CN105646616A - Stevia glucoside B crystal form G as well as preparation method, food composition and application thereof - Google Patents
Stevia glucoside B crystal form G as well as preparation method, food composition and application thereof Download PDFInfo
- Publication number
- CN105646616A CN105646616A CN201610173788.5A CN201610173788A CN105646616A CN 105646616 A CN105646616 A CN 105646616A CN 201610173788 A CN201610173788 A CN 201610173788A CN 105646616 A CN105646616 A CN 105646616A
- Authority
- CN
- China
- Prior art keywords
- stevioside
- crystal formation
- glycosides
- preparation
- crystal form
- 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
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/24—Condensed ring systems having three or more rings
- C07H15/256—Polyterpene radicals
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
- A23L2/52—Adding ingredients
- A23L2/60—Sweeteners
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Nutrition Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Saccharide Compounds (AREA)
Abstract
The invention belongs to the technical field of sweeteners, and in particular relates to a stevia glucoside B crystal form G as well as a preparation method, a food composition and the application thereof. The stevia glucoside B crystal form G is measured by a Cu-Ka ray, so that X-ray powder diffraction analysis is obtained; a 2 theta valve expressed in degrees at least has obvious characteristic diffraction peaks at 3.93, 13.45, 16.62, 18.33, 19.90, 23.95 and 28.02. After solid chemical analysis methods such as XRPD, DSC, TGA, DVS and the like are used for carrying out comprehensive characterization on the crystal form G, the crystal form G is found to have the advantages of being high in degree of crystallinity, good in stability and water solubility, low in moisture property and the like, thus being suitable for wider application fields. The preparation method is simple, easy to operate, more in selectivity and good in reproducibility, and can be used for stably obtaining the target crystal form.
Description
Technical field
The invention belongs to sweeting agent technical field, particularly relate to a kind of stevioside B glycosides crystal formation G, its preparation method, food compositions and application.
Background technology
Folium Stevlae Rebaudianae is a kind of little feverfew, originates in South America Paraguay and visits mountain range with Oman that Brazil borders on. It has been determined that Folium Stevlae Rebaudianae sweet ingredient have 9 kinds: stevioside, steviolbioside, stevioside A glycosides-stevioside F glycosides and Du Ke glycosides G. They all belong to glycosides compound, have identical aglycon steviol (steviol); Differ only in and glycosidic bond combines the kind of sugar, quantity and configuration. Because they are all with pleasantly sweet glycosides compound, it is referred to as stevioside (SteviolGlycosides). Wherein, stevioside B glycosides is the stevioside compounds that a kind of sugariness is about sucrose 150 times. Stevioside B glycosides (RebGudiosideB, RB), its structural formula is as follows:
In Stevia rebaudiana (Bertoni) Hemsl extract, stevioside G glycosides has been widely used in beverage, food and health product as sweeting agent. But, stevioside G glycosides is with natural slight bitterness or herbaceous taste, and prior art also cannot completely be removed or cover, and this makes drink and food industry also dare not simply substitute white sugar easily completely with stevioside. Research in magazine " JournGlofGgriculturGlGndFoodChemistry " one section " HumGnPsychometricGndTGsteReceptorResponsestoSteviolGlyco sides " by name shows, stevioside B glycosides is relative to stevioside G glycosides, its sugariness is similar, but bitterness outline is weak. So, stevioside B glycosides has the mouthfeel being better than stevioside G glycosides, and can use as sweeting agent. Patent CN104602543G reports the stevioside B glycosides compositions with other sugar in food and beverage application. Owing to the content in Folium Chrysanthemi is relatively low, so the preparation method of stevioside B glycosides obtains mainly by sodium hydroxide hydrolysis stevioside G glycosides at present. The water solublity of stevioside B glycosides is extremely low at ambient temperature, uses thus limiting it.
