JP2005263770A - Method for producing powdery 1,5-d-anhydrofructose - Google Patents

Method for producing powdery 1,5-d-anhydrofructose Download PDF

Info

Publication number
JP2005263770A
JP2005263770A JP2004120909A JP2004120909A JP2005263770A JP 2005263770 A JP2005263770 A JP 2005263770A JP 2004120909 A JP2004120909 A JP 2004120909A JP 2004120909 A JP2004120909 A JP 2004120909A JP 2005263770 A JP2005263770 A JP 2005263770A
Authority
JP
Japan
Prior art keywords
anhydrofructose
starch
containing composition
drying
weight
Prior art date
Legal status (The legal status 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 status listed.)
Pending
Application number
JP2004120909A
Other languages
Japanese (ja)
Inventor
Toshiyasu Muroya
賢康 室屋
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sunus Co Ltd
Original Assignee
Nihon Starch Co Ltd
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 Nihon Starch Co Ltd filed Critical Nihon Starch Co Ltd
Priority to JP2004120909A priority Critical patent/JP2005263770A/en
Publication of JP2005263770A publication Critical patent/JP2005263770A/en
Pending legal-status Critical Current

Links

Landscapes

  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Saccharide Compounds (AREA)

Abstract

<P>PROBLEM TO BE SOLVED: To provide a method for readily and inexpensively producing powdery 1,5-D-anhydrofructose. <P>SOLUTION: The method for producing the powdery 1,5-D-anhydrofructose comprises spraying and drying 1,5-D-anhydrofructose-containing composition obtained by mixing 1 pt. wt. 1,5-D-anhydrofructose with 0.2-10.0 pts. wt. degraded starch as a powdery base. <P>COPYRIGHT: (C)2005,JPO&NCIPI

Description

本発明は、粉末化された1,5−D−アンヒドロフルクトースの製造法に関する。  The present invention relates to a process for producing powdered 1,5-D-anhydrofructose.

1,5−D−アンヒドロフルクトース(以下、1,5−AFという)は澱粉の酵素分解によって調製できる糖類であり、他の糖類にない性質を示す。食品に安全に添加される抗酸化剤([特許文献1]参照)、枯草菌および乳酸菌に特に有効な抗菌剤([特許文献2]参照)、澱粉の老化防止剤([特許文献3]参照)、タンパク質等のアミノ化合物への糖供与体([特許文献4]参照)、および食品の着色剤([特許文献5]参照)等として、幅広い応用が検討されている単糖である。また、この単糖は抗生物質ピロンミクロテシンの前駆体でもある([特許文献6]参照)。  1,5-D-anhydrofructose (hereinafter referred to as 1,5-AF) is a saccharide that can be prepared by enzymatic degradation of starch, and exhibits properties not found in other saccharides. Antioxidants that can be safely added to foods (see [Patent Document 1]), antibacterial agents that are particularly effective against Bacillus subtilis and lactic acid bacteria (see [Patent Document 2]), and anti-aging agents for starch (see [Patent Document 3]) ), Sugar donors to amino compounds such as proteins (see [Patent Document 4]), and food coloring agents (see [Patent Document 5]), etc. This monosaccharide is also a precursor of the antibiotic pyrone microthecin (see [Patent Document 6]).

特許文献1では、Morchella costataまたはMorchella vulgaris等の菌類やGracilariopsis lemaneiformis等の藻類からα−1,4−グルカンリアーゼを単離する方法、および、澱粉あるいは澱粉分解物の溶液をα−1,4−グルカンリアーゼで分解することにより1,5−AFを容易かつ安価に、そして大量に製造する方法を開示している。  In Patent Document 1, a method for isolating α-1,4-glucan lyase from fungi such as Morcella costa or Morchella vulgaris and algae such as Gracilariapsis lemaneformis, and a solution of starch or starch degradation product as α-1,4- A method for producing 1,5-AF easily, inexpensively and in large quantities by degrading with glucan lyase is disclosed.

