CN109836513A - Ocentyl succinic alpha-cyclodextrin ester and its preparation method and application - Google Patents
Ocentyl succinic alpha-cyclodextrin ester and its preparation method and application Download PDFInfo
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- CN109836513A CN109836513A CN201910201590.7A CN201910201590A CN109836513A CN 109836513 A CN109836513 A CN 109836513A CN 201910201590 A CN201910201590 A CN 201910201590A CN 109836513 A CN109836513 A CN 109836513A
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- alpha
- cyclodextrin
- dihydrochalcone
- ocentyl succinic
- cyclodextrin ester
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Abstract
The invention discloses ocentyl succinic alpha-cyclodextrin esters and its preparation method and application, have formula (I) structure:In formula (I): R indicate H orPresent invention finds ocentyl succinic alpha-cyclodextrin esters, and are applied to the embedding of sweetener aurantiin dihydrochalcone and neohesperidin dihydrochalcone, can significantly improve the solubility of dihydrochalcone-type sweetening agent in water.
Description
Technical field
The present invention relates to compound fields.It is more particularly related to ocentyl succinic alpha-cyclodextrin ester and its
Preparation method and application.
Background technique
Shaddock is Rutaceae Citrus arbor, and shaddock pulp contains Vc higher, there is the effect of helping digestion relieving alcoholism, and China is that production shaddock is big
State, there are cultivation in various regions on the south the Changjiang river, and more famous shaddock kind has Guanxi small stream honey shaddock, Wen Danyou, shatian pomelo, Pingshan shaddock, beam
Flat shaddock etc., shaddock, which is rich in aurantiin, especially pericarp, contains a large amount of aurantiin, therefore mouthfeel is partially bitter, the de- hardship of shaddock product
Letter is to be solved always for the debitterized technique in emphasis and difficult point, especially grapefruit fruit wine always in shaddock processing, existing de-
Bitter method includes addition sucrose, enzymatic hydrolysis, the de- hardship of macroreticular resin etc., but effect is not satisfactory.
Dihydrochalcone-type sweetening agent refers mainly to aurantiin dihydrochalcone and neohesperidin dihydrochalcone, is shaddock ped
The artificial sweetener that glycosides catalytic hydrogenation is prepared, not only sugariness is big, clean taste, and can also effectively shield aurantiin
Bitter taste, therefore can be added in fruit wine as the substitute of sucrose and prepare low bitter type grapefruit fruit wine, due to dihydrochalcone-type sweet tea
Taste agent can prevent saprodontia and cardiovascular disease, and can be used as the carbohydrate substitute of diabetes patient, therefore the fruit wine prepared
It is a kind of health beverages.But since the crystallization easy to form of dihydrochalcone-type sweetening agent room temperature is precipitated from solution, it is therefore desirable to
It first carries out embedding and increases its solubility.
Summary of the invention
It is an object of the present invention to provide ocentyl succinic alpha-cyclodextrin esters and its preparation method and application.
In order to realize these purposes and other advantages according to the present invention, ocentyl succinic alpha-cyclodextrin ester is provided,
Its structure formula (I):
Wherein:
R indicate H or
The present invention also provides a kind of preparation methods of ocentyl succinic alpha-cyclodextrin ester, include the following steps:
S1, octenyl succinic acid anhydride is diluted with the dehydrated alcohol of 3 times of volumes, obtains dilution；
S2, alpha-cyclodextrin (butt) is dispersed the suspension that mass fraction is 10% is made in deionized water；
S3, after suspension is stirred 1.8~2.3h under conditions of 45-55 DEG C, dilution is added dropwise, controls in 2h
It adds, in the process, while being 8.5-9.0 with the pH of 2~4%NaOH (W/V) solution control reaction system；
After S3, reaction are until system pH is constant, the pH of reaction system is adjusted to 6.5 with 2~4% hydrochloric acid solutions, its is cold
Be lyophilized it is dry, with organic solution (aqueous isopropanol) sufficiently washing after, be drying to obtain ocentyl succinic alpha-cyclodextrin ester (in 40 DEG C
For 24 hours, crushing sieves with 100 mesh sieve to get ocentyl succinic alpha-cyclodextrin ester for lower vacuum drying.).
Preferably, in the S3, the mass ratio of octenyl succinic acid anhydride and alpha-cyclodextrin in dilution is 7:100.
