JP2981582B2 - Manufacturing method of organic acid-sugar complex - Google Patents
Manufacturing method of organic acid-sugar complexInfo
- Publication number
- JP2981582B2 JP2981582B2 JP4073139A JP7313992A JP2981582B2 JP 2981582 B2 JP2981582 B2 JP 2981582B2 JP 4073139 A JP4073139 A JP 4073139A JP 7313992 A JP7313992 A JP 7313992A JP 2981582 B2 JP2981582 B2 JP 2981582B2
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- Prior art keywords
- complex
- organic acid
- sugar
- acid
- manufacturing
- 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.)
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- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Description
【０００１】[0001]
【産業上の利用分野】本発明は有機酸と糖を混合し、加
熱することを特徴とする有機酸・糖複合体の製造法に関
し、詳しくは、有機酸としてクエン酸、マロン酸、リン
ゴ酸、マレイン酸、糖としてグルコース、マンノース、
ガラクトース、ソルビトール、マンニトール、キシリト
ールを用い、５０〜１５０℃で加熱処理して反応させ有
機酸・糖複合体を生産し、さらに、反応後中和し、酵母
を作用させ未反応糖を資化し、除去して有機酸・糖複合
体含有量を増加させる方法に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a method for producing an organic acid-sugar complex comprising mixing an organic acid and a saccharide and heating the mixture. More specifically, citric acid, malonic acid and malic acid are used as the organic acid. , Maleic acid, glucose and mannose as sugars,
Using galactose, sorbitol, mannitol, and xylitol, heat-treat at 50 to 150 ° C. to produce an organic acid-sugar complex, further neutralize after the reaction, allow yeast to act, and utilize unreacted sugar, The present invention relates to a method for increasing the content of an organic acid-sugar complex by removing it.
【０００２】[0002]
【従来の技術】従来、脂肪酸と糖のエステルについては
いくつかの特許、報告があり、例えば、リパーゼを用い
た脂肪酸と糖の縮合、酸縮合、有機酸塩化物を用いたエ
ステル化反応については知られている。2. Description of the Related Art Conventionally, there have been several patents and reports on esters of fatty acids and sugars. For example, about the condensation of fatty acids and sugars using lipase, acid condensation, and esterification reactions using organic acid chlorides. Are known.
【０００３】[0003]
【発明が解決しようとする課題】しかし、本発明のよう
な複合体の生産方法は殆ど知られていず、ましてや該物
質の種類、性質については全く知られていなかった。However, a method for producing a complex as in the present invention is hardly known, and much less is known about the type and properties of the substance.
【０００４】最近、糖複合体の機能性についての研究の
進展がめざましく、各種糖複合体素材への要求が著しく
高まってきている。特に、機能性食品素材への要求度は
高く、多くの機能性糖質が開発されている。[0004] In recent years, research on the functionality of glycoconjugates has been remarkably advanced, and the demand for various types of glycoconjugate materials has been remarkably increased. In particular, there is a high demand for functional food materials, and many functional carbohydrates have been developed.
【０００５】[0005]
【課題を解決するための手段】本発明者らは各種有機酸
と糖を混合し、加熱して５０℃以上にすることにより各
種有機酸・糖複合体が形成され、水分を連続的に除去す
ることにより収率が増大し、さらに、未反応糖を微生物
により資化して、含有率を高めることを見い出して本発
明を完成したのである。Means for Solving the Problems The present inventors mix various organic acids and saccharides and heat them to 50 ° C. or higher to form various organic acid-sugar complexes and continuously remove water. Thus, the present invention was found to increase the yield, and to further increase the content by assimilating the unreacted sugar by microorganisms, thereby completing the present invention.
【０００６】すなわち、本発明は有機酸と糖を混合し、
加熱することを特徴とする有機酸・糖複合体の製造法に
関し、詳しくは、温度が５０℃〜１５０℃であり、有機
酸としてクエン酸、マロン酸、リンゴ酸、マレイン酸、
糖としてグルコース、マンノース、ガラクトース、ソル
ビトール、マンニトール、キシリトールを用い、必要な
らば減圧濃縮しながら反応し、加熱処理後中和し、酵母
を作用させ未反応糖を資化して除去することを特徴とす
るものである。That is, the present invention comprises mixing an organic acid and a sugar,
Regarding the method for producing an organic acid-sugar complex characterized by heating, specifically, the temperature is 50 ° C. to 150 ° C., and citric acid, malonic acid, malic acid, maleic acid,
Glucose, mannose, galactose, sorbitol, mannitol, xylitol are used as the saccharides. Is what you do.