1,5−AFは、さまざまな分野での利用が期待される糖質である。1,5−AFは水溶液の状態では安定性が低く、1,5−AFを含有する製剤の保存において、1,5−AF含有量の経時的な低下、あるいは、製剤自体の着色など製品品質の変化が生じる。その品質変化を低減させるためには、より低温での保存が要求されるが、市場での流通を考慮した場合、保管費用等によるコストの上昇や販売ルートの限定等の不利な点が生じる。  1,5-AF is a carbohydrate expected to be used in various fields. 1,5-AF has low stability in the state of an aqueous solution, and in the storage of a preparation containing 1,5-AF, the product quality such as a decrease in 1,5-AF content with time or coloring of the preparation itself Changes occur. In order to reduce the change in quality, storage at a lower temperature is required. However, when distribution in the market is taken into consideration, there are disadvantages such as an increase in cost due to storage costs and a limitation of sales routes.

一方、噴霧乾燥は澱粉糖の粉末化においても一般に使用されている方法であるが、噴霧乾燥の可否は澱粉糖の重合度に大きく依存する。すなわち、重合度の大きいマルトデキストリンでは、比較的噴霧乾燥は容易であるが、単糖であるグルコース、二糖であるマルトースは噴霧乾燥が困難であり、強制的に乾燥しても吸湿性が高いため、工業的生産において噴霧乾燥は行われていない。これらの糖の粉末製品としては結晶品が一般的である。1,5−AFもグルコースやマルトースと同様に単独での噴霧乾燥は困難であり、他の粉末化の方法として、高純度の1,5−AF溶液を凍結乾燥法により粉末化した報告がなされているが([非特許文献1]参照)、この方法は製造コストが非常に高く、さらに乾燥品の吸湿性が非常に高いという欠点がある。
特表平9−505988号 特開2001−89377号 特開2001−333712号 特開2001−213891号 特開2002−27945号 仏国特許出願公開第2617502号 J.Apply.Glycosci.,Vol46,No4,439−444(1999)
On the other hand, spray drying is a method generally used in pulverization of starch sugar, but whether spray drying is possible or not depends greatly on the degree of polymerization of starch sugar. In other words, maltodextrin with a high degree of polymerization is relatively easy to spray dry, but glucose, which is a monosaccharide, and maltose, which is a disaccharide, are difficult to spray and are highly hygroscopic even when forced to dry. Therefore, spray drying is not performed in industrial production. Crystalline products are common as powder products of these sugars. As with glucose and maltose, spray drying alone is difficult for 1,5-AF, and as a method for pulverization, it has been reported that a high-purity 1,5-AF solution is pulverized by freeze-drying. However, this method has disadvantages that the production cost is very high and the hygroscopicity of the dried product is very high.
Special table hei 9-505988 JP 2001-89377 A Japanese Patent Laid-Open No. 2001-333712 JP 2001-213891 A JP 2002-27945 French Patent Application Publication No. 2617502 J. et al. Apply. Glycosci. , Vol 46, No 4, 439-444 (1999)

本発明の目的は、容易且つ安価に1,5−AFを粉末化する方法を提供することである。  An object of the present invention is to provide a method for pulverizing 1,5-AF easily and inexpensively.

本発明の他の目的は、粉末化された1,5−AFを提供することである。  Another object of the present invention is to provide powdered 1,5-AF.

本発明のさらに他の目的および利点は、以下の説明から明らかになろう。  Still other objects and advantages of the present invention will become apparent from the following description.

本発明者らは、1,5−AFの粉末化について鋭意研究を重ねた結果、1,5−AFを澱粉分解物と混合して噴霧乾燥することで容易に粉末化できることを見出し、その究明事実に基づき本発明に到達した。  As a result of intensive research on pulverization of 1,5-AF, the present inventors have found that 1,5-AF can be easily pulverized by mixing with a starch degradation product and spray-drying. The present invention has been reached based on the facts.

