JP5355906B2 - Deodorizing Convolvuleaceae Ipomoea genus plant pigment - Google Patents

Description

  The present invention relates to a plant pigment belonging to the genus Ipomoea belonging to the family Convolvulaceae having a slight odor and a slight reduction in odor, and a pigment preparation containing the pigment. Furthermore, the present invention provides a plant pigment belonging to the genus Ipomoea belonging to the genus Convolvulaceae belonging to the genus Convolvulaceae, in which the expression of odor over time that can be caused by long-term storage or the effect of light or heat is significantly suppressed, and a pigment containing the pigment Relates to the formulation. The present invention also relates to a method for producing a plant pigment belonging to the genus Ipomoea belonging to the family of Convolvulaceae having no odor or slight odor.

  Plant pigments belonging to the genus Ipomoea of the family Convolvulaceae that are anthocyanin pigments are pigments that are widely used mainly for coloring foods such as beverages. However, plant pigments belonging to the genus Ipomoea belonging to the family Convolvulaceae have a unique vegetable odor due to the plants belonging to the genus Ipomoea belonging to the family Convolvulaceae. For this reason, when using for products, such as a foodstuff and cosmetics, for example, the smell and fragrance may have a bad influence on the flavor, taste, or fragrance of these products. Moreover, the plant pigment preparation belonging to the genus Ipomoea belonging to the conventional Convolvulaceae family has been pointed out a problem that a so-called `` odor return phenomenon '' occurs, in which aroma develops and gradually becomes odor by heating and long-term storage, The problem of “scent return phenomenon” caused by various processes has not yet been solved.

  The present invention is a plant pigment preparation belonging to the genus Ipomoea belonging to the family Convolvulaceae that can be used safely in these products without affecting the flavor and flavor of various products such as foods, pharmaceuticals, quasi drugs or cosmetics over the long term Is intended to provide. Specifically, the present invention firstly provides a plant pigment belonging to the genus Convolvulaceae belonging to the genus Ipomoea, which has no odor derived from a plant belonging to the genus Convolvulaceae belonging to the genus Ipomoea or whose odor is significantly reduced, and the pigment. It aims at providing the pigment | dye formulation which contains. Secondly, the present invention provides a plant pigment belonging to the genus Ipomoea belonging to the family Convolvulaceae belonging to the genus Ipomoea, which does not change over time such as a so-called “odor return phenomenon” even when heated or stored for a long period of time, and a pigment preparation containing the pigment With the goal. Thirdly, an object of the present invention is to provide a method for producing a plant pigment belonging to the genus Ipomoea belonging to the above-mentioned odorless or slightly odorous Convolvulaceae family.

  The inventors of the present invention have intensively studied to solve the conventional problems related to plant pigment preparations belonging to the genus Ipomoea belonging to the family Convolvulaceae, specifically, the method of the present invention, specifically, the plant pigments belonging to the genus Ipomoea belonging to the family Convolvulaceae. By performing at least one treatment selected from the group consisting of adsorption treatment, ion exchange treatment, acid treatment and membrane separation treatment on the adsorption treatment solution of the extract, malodor contained in plants belonging to the genus Ipomoea belonging to the family Convolvulaceae It was found that odorous components that cause odors and odors can be removed significantly, and plant pigments belonging to the genus Ipomoea belonging to the family of Convolvulaceae with no odor or slight odor can be prepared. Further, it was found that the plant pigments belonging to the genus Ipomoea belonging to the family Convolvulaceae obtained in this way do not cause the “odor return phenomenon” even by heating or long-term storage. Based on these findings, it was confirmed that a plant pigment preparation belonging to the genus Ipomoea belonging to the genus Convolvulaceae belonging to the genus Ipomoea belonging to the genus Convolvulaceae belonging to the genus Ipomoea belonging to the genus Convolvulaceae belonging to the genus Convolvulaceae was excellent. The present invention has been completed based on this finding.

That is, the present invention is a plant pigment belonging to the genus Ipomoea belonging to the family Convolvulaceae listed in the following (1) to (3):
(1). Color value is E ^10% _1cm = 160
In this case, a plant pigment belonging to the genus Ipomoea belonging to the family Convolvulaceae, whose concentration of aroma components is 150 ppm or less.
(2). The aroma component is 2-methylbutanol, isoamyl alcohol, tridecane, ethyl lactate, hexanol, trans-linalool oxide, benzyl alcohol, phenethyl alcohol, 5-methylthiopentanenitrile, phenylpropanenitrile, ethyl-2-hydroxy-3-phenyl Propane, dimethyl phthalate, dihydroactinidiolide, 4-vinylphenol, triethyl citrate, dibutyl phthalate, 4-vinyl-2,6-dimethoxyphenol, phenylacetic acid, ethyl vanillate, 4-ethylcatechol, limonene, cis-pinane , Α-terpineol, N-nitrosodibutylamine, guaiacol, 3,7-dimethyloct-1-ene-3,7-diol, 3-hydroxy-α-pyrone, phenol, γ-nonalacto A plant pigment belonging to the genus Ipomoea belonging to the family Convolvulaceae according to (1), which is any one selected from the group consisting of 4-vinylguaiacol, vanillin, dibutylphthalate and acetic acid.
(3). The plant pigment according to (1) or (2), wherein the plant belonging to the genus Ipomoea belonging to the family Convolvulaceae is Ipomoea Batatas.

