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JPH0212546B2 - - Google Patents
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JPH0212546B2 - - Google Patents

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Publication number
JPH0212546B2
JPH0212546B2 JP57037547A JP3754782A JPH0212546B2 JP H0212546 B2 JPH0212546 B2 JP H0212546B2 JP 57037547 A JP57037547 A JP 57037547A JP 3754782 A JP3754782 A JP 3754782A JP H0212546 B2 JPH0212546 B2 JP H0212546B2
Authority
JP
Japan
Prior art keywords
sugar
crystals
dipeptide sweetener
dipeptide
sucrose
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.)
Expired - Lifetime
Application number
JP57037547A
Other languages
Japanese (ja)
Other versions
JPS58155054A (en
Inventor
Koroku Tachibana
Katsumi Sugyama
Toshio Kawasaki
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.)
Ajinomoto Co Inc
Original Assignee
Ajinomoto Co Inc
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 Ajinomoto Co Inc filed Critical Ajinomoto Co Inc
Priority to JP57037547A priority Critical patent/JPS58155054A/en
Publication of JPS58155054A publication Critical patent/JPS58155054A/en
Publication of JPH0212546B2 publication Critical patent/JPH0212546B2/ja
Granted legal-status Critical Current

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Description

【発明の詳細な説明】 本発明は、ジペプチド甘味料を内部に含有し、
甘味の強化された糖結晶及びその製造法に関し、
その目的とするところは、呈味、外観及び物性の
良好な低カロリー甘味料を効率よく提供すること
にある。
DETAILED DESCRIPTION OF THE INVENTION The present invention contains a dipeptide sweetener inside,
Regarding sugar crystals with enhanced sweetness and their manufacturing method,
The purpose is to efficiently provide a low-calorie sweetener with good taste, appearance, and physical properties.

α−L−アスパルチル−L−フエニルアラニン
メチルエステル(以下APと略記する)に代表さ
れるジペプチド甘味料は、スツキリした良質の甘
味を有する低カロリー甘味料であるが、これを卓
上等で使用する場合には水に対する低分散性、溶
解性、更には砂糖の約200倍という高甘味度によ
り、原末のままでの使用に種々の制約を伴う。
Dipeptide sweeteners, represented by α-L-aspartyl-L-phenylalanine methyl ester (hereinafter abbreviated as AP), are low-calorie sweeteners that have a refreshing and high-quality sweetness, and are used for tabletop purposes. In this case, there are various restrictions on its use as a bulk powder due to its low dispersibility and solubility in water and its high sweetness, which is about 200 times that of sugar.

このようなジペプチド甘味料を卓上用等で利用
する場合における制約を解消するための方法とし
て、賦形剤、滑沢剤等と共に錠剤化する方法、ジ
ペプチド甘味料を一旦デキストリン等の食用バル
ク剤と共に水に溶解させ、又はスラリー化して、
主としてスプレードライにより加熱乾燥する方法
などが挙げられる。
In order to overcome the limitations when using dipeptide sweeteners for tabletop use, there are two methods: to form tablets together with excipients, lubricants, etc., and to form dipeptide sweeteners into tablets together with edible bulking agents such as dextrin. Dissolved in water or slurried,
Mainly methods include heating drying by spray drying.

これらの方法は、ジペプチド甘味料の実用化に
寄与する方法ではあるが、例えば、錠剤の場合に
は、甘味度を各自の好みに合せて調節する上で不
便であり、医薬的イメージに繋り易い傾向にあ
り、又、食用バルク剤と共に溶解乃至はスラリー
化した後乾燥する等の方法にあつては、溶解乃至
はスラリー化操作の困難や、乾燥工程における熱
による甘味のロス、更には、比較的多量の水を蒸
発することに伴うエネルギー消費等のデメリツト
を負わざるを得ない。
Although these methods contribute to the practical application of dipeptide sweeteners, for example, in the case of tablets, it is inconvenient to adjust the sweetness level to suit each individual's preference, and they do not give off a medicinal image. In addition, methods such as dissolving or slurrying together with edible bulking agents and then drying may cause difficulties in dissolving or slurrying, loss of sweetness due to heat in the drying process, and However, there are disadvantages such as energy consumption associated with evaporating a relatively large amount of water.

