WO2013031022A1 - Shellac, taste-improving agent, food, drink and coating composition - Google Patents

Shellac, taste-improving agent, food, drink and coating composition Download PDF

Info

Publication number
WO2013031022A1
WO2013031022A1 PCT/JP2011/070063 JP2011070063W WO2013031022A1 WO 2013031022 A1 WO2013031022 A1 WO 2013031022A1 JP 2011070063 W JP2011070063 W JP 2011070063W WO 2013031022 A1 WO2013031022 A1 WO 2013031022A1
Authority
WO
WIPO (PCT)
Prior art keywords
shellac
coated
food
solution
acid
Prior art date
Application number
PCT/JP2011/070063
Other languages
French (fr)
Japanese (ja)
Inventor
森　大輔
温 鹿島
Original Assignee
株式会社岐阜セラツク製造所
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 株式会社岐阜セラツク製造所 filed Critical 株式会社岐阜セラツク製造所
Priority to JP2013530990A priority Critical patent/JP5665998B2/en
Priority to PCT/JP2011/070063 priority patent/WO2013031022A1/en
Publication of WO2013031022A1 publication Critical patent/WO2013031022A1/en

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D193/00—Coating compositions based on natural resins; Coating compositions based on derivatives thereof
    • C09D193/02—Shellac
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23C—DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING THEREOF
    • A23C19/00—Cheese; Cheese preparations; Making thereof
    • A23C19/14—Treating cheese after having reached its definite form, e.g. ripening, smoking
    • A23C19/16—Covering the cheese surface, e.g. with paraffin wax
    • 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
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/52—Adding ingredients
    • A23L2/56—Flavouring or bittering agents
    • 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
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/88—Taste or flavour enhancing agents
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L93/00—Compositions of natural resins; Compositions of derivatives thereof
    • C08L93/02—Shellac
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09F—NATURAL RESINS; FRENCH POLISH; DRYING-OILS; OIL DRYING AGENTS, i.e. SICCATIVES; TURPENTINE
    • C09F1/00—Obtaining purification, or chemical modification of natural resins, e.g. oleo-resins
    • C09F1/02—Purification
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12G—WINE; PREPARATION THEREOF; ALCOHOLIC BEVERAGES; PREPARATION OF ALCOHOLIC BEVERAGES NOT PROVIDED FOR IN SUBCLASSES C12C OR C12H
    • C12G3/00—Preparation of other alcoholic beverages
    • C12G3/04—Preparation of other alcoholic beverages by mixing, e.g. for preparation of liqueurs
    • C12G3/06—Preparation of other alcoholic beverages by mixing, e.g. for preparation of liqueurs with flavouring ingredients

Definitions

  • the present invention relates to shellac that is added to foods and drinks and pharmaceuticals or used as a coating agent.
  • Shellac (shellac) is a refined resinous substance secreted by the scale insect. Since shellac is harmless to the human body and has moisture resistance and good glossiness, it is used for foods such as chocolate and gum, and surface coatings for health foods and pharmaceutical tablets.
  • shellac When coating shellac on food or the like, a process is performed in which shellac is dissolved in an alcohol solvent and applied to the entire surface of the object to be coated, and then the solvent component is removed by drying (see, for example, Patent Document 1). Moreover, it can also be water-solubilized with an alkali and coated.
  • Shellac has a peculiar bitter taste, and the coating of shellac may impair the flavor of foods and the like.
  • One object of the present invention is to provide shellac with reduced bitterness, a taste improver containing the shellac, a food and drink, and a coating composition.
  • Another object of the present invention is to provide a taste improver and a food or drink containing a bitter component of shellac.
  • the shellac according to the first aspect of the present invention which has been made to solve the above-mentioned problems, is a shellac characterized in that the content of the ester compound of jaralic acid and alleuritic acid is 4.0% by weight or less.
  • the above-mentioned jarral acid also includes epi-jararic acid, which is a stereoisomer of jaralic acid.
  • the inventors of the present invention have discovered that among resin acids constituting shellac, an ester compound of gallaric acid (epi-jararic acid) and alleuritic acid is a bitter component, and the content of the ester compound It has been found that the bitter taste of shellac is greatly reduced when the content is 4.0% by weight or less.
  • the shellac having the above-described configuration can reduce bitterness when the shellac is added or when a food or drink coated with the shellac is taken or when a medicine coated with the shellac is orally administered.
  • the bitterness reduction can be implement
  • the taste improver of the third aspect of the present invention is a taste improver containing as an active ingredient any shellac of the first aspect and the second aspect of the present invention. Since the bitterness of the shellac of any of the first and second aspects of the present invention is reduced, it is difficult to increase the unpleasant bitterness even when added to food and drink. Furthermore, the taste improvement effect which shellac has can be provided to food-drinks. Although the taste improvement effect of shellac varies depending on the food or drink added, mellowness, sweetness, and the like can be increased as an example.
  • the food / beverage product of the 4th aspect of this invention is a food / beverage product to which the shellac in any one of the 1st aspect and 2nd aspect of this invention is added.
  • Such foods and drinks can exhibit a taste improving effect by shellac.
  • the alcoholic beverage like the 5th aspect of this invention can be considered as an example of food / beverage products.
  • mellowness and sweetness can be added to the alcoholic beverage.
  • the coating composition according to the sixth aspect of the present invention is a coating composition used for at least one of foods and pharmaceuticals containing shellac according to any of the first and second aspects of the present invention. Since the bitterness of the shellac of the first and second aspects of the present invention is reduced, it is advantageous that the bitterness is hardly given to foods and pharmaceuticals even when used as a coating agent for foods and pharmaceuticals.
  • the taste improver according to the seventh aspect of the present invention is a taste improver comprising an ester compound of jaralic acid and alleuritic acid as an active ingredient.
  • the above-mentioned jarral acid may be epi-jararic acid which is a stereoisomer of jaralic acid.
  • ester compounds have a bitter taste and bring various taste-improving effects to foods and drinks when taken at the same time as foods and drinks. Therefore, if it is such a taste improving agent, the taste of food-drinks can be improved.
  • the food / beverage product of the eighth aspect of the present invention is a food / beverage product to which an ester compound of gallaric acid and aleuric acid is added.
  • the above-mentioned jarral acid may be epi-jararic acid which is a stereoisomer of jaralic acid.
  • Such food and drink can exhibit the taste improving effect of the ester compound.
  • an alcoholic beverage can be considered like the food and drink of the ninth aspect of the present invention.
  • FIG. 13 shows a 13C-NMR spectrum of Compound 1.
  • Shellac is a natural resin and consists of a mixture of a number of resin acids and their ester compounds, waxes and pigments.
  • main ester compounds include esters of cedrene compounds and fatty acids.
  • An example of a cedrene compound considered to be contained in shellac is shown in FIG.
  • Examples of oxycarboxylic acids as fatty acids are shown in FIGS. 2A-2C.
  • FIG. 3 shows the structural formula of the ester compound of gallaric acid and alleuritic acid among the above-mentioned cedrene compounds and oxycarboxylic acids.
  • the ester compound shown in FIG. 3 is one of the substances constituting shellac.
  • the bitterness of each fraction taken 5 mL was evaluated.
  • a portion of each fraction was concentrated under reduced pressure, vacuum dried to remove methanol, dissolved in ethanol, and adjusted with distilled water so that the final ethanol concentration was 5 vol% and the shellac concentration was 1 mg / mL.
  • the bitterness was evaluated by sensory evaluation. Evaluators (examiners) were six women in their twenties. The test solution 0.1 mL described above was dropped on the evaluator's tongue, and it was determined that there was a bitter taste if the number of persons judged to feel bitter was 4 or more.
  • Fr. 2 was fractionated using the above-described LH-20 column ( ⁇ 2.2 ⁇ 45 cm) in the same manner as in the above treatment 2, and the bitterness was evaluated. The fractions that felt bitter were combined and concentrated. .5 mg fraction (Fr.3) was obtained.
  • Shellac A prepared in Example 1 was dissolved in ethanol to prepare a 100 mg / mL solution. This solution is referred to as Solution B for convenience.
  • the content (content ratio) of Compound 1 in shellac A was measured using LC / MS-MS, it was found to be 1.74% by weight.
  • Solution C 99% 4vol% ethanol was added to the above solution B (1mL) to prepare a 5vol% ethanol solution with shellac A concentration of 1mg / mL.
  • This solution is referred to as Solution C for convenience.
  • the isolated compound 1 is added to the solution C, and the content of the compound 1 becomes 3.25% by weight (Test Example 1), the solution becomes 3.50% by weight (Test Example 2), 3.75% by weight % Solution (Test Example 3), 4.00% by weight solution (Test Example 4), 4.25% by weight solution (Test Example 5), 4.50% by weight solution (Test Example 6) )created.
  • the content rate of the compound 1 said here is not the content rate in a solution but the content rate of the compound 1 at the time of converting into shellac single-piece
  • a taste improver containing the above shellac as an active ingredient can be added to a general food or drink to improve the taste.
  • foods and pharmaceuticals can be coated with the coating composition containing the shellac.
  • Conventionally, foods and the like are coated with a composition containing shellac, but bitterness can be reduced by using the shellac of the present invention.
  • Shellac A prepared in Example 1 was dissolved in 99 vol% ethanol to produce a 100 mg / mL taste improver ( ⁇ solution). This ⁇ liquid was added to whiskey to produce whiskey with improved taste.
  • Example 1 Shellac A with reduced bitterness components prepared in Example 1 was dissolved in ethanol, coated with ball-shaped chocolate, and then dried to produce chocolate coated with shellac with reduced bitterness components.
  • purified shellac GSN was dissolved in ethanol, coated with ball-shaped chocolate, and then dried to produce chocolate coated with purified shellac GSN.
  • the shellac A prepared in Example 1 was dissolved in ethanol, and the sugar-coated chocolate was coated with the solution and then dried to produce sugar-coated chocolate coated with shellac.
  • Example 1 Shellac A prepared in Example 1 was dissolved in ethanol, a plate-shaped chocolate was coated with the solution, and then dried to produce chocolate coated with shellac.
  • the shellac A prepared in Example 1 was dissolved in ethanol, and the chocolate-coated biscuits were coated with the solution and then dried to produce chocolate-coated biscuits coated with shellac.
  • the shellac A prepared in Example 1 was dissolved in ethanol, and the chocolate-coated corn flakes were coated with the solution and dried to produce chocolate corn flakes coated with shellac.
  • the shellac A prepared in Example 1 was dissolved in ethanol, and the chocolate-coated dry strawberry was coated with the solution and dried to produce a chocolate-coated dry strawberry coated with shellac.
  • the shellac A prepared in Example 1 was dissolved in ethanol, and the sugar-coating gum was coated with the solution and then dried to produce sugar-coating gum coated with shellac.
  • the shellac A prepared in Example 1 was dissolved in ethanol, the gummi was coated with the solution, and then dried to produce a gummi coated with shellac.
  • Shellac A prepared in Example 1 was dissolved in ethanol, baked laver was coated with the solution, and dried to produce baked laver coated with shellac.
  • Example 1 Shellac A prepared in Example 1 was dissolved in ethanol, cheese was coated with the solution, and then dried to produce cheese coated with shellac.
  • Shellac A prepared in Example 1 was dissolved in ethanol, peeled chestnut was coated with the solution, and dried to produce peeled chestnut coated with shellac.
  • the shellac A prepared in Example 1 was dissolved in ethanol, and a soft hanging jelly was coated with the solution and dried to produce a soft hanging jelly coated with shellac.
  • Example 1 Shellac A prepared in Example 1 was dissolved in ethanol, and a soft hanging candy was coated with the solution and dried to produce a soft hanging candy coated with shellac.
  • the shellac A prepared in Example 1 was dissolved in ethanol, and the solution was coated with chocolate raisins and dried to produce a chocolate raisins coated with shellac.
  • the shellac A prepared in Example 1 was dissolved in ethanol, and the chocolate-coated cookie was coated with the solution and then dried to produce a chocolate-coated cookie coated with shellac.
  • the shellac A prepared in Example 1 was dissolved in ethanol, and a solid preparation for oral administration was coated with the solution and then dried to produce a solid preparation coated with shellac.
  • Example 7 Verification of the effect of improving flavor in alcoholic beverages of shellac with reduced bitterness components
  • the flavor of the whiskey produced in Example 2 was evaluated.
  • 0.1 mL of the shellac solution ( ⁇ solution) produced in Example 2 was added to 10 mL of whiskey, and 0.1 mL of this whiskey was dropped on the tongue to evaluate the flavor.
  • decolorized shellac PEARL-N5 (trade name, manufactured by Gifu Serask Manufacturing Co., Ltd.) in 99 vol% ethanol, 100 mg / mL shellac solution ( ⁇ solution), and 99 vol% ethanol (blank solution) ) And prepared.
  • the ⁇ solution and 0.1 mL of the blank solution were added to 10 mL of whiskey, and 0.1 mL of this whiskey was dropped on the tongue to evaluate the flavor.
  • the results are shown in Table 4.
  • whiskey to which the ⁇ solution was added increased in mellowness and sweetness, whereas the whiskey to which the ⁇ solution was added had increased bitterness.
  • the taste of whiskey did not change in the blank solution, and it had a bitter taste stronger than the whiskey to which the ⁇ solution was added and weaker than the whiskey to which the ⁇ solution was added.
  • a taste improver containing the compound 1 as an active ingredient can be added to a general food or drink to improve the taste.
  • a taste improver containing the compound 1 as an active ingredient can be added to a general food or drink to improve the taste.
  • Compound 1 was dissolved in 99 vol% ethanol to prepare a 100 mg / mL solution ( ⁇ solution). This ⁇ liquid was added to whiskey to produce whiskey with improved taste. 9. Verification of Alcohol Stimulation Reduction Effect of Bitter Taste The flavor of the whiskey produced in Example 18 was evaluated. 0.1 mL of the solution ( ⁇ liquid) produced in Example 18 was added to 10 mL of whiskey, and 0.1 mL of this whiskey was dropped on the tongue, and the alcohol stimulation felt was evaluated.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Food Science & Technology (AREA)
  • Wood Science & Technology (AREA)
  • Nutrition Science (AREA)
  • Genetics & Genomics (AREA)
  • Biochemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Zoology (AREA)
  • Materials Engineering (AREA)
  • General Preparation And Processing Of Foods (AREA)
  • Medicinal Preparation (AREA)
  • Seasonings (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)