Furthermore, this invention is a pigment | dye formulation containing the plant pigment which belongs to the Convolvulaceae family Ipomoea genus as described in said (1)-(3). Examples of such an embodiment include the following (4) and (5).
(4). A plant pigment preparation belonging to the genus Ipomoea belonging to the Convolvulaceae family in the form of a solution.
(5). The plant pigment preparation according to (4), comprising a plant pigment belonging to the genus Ipomoea belonging to the family Convolvulaceae in a proportion of 1 to 90% by weight.

The present invention also relates to a method for producing the highly purified plant pigment belonging to the genus Ipomoea belonging to the above-mentioned highly purified Convolvulaceae family, which is listed in the following (6) to (19):
(6). It is characterized by performing at least one treatment selected from the group consisting of adsorption treatment, ion exchange treatment, acid treatment and membrane separation treatment on the adsorption treatment solution of the plant pigment extract belonging to the genus Ipomoea belonging to the family Convolvulaceae, A method for producing a plant pigment belonging to the genus Ipomoea of the Convolvulaceae family with no odor or slight odor.
(7). Extract of plant pigment belonging to the genus Convolvulaceae Ipomoea is extracted while chopping plants belonging to the genus Convolvulaceae genus Ipomoea in an acidic extraction solvent, or immerse and extract a chopped product of the plant in an acidic extraction solvent The method for producing a plant pigment according to (6), which is obtained by this method.
(8). The method for producing a plant pigment according to (7), wherein the acidic extraction solvent has a pH of 1 to 4.
(9). The method for producing a plant pigment according to (7), wherein the plant pigment extract is obtained by immersing a plant belonging to the genus Ipomoea belonging to the family Convolvulaceae in an acidic extraction solvent, and then performing a heat treatment.
(10). The method for producing a plant pigment belonging to the genus Ipomoea belonging to the family Convolvulaceae according to (6), wherein the acid treatment is treatment using an acid used as a food additive.
(11). The method for producing a plant pigment according to (6), wherein the acid treatment is treatment using at least one inorganic acid selected from the group consisting of sulfuric acid, hydrochloric acid, phosphoric acid and nitric acid.
(12). Acid treatment consists of exposing the treatment solution after adsorption treatment, ion exchange treatment, acid treatment, extraction treatment or membrane separation treatment of plant pigment extract belonging to the genus Ipomoea belonging to the family Convolvulaceae, to pH 1-4 conditions The method for producing a plant pigment according to (6), wherein
(13). The membrane separation treatment is at least one treatment selected from the group consisting of membrane filter membrane treatment, ultrafiltration membrane treatment, reverse osmosis membrane treatment, electrodialysis membrane treatment, ion sorting membrane treatment, and ion exchange membrane treatment. 6) A method for producing a plant pigment belonging to the genus Ipomoea of the family Convolvulaceae as described above.
(14). A method for producing a plant pigment belonging to the genus Ipomoea belonging to the genus Convolvulaceae belonging to the genus Convolvulaceae belonging to the genus Convolvulaceae belonging to the genus Ipomoea, which comprises subjecting the adsorption treatment liquid of the plant pigment extract belonging to the genus Ipomoea belonging to the Convolvulaceae family to deproteinization.
(15). The method for producing a plant pigment according to (14), wherein the membrane separation treatment is any one of a reverse osmosis membrane treatment and an ultrafiltration membrane treatment.
(16). The method for producing a plant pigment according to (14) or (15), wherein the membrane separation treatment is a treatment using a membrane having a fractional molecular weight of 2000 to 4000.
(17). The method for producing a plant pigment according to (14), wherein the deproteinization treatment is at least one treatment selected from the group consisting of ion exchange treatment, extraction treatment, membrane separation treatment, and gel filtration treatment.
(18). The method for producing a plant pigment according to (17), wherein the membrane separation treatment used as the deproteinization treatment is treatment using a membrane having a fractional molecular weight of 10 ⁴ to 10 ⁶ .
(19). The method for producing a plant pigment according to (14), wherein the acid treatment is performed before the membrane separation treatment.

  It has no odor derived from plants belonging to the genus Ipomoea of the Convolvulaceae family, or the odor is significantly reduced, and it is excellent in stability without change over time such as so-called `` odor return phenomenon '' caused by heating and long-term storage It is possible to provide plant pigments belonging to the genus Ipomoea belonging to the family Convolvulaceae, and pigment preparations containing the pigments, and consequently affect the flavor and flavor of various products such as foods, pharmaceuticals, quasi drugs or cosmetics over a long period of time. It is possible to color the food, medicine, quasi-drug, or cosmetic without giving the color.

  The present invention is a plant pigment belonging to the genus Convolvulaceae belonging to the genus Convolvulaceae belonging to the genus Convolvulaceae belonging to the genus Convolvulaceae belonging to the genus Convolvulaceae belonging to the genus Convolvulaceae belonging to the genus Convolvulaceae. In the present invention, the plant pigment belonging to the genus Convolvulaceae Ipomoea broadly means pigments obtained from plants of the genus Convolvulaceae Ipomoea, and the plants include Ipomoea Batatas, Ipomoea nil, Ipomoea congesta, Ipomoea alba Etc. An anthocyanin pigment derived from Ipomoea Batatas is preferable, and a red pigment and a reddish purple pigment containing the anthocyanin pigment are also included in the pigment.

