JP2014185105A - Sophorolipid-containing powder composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a sophorolipid-containing powder composition in which bitterness is masked effectively and which is suitable for ingestion.SOLUTION: A sophorolipid-containing powder composition comprises powder obtained by coating sophorolipid powder with (A) a coating layer comprising magnesium salt and/or calcium salt and (B) a coating layer comprising resin.

Description

  The present invention relates to a sophorolipid-containing powder composition suitable for oral consumption, characterized by being coated with sophorolipid powder.

  Sophorolipid, known as one of biosurfactants that are biologically derived surfactants, is a fermentation product obtained from yeast fermentation. The sophorolipid is easily produced by, for example, inoculating yeast in a medium containing a sugar such as glucose and a carbon source such as vegetable oil and fat, and aeration and stirring under mild temperature and pressure conditions. Sophorolipid has been tried to be applied in various fields such as detergents, pharmaceuticals, cosmetics and food because of its high productivity and safety.

  When the sophorolipid powder is used for oral intake as it is, the yeast odor and bitterness are strong, so that it is necessary to mask the bitterness. Regarding odor masking, it has been reported that coating is performed using edible fats and shellac for the purpose of masking the yeast odor (Patent Document 1). It has also been reported that coating using shellac is a coating method capable of imparting an enteric function in addition to masking of odor and taste (Patent Document 2). However, even when shellac was used for coating of sophorolipid powder, a sufficient masking effect was not obtained.

  In addition, there is an example in which a two-layer coating is performed for the purpose of masking bitterness (Patent Document 3). However, for the sophorolipid powder, even if shellac was coated in two layers, a sufficient bitterness masking effect could not be obtained. Further, when shellac coating was further repeated in order to increase the thickness of the shellac layer, the fluidity of the sophorolipid powder was lowered, and a uniform coating could not be achieved.

JP-A-10-28534 JP 2010-248219 A Special table 2009-514845

  An object of the present invention is to provide a sophorolipid-containing powder composition which is effectively masked in bitterness and suitable for oral intake.

  As a result of intensive studies to solve the above problems, the present inventors have surprisingly found that a plurality of layers are uniformly formed by laminating a coating layer containing magnesium salt and / or calcium salt on a shellac coating layer. The present invention was completed by further finding out that a sufficient masking effect with sufficient bitterness could be obtained, and further studies were made.

That is, the present invention relates to the following inventions.
[1] Sophorolipid-containing powder composition, wherein the sophorolipid powder comprises (A) a coating layer containing a magnesium salt and / or calcium salt and (B) a powder coated with a coating layer containing a resin .
[2] In the above [1], the coating layer is formed by alternately laminating (A) a coating layer containing a magnesium salt and / or a calcium salt and (B) a coating layer containing a resin. The powder composition as described.
[3] The above [1] or [2], wherein the coating layer has (A) a coating layer containing a magnesium salt and / or a calcium salt and (B) a coating layer containing a resin in total of 4 or more layers. ] The powder composition as described in.
[4] The magnesium salt and / or calcium salt is one or more selected from the group consisting of calcium gluconate, shell calcium, calcium hydrogen phosphate, whey calcium, magnesium carbonate and dolomite The powder composition according to any one of [1] to [3].
[5] The powder composition according to any one of [1] to [4], wherein the sophorolipid powder is previously coated with a yeast cell wall.
[6] The powder composition according to any one of [1] to [5], wherein the average particle size is 500 μm or less.
[7] A tablet obtained by tableting the powder composition according to any one of [1] to [6].
[8] (i) A step of coating the sophorolipid powder with a coating material containing magnesium salt and / or calcium salt, and (ii) a step of coating the covering obtained in step (i) with a coating material containing resin. The method for producing a powder composition according to any one of the above [1] to [6], comprising at least a step of:

  The sophorolipid-containing powder composition of the present invention is sufficiently masked in bitterness and suitable for oral intake. Moreover, since it has enteric property, an active ingredient is hard to be decomposed | disassembled. Furthermore, since the sophorolipid-containing powder composition of the present invention is obtained with fine particles, it has excellent absorbability in vivo and is suitable for tableting.

10 is a graph showing the particle size distribution of Test Example 3. The vertical axis represents frequency (%), and the horizontal axis represents mesh opening (μm).

Sophorolipid is a glycolipid composed of sophorose or sophorose partially hydroxylated with hydroxyl group and hydroxyl fatty acid. Sophorose is a sugar composed of two molecules of glucose linked by β1 → 2. A hydroxyl fatty acid is a fatty acid having a hydroxyl group. In addition, sophorolipid is roughly classified into an acid form (general formula (1)) in which a carboxyl group of a hydroxy fatty acid is liberated and a lactone type (general formula (2)) in which sophorose in the molecule is bound. The sophorolipid obtained by yeast fermentation is a mixture of the general formula (1) and the general formula (2), which has different fatty acid chain lengths (R ³ ), sophorose 6 ′ (R ² ) and 6 ″ positions ( There are those obtained as an aggregate of 30 or more structural homologues such as those in which R ¹ ) is acetylated or protonated.