すなわち、本発明によれば、本発明の上記目的および利点は、第1に、1,5−AF1重量部に対して0.2〜10.0重量部の澱粉分解物等を混合した1,5−AF含有組成物を噴霧乾燥することを特徴とする粉末1,5−AFの製造方法によって達成される。  That is, according to the present invention, the above-mentioned objects and advantages of the present invention are as follows. First, 0.2 to 10.0 parts by weight of a starch decomposition product or the like is mixed with 1 part by weight of 1,5-AF. This is achieved by a method for producing powder 1,5-AF, characterized by spray-drying a 5-AF-containing composition.

また、本発明によれば、本発明の上記目的および利点は、第2に、澱粉あるいは澱粉分解物をα−1,4−グルカンリアーゼで分解することで得られる1,5−AFと分解残物であるマルトデキストリンから成る1,5−AF含有組成物を、そのまま噴霧乾燥することを特徴とする粉末1,5−AFの製造方法によって達成される。  In addition, according to the present invention, the above-mentioned objects and advantages of the present invention are, secondly, 1,5-AF obtained by decomposing starch or starch degradation product with α-1,4-glucan lyase, and the decomposition residue. This is achieved by a method for producing powder 1,5-AF, which comprises spray-drying a 1,5-AF-containing composition comprising maltodextrin as a product.

さらに、本発明によれば、本発明の上記目的および利点は、第3に、上記製造法によって得られた粉末1,5−AFを提供することによって達成される。  Furthermore, according to the present invention, the above objects and advantages of the present invention are achieved thirdly by providing the powder 1,5-AF obtained by the above production method.

これらについて、以下に詳述する。  These are described in detail below.

本発明において、原料となる1,5−AFは以下のような既に公知の方法によって得ることができる。  In the present invention, 1,5-AF used as a raw material can be obtained by the following known methods.

紅藻類Gracilaria verrucosaに水を加え磨砕した後、固液分離して得られた抽出液から澱粉吸着法で調製したα−1,4−グルカンリアーゼ酵素液を、もち米澱粉水溶液に作用させた後、濃度50%となるようにエタノールを加え未反応の澱粉を沈澱除去したのち上澄み液を濃縮して1,5−AF純度95%以上の標品を得た。  After adding water to the red algae Gracilaria verrucosa and grinding it, the α-1,4-glucan lyase enzyme solution prepared by the starch adsorption method from the extract obtained by solid-liquid separation was allowed to act on the glutinous rice starch aqueous solution. Thereafter, ethanol was added to a concentration of 50%, and unreacted starch was precipitated and removed, and then the supernatant was concentrated to obtain a sample having a 1,5-AF purity of 95% or more.

こうして得られた純度95%以上の1,5−AFを粉末化基材と混合せずにそのまま噴霧乾燥を試みると、噴霧乾燥条件をどのように設定しても粉末状にすることは不可能であった。  When spray drying is performed without mixing the thus obtained 1,5-AF having a purity of 95% or more with the powdered base material, it is impossible to form a powder regardless of the spray drying conditions. Met.

本発明の粉末1,5−AFの製造法において、上記方法で調製した1,5−AFと澱粉分解物とを混合して得られた1,5−AF含有組成物を噴霧乾燥することにより、容易に且つ安価に粉末1,5−AFを製造することができる。  In the method for producing powder 1,5-AF of the present invention, by spray-drying a 1,5-AF-containing composition obtained by mixing 1,5-AF prepared by the above method and a starch degradation product The powder 1,5-AF can be produced easily and inexpensively.

澱粉分解物の混合割合は、1,5−AF1重量部に対して0.2〜10.0重量部であることが好ましく、0.5〜3.0重量部であることがより好ましい。  The mixing ratio of the starch decomposition product is preferably 0.2 to 10.0 parts by weight and more preferably 0.5 to 3.0 parts by weight with respect to 1,5-AF 1 part by weight.

また、上述のマルトデキストリン溶液にα−1,4−グルカンリアーゼ酵素液を作用させて得られた反応液つまり、1,5−AFおよび未分解のマルトデキストリンから成る1,5−AF含有組成物をそのまま噴霧乾燥して粉末化することも可能である。  Further, a reaction solution obtained by allowing an α-1,4-glucan lyase enzyme solution to act on the maltodextrin solution described above, that is, a 1,5-AF-containing composition comprising 1,5-AF and undegraded maltodextrin It is also possible to spray and dry the powder as it is.

