 or more, more preferably 3 or more, and particularly preferably 4 or more, the yellowish color becomes bright red and the color tone is further suitable .
  • the upper limit of the value may be, for example, 30 or less, preferably 20 or less, but the value is not particularly limited.
  • the iridoid compound-derived red pigment composition according to the present invention is a pigment composition exhibiting a unique bright red tone.
  • the iridoid compound-derived red pigment composition according to the present invention preferably has an a value and a CHROMA value in the Hunter Lab color system as described below, as measured according to the method described below.
  • the iridoid compound-derived red pigment composition according to the present invention has the following features:
  • a 1 and C 1 in the formula respectively indicate the a value and the CHROMA value in the Hunter Lab color system in the aqueous solution containing the iridoid compound-derived red pigment composition.
  • a 0 and C 0 respectively indicate the a value and the CHROMA value in the aqueous solution prepared in the same manner as described above except that a standard dye is blended instead of the above-mentioned red dye composition derived from the iridoid compound.
  • a standard dye one similar to the standard dye described in the above (formula 1) can be used.
  • a dye prepared in the same manner as Sample 1-1 described in Example 1 herein can be used as a standard dye.
  • the value on the right side of the (formula 3) in the present invention indicates that the color tone of the red dye composition is on the red side and / or the bright side as compared with the case where only citric acid which is the prior art is blended. It is a value.
  • the color tone of the red dye composition produced by the combination of ascorbic acid and / or a similar compound thereof shows a value in which the CHROMA value is shifted to the bright side.
  • the a value indicates a value shifted to the red side.
  • the shift of the CHROMA value on the bright side and / or the shift of the red value on the a value tend to be further enhanced.
  • the value of the right side of the (formula 3) in the present invention is preferably 2.5 or more, more preferably 3 or more, still more preferably 3.5 or more, still more preferably 4 or more, particularly preferably 4.5 or more Particularly preferably, when it is 5 or more, red is a more vivid color tone, which is further preferable as a coloring property.
  • the upper limit of the value may be, for example, 30 or less, preferably 20 or less, but the value is not particularly limited.
  • the iridoid compound-derived red pigment composition according to the present invention is a pigment composition that exhibits excellent color saturation and excellent red coloration.
  • the red dye composition according to the present invention in order to exhibit its bright redness and lightness color forming properties, Hunter, when the red dye composition to be produced is measured according to the method described below, It is preferable that each value in the Lab color system shows the following range.
  • the iridoid compound-derived red pigment composition according to the present invention has the following features:
  • C 1 in the formula represents a CHROMA value in the Hunter Lab color system in the aqueous solution containing the iridoid compound-derived red pigment composition.
  • the standard dye one similar to the standard dye described in the above (formula 1) can be used.
  • a dye prepared in the same manner as Sample 1-1 described in Example 1 herein can be used as a standard dye.
  • the value on the right side of the (formula 4) in the present invention indicates that the saturation of the red dye composition is equivalent or not inferior or greater than that in the case where only citric acid which is the prior art is blended. It is a value shown.
  • the value on the right side of the (formula 4) is preferably 0 or more, more preferably 1 or more, still more preferably 1.5 or more, particularly preferably 2 or more, particularly preferably 3 or more.
  • the saturation is improved to obtain a bright color tone, which is further preferable as a coloring characteristic.
  • the upper limit of the value may be, for example, 30 or less, preferably 25 or less, but the value is not particularly limited.
  • the L value (brightness)
  • the contribution from the improvement of the above-mentioned value is large, but the L value, which indicates the lightness, is also involved as the overall color tone. That is, as the L value in the red pigment composition according to the present invention, an L equivalent to or equivalent to or more than that of the red pigment composition derived from an iridoid compound produced using an organic acid such as citric acid which is the prior art It is preferred that the value is indicated.
  • an iridoid compound origin red pigment composition manufactured using organic acids, such as a citric acid which is prior art the thing similar to the standard pigment
  • it is a pigment composition exhibiting a reddish purple to red color tone at pH 5 and, when expressed by the HUE value (or JIS color name) in the Munsell color system, 5RP (reddish purple) to 10RP (purple red) It is a dye composition exhibiting a color tone of ⁇ 5R (red).