In the general formula (1) or (2), R ⁰ is either hydrogen or a methyl group. R ¹ and R ² are each independently hydrogen or an acetyl group. R ³ is a saturated aliphatic hydrocarbon chain or an unsaturated aliphatic hydrocarbon chain having at least one double bond, and may have one or more substituents. The substituent is not particularly limited as long as it does not impair the effects of the present invention, for example, halogen, hydroxyl, lower _{(C 1 to 6)} alkyl group, a halo-lower _{(C 1 to 6)} alkyl group, hydroxy-lower _{(C 1 6)} alkyl group, a halo-lower _{(C 1 to 6)} alkoxy group, and the like. The number of carbon atoms of ^{R 3} is usually 11 to 20, preferably 13 to 17, more preferably 14 to 16.

  The sophorolipid powder of the present invention is not particularly limited as long as it does not interfere with the effects of the present invention as long as it is a powder containing sophorolipid.For example, the sophorolipid-containing liquid is separated from a culture solution obtained by culturing yeast, and the sophorolipid What is obtained by powdering a containing liquid is preferable. Usually, the sophorolipid-containing liquid obtained by culturing yeast (natural sophorolipid-containing liquid) contains both acid-type sophorolipid and lactone-type sophorolipid. However, from the viewpoint of cost, the mixture is used as it is. It is preferable to use it. In terms of chemical stability, a sophorolipid-containing liquid (acid-type sophorolipid-containing liquid) in which the content of acid-type sophorolipid is increased by a method such as hydrolysis of a lactone-type sophorolipid in a natural-type sophorolipid-containing liquid is used. It is also preferable to use it. The content of the acid type sophorolipid in a preferred embodiment in terms of stability is, for example, preferably about 30% or more, more preferably about 45% or more, and more preferably about 78%, based on the entire sophorolipid. % Or more is more preferable.

  Examples of the yeast include Starmerella (Candida) bombicola, C.I. apicola, C.I. petrophilum, Rhodotorula (Candia), bogoriensis, C.I. batistae, C.I. , and so on. By culturing these yeasts by a known method, sophorolipid is produced. The yeast may be a strain distributed from a storage organization or a strain obtained by subculture thereof. Here, the sophorolipid produced by Rhodotorula (Candia) bogoriensis NRCC9862 is 13-[(2'-O-β-D-glucopyranosyl-β-D-glucopyranosyl) oxy] docosanoic acid 6 ', 6' The hydroxyl group at the center of the alkyl group and a sophorose are linked by glycoside. Although this sophorolipid is different from the general formulas (1) and (2), it is the same in that it is composed of sophorose and hydroxyl fatty acid, and such compounds are also included in the sophorolipid in the present invention.

  As a method for culturing yeast for sophorolipid production, for example, a method of culturing by simultaneously giving a high concentration of sugar and a hydrophobic oily substrate is preferable. Alternatively, the present invention is not limited to this, and widely known methods can be applied as long as the effects of the present invention are not hindered. The known method may be one described in JP-A-2002-045195. Specifically, a technique may be used in which Starmerella (Candida) bombicola is cultured as a production yeast using glucose as a sugar and a carbon source comprising a fatty acid and vegetable oil as a hydrophobic oily substrate.

  The medium composition is not particularly limited, but the fatty acid portion of sophorolipid is known to depend on the fatty acid chain length and the ratio of the hydrophobic substrate to be given, and can be controlled to some extent. As the hydrophobic substrate, for example, oleic acid or a lipid containing a high proportion of oleic acid is suitable. Examples of such lipids include vegetable oils such as palm oil, rice bran oil, rapeseed oil, olive oil and safflower oil, and animal oils such as pork fat and beef tallow. Furthermore, if a mixed substrate of triglyceride and oleic acid is used as the hydrophobic substrate, it is possible to obtain a sophorolipid containing oleic acid in a high ratio with a high yield and yield. From the viewpoint of industrial use, it is required to fermentatively produce sophorolipid with a stable and high yield / yield. In this case, a mixture of hydrophilic sugar and hydrophobic fat as a carbon source is preferable. Glucose is frequently used as the hydrophilic substrate.

  A sophorolipid-containing liquid is obtained from the obtained culture solution by, for example, centrifugation, decantation, and the like, followed by washing with water. The method for recovering the sophorolipid-containing solution from the culture solution by a known method is not particularly limited as long as the effect of the present invention is not hindered, and a known method can be used. As such a method, for example, a method described in Japanese Patent Application Laid-Open No. 2003-9896 may be used. Specifically, in the purification process, the solubility of water in the organic solvent is controlled by changing the pH of the sophorolipid (mixture of the general formulas (1) and (2)) that precipitates in the culture end solution. A natural sophorolipid-containing liquid can be obtained as a water-containing product of about 50% without using any.