In the present invention, the color value “E ^10% _{1 cm} ” means the absorbance at the maximum absorption wavelength (near 530 nm) in the visible part of a solution containing the plant pigment belonging to the genus Ipomoea of the Convolvulaceae family (buffer solution pH 3.0). (Measurement cell width: 1 cm), and the absorbance is a numerical value converted into the absorbance of a plant pigment-containing solution belonging to the genus Ipomoea belonging to the 10 w / v% Convolvulaceae family.

  In the present invention, the fragrance component means various fragrance components contained in plants belonging to the genus Ipomoea belonging to the family Convolvulaceae, and in particular, fragrance components that cause malodor and odor. Specifically, 2-methylbutanol, isoamyl alcohol, tridecane, ethyl lactate, hexanol, trans-linalool oxide, benzyl alcohol, phenethyl alcohol, 5-methylthiopentanenitrile, phenylpropanenitrile, ethyl-2-hydroxy-3-phenylpropane , Dimethyl phthalate, dihydroactinidiolide, 4-vinylphenol, triethyl citrate, dibutyl phthalate, 4-vinyl-2,6-dimethoxyphenol, phenylacetic acid, ethyl vanillate, 4-ethylcatechol, limonene, cis-pinane, α-terpineol, N-nitrosodibutylamine, guaiacol, 3,7-dimethyloct-1-ene-3,7-diol, 3-hydroxy-α-pyrone, phenol, γ-nonalactone, 4 -Vinyl guaiacol, vanillin, dibutyl phthalate, acetic acid and the like.

The plant pigment belonging to the genus Ipomoea belonging to the family Convolvulaceae of the present invention, when the color value of the pigment is adjusted to E ^10% _{1 cm} = 160, the total concentration of the fragrance components contained in the pigment is 150 ppm or less, Preferably it is 100 ppm or less, More preferably, it is 80 ppm or less. The concentration of the aroma component is approximately proportional to the color value. Therefore, plant pigments belonging to the genus Ipomoea belonging to the family Convolvulaceae targeted by the present invention are only required to have a total concentration of aroma components in the above range when the pigment is adjusted to the above color value, and the pigment itself is the above color value. There is no need to have.

  The plant pigment belonging to the genus Convolvulaceae family Ipomoea of the present invention, the content of the aroma component is extremely reduced, non-brominated or slightly brominated, is adsorbed to the adsorption treatment liquid of the plant pigment extract belonging to the genus Convolvulaceae family Ipomoea It can be produced and obtained by performing any one of treatment, ion exchange treatment, acid treatment, extraction treatment or membrane separation treatment, or any combination of these treatments.

  Therefore, the present invention provides a method for producing the odorless or slightly brominated plant pigment belonging to the genus Ipomoea (Deodorized Convolvulaceae family Ipomoea). The production method of the present invention, from another point of view, is a causative component of off-flavor or malodor contained in a pigment extract of a plant belonging to the genus Ipomoea belonging to the family Convolvulaceae, 2-methylbutanol, isoamyl alcohol, tridecane, ethyl lactate, hexanol , Trans-linalool oxide, benzyl alcohol, phenethyl alcohol, 5-methylthiopentanenitrile, phenylpropanenitrile, ethyl-2-hydroxy-3-phenylpropane, dimethylphthalate, dihydroactinidiolide, 4-vinylphenol, triethyl citrate, Dibutyl phthalate, 4-vinyl-2,6-dimethoxyphenol, phenylacetic acid, ethyl vanillate, 4-ethylcatechol, limonene, cis-pinane, α-terpineol, N-nitrosodibutylamine, guaiaco , 3,7-dimethyloct-1-ene-3,7-diol, 3-hydroxy-α-pyrone, phenol, γ-nonalactone, 4-vinyl guaiacol, vanillin, dibutyl phthalate and acetic acid It can be said that this is a method for purifying plant pigments belonging to the genus Ipomoea belonging to the family Convolvulaceae. Moreover, it can be said that the manufacturing method of the present invention is a method for deodorizing plant pigments belonging to the genus Ipomoea belonging to the family Convolvulaceae from another viewpoint.

  As the pigment extract of plants belonging to the genus Ipomoea belonging to the family Convolvulaceae used in the production method of the present invention, solvent extracts of the plant bodies belonging to the genus Ipomoea belonging to the family Convolvulaceae mentioned above are used. The plant part used for extraction may be a part containing an intended pigment, particularly an anthocyanin pigment, and includes an anthocyanin pigment among roots, stems, leaves, fruits (seed), petals, flower buds, and the like. Sites can be used. The plant body includes callus of plants belonging to the genus Ipomoea belonging to the family Convolvulaceae. The part containing the pigment of the plant may be subjected to an extraction operation as it is (raw) or as a crushed product (crude powder, shredded product, etc.), and after drying, a crushed product (powder product) as necessary. Etc.) may be applied to the extraction operation.

