Movatterモバイル変換


[0]ホーム

URL:


JP2004344071A - Stevia sweetener composition - Google Patents

Stevia sweetener composition
Download PDF

Info

Publication number
JP2004344071A
JP2004344071AJP2003145062AJP2003145062AJP2004344071AJP 2004344071 AJP2004344071 AJP 2004344071AJP 2003145062 AJP2003145062 AJP 2003145062AJP 2003145062 AJP2003145062 AJP 2003145062AJP 2004344071 AJP2004344071 AJP 2004344071A
Authority
JP
Japan
Prior art keywords
stevioside
rebaudioside
steviol
sweetener composition
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.)
Granted
Application number
JP2003145062A
Other languages
Japanese (ja)
Other versions
JP4345961B2 (en
Inventor
Ayako Kato
藤 綾 子 嘉
Sumihisa Iida
田 純 久 飯
Takashi Yumoto
本 隆 湯
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.)
Toyo Sugar Refining Co Ltd
Original Assignee
Toyo Sugar Refining 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 Toyo Sugar Refining Co LtdfiledCriticalToyo Sugar Refining Co Ltd
Priority to JP2003145062ApriorityCriticalpatent/JP4345961B2/en
Publication of JP2004344071ApublicationCriticalpatent/JP2004344071A/en
Application grantedgrantedCritical
Publication of JP4345961B2publicationCriticalpatent/JP4345961B2/en
Anticipated expirationlegal-statusCritical
Expired - Lifetimelegal-statusCriticalCurrent

Links

Landscapes

Abstract

<P>PROBLEM TO BE SOLVED: To obtain an inexpensive stevia sweetener composition excellent in water solubility and taste without strange taste such as bitterness, and industrially easily producible at a low cost. <P>SOLUTION: This economical stevia sweetener composition excellent in water solubility and improved in taste is such one that stevioside is the main component of 6 kinds of steviol glycosides (steviol 6-glycoside) consisting of stevioside, rebaudioside A, dulcoside A, rebaudioside C, steviolbioside and rubusoside, the sum of stevioside and rebaudioside A (stevioside + rebaudioside A) covers ≥92 wt.%, preferably ≥95 wt.% of the sum of the steviol 6-glycoside, and stevioside covers ≥85 wt.% of the sum of the 6 kinds of steviol glycosides (steviol 6-glycoside). It is preferable that the stevia sweetener composition is obtained by mixing crystallized stevioside with crystallized rebaudioside A under heating in the presence of a solvent. <P>COPYRIGHT: (C)2005,JPO&NCIPI

Description

Translated fromJapanese

【0001】
【発明の技術分野】
本発明は、ステビア甘味料組成物に関し、さらに詳しくは、水溶性に優れ、呈味の改善されたステビア甘味料組成物に関する。
【0002】
【発明の技術的背景】
ステビアは、南米原産のキク科植物であって、その抽出物は、砂糖の数百倍の甘さを有し、ノンカロリーの高甘味度甘味料などとして古来より用いられているが、苦味などの異味も有している。
【0003】
ステビア葉から抽出精製して得られる「精製ステビア抽出物」には、甘味成分として、主に、ステビオシド(ステビオサイド)が50〜55重量%、レバウディオシド(レバウデオサイド)Aが20〜25重量%、レバウディオシドCが7〜8重量%、ズルコシド(ズルコサイド)Aが3〜4重量%(4成分の合計:100重量%)の4種のステビオール配糖体(ステビオール4配糖体とも言う。)が含まれており、その他に、ルブソシド、ステビオールビオシド、レバウディオシドD、レバウディオシドEなどのステビオール配糖体が少量(各0〜5重量%程度)ずつ含まれている。
(なお、「レバウディオシドC」の命名は、日本化学会誌1981年vol5、第726〜735頁の記載例による。)
ステビア葉やその抽出物には、上記のようにステビオシドが主成分として、最も多量に含まれ、次いで、レバウディオシドAが多く含まれている。
【0004】
ステビア葉やその抽出物に含まれるこれらの配糖体のうちで、レバウディオシドC、ズルコシドAは、ラムノシル基を有しており、ステビオシド、レバウディオシドAに比して苦味が強く、呈味がステビオシド、レバウディオシドAに比して劣っており、特にズルコシドAの呈味が悪い。そのため、レバウディオシドC、ズルコシドAの含有量の少ないステビア甘味料組成物が望まれていた。
【0005】
しかしながら、レバウディオシドC、ズルコシドAは、ステビオシド、レバウディオシドAと分子量も近似しており、吸着樹脂への親和性、水やアルコールへの溶解度などの点でも似た挙動を示すため、結晶化以外の精製法によるレバウディオシドC、ズルコシドAの低減は一般に困難であった。
【0006】
一方、結晶化によりステビオシドの含有率を大幅に高め、他の成分(例:レバウディオシドC、ズルコシドAなど)を低減することが行われており、かなりの呈味改善効果が得られている。
【0007】
しかし、得られたステビア甘味料組成物中におけるステビオシド含有率が高くなるに連れて、水溶性が著しく低下してしまうという問題点があった。さらに、ステビオールビオシドがステビオシドとほぼ同じ挙動をし、ステビオシド含量を高めようとするとそれに連れてステビオールビオシドも却って含有率が高くなってしまうという問題点があった。また、純粋なステビオシドあるいはレバウディオシドAと比較した場合、依然として雑味(すっきりしない曖昧な味)が目立ち、更なる呈味の改善が望まれていた。
【0008】
本発明者らは、上記問題点を解決すべく鋭意検討を重ねたところ、ステビア甘味料組成物の水溶性を良好に保つためには、主成分のステビオシドが「ステビオール6配糖体」中で一定割合以下の比率になっていること、そしてステビオシドを含む特定成分が「ステビオール6配糖体」中に特定割合以上の量で含まれていると、水溶性と良好な呈味が発揮されることを見出して、本発明を完成するに至った。
【0009】
なお、特開平4−148659号公報(特許文献1)には、全ステビオール配糖体に対して、レバウディオシドAを44重量%以上含有し、レバウディオシドCを0.5〜10重量%の量で含有するステビオール配糖体群からなるステビア甘味料およびそれを含む甘味食品が開示されている。
【0010】
しかしながら、該公報に記載のレバウディオシドA高含有率のステビア甘味料は、ステビアの品種改良によりレバウディオシドAの含有率を高めたステビア葉から得られたもので、今なお栽培地域が限られ、そのため価格が高く、一般食品に配合して広範に利用されるまでには至っていない。
【0011】
【特許文献1】
特開平4−148659号公報
【0012】
【発明の目的】
本発明は、上記のような従来技術に伴う問題点を解決しようとするものであって、水溶性に優れ、しかも苦味等の異味がなく、呈味に優れ、さらに工業的に容易に低コストで製造でき、低価格のステビア甘味料組成物を提供することを目的としている。
【0013】
【発明の概要】
本発明に係るステビア甘味料組成物は、ステビオシドが、ステビオシド、レバウディオシドA、ズルコシドA、レバウディオシドC、ステビオールビオシドおよびルブソシドの6種類のステビオール配糖体(ステビオール6配糖体)の主成分であり、ステビオシドとレバウディオシドAとの和(ステビオシド+レバウディオシドA)が、該ステビオール6配糖体合計の92重量%以上、好ましくは95重量%以上であり、且つステビオシドが前記6種類のステビオール配糖体(ステビオール6配糖体)合計の85重量%以下であることを特徴としている。
【0014】
本発明に係る上記ステビア甘味料組成物は、結晶化ステビオシドと結晶化レバウディオシドAとを、加熱下で溶媒の存在下に混合して得られるものであることが好ましい。
【0015】
本発明によれば、水溶性に優れ、しかも苦味等の異味がなく、呈味に優れたステビア甘味料組成物が、さらに工業的に容易に低コストで製造でき、低価格で提供される。
【0016】
【発明の具体的説明】
以下、本発明に係るステビア甘味料組成物について具体的に説明する。
【0017】
<ステビア甘味料組成物>
ステビアは、南米原産のキク科植物であって、その抽出物は、砂糖の数百倍の甘さを有し、苦味などの異味も有している。このステビア中の主な甘味成分は、特開2000−237571号公報中の図1、すなわち下記式[I]に示されるように、ステビオール(式[I]中、R:H、R:H)をアグリコンとし、このステビオールにグルコースまたはラムノースが結合した下記式[I](ステビオールを除く。)で表される種々のステビオール配糖体のうちの1種であるステビオシド(ステビオサイド)▲1▼やレバウディオシド(レバウディオサイド)Aなどであり、それらの甘味度は、ステビオシドでは砂糖の200〜250倍、レバウディオシドAでは砂糖の260〜300倍といわれる。
【0018】
【化1】