The present invention also provides a kind of applications of ocentyl succinic alpha-cyclodextrin ester, are applied to dihydrochalcone-type sweet taste
The embedding of agent.
The present invention is include at least the following beneficial effects: ocentyl succinic alpha-cyclodextrin ester is applied to sweetener aurantiin
The embedding of dihydrochalcone and neohesperidin dihydrochalcone can significantly improve sweetener aurantiin dihydrochalcone and new orange
The solubility of skin glycosides dihydrochalcone in water, solve dihydrochalcone-type sweetening agent when in normal temperature condition crystallization nothing easy to form
Method is applied to the problems in liquid, to improve dihydrochalcone-type sweetening agent in the application range of field of food.
Detailed description of the invention
Fig. 1 is neohesperidin dihydrochalcone scanning electron microscope (SEM) photograph；
Fig. 2 is the scanning electron microscope (SEM) photograph after the embedding of neohesperidin dihydrochalcone ocentyl succinic alpha-cyclodextrin ester；
Fig. 3 is aurantiin dihydrochalcone scanning electron microscope (SEM) photograph；
Fig. 4 is the scanning electron microscope (SEM) photograph after the embedding of aurantiin dihydrochalcone ocentyl succinic cyclodextrin ester.
Specific embodiment
Present invention will be described in further detail below with reference to the accompanying drawings, to enable those skilled in the art referring to specification text
Word can be implemented accordingly.
It should be noted that experimental method described in following embodiments is unless otherwise specified conventional method, institute
Reagent and material are stated, unless otherwise specified, is commercially obtained.
The structural formula of alpha-cyclodextrin ester are as follows:
The structural formula of octenyl succinic acid anhydride are as follows:
Ocentyl succinic alpha-cyclodextrin ester reaction equation is as follows:
Wherein, R indicate H or
The preparation method of ocentyl succinic alpha-cyclodextrin ester, includes the following steps:
S1, octenyl succinic acid anhydride is diluted with the dehydrated alcohol of 3 times of volumes, obtains dilution；
S2, alpha-cyclodextrin (butt) is dispersed the suspension that mass fraction is 10% is made in deionized water；
S3, after suspension is stirred 1.8~2.3h under conditions of 45-55 DEG C, dilution is added dropwise, controls in 2h
It adds, in the process, while being 8.5-9.0 with the pH of 2~4%NaOH (W/V) solution control reaction system；
After S3, reaction are until system pH is constant, the pH of reaction system is adjusted to 6.5 with 2~4% hydrochloric acid solutions, its is cold
Be lyophilized it is dry, with organic solution (aqueous isopropanol) sufficiently washing after, be drying to obtain ocentyl succinic alpha-cyclodextrin ester (in 40 DEG C
For 24 hours, crushing sieves with 100 mesh sieve to get ocentyl succinic alpha-cyclodextrin ester for lower vacuum drying.).
Embodiment 1
The preparation of ocentyl succinic alpha-cyclodextrin ester: 10g alpha-cyclodextrin (butt) dispersion is weighed in deionized water, system
The suspension for being 10% at mass fraction, after stirring 2h under conditions of 50 DEG C, with the dehydrated alcohol of 3 times of volumes to octenyl amber
Amber acid anhydrides is diluted, and octenyl succinic acid anhydride (additive amount is the 7.0% of alpha-cyclodextrin butt quality) is added dropwise, control exists
It is added in 2h, while being 8.5-9.0 with the pH of 3%NaOH (W/V) solution control reaction system, reaction is until system pH is constant
Afterwards, the pH of reaction system is adjusted to 6.5 with 3% hydrochloric acid solution, is freeze-dried, after sufficiently being washed with aqueous isopropanol, in
It is dried in vacuo at 40 DEG C for 24 hours, crushing sieves with 100 mesh sieve to get ocentyl succinic alpha-cyclodextrin ester (OS- α-CD).
Embodiment 2
The ocentyl succinic alpha-cyclodextrin ester prepared in embodiment 1 is embedded into neohesperidin dihydrochalcone and shaddock respectively
Skin glycosides dihydrochalcone.