本発明者らは先に、製造工程において甘味のロ
スを生ぜず、エネルギーコスト的に有利で、溶解
性、分散性等の物性も改善されたジペプチド甘味
料顆粒の製造法(特願昭56−34397)を開発した
が、このような顆粒とは別に、結晶感に富むジペ
プチド甘味料の取得につき更に検討し、ジペプチ
ド甘味料及び糖から成る結晶を得ることを目的と
して鋭意検討を重ねた。
The present inventors have previously developed a method for producing dipeptide sweetener granules that does not cause loss of sweetness during the production process, is advantageous in terms of energy costs, and has improved physical properties such as solubility and dispersibility. 34397), but apart from such granules, we further investigated the possibility of obtaining a dipeptide sweetener with a rich crystalline feel, and conducted extensive research with the aim of obtaining crystals consisting of a dipeptide sweetener and sugar.

このような結晶を得る方法としては、先ず、ジ
ペプチド甘味料と糖との共晶乃至は混晶の生成が
挙げられるが、シヨ糖、乳糖、果糖、ブドウ糖等
とジペプチド甘味料との共晶乃至は混晶の生成は
ほとんどみられない。
The first method for obtaining such crystals is to form a eutectic or mixed crystal between a dipeptide sweetener and sugar; Almost no mixed crystal formation is observed.

即ち、本発明者らが確認したところによると、
通常の冷却晶析の場合、シヨ糖とジペプチド甘味
料の組合せあるいは果糖とジペプチド甘味料の組
合せ、乳糖とジペプチド甘味料の組合せでは各別
に晶析し、ブドウ糖とジペプチド甘味料の組合せ
では、ブドウ糖の晶析が困難で、いずれの場合に
おいても、ジペプチド甘味料との共晶乃至は混晶
の形成は非常に難しいことが判明した。
That is, as confirmed by the present inventors,
In the case of normal cooling crystallization, the combinations of sucrose and dipeptide sweeteners, the combinations of fructose and dipeptide sweeteners, and the combinations of lactose and dipeptide sweeteners are crystallized separately, and the combinations of glucose and dipeptide sweeteners are crystallized separately. It has been found that crystallization is difficult and in any case it is very difficult to form a eutectic or mixed crystal with the dipeptide sweetener.

本発明者らは、結晶感に富むジペプチド甘味料
の取得につき更に鋭意検討を加え、以下に述べる
構造を付与することにより、結晶感のある外観を
呈すると共に、呈味、物性、製造効率においても
優れたジペプチド甘味料含有糖結晶が得られると
の知見に至り、本発明を完成した。
The inventors of the present invention have further conducted extensive research into obtaining a dipeptide sweetener with a rich crystalline feel, and by imparting the structure described below, the present inventors have achieved a crystalline appearance as well as improved taste, physical properties, and manufacturing efficiency. The present invention was completed based on the finding that excellent dipeptide sweetener-containing sugar crystals can be obtained.

すなわち、本発明は、ジペプチド甘味料及び糖
を混合、造粒して成る種晶の周囲に糖が晶析して
成ることを特徴とするジペプチド甘味料含有糖結
晶及びその製造法である。
That is, the present invention is a dipeptide sweetener-containing sugar crystal and a method for producing the same, characterized in that sugar is crystallized around seed crystals formed by mixing and granulating a dipeptide sweetener and sugar.

以下、本発明を具体的に説明する。 The present invention will be explained in detail below.