Abstract

A shellac characterized by containing an ester compound of jalaric acid and aleuritic acid in an amount of 4.0 wt% or less.

Description

セラック、呈味改善剤、飲食品、およびコーティング用組成物Shellac, taste improver, food and drink, and coating composition
　本発明は、飲食品や医薬品に添加され、あるいはコーティング剤として用いられるセラックに関する。 The present invention relates to shellac that is added to foods and drinks and pharmaceuticals or used as a coating agent.
　セラック（シェラック、ｓｈｅｌｌａｃ）は、ラックカイガラムシが分泌する樹脂状物質を精製したものである。セラックは人体に無害であり、また防湿性や良好な光沢性を有するため、チョコレートやガムを始めとした食品や、健康食品や医薬品のタブレットなどの表面コーティングなどに用いられている。 Shellac (shellac) is a refined resinous substance secreted by the scale insect. Since shellac is harmless to the human body and has moisture resistance and good glossiness, it is used for foods such as chocolate and gum, and surface coatings for health foods and pharmaceutical tablets.
　セラックを食品等にコーティングする際には、セラックをアルコール溶媒に溶解させて被コーティング物の表面全体に塗布した後、溶媒成分を乾燥除去する工程が行われる（例えば特許文献１参照）。また、アルカリによって水溶化し、コーティングすることもできる。 When coating shellac on food or the like, a process is performed in which shellac is dissolved in an alcohol solvent and applied to the entire surface of the object to be coated, and then the solvent component is removed by drying (see, for example, Patent Document 1). Moreover, it can also be water-solubilized with an alkali and coated.
特開平８－３１１４０５号公報JP-A-8-311405
　セラックには特有の苦味があり、セラックをコーティングすることによって食品等の風味を損なってしまう場合があった。
　本発明の１つの目的は、苦味を低減したセラック、当該セラックを含有する呈味改善剤，飲食品，およびコーティング用組成物を提供することである。本発明の他の目的は、セラックの苦味成分を含有する呈味改善剤および飲食品を提供することである。 Shellac has a peculiar bitter taste, and the coating of shellac may impair the flavor of foods and the like.
One object of the present invention is to provide shellac with reduced bitterness, a taste improver containing the shellac, a food and drink, and a coating composition. Another object of the present invention is to provide a taste improver and a food or drink containing a bitter component of shellac.
　上述した問題を解決するためになされた本発明の第１局面のセラックは、ジャラール酸とアレウリチン酸とのエステル化合物の含有率が４．０重量％以下であることを特徴とするセラックである。なお、上記ジャラール酸には、ジャラール酸の立体異性体であるｅｐｉ－ジャラール酸も含まれる。 The shellac according to the first aspect of the present invention, which has been made to solve the above-mentioned problems, is a shellac characterized in that the content of the ester compound of jaralic acid and alleuritic acid is 4.0% by weight or less. Note that the above-mentioned jarral acid also includes epi-jararic acid, which is a stereoisomer of jaralic acid.
　本発明の発明者らは、セラックを構成する樹脂酸のうち、ジャラール酸（ｅｐｉ－ジャラール酸）とアレウリチン酸とのエステル化合物が苦味成分であることを発見し、さらに、そのエステル化合物の含有率が４．０重量％以下である場合に、セラックの苦味が非常に低減されることを見出した。 The inventors of the present invention have discovered that among resin acids constituting shellac, an ester compound of gallaric acid (epi-jararic acid) and alleuritic acid is a bitter component, and the content of the ester compound It has been found that the bitter taste of shellac is greatly reduced when the content is 4.0% by weight or less.
　従って、上記構成のセラックであれば、当該セラックが添加され、あるいはコーティングされた飲食物を口にするとき、または当該セラックがコーティングされた医薬品を経口投与するときの苦味を低減することができる。 Therefore, the shellac having the above-described configuration can reduce bitterness when the shellac is added or when a food or drink coated with the shellac is taken or when a medicine coated with the shellac is orally administered.
　なお、本発明の第２局面のセラックのように、エステル化合物の含有率を３．５重量％以下とすることで、さらに顕著に苦味の低減を実現できる。
　本発明の第３局面の呈味改善剤は、本発明の第１局面および第２局面のいずれかのセラックを有効成分とする呈味改善剤である。本発明の第１局面および第２局面のいずれかのセラックは苦味が低減されているので飲食品に添加しても不快な苦味を増加させにくい。さらに、セラックが有する呈味改善効果を飲食品に付与することができる。セラックの呈味改善効果は添加される飲食品によって異なるが、一例としてまろやかさ、甘さなどを増加させることができる。 In addition, like the shellac of the 2nd aspect of this invention, the bitterness reduction can be implement | achieved more notably by making content rate of an ester compound into 3.5 weight% or less.
The taste improver of the third aspect of the present invention is a taste improver containing as an active ingredient any shellac of the first aspect and the second aspect of the present invention. Since the bitterness of the shellac of any of the first and second aspects of the present invention is reduced, it is difficult to increase the unpleasant bitterness even when added to food and drink. Furthermore, the taste improvement effect which shellac has can be provided to food-drinks. Although the taste improvement effect of shellac varies depending on the food or drink added, mellowness, sweetness, and the like can be increased as an example.
　本発明の第４局面の飲食品は、本発明の第１局面および第２局面のいずれかのセラックが添加されてなる飲食品である。このような飲食品は、セラックによる呈味改善効果を奏することができる。なお、飲食品の一例として、本発明の第５局面のようなアルコール飲料が考えられる。アルコール飲料にセラックを添加すると、アルコール飲料にまろやかさ、甘さなどを加えることができる。 The food / beverage product of the 4th aspect of this invention is a food / beverage product to which the shellac in any one of the 1st aspect and 2nd aspect of this invention is added. Such foods and drinks can exhibit a taste improving effect by shellac. In addition, the alcoholic beverage like the 5th aspect of this invention can be considered as an example of food / beverage products. When shellac is added to an alcoholic beverage, mellowness and sweetness can be added to the alcoholic beverage.
　本発明の第６局面のコーティング用組成物は、本発明の第１局面および第２局面のいずれかのセラックを含有する食品および医薬品の少なくともいずれか一方に用いるコーティング用組成物である。本発明の第１局面および第２局面のセラックは苦味が低減されているので食品や医薬品のコーティング剤として使用しても食品や医薬品に苦味を与えにくく都合がよい。 The coating composition according to the sixth aspect of the present invention is a coating composition used for at least one of foods and pharmaceuticals containing shellac according to any of the first and second aspects of the present invention. Since the bitterness of the shellac of the first and second aspects of the present invention is reduced, it is advantageous that the bitterness is hardly given to foods and pharmaceuticals even when used as a coating agent for foods and pharmaceuticals.
　本発明の第７局面の呈味改善剤は、ジャラール酸とアレウリチン酸とのエステル化合物を有効成分とした呈味改善剤である。なお、上記ジャラール酸は、ジャラール酸の立体異性体であるｅｐｉ－ジャラール酸であってもよい。 The taste improver according to the seventh aspect of the present invention is a taste improver comprising an ester compound of jaralic acid and alleuritic acid as an active ingredient. In addition, the above-mentioned jarral acid may be epi-jararic acid which is a stereoisomer of jaralic acid.
　上記エステル化合物は、苦味を有するとともに、飲食品と同時に摂取すると飲食品にさまざまな呈味の改善効果をもたらす。よってこのような呈味改善剤であれば、飲食品の呈味を改善することができる。 The above ester compounds have a bitter taste and bring various taste-improving effects to foods and drinks when taken at the same time as foods and drinks. Therefore, if it is such a taste improving agent, the taste of food-drinks can be improved.
　本発明の第８局面の飲食品は、ジャラール酸とアレウリチン酸とのエステル化合物が添加されてなる飲食品である。なお、上記ジャラール酸は、ジャラール酸の立体異性体であるｅｐｉ－ジャラール酸であってもよい。このような飲食品は、上記エステル化合物の呈味改善効果を奏することができる。なお、飲食品の一例として、本発明の第９局面の飲食品のようにアルコール飲料が考えられる。アルコール飲料に上記エステル化合物を添加すると、アルコール飲料におけるアルコールの刺激を低減することができる。 The food / beverage product of the eighth aspect of the present invention is a food / beverage product to which an ester compound of gallaric acid and aleuric acid is added. In addition, the above-mentioned jarral acid may be epi-jararic acid which is a stereoisomer of jaralic acid. Such food and drink can exhibit the taste improving effect of the ester compound. In addition, as an example of the food and drink, an alcoholic beverage can be considered like the food and drink of the ninth aspect of the present invention. When the ester compound is added to an alcoholic beverage, alcohol stimulation in the alcoholic beverage can be reduced.