  • the coloring characteristics of the iridoid compound-derived red pigment composition according to the present invention can also be expressed as the ratio of the absorbance at the maximum absorption wavelength to the absorbance at another fixed wavelength.
  • the red pigment composition according to the present invention when the pigment composition-containing aqueous solution is prepared to have a pH of 5 with McIlvaine buffer, 520 to 545 nm, preferably 530 to 542 nm, particularly preferably 534 to It is a dye composition having a maximum absorption wavelength at 538 nm.
  • the red dye composition according to the present invention exhibits coloring characteristics excellent in bright redness at each value of the above-mentioned Hunter Lab color specification system.
  • "bright redness” refers to a color tone exhibiting a bright and bright red color, and indicates high values of a value and / or b value. The higher the a value and / or b value, the brighter the color tone is, and the preferred red pigment composition in terms of bright red coloring characteristics.
  • those having high a and b values are preferable.
  • the b value indicating that it is a yellowish color tone is high, it exhibits a beautiful and bright red color, which is preferable.
  • the higher the CHROMA value the higher the color saturation and the brighter the color tone, which is preferable in terms of bright redness.
  • the red pigment composition according to the present invention a color developing property having brightness excellent in brightness and brightness is shown at each value of the above-mentioned Hunter Lab color system.
  • "brightness” refers to a bright and bright color tone
  • the CHROMA value indicates a high value.
  • the higher the CHROMA value the brighter and brighter the color tone becomes, and the preferred red pigment composition in terms of light-colored color-forming characteristics.
  • the higher the L value the higher the color tone, and the more preferable in lightness.
  • the color forming properties indicated by the above-mentioned formulas for the above-mentioned Hunter Lab color system indicate that the iridoid compound-derived red pigment composition according to the present invention has a color forming property exhibiting bright and clear red color. It can not be realized with red color development in the presence of citric acid alone, which is a technology.
  • the iridoid compound-derived red pigment composition according to the present invention is a pigment composition having high stability to light and heat, and has a characteristic that the color forming property is hardly lost upon light irradiation, heat exposure, and the like.
  • the said degree of stability has high heat resistance and light resistance equivalent to or more than the iridoid compound origin red pigment composition manufactured by citric acid addition which is a prior art.
  • the iridoid compound-derived red pigment composition according to the present invention can be suitably used for coloring distribution products that require resistance to fluorescent lamp irradiation, high temperature storage and the like due to the characteristics relating to the stability. Moreover, it can be suitably used also in the aspect which assumes heat processing, such as retort sterilization, a process, and cooking.
  • gardenia red pigment composition Specific examples of the iridoid compound-derived red pigment composition according to the present invention include a gardenia red pigment composition produced using a gardenia fruit or an extract thereof as a source material of the iridoid compound.
  • the term "gardenia red pigment composition” refers to the above paragraph 1.
  • a pigment composition comprising a red pigment compound produced with the action of an iridoid aglycone having a carboxyl group at the 4-position of the iridoid skeleton derived from a gardenia fruit described in and a composition containing an amino group.
  • the gardenia red pigment composition according to the present invention is a pigment composition including a wider range than the gardenia red pigment composition based on the general definition.
  • the gardenia red pigment composition according to the present invention is manufactured using geniposide and / or geniposidic acid separated or purified from gardenia fruit as a raw material without directly using gardenia fruit or an extract thereof etc. Also included are red pigment compositions. Further included are red pigment compositions prepared using genipin and / or genipinic acid derived therefrom as a raw material.
  • “Hunter Lab color system (Lab system)” is a color system that forms a color solid composed of orthogonal coordinates including a-axis and b-axis indicating chromaticity and an L-axis perpendicular thereto. It is.
  • the “a value” is a value representing the red and green color tones numerically. The larger the value of a, the stronger the red, and the smaller the value of a, the stronger the green.
  • the “b value” is a value representing the yellow and blue tones numerically. The larger the b value, the stronger the yellow color, and the smaller the b value, the stronger the blue color.
  • CHROMA value is a value representing the distance from the origin in the Hunter Lab color system numerically by the following formula (11). Used as a value indicating saturation. The larger the value is, the brighter the color is.
  • color difference ( ⁇ E) is a point at which two colors are plotted in the Hunter Lab color system ((a 1 , b 1 , L 1 ) and (a 2 , b 2 , L 2 ).