本発明の粉末化方法において、噴霧乾燥原液である1,5−AF含有組成物の固形分は5〜70重量%であることが好ましく、コストおよび乾燥効率を考慮した場合、30〜60重量%であることがより好ましい。  In the pulverization method of the present invention, the solid content of the 1,5-AF-containing composition that is the spray-drying stock solution is preferably 5 to 70% by weight, and 30 to 60% by weight in consideration of cost and drying efficiency. It is more preferable that

乾燥のために使用される噴霧乾燥機としては、ノズル型あるいは回転円盤型のような一般的に噴霧乾燥に使用される装置を用いることができる。  As the spray dryer used for drying, a device generally used for spray drying, such as a nozzle type or a rotating disk type, can be used.

噴露乾燥機に吹き込む熱風の温度は、乾燥時に1,5−AFが他の化合物に変換あるいは分解することや製品の着色等を考慮した場合、70〜200℃が好ましい。  The temperature of the hot air blown into the spray dryer is preferably from 70 to 200 ° C. in consideration of conversion or decomposition of 1,5-AF into other compounds, product coloring, and the like during drying.

こうして本発明の方法によって得られた1,5−AF粉末品は、白色微粉末で、その水分量が1〜3%程度であった。この粉末を顕微鏡で確認したところ比較的粒径のそろった球状であり、また、流動性、溶解性、分散性ともに優れていた。1,5−AF粉末品はその液状品に比べて保存安定性が非常に高いため、常温あるいはそれ以上の温度下での保存が可能である。  Thus, the 1,5-AF powder product obtained by the method of the present invention was a white fine powder, and its water content was about 1 to 3%. When this powder was confirmed with a microscope, it was spherical with a relatively uniform particle diameter, and was excellent in fluidity, solubility and dispersibility. Since the 1,5-AF powder product has very high storage stability compared to the liquid product, it can be stored at room temperature or higher.

1,5−AF粉末品は、抗菌剤、酸化防止剤、変色防止剤、食味改良剤などとして、食品、飲料、飼料、化粧品、医薬品などの各種組成物にそれぞれの用途に応じて添加することができ、添加量としては特に限定されない。  1,5-AF powder products should be added to various compositions such as foods, beverages, feeds, cosmetics, and pharmaceuticals as antibacterial agents, antioxidants, anti-discoloring agents, and taste improvers, etc. The addition amount is not particularly limited.

本発明によれば、1,5−AFを粉末化基材である澱粉分解物と混合して噴霧乾燥することで、容易に且つ安価に1,5−AFの粉末品を製造することができる。こうして得られた1,5−AF粉末品は、保存安定性が向上し、常温での長期保存も可能である。    According to the present invention, 1,5-AF can be easily and inexpensively manufactured by mixing 1,5-AF with a starch decomposition product as a powdered base material and spray drying. . The 1,5-AF powder product thus obtained has improved storage stability and can be stored at room temperature for a long time.

以下の実施例により本発明をさらに詳述するが、本発明は、これらによって何ら限定されるものではない。なお、以下の実施例中で使用する%は重量%を意味する。また、噴霧乾燥機は大川原化工機(株)製L−8型(回転円盤型)を使用した。  The following examples further illustrate the present invention, but the present invention is not limited thereto. In addition,% used in the following examples means weight%. Moreover, the Okawahara Kako Co., Ltd. product L-8 type (rotary disk type) was used for the spray dryer.

実施例1
1,5−AF溶液を濃度30%とした後、表1に記載の条件で噴霧乾燥を試みた。しかし、微細な液滴状となり、乾燥粉末は得られなかった。さらに、さまざまな濃度条件、乾燥条件での噴霧乾燥を試みたが粉末化は不可能であった。
Example 1
After adjusting the concentration of the 1,5-AF solution to 30%, spray drying was attempted under the conditions described in Table 1. However, it became fine droplets and a dry powder was not obtained. Furthermore, spray drying under various concentration conditions and drying conditions was attempted, but powdering was impossible.