There were significant differences in dissolubility, dissolution rate, fusing point, outward appearance and biological effectiveness etc. for the different crystal forms of same compound, thus affecting its stability and bioavailability. The research of polymorph in pharmaceuticals phenomenon has become as pharmaceutical technology and front requisite pith determined by new drug preparation. For stevioside B glycosides, to its carry out polymorphic research also it is critical that.Patent US20130267693G1 reports stevioside B glycosides crystal formation 1, crystal formation 2, crystal formation 3, crystal formation 4 and preparation method thereof. But from X-ray powder diffraction and polarisation photo, these four kinds of crystal formation degree of crystallinity differences also contain part amorphous. For bibulous glucoside compound, amorphous may result in product is storing and moisture absorption caking conglomeration in transportation. Meanwhile, these four kinds of crystal formations do not improve the water solublity of stevioside B glycosides.
This area is in the urgent need to providing a kind of better crystal formation of performance, for instance degree of crystallinity height, good water solubility, hygroscopicity is little, stability is high novel crystal forms. Meanwhile, in the urgent need to providing preparation method and the purposes of above-mentioned crystal formation.
Summary of the invention
An object of the present invention is in that: provide the stevioside B glycosides crystal formation G that a kind of degree of crystallinity height, good water solubility, stability are high, hygroscopicity is little.
For solving above-mentioned technical problem, the technical scheme is that
Stevioside B glycosides crystal formation G, described crystal formation G use the X-ray powder diffraction analysis that Cu-K alpha ray records, and at least have obvious characteristic diffraction peak at 3.93,13.45,16.62,18.33,19.90,23.95 and 28.02 places with the 2 �� angles that degree represents.
Improving as one, described crystal formation G uses the X-ray powder diffraction analysis that obtains of Cu-K alpha ray measurements, with spend represent 2 �� values, range of error for �� 1 ��, withThe relative intensity of the interplanar distance d represented and the diffraction maximum being expressed as a percentage has the feature that
| 2�� | d | Relative intensity % |
| 3.93 | 22.44 | 100.0 |
| 7.88 | 11.22 | 5.6 |
| 9.05 | 9.76 | 4.9 |
| 9.25 | 9.55 | 5.0 |
| 10.83 | 8.16 | 5.3 |
| 12.02 | 7.36 | 3.5 |
| 13.45 | 6.58 | 23.8 |
| 13.81 | 6.41 | 4.8 |
| 14.36 | 6.16 | 3.8 |
| 14.98 | 5.91 | 6.0 |
| 16.31 | 5.43 | 4.2 |
| 16.62 | 5.33 | 21.4 |
| 17.38 | 5.10 | 5.4 |
| 18.33 | 4.84 | 23.7 |
| 18.62 | 4.76 | 4.9 |
| 19.90 | 4.46 | 22.7 |
| 20.11 | 4.41 | 9.4 |
| 22.94 | 3.87 | 7.4 2 --> |
| 23.95 | 3.71 | 12.8 |
| 24.32 | 3.66 | 4.2 |
| 27.56 | 3.23 | 5.4 |
| 28.02 | 3.18 | 13.8 |
��
Improving as one, the differential scanning calorimetric analysis of described crystal formation G has obvious endothermic peak 60-140 DEG C, 150-180 DEG C and 200-240 DEG C.
Improving as one, the thermogravimetic analysis (TGA) of described crystal formation G starts to decompose at 270 �� 10 DEG C.
Improve as one, described crystal formation G has dynamic water absorption (DVS) collection of illustrative plates as shown in Figure 4, it is within the scope of 0-45% at relative humidity, it absorbs the mass percent of moisture at 0-2.5%, it is within the scope of 45-55% at relative humidity, it absorbs the mass percent of moisture at 2.5-5.1%, and at relative humidity more than 55%, its mass percent fluctuation range absorbing moisture is less.
Improving as one, described crystal formation G has shape characteristic as shown in Figure 5.
The two of the purpose of the present invention are in that: provide that a kind of technique is simple, easily operated, stability is high and the preparation method of the stevioside B glycosides crystal formation G of good fluidity.
For solving above-mentioned technical problem, the technical scheme is that
The preparation method of stevioside B glycosides crystal formation G, described preparation method comprises the following steps:
(1) suspendible: in 0-100 DEG C of temperature range, by stevioside B glycosides and solvent mixing 0.1-48h, obtains suspension solution;
(2) filter: in 0-100 DEG C of temperature range, suspension solution is filtered or centrifugal, obtain white solid, obtain stevioside B glycosides crystal formation G;
(3) cooling: step (2) filtration or the settled solution after centrifugal, is cooled to 0-50 DEG C, precipitates out white solid, filter, obtain stevioside B glycosides crystal formation G;
(4) volatilization: step (2) filtration or the settled solution after centrifugal, is placed in 0-100 DEG C of temperature range and volatilizees, precipitate out white solid, obtain stevioside B glycosides crystal formation G.