セラックを構成するセドレン化合物の一例を示す図The figure which shows an example of the cedrene compound which comprises shellac セラックを構成するオキシカルボン酸の一例を示す図The figure which shows an example of the oxycarboxylic acid which comprises shellac ジャラール酸とアレウリチン酸とのエステル化合物の構造式を示す図Diagram showing the structural formula of ester compound of jaralic acid and aleuric acid 化合物１の１Ｈ－ＮＭＲスペクトルを示す図1 shows a 1H-NMR spectrum of Compound 1. 化合物１の１３Ｃ－ＮＭＲスペクトルを示す図FIG. 13 shows a 13C-NMR spectrum of Compound 1. 化合物１のLC／MS－MS測定による濃度とピーク面積における検量線Calibration curve for concentration and peak area of Compound 1 by LC / MS-MS measurement
　以下に本発明の実施形態を説明する。
　セラックは天然樹脂であり、多数の樹脂酸およびそのエステル化合物、ワックス、色素の混合物からなる。主要なエステル化合物としてはセドレン化合物と脂肪酸とのエステルが挙げられる。セラックに含まれると考えられるセドレン化合物の一例を図１に示す。また、脂肪酸としてオキシカルボン酸の一例を図２Ａ－２Ｃに示す。また、上述したセドレン化合物とオキシカルボン酸のうち、ジャラール酸とアレウリチン酸とのエステル化合物の構造式を図３に示す。図３に示すエステル化合物はセラックを構成する物質の中の１つである。 Embodiments of the present invention will be described below.
Shellac is a natural resin and consists of a mixture of a number of resin acids and their ester compounds, waxes and pigments. Examples of main ester compounds include esters of cedrene compounds and fatty acids. An example of a cedrene compound considered to be contained in shellac is shown in FIG. Examples of oxycarboxylic acids as fatty acids are shown in FIGS. 2A-2C. FIG. 3 shows the structural formula of the ester compound of gallaric acid and alleuritic acid among the above-mentioned cedrene compounds and oxycarboxylic acids. The ester compound shown in FIG. 3 is one of the substances constituting shellac.
　１．苦味成分の単離
　セラックに含まれる苦味成分を単離する方法について説明する。
　（処理１）　精製セラックＧＳＮ（商品名、株式会社岐阜セラツク製造所製）３０ｇに酢酸エチル３００ｍＬを加え、還流下で３０分間撹拌した後室温まで冷却した。１時間静置した後、上清をデカンテーションにて除いた。残った沈殿に、再び酢酸エチル３００ｍＬを加え、還流下で３０分間撹拌した。室温まで冷却した後１時間静置し、上清をデカンテーションにて除いた。得られた上清を合わせ濃縮し、１１．７ｇの画分（Ｆｒ．１）を得た。 1. Isolation of bitter component A method for isolating a bitter component contained in shellac will be described.
(Treatment 1) Ethyl acetate 300 mL was added to 30 g of purified shellac GSN (trade name, manufactured by Gifu Seratech Manufacturing Co., Ltd.), stirred under reflux for 30 minutes, and then cooled to room temperature. After standing for 1 hour, the supernatant was removed by decantation. To the remaining precipitate, 300 mL of ethyl acetate was added again and stirred for 30 minutes under reflux. After cooling to room temperature, the mixture was allowed to stand for 1 hour, and the supernatant was removed by decantation. The obtained supernatants were combined and concentrated to obtain 11.7 g of a fraction (Fr. 1).
　（処理２）　上記Ｆｒ．１の１２０ｍｇを少量のメタノールに溶解し、メタノールにてコンディショニングしたセファデックスＬＨ－２０（商品名、ＧＥヘルスケア・ジャパン株式会社製）を充填したカラム（φ２．２×４５ｃｍ）に通液した。通液後のＬＨ－２０カラムはメタノールにて溶出を行い、５ｍＬずつ分取した。 (Process 2) Fr. 120 mg of No. 1 was dissolved in a small amount of methanol, and passed through a column (φ2.2 × 45 cm) packed with Sephadex LH-20 (trade name, manufactured by GE Healthcare Japan, Inc.) conditioned with methanol. After passing, the LH-20 column was eluted with methanol, and 5 mL was collected.
　ここで、５ｍＬずつ分取した各画分の苦味評価を行った。各画分の一部について、減圧濃縮、真空乾燥しメタノールを除去した後に、エタノールに溶解し、最終エタノール濃度が５ｖｏｌ％、セラック濃度が１ｍｇ／ｍＬとなるように蒸留水にて調整した試験溶液を作製した。苦味の評価は官能評価により行った。評価者（試験官）は２０代の女性６名とした。上述した試験溶液０．１ｍＬを評価者の舌の上に垂らし、苦味を感じると判断した人数が４名以上であれば、苦味があると判定した。 Here, the bitterness of each fraction taken 5 mL was evaluated. A portion of each fraction was concentrated under reduced pressure, vacuum dried to remove methanol, dissolved in ethanol, and adjusted with distilled water so that the final ethanol concentration was 5 vol% and the shellac concentration was 1 mg / mL. Was made. The bitterness was evaluated by sensory evaluation. Evaluators (examiners) were six women in their twenties. The test solution 0.1 mL described above was dropped on the evaluator's tongue, and it was determined that there was a bitter taste if the number of persons judged to feel bitter was 4 or more.
　そして、苦味があると判定された画分を合わせ濃縮し、９４．６ｍｇの画分（Ｆｒ．２）得た。
　（処理３）　上記Ｆｒ．２を、上述したＬＨ－２０カラム（φ２．２×４５ｃｍ）を用いて、上記処理２と同様の方法で分画するとともに苦味の評価を行い、苦味を感じた画分を合わせ濃縮し、３８．５ｍｇの画分（Ｆｒ．３）得た。 The fractions determined to have bitterness were combined and concentrated to obtain 94.6 mg of fraction (Fr.2).
(Process 3) Fr. 2 was fractionated using the above-described LH-20 column (φ2.2 × 45 cm) in the same manner as in the above treatment 2, and the bitterness was evaluated. The fractions that felt bitter were combined and concentrated. .5 mg fraction (Fr.3) was obtained.
　（処理４）　上記Ｆｒ．３をシリカゲルカラムクロマトグラフィー（和光純薬工業株式会社製ワコーゲルＣ－２００　φ２．２×２０ｃｍ）にて精製した。メタノール：ジクロロメタン＝１：９の溶媒、メタノール：ジクロロメタン＝１：４の溶媒、メタノール、にて順次溶出し、メタノール：ジクロロメタン＝１：４にて溶出した画分を濃縮し、１２．０ｍｇの画分（Ｆｒ．４）を得た。 (Process 4) Fr. 3 was purified by silica gel column chromatography (Wako Gel C-200, φ2.2 × 20 cm, manufactured by Wako Pure Chemical Industries, Ltd.). Methanol: dichloromethane = 1: 9, methanol: dichloromethane = 1: 4 solvent, and methanol were eluted in this order, and the fraction eluted with methanol: dichloromethane = 1: 4 was concentrated to obtain a 12.0 mg fraction. Minute (Fr.4) was obtained.
　（処理５）　Ｆｒ．４をリサイクルＨＰＬＣにて精製し、苦味成分である化合物を３ｍｇ得た。以下の記載において、この苦味成分である化合物を化合物１と称する。リサイクルＨＰＬＣの装置および測定条件を以下に示す。
カラム：野村化学株式会社製Ｄｅｖｅｌｏｓｉｌ ＯＤＳ－１０／２０（φ２０×２５０ｍｍ）
溶媒：８０ｖｏｌ％メタノール
検出波長：２２０ｎｍ
カラムオーブン温度：３０℃
流速：８ｍＬ／ｍｉｎ
　２．単離した苦味成分の苦味の評価
　上記（１．苦味成分の単離）にて得られた化合物１を０．０１５、０．０３１、０．０６３、０．１２５、０．２５０、０．５００ｍｇ／ｍＬの濃度となるように５ｖｏｌ％エタノールにて溶解した試験溶液を作製した。 (Process 5) Fr. 4 was purified by recycle HPLC to obtain 3 mg of a compound which is a bitter component. In the following description, this bitter component is referred to as Compound 1. The apparatus and measurement conditions of recycle HPLC are shown below.
Column: Develosil ODS-10 / 20 (φ20 × 250 mm) manufactured by Nomura Chemical Co., Ltd.
Solvent: 80 vol% methanol Detection wavelength: 220 nm
Column oven temperature: 30 ° C
Flow rate: 8mL / min
2. Evaluation of bitterness of isolated bitterness component 0.015, 0.031, 0.063, 0.125, 0.250, 0.500 mg of compound 1 obtained in the above (1. Isolation of bitterness component) A test solution dissolved in 5 vol% ethanol was prepared so as to have a concentration of / mL.
　上述した試験溶液０．１ｍＬを評価者の舌の上に垂らし、苦味を感じる限界濃度を調べた。評価者（試験官）は２０代の女性６名とした。
　評価の結果、化合物１については女性６名とも０．０１５～０．０６３ｍｇ／ｍＬのいずれかで苦味を感じた。一方、精製セラックＧＳＮにおける苦味を感じる最低濃度は０．２５０～０．５００ｍｇ／ｍＬであった。 0.1 mL of the test solution described above was dropped on the evaluator's tongue, and the limit concentration at which bitterness was felt was examined. Evaluators (examiners) were six women in their twenties.
As a result of the evaluation, six women felt bitterness at any of 0.015 to 0.063 mg / mL for Compound 1. On the other hand, the lowest concentration at which bitterness was felt in purified shellac GSN was 0.250 to 0.500 mg / mL.