【０００７】糖部分としては、この他、各種の単糖、例
えば４炭糖のエリスロース、５炭糖のアラビノース、リ
ボース、６炭糖のソルボースなど、糖アルコール、グリ
セリンなどのポリオールが利用できる。[0007] In addition to the sugar moiety, various monosaccharides, for example, polyols such as sugar alcohols, glycerin, etc., such as erythrose of 4 carbon sugars, arabinose, ribose of 5 carbon sugars, and sorbose of 6 carbon sugars can be used.
【０００８】澱粉などの酸分解を受け易い多糖への本発
明の方法の適用は困難である。また、ラクトース、マル
トースなどのニ糖類、大豆オリゴ糖、乳オリゴ糖、セロ
オリゴ糖、ヘミセルオリゴ糖、サイクロデキストリンも
酸分解が起こり、収率は著しく低い。したがって、少量
形成で目的を達成できるものであれば本発明の方法を適
用できるが、実用化のためには分解を抑制しながら形成
反応を進める方法との組合せが必要である。[0008] It is difficult to apply the method of the present invention to polysaccharides susceptible to acid degradation such as starch. In addition, disaccharides such as lactose and maltose, soybean oligosaccharides, milk oligosaccharides, cellooligosaccharides, hemicell oligosaccharides, and cyclodextrins are also subjected to acid decomposition, and the yield is extremely low. Therefore, the method of the present invention can be applied as long as the object can be achieved with a small amount of formation, but for practical use, a combination with a method of promoting the formation reaction while suppressing decomposition is required.
【０００９】具体的に、表１の組成で１００℃で２時間
攪拌反応した結果、複合体が著量形成される糖としては
表２のように、グルコース、マンノース、ガラクトー
ス、ソルビトールであった。フラクトースはこの条件で
は分解して褐変するが、５０〜７０℃の反応では２〜３
％程度の複合体が形成され、キシロースでは本反応条件
で分解は起こるものの複合体も形成される。Specifically, as shown in Table 2, glucose, mannose, galactose and sorbitol, as shown in Table 2, as a result of a stirring reaction at 100 ° C. for 2 hours with the composition shown in Table 1. Fructose decomposes and browns under these conditions, but in a reaction at 50-70 ° C, 2-3
% Of the complex is formed. With xylose, decomposition occurs under the present reaction conditions, but a complex is also formed.
【００１０】[0010]
【表１】 [Table 1]
【００１１】[0011]
【表２】 [Table 2]
【００１２】温度は何度でもよいが、特に高温で、キシ
ロース、フラクトースなどの分解し易い糖の場合は、糖
が分解しないように真空、不活性ガス中で行うことが望
ましい。反応時間は特に限定されないが１時間以上が望
ましく、２時間以上でも大体１時間と同程度の形成率に
なる。形成率上昇のためには、減圧濃縮しながら反応し
て、水分を飛ばしながら反応をするか、蒸発乾固するな
ど、水分を除去する方法であればいずれでも効果があ
る。油性溶媒中での反応なども考えられる。The temperature may be any number of times, but particularly in the case of high-temperature, easily decomposable sugars such as xylose and fructose, it is desirable to carry out the reaction in a vacuum and in an inert gas so that the sugars are not decomposed. The reaction time is not particularly limited, but is preferably 1 hour or more, and the formation rate is about the same as 1 hour even if it is 2 hours or more. In order to increase the formation rate, any method can be used as long as the method removes moisture, such as reacting while concentrating under reduced pressure and reacting while skipping moisture, or evaporating to dryness. A reaction in an oily solvent is also considered.
【００１３】有機酸部分としてはＣＯＯＨ基をもつもの
であれば、大抵のものが適用できるが、酸によって、例
えば、表３のように糖同志で縮合反応が起こり複合体を
形成しないものもある。As the organic acid moiety, most can be used as long as it has a COOH group. However, for example, as shown in Table 3, some of the acids cause a condensation reaction between sugars and do not form a complex, as shown in Table 3. .
【００１４】[0014]
【表３】 [Table 3]
【００１５】複合体の分析は薄層クロマトグラフィーで
行い、展開溶媒としてブタノール：エタノール：酢酸：
水＝２：２：１：１、発色剤としてはアニスアルデヒド
ー硫酸（９５％エタノール９ｍｌ，濃硫酸０.５ｍｌ，
アニスアルデヒド０.５ｍｌ）を用いた。The analysis of the complex was carried out by thin layer chromatography, and butanol: ethanol: acetic acid:
Water = 2: 2: 1: 1, and as a coloring agent anisaldehyde-sulfuric acid (95% ethanol 9 ml, concentrated sulfuric acid 0.5 ml,
(Anisaldehyde 0.5 ml) was used.