Improving as one, in step (1), the dry purity of described stevioside B glycosides is 50-100%.
Improving as one, described solvent is one or more in water, methanol, ethanol, 1-propanol, 2-propanol, 3-methyl-1-butanol, 2-methyl isophthalic acid-propanol, acetonitrile, acetone, butanone, methylisobutylketone, methyl acetate, Ethyl formate, ethyl acetate, butyl acetate, propyl acetate, isopropyl acetate, isobutyl acetate or three fourth MEEs.
The three of the purpose of the present invention are in that: provide a kind of food compositions containing described stevioside B glycosides crystal formation G.
The four of the purpose of the present invention are in that: provide the described stevioside B glycosides crystal formation G and preparation method thereof application in food, beverage and medicine.
Owing to have employed technique scheme, the invention has the beneficial effects as follows:
The preparation method of stevioside B glycosides crystal formation G provided by the invention, its technique is simple, easily operated, can prepare stevioside B glycosides crystal formation G by multiple method, and the product degree of crystallinity prepared is high, hygroscopicity is low, stability is high, good water solubility.
Accompanying drawing explanation
Fig. 1 is X-ray powder diffraction (XRPD) figure of stevioside B glycosides crystal formation G provided by the invention;
Fig. 2 is differential scanning calorimetric analysis (DSC) figure of stevioside B glycosides crystal formation G provided by the invention;
Fig. 3 is thermogravimetic analysis (TGA) (TG) figure of stevioside B glycosides crystal formation G provided by the invention;
Fig. 4 is dynamic water absorption (DVS) figure of stevioside B glycosides crystal formation G provided by the invention;
Fig. 5 is the polarisation photo of stevioside B glycosides crystal formation G provided by the invention;
Fig. 6 be stevioside B glycosides crystal formation G provided by the invention before it is dried after X-ray powder diffraction (XRPD) comparison diagram;
Fig. 7 be stevioside B glycosides crystal formation G provided by the invention 40 DEG C, humidity 75% when store X-ray powder diffraction (XRPD) comparison diagram of half a year;
Fig. 8 be stevioside B glycosides crystal formation G provided by the invention 40 DEG C, humidity 75% when store efficient liquid phase (HPLC) comparison diagram of half a year.
Detailed description of the invention
In order to make the purpose of the present invention, technical scheme and advantage clearly understand, below in conjunction with drawings and Examples, the present invention is further elaborated. Should be appreciated that specific embodiment described herein is only in order to explain the present invention, is not intended to limit the present invention.
Embodiment one
At ambient temperature, the stevioside B glycosides that 20g material purity is 100% is added in 100mL methanol, after stirring 12h, filter, obtain filtrate and white solid, filtrate and white solid vacuum drying at 25 DEG C, all obtain stevioside B glycosides crystal formation G.
Embodiment two
Under 50 DEG C of conditions, the stevioside B glycosides that 20g material purity is 100% is added in 100mL methanol, after stirring 12h, filter, obtain filtrate and white solid, filtrate and white solid vacuum drying at 25 DEG C, all obtain stevioside B glycosides crystal formation G.
Embodiment three
At ambient temperature, the stevioside B glycosides that 40g material purity is 50% is added in 100mL methanol, after stirring 12h, be filtrated to get filtrate and white solid, filtrate and white solid vacuum drying at 25 DEG C, all obtain stevioside B glycosides crystal formation G.
Embodiment four
At ambient temperature, the stevioside B glycosides that 20g material purity is 100% is added in methanol-water (v/v) system of 70mL30%, after stirring 12h, filter, obtain filtrate and white solid, filtrate and white solid vacuum drying at 25 DEG C, all obtain stevioside B glycosides crystal formation G.
Embodiment five
At ambient temperature, the stevioside B glycosides that 20g material purity is 100% is added in methanol-water (v/v) system of 50mL50%, after stirring 12h, filter, obtain filtrate and white solid, filtrate and white solid vacuum drying at 25 DEG C, all obtain stevioside B glycosides crystal formation G.