  • the distance of the distance between the two is calculated by the following equation (12) and is represented by a numerical value.
  • HUE value refers to a forming angle of a straight line connecting a plot (a value, b value) on the a-axis and b-axis orthogonal coordinates in the Hunter Lab color system and the origin. It is a value representing the hue expressed by converting to the hue notation in. It is a value representing the hue as a symbol and a numerical value.
  • maximum absorption wavelength refers to a light wavelength (nm) at which the absorption in the visible light region of the dye or dye composition becomes maximum.
  • absorption is a value representing the degree to which a substance absorbs light.
  • the absorbance (A ⁇ ) of the maximum absorption wavelength ( ⁇ max) can be determined by the following equation (13). In the formula, A indicates absorbance, ⁇ indicates the maximum absorption wavelength, A ⁇ indicates the absorbance at the maximum absorption wavelength, I indicates the incident light intensity, and I 0 indicates the transmitted light intensity.
  • the "color values” means “color value E 10% 1 cm", the “color value E 10% 1 cm”, when the preparation of the 10 weight% of the dye composition-containing solution, It is a value calculated based on the absorbance (A: Absorbance) of the maximum absorption wavelength ( ⁇ max) in the visible light region using a measurement cell with an optical path length of 1 cm.
  • color value conversion refers to conversion of a dye (dye composition) into a value per color value. For example, when the pigment (pigment composition) is adjusted to have a color value of 60, 0.05 mass% in terms of the color value of 60 means an amount such that the pigment content in the solution is 0.05 mass%. means.
  • McIlvaine (McMilvaine) buffer is a buffer prepared using citric acid and phosphate (Na 2 HPO 4 ), also known as citrate buffer.
  • the iridoid compound-derived red pigment composition according to the present invention differs from the conventional bluish dark color iridoid compound-derived red pigment composition according to the above paragraph 2. It is a pigment composition having the characteristics described in the above, and a red pigment composition excellent in bright redness. In particular, it is a red pigment composition which exhibits beautiful color development characteristics combining reddishness and lightness. Therefore, the red pigment composition according to the present invention can be widely used for applications and products that were difficult to use with the iridoid compound-derived red pigment composition according to the prior art (in particular, the gardenia red pigment). .
  • the iridoid compound-derived red pigment composition according to the present invention can be used as a pigment preparation.
  • the red pigment composition according to the present invention is a gardenia red pigment composition
  • it is suitable to use it as a gardenia red pigment preparation.
  • the form of the pigment preparation according to the present invention may be, for example, liquid, paste, gel, semi-solid, solid, powder and the like, and is not particularly limited.
  • processed solid shapes, such as granular form and a tablet, can be mentioned.
  • the iridoid compound-derived red pigment composition according to the present invention is water-soluble, it can be used as it is as a water-soluble pigment formulation, but it can be used as an oil-soluble pigment formulation (W / O type) or double emulsion It is also possible to process it into a pigment preparation (W / O / W type) or the like and use it.
  • the compounding ratio of the iridoid compound-derived red pigment composition can be appropriately adjusted according to the type and purpose of the pigment preparation, and is not particularly limited. It is suitable to blend so that the 10% 1 cm value becomes 20 or more, preferably 30 or more, more preferably 40 or more.
  • the upper limit of the color value of the dye preparation according to the present invention is not particularly limited, for example, the color value E 10% 1 cm value may be 800 or less.
  • the blending ratio of the iridoid compound-derived red pigment composition in the pigment preparation may be calculated on the basis of the above color value, but as a mass base, for example, 0.1 to 99 mass%, preferably 1 to 90 mass%, more preferably And 5 to 75% by mass can be mentioned.
  • the dye preparation according to the present invention can be blended with other functional components as long as the color development characteristics of the red dye composition according to the present invention are not substantially impaired.
  • the dye preparation according to the present invention can be blended with an additive having a function to stabilize or improve the color development property and the like.
  • antioxidants, pH adjusters, polysaccharide thickeners, and other food materials can be blended.
  • red pigment composition according to the present invention other pigments can be blended as the pigment preparation according to the present invention.
  • the dye preparation according to the present invention can be made into a dye preparation adjusted to a desired color tone by blending the other dyes.
  • natural dyes having a stable coloring characteristic like the red dye composition in the present invention are suitable.