本発明においては種晶又は粗種晶として、ジペ
プチド甘味料と糖を混合造粒したものを用いる。
使用するジペプチド甘味料はα−L−アスパルテ
ル−L−フエニルアラニン、低級アルキルエステ
ル、好ましくはAPであり、糖は、シヨ糖、乳糖、
果糖、ブドウ糖等である。造粒方法は、粉体原料
の造粒法であればどのような方法でもよい。具体
的には、例えば、ジペプチド甘味料と糖を微粉砕
混合し、結合剤と共に流動造粒、押出し造粒、撹
拌造粒、圧縮造粒等の方式で造粒して解砕する。
結合剤としては、水、アルコール、糖その他水溶
性のものの使用が好ましい。解砕品の粒径は約50
〜1000μ、好ましくは100〜500μである。
In the present invention, a granulated mixture of a dipeptide sweetener and sugar is used as the seed crystal or coarse seed crystal.
The dipeptide sweetener used is α-L-aspartel-L-phenylalanine, a lower alkyl ester, preferably AP, and the sugar is sucrose, lactose,
These include fructose and glucose. The granulation method may be any method as long as it is a granulation method for powder raw materials. Specifically, for example, a dipeptide sweetener and sugar are finely ground and mixed, and then granulated and crushed together with a binder by a method such as fluid granulation, extrusion granulation, stirring granulation, or compression granulation.
As the binder, it is preferable to use water, alcohol, sugar and other water-soluble substances. The particle size of the crushed product is approximately 50
~1000μ, preferably 100-500μ.

混合造粒品における糖とジペプチド甘味料の比
率は、目的とする甘味度に応じて調整する。
The ratio of sugar and dipeptide sweetener in the mixed granulated product is adjusted depending on the desired degree of sweetness.

本発明のジペプチド甘味料含有糖結晶は、上記
ジペプチド甘味料と糖の混合造粒品の周囲に糖を
晶析させたものであるが、具体的には、次の方法
により、結晶化する。
The dipeptide sweetener-containing sugar crystals of the present invention are obtained by crystallizing sugar around the granulated mixture of the dipeptide sweetener and sugar. Specifically, the sugar crystals containing the dipeptide sweetener are crystallized by the following method.

すなわち、上記混合造粒品を種晶(又は粗種
晶)として、ジペプチド甘味料及び糖の飽和液中
で糖の結晶を成長させる。
That is, sugar crystals are grown in a saturated solution of the dipeptide sweetener and sugar using the mixed granulated product as a seed crystal (or crude seed crystal).

この飽和液に使用する溶媒は特に限定されない
が、水又は親水性有機溶媒例えばメタノール、エ
タノール等と水との混合溶液が使用できる。具体
的には、一例として糖にジペプチド甘味料−糖の
飽和液を加温して接触させ、次いで、この液を冷
却して糖を過飽和とした状態で、上記混合造粒し
た種晶に接触させて糖を晶析し、種晶を糖結晶で
コーテイングする方法が挙げられる。ジペプチド
甘味料が飽和で、糖が過飽和の状態で種晶と接触
させるため、種晶成分が溶媒中に溶解することな
く、ジペプチド甘味料含有糖結晶を得ることがで
きる。
The solvent used for this saturated liquid is not particularly limited, but water or a mixed solution of water and a hydrophilic organic solvent such as methanol or ethanol can be used. Specifically, as an example, a saturated dipeptide sweetener-sugar solution is heated and brought into contact with sugar, and then this solution is cooled to become supersaturated with sugar and brought into contact with the mixed and granulated seed crystals. An example of this method is to crystallize the sugar by allowing the seed crystals to coat the seed crystals with the sugar crystals. Since the dipeptide sweetener is brought into contact with the seed crystal in a saturated state and the sugar is supersaturated, the dipeptide sweetener-containing sugar crystal can be obtained without dissolving the seed crystal component in the solvent.