  When increasing the content of the acid type sophorolipid in the sophorolipid-containing liquid, the lactone ring of the lactone type sophorolipid may be opened by hydrolysis or the like. A known method can be used for the hydrolysis as long as the effects of the present invention are not hindered. For example, metal salts of hydroxides (sodium, potassium, calcium, magnesium, etc.), carbonates, phosphates, Preferable examples include alkali hydrolysis using a base such as alkanolamine. Further, various catalysts such as alcohol can be used. The temperature, pressure and time for performing the alkaline hydrolysis can be appropriately set as long as the effects of the present invention are not hindered, but the hydrolysis proceeds efficiently and the target product, acid sophorolipid, is decomposed and chemically modified, etc. It is preferable to suppress this side reaction. In this respect, the temperature is usually about 30 ° C to 120 ° C, preferably about 50 ° C to 90 ° C. The pressure is about 1 to 10 atmospheres, preferably about 1 to 2 atmospheres. The time is about 10 minutes to 5 hours, preferably about 1 to 3 hours. Moreover, the time for performing the alkali hydrolysis can be appropriately set depending on the concentration and amount of the sophorolipid-containing liquid.

  In addition, the acid-type sophorolipid-containing liquid used in the present invention is obtained by a fermentation production method that selectively produces only acid-type sophorolipid in one step, as described in, for example, Japanese Patent Application Laid-Open No. 2008-247845. It may be. Moreover, what carried out the alkali process further about what was obtained by the said fermentation production may be used.

  The sophorolipid-containing liquid that is the raw material of the sophorolipid powder of the present invention is preferably a high-purity one from the viewpoint of suppressing an unpleasant odor caused by yeast or the like, and in terms of stability, a high-purity acid type It is more preferable to use a sophorolipid-containing liquid. The method for increasing the purity of the sophorolipid in the sophorolipid-containing liquid is not particularly limited as long as the effect of the present invention is not hindered, and a known method can be used, for example, a method such as chromatography, electrophoresis, ultrafiltration, etc. From the viewpoint of production efficiency, etc., chromatography such as liquid chromatography is particularly preferable.

  The high-purity acid type sophorolipid-containing liquid includes, for example, a step of adjusting the pH of the acid type sophorolipid-containing liquid to an acidic region, and a step of chromatographically separating the acidic acid type sophorolipid-containing liquid obtained in the step Can preferably be obtained. More specifically, the acidic region is preferably less than about pH 6, more preferably about pH 1 to 5, further preferably about pH 1 to 4.5, and particularly preferably about pH 1 to 4. By adjusting the pH to the above range, an acid-type sophorolipid with higher purity and stability can be obtained. Examples of the pH adjuster used here include inorganic acids such as sulfuric acid, hydrochloric acid, nitric acid, phosphoric acid, boric acid and hydrofluoric acid; formic acid, acetic acid, malic acid, citric acid, oxalic acid, glutamic acid and aspartic acid. Organic acids and the like are used.

  The sophorolipid-containing liquid to be subjected to the chromatographic separation preferably has a viscosity of about 5 to 50 mPa · S, more preferably about 5 to 20 mPa · S from the viewpoint of separation efficiency. When the viscosity of the sophorolipid-containing liquid is high, it is preferable to use a liquid whose viscosity is adjusted within the above range. The method for adjusting the viscosity is not particularly limited as long as the effects of the present invention are not hindered, but it is preferably diluted with ethanol and purified water because adverse effects on the human body and the environment are reduced.

  In the chromatography, as a filler (adsorbent) used as a stationary phase, for example, any silica gel, octadecyl silica gel (ODS) resin, ion exchange resin, synthetic adsorbent and the like known in the art are used. The chromatography is preferably reverse phase chromatography from the standpoint that a highly safe one can be selected as the eluent (developing phase). When the chromatography is reverse phase chromatography, it is more preferable to use ODS resin or the like as the filler. By using an ODS resin in which a hydrophobic octadecyl group or the like is chemically modified for the silica gel carrier, a highly pure sophorolipid-containing liquid can be obtained more efficiently by utilizing hydrophobic interaction with the alkyl side chain of sophorolipid. It is preferable from the standpoint of separation efficiency and the like that a solvent having a polarity stronger than that of the packing material is used for the eluent of reverse phase chromatography. As such an eluent, for example, methanol and ethanol are preferable, and ethanol and the like are particularly preferable from the viewpoint of safety.