  Although it does not restrict | limit especially as a solvent used for the said extraction, Alcohol, water, or these liquid mixture can be used suitably. Examples of the alcohol include lower alcohols having 1 to 4 carbon atoms such as methanol, ethanol, propanol, isopropyl alcohol, and butanol. Preferably it is water or hydrous alcohol. The water-containing alcohol preferably has an alcohol content of 40% by volume or less.

  Moreover, an acidic solution, specifically, an acidic solution adjusted to pH 1 to 4, preferably pH 1 to 3, can also be used as a solvent used for extraction. Such an acidic solution can be prepared by blending an extraction solvent with an inorganic acid such as hydrochloric acid, sulfuric acid, nitric acid or phosphoric acid, or an organic acid such as citric acid, acetic acid, malic acid or lactic acid. The amount of the inorganic acid or organic acid to be blended in the extraction solvent is not particularly limited as long as it has the above pH range, but it is preferably adjusted as appropriate in the range of 0.01 to 10% by weight.

  As the extraction method, a generally used method can be arbitrarily adopted. Although it is not limited, for example, in a plant belonging to the genus Ipomoea belonging to the family Convolvulaceae in a solvent, a part containing the target pigment (as it is or crude powder, shredded product) or a dried product thereof (dried shredded product (powder etc.) And the like), a method of performing extraction while heating and stirring, filtering and obtaining an extract, or a percolation method.

  A suitable extraction method is extraction under acidic conditions. Extraction under such acidic conditions is carried out in plants belonging to the genus Ipomoea belonging to the family Convolvulaceae, containing the target pigment (as it is, crude powder, shredded products) or dried products thereof (dried shredded products (such as powders) (Including the pulverized product) can be carried out by performing the above-described various extraction processes using the acidic extraction solvent described above. Preferably, in a plant belonging to the genus Ipomoea belonging to the family Convolvulaceae in an acidic extraction solvent, a method of extracting the target pigment-containing site (raw or dried product) while chopping, or in a plant belonging to the genus Ipomoea belonging to the family Convolvulaceae And a method of chopping a portion (raw or dried product) containing the target pigment and then immersing it in an acidic extraction solvent. In this case, the extraction treatment can also be performed using an acidic extraction solvent heated to 100 ° C. or lower. More preferably, in a plant belonging to the genus Ipomoea belonging to the family Convolvulaceae, a shredded product of a target pigment-containing site (raw or dried product) is immersed in an acidic extraction solvent having a pH of 1 to 4, and then 100 ° C. This is an extraction method in which heat treatment is performed at the following temperature.

  The obtained extract is subjected to an adsorption treatment as it is or after being concentrated after removing solids by filtration, coprecipitation or centrifugation as required. The adsorption treatment can be carried out according to a conventional method, for example, adsorption treatment with activated carbon, silica gel, porous ceramic or the like; styrene-based duolite S-861 (trademark Duolite, USA, manufactured by Diamond Shamrock, The same shall apply hereinafter), Duolite S-862, Duolite S-863 or Duolite S-866; aromatic Sepa beads SP70 (trademark, manufactured by Mitsubishi Chemical Corporation, the same shall apply hereinafter), Sepa beads SP700, Sepa beads SP825; Diaion HP10 (trademark, manufactured by Mitsubishi Chemical Corporation, the same applies hereinafter), Diaion HP20, Diaion HP21, Diaion HP40, and Diaion HP50; or Amberlite XAD-4 (trademark, manufactured by Organo, the same applies hereinafter), Amberlite XAD-7, Amberlite XAD-2 The synthetic adsorption resin such as 00 adsorption treatment can be given using.

  The adsorption treatment liquid used in the present invention is recovered and obtained by washing a resin carrier, to which a pigment component belonging to the genus Ipomoea belonging to the family Convolvulaceae is attached, adsorbing the pigment component, with an appropriate solvent such as hydrous alcohol, for example. be able to. As a hydrous alcohol, the water which normally contains about 1-20 volume% ethanol can be illustrated suitably.

  The thus obtained adsorption treatment liquid of the plant pigment extract belonging to the genus Ipomoea belonging to the family Convolvulaceae is then subjected to various treatments such as adsorption treatment, ion exchange treatment, acid treatment, extraction treatment or membrane separation treatment. Adsorption treatment, ion exchange treatment, acid treatment or membrane separation treatment is preferred. Examples of the adsorption process include the processes described above.

  The ion exchange treatment is not particularly limited and can be performed according to a conventional method using a conventional ion exchange resin (cation exchange resin or anion exchange resin). Examples of the cation exchange resin include, but are not limited to, Diaion SK1B (trademark, manufactured by Mitsubishi Chemical Corporation, the same shall apply hereinafter), Diaion SK102, Diaion SK116, Diaion PK208, Diaion WK10, Diaion WK20, and the like. Examples of the anion exchange resin include, but are not limited to, Diaion SA10A (trademark, manufactured by Mitsubishi Chemical Corporation, the same shall apply hereinafter), Diaion SA12A, Diaion SA20A, Diaion PA306, Diaion WA10, Diaion WA20, and the like. Is done.