種晶とその周囲に形成した糖結晶との比率は、
目的とするジペプチド甘味料含有糖結晶の甘味
度、結晶感の強さに応じて任意に変えることが出
来る。一方、このジペプチド甘味料−糖の飽和液
中で、ジペプチド甘味料と糖の混合造粒品を粗種
晶として糖を周囲にコーテイングする程度に晶析
したものを種晶として、糖溶液中で、濃縮晶析等
により更に晶析し糖の結晶を成長させることによ
り、効率よく、結晶感に富むジペプチド甘味料含
有糖結晶を製造することができる。この場合、混
合造粒した粗種晶の周囲をコーテイングした糖結
晶の比率は種晶の約1〜20%程度でよく、5〜10
%程度が好ましい。
The ratio between the seed crystal and the sugar crystals formed around it is
It can be arbitrarily changed depending on the degree of sweetness of the desired dipeptide sweetener-containing sugar crystals and the strength of the crystalline feeling. On the other hand, in this dipeptide sweetener-sugar saturated solution, a mixed granulated product of the dipeptide sweetener and sugar is used as coarse seed crystals, and the sugar is crystallized to the extent that the surrounding area is coated. By further crystallizing and growing sugar crystals by concentration crystallization or the like, it is possible to efficiently produce dipeptide sweetener-containing sugar crystals with a rich crystalline feel. In this case, the ratio of sugar crystals coated around the coarse seed crystals mixed and granulated may be about 1 to 20% of the seed crystals, and 5 to 10% of the sugar crystals.
% is preferable.

尚、本発明のジペプチド甘味料含有糖結晶に使
用する糖は1種類でも、2種以上を組合せたもの
でもよい。また、ジペプチド甘味料及び糖以外の
第3成分の使用も、本発明の目的達成上支障がな
い限り、排除されるものではない。
Note that the sugar crystals containing the dipeptide sweetener of the present invention may use one type of sugar or a combination of two or more types. Further, the use of a third component other than the dipeptide sweetener and sugar is not excluded as long as it does not interfere with achieving the objectives of the present invention.

このようにして得られる本発明のジペプチド甘
味料含有糖結晶は、従来の顆粒品、錠剤品等にな
い透明感、結晶感に富み、水に対する分散性、溶
解性も良好で、スツキリした上品な甘味質のロー
カロリー甘味料として提供できる。
The dipeptide sweetener-containing sugar crystals of the present invention thus obtained are rich in transparency and crystallinity that are not found in conventional granules, tablets, etc., have good dispersibility and solubility in water, and have a refreshing and elegant appearance. It can be provided as a sweet, low-calorie sweetener.

次に実施例により、本発明を更に説明する。 Next, the present invention will be further explained with reference to Examples.

実施例 1 AP50重量部及びシヨ糖100重量部を微粉砕混合
し、結合剤として水5重量部を用いて押出し造粒
した後、篩分し平均粒径100μの種晶を形成した。
Example 1 50 parts by weight of AP and 100 parts by weight of sucrose were pulverized and mixed, extruded and granulated using 5 parts by weight of water as a binder, and then sieved to form seed crystals with an average particle diameter of 100 μm.

上記種晶とシヨ糖とを各別に晶出カンに投入
し、APとシヨ糖の60℃飽和液を循環させて、本
発明のAP含有糖結晶を形成した。上記飽和液は、
予め80℃まで加温されて、シヨ糖と接触し、次い
で60まで冷却し、種晶と接触させた。
The above seed crystals and sucrose were separately placed in a crystallization can, and a 60°C saturated solution of AP and sucrose was circulated to form AP-containing sugar crystals of the present invention. The above saturated liquid is
It was prewarmed to 80°C and contacted with sucrose, then cooled to 60°C and contacted with seed crystals.

得られたAP含有糖結晶は、粒径300μで結晶形
成に要する時間は3時間であつた。また、外観は
デコボコした透明感のある白色結晶であり、この
結晶を60℃の温水に溶解したところ、グラニユー
糖と同程度に容易に溶解した。
The obtained AP-containing sugar crystals had a particle size of 300 μm, and the time required for crystal formation was 3 hours. In addition, it appeared as white crystals with a bumpy, transparent feel, and when these crystals were dissolved in warm water at 60°C, they dissolved as easily as granulated sugar.