Figure 2004344071
【0019】
なお、ステビオール6配糖体とは、上記式[I]で表されるステビオールおよびその配糖体のうち、
ステビオシド(ステビオサイド)(▲1▼)、
レバウディオシド(レバウディオサイド)A(▲2▼)、
ズルコシド(ズルコサイド)A(▲3▼)、
レバウディオシド(レバウディオサイド)C(▲4▼)、
ステビオールビオシド(ステビオールバイオサイド)(▲7▼)、
ルブソシド(ルブソサイド)((10))、
の6種をいう。
【0020】
本発明に係るステビア甘味料組成物には、ステビオシドが、ステビオール6配糖体のうちの主成分として最大量で含まれ、レバウディオシドAよりも多く含まれている。
【0021】
しかも、このステビア甘味料組成物には、ステビオシドとレバウディオシドAとの和(ステビオシド+レバウディオシドA)が、ステビオール6配糖体の92重量%以上、好ましくは95重量%以上、特に好ましくは96〜100重量%となる量で含まれている。
【0022】
また本発明に係るステビア甘味料組成物にはステビオシドがステビオール6配糖体に対して85重量%以下の割合で含まれている。
【0023】
ステビア甘味料組成物中におけるステビオシドとレバウディオシドAとの和(ステビオシド+レバウディオシドA)が、特に、ステビオール6配糖体の92重量%未満であると、呈味質の劣るステビオール配糖体(レバウディオシドC、ズルコシドA、ステビオールビオシド)の甘味質が顕著に表れ呈味に影響してくる傾向がある。
【0024】
また、ステビア甘味料組成物中における(ステビオシド/ステビオール6配糖体)重量比率が85%を超えると水溶液中のステビオシドが析出しやすくなってくる。
【0025】
本発明に係るステビア甘味料組成物は、ステビオシドの含有率が一定範囲(85%)に抑えられているため、水溶性に優れ、室温下の水1リットルに対する溶解度は、約10g以上であり、実用上十分な溶解性が得られる。
【0026】
本発明に係るステビア甘味料組成物は、このように水溶性に優れ、しかも苦味等の異味がなく、呈味に優れている。
【0027】
なお、従来の通常のステビア抽出物は、通常、
ステビオシドを50〜55重量%、
レバウディオシドAを20〜25重量%、
レバウディオシドCを7〜8重量%、
ズルコシドAを3〜4重量%の量(但し、全成分の合計を100重量%とする。)で含むことが多い。
【0028】
<ステビア甘味料組成物の製造>
本発明に係る上記ステビア甘味料組成物は、上記各成分を上記所定量比で配合し、必要により溶媒などの存在下に、混合、攪拌等を行うことにより製造することができる。この際に、各成分が分解等の生じないような温度条件下で、加熱してもよい。
【0029】
すなわち、本発明に係る上記ステビア甘味料組成物を得るには、例えば、ステビオシドとレバウディオシドAとを含む式[I]で表されるステビオール配糖体を、その和(ステビオシド+レバウディオシドA)がステビオール6配糖体のうちの92重量%以上、好ましくは95重量%以上であり、しかもステビオシドがステビオール6配糖体中に85%以下で含まれるように調製すればよい。
【0030】
本発明では、上記ステビア甘味料組成物は、特に、結晶化ステビオシドと結晶化レバウディオシドAとを、加熱下で溶媒の存在下に上記量比で混合し溶解して得られるものであることがステビオール6配糖体中のステビオシドとレバウディオシドAの合計比率およびステビオール6配糖体中のステビオシドの含有比率(重量比)を容易にコントロールできる点から好ましい。
【0031】
また、上記ステビア甘味料組成物を調製する際には、必要により、水;メタノール、エタノール等の炭素数1〜5の低級アルコール;アセトン等のケトン;等の溶媒を用いることができ、また、これら溶媒は1種または2種以上混合して用いてもよい。
【0032】
また、本発明では、例えば、上記式[I]で表されるステビオール配糖体を含むステビア抽出物を溶媒、例えば、メタノール等のアルコール溶媒中で溶解した後、結晶化させ、ステビオシド、レバウディオシドAの含有率を高めたこの結晶を分取し、この結晶を水などの溶媒に溶解させ、次いで、イオン交換樹脂を用いて精製(カチオン交換樹脂→アニオン交換樹脂)を行うことによりステビオシドから糖が1個切れて生ずるステビオールビオシドなどを樹脂に吸着させたのち除去してその量を低減し、ステビオシド、レバウディオシドAが多量に含まれ、かつこれらが上記所定量比であり、ステビオシド含量が所定量以下であるような上記ステビア甘味料組成物を調製してもよい。
【0033】
この際に用いられる原料用のステビア抽出物としては、ステビオシドとレバウディオシドAとの含有比(ステビオシド/レバウディオシドA(重量比)=約7/3)の汎用品を用いることができ、前記ステビア品種改良品より得られたレバウディオシドA含量の高い高価品を用いる場合に比べて、安価に本発明品を製造できる。
【0034】
なお、ステビオシドに比してレバウディオシドAの含有量の多い市販のステビア抽出物は、価格が高いが、ステビオシド/レバウディオシドA(重量比)=約7/3の汎用品から結晶化で得られたステビオシド主体の結晶化品と組み合わせるなどして、所望の重量比になるように調整して用いると、より低コスト化を図ることができる。
【0035】
この場合、上記ステビア甘味料組成物は、原料として、ステビオシド量が多い結晶化ステビオシドと、原料としてレバウディオシドA量が多い結晶化レバウディオシドAとを、加熱下で水などの溶媒の存在下に、ステビオール6配糖体合計に対する(ステビオシド+レバウディオシドA)重量比およびステビオール6配糖体に対するステビオシドの含有量が所望の比率となるように混合・溶解して得られるものであってもよい。
【0036】
このようにステビオシドを多く含有する結晶と、レバウディオシドAを多く含有する結晶とを水などに溶解あるいは混合して用いると、各成分含有率などを正確にコントロールでき、優れたステビア甘味料組成物が得られる。
【0037】
<ステビア甘味料組成物の用途>
上記のようにして得られたステビア甘味料組成物は、安全性に優れ、ノンカロリーであることから、ダイエット甘味料、高甘味度甘味料として、従来のステビア甘味料が用いられていたような種々の食品に添加して用いることができる。
【0038】
上記食品としては、漬け物、珍味、水産練り製品、飲料、佃煮、調味料、冷菓、キャンデーその他の菓子類等が挙げられる。これら食品へのステビア甘味料組成物の添加量は、特に限定されず、食品の種類などにも依り、一概に決定されないが、食品中の該組成物(固形分)の含有量が、例えば、0.0001〜0.03重量%となるような量で配合される。
【0039】
【発明の効果】
本発明によれば、水溶性に優れ、しかも苦味等の異味がなく、呈味に優れ、高甘味度甘味料として種々の食品に添加して使用でき、しかも市販の安価な原料を用いて安価かつ容易に製造し得るステビア甘味料組成物が提供される。
【0040】
【実施例】
以下、本発明に係るステビア甘味料組成物について、実施例によりさらに具体的に説明するが、本発明は、係る実施例により何ら限定されるものではない。
【0041】
以下の実施例、比較例において、「%」は、特にその趣旨に反しない限り、「重量%」の意味である。
【0042】
【実施例1】
ステビア抽出物から得た高純度ステビオシド(ステビオシド含量99%)、高純度レバウデオシドA(レバウデオシドA含量98.5%)を種々の混合比及び濃度(1%溶液、0.1%溶液)でイオン交換水に入れ、90℃に加熱して、上記高純度ステビオシド及び高純度レバウディオシドAをイオン交換水に溶解したのち、常温(20℃)で2週間保持し、水中での安定性を調べた。
結果を表1〜表2に示す。
【0043】
なお、評価基準は、以下の通り。
「−」:析出なし
「+」:わずかに析出あり
「++」:析出あり
【0044】
【表1】
Figure 2004344071
【0045】
【表2】
Figure 2004344071
【0046】
<考察>
イオン交換水中の高純度ステビオシドと高純度レバウディオシドAの合計含有量が1%の溶液では、「高純度ステビオシド/高純度レバウディオシドA」(重量比)が▲1▼95/5、▲2▼90/10共に析出が見られ、特に▲1▼95/5では調製して1日後からステビオシドの析出が見られた。しかし、▲3▼85/15では2週間経っても安定であった。
【0047】
またイオン交換水中の高純度ステビオシドと高純度レバウディオシドAの合計含有量が0.1%溶液では、「高純度ステビオシド/高純度レバウディオシドA」(重量比)が▲1▼95/5で2週間後析出が見られたが、この重量比が▲2▼90/10、▲3▼85/15では安定であった。
【0048】
なお、ステビオシド量が85%より低い(レバウディオシドAが15%より高い)領域においても、表1、表2共に、重量比(高純度ステビオシド重量/高純度レバウデオシドA)が85/15の場合と同様の結果が得られた。
【0049】
【実施例2】
市販のステビア抽出物(前記「4配糖体」含量90.5%)100gを40℃で80%(v/v)メタノール500mlに溶解させ、一晩室温(20℃)で放置し、結晶を析出させ、固液分離し、結晶(イ)を得た。
【0050】
結晶(イ)中の成分を下記の条件下にHPLCで分析し、ステビオシド83.1%、レバウデオシドA5.20%、レバウデオシドC 1.10%、ズルコシドA0.82%、ルブソシド0.6%、ステビオールビオシド5.5% の組成を確認した。
【0051】
本品はステビオール6配糖体の合計量に対するステビオシド+レバウディオシドAの和の比率は91.7%であった。またステビオシドのステビオール6配糖体の合計量に対する比率は86.3%であった。
【0052】
本品を実施例1と同様に1%液を調製して常温(20℃)で保存したところ、3週間経過時析出が認められた。
<HPLC分析条件>
カラム:「YMC−Pack ODS−AQ」、株式会社ワイエムシー製、4.6mm×250mm、
検 出:UV 210nm、
移動相:アセトニトリル/水/酢酸=350/650/0.02(v/v)。
【0053】
本品(イ)4重量部とレバウデオシドA高含有製品(レバウデオシドA87.50%、ステビオシド 2.98%、レバウデオシドC1.47%、ズルコシドA0.00%、ルブソシド0.00%、ステビオールビオシド0.50%)1重量部を合わせ、水15重量部を加え、90℃に加熱してこれらを溶解した。その後、凍結乾燥しサンプル(本発明品1)を得た。
【0054】
得られた本発明品1の成分含量(重量%)は、ステビオシド67.08%、レバウデオシドA21.66%、レバウデオシドC1.17%、ズルコシドA0.66%、ルブソシド0.48%、ステビオールビオシド4.50%であった。
【0055】
本発明品1の一部(1重量部)を水4重量部に溶解させて、濃度約20%の水溶液とし、予め所定の方法で再生しておいたカチオン、アニオン交換樹脂に順次通液して精製し、出液を凍結乾燥して「本発明品2」を得た。「本発明品2」はステビオール6配糖体の1成分であるステビオールビオシドがほとんど除去されていた。
【0056】
得られた本発明品2の成分含量(重量%)は、ステビオシド70.22%、レバウディオシドA22.68%、レバウディオシドC1.22%、ズルコシドA0.68%、ルブソシド0.50%、ステビオールビオシド0.00%であった。
【0057】
本発明品1及び本発明品2の成分の分析結果を併せて、表3に示した。
【0058】
【表3】
Figure 2004344071
【0059】
実施例2で得られた本発明品1,2と、比較品1として、市販のステビア抽出物(ステビオシド52.69%、レバウデオシドA23.74%、レバウデオシドC7.74%、ズルコシドA3.17%、ルブソシド1.20%、ステビオールビオシド0.19%)を用い、各々をステビオール配糖体含量0.03%水溶液に調整してパネラー10名で呈味比較試験を行った。
【0060】
各サンプルの平均スコアを表4に示す。
【0061】
なお、評価方法は、比較品を基準(評価:0)にして、下記評価基準に従い、甘味の立ち上り、後引き、異味、総合評価について、それぞれ±3段階で評価した。
【0062】
<評価基準>
甘味の立ち上がり:+3(速い)〜―3(遅い)
甘味の後引き:+3(弱い)〜―3(強い)
異 味:+3(感じない)〜―3(感じる)
総合評価:+3(良い)〜―3(悪い)
【0063】
【表4】
Figure 2004344071
【0064】
本発明品1では比較品(市販の一般製品)に比べ、甘味の立ち上がりが早、高甘味料特有の後引きも改善し、更に異味が少なくなっている。ステビオール6配糖体に対するステビオシドとレバウディオシドAの和の比率が更に改善した本発明品2ではこの傾向が一層高まっている。[0001]
TECHNICAL FIELD OF THE INVENTION
The present invention relates to a stevia sweetener composition, and more particularly, to a stevia sweetener composition having excellent water solubility and improved taste.
[0002]
TECHNICAL BACKGROUND OF THE INVENTION
Stevia is an Asteraceae plant native to South America, and its extract has hundreds of times the sweetness of sugar and has been used since ancient times as a non-caloric high-intensity sweetener, but has a bitter taste. Also has an off-flavor.
[0003]
The “purified stevia extract” obtained by extracting and purifying from stevia leaves is mainly composed of 50 to 55% by weight of stevioside (stevioside), 20 to 25% by weight of rebaudioside (rebaudioside) A, and rebaudioside C as sweetening components. Of steviol glycosides (also referred to as steviol tetraglycoside) in which 7 to 8% by weight and 3 to 4% by weight (dulcoside) A (total of four components: 100% by weight) are contained. In addition, steviol glycosides such as rubusoside, steviolbioside, rebaudioside D, and rebaudioside E are contained in small amounts (each about 0 to 5% by weight).