  • natural pigments such as gardenia yellow pigment, gardenia blue pigment, safflower pigment, anthocyanin pigment, bilberry pigment, turmeric pigment, tamarind pigment, oyster pigment, caramel pigment, spirulina pigment, kolyan pigment, cochineal pigment, tomato pigment etc. Although it can mention, it is not restricted in particular in these.
  • the red pigment composition or the pigment preparation according to the present invention can be suitably used for a use as a coloring agent using an iridoid compound-derived red pigment composition according to the prior art, in addition to the prior art iridoid compound Products which were difficult to use in terms of color tone with the derived red pigment composition (especially gardenia red pigment) can be used in a wide range of fields.
  • the red pigment composition or pigment preparation according to the present invention can be suitably used as a natural coloring agent for products such as food and drink, cosmetics, medicines, quasi drugs, daily goods for hygiene, or feeds. It is. That is, in the present invention, it is possible to provide a food or drink, a cosmetic, a medicine, a quasi-drug, a daily product for hygiene, or a feed containing the red pigment composition or pigment preparation according to the present invention.
  • a product example which can be colored with the red pigment composition or pigment preparation concerning the present invention is shown below, it is not limited as these as a colorable product concerning the present invention.
  • “food and drink” examples include beverages, frozen desserts, desserts, sugar confectionery (eg, candy, gummy, marshmallow), gum, chocolate, confectionery (eg, cookies etc.), bread making, agricultural products (eg, pickles etc.) Processed meat products, processed fish products, dairy products, noodles, seasonings, jellies, syrups, jams, sauces, liquors and the like.
  • “Cosmetics” may include skin lotions, lipsticks, sunscreen cosmetics, makeup cosmetics, and the like.
  • “Pharmaceutical” can include various tablets, capsules, drinks, troches, and mouthwashes.
  • Examples of “quasi-drugs” include nutritional aids, various supplements, dentifrices, mouth fresheners, odor preventives, hair nourishing agents, hair restorers, skin moisturizers, and the like.
  • Examples of “daily hygiene products” include soaps, detergents, shampoos, rinses, hair treatments, toothpastes, bath agents, and the like.
  • Examples of the "feed” include various pet foods such as cat food and dog food; food for ornamental fish and cultured fish; and the like.
  • the dye composition or dye preparation according to the present invention has a color forming property excellent in red and bright color tone, and in particular, it is based on milky white which tends to be a dull color which is difficult to use with conventional gardenia red pigment etc. It is possible to color the material to be a color tone with a bright red color tone. For example, it is possible to use suitably also for coloring of a milk beverage, a dairy product, a fish meat processed product etc. Similarly, it is possible to color bright red tones even for beverage products that are difficult to use with conventional gardenia red pigments. For example, it is possible to use suitably also to a soft drink which has transparency, liquor, etc.
  • the pigment composition or pigment preparation according to the present invention is a technique characterized by the addition of an organic acid such as ascorbic acid, and thus is a suitable technique from the viewpoint of safety, and it can be taken into the human body. It is suitable for use in coloring applications for target products. In particular, it is suitable for use in coloring applications such as food and drink.
  • the dye composition or the dye preparation according to the present invention has excellent light resistance and heat resistance which are the features of the iridoid compound-derived red dye composition. Therefore, it is possible to use suitably also to coloring of a product etc. which assumed exposure to light in storage, a display, etc. It can also be used for products that are expected to be exposed to high temperature storage.
  • the dye composition or dye preparation according to the present invention can be suitably used for coloring use in the production process of the above-mentioned product.
  • a process of coloring the above-mentioned product it is possible to carry out according to the means of the usual method in each product except blending the pigment composition or pigment preparation concerning the present invention as a natural pigment.
  • a compounding ratio of the red pigment composition or pigment formulation which concerns on this invention with respect to these products it is possible to adjust suitably according to the kind and objective of products.
  • the content of the dye composition in the product is 0.001 to 1% by mass, preferably 0.005 to 0.5% by mass, more preferably 0.01 to 0.2% by mass, in terms of color value 80. More preferably, it is possible to blend so as to be 0.02 to 0.1% by mass.
