JPS5828245A - Preparation of sweetening agent - Google Patents

Abstract

PURPOSE:To prepare a sweetening agent, by purifying an extract obtained from Rubus chingii Hu with a high polymeric synthetic adsorbent resin of the giant network structure, ion exchange resin and an adsorbent resin containing an acrylic ester. CONSTITUTION:Components extracted from the leaf and stem of Rubus chingii Hu is brought into contact with a high polymeric adsorbent resin having the giant network structure to adsorb the active constituents on the resin 4-8pH. The adsorbed constituents are then washed with water and desorbed with a hydrophilic organic solvent, e.g. alcohol. The desorbed constituents are desalted and decolored with an anion exchange resin and a cation exchange resin. The resultant aqueous solution containing 2-20% active constituents is reacted with a synthetic high polymeric adsorbent resin, having the giant network structure, and containing an acrylic ester as a base material to remove components of bitter taste and odors and give the aimed sweetening agent of high purity.

Description

[Detailed description of the invention]

The present invention relates to snowfield tea (Rubus chingii Hu
This invention relates to a method for producing a natural sweetener from the stems and leaves of . Xueyuan tea (also called sugar beet), which is grown in Guangliang province of the People's Republic of China, is a perennial warm-water plant in the Rosaceae family that is closely related to the Japanese strawberry. The stems and leaves of this plant, mainly the leaves, have a sweetness that is relatively similar to that of sucrose, and the Jinxiuzui tribe has long used it as a substitute for tea and also eaten it as a sake paste. Regarding the sweet component of Yukihara tea, there has already been research conducted by Nichi et al. at Hiroshima University, and it has been confirmed that it is a diterpene glycoside with the following structure, and it has been named Rubusosi-de. However, the water, hot water, or hydroalcoholic extract of Yukihara tea contains many biological components other than sweet components, so it has a bitter or astringent taste, and also has a unique KK odor such as a chlorophyll odor. Therefore, if the above-mentioned Yukihara tea extract is added directly as a sweetener to foods, medicines, etc., it will impair the flavor and give off an unpleasant or off-flavor, which will limit its use. Therefore, the present inventors conducted repeated research to remove impurities other than the sweetness C Peng OH υH possessed by the Yukihara tea extract. As a result, the present inventors applied the sweet component-containing water extracted from the Yukihara tea to a synthetic polymer adsorption resin with a giant network structure. After adsorbing the sweet component by contacting with an acid solution, it is desorbed with a hydrophilic organic solvent such as hydroalcohol, and the solvent of the desorption solution is distilled off, followed by ion exchange and decolorization using a cation exchange resin. By contacting an aqueous solution that does not contain acrylic acid ester with a synthetic polymer adsorption resin that has a giant network structure based on acrylic acid ester, the bitterness, astringency, and odor components that are extracted from the original plant at the same time as sweet components are adsorbed and removed. We have completed a method for producing a natural sweetener that does not affect flavor even when added to foods, medicines, etc. The present invention will be further explained below. When Yukihara tea extract is extracted with cold water, hot water, or hydrous alcohol, the alcohol is distilled off to form an aqueous solution, and then it is brought into contact with a synthetic polymer adsorption resin having a large network structure.