  If desired, the sophorolipid-containing liquid may be concentrated by distillation or the like before being powdered. Examples of the distillation method include molecular distillation, vacuum distillation, steam distillation and the like, and vacuum distillation is particularly preferable from an industrial viewpoint. The sophorolipid-containing liquid before pulverization preferably has a sophorolipid content of about 50% by mass or less, preferably about 30% by mass or less, from the viewpoint that powdering is easy and a fine powder can be obtained. Is more preferable, and particularly preferably about 20% by mass or less. Further, from the viewpoint of stability and the like, the pH of the sophorolipid-containing liquid may be adjusted before pulverization. The preferred pH value varies depending on the composition of the sophorolipid-containing liquid to be used, but in the case of a natural sophorolipid-containing liquid, it is preferably adjusted to about pH 5 to 9 using a known pH adjusting agent such as sodium bicarbonate. A pH of about 6 to 8 is more preferred, and a pH of about 6.5 to 7.5 is most preferred.

  The method for pulverizing the sophorolipid-containing liquid is not particularly limited as long as the effects of the present invention are not hindered.For example, known methods such as freeze-drying, recrystallization, and spray-drying can be used. In view of efficiency, a spray drying method or the like is preferably used. In the spray drying method, an excipient may or may not be used, but it is preferable not to use an excipient from the viewpoint of obtaining a higher purity sophorolipid powder. The conditions of the spray-drying method are not particularly limited as long as the effects of the present invention are not hindered. However, when the treatment is performed at a high temperature and a high rotation (for example, a temperature of about 100 ° C. or higher, a rotation speed of about 12000 rpm or higher, etc.) A sophorolipid powder that is high and has little fouling can be obtained.

  The sophorolipid powder of the present invention may contain components other than the sophorolipid if desired. Examples of the component include carbohydrates such as dextrin, protein-containing raw materials such as nonfat dry milk, powdered fats and oils, vitamins, minerals, plant sterols, lactic acid bacteria powder, and other powder raw materials that can be used as food. The sophorolipid powder of the present invention is preferably granulated by a known method such as fluidized bed granulation. The granulation is particularly preferably performed using a tumbling fluidized coating apparatus from the viewpoint of excellent powder fluidity. The granulated powder preferably has an average particle size of about 300 μm or less, and more preferably about 200 μm or less. In the present invention, the average particle size is defined as the particle size at which the cumulative weight of the particle size distribution measured by the sieving method reaches 50% by weight.

  The sophorolipid powder of the present invention may be coated with a yeast cell wall (Kirin Kyowa Foods Co., Ltd., yeast wrap, etc.), hydroxypropylmethylcellulose, or the like as desired after granulation. Although the coating method is not particularly limited, it is preferably performed by spraying from the viewpoint of simplicity and the like. Moreover, it is preferable to coat using a fine particle coating apparatus. The sophorolipid powder coated with the yeast cell wall has improved fluidity and is preferably used for the next coating step.

  The sophorolipid-containing powder composition of the present invention comprises a coating layer (hereinafter also referred to as A layer) in which the sophorolipid powder contains (A) a magnesium salt and / or a calcium salt, and (B) a coating layer containing a resin (hereinafter referred to as “a”). It is also characterized by containing a powder coated with (also referred to as B layer).

  The magnesium salt and / or calcium salt in the A layer is not particularly limited as long as the effects of the present invention are not hindered. For example, calcium gluconate, shell calcium, calcium hydrogen phosphate, whey calcium, magnesium carbonate, dolomite, Calcium lactate, calcium citrate, and the like are mentioned, and calcium gluconate, shell calcium, calcium hydrogen phosphate, whey calcium, magnesium carbonate, dolomite, and the like are particularly preferably used from the viewpoint of excellent fluidity during coating. These may be used alone or in combination. Although the coating method is not particularly limited, it is preferable to spray a solution or a dispersion from the viewpoint of simplicity. Moreover, it is preferable to coat using a fine particle coating apparatus. The concentration of the solution or dispersion is not particularly limited as long as the effect of the present invention is not hindered, but is preferably about 0.5% to 20%, and more preferably about 1% to 5%. The solvent or dispersion medium is not particularly limited as long as the effect of the present invention is not hindered, and water, ethanol, glycerin, and the like can be mentioned. From the viewpoint of dispersibility, it is particularly preferable to use water or the like.

  The resin in the B layer is not particularly limited as long as the effects of the present invention are not hindered, and edible resins are widely included. Examples of the resin include a copolymer of methyl methacrylate and methacrylic acid, a copolymer of ethyl acrylate and methacrylic acid, hydroxypropyl methylcellulose phthalate, cellulose acetate phthalate, and shellac. These may be used alone or in combination. Further, if necessary, a plasticizer may be further added to the resin. As the plasticizer, for example, triacetin, macrogol 400, triethyl citrate, Tween 80, castor oil, medium chain fatty acid and the like are used. Although the coating method is not particularly limited, it is preferable to spray a solution or a dispersion from the viewpoint of simplicity. Moreover, it is preferable to coat using a fine particle coating apparatus. The concentration of the solution or dispersion is not particularly limited as long as the effect of the present invention is not hindered, but is preferably about 0.5% to 30%, and more preferably about 1% to 10%. The solvent or dispersion medium is not particularly limited as long as the effect of the present invention is not hindered, and examples thereof include water, ethanol, glycerin, and the like, but ethanol is particularly preferable from the viewpoint of solubility.