　このことから、上記（１．苦味成分の単離）の操作において、苦味成分を抽出したことを確認した。
　３．化合物１（苦味成分）の同定およびセラックにおける化合物１の含有量の測定
　３－１．化合物１の同定
　上記（１．苦味成分の単離）にて得られた化合物１の物理・化学的性質を以下の（Ａ）～（Ｄ）に挙げる。
（Ａ）外観：白色粉末
（Ｂ）質量分析スペクトル：Applied Biosystems製３２００Q  TRAP装置を用い、ESIネガティブモードにて分析　ｍ／ｚ＝５６５．４[M－H]。
（Ｃ）ＴＬＣにおけるＲｆ値：溶媒Ｒｆ値
メタノール：ジクロロメタン＝１：４（ｖ／ｖ）　０．３３（シリカゲル）
（Ｄ）核磁気共鳴分光法（NMR）スペクトル：日本電子（株）製JNM－LA３００装置を用い、重メタノールを内部標準として（δ，ｐｐｍ＝３．３）用いてCD3OD：D2O=１：１（ｖ／ｖ）中で記録されるNMRスペクトル、（ｓ＝一重項；ｄ＝二重項；ｔ＝三重項；ｂｒｄ＝ブロードダブレットｍ＝多重項）、３００MHｚにおいて記録される１H－NMR（δ，ｐｐｍ）：９．７０　ｄ，６．２７　ｄ，５．９１　ｄ，５．８３　ｄ，４．４７　ｄ，４．４３　ｄ，３．５５　ｔ，３．４０－３．３７　ｍ，３．１１　ｄ，２．７１－２．６５　ｍ，２．４２－２．３６　ｍ，２．０３　ｂｒｄ，２．０５－１．９７　ｍ，１．９０－１．７４　ｍ，１．６１－１．３１　ｍ，１．１３　ｓ（図４）；７５．４７MHｚにおいて記録される１３C－NMR（δ，ｐｐｍ）：１７７．２，１７７．０，１７６．３，１４５．７，１３１．５，１０１．３，１０１．１，７９．２，７９．０，７５．０，７０．１，６２．８，５８．２，５８．１，５４．２，５４．１，３６．９，３５．４，３４．０，３２．８，３０．１，２９．９，２９．７，２９．６，２５．７，２５．１，１９．８（図５）。 From this, it was confirmed that the bitter component was extracted in the above operation (1. Isolation of bitter component).
3. 3. Identification of compound 1 (bitter component) and measurement of content of compound 1 in shellac 3-1. Identification of Compound 1 The physical and chemical properties of Compound 1 obtained in the above (1. Isolation of bitter components) are listed in (A) to (D) below.
(A) Appearance: White powder (B) Mass spectrometry spectrum: Analysis in ESI negative mode using 3200Q TRAP apparatus manufactured by Applied Biosystems m / z = 565.4 [M−H].
(C) Rf value in TLC: solvent Rf value methanol: dichloromethane = 1: 4 (v / v) 0.33 (silica gel)
(D) Nuclear magnetic resonance spectroscopy (NMR) spectrum: CD 3 OD: D 2 O using JNM-LA300 apparatus manufactured by JEOL Ltd. and using heavy methanol as internal standard (δ, ppm = 3.3) NMR spectrum recorded in 1: 1 (v / v), (s = singlet; d = doublet; t = triplet; brd = broad doublet m = multiplet), 1H recorded at 300 MHz -NMR (δ, ppm): 9.70 d, 6.27 d, 5.91 d, 5.83 d, 4.47 d, 4.43 d, 3.55 t, 3.40-3.37 m, 3.11 d, 2.71-2.65 m, 2.42-2.36 m, 2.03 brd, 2.05-1.97 m, 1.90-1.74 m, 1. 61-1.31 m, 1.13 s (FIG. 4); 13 C-NMR (δ, ppm) recorded at 75.47 MHz: 177.2, 177. 0, 176.3, 145.7, 131.5, 101.3, 101.1, 79.2, 79.0, 75.0, 70.1, 62.8, 58.2, 58.1, 54.2, 54.1, 36.9, 35.4, 34.0, 32.8, 30.1, 29.9, 29.7, 29.6, 25.7, 25.1, 19 .. 8 (FIG. 5).
　重メタノールを用いたためアルデヒド基はヘミアセタールとの平衡状態にあり、それらの混合物としてのスペクトルを表記した。
　これらの分析結果から、化合物１をJalaric acid（ジャラール酸）とAleuritic acid（アレウリチン酸）から成るエステルであると同定した。 Since heavy methanol was used, the aldehyde group was in an equilibrium state with hemiacetal, and the spectrum as a mixture thereof was shown.
From these analysis results, Compound 1 was identified as an ester composed of Jalaric acid and Aleuritic acid.
　３－２．LC／MS－MSによるセラック中の化合物１の含有量測定
　LC／MS－MSは、液体クロマトグラフィー装置（島津製作所製）に接続したマススペクトロメータ（Applied Biosystems製）を用い、ESI法で測定した。LCおよびMSの測定条件を
下記表１に示す。 3-2. Content measurement of compound 1 in shellac by LC / MS-MS LC / MS-MS was measured by ESI method using a mass spectrometer (manufactured by Applied Biosystems) connected to a liquid chromatography apparatus (manufactured by Shimadzu Corporation). . The measurement conditions for LC and MS are shown in Table 1 below.
Figure JPOXMLDOC01-appb-T000001
 　Jalaric acidとAleuritic acidから成るエステル（化合物１）のMS測定を行うと、ｍ／ｚ５６５．４に前駆イオンが検出された。この前駆イオンについてさらにMS測定を行うと、ｍ／ｚ２６１．２に強いスペクトルが得られた。
Figure JPOXMLDOC01-appb-T000001
 When MS measurement of ester (compound 1) consisting of Jalaric acid and Aleuritic acid was performed, a precursor ion was detected at m / z 565.4. When MS was further measured for this precursor ion, a spectrum strong at m / z 261.2 was obtained.
　ｍ／ｚ５６５．４を前駆イオンとして、ｍ／ｚ２６１．２を生成イオンとしてLC／MS－MS測定を行い、図６のような検量線を得ることができた。なお、精製セラックＧＳＮ中の化合物１を定量すると、９．８２重量％含まれていた。 LC / MS-MS measurement was performed using m / z 565.4 as a precursor ion and m / z 261.2 as a product ion, and a calibration curve as shown in FIG. 6 was obtained. In addition, when compound 1 in purified shellac GSN was quantified, it was found to be 9.82% by weight.
　４．苦味成分含有量を調整したセラックの製造 4. Manufacture shellac with adjusted bitterness content
　精製セラックＧＳＮ１０ｇに酢酸エチル１００ｍＬを加え、還流下で３０分間撹拌した後室温まで冷却した。１時間静置した後、上清をデカンテーションにて除いた。残った沈殿に、再び酢酸エチル１００ｍＬを加え、還流下で３０分間撹拌した。室温まで冷却した後１時間静置し、上清をデカンテーションにて除いた。 100 mL of ethyl acetate was added to 10 g of purified shellac GSN, stirred under reflux for 30 minutes, and then cooled to room temperature. After standing for 1 hour, the supernatant was removed by decantation. 100 mL of ethyl acetate was again added to the remaining precipitate, and the mixture was stirred for 30 minutes under reflux. After cooling to room temperature, the mixture was allowed to stand for 1 hour, and the supernatant was removed by decantation.
　得られた上清を合わせ濃縮、真空乾燥し、３．７ｇの画分（Ｆｒ．１）を得た。また、沈殿を減圧濃縮、真空乾燥し、６．２ｇの画分（Ｆｒ．２）を得た。
　Ｆｒ．１を、できるだけ少量のメタノールに溶解し、コスモシール　７５C18－OPN（商品名，ナカライテスク株式会社製）３００ｍＬを充填したカラムに負荷した後、メタノール：水＝４：１の溶媒にて溶出した。これを減圧濃縮、真空乾燥し、１．３ｇの画分（Ｆｒ．３）を得た。続いてカラムをメタノールにて溶出し、得られた溶出液を減圧濃縮、真空乾燥し、２．４ｇの画分（Ｆｒ．４）を得た。 The obtained supernatants were combined, concentrated and vacuum dried to obtain 3.7 g of a fraction (Fr.1). The precipitate was concentrated under reduced pressure and dried under vacuum to obtain 6.2 g of fraction (Fr. 2).
Fr. 1 was dissolved in as little methanol as possible and loaded on a column packed with 300 mL of Cosmo Seal 75C 18 -OPN (trade name, manufactured by Nacalai Tesque), and then eluted with a solvent of methanol: water = 4: 1. . This was concentrated under reduced pressure and vacuum dried to obtain 1.3 g of a fraction (Fr. 3). Subsequently, the column was eluted with methanol, and the resulting eluate was concentrated under reduced pressure and dried under vacuum to obtain 2.4 g of a fraction (Fr. 4).
　Ｆｒ．２、Ｆｒ．４を一まとめにして、苦味成分を低減したセラック（便宜上セラックＡと称する）を製造した。
　５．苦味成分含有量を調整したセラックの評価
　実施例１で作成したセラックＡをエタノールにて溶解し、１００ｍｇ／ｍＬの溶液を作成した。この溶液を便宜上溶液Ｂと称する。LC／MS－MSを用いてセラックＡにおける化合物１の含有量（含有率）を測定した所、１．７４重量％であることが分かった。 Fr. 2, Fr. 4 was collected together to produce shellac (referred to as shellac A for convenience) with reduced bitterness components.
5. Evaluation of shellac with adjusted bitterness component content Shellac A prepared in Example 1 was dissolved in ethanol to prepare a 100 mg / mL solution. This solution is referred to as Solution B for convenience. When the content (content ratio) of Compound 1 in shellac A was measured using LC / MS-MS, it was found to be 1.74% by weight.
　上記溶液Ｂ（１ｍＬ）に４ｖｏｌ％エタノール９９ｍＬを加え、セラックＡが１ｍｇ／ｍＬの濃度となる５ｖｏｌ％エタノール溶液を作成した。この溶液を便宜上溶液Ｃと称する。溶液Ｃに単離した化合物１を添加し、化合物１の含有率が３．２５重量％となる溶液（試験例１）、３．５０重量％となる溶液（試験例２）、３．７５重量％となる溶液（試験例３）、４．００重量％となる溶液（試験例４）、４．２５重量％となる溶液（試験例５）、４．５０重量％となる溶液（試験例６）を作成した。なお、ここで言う化合物１の含有率とは、溶液中の含有率ではなく、セラック単体（セラックＡ＋化合物１）に換算した場合の化合物１の含有率である。 99% 4vol% ethanol was added to the above solution B (1mL) to prepare a 5vol% ethanol solution with shellac A concentration of 1mg / mL. This solution is referred to as Solution C for convenience. The isolated compound 1 is added to the solution C, and the content of the compound 1 becomes 3.25% by weight (Test Example 1), the solution becomes 3.50% by weight (Test Example 2), 3.75% by weight % Solution (Test Example 3), 4.00% by weight solution (Test Example 4), 4.25% by weight solution (Test Example 5), 4.50% by weight solution (Test Example 6) )created. In addition, the content rate of the compound 1 said here is not the content rate in a solution but the content rate of the compound 1 at the time of converting into shellac single-piece | unit (shellac A + compound 1).