Embodiment six
At ambient temperature, the stevioside B glycosides that 20g material purity is 100% is added in alcohol-water (v/v) system of 50mL50%, after stirring 12h, filter, obtain filtrate and white solid, filtrate and white solid vacuum drying at 25 DEG C, all obtain stevioside B glycosides crystal formation G.
Embodiment seven
At ambient temperature, the stevioside B glycosides that 20g material purity is 100% is added in alcohol-water (v/v) system of 50mL50%, after stirring 48h, filter, obtain filtrate and white solid, filtrate and white solid vacuum drying at 25 DEG C, all obtain stevioside B glycosides crystal formation G.
Embodiment eight
At ambient temperature, the stevioside B glycosides that 20g material purity is 100% is added in alcohol-water (v/v) system of 50mL50%, after stirring 48h, filter, obtain filtrate and white solid, filtrate and white solid vacuum drying at 50 DEG C, all obtain stevioside B glycosides crystal formation G.
Embodiment nine
At ambient temperature, the stevioside B glycosides that 20g material purity is 100% is added in alcohol-water (v/v) system of 200mL50%, after stirring 48h, the filtrate being filtrated to get is quickly cooled to 5 DEG C, precipitates out a large amount of crystal, filters, crystal dries, and obtains stevioside B glycosides crystal formation G.
Embodiment ten
Under 90 DEG C of conditions, the stevioside B glycosides that 20g material purity is 100% is added in alcohol-water (v/v) system of 100mL50%, after stirring 48h, the filtrate being filtrated to get is quickly cooled to room temperature, precipitates out a large amount of crystal, filters, crystal dries, and obtains stevioside B glycosides crystal formation G.
Embodiment 11
Under 90 DEG C of conditions, the stevioside B glycosides that 20g material purity is 100% is added in alcohol-water (v/v) system of 100mL50%, after stirring 48h, the filtrate being filtrated to get is cooled to room temperature with the rate of temperature fall of 1 DEG C/h, precipitate out a large amount of crystal, filtering, crystal dries, and obtains stevioside B glycosides crystal formation G.
Embodiment 12
Under 90 DEG C of conditions, the stevioside B glycosides that 20g material purity is 100% is added in alcohol-water (v/v) system of 100mL50%, after stirring 48h, the filtrate being filtrated to get is cooled to room temperature with the rate of temperature fall of 10 DEG C/h, and stand 2h at ambient temperature, precipitate out a large amount of crystal, filter, crystal dries, and obtains stevioside B glycosides crystal formation G.
Embodiment 13
Under 90 DEG C of conditions, the stevioside B glycosides that 20g material purity is 100% is added in alcohol-water (v/v) system of 100mL50%, after stirring 48h, the filtrate being filtrated to get is uncovered volatilization naturally at ambient temperature, wait to precipitate out a large amount of crystal, filtering, crystal dries, and obtains stevioside B glycosides crystal formation G.
Embodiment 14
Under 90 DEG C of conditions, the stevioside B glycosides that 20g material purity is 100% is added in alcohol-water (v/v) system of 100mL50%, after stirring 48h, the filtrate being filtrated to get is volatilized when room temperature, nitrogen flow are 25mL/min, wait to precipitate out a large amount of crystal, filtering, crystal dries, and obtains stevioside B glycosides crystal formation G.
Embodiment 15
Under 90 DEG C of conditions, the stevioside B glycosides that 20g material purity is 100% is added in alcohol-water (v/v) system of 100mL50%, after stirring 48h, the filtrate being filtrated to get is volatilized when room temperature, vacuum are 0.05MPa, wait to precipitate out a large amount of crystal, filtering, crystal dries, and obtains stevioside B glycosides crystal formation G.
Embodiment 16
Under 90 DEG C of conditions, the stevioside B glycosides that 20g material purity is 100% is added in alcohol-water (v/v) system of 100mL50%, after stirring 48h, the filtrate being filtrated to get is volatilized when room temperature, vacuum are 0.05MPa, wait to precipitate out a large amount of crystal, filtering, crystal dries, and obtains stevioside B glycosides crystal formation G.