Specific embedding step includes: to weigh 0.1g neohesperidin dihydrochalcone or aurantiin dihydrochalcone to try in 10mL
0.3g ocentyl succinic alpha-cyclodextrin ester is added in pipe, and distilled water is added and is settled to 10mL, heats and stirs in 75 DEG C of water-bath
30min is mixed until dissolution carries out frozen dried by the solution of core wall ratio 1:3, obtain embedding product in being stored at room temperature for 24 hours.Through testing
It is found that solubility is 0.5g/L, solubility in aurantiin dihydrochalcone normal-temperature water in neohesperidin dihydrochalcone normal-temperature water
For 0.94g/L.
In order to verify the embedding effect of ocentyl succinic alpha-cyclodextrin ester, by the neohesperidin dihydrochalcone after embedding
Solubility experiment is carried out with aurantiin dihydrochalcone.
Experimental method: embedded object (neohesperidin dihydrochalcone and aurantiin dihydro Cha Er after taking 0.1g to be lyophilized respectively
Ketone) it is dissolved in and is prepared into the solution (mass concentration 1g/L) that mass fraction is 0.1% in 70 DEG C of hot water, it is quiet at room temperature after cooling
48h is set, has seen whether acicular crystal precipitation, and look into the neohesperidin dihydrochalcone and aurantiin dihydro not embedded
You compare ketone under same experimental conditions.
Aurantiin dihydrochalcone after redissolving neohesperidin dihydrochalcone and embedding after experiment shows embedding adds water
Concentration is respectively 2.52g/L and 2.98g/L after redissolution；After standing 48 hours, there is no acicular crystal precipitation, two kinds of sweeteners
Embedding rate be 100%.It follows that ocentyl succinic alpha-cyclodextrin ester significantly improves dihydrochalcone-type sweetening agent
Speed is redissolved, requirement of the dihydrochalcone as liquid solution sweetener is met.
Scanning electron microscope experiments experiment
Aurantiin dihydrochalcone after neohesperidin dihydrochalcone and embedding after embedding in embodiment 2 is swept
Electronic Speculum detection is retouched, as a result as shown in figures 1-4.
Product is embedded in the form of sheets it can be seen from Fig. 1~4, and no acicular crystal is formed, the dihydro Cha Er after showing embedding
Ketone forms compound in conjunction with ocentyl succinic alpha-cyclodextrin ester.
Embodiment 3
By after the embedding prepared in embodiment 2 neohesperidin dihydrochalcone and aurantiin dihydrochalcone be applied to shaddock
In sub- fruit wine.
The preparation method of light hardship type grapefruit fruit wine, specific: 500g shaddock is cleaned and dries peeling, and fruit pulp is separated, will
Grapefruit flesh pericarp is put into the vial of sealing, the distilled spirit that 2L volume fraction is 40%-50% is added, sealed storage is at least
Two weeks after grapefruit fruit wine prepares, takes out fruit wine, by mass percentage, 3% soda water is added, after 0.02% embedding
Dihydrochalcone sweetener.It should be noted that the sweetener after the embedding of the application is not limited to a kind of this preparation method
Grapefruit fruit wine, grapefruit fruit wine can also using pomelo peel, grapefruit flesh and/or whole fruit of shaddock fermentation or soaking in Chinese liquor preparation
Grapefruit fruit wine.
Sensory evaluation test
It should be noted that due to neohesperidin dihydrochalcone and both sweeteners of aurantiin dihydrochalcone due to
Solubility is low, fundamentally cannot be used solution, is served only for solid feed, toothpaste and chewing gum.It can be precipitated at normal temperature, Bu Nengyou
Bitter taste in the shield solution of effect, therefore sensory evaluation can not be done.
Dihydrochalcone sweetener after embedding tests the sensory evaluation that grapefruit fruit wine bitter taste cover acts on: random choosing
20 adults are taken, men and women respectively accounts for half, carries out sensory evaluation.Evaluation criterion are as follows: the fruit wine bitter taste of sweetener is not added be 100
It is divided into standard, to having added the fruit wine of 5 kinds of sweeteners to give a mark and being described, as a result as follows:
15 people after 0.2% white granulated sugar are added to think that fruit wine bitter taste 100 divides, bitter taste cannot be blanked and sweet taste is unobvious.
14 people think that fruit wine bitter taste is blanked after neohesperidin dihydrochalcone after adding 0.2% embedding, and bitter taste drops to 60
Point or so, fruit wine becomes sugariness by bitter taste, and taste can receive, and sweet taste is in rear sweet tea refrigerant sense.