　作成した各試験溶液０．１ｍＬを評価者の舌の上に垂らし、苦味を感じる始める限界濃度を調べた。評価者（試験官）は２０代の女性８名と２０～３０代の男性９名とした。結果を表２に示す。 The 0.1 mL of each prepared test solution was dropped on the evaluator's tongue, and the limit concentration at which bitterness was felt was examined. The evaluators (examiners) were 8 women in their 20s and 9 men in their 20s and 30s. The results are shown in Table 2.
Figure JPOXMLDOC01-appb-T000002
 　以上の結果より、セラック中の化合物１の含有率が４．０重量％以下となれば苦味が十分に低減されることが分かった。さらに、３．５重量％以下であれば苦味の低減がより顕著となる。なお、溶液Ｃ（セラック単体中の化合物１の含有率１．７４重量％）、および溶液Ｃに単離した化合物１を添加し、化合物１の含有率を２．０重量％とした溶液についても、苦味を感じることはできなかった。
Figure JPOXMLDOC01-appb-T000002
 From the above results, it was found that the bitterness was sufficiently reduced when the content of Compound 1 in shellac was 4.0% by weight or less. Furthermore, if it is 3.5 weight% or less, the reduction of bitterness will become more remarkable. In addition, the solution C (content ratio of compound 1 in shellac simple substance 1.74% by weight) and the solution in which the isolated compound 1 was added to solution C and the content ratio of compound 1 was 2.0% by weight were also applied. I couldn't feel any bitterness.
　６．苦味成分を低減したセラックを使用した飲食品・医薬品の製造
　本発明の苦味成分を低減したセラックを用いて、さまざまな飲食品および医薬品を製造することができる。 6). Manufacture of foods and beverages and pharmaceuticals using shellac with reduced bitterness components Various foods and beverages and pharmaceuticals can be manufactured using shellac with reduced bitterness components of the present invention.
　例えば、上記セラックを有効成分とする呈味改善剤を一般的な飲食品に添加して、呈味を改善することができる。なお、飲食品に添加する場合にはセラックをエタノール等のアルコール溶媒に溶解させて用いるとよい。もちろん、粉砕して個体のまま添加してもよい。 For example, a taste improver containing the above shellac as an active ingredient can be added to a general food or drink to improve the taste. In addition, when adding to food-drinks, it is good to use shellac dissolved in alcohol solvents, such as ethanol. Of course, it may be crushed and added as a solid.
　また、上記セラックを含有するコーティング用組成物によって食品および医薬品をコーティングすることができる。従来セラックを含有する組成物による食品等のコーティングは行われているが、本発明のセラックを用いることで苦味を低減することができる。また、材料となるセラックを本発明のセラックに変更するだけでよく、従来の設備を変更せずに用いてコーティングを実行することができる。 Also, foods and pharmaceuticals can be coated with the coating composition containing the shellac. Conventionally, foods and the like are coated with a composition containing shellac, but bitterness can be reduced by using the shellac of the present invention. Moreover, it is only necessary to change the shellac as a material to the shellac of the present invention, and the coating can be performed using the conventional equipment without changing.
　本発明のセラックを用いた飲食品・医薬品の製造実施例を以下に示すが、本発明はこれに限定されるものではない。例えばサプリメントへのセラックの添加、表面コーティングなどにも用いることができる。 Examples of production of foods and beverages and pharmaceuticals using the shellac of the present invention are shown below, but the present invention is not limited thereto. For example, it can be used for addition of shellac to a supplement, surface coating, and the like.
　実施例１にて作成したセラックＡを、９９ｖｏｌ％のエタノールに溶解して、１００ｍｇ／ｍＬの呈味改善剤（α液）を製造した。
　このα液をウイスキーに添加して、呈味を改善したウイスキーを製造した。 Shellac A prepared in Example 1 was dissolved in 99 vol% ethanol to produce a 100 mg / mL taste improver (α solution).
This α liquid was added to whiskey to produce whiskey with improved taste.
　実施例１にて作成した苦味成分を低減したセラックＡをエタノールに溶解し、ボール状のチョコレートをコーティングした後乾燥させて、苦味成分を低減したセラックによりコーティングされたチョコレートを製造した。また、比較例として、精製セラックＧＳＮをエタノールに溶解し、ボール状のチョコレートをコーティングした後乾燥させて、精製セラックＧＳＮによりコーティングされたチョコレートを製造した。 Example 1 Shellac A with reduced bitterness components prepared in Example 1 was dissolved in ethanol, coated with ball-shaped chocolate, and then dried to produce chocolate coated with shellac with reduced bitterness components. In addition, as a comparative example, purified shellac GSN was dissolved in ethanol, coated with ball-shaped chocolate, and then dried to produce chocolate coated with purified shellac GSN.
　これらのチョコレートを一粒食べて、どちらがおいしく感じたか評価を行った。評価者（試験官）は２０代の女性６名と２０～３０代の男性６名とした。結果を表３に示した。 Eating a piece of these chocolates and evaluating which tasted delicious. The evaluators (examiners) were 6 women in their 20s and 6 men in their 20s and 30s. The results are shown in Table 3.
Figure JPOXMLDOC01-appb-T000003
 　男女とも精製セラックＧＳＮをコーティングしたチョコレートの方がおいしいと感じた評価者はおらず、違いが分からない、もしくは、セラックＡをコーティングしたチョコレートの方がおいしく感じたと答えた。以上のことから、苦味成分を低減していないセラックをコーティングしたチョコレートに比べ、苦味成分を低減したセラックをコーティングしたチョコレートは呈味が良好であった。
Figure JPOXMLDOC01-appb-T000003
 There were no evaluators who felt that chocolate coated with refined shellac GSN was more delicious for both men and women, and the difference was not understood, or that chocolate coated with shellac A felt more delicious. From the above, the chocolate coated with shellac with reduced bitterness component had better taste than the chocolate coated with shellac without reduced bitterness component.
　実施例１にて作成したセラックＡをエタノールに溶解し、その溶液にて糖衣掛チョコレートをコーティングした後乾燥させて、セラックによりコーティングされた糖衣掛チョコレートを製造した。 The shellac A prepared in Example 1 was dissolved in ethanol, and the sugar-coated chocolate was coated with the solution and then dried to produce sugar-coated chocolate coated with shellac.
　実施例１にて作成したセラックＡをエタノールに溶解し、その溶液にて板状のチョコレートをコーティングした後乾燥させて、セラックによりコーティングされたチョコレートを製造した。 Example 1 Shellac A prepared in Example 1 was dissolved in ethanol, a plate-shaped chocolate was coated with the solution, and then dried to produce chocolate coated with shellac.
　実施例１にて作成したセラックＡをエタノールに溶解し、その溶液にてチョコレート掛ビスケットをコーティングした後乾燥させて、セラックによりコーティングされたチョコレート掛ビスケットを製造した。 The shellac A prepared in Example 1 was dissolved in ethanol, and the chocolate-coated biscuits were coated with the solution and then dried to produce chocolate-coated biscuits coated with shellac.
　実施例１にて作成したセラックＡをエタノールに溶解し、その溶液にてチョコレート掛コーンフレークをコーティングした後乾燥させて、セラックによりコーティングされたチョコレートコーンフレークを製造した。 The shellac A prepared in Example 1 was dissolved in ethanol, and the chocolate-coated corn flakes were coated with the solution and dried to produce chocolate corn flakes coated with shellac.
　実施例１にて作成したセラックＡをエタノールに溶解し、その溶液にてチョコレート掛乾燥イチゴをコーティングした後乾燥させて、セラックによりコーティングされたチョコレート掛乾燥イチゴを製造した。 The shellac A prepared in Example 1 was dissolved in ethanol, and the chocolate-coated dry strawberry was coated with the solution and dried to produce a chocolate-coated dry strawberry coated with shellac.
　実施例１にて作成したセラックＡをエタノールに溶解し、その溶液にて糖衣ガムをコーティングした後乾燥させて、セラックによりコーティングされた糖衣ガムを製造した。 The shellac A prepared in Example 1 was dissolved in ethanol, and the sugar-coating gum was coated with the solution and then dried to produce sugar-coating gum coated with shellac.