(Note that the name of “Rebaudioside C” is based on the description example in the Chemical Society of Japan, 1981, vol 5, pages 726 to 735.)
As described above, stevia leaf and its extract contain the largest amount of stevioside as a main component, followed by a large amount of rebaudioside A.
[0004]
Among these glycosides contained in stevia leaves and their extracts, rebaudioside C and dulcoside A have a rhamnosyl group, and have a stronger bitterness and a stronger taste than stevioside and rebaudioside A. It is inferior to rebaudioside A, and in particular, the taste of zurcoside A is poor. For this reason, a stevia sweetener composition having a low content of rebaudioside C and durucoside A has been desired.
[0005]
However, rebaudioside C and durucoside A also have similar molecular weights to stevioside and rebaudioside A, and exhibit similar behaviors in terms of affinity for an adsorption resin, solubility in water and alcohol, and the like. It was generally difficult to reduce rebaudioside C and durucoside A by the method.
[0006]
On the other hand, the content of stevioside is greatly increased by crystallization, and other components (eg, rebaudioside C, durucoside A, etc.) are reduced, and a considerable taste improving effect is obtained.
[0007]
However, there was a problem that as the stevioside content in the obtained stevia sweetener composition was increased, the water solubility was significantly reduced. Further, there is a problem that steviolbioside behaves almost the same as stevioside, and if the content of steviolside is to be increased, the content of steviolbioside is rather increased accordingly. Further, when compared with pure stevioside or rebaudioside A, unpleasant taste (unclear and unclear taste) is still conspicuous, and further improvement in taste has been desired.
[0008]
The present inventors have conducted intensive studies to solve the above problems, and found that, in order to keep the water solubility of the stevia sweetener composition good, the main component stevioside was contained in “steviol 6-glycoside”. If the ratio is not more than a certain ratio, and the specific component containing stevioside is contained in the “steviol hexaglycoside” in an amount not less than the specific ratio, water solubility and good taste are exhibited. This led to the completion of the present invention.
[0009]
JP-A-4-14859 (Patent Document 1) discloses that rebaudioside A is contained in an amount of not less than 44% by weight and rebaudioside C is contained in an amount of 0.5 to 10% by weight based on all steviol glycosides. A stevia sweetener comprising a group of steviol glycosides and a sweet food containing the same are disclosed.
[0010]
However, the stevia sweetener having a high content of rebaudioside A described in the publication is obtained from stevia leaves in which the content of rebaudioside A is increased by breeding of stevia, and the cultivation area is still limited. And it has not been widely used in general foods.
[0011]
[Patent Document 1]
Japanese Patent Application Laid-Open No. 4-148659 / 1990
[Object of the invention]
The present invention is intended to solve the problems associated with the prior art as described above, and is excellent in water solubility, has no unpleasant taste such as bitterness, is excellent in taste, and is industrially easily reduced in cost. It is an object of the present invention to provide a low-cost stevia sweetener composition.
[0013]
Summary of the Invention
In the stevia sweetener composition according to the present invention, stevioside is a main component of six types of steviol glycosides (steviol hexaglycoside) of stevioside, rebaudioside A, dulcoside A, rebaudioside C, steviolbioside and rubusoside. The sum of stevioside and rebaudioside A (stevioside + rebaudioside A) is at least 92% by weight, preferably at least 95% by weight of the total of steviol 6-glycosides, and the stevioside is the six types of steviol glycosides ( (Steviol 6-glycoside) is 85% by weight or less of the total.
[0014]
The stevia sweetener composition according to the present invention is preferably obtained by mixing crystallized stevioside and crystallized rebaudioside A with heating in the presence of a solvent.
[0015]
ADVANTAGE OF THE INVENTION According to this invention, the stevia sweetener composition which is excellent in water solubility, has no unpleasant tastes, such as bitterness, etc., and is excellent in taste can be further industrially easily manufactured at low cost, and is provided at low cost.
[0016]
DETAILED DESCRIPTION OF THE INVENTION
Hereinafter, the stevia sweetener composition according to the present invention will be specifically described.
[0017]
<Stevia sweetener composition>
Stevia is an Asteraceae plant native to South America, and its extract is hundreds of times sweeter than sugar and has an off-flavor such as bitterness. As shown in FIG. 1 in JP-A-2000-237571, that is, as shown in the following formula [I], steviol (in the formula [I], R1 : H, R2 : H) is an aglycone, and steviol (stevioside), which is one of various steviol glycosides represented by the following formula [I] (excluding steviol) in which glucose or rhamnose is bound to this steviol (1) And rebaudioside (rebaudioside) A, and their sweetness is said to be 200 to 250 times that of sugar for stevioside and 260 to 300 times that of sugar for rebaudioside A.
[0018]
Embedded image
Figure 2004344071
[0019]
In addition, the steviol 6 glycoside is the steviol represented by the above formula [I] and its glycoside,
Stevioside (Stevioside) (1),
Rebaudioside (rebaudioside) A (2),
Zurcoside (Zurcoside) A (3),
Rebaudioside (rebaudioside) C (▲ 4 ▼),
Steviol bioside (Steviol biocide) (▲ 7 ▼),
Rubusoside (rubusoside) ((10)),
Of the six types.
[0020]
In the stevia sweetener composition according to the present invention, stevioside is contained in the maximum amount as a main component of steviol 6-glycoside, and is contained more than rebaudioside A.
[0021]
Moreover, in the stevia sweetener composition, the sum of stevioside and rebaudioside A (stevioside + rebaudioside A) is 92% by weight or more, preferably 95% by weight or more, and particularly preferably 96 to 100% by weight of steviol 6-glycoside. % By weight.
[0022]