16 people think that fruit wine bitter taste is blanked after aurantiin dihydrochalcone after adding 0.2% embedding, and bitter taste drops to 70 points
Left and right, the bitter taste of fruit wine can receive, and sweet taste is in rear sweet tea refrigerant sense.
13 people after 0.2% Aspartame are added to think that fruit wine is bitter-sweet, bitter taste 100 divides, and sweet taste is apparent but cannot cover
Lid bitter taste.
12 people after 0.2% acesulfame potassium are added to think that fruit wine is bitter-sweet, bitter taste 100 divides, and sweet taste is apparent but cannot cover
Bitter taste.
Although the embodiments of the present invention have been disclosed as above, but its is not only in the description and the implementation listed
With it can be fully applied to various fields suitable for the present invention, for those skilled in the art, can be easily
Realize other modification, therefore without departing from the general concept defined in the claims and the equivalent scope, the present invention is simultaneously unlimited
In specific details and legend shown and described herein.
Claims (4)
1. ocentyl succinic alpha-cyclodextrin ester has formula (I) structure:
In formula (I):
R indicate H or
2. the preparation method of ocentyl succinic alpha-cyclodextrin ester, which comprises the steps of:
S1, octenyl succinic acid anhydride is diluted with the dehydrated alcohol of 3 times of volumes, obtains dilution；
S2, alpha-cyclodextrin is dispersed the suspension that mass fraction is 10% is made in deionized water；
S3, after suspension is stirred 1.8~2.3h under conditions of 45-55 DEG C, dilution is added dropwise, control adds in 2h
It is complete, it in the process, while being 8.5-9.0 with the pH of 2~4%NaOH solution control reaction system；
After S3, reaction are until system pH is constant, the pH of reaction system is adjusted to 6.5 with 2~4% hydrochloric acid solutions, is freezed dry
It is dry, after sufficiently being washed with organic solution, it is drying to obtain ocentyl succinic alpha-cyclodextrin ester.
3. the preparation method of ocentyl succinic alpha-cyclodextrin ester as claimed in claim 2, which is characterized in that in the S3,
The mass ratio of octenyl succinic acid anhydride and alpha-cyclodextrin in dilution is 7:100.
4. a kind of application of the ocentyl succinic alpha-cyclodextrin ester as described in claims 1 to 3 any one, feature exist
In embedding applied to dihydrochalcone-type sweetening agent.
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| CN112111024A (en) * | 2020-09-17 | 2020-12-22 | 江南大学 | Green acid-modified cyclodextrin and preparation method thereof |
| CN113559162A (en) * | 2021-08-02 | 2021-10-29 | 安徽九春堂药业有限公司 | Pharmaceutical composition for reducing blood fat and preparation method thereof |
| CN114947109A (en) * | 2021-12-14 | 2022-08-30 | 沈阳农业大学 | Preparation and application of octenylsuccinic acid cyclodextrin ester-allicin clathrate compound |
| CN115669904A (en) * | 2022-10-27 | 2023-02-03 | 上海宝鼎酿造有限公司 | Preparation method of seasoning cooking wine and seasoning cooking wine |
| CN116508750A (en) * | 2023-03-31 | 2023-08-01 | 南宁师范大学 | Application and method of cyclodextrin ester, pesticide preparation containing cyclodextrin ester and preparation method of pesticide preparation |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN113559162A (en) * | 2021-08-02 | 2021-10-29 | 安徽九春堂药业有限公司 | Pharmaceutical composition for reducing blood fat and preparation method thereof |
| CN114947109A (en) * | 2021-12-14 | 2022-08-30 | 沈阳农业大学 | Preparation and application of octenylsuccinic acid cyclodextrin ester-allicin clathrate compound |
| CN115669904A (en) * | 2022-10-27 | 2023-02-03 | 上海宝鼎酿造有限公司 | Preparation method of seasoning cooking wine and seasoning cooking wine |
| CN116508750A (en) * | 2023-03-31 | 2023-08-01 | 南宁师范大学 | Application and method of cyclodextrin ester, pesticide preparation containing cyclodextrin ester and preparation method of pesticide preparation |
| CN116508750B (en) * | 2023-03-31 | 2024-09-20 | 南宁师范大学 | Application and method of cyclodextrin ester, pesticide preparation containing cyclodextrin ester and preparation method of pesticide preparation |
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Application publication date: 20190604 |