  In the present invention, the coating of either the A layer or the B layer may be performed first, but it is preferable to perform the coating of the A layer first because the fluidity of the powder is further ensured. Since the powder has fluidity, uniform coating can be performed even when the coatings are stacked in multiple layers. In order to effectively mask the bitterness, the sophorolipid-containing powder of the present invention preferably has 4 or more coating layers in total of the A layer and the B layer, more preferably 6 layers or more, and even more preferably 10 layers or more. Further, the A layer and the B layer are preferably laminated alternately, and the outermost shell of the coating layer may be either the A layer or the B layer, but the B layer is preferable from the viewpoint of appearance. The average particle size of the powder composition after coating is preferably about 500 μm or less, more preferably about 300 μm or less, and further preferably about 200 μm or less.

  Thus, (i) the step of coating sophorolipid powder with a coating material containing magnesium salt and / or calcium salt, and (ii) the coating obtained in step (i) with a coating material containing resin. A method for producing a powder composition having at least a coating step is also included in the present invention.

  When the sophorolipid-containing powder composition of the present invention is orally administered, it may be a solid preparation such as powder, granule, pill, tablet and capsule, or may be a liquid such as syrup, but storage stability etc. From this point, powders, tablets and the like are particularly preferable, and tablets obtained by tableting the powder composition are most preferable from the viewpoints of ease of oral intake and ease of handling. When these preparations are produced, carriers or additives corresponding to the preparation form can be used. In addition to the sophorolipid-containing powder composition of the present invention, the formulation may contain other active ingredients.

  Examples of the carrier or additive include excipients (sodium polyacrylate, calcium polyacrylate, carboxymethylcellulose, lactose, dextrin, corn starch, crystalline cellulose, sucrose, sodium chloride, glucose, urea, starch, calcium carbonate, Kaolin, silicic acid and potassium phosphate, etc.), lubricant (magnesium stearate, calcium stearate, sucrose fatty acid ester, glycerin fatty acid ester, purified talc, polyethylene glycol, etc.), disintegrant (carboxymethylcellulose calcium, anhydrous hydrogen phosphate) Calcium, sodium carboxymethylcellulose, low-substituted hydroxypropylcellulose, dried starch, sodium alginate, agar powder, sodium bicarbonate and calcium carbonate) Compound (hydroxypropyl cellulose, gum arabic solution, water, ethanol, propanol, simple syrup, glucose solution, starch solution, gelatin solution, carboxymethyl cellulose, methyl cellulose, polyvinyl pyrrolidone, etc.), solubilizer (gum arabic and polysorbate 80, etc.) , Absorption enhancers (such as sodium lauryl sulfate), buffers (phosphate buffer, acetate buffer, borate buffer, carbonate buffer, citrate buffer, Tris buffer, etc.), preservatives (methyl parahydroxybenzoate) , Ethyl paraoxybenzoate, propyl paraoxybenzoate, butyl paraoxybenzoate, chlorobutanol, benzyl alcohol, benzalkonium chloride, sodium dehydroacetate and sodium edetate), thickener (propylene glycol, glycerin, hydride) Xylethylcellulose, hydroxypropylcellulose, polyvinyl alcohol, polyethylene glycol, etc.), stabilizers (sodium bisulfite, sodium thiosulfate, sodium edetate, sodium citrate, ascorbic acid, dibutylhydroxytoluene, etc.), pH adjusters (hydrochloric acid, Sodium hydroxide, phosphoric acid, acetic acid, etc.).