Embodiment 17
Under 0 DEG C of condition, the stevioside B glycosides that 20g material purity is 100% is added in 100mL methanol, after stirring 48h, filter, obtain filtrate and white solid, filtrate and white solid vacuum drying at 25 DEG C, all obtain stevioside B glycosides crystal formation G.
Embodiment 18
Under 100 DEG C of conditions, the stevioside B glycosides that 20g material purity is 100% is added in alcohol-water (v/v) system of 50mL50%, after stirring 0.1h, filter, obtain filtrate and white solid, filtrate and white solid vacuum drying at 25 DEG C, all obtain stevioside B glycosides crystal formation G.
The stevioside B glycosides sodium salt crystal formation G that above-described embodiment is prepared carries out X-ray powder diffraction analysis (XRPD), differential scanning calorimetric analysis (DSC), thermogravimetic analysis (TGA) (TG), dynamic water adsorption analysis (DVS) etc.
XRPD analyzes: it adopts the diffractometer of Brooker Instrument Ltd. of Germany BrukerD8GdvGnce type to detect in room temperature, adopts Cu K alpha ray2 �� angle sweeps are from 3 degree to 40 degree, and scanning speed is 0.2 degrees second. Its analysis result is shown in that the stevioside B glycosides crystal formation G that Fig. 1, XRPD spectrogram shows that above-described embodiment prepares has good degree of crystallinity.
In sample powder X-ray powder diffraction, specific crystal formation the diffraction spectrogram obtained is distinctive often. Because the difference of the relative amount of crystallization condition, particle diameter, mixture and other test condition, diffraction spectrogram may produce preferred orientation effect, thus causing that in spectrogram, the relative intensity of some bands of a spectrum (particularly in low angle) changes. Therefore, targeted crystal is not distinctive by the relative intensity of diffraction maximum, it may be judged whether time identical with known crystal formation, should be noted that the position at peak rather than their relative intensity. It addition, judge it should be noted that keep organic conception when whether crystal formation is the same, because being not that a diffracted ray represents a thing phase, but a set of specific " d-I/I1 " data just represent a certain thing phase. Should be noted also that in the qualification of mixture, owing under content, degradation factor can cause the disappearance of part diffracted ray, now, it is not necessary to rely on the whole bands of a spectrum observed in high-purity sample, even bands of a spectrum are likely to given crystal is distinctive.
Dsc analysis: it adopts the DSC8500 type differential scanning calorimeter of platinum Elmer Co., Ltd of the U.S. to detect, and atmosphere is nitrogen, and firing rate is 10 degrees celsius/minute. It is analyzed result and sees Fig. 2.
TG analyzes: it adopts the NetzschTG209F3 type thermogravimetric analyzer detection of Nai Chi company of Germany, temperature range: 30-400 DEG C, sweep speed: 10K/min, purges gas: 25mL/min. It is analyzed result and sees Fig. 3.
DVS analyzes: it adopts Britain SMS instrument company DVSIntrinsic type dynamic water adsorption instrument to be measured, and measures temperature: 25 DEG C; Relative humidity: 0-95%. It is analyzed result and sees Fig. 4.
Polarisation photo: it adopts the XPV-400E polarizing microscope of the rectangular optical instrument company limited in Shanghai to test, tests amplification: 5 times. It is analyzed result and sees Fig. 5. Polarisation photo shows, the stevioside B glycosides crystal formation G that above-described embodiment prepares is diamond pattern crystal, has good shape characteristic.
The stevioside B glycosides crystal formation G that above-described embodiment is prepared, carries out XRPD analysis after the drying, and it is analyzed result and sees Fig. 6. As can be seen from Figure 6 its crystal formation is constant, and stability of crystal form is good.
To above-described embodiment prepare stevioside B glycosides crystal formation G, 40 DEG C, RH75% when store half a year, its analyze result see Fig. 7. As can be seen from Figure 7 its crystal formation is constant, illustrates that this crystal formation physical stability under conditions of high humidity is good.