　実施例１にて作成したセラックＡをエタノールに溶解し、その溶液にてグミをコーティングした後乾燥させて、セラックによりコーティングされたグミを製造した。 The shellac A prepared in Example 1 was dissolved in ethanol, the gummi was coated with the solution, and then dried to produce a gummi coated with shellac.
　実施例１にて作成したセラックＡをエタノールに溶解し、その溶液にて焼き海苔をコーティングした後乾燥させて、セラックによりコーティングされた焼き海苔を製造した。 Shellac A prepared in Example 1 was dissolved in ethanol, baked laver was coated with the solution, and dried to produce baked laver coated with shellac.
　実施例１にて作成したセラックＡをエタノールに溶解し、その溶液にてチーズをコーティングした後乾燥させて、セラックによりコーティングされたチーズを製造した。 Example 1 Shellac A prepared in Example 1 was dissolved in ethanol, cheese was coated with the solution, and then dried to produce cheese coated with shellac.
　実施例１にて作成したセラックＡをエタノールに溶解し、その溶液にてむき栗をコーティングした後乾燥させて、セラックによりコーティングされたむき栗を製造した。 Shellac A prepared in Example 1 was dissolved in ethanol, peeled chestnut was coated with the solution, and dried to produce peeled chestnut coated with shellac.
　実施例１にて作成したセラックＡをエタノールに溶解し、その溶液にてソフト掛ゼリーをコーティングした後乾燥させて、セラックによりコーティングされたソフト掛ゼリーを製造した。 The shellac A prepared in Example 1 was dissolved in ethanol, and a soft hanging jelly was coated with the solution and dried to produce a soft hanging jelly coated with shellac.
　実施例１にて作成したセラックＡをエタノールに溶解し、その溶液にてソフト掛キャンディーをコーティングした後乾燥させて、セラックによりコーティングされたソフト掛キャンディーを製造した。 Example 1 Shellac A prepared in Example 1 was dissolved in ethanol, and a soft hanging candy was coated with the solution and dried to produce a soft hanging candy coated with shellac.
　実施例１にて作成したセラックＡをエタノールに溶解し、その溶液にてチョコレート掛レーズンをコーティングした後乾燥させて、セラックによりコーティングされたチョコレート掛レーズンを製造した。 The shellac A prepared in Example 1 was dissolved in ethanol, and the solution was coated with chocolate raisins and dried to produce a chocolate raisins coated with shellac.
　実施例１にて作成したセラックＡをエタノールに溶解し、その溶液にてチョコレート掛クッキーをコーティングした後乾燥させて、セラックによりコーティングされたチョコレート掛クッキーを製造した。 The shellac A prepared in Example 1 was dissolved in ethanol, and the chocolate-coated cookie was coated with the solution and then dried to produce a chocolate-coated cookie coated with shellac.
　実施例１にて作成したセラックＡをエタノールに溶解し、その溶液にて経口投与用の固形製剤をコーティングした後乾燥させて、セラックによりコーティングされた固形製剤を製造した。 The shellac A prepared in Example 1 was dissolved in ethanol, and a solid preparation for oral administration was coated with the solution and then dried to produce a solid preparation coated with shellac.
　７．苦味成分を低減したセラックのアルコール飲料における風味向上効果の検証
　上記実施例２にて製造したウイスキーの風味を評価した。実施例２にて製造したセラック溶液（α液）０．１ｍＬをウイスキー１０ｍＬに添加し、このウイスキー０．１ｍＬを舌の上に垂らし、風味を評価した。 7). Verification of the effect of improving flavor in alcoholic beverages of shellac with reduced bitterness components The flavor of the whiskey produced in Example 2 was evaluated. 0.1 mL of the shellac solution (α solution) produced in Example 2 was added to 10 mL of whiskey, and 0.1 mL of this whiskey was dropped on the tongue to evaluate the flavor.
　なお、比較例として、脱色セラックＰＥＡＲＬ－Ｎ５（商品名、株式会社岐阜セラツク製造所製）を９９ｖｏｌ％のエタノールに溶解した１００ｍｇ／ｍＬのセラック溶液（β液）と、９９ｖｏｌ％のエタノール（ブランク液）とを準備した。β液およびブランク液０．１ｍＬをウイスキー１０ｍＬに添加し、このウイスキー０．１ｍＬを舌の上に垂らし、風味を評価した。結果を表４に示す。 As a comparative example, decolorized shellac PEARL-N5 (trade name, manufactured by Gifu Serask Manufacturing Co., Ltd.) in 99 vol% ethanol, 100 mg / mL shellac solution (β solution), and 99 vol% ethanol (blank solution) ) And prepared. The β solution and 0.1 mL of the blank solution were added to 10 mL of whiskey, and 0.1 mL of this whiskey was dropped on the tongue to evaluate the flavor. The results are shown in Table 4.
Figure JPOXMLDOC01-appb-T000004
 　表４から分かるように、α液を添加したウイスキーはまろやかさ、甘みが増すのに対して、β液を添加したウイスキーは苦味が増した。ブランク液ではウイスキーの味が変化せず、α液を添加したウイスキーよりは強く、β液を添加したウイスキーよりは弱い苦味を有していた。
Figure JPOXMLDOC01-appb-T000004
 As can be seen from Table 4, whiskey to which the α solution was added increased in mellowness and sweetness, whereas the whiskey to which the β solution was added had increased bitterness. The taste of whiskey did not change in the blank solution, and it had a bitter taste stronger than the whiskey to which the α solution was added and weaker than the whiskey to which the β solution was added.
　このように、苦味成分を低減したセラックではウイスキーの苦味を低減してまろやかさ、甘みが増すように呈味を改善することができた。
　８．セラックの苦味成分を使用した食品の製造
　セラックから除去した苦味成分（化合物１）を用いてさまざまな飲食品を製造することができる。 Thus, in shellac with reduced bitterness components, the taste could be improved so that the bitterness of whiskey was reduced and the mellowness and sweetness increased.
8). Manufacture of the foodstuff which uses the bitterness component of shellac Various food-drinks can be manufactured using the bitterness component (compound 1) removed from shellac.
　例えば、上記化合物１を有効成分とする呈味改善剤を一般的な飲食品に添加して、呈味を改善することができる。化合物１を用いた飲食品の製造実施例を以下に示すが、本発明はこれに限定されるものではない。 For example, a taste improver containing the compound 1 as an active ingredient can be added to a general food or drink to improve the taste. Although the manufacture example of the food / beverage products using the compound 1 is shown below, this invention is not limited to this.
　化合物１を９９ｖｏｌ％のエタノールに溶解し、１００ｍｇ／ｍＬの溶液（γ液）を製造した。このγ液をウイスキーに添加して、呈味を改善したウイスキーを製造した。
　９．苦味成分のアルコール刺激低減効果の検証
　実施例１８にて製造したウイスキーの風味を評価した。実施例１８にて製造した溶液（γ液）０．１ｍＬをウイスキー１０ｍＬに添加し、このウイスキー０．１ｍＬを舌の上に垂らし、感じるアルコールの刺激を評価した。 Compound 1 was dissolved in 99 vol% ethanol to prepare a 100 mg / mL solution (γ solution). This γ liquid was added to whiskey to produce whiskey with improved taste.
9. Verification of Alcohol Stimulation Reduction Effect of Bitter Taste The flavor of the whiskey produced in Example 18 was evaluated. 0.1 mL of the solution (γ liquid) produced in Example 18 was added to 10 mL of whiskey, and 0.1 mL of this whiskey was dropped on the tongue, and the alcohol stimulation felt was evaluated.
　なお、比較例として、γ液の代わりに９９ｖｏｌ％のエタノール（ブランク液）０．１ｍＬをウイスキー１０ｍＬに添加し、このウイスキー０．１ｍＬを舌の上に垂らし、感じるアルコールの刺激を比較した。結果を表５に示す。 In addition, as a comparative example, 0.1 mL of 99 vol% ethanol (blank solution) was added to 10 mL of whiskey instead of γ solution, and 0.1 mL of this whiskey was dropped on the tongue, and the alcohol stimulation felt was compared. The results are shown in Table 5.
Figure JPOXMLDOC01-appb-T000005
 　表５から分かるように、γ液を添加したウイスキーはアルコールの刺激を低減して、ウイスキーの風味を強く感じることができるように呈味を改善することができた。
［発明の効果］
　実施例１のようにセラックを処理することで、苦味を大きく低減したセラックを製造することができた。また、苦味成分を大きく低減したセラックをアルコール飲料に添加することにより、アルコール飲料の呈味を改善することができた。
Figure JPOXMLDOC01-appb-T000005
 As can be seen from Table 5, whiskey to which the γ solution was added was able to reduce the alcohol stimulation and improve the taste so that the whiskey flavor could be felt strongly.
[The invention's effect]
By treating shellac as in Example 1, shellac with greatly reduced bitterness could be produced. Moreover, the taste of alcoholic beverages could be improved by adding shellac with greatly reduced bitterness components to alcoholic beverages.
　また、セラックの苦味成分として抽出される化合物１（Jalaric acidとAleuritic acidから成るエステル）をアルコール飲料に添加することにより、アルコール飲料のアルコール刺激を低減することができた。 In addition, by adding compound 1 (ester consisting of Jalaric® acid and Aleuritic® acid) extracted as a bitter component of shellac to the alcoholic beverage, the alcohol stimulation of the alcoholic beverage could be reduced.