  • the present invention includes a step of containing or compounding the iridoid compound-derived red pigment composition obtained by the production method described in the above paragraph, pigment preparation, food and drink, cosmetics, and pharmaceuticals
  • the present invention includes a method for producing quasi-drugs, daily products for hygiene, or feed.
  • the feature, the process, etc. which were described in the said paragraph can be referred or referred and used.
  • the content or blending amount of the above-mentioned iridoid compound-derived red pigment composition it is possible to refer to or cite the description of the above paragraph regarding the pigment preparation and each product.
  • the red pigment composition or the pigment preparation according to the present invention can be colored in a bright and bright red color tone in a product manufactured by blending the same, yet another excellent effect and effect depending on the product to be colored May be played.
  • the effects include various effects such as secondary effects of the above-mentioned effects and effects of foreign substances.
  • the raw material which is the product to be colored in pink tone
  • the raw material is a product having a white color
  • an ordinary gardenia red pigment when used, it tends to be dark blue due to the color tone when it is mixed with the raw material It was difficult to express the shade in bright pink etc.
  • the red pigment composition or pigment preparation according to the present invention when coloring is performed using the red pigment composition or pigment preparation according to the present invention, the bright "pink" is obtained even when the raw material etc. becomes a mixed color tone with a product having a white color system. Color development is possible. In addition, it is also possible to develop a color tone that impresses strawberry, which is difficult with ordinary gardenia red pigment.
  • products suitable for coloring in a pinkish color tone in the present invention for example, bread, gum, pudding, bavaroa, strawberry milk, various dairy products, candy, flower paste, cream, cookie, donut, cake, biscuit, syrup , Jam etc. can be mentioned. Moreover, even if it is products other than these, if it can generally be recognized equivalent to these products, it will be recognized as what is contained in the said products. In the present invention, since dark blue coloration caused by mixing with a white-based material is suppressed, it is possible to color a product having a white-based material in a bright pink color with respect to a product having a white-based material.
  • the main steps in the process for producing the iridoid compound-derived red pigment composition according to this example are shown as a flow chart in FIG.
  • the description "GP to molar equivalent” is a value indicating the addition amount or content of the compound used in the production process of the gardenia red pigment composition in terms of the molar ratio to the raw material, geniposide. .
  • “*” indicates that the product is a product of San-Ei Gen F.F.I.
  • “*” indicates a registered trademark of San-Ei Gen F.F.
  • a solution of pH 12 was prepared by adding 2.25 g of a 48% sodium hydroxide solution to 11 g of an aqueous solution containing 32% of purified geniposide (hereinafter sometimes abbreviated as GP) to prepare a solution of pH 12, and the solution was hydrolyzed to 30 mL.
  • the ester hydrolysis treatment was carried out by stirring at 50 ° C. for 2 hours to form geniposidic acid.
  • 6.6 g (GP to 4.3 molar equivalent) of sodium glutamate was added, and various organic acids shown in Table 2 were added as organic acids to adjust the pH value to about 4.4 to 4.6.
  • the acid adjusted solution was mixed with 0.6 g of cellulase under a nitrogen atmosphere and gently stirred, and subjected to ⁇ -glucosidase reaction at 50 ° C. for 24 hours to generate genipic acid, which is a geniposidic aglycone.
  • the pH was readjusted to about 4.5, and heat treatment was performed at 80 ° C. for 5 hours to promote the reaction with the amino group-containing compound and the oxidative polymerization reaction of the iridoid compound, thereby promoting red color development.
  • the red coloration in the present example is a reaction which is initiated with the produced aglycone as a substrate even during the ⁇ -glucosidase reaction, but is a reaction which rapidly progresses due to the subsequent heat treatment.
  • Example 1 After cooling to room temperature, 1 part by mass of diatomaceous earth, which is a filter aid, is added to and mixed with liquid volume, and the filter paper (NO. 2 filter, ⁇ 150 mm, Advantech Toyo Co., Ltd.) The filtrate was collected by suction filtration with using the above solution to obtain a gardenia red pigment composition solution.
  • the comparative sample (sample 1-1) prepared in the same manner as the target sample in the above steps was also used as a standard sample in the present example and other examples.
  • the a value becomes red as the addition amount of ascorbic acid increases. It showed a tendency to shift largely to the side, and a tendency to further intensify the red tone (see FIG. 2 showing the result of the two-dimensional plot).