HPLC analyzes: it adopts the 1260infinity hplc determination of Anjelen Sci. & Tech. Inc of the U.S..Sample solution compound method: accurate weighing 25-50 milligram stevioside B glycosides crystal formation G sample, puts in the volumetric flask of 25 milliliters, is subsequently adding water-acetonitrile (7:3, v/v) solution, carry out dissolving and being settled to scale. The collocation method of sodium phosphate buffer (specification: 10mmol/L, pH value: 2.6): be dissolved in 2 liters of water by 2.76 grams of sodium dihydrogen phosphate, adds phosphoric acid, pH value is adjusted to 2.6. Chromatographic column: LunG5 �� C18 (2) the 100A type chromatographic column of Phenomenex company. Sample size: 5 �� l. Flow velocity: 1.0mL/min. Column temperature: 40 DEG C. Detector: 210nm ultraviolet detection. Mobile phase: the ratio of acetonitrile and sodium phosphate buffer (specification: 10mmol/L, pH value: 2.6) is 32:68. Analyze result and see Fig. 8, above-described embodiment prepare stevioside B glycosides crystal formation G, the chemical stability having had, HPLC analyze be shown in 40 DEG C, RH75% when storage half a year after, its purity, still up to 98.3%, illustrates that this crystal formation chemical stability under conditions of high humidity is good.
The stevioside B glycosides crystal formation G that above-described embodiment prepares, has good repeatability. And water solublity is high and stable, is about 0.5mg/mL, hence it is evident that higher than the crystal formation 1-4 of report in US20130267693A1. It analyzes result such as table 1 below:
Table 1
| Sample ID | Equilbrium solubility (mg/mL) in water |
| Embodiment 1 stevioside B glycosides crystal formation G | 0.452 |
| Crystal formation 1 in US 20130267693A1 | 0.291 |
| Crystal formation 2 in US 20130267693A1 | 0.205 |
| Crystal formation 3 in US 20130267693A1 | 0.160 |
| Crystal formation 4 in US 20130267693A1 | 0.097 |
The stevioside B glycosides crystal formation G that above-described embodiment is prepared, slightly hygroscopicity under customary storage conditions (45-80%RH). The hygroscopicity of stevioside B glycosides crystal formation G is significantly lower than the crystal formation 1-4 of report in US20130267693A1, and not easily moisture absorption is lumpd. Analyze result such as table 2 below:
Table 2
Stevioside B glycosides raw material used in above-described embodiment is provided by Hao Tian pharmaceutcal corporation, Ltd of Zhucheng.
Stevioside B glycosides crystal formation G provided by the invention can be applied in food, beverage and medicine as sweeting agent.
The preparation method of stevioside B glycosides crystal formation G provided by the invention can be applicable in the preparation technology of food, beverage and medicine.
The foregoing is only presently preferred embodiments of the present invention, not in order to limit the present invention, all any amendment, equivalent replacement and improvement etc. made within the spirit and principles in the present invention, should be included within protection scope of the present invention.
Claims (8)
1. stevioside B glycosides crystal formation G, it is characterised in that described crystal formation G uses the X-ray powder diffraction analysis that Cu-K alpha ray records, to spend the 2 �� angles represented at least 3.93,13.45,16.62,18.33, there is obvious characteristic diffraction peak at 19.90,23.95 and 28.02 places.
2. stevioside B glycosides crystal formation G as claimed in claim 1, it is characterised in that described crystal formation G uses the X-ray powder diffraction analysis that Cu-K alpha ray measurements obtains, with spend represent 2 �� values, range of error for �� 1 ��, withThe relative intensity of the interplanar distance d represented and the diffraction maximum being expressed as a percentage has the feature that
��
3. stevioside B glycosides crystal formation G as claimed in claim 1, it is characterised in that described crystal formation G has differential scanning calorimetric thermogram spectrum substantially as shown in Figure 2,3, 4, thermogravimetic analysis (TGA) collection of illustrative plates and dynamic water absorption collection of illustrative plates.
4. the preparation method of stevioside B glycosides crystal formation G, it is characterised in that described preparation method comprises the following steps:
(1) suspendible: in 0-100 DEG C of temperature range, by stevioside B glycosides and solvent mixing 0.1-48h, obtains suspension solution;
(2) filter: in 0-100 DEG C of temperature range, suspension solution is filtered or centrifugal, obtain white solid, obtain stevioside B glycosides crystal formation G;
(3) cooling: step (2) filtration or the settled solution after centrifugal, is cooled to 0-50 DEG C, precipitates out white solid, filter, obtain stevioside B glycosides crystal formation G;
(4) volatilization: step (2) filtration or the settled solution after centrifugal, is placed in 0-100 DEG C of temperature range and volatilizees, precipitate out white solid, obtain stevioside B glycosides crystal formation G.