The stevia sweetener composition according to the present invention contains stevioside at a ratio of not more than 85% by weight based on steviol 6-glycoside.
[0023]
When the sum of stevioside and rebaudioside A (stevioside + rebaudioside A) in the stevia sweetener composition is less than 92% by weight of steviol 6-glycoside, steviol glycoside (rebaudioside C) having inferior taste is inferior. , Dulcoside A, steviol bioside) tend to be noticeable and affect the taste.
[0024]
Further, when the weight ratio of (stevioside / steviol hexaglycoside) in the stevia sweetener composition exceeds 85%, stevioside in the aqueous solution tends to precipitate.
[0025]
The stevia sweetener composition according to the present invention is excellent in water solubility because the content of stevioside is suppressed to a certain range (85%), and has a solubility of about 10 g or more in 1 liter of water at room temperature. Practically sufficient solubility is obtained.
[0026]
The stevia sweetener composition according to the present invention is thus excellent in water solubility, has no off-flavor such as bitterness, and is excellent in taste.
[0027]
In addition, conventional ordinary stevia extract is usually
50-55% by weight of stevioside,
20 to 25% by weight of rebaudioside A,
7-8% by weight of rebaudioside C,
Dulcoside A is often contained in an amount of 3 to 4% by weight (provided that the total of all components is 100% by weight).
[0028]
<Manufacture of stevia sweetener composition>
The above-mentioned stevia sweetener composition according to the present invention can be produced by mixing the above-mentioned components at the above-mentioned predetermined ratios and, if necessary, mixing and stirring in the presence of a solvent or the like. At this time, heating may be performed under a temperature condition that does not cause decomposition of each component.
[0029]
That is, in order to obtain the above-mentioned stevia sweetener composition according to the present invention, for example, a steviol glycoside represented by the formula [I] containing stevioside and rebaudioside A, and the sum (stevioside + rebaudioside A) of steviol are used. The content may be 92% by weight or more, preferably 95% by weight or more of the hexaglucoside, and stevioside may be prepared so as to be contained in the steviol 6-glucoside at 85% or less.
[0030]
In the present invention, in particular, the stevia sweetener composition is preferably obtained by mixing and dissolving crystallized stevioside and crystallized rebaudioside A in the above-described ratio in the presence of a solvent under heating. It is preferable because the total ratio of stevioside and rebaudioside A in the hexaglucoside and the content ratio (weight ratio) of stevioside in the steviol hexaglucoside can be easily controlled.
[0031]
When the stevia sweetener composition is prepared, a solvent such as water; a lower alcohol having 1 to 5 carbon atoms such as methanol and ethanol; a ketone such as acetone; can be used, if necessary. These solvents may be used alone or in combination of two or more.
[0032]
Further, in the present invention, for example, a stevia extract containing the steviol glycoside represented by the above formula [I] is dissolved in a solvent, for example, an alcohol solvent such as methanol, and then crystallized to obtain stevioside, rebaudioside A. The crystals having an increased content of are separated, and the crystals are dissolved in a solvent such as water, and then purified using an ion exchange resin (cation exchange resin → anion exchange resin), whereby sugars are obtained from stevioside. Steviol bioside and the like generated by cutting one piece are adsorbed to the resin and then removed to reduce the amount. Stevioside and rebaudioside A are contained in a large amount, and the ratio is the above-mentioned predetermined amount, and the content of stevioside is a predetermined amount. The above stevia sweetener composition may be prepared as follows.
[0033]
As the stevia extract for the raw material used at this time, a general-purpose product having a content ratio of stevioside to rebaudioside A (stevioside / rebaudioside A (weight ratio) = about 7/3) can be used. The product of the present invention can be produced at a lower cost than when an expensive product having a high rebaudioside A content obtained from the product is used.
[0034]
A commercially available stevia extract having a higher content of rebaudioside A than stevioside is expensive, but stevioside obtained by crystallization from a general-purpose product of stevioside / rebaudioside A (weight ratio) = about 7/3. If the weight ratio is adjusted to a desired weight ratio by combining with a crystallized product as a main component, the cost can be further reduced.
[0035]
In this case, the stevia sweetener composition comprises, as raw materials, crystallized stevioside having a large amount of stevioside and crystallized rebaudioside A having a large amount of rebaudioside A as raw materials, and adding steviol under heating in the presence of a solvent such as water. It may be obtained by mixing and dissolving so that the weight ratio of (stevioside + rebaudioside A) to the total of 6-glucosides and the content of stevioside to the steviol 6-glucosides become a desired ratio.
[0036]
When a crystal containing a large amount of stevioside and a crystal containing a large amount of rebaudioside A are dissolved or mixed in water or the like and used as described above, the content of each component can be accurately controlled, and an excellent stevia sweetener composition can be obtained. can get.
[0037]
<Use of Stevia sweetener composition>
The stevia sweetener composition obtained as described above is excellent in safety and non-caloric, so that as a diet sweetener, a high sweetness degree sweetener, a conventional stevia sweetener was used. It can be used by adding to various foods.
[0038]
Examples of the food include pickles, delicacies, fish paste products, beverages, boiled soy sauce, seasonings, frozen desserts, candy, and other confections. The amount of the stevia sweetener composition to be added to these foods is not particularly limited and depends on the type of food and the like, and is not absolutely determined. However, the content of the composition (solid content) in the food may be, for example, It is blended in an amount so as to be 0.0001 to 0.03% by weight.
[0039]
【The invention's effect】