Figure 2005263770
Figure 2005263770

実施例2
濃度30%の1,5−D−アンヒドロフルクトース溶液と濃度30%のマルトデキストリン(DE=16)溶液を1:0.8の比で混合した後、表2に記載の条件で乾燥した。その結果、微細な球状の乾燥粉末を得る事ができた。出来た製品の水分含量は3.11%であった。
Example 2
A 1,5-D-anhydrofructose solution with a concentration of 30% and a maltodextrin (DE = 16) solution with a concentration of 30% were mixed at a ratio of 1: 0.8, and then dried under the conditions described in Table 2. As a result, a fine spherical dry powder could be obtained. The resulting product had a moisture content of 3.11%.

Figure 2005263770
Figure 2005263770

実施例3
濃度30%の1,5−D−アンヒドロフルクトース溶液と濃度30%のマルトデキストリン(DE=16)溶液を1:1.5の比で混合した後、表3に記載の条件で乾燥した。その結果、微細な球状の乾燥粉末を得る事ができた。出来た製品の水分含量は1.80%であった。
Example 3
A 1,5-D-anhydrofructose solution with a concentration of 30% and a maltodextrin (DE = 16) solution with a concentration of 30% were mixed at a ratio of 1: 1.5, and then dried under the conditions described in Table 3. As a result, a fine spherical dry powder could be obtained. The resulting product had a moisture content of 1.80%.

Figure 2005263770
Figure 2005263770

実施例4
DE12のマルトデキストリン水溶液にグルカンリアーゼを作用させて得た糖液(糖組成:ブドウ糖 8%、1,5−AF 36%、未分解マルトデキストリン 56%)を表4に記載の条件で乾燥した。その結果、微細な球状の乾燥粉末を得る事ができた。出来た製品の水分含量は1.72%であった。
Example 4
A sugar solution (sugar composition: glucose 8%, 1,5-AF 36%, undegraded maltodextrin 56%) obtained by allowing glucan lyase to act on a maltodextrin aqueous solution of DE12 was dried under the conditions described in Table 4. As a result, a fine spherical dry powder could be obtained. The resulting product had a moisture content of 1.72%.

Figure 2005263770
Figure 2005263770

Claims (8)

1,5−D−アンヒドロフルクトースと澱粉分解物から成る1,5−D−アンヒドロフルクトース含有組成物を噴霧乾燥することを特徴とする粉末1,5−D−アンヒドロフルクトースの製造法。A process for producing powdered 1,5-D-anhydrofructose comprising spray-drying a 1,5-D-anhydrofructose-containing composition comprising 1,5-D-anhydrofructose and a starch degradation product. 1,5−D−アンヒドロフルクトース含有組成物中に澱粉分解物が1,5−D−アンヒドロフルクトース1重量部に対して0.2〜10.0重量部含有されることを特徴とする請求項1に記載の製造法。The 1,5-D-anhydrofructose-containing composition contains 0.2 to 10.0 parts by weight of a starch degradation product with respect to 1 part by weight of 1,5-D-anhydrofructose. The manufacturing method of Claim 1. 1,5−D−アンヒドロフルクトース含有組成物中に澱粉分解物が1,5−D−アンヒドロフルクトースに対して0.5〜3.0重量部含有されることを特徴とする請求項1に記載の製造法。The starch-decomposed product is contained in the 1,5-D-anhydrofructose-containing composition in an amount of 0.5 to 3.0 parts by weight based on 1,5-D-anhydrofructose. The production method described in 1. 澱粉分解物を構成するグルコース残基の重合度が7以上である請求項1に記載の製造法。The process according to claim 1, wherein the degree of polymerization of glucose residues constituting the starch degradation product is 7 or more. 1,5−D−アンヒドロフルクトース含有組成物が、澱粉あるいは澱粉分解物をα−1,4−グルカンリアーゼで分解することによって得られたものであり、1,5−D−アンヒドロフルクトースとその分解残物であるマルトデキストリンから成るものである、請求項1に記載の製造法。A 1,5-D-anhydrofructose-containing composition was obtained by decomposing starch or starch degradation product with α-1,4-glucan lyase, and 1,5-D-anhydrofructose and The manufacturing method of Claim 1 which consists of maltodextrin which is the decomposition | disassembly residue. 1,5−D−アンヒドロフルクトース含有組成物の固形分が5〜60重量%である、請求項1〜5のいずれかに記載の製造法。The manufacturing method in any one of Claims 1-5 whose solid content of a 1, 5-D-anhydrofructose containing composition is 5 to 60 weight%. 噴霧乾燥における熱風の温度が70〜200℃である、請求項1〜6のいずれかに記載の製造法。The manufacturing method in any one of Claims 1-6 whose temperature of the hot air in spray drying is 70-200 degreeC. 請求項1〜7のいずれかに記載の製造法によって得られる粉末1,5−D−アンヒドロフルクトース。Powder 1,5-D-anhydrofructose obtained by the production method according to claim 1.
JP2004120909A 2004-03-19 2004-03-19 Method for producing powdery 1,5-d-anhydrofructose Pending JP2005263770A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2004120909A JP2005263770A (en) 2004-03-19 2004-03-19 Method for producing powdery 1,5-d-anhydrofructose