(Production Example 1)
As a culture medium, 10 g of glucose per liter (manufactured by Nippon Shokuhin Kako Co., Ltd., product name: eclipse-containing crystal glucose), 10 g of peptone (manufactured by Oriental Yeast Co., Ltd.), 5 g of yeast extract (manufactured by Asahi Food and Healthcare, product name: Using a liquid medium containing mist powder N), Candida bombicola ATCC22214 was shake-cultured at 30 ° C. for 2 days to obtain a preculture solution.
This preculture is inoculated into a main culture medium (3 L) charged in a 5 L fermentor at a rate of 4% of the charged amount, cultured at 30 ° C. for 6 days under conditions of aeration 0.6 vvm, and fermented. I let you. The composition of the main culture medium is 100 g of glucose per liter, 50 g of palm olein (manufactured by NOF, product name: Permaly 2000), 50 g of oleic acid (manufactured by ACID CHEM, product name: Palmac 760), 1 g of sodium chloride, A medium (pH 4.5 to 4.8 before sterilization) containing 10 g of monopotassium phosphate, 10 g of magnesium sulfate heptahydrate, 2.5 g of yeast extract, and 1 g of urea was used. Fermentation was stopped after 6 days from the start of the culture, the culture solution taken out from the fermenter was heated, returned to room temperature, and allowed to stand for 2 to 3 days, so that a liquid brown precipitate layer, mainly from the bottom, It separated into three layers of milky white solid layer and supernatant that seemed to be cells. After removing the supernatant, industrial water or groundwater was added in the same amount as the removed supernatant. While stirring this, a 48% by mass sodium hydroxide solution was gradually added to a pH of 6.5 to 6.9 to solubilize the sophorolipid contained in the culture solution. This was centrifuged with a tabletop centrifuge (Westphalia: manufactured by Westphalia Separator AG) to precipitate a milky white solid, and the supernatant was collected. While stirring the collected supernatant, 62.5% by mass sulfuric acid was gradually added to adjust the pH to 2.5 to 3.0 to resolubilize the sophorolipid. After leaving this to stand for 2 days, the supernatant was removed as much as possible by decantation, and the residue was obtained as a sophorolipid-containing liquid (water content of about 50%, Production Example Product 1).

(Production Example 2)
Sodium hydroxide was added to the sophorolipid-containing liquid fractionated in Production Example 1 to adjust the pH to 12, followed by hydrolysis (alkali hydrolysis) at 80 ° C. for 2 hours. Subsequently, the insoluble matter generated after returning to room temperature was removed by filtration, and the filtrate was adjusted to pH 3.2 using sulfuric acid (9.8 M aqueous solution). This was subjected to reverse phase column chromatography (Cosmosil 40C18-PREP, Nacalai Tesque, 5 kg). Specifically, 3 L of acid-type sophorolipid-containing liquid prepared to pH 3.2 (about 3% by mass as ethanol-soluble component with respect to the stationary phase filling amount) was added, and then 20 L of mobile phase of 10% ethanol aqueous solution was added. Then, 35 L of a mobile phase of 50% ethanol aqueous solution was used to elute and remove odors and salts as water-soluble impurities and some pigment substances. Then, the target acid type sophorolipid was eluted from the resin with 30 L of a mobile phase of 70% ethanol aqueous solution. The obtained high-purity acid sophorolipid-containing liquid was a colorless and transparent solution having an acid sophorolipid concentration of 1 mass%, a pH of 3.3, an ethanol concentration of 70%, a viscosity of 15.3 mPa · s, and an ethanol odor (Production Example) Product 2). The ethanol-soluble matter described here indicates the amount of a substance that is dissolved in ethanol by dissolving the sample in ethanol. The “ethanol-soluble matter (%)” can be measured according to JIS K3362-2008.

(Production Example 3)
The high-purity acid-type sophorolipid-containing liquid (Production Example Product 1) was distilled with an evaporator (Toyo Chemical Food Plant). The obtained concentrated liquid was a colorless and transparent solution having an acid-type sophorolipid concentration of 15%, pH 3.3, an ethanol concentration of 5% or less, a viscosity of 10.2 mPa · s, and an ethanol odor. The concentrated solution was pulverized with a spray dryer (dry powderizer) (SUS304 R-3 type, water evaporation capacity MAX 5 kg / h, manufactured by Sakamoto Giken Co., Ltd.). The spray drying conditions were an atomizer of 12,000 rpm and a bath temperature of 105 ° C.

Example 1
Fluidized bed granulation was performed on 200 g of the powder obtained in Production Example 3 while spraying 200 mL of water with a tumbling fluidized coating apparatus (MP-01, manufactured by Pauleck Co., Ltd.) to obtain a sophorolipid granulated product. The unit of MP-01 was replaced with a fine particle coating unit, and 150 g of the sophorolipid granulated material was coated so that there were 5 layers alternately in the order of the dolomite layer and the shellac layer (a total of 10 layers). For each coating, the dolomite layer was prepared by dispersing dolomite (dolomite W manufactured by Meiji Food Materia Co., Ltd.) with water to a concentration of 2.5% by mass and spraying 90 g. The shellac layer was sprayed with 140 g of shellac (shellac concentration 32% by mass, rack glaze 32E-N Japan shellac) diluted with ethanol to give 5% by mass shellac (shellac concentration 1.6% by mass).

(Example 2)
The powder of Example 1 was changed to a mixture of 20 g of the powder obtained in Production Example 3 and 180 g of dextrin (Paindex # 2 manufactured by Matsutani Chemical Co., Ltd.).