ADVANTAGE OF THE INVENTION According to this invention, it is excellent in water solubility, and it has no off-flavors, such as a bitter taste, is excellent in taste, can be used by adding to various foods as a high-intensity sweetener, and is inexpensive using commercially available inexpensive raw materials A stevia sweetener composition is provided that is easy to produce.
[0040]
【Example】
Hereinafter, the stevia sweetener composition according to the present invention will be described more specifically with reference to examples, but the present invention is not limited to the examples.
[0041]
In the following Examples and Comparative Examples, “%” means “% by weight” unless specifically contradicted.
[0042]
Embodiment 1
Ion exchange high purity stevioside (99% stevioside content) and high purity rebadeoside A (98.5% rebadeoside A content) obtained from Stevia extract at various mixing ratios and concentrations (1% solution, 0.1% solution) After putting in water and heating to 90 ° C., the above-mentioned high-purity stevioside and high-purity rebaudioside A were dissolved in ion-exchanged water, kept at room temperature (20 ° C.) for 2 weeks, and examined for stability in water.
The results are shown in Tables 1 and 2.
[0043]
The evaluation criteria are as follows.
“−”: No precipitation “+”: slight precipitation “++”: precipitation
[Table 1]
Figure 2004344071
[0045]
[Table 2]
Figure 2004344071
[0046]
<Discussion>
In a solution in which the total content of high-purity stevioside and high-purity rebaudioside A in ion-exchanged water is 1%, “high-purity stevioside / high-purity rebaudioside A” (weight ratio) is (1) 95/5, (2) 90 / Precipitation was observed in all 10 samples, and particularly in (1) 95/5, precipitation of stevioside was observed one day after preparation. However, in (3) 85/15, it was stable even after 2 weeks.
[0047]
In the case of a 0.1% total solution of high-purity stevioside and high-purity rebaudioside A in ion-exchanged water, “high-purity stevioside / high-purity rebaudioside A” (weight ratio) was (1) 95/5 after 2 weeks. Although precipitation was observed, the weight ratio was stable at (2) 90/10 and (3) 85/15.
[0048]
In the region where the amount of stevioside is lower than 85% (rebaudioside A is higher than 15%), in both Tables 1 and 2, the weight ratio (weight of high-purity stevioside / high-purity rebaudioside A) is the same as in the case of 85/15. Was obtained.
[0049]
Embodiment 2
100 g of a commercially available stevia extract (the above “tetraglycoside” content: 90.5%) is dissolved in 500 ml of 80% (v / v) methanol at 40 ° C., and left overnight at room temperature (20 ° C.) to remove crystals. The crystals were precipitated and subjected to solid-liquid separation to obtain crystals (a).
[0050]
The components in the crystal (a) were analyzed by HPLC under the following conditions, and Stevioside 83.1%, Rebaudioside A 5.20%, Rebaudioside C 1.10%, Zurcoside A 0.82%, Rubusoside 0.6%, Steviol A composition of 5.5% bioside was confirmed.
[0051]
In this product, the ratio of the sum of stevioside + rebaudioside A to the total amount of steviol 6-glucoside was 91.7%. The ratio of stevioside to the total amount of steviol-6-glycosides was 86.3%.
[0052]
When a 1% solution of this product was prepared in the same manner as in Example 1 and stored at room temperature (20 ° C.), precipitation was observed after 3 weeks.
<HPLC analysis conditions>
Column: “YMC-Pack ODS-AQ”, manufactured by YMC, 4.6 mm × 250 mm,
Detection: UV 210 nm,
Mobile phase: acetonitrile / water / acetic acid = 350/650 / 0.02 (v / v).
[0053]
4 parts by weight of this product (a) and a product containing high content of rebaudioside A (rebaudioside A 87.50%, stevioside 2.98%, rebaudioside C 1.47%, dulucoside A 0.00%, rubusoside 0.00%, steviolbioside 0. (1% by weight), 15 parts by weight of water were added, and the mixture was heated to 90 ° C. to dissolve them. Thereafter, the sample was freeze-dried to obtain a sample (product 1 of the present invention).
[0054]
The component content (% by weight) of the obtained product 1 of the present invention is as follows: stevioside 67.08%, rebadeoside A 21.66%, rebadeoside C 1.17%, durucoside A 0.66%, rubusoside 0.48%, steviolbioside 4 .50%.
[0055]
A part (1 part by weight) of the product 1 of the present invention is dissolved in 4 parts by weight of water to form an aqueous solution having a concentration of about 20%, and the solution is sequentially passed through a cation and anion exchange resin which has been regenerated by a predetermined method. The product was freeze-dried to obtain "Product 2 of the present invention". "Product 2 of the present invention" had almost completely removed steviol bioside, which is one component of steviol 6-glycoside.
[0056]
The component content (% by weight) of the obtained product 2 of the present invention is as follows: stevioside 70.22%, rebaudioside A 22.68%, rebaudioside C 1.22%, durucoside A 0.68%, rubusoside 0.50%, steviolbioside 0 0.000%.
[0057]
Table 3 shows the analysis results of the components of the invention product 1 and the invention product 2 together.
[0058]
[Table 3]
Figure 2004344071
[0059]
Commercially available stevia extracts (52.69% stevioside, 23.74% rebadeoside A, 7.74% rebadeoside C, 3.17% zurcoside A) as inventive products 1 and 2 obtained in Example 2 and comparative product 1 Using rubusoside 1.20% and steviol bioside 0.19%), each was adjusted to a 0.03% aqueous solution of steviol glycoside, and a taste comparison test was conducted by 10 panelists.
[0060]
Table 4 shows the average score of each sample.
[0061]
The evaluation method was based on a comparative product (evaluation: 0), and according to the following evaluation criteria, the rise of sweetness, the after-drawing, the off-flavor, and the overall evaluation were evaluated in three steps.
[0062]
<Evaluation criteria>
Rise of sweetness: +3 (fast) to -3 (slow)
Sweetness subtraction: +3 (weak) to -3 (strong)
Offensive: +3 (not felt) to -3 (feels)
Overall rating: +3 (good) to -3 (bad)
[0063]
[Table 4]
Figure 2004344071
[0064]
Compared with the comparative product (commercially available general product), the product 1 of the present invention has a faster onset of sweetness, improved aftertaste peculiar to the high sweetener, and further reduced off-flavor. This tendency is further enhanced in the product 2 of the present invention in which the ratio of the sum of stevioside and rebaudioside A to steviol 6-glycoside is further improved.