  • the L value and the CHROMA value also tended to increase, and as the addition amount of ascorbic acid was increased, the reddishness and lightness were improved. In particular, the increase in the CHROMA value was remarkable.
  • the color tone of the red pigment composition achieved by the addition of ascorbic acid was a sufficiently bright red color even with GP to 4 molar equivalents, but in particular more than 5 molar equivalents of GP versus more particularly GP relative to 6 molar equivalents.
  • ascorbic acid was added, it was possible to realize a more vivid red color tone.
  • a bright and bright red color tone was confirmed in these red pigment compositions (Samples 1-3 to 1-5).
  • the maximum absorption wavelength ( ⁇ max) is 533 nm for the coloration red pigment composition (Sample 1-1) colored by adding citric acid to red color, and the color redia red pigmented by adding ascorbic acid
  • the compositions (Samples 1-2 to 1-5) showed 534 to 536 nm.
  • a solution of pH 12 was prepared by adding 2.25 g of a 48% sodium hydroxide solution to 11 g of an aqueous solution containing 32% of purified geniposide (hereinafter sometimes abbreviated as GP) to prepare a solution of pH 12, and the solution was hydrolyzed to 30 mL.
  • the ester hydrolysis treatment was carried out by stirring at 50 ° C. for 2 hours to form geniposidic acid.
  • 6.6 g (GP: 4.3 molar equivalents) of sodium glutamate was added, and various organic acids shown in Table 3 were added as organic acids to adjust the pH value to about 4.4 to 4.6.
  • ⁇ -glucosidase reaction 0.6 g was added under nitrogen atmosphere and gently stirred to perform ⁇ -glucosidase reaction at 50 ° C. for 24 hours to generate genipinic acid, which is a geniposidic aglycone.
  • the pH was readjusted to about 4.5, and heat treatment was performed at 80 ° C. for 5 hours to promote the reaction with the amino group-containing compound and the oxidative polymerization reaction of the iridoid compound, thereby promoting red color development.
  • the red coloration in the present example is a reaction which is initiated with the produced aglycone as a substrate even during the ⁇ -glucosidase reaction, but is a reaction which rapidly progresses due to the subsequent heat treatment.
  • the b value showed a tendency to shift to the yellow side as the addition amount of ascorbic acid increased, and the a value also showed a tendency to shift to the red side, and the red color tone tended to be further enhanced ( See Figure 4 which shows the results of a two dimensional plot).
  • the CHROMA value showed a tendency to rise with the increase of the addition amount of ascorbic acid, and the result that the lightness was improved was shown.
  • the bright and bright red color tone exhibited by these red pigment compositions (Sample 2-2 to Sample 2-5) was confirmed.
  • the red pigment composition obtained by adding citric acid together with ascorbic acid to perform red coloration is a prior art. It was shown that a red pigment composition excellent in bright redness and lightness having a color tone shifted to the yellowish side can be prepared unlike the red pigment composition when only citric acid is used. That is, it was shown that the action which ascorbic acid gives to color tone in the said manufacturing process is an action exhibited also under the conditions which other organic acids coexist.
  • At least the addition amount of ascorbic acid is at least 4.3 molar equivalents with respect to GP and the ascorbic acid relative to the total organic acid addition amount (at least 5.8 molar equivalents with GP).
  • the molar ratio was 74.1% or more, it was shown that a red pigment composition excellent in bright redness and lightness could be prepared.
  • the amount of ascorbic acid added is at least 6 molar equivalents of GP and the molar ratio of ascorbic acid to the total amount of added organic acids (GP at least 7.5 molar equivalents) is at least 80%, bright redness and bright It was shown that the colorability was further improved.
  • the test is conducted by making the total amount of the organic acid to be added constant at 8 molar equivalents with respect to GP, so the phenomenon of redness of the color tone of the red pigment composition obtained after the reaction It was confirmed that the action was not due to the use of ascorbic acid.
  • the increase of the CHROMA value showing the saturation was a value which increased in correlation with the total amount of the organic acid added at the time of the reaction.
  • the color development characteristics of the red pigment composition according to the present invention with respect to the reddishness and lightness are i) imparting of a vivid red tone with a yellowish color by the presence of a certain amount or more of ascorbic acid in the reaction solution It has been suggested that it is realized that the provision of a bright and clear color tone is realized by the fact that the total amount of the organic acid is more than a certain amount.