  In addition, the acid treatment referred to in the present invention is an adsorption treatment solution of a plant pigment extract belonging to the genus Ipomoea belonging to the family Convolvulaceae or a treatment solution subjected to the above-described various treatments (adsorption treatment, ion exchange treatment, extraction treatment, membrane separation treatment, etc.). Can be carried out by exposure to acidic conditions of pH 1-4, preferably pH 1-3. Specifically, the acid treatment can be easily carried out by adding and adding an acid to the treatment liquid. Such an acid is not particularly limited as long as it is an acid usually used as a food additive, and can be arbitrarily selected and used. For example, organic acids such as citric acid, acetic acid, malic acid and lactic acid or inorganic acids such as sulfuric acid, hydrochloric acid, phosphoric acid and nitric acid can be exemplified. The acid treatment using an inorganic acid usually used as a food additive is preferable. The temperature conditions for performing the acid treatment are not particularly limited, and can be appropriately selected from the range of 5 to 100 ° C. For example, the range of 20-100 degreeC and 40-100 degreeC can be illustrated. The acid treatment time is not particularly limited, and can be appropriately selected from the range of usually 1 to 300 minutes. In general, a shorter treatment time is sufficient if the acid treatment is performed at a high temperature. For example, in the case of an acid treatment at 40 to 100 ° C., the treatment time can be selected from a range of 5 to 60 minutes. At this time, the treatment liquid is not particularly limited even if it is not stirred.

  In the present invention, the extraction treatment is not particularly limited, but a liquid such as carbon dioxide, ethylene, propane or the like is used as an adsorption treatment solution of a plant pigment extract belonging to the genus Ipomoea belonging to the family Convolvulaceae or the above-mentioned various treatments (adsorption treatment, ion exchange treatment). And a treatment solution that has been subjected to acid treatment or membrane separation treatment) may be brought into contact in a closed system under a temperature and pressure above the critical point.

  Furthermore, the membrane separation treatment in the present invention broadly means a filtration method using a membrane, such as a membrane filter (MF) membrane, an ultrafiltration (UF) membrane, a reverse osmosis membrane (NF), an electrodialysis membrane, and the like. The filtration process using the functional polymer membrane of can be mentioned. In addition, membrane separation treatment includes ultrafiltration and reverse osmosis using these membranes, as well as dialysis using concentration gradients due to ion-selective membranes, and electricity that applies an ion exchange membrane as a diaphragm. Dialysis methods are known. Industrially, a membrane separation method by a reverse osmosis membrane method is preferable. Examples of the membrane material used in the membrane separation method include cellulose, cellulose di-acetate or tri-acetate, polyamide, polysulfone, polystyrene, polyimide, polyacrylonitrile and the like, regardless of whether they are natural, synthetic, or semi-synthetic. be able to.

The membrane separation treatment used in the present invention includes a treatment method in which a polymer compound is separated and removed using a membrane having a fractional molecular weight in the range of, for example, 10 ⁴ to 10 ⁶ , and a fractional molecular weight of about 2,000 to 4, A treatment method for separating and removing low molecular weight compounds using a membrane of about 3,000, preferably about 3,000 is included. Specifically, as the former method, NTU-3150 membrane, NTU-3250 membrane, NTU-3550 membrane, NTU-3800 UF membrane (manufactured by Nitto Denko); Cefilt-UF (manufactured by NGK); AHP-2013 membrane, Examples thereof include ultrafiltration (UF) membrane treatment using AHP-3013 membrane, AHP-1010 membrane (manufactured by Asahi Kasei); and the like. Specific examples of the latter method include NTR-7250 membrane, NTR- 7410 film, NTR-7430 film, NTR-7450 film (manufactured by Nitto Denko); AIP-3013 film, ACP-3013 film, ACP-2013 film, AIP-2013 film, AIO-1010 film (manufactured by Asahi Kasei) And reverse osmosis membrane (fraction molecular weight of about 3,000) treatment using a membrane such as

These various treatments may be performed singly or in any combination of two or more, and the same treatment may be repeated under the same or different conditions.
A preferred treatment method is not particularly limited, but is a method in which an adsorption treatment solution of a plant pigment extract belonging to the genus Ipomoea belonging to the family Convolvulaceae is deproteinized, and then a membrane separation treatment is performed on this treated protein solution.

The deproteinization treatment can be effectively performed by the above-described extraction treatment, ion exchange treatment, membrane separation treatment using an ultrafiltration membrane or the like. In this case, as the membrane separation treatment, a treatment using a membrane having a fractional molecular weight of about 10 ⁴ to 10 ⁶ used for separation and removal of the polymer compound can be suitably employed. However, the deproteinization treatment is not limited to these methods, and can be performed according to a conventional deproteinization treatment such as gel filtration treatment.

  If necessary, an adsorption treatment can be further performed after the deproteinization treatment. As a preferred treatment method, there can be mentioned a method in which a treated dye solution subjected to deproteinization is subjected to an adsorption treatment as necessary, followed by an acid treatment, and a membrane separation treatment is carried out on the treated dye solution thus obtained. . Here, the membrane separation treatment is preferably reverse osmosis membrane treatment or ultrafiltration membrane treatment, and more preferably reverse osmosis membrane treatment. The membrane separation treatment is preferably performed using a membrane having a molecular weight cut-off of 2,000 to 4,000, preferably around 3,000.