Claims (3)

Translated fromJapanese
ステビオシドが、ステビオシド、レバウディオシドA、ズルコシドA、レバウディオシドC、ステビオールビオシドおよびルブソシドの6種類のステビオール配糖体(ステビオール6配糖体)の主成分であり、ステビオシドとレバウディオシドAとの和(ステビオシド+レバウディオシドA)が、該ステビオール6配糖体合計の92重量%以上であり、且つステビオシドが前記ステビオール6配糖体の合計の85重量%以下であることを特徴とするステビア甘味料組成物。Stevioside is the main component of six types of steviol glycosides (steviol hexaglycoside) of stevioside, rebaudioside A, dulcoside A, rebaudioside C, steviolbioside and rubusoside, and the sum of stevioside and rebaudioside A (stevioside + Stevia sweetener composition characterized in that rebaudioside A) is at least 92% by weight of the total steviol 6-glycoside and stevioside is at most 85% by weight of the total steviol 6-glycoside.上記ステビオシドとレバウディオシドAとの和(ステビオシド+レバウディオシドA)が、上記ステビオール6配糖体の合計の95重量%以上であることを特徴とする請求項1に記載のステビア甘味料組成物。The stevia sweetener composition according to claim 1, wherein the sum of the stevioside and rebaudioside A (stevioside + rebaudioside A) is 95% by weight or more of the total of the steviol hexaglycoside.上記ステビア甘味料組成物は、結晶化ステビオシドと結晶化レバウディオシドAとを、加熱下で溶媒の存在下に混合して得られるものであることを特徴とする請求項1〜2の何れかに記載のステビア甘味料組成物。The stevia sweetener composition is obtained by mixing crystallized stevioside and crystallized rebaudioside A in the presence of a solvent under heating, and wherein the stevia sweetener composition is obtained by mixing in a solvent. Stevia sweetener composition.
JP2003145062A2003-05-222003-05-22 Stevia sweetener compositionExpired - LifetimeJP4345961B2 (en)