Claims (9)

  1. 　ジャラール酸とアレウリチン酸とのエステル化合物の含有率が４．０重量％以下である
    　ことを特徴とするセラック。     A shellac characterized in that the content of the ester compound of jaralic acid and alleuritic acid is 4.0% by weight or less.
  2. 　前記エステル化合物の含有率が３．５重量％以下である
    　ことを特徴とする請求項１に記載のセラック。     The shellac according to claim 1, wherein a content of the ester compound is 3.5% by weight or less.
  3. 　請求項１または請求項２に記載のセラックを有効成分とする呈味改善剤。 A taste improver comprising the shellac according to claim 1 or 2 as an active ingredient.
  4. 　請求項１または請求項２に記載のセラックが添加されてなる飲食品。 A food or drink comprising the shellac according to claim 1 or 2 added thereto.
  5. 　前記飲食品は、アルコール飲料であることを特徴とする請求項４に記載の飲食品。 The food / beverage product according to claim 4, wherein the food / beverage product is an alcoholic beverage.
  6. 　請求項１または請求項２に記載のセラックを含有する
    　ことを特徴とする食品および医薬品の少なくともいずれか一方に用いるコーティング用組成物。     The coating composition used for at least any one of the foodstuffs and pharmaceuticals characterized by including the shellac of Claim 1 or Claim 2.
  7. 　ジャラール酸とアレウリチン酸とのエステル化合物を有効成分とした呈味改善剤。 Taste improving agent comprising an ester compound of jaralic acid and alleuritic acid as an active ingredient.
  8. 　ジャラール酸とアレウリチン酸とのエステル化合物が添加されてなる飲食品。 Food and drink made by adding an ester compound of jaralic acid and alleuritic acid.
  9. 　前記飲食品は、アルコール飲料であることを特徴とする請求項８に記載の飲食品。 The food / beverage product according to claim 8, wherein the food / beverage product is an alcoholic beverage.
PCT/JP2011/070063 2011-09-02 2011-09-02 Shellac, taste-improving agent, food, drink and coating composition WO2013031022A1 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
JP2013530990A JP5665998B2 (en) 2011-09-02 2011-09-02 Shellac, taste improver, food and drink, and coating composition
PCT/JP2011/070063 WO2013031022A1 (en) 2011-09-02 2011-09-02 Shellac, taste-improving agent, food, drink and coating composition