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP2004120909A JP2005263770A (en) 2004-03-19 2004-03-19 Method for producing powdery 1,5-d-anhydrofructose

Publications (1)

Publication Number Publication Date
JP2005263770A true JP2005263770A (en) 2005-09-29

Family

ID=35088672

Family Applications (1)

Application Number Title Priority Date Filing Date
JP2004120909A Pending JP2005263770A (en) 2004-03-19 2004-03-19 Method for producing powdery 1,5-d-anhydrofructose

Country Status (1)

Country Link
JP (1) JP2005263770A (en)

Similar Documents

Publication Publication Date Title
JP4479932B2 (en) Method for producing S-adenosyl-L-methionine-containing dry yeast having excellent storage stability, the product and the molded composition
WO2011027790A1 (en) Powder containing anhydrous crystals of 2-o-α-d-glucosyl-l-ascorbic acid, manufacturing method therefor, and use thereof
EP0497439A1 (en) Erythritol compositions
WO2002057011A1 (en) Dehydrating agent and method for dehydrating moist article using the agent and dehydrated article obtained by the method
US20090312281A1 (en) Process for the preparation of a pulverulent composition and product as obtained
CN100413975C (en) Method of preparing alpha-glycosylisoquercitrin, intermediate therefor and by-product
JP5901125B2 (en) Collagen peptide-containing powder composition and method for producing the same
WO2018174207A1 (en) Method for producing preparation containing thickening polysaccharide
CN101163410B (en) Process for drying uronic acid oligosaccharides
KR20180101497A (en) α, α-trehalose dihydrate crystal-containing powder, production method and use thereof
JP6088872B2 (en) Sophorolipid powder with suppressed decomposition of lactone type sophorolipid
JP2005263770A (en) Method for producing powdery 1,5-d-anhydrofructose
JPH10276757A (en) Alcohol-containing granular material
JP5524689B2 (en) Starch for seasoning, method for producing the same, and use thereof
WO2003044143A1 (en) Method of sustaining aroma and use thereof
WO2017047804A1 (en) Production method for polysaccharide thickener-containing preparation
FR2899495A1 (en) Producing a powder composition comprises spray drying an aqueous solution of a hygroscopic material, especially lactulose, together with a powdered agglomeration inhibitor
JP4620913B2 (en) Dama formation inhibitor and its use
WO2003018597A1 (en) POWDER COMPRISING WATER-CONTAINING β-MALTOSE CRYSTALS AND PRODUCTION PROCESS AND USE THEREOF
JP3148935B2 (en) New powdered vinegar
RU2369618C1 (en) Oligochitosan complex salt and method of obtaining said salt
WO2015152145A1 (en) Process for producing crystalline 2-o-α-d-glucosyl-l-ascorbic acid powder
JP2006298763A (en) Method for producing nigerose-containing syrup crystal and crystal nigerose
JPH0430773A (en) Oligosaccharide-containing powder and its production
JP3005809B2 (en) Malt triose-rich composition