[Selective adsorption of sweet ingredients to resin. In this case, a pH of 4 to 8 is suitable for the liquid to be treated. On the alkaline side, where p)I exceeds 8, the ability of the resin to adsorb sweet components is significantly reduced, while on the acidic side, where pH is less than 4, there is a risk that precipitates may be formed or the sweet components may be decomposed. As the resin used at this time, the following resins can be used, regardless of whether they are polar or non-polar. Amberlite XAI)-2, Amberlite XAD-7 (manufactured by Rohm and Haas), Diamond, Ion HP-20, Amberlite
-30 (manufactured by Mitsubishi Kasei Corporation), Castel 8-xtz
, same S-221C Montegi//manufactured by), Revachit OC
-103 (manufactured by Bayer). To contact the aqueous extract solution with the resin, it is stirred batchwise or passed through a column of adsorption resin at S■=about 0.5 to 6. As a pretreatment for adsorption resin purification, (1) polyacrylamide-based cationic polymer flocculants, AI compound-based, Ca
(2) A method of coagulating and precipitating treatment with a known inorganic flocculant such as a compound type, (2) A method of removing pigments, etc. with Diaion WA-go, Go's high porous type strong/weak basic ion exchange resin, ( 3) If preliminary purification is performed, such as by liquid-liquid countercurrent extraction with an alcohol having 4 to 7 carbon atoms and incompatible with water, the sweetening component is transferred to the alcohol layer, and the adsorption resin is Increasing the adsorption amount of sweet ingredients, ff
M can be performed even more sophisticatedly. The resin that has adsorbed the sweet component is washed with water in an amount of 1 to 5 times the amount of the resin, and then the sweet component is desorbed using a hydrophilic organic solvent containing water such as alcohol in an amount of 2 to 10 times the amount of the resin. Hydrophilic organic solvents that can be used at this time include lower alcohols such as methanol, ethanol, and globanol, dioxane, and acetone. The minimum concentration of solvent required for desorption varies depending on the solvent used, but desorption will be incomplete unless it is 60% or more for methanol and +0% or more for ethanol. Desorption liquids containing sweet components have significantly improved color, odor, and taste. However, since a brown potassium odor still remains, further purification is performed using an ion exchange resin and a cation exchange resin. That is, the solvent of the liquid containing the desorbed sweet component is distilled and recovered, and a strongly acidic cation exchange resin in the H-form and an OH-
Desalting and decolorizing are performed using a shaped medium/weakly basic anion exchange resin. Thereby, a light yellow Yukihara tea sweetener can be obtained. The ion exchange resin used is preferably a highly porous resin that can efficiently decolorize and desalt. To give specific examples, strong acidic cation exchange resins include Diaion PK series (manufactured by Mitsubishi Kasei Corporation),
C-z5D, C-3 (manufactured by Diamond Jam Rock Chemical Co., Ltd.), Amberlite 1B-200
C (manufactured by 0-Muanthaas), Rebachit) SP-11
2 (manufactured by Bayer), DOWEX MSC-1 (manufactured by Dow Chemikabe), and weakly basic ion exchange resins include DIAION WA-30 (Mitsubishi Kasei Corporation) MP- 62, MP-64 (manufactured by Bayer), Deolide A-561 (manufactured by Diamond Jam Rock Chemical), Amberlite IRA-9
3. There are similar products such as Komu-94 (manufactured by Rohm and Haas). The amount of anion and cation exchange resin used is x kg of Yukihara tea as raw material.
About 500~t, oooNt each is enough for **
You can increase the effect. However, if preliminary purification as described above is carried out before treatment with the adsorption resin, 1 of each of the above amounts can be obtained.
The amount used can be reduced by 1/3 to 1/2. Although the power tea extract purified as described above has a sweetness component content of 6096 or more, it still has bitterness, astringency, and a unique odor. spoils the flavor. Therefore, fw product output 2 treated with ion exchange resin
When made into a 20-membered aqueous solution and brought into contact with a synthetic polymer adsorption resin having a giant network structure based on acrylic acid ester, bitter, astringent, and odor components can be adsorbed and removed without adsorbing sweet components. The essential conditions at this time are
(The aqueous solution to be treated with IJ is sufficiently desalted, and (2) the adsorption resin is Amberlite XAD-7, Amberlite XAD-7,
D-s (manufactured by Rohm & Co., Ltd.), Castel 8-
221, 8-223 (It is a synthetic polymer adsorption resin having a giant network structure based on an acrylic ester such as Montegison Il!ri). Condition (1) is shown in Table 1. Tayo R, ubuso
This is because when the side salt-containing aqueous solution is brought into contact with the above-mentioned resin, not only impurities but also sweet components are adsorbed. In addition, adsorption resins that do not have acrylic acid ester as a matrix cannot be used for purification at this stage because they adsorb sweet components from both salt solutions and desalted solutions. Rubu when contacted with Annoku-Lite XAD-8 by column method
so side @ deposition amount (experimental conditions) A column was filled with 200 d of XAD-8 resin, and the above-mentioned liquids were passed through each column at 8V=2. The amount of solution passed is Ru
It is about 50g 8 parts as busoside. Rubu