(Example 3)
20 g of the powder obtained in Production Example 3 and 180 g of dextrin (Paindex # 2 manufactured by Matsutani Chemical Co., Ltd.) were mixed. Fluidized bed granulation was carried out while spraying 200 mL of water with a tumbling fluidized coating apparatus (MP-01, manufactured by Paulek). The unit of MP-01 was replaced with a fine particle coating unit, and 150 g of the sophorolipid granule obtained was sprayed with 180 g of yeast cell wall (yeast wrap solid content: 8.5% by mass, Kirin Kyowa Foods Co., Ltd.) to carry out coating. A yeast cell wall coating was obtained. Coating was performed on 150 g of the yeast cell wall coating so that there were 5 layers alternately in the order of the dolomite layer and the shellac layer (a total of 10 layers). For each coating, the dolomite layer was prepared by dispersing dolomite (dolomite W manufactured by Meiji Food Materia Co., Ltd.) with water to a concentration of 2.5% by mass and spraying 90 g. The shellac layer was sprayed with 140 g of shellac (shellac concentration 32% by mass, rack glaze 32E-N Japan shellac) diluted with ethanol to give 5% by mass shellac (shellac concentration 1.6% by mass).

Example 4
Coating was carried out on 150 g of the sophorolipid powder obtained in Production Example 3 in an order of 5 layers each in the order of shellac layer and dolomite layer (a total of 10 layers). For each coating, the shellac layer was diluted with shellac (shellac concentration 32% by mass, rack glaze 32E-N Japan shellac) to 5% shellac (shellac concentration 1.6% by mass) and sprayed with 140 g. The dolomite layer was prepared by dispersing dolomite (dolomite W manufactured by Meiji Food Materia Co., Ltd.) with water to a concentration of 2.5% by mass and spraying 90 g.

(Example 5)
150 g of the yeast cell wall coating obtained by the method described in Example 3 was coated in a shellac layer and a dolomite layer in this order so that there were 5 layers each (total 10 layers). For each coating, the shellac layer was diluted with shellac (shellac concentration 32% by mass, rack glaze 32E-N Japan shellac) with ethanol to give 5% shellac (shellac concentration 1.6% by mass) and sprayed 140 g. The dolomite layer was prepared by dispersing dolomite (dolomite W manufactured by Meiji Food Materia Co., Ltd.) with water to a concentration of 2.5% by mass and spraying 90 g.

(Example 6)
Coating was carried out by changing the dolomite of Example 3 to milk calcium (milk calcium CA-28 manufactured by Morinaga Milk Industry Co., Ltd.).

(Example 7)
Coating was carried out by changing the dolomite of Example 3 to shell unfired calcium (shell powder manufactured by Meiji Food Materia Co., Ltd.).

(Example 8)
Coating was carried out by changing the dolomite of Example 3 to calcium monohydrogen phosphate (manufactured by Taihei Chemical Industrial Co., Ltd.).

Example 9
Coating was carried out by changing the dolomite of Example 3 to magnesium carbonate (manufactured by Tomita Pharmaceutical Co., Ltd.).

(Example 10)
Coating was carried out by changing the dolomite of Example 3 to calcium gluconate (Pureac).

(Example 11)
In Example 3, coating was performed without using the fine particle coating unit (using a fluidized bed granulator). As a result, it was difficult to carry out the coating of the fifth and subsequent layers while maintaining the fluidity.

(Example 12)
Coating was carried out by changing the dolomite of Example 3 to calcium lactate (manufactured by Fuso Chemical Industries). As a result, it was difficult to carry out the coating of the seventh and subsequent layers while maintaining the fluidity, so that a six-layer coating was made.

(Example 13)
Coating was carried out by changing the dolomite of Example 3 to calcium citrate (manufactured by Fuso Chemical Industries). As a result, it was difficult to carry out the coating of the seventh and subsequent layers while maintaining the fluidity, so that a six-layer coating was made.

(Example 14)
25 g of water was added to 50 g of the natural sophorolipid-containing liquid obtained in Production Example 1 and stirred. Sodium bicarbonate was added to adjust the pH to 7.0, and water was added to 100 g to obtain a neutral natural sophorolipid-containing diluted solution. Neutral natural type sophorolipid-containing diluent 60g was added to 50g of β-cyclodextrin (CAVAMAX® W7 Food cyclochem). After mixing well, lyophilization was carried out using a freeze dryer (VD-800R manufactured by Taitec Co., Ltd.). The obtained dried product was pulverized in a mortar and passed through a 250 μm mesh to obtain a sophorolipid powder.
The sophorolipid powder 150 g was coated so that there were 5 layers alternately in the order of the dolomite layer and the shellac layer (a total of 10 layers). For each coating, the dolomite layer was prepared by dispersing dolomite (dolomite W manufactured by Meiji Food Materia Co., Ltd.) with water to a concentration of 2.5% by mass and spraying 90 g. The shellac layer was sprayed with 140 g of shellac (shellac concentration 32% by mass, rack glaze 32E-N Japan shellac) diluted with ethanol to give 5% by mass shellac (shellac concentration 1.6% by mass).