実施例 2 実施例1と同様にして得たAP及びシヨ糖の混
合造粒品を粗種晶とし、実施例1と同様に、AP
とシヨ糖の60℃飽和液を循環させ、シヨ糖コーテ
イング部分が10%に達した段階で取出し、シヨ糖
でコーテイングされたAP−シヨ糖混合造粒品
(粒径100〜200μ)を得た。
Example 2 A mixed granulated product of AP and sucrose obtained in the same manner as in Example 1 was used as a coarse seed crystal, and in the same manner as in Example 1, AP was
A saturated solution of sucrose and sucrose was circulated at 60°C, and taken out when the sucrose coated portion reached 10% to obtain a granulated AP-sucrose mixture coated with sucrose (particle size 100 to 200μ). .

該シヨ糖コーテイングAP−シヨ糖混合造粒品
を種晶として、シヨ糖溶液中で濃縮晶析を行い、
本発明のAP含有糖結晶を得た。
Using the sucrose coated AP-sucrose mixed granules as seed crystals, concentrate and crystallize in a sucrose solution,
AP-containing sugar crystals of the present invention were obtained.

得られたAP含有糖結晶は、粒径300〜600μ、
シヨ糖結晶部分96%であり、結晶析出に要する時
間は5時間であつた。
The obtained AP-containing sugar crystals have a particle size of 300 to 600μ,
The sucrose crystal content was 96%, and the time required for crystal precipitation was 5 hours.

実施例 3 AP50重量部及び乳糖100重量部を微粉砕混合
し、結合剤としてグルタミン酸ナトリウム水溶液
20重量部を用いて、流動造粒を行い、AP−乳糖
混合造粒品(粒径50〜200μ)を得た。
Example 3 50 parts by weight of AP and 100 parts by weight of lactose were finely ground and mixed, and a sodium glutamate aqueous solution was added as a binder.
Fluidized granulation was performed using 20 parts by weight to obtain an AP-lactose mixed granulated product (particle size 50 to 200μ).

この混合造粒品を種晶として、AP、乳糖を各
別に収納した晶出カンに70%エタノールを媒体と
した60℃におけるAP及び乳糖の飽和液を実施例
1と同様に循環させ、乳糖結晶を晶析して、本発
明のAP含有糖結晶を得た。
Using this mixed granulated product as a seed crystal, a saturated solution of AP and lactose at 60°C in 70% ethanol as a medium was circulated in the crystallization can containing AP and lactose separately in the same manner as in Example 1, and lactose crystals were crystallized. was crystallized to obtain AP-containing sugar crystals of the present invention.

得られたAP含有糖結晶は、粒径300〜500μで
あり、結晶析出に要する時間は5時間であつた。
The obtained AP-containing sugar crystals had a particle size of 300 to 500 μm, and the time required for crystal precipitation was 5 hours.

実施例 4 AP25重量部、ステビオサイド50重量部及びシ
ヨ糖100重量部を微粉砕混合し、流動造粒して、
AP−ステビオサイド−シヨ糖混合造粒品(粗種
晶、粒径50〜200μ)を得た。
Example 4 25 parts by weight of AP, 50 parts by weight of stevioside and 100 parts by weight of sucrose were pulverized and mixed, fluidized and granulated.
A mixed granulated product of AP-stevioside-sucrose (coarse seed crystals, particle size 50-200μ) was obtained.

この粗種晶とシヨ糖とを各別の晶出カンに投入
し、AP、ステビオサイド及びシヨ糖の70℃にお
ける50%エタノール飽和液を実施例1と同様に循
環し、シヨ糖を晶出させて、シヨ糖コーテイング
品(シヨ糖コーテイング部分10%)を得、これを
種晶としてシヨ糖液中で濃縮晶析して本発明の
AP含有糖結晶を得た。
The crude seed crystals and sucrose were put into separate crystallization cans, and a 50% ethanol saturated solution of AP, stevioside, and sucrose at 70°C was circulated in the same manner as in Example 1 to crystallize sucrose. Then, a sucrose-coated product (sucrose coating portion: 10%) was obtained, which was used as a seed crystal to concentrate and crystallize in a sucrose solution to obtain the product of the present invention.
AP-containing sugar crystals were obtained.