Quantification of soside was carried out by gas chromatography after acid decomposition and methylation. The present invention will be explained below with reference to Examples. Example 1 One cup of Yukihara tea was stirred and extracted with 10 times the amount of warm water (60° C.) for 2 hours, and the extract was separated by a decanting method. 10 times the amount of hot water was added to the residue and extracted in the same manner, and combined with the previous extract to obtain an extract of xr, 41. 268g for extract
solids, including 49.2 g f)
It was confirmed by gas chromatographic analysis that no rubusoside was contained. The pH 5.9 extract was passed through a 200 Mepsier sieve to remove suspended matter, and then passed through a 1,000-diaion HP
- Pass the liquid through the 20-person column at 5V=1, and
ide was adsorbed. After washing the column with 3 times the amount of water, flow 5 times the amount of 60-1 ethanol at 5 V = t to R.
I removed the ubusoside. Rubuso-sid
The recovery rate of e was 99%, and the recovery rate of D Rubus
The content of o -5ide was 44s. After removing the solvent by distilling the desorption solution containing this Rubu-5oside under reduced pressure, Duolite C-25D was
Demineralization and decolorization were carried out by sequentially passing 5,001 liters of Amberlite IRA-94 into columns at SV=1. The obtained desalinated solution (Amberley) XAD-sa
oo* was poured into the column at 5V=4, and water 6001
After pouring No. 11 and combining the extruded unadsorbed parts, all the unadsorbed parts were concentrated to dryness under reduced pressure to obtain 74 g of purified Yukihara tea sweetener. The purified product has a Ru-busoside content of 63%, and contains Ru-busoside from the power tea extract.
The recovery rate was 95%. Example 2 Extracts 17.17 were obtained from Yukiharacha 1 and 9 by the same extraction procedure as in Example 1. In the extract, 49.6 g of Rubusoside was confirmed by gas chromatograph 2 filter analysis. The cationic polymer flocculant Catfloc (
(manufactured by Carbon, USA) was added to give iooppm, and coagulation and precipitation of colloidal impurities and the like was carried out. Amberlite
Pass liquid through AD-2 (5ooy) at 5V=1, and
OS ide was adsorbed. After washing the 2 mm with 3 times the amount of water and desorbing the albusoside with 60% ethanol.
IRA-94 (28oMl) 0) 8V = 1 for each column
Desalting and decolorization were performed by passing liquid through the solution. This desalinated solution was mixed with Castel 8-221 adsorption resin 2001.
The liquid was passed through a column filled with water at 5V=a, and then 400
1 with water, and all unadsorbed parts were concentrated under reduced pressure to dryness. The Rubusoside content of the obtained sweetener was 72
The recovery rate of R+ubusoside was 92%. Example 3 The purified product sog obtained in Example 2 was dissolved in 99% methanol 175-, and 25 ml of water was added, and the mixture was left at 5°C for 3 days.
21 g of Rubusoside crystals were obtained. The above Rubusoside crystals, the purified product from Example IK, the Yukihara tea extract, and the ion-exchange decolorized product were subjected to a sensory test regarding K odor and interest by a panel of 14 people, and the results are shown in Table 2. In addition, the test was conducted using 0.08% of each Rubusoside.
Containing aqueous solutions and coffee. Table-2 Procedural Amendment 4″1 Mr. Hiroki Shimada, Commissioner of the License Agency] Indication of middle 1’1 Showa 56-1 Patent Application No. 1230111 3 Relationship with person making the amendment 11 Patent applicant +i, lli Name (?, M=) Kyuso Kasei Co., Ltd. 4, Agent (1 location, 5th floor, 7th floor, Kyodo Building, $-1-18 Kita-Aoyama, Minato-ku, Tokyo)
Date of amendment order Vol. 6 Number of inventions increased by amendment (2) "Unique KJ" on page 2, line 15 is amended to read "unique." (3) "Polymer synthesis" in lines 2 and 8 of page 4 is corrected to "synthetic polymer." (4) Add "," between "let me contact" and "original plant" on page 4, line 9. (5) On page 5, lines 14-15, "Flow at S■ = about 0.5 to 6." is corrected to "Flow at SV (space velocity) about 0.5 to 6 per hour." (6) Page 6, line 9, page 11, line 1, and page 12, line 7
Correct "Washing" in the row to "Washing". (7) Add K "," between "when brought into contact" and "sweet ingredient" on page 8, line 18. (8) Delete "-" from "60%-" in the first line of page 11. (9) Claims characterized by “-” in “99%-” at the end of page 12 Sweet ingredients are extracted from Yukihara tea, and an aqueous solution of the obtained extract is By contacting the molecular adsorption resin K, the Yukihara tea sweet component is transferred to the above adsorption resin KWk.
After this, the aqueous solution containing the desorbed sweet component is treated with a cation exchange resin to demineralize and decolorize the solution, which is then desorbed using a hydrophilic organic solvent in a water-containing state. A method for producing a Yukihara tea natural sweetener, which comprises adsorbing and removing residual impurities by bringing it into contact with a synthetic polymer adsorption resin.

Claims (1)

[Claims] Sweet ingredients are extracted from Yukihara tea, and the aqueous solution of the obtained extract is brought into contact with a synthetic polymer adsorption resin having a giant network structure. The aqueous solution containing the desorbed sweet component is treated with an anion exchange resin.The desalted and decolorized solution is contacted with a synthetic molecular adsorption resin containing acrylic ester as a matrix. A method for producing a natural sweetener from Yukihara tea, characterized by adsorbing and removing residual impurities.