  The plant pigment belonging to the genus Convolvulaceae family Ipomoea of the present invention thus obtained is a product obtained by effectively removing the odorous component derived from the plant belonging to the genus Convolvulaceae family Ipomoea, which causes off-flavor or malodor, As a result, it is possible to provide a plant pigment belonging to the genus Ipomoea belonging to the genus Convolvulaceae, which is odorless or has a odor reduced to such an extent that it hardly affects the flavor even when blended with food. Further, the plant pigments belonging to the genus Ipomoea of the family Convolvulaceae of the present invention obtained by the above method are those that do not cause a change over time such as a so-called “odor return phenomenon” even by heating or long-term storage. This is presumably because the precursor of the fragrance component capable of expressing a strange odor or malodor was decomposed or removed by the production method of the present invention.

  The plant pigment belonging to the genus Ipomoea of the family Convolvulaceae of the present invention is a solution state dissolved or dispersed (emulsified) in water, ethanol, alcohol such as propylene glycol, or other solvent, or a dry state (powder, granule, tablet, It can be prepared as a pigment preparation such as a pill form. Preferably, it is in the form of a solution. Therefore, this invention provides the pigment | dye formulation containing the plant pigment which belongs to said Convolvulaceae family Ipomoea genus.

  The pigment preparation may consist of only the plant pigment belonging to the genus Convolvulaceae family Ipomoea of the present invention, and in addition to the plant pigment belonging to the genus Ipomoea family Convolvulaceae, Various additives may be blended. Specific examples of such carriers and additives include, for example, dextrin, lactose, powdered starch syrup, preservatives (sodium acetate, protamine, etc.) commonly used in pigments and pigment preparations, stabilizers (sodium phosphate, sodium metaphosphate, etc.) Or food additives such as antioxidants (rutin, ascorbic acid, etc.).

  When the pigment preparation of the present invention contains various carriers, additives and the like, the blending ratio of the plant pigment belonging to the genus Ipomoea belonging to the Convolvulaceae family contained in the pigment formulation is not particularly limited, but usually 1 to 90% by weight, Preferably 10-60 weight% can be illustrated. The pigment preparation of the present invention is useful as a red or reddish violet colorant for foods, pharmaceuticals, quasi-drugs, cosmetics, and feeds, and particularly as a natural colorant. In addition, coloring in foods and drinks is not only those that are colored by artificially adding pigments to foods and drinks, but also those that are derived from pigments originally contained in food and drink materials such as fruit juice Is widely included.

The present invention includes the following embodiments:
(A). The adsorption treatment solution of the plant pigment extract belonging to the genus Ipomoea belonging to the family Convolvulaceae is to perform at least one treatment selected from the group consisting of adsorption treatment, ion exchange treatment, pH adjustment treatment, extraction treatment and membrane separation treatment. A method for purifying a plant pigment belonging to the genus Ipomoea belonging to the family Convolvulaceae.
(B). A method for purifying a plant pigment belonging to the genus Ipomoea belonging to the Convolvulaceae family, which comprises subjecting the adsorption treatment solution of the plant pigment extract belonging to the genus Ipomoea belonging to the family Convolvulaceae to membrane separation treatment after deproteinization treatment.
(C). The method for purifying plant pigments according to (b), wherein the deproteinization treatment is at least one treatment selected from the group consisting of ion exchange treatment, extraction treatment, membrane separation treatment and gel filtration treatment.
(D). The method for purifying a plant pigment according to (b), wherein a pH adjustment treatment is performed before the membrane separation treatment.
(E). The adsorption treatment solution of the plant pigment extract belonging to the genus Ipomoea belonging to the family Convolvulaceae is to perform at least one treatment selected from the group consisting of adsorption treatment, ion exchange treatment, pH adjustment treatment, extraction treatment and membrane separation treatment. A method for deodorizing plant pigments belonging to the genus Ipomoea belonging to the family Convolvulaceae.
(F). A method for deodorizing a plant pigment belonging to the genus Ipomoea belonging to the Convolvulaceae family, which comprises subjecting the adsorption treatment solution of the plant pigment extract belonging to the genus Ipomoea family of Convolvulaceae to membrane separation after deproteinization treatment.
(G). The method for deodorizing a plant pigment according to (e), wherein the deproteinization treatment is at least one treatment selected from the group consisting of ion exchange treatment, extraction treatment, membrane separation treatment and gel filtration treatment.
(H). The method for deodorizing plant pigments according to (e), wherein a pH adjustment treatment is performed before the membrane separation treatment.
(I). Color value is E ^10% _1cm = 160
In this case, the use of a plant pigment belonging to the genus Ipomoea belonging to the family Convolvulaceae having an aroma component concentration of 150 ppm or less as an edible colorant.
(J). The aroma component is 2-methylbutanol, isoamyl alcohol, tridecane, ethyl lactate, hexanol, trans-linalool oxide, benzyl alcohol, phenethyl alcohol, 5-methylthiopentanenitrile, phenylpropanenitrile, ethyl-2-hydroxy-3-phenyl Propane, dimethyl phthalate, dihydroactinidiolide, 4-vinylphenol, triethyl citrate, dibutyl phthalate, 4-vinyl-2,6-dimethoxyphenol, phenylacetic acid, ethyl vanillate, 4-ethylcatechol, limonene, cis-pinane , Α-terpineol, N-nitrosodibutylamine, guaiacol, 3,7-dimethyloct-1-ene-3,7-diol, 3-hydroxy-α-pyrone, phenol, γ-nonalacto Use of the plant pigment as described in (i), which is at least one selected from the group consisting of N, 4-vinylguaiacol, vanillin, dibutyl phthalate and acetic acid.