【００１６】メルク社製、キーゼルグール５７１５の薄
層を用い、展開は室温１回、薄層をホットプレート上で
乾燥した後、発色試薬を吹きかけ１５０℃、１〜２分で
発色した。色調は、糖：藍色（ソルビトールはピンク
系）、クエン酸は紺色が強いが一般に紫−ピンク系、Rf
は大きい方から糖、糖重合物、複合体、酸の順序である。A thin layer of Kieselgur 5715, manufactured by Merck, was used. The development was performed once at room temperature, the thin layer was dried on a hot plate, and then a color-forming reagent was sprayed to develop the color at 150 ° C for 1 to 2 minutes. The color is sugar: indigo (sorbitol is pink), citric acid is dark blue, but generally purple-pink, Rf
Is the order of sugar, sugar polymer, complex, and acid from the largest.
【００１７】分離はセファデックスＧ-１５で荒分けし
た後、バイオゲルＰ-２で分離精製した。ＯＤＳカラム
でも分離可能であるが、糖−複合体−有機酸の間に重な
る部分が多い。The separation was carried out roughly by Sephadex G-15, followed by separation and purification by Biogel P-2. Although separation is possible with an ODS column, there are many overlapping portions between the sugar, the complex and the organic acid.
【００１８】分離した複合体は１規定苛性ソーダで加水
分解したところ、等モルの糖と有機酸からなり、結合位
置はＮＭＲ分析の結果から、表４のように有機酸は主と
して糖の６位（６炭糖アルコールでは６位と１位、５炭
糖アルコールでは５位と１位）に結合していた。The separated complex was hydrolyzed with 1N caustic soda, and was composed of equimolar sugar and organic acid. The bonding position was determined by NMR analysis. In the case of hexacarbon alcohol, it was bonded to the 6th and 1st positions, and in the case of 5 sugar alcohol, it was bonded to the 5th and 1st positions.
【００１９】[0019]
【表４】 [Table 4]
【００２０】クエン酸・グルコース複合体は分子量が３
５４.３で、推定構造式は以下のようである。The citric acid / glucose complex has a molecular weight of 3
At 54.3, the estimated structural formula is as follows:
【００２１】[0021]
【化１】 Embedded image
【００２２】クエン酸・ソルビトール複合体は分子量３
５６.３で、推定構造式は以下のようである。The citrate-sorbitol complex has a molecular weight of 3
At 56.3, the estimated structural formula is as follows:
【００２３】[0023]
【化２】 Embedded image
【００２４】有機酸あるいは糖を一種類以上混合して反
応させてもよく、反応終了後の着色度はグルコース、マ
ンノースなどでは１時間で極薄い黄色、２時間でレモン
イエローになる程度であり、ソルビトール等の糖アルコ
ールでは全く無色である。したがって、このままでも食
品素材として利用できる。One or more organic acids or sugars may be mixed and reacted, and the degree of coloration after the reaction is such that glucose or mannose becomes very pale yellow in one hour and lemon yellow in two hours. It is completely colorless with sugar alcohols such as sorbitol. Therefore, it can be used as a food material as it is.
【００２５】さらに、酵母は複合体を資化できないの
で、必要ならば、これらのオリゴ糖を酵母によって資化
し、複合体含有量を高め、複合体のみを得ることもでき
る。また、酵母によっては資化できない単糖もあるの
で、用いる単糖によって酵母を選択すべきである。Furthermore, since yeast cannot assimilate the complex, if necessary, these oligosaccharides can be assimilated by yeast to increase the content of the complex and obtain only the complex. In addition, since some yeasts cannot be assimilated, yeasts should be selected according to the monosaccharides used.
【００２６】[0026]
【実施例】次に、本発明を実施例により説明する。Next, the present invention will be described with reference to examples.
【００２７】実施例１ グルコース１ｇ、クエン酸１.１７ｇ、水１００μｌを混
合し、１００℃で１時間攪拌反応した結果、クエン酸・グ
ルコース複合体が２０.４％の収率で得られた。Example 1 1 g of glucose, 1.17 g of citric acid and 100 μl of water were mixed, and the mixture was stirred and reacted at 100 ° C. for 1 hour. As a result, a citric acid / glucose complex was obtained at a yield of 20.4%.