Priority Applications (1)

Application NumberPriority DateFiling DateTitle
JP2003145062AJP4345961B2 (en)2003-05-222003-05-22 Stevia sweetener composition

Applications Claiming Priority (1)

Application NumberPriority DateFiling DateTitle
JP2003145062AJP4345961B2 (en)2003-05-222003-05-22 Stevia sweetener composition

Publications (2)

Publication NumberPublication Date
JP2004344071Atrue JP2004344071A (en)2004-12-09
JP4345961B2 JP4345961B2 (en)2009-10-14

Family

ID=33532348

Family Applications (1)

Application NumberTitlePriority DateFiling Date
JP2003145062AExpired - LifetimeJP4345961B2 (en)2003-05-222003-05-22 Stevia sweetener composition

Country Status (1)

CountryLink
JP (1)JP4345961B2 (en)

Cited By (31)

* Cited by examiner, † Cited by third party
Publication numberPriority datePublication dateAssigneeTitle
JP2007082482A (en)*2005-09-222007-04-05Kikkoman Corp Proanthocyanidin-containing food and process for producing the same
JP2009517042A (en)*2005-11-232009-04-30ザ・コカ−コーラ・カンパニー Edible gel composition containing high-potency sweetener
JP2010535022A (en)*2007-08-012010-11-18キャドバリ ホールディングス リミテッド Sweetener composition
JP2011505344A (en)*2007-12-032011-02-24ディーエスエム アイピー アセッツ ビー.ブイ. Novel nutritional food composition containing stevia extract or stevia extract constituent and use thereof
RU2425589C2 (en)*2005-11-232011-08-10Дзе Кока-Кола КомпаниIntensive natural table sweetener composition
US8017168B2 (en)2006-11-022011-09-13The Coca-Cola CompanyHigh-potency sweetener composition with rubisco protein, rubiscolin, rubiscolin derivatives, ace inhibitory peptides, and combinations thereof, and compositions sweetened therewith
RU2437573C2 (en)*2005-11-232011-12-27Дзе Кока-Кола КомпаниComposition for intensive sweetener with calcium and compositions sweetened therewith
WO2012006728A1 (en)*2010-07-152012-01-19Glg Life Tech CorporationSweetener compositions and methods of making same
WO2012088598A1 (en)*2010-12-302012-07-05Glg Life Tech CorporationProcesses of purifying steviol glycosides
EP2416670A4 (en)*2009-04-092014-05-21Cargill IncSweetener composition comprising high solubility form of rebaudioside a and method of making
US8937168B2 (en)2007-01-222015-01-20Cargill, IncorporatedMethod of producing purified rebaudioside A compositions using solvent/antisolvent crystallization
US8940351B2 (en)2005-11-232015-01-27The Coca-Cola CompanyBaked goods comprising high-potency sweetener
US8956677B2 (en)2005-11-232015-02-17The Coca-Cola CompanyHigh-potency sweetener composition with glucosamine and compositions sweetened therewith
JP2015033387A (en)*2005-11-232015-02-19ザ コカ・コーラ カンパニーThe Coca‐Cola CompanyHigh-potency sweetener compositions with mineral and compositions sweetened therewith
EP2753189A4 (en)*2011-09-072015-06-03Purecircle Usa IncHighly soluble stevia sweetener
JP2015100274A (en)*2013-11-212015-06-04池田食研株式会社Packed composition
US9101160B2 (en)2005-11-232015-08-11The Coca-Cola CompanyCondiments with high-potency sweetener
US9131720B2 (en)2005-11-232015-09-15The Coca-Cola CompanyHigh-potency sweetener composition with phytosterol and compositions sweetened therewith
US9131718B2 (en)2009-06-162015-09-15Epc (Beijing) Natural Products Co., Ltd.Process for rebaudioside D
US9173425B2 (en)2005-11-232015-11-03The Coca-Cola CompanyHigh-potency sweetener composition with vitamin and compositions sweetened therewith
JP2016163580A (en)*2011-01-282016-09-08テート アンド ライル イングリーディエンツ アメリカズ エルエルシー Stevia blend containing Rebaudioside B
US9578895B2 (en)2010-08-232017-02-28Epc (Beijing) Natural Products Co., Ltd.Rebaudioside A and stevioside compositions
US9795156B2 (en)2011-03-172017-10-24E.P.C (Beijing) Plant Pharmaceutical Technology Co., LtdRebaudioside B and derivatives
JP2018536411A (en)*2015-11-242018-12-13フイルメニツヒ ソシエテ アノニムFirmenich Sa Glucosylated terpene glycoside
US10264811B2 (en)2014-05-192019-04-23Epc Natural Products Co., Ltd.Stevia sweetener with improved solubility
EP3488844A1 (en)*2011-02-102019-05-29PureCircle USA Inc.A method for producing a stevia sweetener
US10357052B2 (en)2014-06-162019-07-23Sweet Green Fields USA LLCRebaudioside A and stevioside with improved solubilities
US10485256B2 (en)2014-06-202019-11-26Sweet Green Fields International Co., LimitedStevia sweetener with improved solubility with a cyclodextrin
CN114340404A (en)*2019-08-282022-04-12三得利控股株式会社 Steviol glycoside composition and method for producing steviol glycoside composition from dried leaves of Stevia plant
WO2023100136A1 (en)*2021-12-012023-06-08Almendra (Thailand) Ltd.Methods and compositions for improved sugar-like taste
CN117106000A (en)*2023-07-172023-11-24华南理工大学 A kind of steviol glycoside aggregate and its preparation method and application

Cited By (48)

* Cited by examiner, † Cited by third party
Publication numberPriority datePublication dateAssigneeTitle
JP2007082482A (en)*2005-09-222007-04-05Kikkoman Corp Proanthocyanidin-containing food and process for producing the same
US8940351B2 (en)2005-11-232015-01-27The Coca-Cola CompanyBaked goods comprising high-potency sweetener
JP2009517042A (en)*2005-11-232009-04-30ザ・コカ−コーラ・カンパニー Edible gel composition containing high-potency sweetener
US9173425B2 (en)2005-11-232015-11-03The Coca-Cola CompanyHigh-potency sweetener composition with vitamin and compositions sweetened therewith
RU2425589C2 (en)*2005-11-232011-08-10Дзе Кока-Кола КомпаниIntensive natural table sweetener composition
RU2437573C2 (en)*2005-11-232011-12-27Дзе Кока-Кола КомпаниComposition for intensive sweetener with calcium and compositions sweetened therewith
US9131720B2 (en)2005-11-232015-09-15The Coca-Cola CompanyHigh-potency sweetener composition with phytosterol and compositions sweetened therewith
US9101160B2 (en)2005-11-232015-08-11The Coca-Cola CompanyCondiments with high-potency sweetener
JP2015033387A (en)*2005-11-232015-02-19ザ コカ・コーラ カンパニーThe Coca‐Cola CompanyHigh-potency sweetener compositions with mineral and compositions sweetened therewith
US8956677B2 (en)2005-11-232015-02-17The Coca-Cola CompanyHigh-potency sweetener composition with glucosamine and compositions sweetened therewith
US8017168B2 (en)2006-11-022011-09-13The Coca-Cola CompanyHigh-potency sweetener composition with rubisco protein, rubiscolin, rubiscolin derivatives, ace inhibitory peptides, and combinations thereof, and compositions sweetened therewith
US8937168B2 (en)2007-01-222015-01-20Cargill, IncorporatedMethod of producing purified rebaudioside A compositions using solvent/antisolvent crystallization
JP2010535022A (en)*2007-08-012010-11-18キャドバリ ホールディングス リミテッド Sweetener composition
JP2011505344A (en)*2007-12-032011-02-24ディーエスエム アイピー アセッツ ビー.ブイ. Novel nutritional food composition containing stevia extract or stevia extract constituent and use thereof
EP2416670A4 (en)*2009-04-092014-05-21Cargill IncSweetener composition comprising high solubility form of rebaudioside a and method of making
US9635878B2 (en)2009-06-162017-05-02Epc (Beijing) Natural Products Co., Ltd.Process for rebaudioside D
US9131718B2 (en)2009-06-162015-09-15Epc (Beijing) Natural Products Co., Ltd.Process for rebaudioside D
WO2012006728A1 (en)*2010-07-152012-01-19Glg Life Tech CorporationSweetener compositions and methods of making same
US11202462B2 (en)2010-08-232021-12-21Sweet Green Fields International Co., LimitedRebaudioside A and stevioside compositions
US10285425B2 (en)2010-08-232019-05-14Epc Natural Products Co. LtdRebaudioside A and stevioside compositions
US9578895B2 (en)2010-08-232017-02-28Epc (Beijing) Natural Products Co., Ltd.Rebaudioside A and stevioside compositions
WO2012088598A1 (en)*2010-12-302012-07-05Glg Life Tech CorporationProcesses of purifying steviol glycosides
JP2016163580A (en)*2011-01-282016-09-08テート アンド ライル イングリーディエンツ アメリカズ エルエルシー Stevia blend containing Rebaudioside B
US11801402B2 (en)2011-01-282023-10-31Tate & Lyle Solutions Usa LlcStevia blends containing rebaudioside b
US10583314B2 (en)2011-01-282020-03-10Tate & Lyle Ingredients Americas LlcStevia blends containing rebaudioside B
EP3488844A1 (en)*2011-02-102019-05-29PureCircle USA Inc.A method for producing a stevia sweetener
US11856974B2 (en)2011-02-102024-01-02Purecircle Sdn BhdHighly soluble stevia sweetener
EP3799857A1 (en)*2011-02-102021-04-07PureCircle USA Inc.A method for producing a stevia sweetener
US11510428B2 (en)2011-03-172022-11-29Sweet Green Fields International Co., LimitedRebaudioside B and derivatives
US9795156B2 (en)2011-03-172017-10-24E.P.C (Beijing) Plant Pharmaceutical Technology Co., LtdRebaudioside B and derivatives
EP2753189A4 (en)*2011-09-072015-06-03Purecircle Usa IncHighly soluble stevia sweetener
US11464246B2 (en)2011-09-072022-10-11Purecircle Sdn BhdHighly soluble Stevia sweetener
US11957149B2 (en)2011-09-072024-04-16Purecircle Sdn BhdHighly soluble stevia sweetener
JP2015100274A (en)*2013-11-212015-06-04池田食研株式会社Packed composition
US11206857B2 (en)2014-05-192021-12-28Sweet Green Fields International Co., LimitedStevia sweetener with improved solubility
US10561165B2 (en)2014-05-192020-02-18Sweet Green Fields International Co., LimitedStevia sweetener with improved solubility
US10264811B2 (en)2014-05-192019-04-23Epc Natural Products Co., Ltd.Stevia sweetener with improved solubility
US10568351B2 (en)2014-06-162020-02-25Sweet Green Fields USA LLCRebaudioside A and stevioside with improved solubilities
US11241031B2 (en)2014-06-162022-02-08Sweet Green Fields Usa, LlcRebaudioside A and stevioside with improved solubilities
US10357052B2 (en)2014-06-162019-07-23Sweet Green Fields USA LLCRebaudioside A and stevioside with improved solubilities
US10485256B2 (en)2014-06-202019-11-26Sweet Green Fields International Co., LimitedStevia sweetener with improved solubility with a cyclodextrin
JP2018536411A (en)*2015-11-242018-12-13フイルメニツヒ ソシエテ アノニムFirmenich Sa Glucosylated terpene glycoside
JP6997084B2 (en)2015-11-242022-02-03フイルメニツヒ ソシエテ アノニム Glucosylated terpene glycosides
CN114340404A (en)*2019-08-282022-04-12三得利控股株式会社 Steviol glycoside composition and method for producing steviol glycoside composition from dried leaves of Stevia plant
US12279633B2 (en)2019-08-282025-04-22Suntory Holdings LimitedSteviol glycoside composition
WO2023100136A1 (en)*2021-12-012023-06-08Almendra (Thailand) Ltd.Methods and compositions for improved sugar-like taste
CN117106000A (en)*2023-07-172023-11-24华南理工大学 A kind of steviol glycoside aggregate and its preparation method and application
WO2025015739A1 (en)*2023-07-172025-01-23华南理工大学Steviol glycoside aggregate, and preparation method therefor and use thereof