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/JP2011/070063 WO2013031022A1 (en) 2011-09-02 2011-09-02 Shellac, taste-improving agent, food, drink and coating composition

Publications (1)

Publication Number Publication Date
WO2013031022A1 true WO2013031022A1 (en) 2013-03-07

Family

ID=47755567

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2011/070063 WO2013031022A1 (en) 2011-09-02 2011-09-02 Shellac, taste-improving agent, food, drink and coating composition

Country Status (2)

Country Link
JP (1) JP5665998B2 (en)
WO (1) WO2013031022A1 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20140234492A1 (en) * 2011-10-06 2014-08-21 Meiji Co., Ltd. Coated confectionery

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH08311405A (en) * 1995-05-17 1996-11-26 Gifu Seratsuku Seizosho:Kk Shellac coating material
JP2005027651A (en) * 2002-11-29 2005-02-03 Freunt Ind Co Ltd Aqueous shellac coating, method for producing the coating, coated food, method for producing the food, coated pharmaceutical, and method for producing the pharmaceutical
JP2006262763A (en) * 2005-03-23 2006-10-05 Ajinomoto Co Inc Thermosetting shellac resin and food containing the thermosetting shellac resin powder

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH08311405A (en) * 1995-05-17 1996-11-26 Gifu Seratsuku Seizosho:Kk Shellac coating material
JP2005027651A (en) * 2002-11-29 2005-02-03 Freunt Ind Co Ltd Aqueous shellac coating, method for producing the coating, coated food, method for producing the food, coated pharmaceutical, and method for producing the pharmaceutical
JP2006262763A (en) * 2005-03-23 2006-10-05 Ajinomoto Co Inc Thermosetting shellac resin and food containing the thermosetting shellac resin powder

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
HITOSHI MIZUTANI ET AL., CONVERTECH, vol. 30, no. 11, 2002, pages 41 - 45 *
SUKH DEV ET AL., TETRAHEDRON, vol. 30, 1974, pages 867 - 874 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20140234492A1 (en) * 2011-10-06 2014-08-21 Meiji Co., Ltd. Coated confectionery
US10143216B2 (en) * 2011-10-06 2018-12-04 Meiji Co., Ltd. Coated confectionery

Also Published As

Publication number Publication date
JPWO2013031022A1 (en) 2015-03-23
JP5665998B2 (en) 2015-02-04

Similar Documents

Publication Publication Date Title
WO2019071187A1 (en) Stabilized steviol glycoside compositions and uses thereof
JPH07213251A (en) Health food and drink containing antioxidant substance and production of antioxidant substance
WO1999024447A1 (en) Drugs, foods or drinks with the use of algae-derived physiologically active substances
US20190281871A1 (en) Chicory products containing cannabinoids
US20040086553A1 (en) Foods and beverages for whitening and orally administered whitening agents
JP2008088102A (en) Glycosylation inhibitor
CN109641929A (en) Steviol glycoside composition for being orally ingested or using
US20100104724A1 (en) Confectionery
JP2011051950A (en) Fat metabolism improver, medicine and food containing fat metabolism improver, and new flavonoid compound
JPWO2019031586A1 (en) Bitter green tea processed product
JP4090861B2 (en) Antioxidants, foods and cosmetics using the same
WO2007001080A1 (en) Beverage/food and pharmaceutical comprising loquat leaf extract
JPWO2014103415A1 (en) Caffeine-reduced cacao composition
JP2008044872A (en) Health food containing isolariciresinol, blood cholesterol-reducing agent and body fat-reducing agent
JP5665998B2 (en) Shellac, taste improver, food and drink, and coating composition
JP5730596B2 (en) EGF production promoter, FGF-2 production promoter, fibronectin production promoter, moisturizing function improver, wrinkle formation inhibitor, and barrier function improver
KR101140648B1 (en) Chocolate containing soybean paste and method for preparing the same
JP2008031076A (en) Adiponectin production enhancer
US20100040713A1 (en) Fat absorption inhibitor and food and drink using the same
CA2959787A1 (en) A compound (ks 513) isolated from pseudolysimachion rotundum var. subintegrum, the composition comprising the same as an active ingredient for preventing or treating allergy disease, inflammatory disease, asthma or chronic obstructive pulmonary disease and the use thereof
JP2001098264A (en) Antioxidant and active-oxygen eliminator
JP6061482B2 (en) Angiotensin II type 1 receptor antagonist and antihypertensive agent
KR101962325B1 (en) Monaca added Red ginseng and manufacturing method thereof
JP6792753B2 (en) Ferulic acid derivative-containing composition and method for producing the same
KR102154092B1 (en) A compostion comprising Torreya nucifera seed extract or its fraction having anti-oxidation or anti-inflammation activity

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 11871592

Country of ref document: EP

Kind code of ref document: A1

ENP Entry into the national phase

Ref document number: 2013530990

Country of ref document: JP

Kind code of ref document: A

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 11871592

Country of ref document: EP

Kind code of ref document: A1