  Hereinafter, the content of the present invention will be specifically described with reference to the following examples and comparative examples, but the present invention is not limited thereto.

Comparative Example 1 Extraction of plant pigment belonging to the genus Ipomoea belonging to the family Convolvulaceae 10 kg of Ipomoea Batatas (plant belonging to the genus Ipomoea belonging to the family Convolvulaceae) was poured into 20 L of acidic water adjusted to pH 2 and left overnight at room temperature. The pigment was extracted. The obtained pigment extract was mixed with a filter aid and diatomaceous earth, and suction filtered to obtain about 25 L of a plant pigment extract as the filtrate. This extract was subjected to synthetic adsorption resin Amberlite XAD-7 (resin amount 3 L, SV = 1, manufactured by Organo) to adsorb the dye component, and the resin was thoroughly washed with 10 L of water, and then a 60% ethanol aqueous solution. The eluate was obtained as an adsorption treatment solution of a plant pigment extract belonging to the genus Ipomoea belonging to the family Convolvulaceae (primary purified pigment extract: 10 L). Subsequently, this adsorption treatment liquid was concentrated under reduced pressure to obtain 160 g of a dye liquid having a color value E of ^10% _{1 cm} = 300. 80 g of water and 60 g of ethanol were added to 160 g of this concentrated liquid to prepare 300 g of a plant pigment preparation having a color value E ^10% _{1 cm} = 160. When I smelled this pigment preparation, there was a vegetable smell peculiar to plants belonging to the genus Ipomoea of the family Convolvulaceae.

Example 1 Plant pigment preparation belonging to the genus Ipomoea of the family Convolvulaceae (in solution)
8 L of a primary purified pigment extract (adsorption treatment solution of a plant pigment extract belonging to the genus Ipomoea belonging to the family Convolvulaceae) obtained by the same method as in Comparative Example 1 was applied to an ultrafiltration membrane (AHP-2013 membrane (trademark): manufactured by Asahi Kasei). , Fractional molecular weight 50,000), and treated at 3.5 kg / cm ² and 20 ° C. (membrane separation treatment). Next, the obtained treatment liquid was adjusted to pH 2.0 using sulfuric acid, and stirred for 30 minutes under a temperature condition of 40 to 80 ° C. (acid treatment). Subsequently, 5 L of water was added to the acid treatment solution, and reverse osmosis membrane treatment (NTR-7250 membrane (trademark): manufactured by Nitto Denko, fractional molecular weight of about 3,000) was performed to obtain 1 L of membrane treatment solution. (Membrane separation treatment). At this time, aroma components and contaminants of plants belonging to the genus Ipomoea belonging to the family Convolvulaceae were permeated and removed as filtrate, and the purified and deodorized pigment component was concentrated as a residual solution. Subsequently, this residual liquid was concentrated under reduced pressure to obtain 120 g of a concentrated liquid having a color value E of ^10% _{1 cm} = 300 and significantly deodorized and purified. 60 g of water and 45 g of ethanol were added to 120 g of this concentrated liquid to prepare 225 g of a plant pigment preparation belonging to the genus Ipomoea belonging to the family Convolvulaceae having a color value of E ^10% _{1 cm} = 160. This formulation was completely odorless.

Example 2 Plant pigment preparation belonging to the genus Ipomoea of the family Convolvulaceae (solid form)
Was prepared in the same manner as in Example 1, the dye solution 30g which is significantly deodorized purification of color value ^E _10% 1cm = 300, and dried by spray drying by adding water 60g and dextrin 15 g, color value ^{E 10} 25 g of a plant pigment powder formulation belonging to the genus Ipomoea belonging to the family Convolvulaceae of ^% _{1 cm} = 350 was prepared. This formulation was odorless.

Example 3 GC-MS Measurement The amount of aroma components contained in the plant pigment preparation (comparative product) produced in Comparative Example 1 and the plant pigment formulation of the present invention produced in Example 1 (product of the present invention) was measured by gas chromatography. -Comparison was made using a mass spectrometer (GC-MS). Specifically, 2.5 g of each pigment (color value E ^10% _{1 cm} = 160) is extracted with 200 ml of diethyl ether containing 0.5 ppm of an internal standard substance (IS: 3-heptanol), and then the diethyl ether solution is extracted. After concentration under reduced pressure, the resulting concentrated solution was subjected to a gas chromatography / mass spectrometer (GC-MS) under the following conditions to measure the amount of aroma components.
<GC-MS measurement conditions>
GC: Agilent 6890
MSD: Agilent 5973N
Column: DB-WAX (0.25 mm x 60 m) manufactured by J & W
Temperature conditions: injection port 250 ° C, interface 230 ° C
Column temperature 50 ° C. (2 minutes) −220 ° C., temperature increase 3 ° C./minute split ratio: 70: 1
Ionization voltage: 70 eV

  The results are shown in FIGS. As shown in FIG. 1, according to the total ion chromatogram of the plant pigment preparation of Example 1 (product of the present invention), the components other than the internal standard substance were extremely small amounts (100 ppm or less). On the other hand, as shown in FIG. 2, it was observed that the plant pigment preparation of Comparative Example 1 (comparative product) contained many volatile components (total amount of about 600 ppm). This result indicates that the pigment preparation of Comparative Example 1 had a strong vegetable odor or pickle odor peculiar to plants belonging to the genus Ipomoea belonging to the family Convolvulaceae, whereas the pigment preparation of Example 1 was odorless. It was consistent with the facts.