Also Published As

Publication numberPublication date
JP4345961B2 (en)2009-10-14

Similar Documents

PublicationPublication DateTitle
JP4345961B2 (en) Stevia sweetener composition
JP7364246B2 (en) Sweetener compositions and foods containing the same
US8501261B2 (en)High-purity Rebaudioside C and process for purification of the same
CN113710105B (en)Steviol glycoside solubility enhancers
US8299224B2 (en)High-purity Rebaudioside D
CA3015571C (en)High-purity rebaudioside d and applications
AU2011213602B2 (en)Solubility enhanced terpene glycoside(s)
US11950610B2 (en)Glucosyl Rebaudioside C
US20170226145A1 (en)Methods of extraction and purification from stevia rebaudiana of compositions with enhanced rebaudioside-m content, uses of said composition and natural sweetener compositions with said composition
JPH08214A (en)Rebaudioside a-based sweetener and its production
US20140004248A1 (en)Processes of Purifying Steviol Glycosides
JPS6291161A (en) Stevia sweetener and its manufacturing method
CA2857080A1 (en)Sweetener compositions and methods of making same
EP2753189A1 (en)Highly soluble stevia sweetener
US8916138B2 (en)High-purity rebaudioside D and low-calorie tooth paste composition containing the same
JPH02261359A (en) Improved stevia sweetener, method for improving it, and food/drinks or medicines using it
JP7109939B2 (en) High-intensity sweetener composition, sugar alcohol composition, high-intensity sweetener mixed composition, rare sugar composition, food and drink, cosmetics and pharmaceuticals
JP2001161309A (en)Method for imparting sweetness and sweetener
CA3131387A1 (en)Novel mogrosides and uses of the same
JP5532935B2 (en) Stevia sweetener
JP2005269978A (en)Low-odor water-soluble composition
US20220322708A1 (en)Food ingredients from stevia rebaudiana
JPS5848157B2 (en) Complex sweetener containing palatinose
CN115768281A (en) Steviol Glycoside Malonate
Class et al.Patent application title: High-Purity Rebaudioside D Inventors: Varuzhan Abelyan (Kuala Lumpur, MY) Avetik Markosyan (Kuala Lumpur, MY) Lidia Abelyan (Kuala Lumpur, MY) Assignees: PureCircle Sdn Bhd

Legal Events

DateCodeTitleDescription
A621Written request for application examination

Free format text:JAPANESE INTERMEDIATE CODE: A621

Effective date:20060407

A977Report on retrieval

Free format text:JAPANESE INTERMEDIATE CODE: A971007

Effective date:20080125

A131Notification of reasons for refusal

Free format text:JAPANESE INTERMEDIATE CODE: A131

Effective date:20080129

A521Request for written amendment filed

Free format text:JAPANESE INTERMEDIATE CODE: A523

Effective date:20080331

A131Notification of reasons for refusal

Free format text:JAPANESE INTERMEDIATE CODE: A131

Effective date:20080513

A521Request for written amendment filed

Free format text:JAPANESE INTERMEDIATE CODE: A523

Effective date:20080711

RD03Notification of appointment of power of attorney

Free format text:JAPANESE INTERMEDIATE CODE: A7423

Effective date:20080731

RD13Notification of appointment of power of sub attorney

Free format text:JAPANESE INTERMEDIATE CODE: A7433

Effective date:20080820

A072Dismissal of procedure [no reply to invitation to correct request for examination]

Free format text:JAPANESE INTERMEDIATE CODE: A073

Effective date:20081021

A131Notification of reasons for refusal

Free format text:JAPANESE INTERMEDIATE CODE: A131

Effective date:20090407

A521Request for written amendment filed

Free format text:JAPANESE INTERMEDIATE CODE: A523

Effective date:20090605

TRDDDecision of grant or rejection written
A01Written decision to grant a patent or to grant a registration (utility model)

Free format text:JAPANESE INTERMEDIATE CODE: A01

Effective date:20090630

A01Written decision to grant a patent or to grant a registration (utility model)

Free format text:JAPANESE INTERMEDIATE CODE: A01

A61First payment of annual fees (during grant procedure)

Free format text:JAPANESE INTERMEDIATE CODE: A61

Effective date:20090709

R150Certificate of patent or registration of utility model

Ref document number:4345961

Country of ref document:JP

Free format text:JAPANESE INTERMEDIATE CODE: R150

Free format text:JAPANESE INTERMEDIATE CODE: R150

FPAYRenewal fee payment (event date is renewal date of database)

Free format text:PAYMENT UNTIL: 20120724

Year of fee payment:3

FPAYRenewal fee payment (event date is renewal date of database)

Free format text:PAYMENT UNTIL: 20130724

Year of fee payment:4

R250Receipt of annual fees

Free format text:JAPANESE INTERMEDIATE CODE: R250

R250Receipt of annual fees

Free format text:JAPANESE INTERMEDIATE CODE: R250

R250Receipt of annual fees

Free format text:JAPANESE INTERMEDIATE CODE: R250

R250Receipt of annual fees

Free format text:JAPANESE INTERMEDIATE CODE: R250

R250Receipt of annual fees

Free format text:JAPANESE INTERMEDIATE CODE: R250

R250Receipt of annual fees

Free format text:JAPANESE INTERMEDIATE CODE: R250

R250Receipt of annual fees

Free format text:JAPANESE INTERMEDIATE CODE: R250

R250Receipt of annual fees

Free format text:JAPANESE INTERMEDIATE CODE: R250

R250Receipt of annual fees

Free format text:JAPANESE INTERMEDIATE CODE: R250

R250Receipt of annual fees

Free format text:JAPANESE INTERMEDIATE CODE: R250

R250Receipt of annual fees

Free format text:JAPANESE INTERMEDIATE CODE: R250

EXPYCancellation because of completion of term

[8]ページ先頭

©2009-2025 Movatter.jp