得られたAP含有糖結晶は、粒径300〜500μ、
結晶形成に要する時間は5時間であつた。
The obtained AP-containing sugar crystals have a particle size of 300 to 500μ,
The time required for crystal formation was 5 hours.

Claims (1)

【特許請求の範囲】 1 ジペプチド甘味料及び糖を混合、造粒して成
る種晶の周囲に糖が晶析して成ることを特徴とす
るジペプチド甘味料含有糖結晶。 2 ジペプチド甘味料及び糖を混合、造粒し、こ
れを種晶として、ジペプチド甘味料飽和液及び糖
の過飽和液中で糖の結晶を成長させることを特徴
とするジペプチド甘味料含有糖結晶の製造法。 3 ジペプチド甘味料及び糖を混合、造粒し、こ
れを粗種晶として、ジペプチド甘味料飽和液及び
糖の過飽和液中で、糖を晶析したものを種晶と
し、晶析により更に糖の結晶を成長させることを
特徴とするジペプチド甘味料含有糖結晶の製造
法。
[Scope of Claims] 1. A dipeptide sweetener-containing sugar crystal, characterized in that sugar is crystallized around seed crystals formed by mixing and granulating a dipeptide sweetener and sugar. 2. Production of dipeptide sweetener-containing sugar crystals, which is characterized by mixing and granulating a dipeptide sweetener and sugar, and using this as a seed crystal to grow sugar crystals in a dipeptide sweetener saturated solution and a sugar supersaturated solution. Law. 3 Mix and granulate the dipeptide sweetener and sugar, use this as crude seed crystals, crystallize the sugar in a dipeptide sweetener saturated solution and a supersaturated sugar solution, use it as a seed crystal, and further crystallize the sugar. A method for producing sugar crystals containing a dipeptide sweetener, which comprises growing crystals.
JP57037547A 1982-03-10 1982-03-10 Sugar crystal containing dipeptide sweetener and its preparation Granted JPS58155054A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP57037547A JPS58155054A (en) 1982-03-10 1982-03-10 Sugar crystal containing dipeptide sweetener and its preparation

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP57037547A JPS58155054A (en) 1982-03-10 1982-03-10 Sugar crystal containing dipeptide sweetener and its preparation

Publications (2)

Publication Number Publication Date
JPS58155054A JPS58155054A (en) 1983-09-14
JPH0212546B2 true JPH0212546B2 (en) 1990-03-20

Family

ID=12500545

Family Applications (1)

Application Number Title Priority Date Filing Date
JP57037547A Granted JPS58155054A (en) 1982-03-10 1982-03-10 Sugar crystal containing dipeptide sweetener and its preparation

Country Status (1)

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JP (1) JPS58155054A (en)

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Publication number Priority date Publication date Assignee Title
JPS60256361A (en) * 1984-05-31 1985-12-18 Kato Kaneji Composite sweetener composed of fructose and aspartame and its preparation
JPH0659188B2 (en) * 1987-12-05 1994-08-10 三菱化成株式会社 Appearance Crystalline low-calorie sweetener composition manufacturing method
FR2639225B1 (en) * 1988-11-21 1993-05-21 Centre Nat Rech Scient PHARMACEUTICAL COMPOSITIONS FOR NEUROPROTECTION CONTAINING ARYLCYCLOHEXYLAMINES
US6214402B1 (en) * 1998-09-17 2001-04-10 The Nutrasweet Company Co-crystallization of sugar and n-[n-(3,3-dimethylbutyl)-l αaspartyl]-l-phenylalanine 1-methyl ester
US6365216B1 (en) * 1999-03-26 2002-04-02 The Nutrasweet Company Particles of N-[N-(3,3-dimethylbutyl)-L-α-aspartyl]-L-phenylalanine 1-methyl ester
US20080292775A1 (en) * 2007-05-22 2008-11-27 The Coca-Cola Company Delivery Systems for Natural High-Potency Sweetener Compositions, Methods for Their Formulation, and Uses

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