(Example 15)
50 g of β-cyclodextrin (CAVAMAX® W7 Food cyclochem) was added to 50 g of the acid-type sophorolipid-containing liquid having a pH of 3.2 obtained in Production Example 2. After mixing well, lyophilization was performed. The obtained dried product was pulverized in a mortar and passed through a 250 μm mesh to obtain a sophorolipid powder.
The sophorolipid powder 150 g was coated so that there were 5 layers alternately in the order of the dolomite layer and the shellac layer (a total of 10 layers). For each coating, the dolomite layer was prepared by dispersing dolomite (dolomite W manufactured by Meiji Food Materia Co., Ltd.) with water to a concentration of 2.5% by mass and spraying 90 g. The shellac layer was sprayed with 140 g of shellac (shellac concentration 32% by mass, rack glaze 32E-N Japan shellac) diluted with ethanol to give 5% by mass shellac (shellac concentration 1.6% by mass).

(Comparative Example 1)
A 5 mass% ethanol solution (shellac concentration: 1.6 mass%) of shellac (shellac concentration: 32 mass%, rack glaze 32E-N Japan shellac) was continuously applied to the yeast cell wall coating of Example 3 using a fine particle coating apparatus. Sprayed. As a result, 230 g or more of 5% by mass shellac could not be sprayed due to a decrease in fluidity, and it was difficult to continue the coating. Therefore, the coating was terminated at the time of spraying 230 g.

(Comparative Example 2)
150 g of the yeast cell wall coating obtained by the method described in Example 3 was coated alternately in the order of a shellac layer and a starch layer. For each coating, the shellac layer was diluted with shellac (shellac concentration 32% by mass, rack glaze 32E-N Japan shellac) with ethanol to give 5% shellac (shellac concentration 1.6% by mass) and sprayed 140 g. Moreover, the starch layer disperse | distributed potato starch (Amicol HG-N Nippon Star Chemical Co., Ltd.) to the 2.5 mass% density | concentration with water, and sprayed 90g. As a result, since the third and subsequent layers could not be achieved due to a decrease in fluidity, a two-layer coating was obtained.

(Test Example 1)
For the powders obtained in Examples 1 to 15 and Comparative Examples 1 and 2, a sensory test was conducted with 10 panelists. Specifically, the powder was included in the mouth and held for 30 seconds to evaluate the bitter taste masking effect (Table 1). The evaluation criteria were as follows, and the evaluation with the largest number of people was the result.
A: The bitterness is completely masked and no bitterness is felt.
○: Although bitterness is masked, bitterness is slightly felt.
X: Masking of bitterness is insufficient and bitterness is felt.

  The coating needs to be repeated several times. In order to obtain the masking effect, each of the A layer and the B layer is 2 or more layers (4 layers coating), and each of the 5 layers (10 layers) to completely mask the bitterness. Coating) was repeated with desirable results.

(Test Example 2)
In Example 1, the particle size distribution after the coating of the mixture before granulation, coating of shellac and dolomite W was performed 5 times each was compared. Before granulation, the particles were mainly 100 μm or less, but after coating, the particle distribution changed to 250 μm or less (FIG. 1).

1 Before coating 2 After coating

Claims (8)

  A sophorolipid-containing powder composition, wherein the sophorolipid powder comprises (A) a coating layer containing a magnesium salt and / or calcium salt and (B) a powder coated with a coating layer containing a resin.   The powder composition according to claim 1, wherein the coating layer is formed by alternately laminating (A) a coating layer containing magnesium salt and / or calcium salt and (B) a coating layer containing resin. object.   The powder composition according to claim 1 or 2, wherein the coating layer has a total of four or more coating layers containing (A) a magnesium salt and / or calcium salt and (B) a resin. object.   The magnesium salt and / or calcium salt is at least one selected from the group consisting of calcium gluconate, shell calcium, calcium hydrogen phosphate, whey calcium, magnesium carbonate and dolomite. 4. The powder composition according to any one of 3.   The powder composition according to any one of claims 1 to 4, wherein the sophorolipid powder is previously coated with a yeast cell wall.   The powder composition according to any one of claims 1 to 5, wherein an average particle size is 500 µm or less.   A tablet obtained by tableting the powder composition according to any one of claims 1 to 6.   (I) a step of coating the sophorolipid powder with a coating material containing a magnesium salt and / or a calcium salt, and (ii) a step of coating the covering obtained in the step (i) with a coating material containing a resin. It has at least, The manufacturing method of the powder composition in any one of Claims 1-6 characterized by the above-mentioned.