【００２８】さらに、１時間減圧濃縮しながら反応した
結果、収率は５１.６％に増大した。Further, the reaction was carried out while concentrating under reduced pressure for 1 hour. As a result, the yield increased to 51.6%.
【００２９】実施例２ グルコースをマンノースに、クエン酸をマロン酸に変え
た以外は実施例１と同様にして、収率８.６％を得た。Example 2 A yield of 8.6% was obtained in the same manner as in Example 1, except that glucose was changed to mannose and citric acid was changed to malonic acid.
【００３０】実施例３ グルコースをソルビトールに、クエン酸をマレイン酸に
変えた以外は実施例１と同様にして、収率２１.８％を
得た。Example 3 A yield of 21.8% was obtained in the same manner as in Example 1 except that glucose was changed to sorbitol and citric acid was changed to maleic acid.
【００３１】実施例４ 実施例１の減圧濃縮物を中和し、市販パン酵母０.１
ｇ、炭酸カルシウム０.０１ｇを加え、３５℃で４８時
間処理して、グルコースを除去することができた。本処
理液には未反応の有機酸が含まれるが、カラムクロマト
グラフィーによる分離は容易であった。Example 4 The vacuum concentrate of Example 1 was neutralized and commercial baker's yeast 0.1 was prepared.
g and 0.01 g of calcium carbonate were added thereto, and the mixture was treated at 35 ° C. for 48 hours to remove glucose. Although this treatment liquid contains an unreacted organic acid, separation by column chromatography was easy.
【００３２】[0032]
【発明の効果】本発明の方法では主として有機酸が糖の
１級水酸基に結合した複合体ができるので、いずれかを
必要な場合は分離法を開発するか、いずれか一方を切断
する酵素の探索を必要とする。しかし、食品用として用
いる場合は特に分離を必要とせず混合物のままでも利用
できる。また、未反応糖、有機酸が複合体と混合した状
態でも食品素材として利用できる。According to the method of the present invention, a complex in which an organic acid is mainly bonded to the primary hydroxyl group of a sugar is formed. Therefore, if either of them is required, a separation method must be developed or an enzyme that cleaves one of them can be used. Requires a search. However, when it is used for foods, it can be used as a mixture without any need for separation. In addition, even when unreacted sugars and organic acids are mixed with the complex, they can be used as food materials.
【００３３】本食品素材は甘味と酸味を兼ね備えたもの
であり、フラクトースなどとの混合によりスッキリした
食味を与えることから、清涼飲料用に適している。This food material has both sweetness and sourness and gives a refreshing taste by mixing with fructose and the like, and is therefore suitable for soft drinks.
【００３４】また、遊離のＣＯＯＨ基があるためにカル
シウム、鉄などの金属イオンの補給キャリアーとして利
用できる。Further, since it has a free COOH group, it can be used as a supply carrier for metal ions such as calcium and iron.
【００３５】本発明の複合体は微生物に資化され難いこ
とから、一般の難消化性食品素材と同様にローカロリー
でダイエット食品に利用でき、さらに、コレステロール
蓄積防止、虫歯防止、ビフィズス菌増殖作用もあるもの
と考えられる。医薬の面でも、糖尿病患者用、血圧降下
作用、抗腫瘍その他、広い用途が期待される。Since the complex of the present invention is hardly assimilated by microorganisms, it can be used in diet foods with low calories, as in general indigestible food materials. It is thought that there is also. In terms of medicine, it is expected to be widely used for diabetics, blood pressure lowering, antitumor, etc.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.6 識別記号 ＦＩ Ｃ０７Ｃ 69/60 Ｃ０７Ｃ 69/60 69/675 69/675 69/704 69/704 Ｃ１２Ｐ 1/02 Ｃ１２Ｐ 1/02 Ｚ // Ａ２３Ｌ 1/307 Ａ２３Ｌ 1/307 Ａ６１Ｋ 31/00 ６０１ Ａ６１Ｋ 31/00 ６０１Ｂ ６０１Ｇ ６０３ ６０３Ｌ ６０３Ｎ ６０９ ６０９Ｊ ６３５ ６３５ 31/215 31/215 31/70 ６０６ 31/70 ６０６ (Ｃ１２Ｐ 1/02 Ｃ１２Ｒ 1:85） (56)参考文献 特開 昭52−12936（ＪＰ，Ａ) Ｃｈｅｍ．Ｍｉｋｒｏｂｉｏｌ．Ｔｅ ｃｈｎｏｌ．Ｌｅｂｅｎｓｍ．，Ｖｏ ｌ．