5. the preparation method of stevioside B glycosides crystal formation G as claimed in claim 4, it is characterised in that in step (1), the dry purity of described stevioside B glycosides is 50-100%.
6. the preparation method of stevioside B glycosides crystal formation G as claimed in claim 4, it is characterized in that, in step (1), described solvent is one or more in water, methanol, ethanol, 1-propanol, 2-propanol, 3-methyl-1-butanol, 2-methyl isophthalic acid-propanol, acetonitrile, acetone, butanone, methylisobutylketone, methyl acetate, Ethyl formate, ethyl acetate, butyl acetate, propyl acetate, isopropyl acetate, isobutyl acetate or three fourth MEEs.
7. food compositions, it is characterised in that described food compositions contains the stevioside B glycosides crystal formation G described in any one of claim 1-3.
8. the stevioside B glycosides crystal formation G as described in any one of claim 1-3 and preparation method thereof application in food, beverage and medicine.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610173788.5A CN105646616B (en) | 2016-03-24 | 2016-03-24 | Stevioside B glycosides crystal form G, preparation method, food compositions and application |
| PCT/CN2017/074115 WO2017161985A1 (en) | 2016-03-24 | 2017-02-20 | Crystal form of rebaudioside b and preparation process therefor and use thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610173788.5A CN105646616B (en) | 2016-03-24 | 2016-03-24 | Stevioside B glycosides crystal form G, preparation method, food compositions and application |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN105646616A true CN105646616A (en) | 2016-06-08 |
| CN105646616B CN105646616B (en) | 2019-08-06 |
Family
ID=56495485
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201610173788.5A Active CN105646616B (en) | 2016-03-24 | 2016-03-24 | Stevioside B glycosides crystal form G, preparation method, food compositions and application |
Country Status (2)
| Country | Link |
|---|---|
| CN (1) | CN105646616B (en) |
| WO (1) | WO2017161985A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2017161985A1 (en) * | 2016-03-24 | 2017-09-28 | 诸城市浩天药业有限公司 | Crystal form of rebaudioside b and preparation process therefor and use thereof |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3900263A1 (en) * | 2018-12-18 | 2021-10-27 | Telefonaktiebolaget Lm Ericsson (Publ) | Method and controller for managing a microwave network |
| US20230368339A1 (en) | 2022-05-13 | 2023-11-16 | Adobe Inc. | Object class inpainting in digital images utilizing class-specific inpainting neural networks |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS52120170A (en) * | 1976-04-02 | 1977-10-08 | Toyo Sugar Refining | Separating method of sweetening substance from stevia |
| US20130267693A1 (en) * | 2010-12-13 | 2013-10-10 | Cargill, Incorporated | Crystalline forms of rebaudioside b |
| CN105037458A (en) * | 2015-07-23 | 2015-11-11 | 诸城市浩天药业有限公司 | Stevioside D glycoside crystal form A and preparation method and application thereof |
| CN105407739A (en) * | 2013-07-31 | 2016-03-16 | 帝斯曼知识产权资产管理有限公司 | Stable sweetener compositions |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102093447B (en) * | 2010-12-30 | 2015-04-08 | 青岛润浩甜菊糖高科有限公司 | Purifying method of stevioside RB |
| CN105646616B (en) * | 2016-03-24 | 2019-08-06 | 诸城市浩天药业有限公司 | Stevioside B glycosides crystal form G, preparation method, food compositions and application |
-
2016
- 2016-03-24 CN CN201610173788.5A patent/CN105646616B/en active Active
-
2017
- 2017-02-20 WO PCT/CN2017/074115 patent/WO2017161985A1/en active Application Filing
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS52120170A (en) * | 1976-04-02 | 1977-10-08 | Toyo Sugar Refining | Separating method of sweetening substance from stevia |
| US20130267693A1 (en) * | 2010-12-13 | 2013-10-10 | Cargill, Incorporated | Crystalline forms of rebaudioside b |
| CN105407739A (en) * | 2013-07-31 | 2016-03-16 | 帝斯曼知识产权资产管理有限公司 | Stable sweetener compositions |