  • the color tone adjustment of the red pigment composition obtained is possible by changing the ratio with the other organic acid added with ascorbic acid in the range which satisfy
  • Sample 4-1 Sample 4-1 4-2: Sample 4-2 4-3: Sample 4-3 4-4: Sample 4-4 4-5: Sample 4-5 4-6: Sample 4-6 4-7: Sample 4-7 4-8: Sample 4-8

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Abstract

Le problème à la base de la présente invention concerne une technique qui concerne la production d'une composition de pigment rouge dérivé d'un composé iridoïde et qui est avantageuse du point de vue de la sécurité de la composition de pigment produite et qui permet de produire une composition de pigment rouge qui est non seulement améliorée en termes de clarté de couleur mais qui peut également présenter une teinte pourvue à la fois d'un rouge brillant et d'une clarté acceptable dans divers domaines comprenant un produit lacté, une boisson et similaire. La présente invention concerne un procédé de production d'une composition de pigment rouge dérivé d'un composé iridoïde, le procédé étant caractérisé en ce qu'il comprend une étape de soumission d'une solution, qui contient un acide organique comprenant de l'acide ascorbique, un composé analogue à l'acide ascorbique ou au moins deux composés choisis parmi l'acide ascorbique et le composé en une quantité totale de 4 équivalents molaires ou plus par rapport à l'équivalent molaire total d'un composé iridoïde, à un développement de couleur rouge associé à la réaction entre un aglycone d'iridoïde présentant un groupe carboxyle en position 4 dans un squelette iridoïde et un composé contenant un groupe amino, ce qui permet de produire un composé de pigment rouge présentant une propriété de développer une couleur pourvue à la fois d'un rouge brillant et d'une clarté.
PCT/JP2018/044449 2017-12-05 2018-12-04 Composition de pigment rouge dérivé d'un composé iridoïde et procédé pour sa production WO2019111861A1 (fr)

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Citations (8)

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Publication number Priority date Publication date Assignee Title
JPS555778B2 (fr) * 1977-12-15 1980-02-09
JPH03277663A (ja) * 1990-03-27 1991-12-09 Taito Kk 明色化した赤色色素の製造方法
JPH0499467A (ja) * 1990-08-16 1992-03-31 House Food Ind Co Ltd イチゴ染色剤及びイチゴの染色方法
JPH0559296A (ja) * 1991-09-03 1993-03-09 Taito Kk クチナシ赤色系色素の製造方法
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
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
JP2012116925A (ja) * 2010-11-30 2012-06-21 Mitsui Sugar Co Ltd 赤色素の製造方法および当該赤色素を含む飲食品
WO2017217527A1 (fr) * 2016-06-17 2017-12-21 三栄源エフ・エフ・アイ株式会社 Composition de colorant rouge dérivé d'un composé iridoïde et son procédé de production

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS555778B2 (fr) * 1977-12-15 1980-02-09
JPH03277663A (ja) * 1990-03-27 1991-12-09 Taito Kk 明色化した赤色色素の製造方法
JPH0499467A (ja) * 1990-08-16 1992-03-31 House Food Ind Co Ltd イチゴ染色剤及びイチゴの染色方法
JPH0559296A (ja) * 1991-09-03 1993-03-09 Taito Kk クチナシ赤色系色素の製造方法
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
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
JP2012116925A (ja) * 2010-11-30 2012-06-21 Mitsui Sugar Co Ltd 赤色素の製造方法および当該赤色素を含む飲食品
WO2017217527A1 (fr) * 2016-06-17 2017-12-21 三栄源エフ・エフ・アイ株式会社 Composition de colorant rouge dérivé d'un composé iridoïde et son procédé de production

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Title
MORITOME, NOBUHARU ET AL., JOURNAL OF FOOD SCIENCE AND TECHNOLOGY, vol. 37, no. 2, 2000, pages 139 - 143 *
TAKAOKA, AKIRA ET AL.: "Dyeing with Plant Pigments: Dyeing with the Extracts of Saffron and Gardenia", JOURNAL OF HOME ECONOMICS OF JAPAN, vol. 43, no. 4, 1992, pages 303 - 309 *

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