Example 4 Flavor Evaluation and Storage Test For the plant pigment preparation (comparative product) produced in Comparative Example 1 and the plant pigment formulation (invention product) produced in Example 1, the flavor immediately after production and 5 ° C and 25 ° C, respectively. Alternatively, the flavor after storage for 15 to 30 days at 38 ° C. was evaluated by 10 panelists who were well trained in the flavor list. Also, a beverage type solution (color value E ^10% _{1 cm} = 0.04, Brix. ¹⁰ °, 0.2% citric acid aqueous solution, no flavor added) is prepared using each pigment preparation, In the same manner as described above, the flavor immediately after preparation and after storage was comparatively evaluated. The results are shown in Table 1.

<Evaluation criteria>
A: No odor at all B: Slight odor C: Odor odor D: Strong odor E: Very strong odor

  As can be seen from the results immediately after production shown in Table 1, the product of the present invention has a significantly reduced odor compared to the comparative product, and was judged to be a substantially odorless pigment. In addition, the comparative product became stronger as the storage time increased from 15 to 30 days, whereas the product of the present invention maintained an odorless state immediately after preparation without causing a change with time. This is because the plant pigments belonging to the genus Ipomoea belonging to the family Convolvulaceae of the present invention produced by the method of Example 1 contain not or almost no fragrance component exhibiting odor per se, but also the fragrance component. This suggests that impurities that are precursors of the above are also not included.

  The plant pigment belonging to the genus Ipomoea belonging to the family Convolvulaceae of the present invention is highly purified, so that there is no malodor or off-flavor derived from aroma components contained in the plant belonging to the genus Convolvulaceae family Ipomoea used as a raw material, or the odor An odorless or slightly odorous pigment that is significantly reduced. Furthermore, the plant pigments belonging to the genus Ipomoea belonging to the family Convolvulaceae of the present invention are those in which changes over time such as an odor return phenomenon are significantly suppressed even by heating or long-term storage. Therefore, the pigment of the present invention or a pigment preparation containing the pigment is a plant-specific aroma component belonging to the genus Ipomoea belonging to the family Convolvulaceae, even when used for coloring beverages, other foods, pharmaceuticals, quasi drugs, cosmetics, etc. A product with a good flavor can be produced without being affected by the smell of

It is a figure which shows the result of having measured the amount of aroma components contained in the plant pigment preparation which belongs to the Convolvulaceae family Ipomoea genus prepared in Example 1 with the gas chromatography and mass spectrometer (GC-MS). The IS peak indicates 3-heptanol which is an internal standard substance, and the BHT peak indicates 2,6-di-t-butyl-4-methylphenol contained as a stabilizer for diethyl ether. In the figure, the vertical axis represents strength (Abundance), and the horizontal axis represents retention time. It is a figure which shows the result of having measured the aromatic component amount contained in the plant pigment preparation which belongs to the Convolvulaceae family Ipomoea genus prepared in the comparative example 1 with the gas chromatography and mass spectrometer (GC-MS).

Claims (3)

A method for producing an anthocyanin pigment derived from Ipomoea Batatas having an aromatic component concentration of 150 ppm or less when the color value is ^E10% _{1 cm} = 160 ,
The aromatic component is 2-methylbutanol, isoamyl alcohol, tridecane, ethyl lactate, hexanol, trans-linalool oxide, benzyl alcohol, phenethyl alcohol, 5-methylthiopentanenitrile, phenylpropanenitrile, ethyl-2-hydroxy-3-phenyl Propane, dimethyl phthalate, dihydroactinidiolide, 4-vinylphenol, triethyl citrate, dibutyl phthalate, 4-vinyl-2,6-dimethoxyphenol, phenylacetic acid, ethyl vanillate, 4-ethylcatechol, limonene, cis-pinane , Α-terpineol, N-nitrosodibutylamine, guaiacol, 3,7-dimethyloct-1-ene-3,7-diol, 3-hydroxy-α-pyrone, phenol, γ-nonalactone, 4-vinyl guaiacol, Phosphorus, at least one selected from the group consisting of dibutyl phthalate and acetic acid,
Performing an ultrafiltration membrane treatment on the adsorption treatment solution of the Ipomoea Batatas dye extract;
Acid-treating the ultrafiltration membrane treatment solution; and
A method for producing an anthocyanin dye, comprising a step of subjecting the acid treatment liquid to a membrane separation treatment. The method for producing an anthocyanin dye according to claim 1, wherein the ultrafiltration membrane treatment is a treatment using a membrane having a fractional molecular weight of 10 ⁴ to 10 ⁶ . The method for producing an anthocyanin dye according to claim 1 or 2, wherein the membrane separation treatment is a treatment using a membrane having a fractional molecular weight of 2000 to 4000.

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