| CN105037458A (en) * | 2015-07-23 | 2015-11-11 | 诸城市浩天药业有限公司 | Stevioside D glycoside crystal form A and preparation method and application thereof |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2017161985A1 (en) * | 2016-03-24 | 2017-09-28 | 诸城市浩天药业有限公司 | Crystal form of rebaudioside b and preparation process therefor and use thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2017161985A1 (en) | 2017-09-28 |
| CN105646616B (en) | 2019-08-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN105037458B (en) | A kind of stevioside D glycosides crystal form A, preparation method and its application | |
| CN105646616A (en) | Stevia glucoside B crystal form G as well as preparation method, food composition and application thereof | |
| CN106132408A (en) | A kind of preparation method of bicycloplatin | |
| CN108864077A (en) | The solid form and preparation method thereof of jamaicin acylate | |
| CN106866757B (en) | Stevioside M glycoside crystal form, preparation method and application | |
| CN105693791B (en) | Steviolbioside crystal form A, preparation method, food compositions and application | |
| CN103739640B (en) | A kind of stevioside A glycosides crystal and its production and use | |
| CN103739639B (en) | A kind of stevioside A glycosides crystal and its production and use | |
| CN106866666B (en) | Palbociclib crystal form compound and preparation method thereof | |
| CN105198932B (en) | Lobaplatin dihydrate, preparation method and medicinal application | |
| CN105669794A (en) | Rebaudioside B sodium salt crystal form A, and preparation method, food composition and application thereof | |
| CN105440082B (en) | A kind of lobaplatin crystal, preparation method and medicinal application | |
| CN107188800A (en) | Stevia rebaudianum alcohol crystals, its preparation method and application with crystal formation A forms | |
| CN103992219B (en) | Hydroxyl amyl group Potassium Benzoate crystal and preparation method thereof | |
| CN107118153A (en) | A kind of Rui Gefeini monohydrate crystal forms and preparation method thereof | |
| CN109651373A (en) | A kind of preparation method of Xi Gelieting phosphate monohydrate crystal form | |
| CN105669795B (en) | Stevioside C glycosides crystal forms V, preparation method, food compositions and application | |
| CN105218587B (en) | A kind of lobaplatin crystal, preparation method and medicinal application | |
| CN105198933B (en) | A kind of lobaplatin crystal, preparation method and medicinal application | |
| CN102442990A (en) | Genistein nicotinamide eutectic, its crystal and its preparation method | |
| CN105315291B (en) | A kind of crystallization and preparation method thereof of 6- arylamino pyridine ketone benzamide compound | |
| CN105440083B (en) | A kind of lobaplatin crystal, preparation method and medicinal application | |
| CN108026043A (en) | A kind of crystal form of naphthalene cycle compound | |
| CN104910144B (en) | A kind of Tropiseiron hydrochloride compound and preparation thereof | |
| CN102442991A (en) | Genistein vitamin B6 eutectic crystal and crystal and preparation method thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant | ||
| PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: Stevia B glycoside crystal form g, its preparation method, food composition and Application Effective date of registration: 20210918 Granted publication date: 20190806 Pledgee: Bank of Weifang Zhucheng sub branch Pledgor: ZHUCHENG HAOTIAN PHARM Co.,Ltd. Registration number: Y2021980009630 |
|
| PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
| PC01 | Cancellation of the registration of the contract for pledge of patent right |
Date of cancellation: 20221122 Granted publication date: 20190806 Pledgee: Bank of Weifang Zhucheng sub branch Pledgor: ZHUCHENG HAOTIAN PHARM Co.,Ltd. Registration number: Y2021980009630 |
|
| PC01 | Cancellation of the registration of the contract for pledge of patent right | ||
| PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: Steviol B glycoside crystal form G, its preparation method, food composition, and application Effective date of registration: 20230829 Granted publication date: 20190806 Pledgee: Bank of Weifang Zhucheng sub branch Pledgor: ZHUCHENG HAOTIAN PHARM Co.,Ltd. Registration number: Y2023980054328 |
|
| PE01 | Entry into force of the registration of the contract for pledge of patent right |