６，（1980），ｐ．129−130 Ｃｈｅｍ．Ｍｉｋｒｏｂｉｏｌ．Ｔｅ ｃｈｎｏｌ．Ｌｅｂｅｎｓｍ．，Ｖｏ ｌ．２，（1973），ｐ．79−82 Ｓｕｅｓｓｗａｒｅｎ，Ｖｏｌ．18, （1973），ｐ．925−928 (58)調査した分野(Int.Cl.6，ＤＢ名) C07H 13/04 C07C 31/18 C07C 31/26 C07C 67/08 C07C 69/38 C07C 69/60 C07C 69/675 C07C 69/704 C12P 1/02 A23L 1/307 A61K 31/215 A61K 31/70 ＣＡ（ＳＴＮ) ＲＥＩＧＳＴＲＹ（ＳＴＮ)──────────────────────────────────────────────────の Continued on the front page (51) Int.Cl. 6 Identification code FI C07C 69/60 C07C 69/60 69/675 69/675 69/704 69/704 C12P 1/02 C12P 1/02 Z // A23L 1/307 A23L 1/307 A61K 31/00 601 A61K 31/00 601B 601G 603 603L 603N 609 609J 635 635 635 31/215 31/215 31/70 606 31/70 606 (C12P 1/02 C12R 1:85) ( 56) References JP-A-52-12936 (JP, A) Chem. Mikrobiol. Technol. Lebensm. , Vol. 6, (1980), p. 129-130 Chem. Mikrobiol. Technol. Lebensm. , Vol. 2, (1973), p. 79-82 Suswaren, Vol. 18, (1973), p. 925-928 (58) Field surveyed (Int.Cl. 6 , DB name) C07H 13/04 C07C 31/18 C07C 31/26 C07C 67/08 C07C 69/38 C07C 69/60 C07C 69/675 C07C 69 / 704 C12P 1/02 A23L 1/307 A61K 31/215 A61K 31/70 CA (STN) REIGSTRY (STN)
Claims (2)
濃縮しながら、混合し、５０℃〜１１０℃で加熱するこ
とを特徴とする有機酸・糖複合体の製造法。1. A method for producing an organic acid-sugar complex, comprising mixing maleic acid and sorbitol while concentrating under reduced pressure, and heating at 50 ° C. to 110 ° C.
縮しながら、混合し、５０℃〜１１０℃で加熱すること
を特徴とする有機酸・糖複合体の製造法。2. A method for producing an organic acid / sugar complex, comprising mixing maleic acid and mannose while concentrating under reduced pressure, and heating at 50 ° C. to 110 ° C.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4073139A JP2981582B2 (en) | 1992-02-26 | 1992-02-26 | Manufacturing method of organic acid-sugar complex |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4073139A JP2981582B2 (en) | 1992-02-26 | 1992-02-26 | Manufacturing method of organic acid-sugar complex |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH06133736A JPH06133736A (en) | 1994-05-17 |
| JP2981582B2 true JP2981582B2 (en) | 1999-11-22 |
Family
ID=13509577
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4073139A Expired - Fee Related JP2981582B2 (en) | 1992-02-26 | 1992-02-26 | Manufacturing method of organic acid-sugar complex |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2981582B2 (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2723013B1 (en) * | 1994-08-01 | 1996-09-20 | Vesuvius France Sa | SIDE SIDE FOR A CONTINUOUS THIN SHEET CASTING MACHINE |
| CA2193243C (en) * | 1994-06-30 | 2005-08-16 | Frederic Caillaud | Side wall for a continuous sheet metal casting machine |
| JP4942141B2 (en) * | 2004-12-02 | 2012-05-30 | 江崎グリコ株式会社 | Glucose transfer method to carboxyl group |
-
1992
- 1992-02-26 JP JP4073139A patent/JP2981582B2/en not_active Expired - Fee Related
Non-Patent Citations (3)
| Title |
|---|
| Ｃｈｅｍ．Ｍｉｋｒｏｂｉｏｌ．Ｔｅｃｈｎｏｌ．Ｌｅｂｅｎｓｍ．，Ｖｏｌ．２，（１９７３），ｐ．７９−８２ |
| Ｃｈｅｍ．Ｍｉｋｒｏｂｉｏｌ．Ｔｅｃｈｎｏｌ．Ｌｅｂｅｎｓｍ．，Ｖｏｌ．６，（１９８０），ｐ．１２９−１３０ |
| Ｓｕｅｓｓｗａｒｅｎ，Ｖｏｌ．１８，（１９７３），ｐ．９２５−９２８ |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH06133736A (en) | 1994-05-17 |
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