CN107173664A - A kind of dodecyl gallate composite antioxidant for improving emulsion stability - Google Patents
A kind of dodecyl gallate composite antioxidant for improving emulsion stability Download PDFInfo
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- CN107173664A CN107173664A CN201710286424.2A CN201710286424A CN107173664A CN 107173664 A CN107173664 A CN 107173664A CN 201710286424 A CN201710286424 A CN 201710286424A CN 107173664 A CN107173664 A CN 107173664A
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- dodecyl gallate
- emulsion
- composite antioxidant
- antioxidant
- alpha
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- 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
- A23L3/00—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
- A23L3/34—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals
- A23L3/3454—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals in the form of liquids or solids
- A23L3/3463—Organic compounds; Microorganisms; Enzymes
- A23L3/3481—Organic compounds containing oxygen
- A23L3/3508—Organic compounds containing oxygen containing carboxyl groups
- A23L3/3517—Carboxylic acid esters
-
- 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
- A23L3/00—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
- A23L3/34—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals
- A23L3/3454—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals in the form of liquids or solids
- A23L3/3463—Organic compounds; Microorganisms; Enzymes
- A23L3/3481—Organic compounds containing oxygen
- A23L3/349—Organic compounds containing oxygen with singly-bound oxygen
-
- 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
- A23L3/00—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
- A23L3/34—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals
- A23L3/3454—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals in the form of liquids or solids
- A23L3/3463—Organic compounds; Microorganisms; Enzymes
- A23L3/3544—Organic compounds containing hetero rings
Abstract
The present invention relates to a kind of dodecyl gallate composite antioxidant for improving emulsion stability.According to certain molal weight than taking appropriate dodecyl gallate and alpha tocopherol to be dissolved in methanol solution respectively, it is well mixed, produces composite antioxidant.Appropriate composite antioxidant, the oxidation stability of periodic detection emulsion are added in oil-in-water emulsion.As a result show that dodecyl gallate and alpha tocopherol have synergy in emulsion, its antioxygenic property is far longer than the performance that dodecyl gallate or alpha tocopherol is used alone.
Description
Technical field
The present invention relates to a kind of composite antioxidant for improving oil-in-water emulsion oxidation stability.
Background technology
Alkyl gallates, with being obtained after fatty acid, belong to half-natural product by gallic acid.Gallic acid
In molecular structure, three hydroxyls are adjacent and are proton donor, with active reproducibility, are oxidized easily.Gallic acid and fat
After fatty alcohol, the fat-soluble of molecule is improved, alkane chain is longer, then Arrcostab is fat-soluble better, and this characteristic makes it in oil
There is good antioxygenic property in lipid product, be widely used in grease based food, the quality of food can be improved, extend
The function such as shelf-life and enhancing preservation and antisepsis.Gallic acid and its Arrcostab oxidation resistance better than China at present in grease most
Antioxidant BHT (BHT) and butylated hydroxy anisole (BHA) for often using etc..
Food emulsion system is the indispensable part of numerous food product system, due to the presence of grease, emulsion
The problem of Oxidation of Fat and Oils occurs in storage in system.So as to cause under emulsion system organoleptic quality and nutritional quality
Drop, some oxidation products of formation can also cause high risks to human body, such as be easily caused angiocardiopathy, cancer etc..
In food industry, radicals scavenging antioxidant is added, delays the generation that Oxidation of Fat and Oils chain triggers and chain is propagated, is current control
One of common method of Oxidation of Fat and Oils in pure oil-based system, in the past few decades, except some naturals (are such as confused
Repeatedly fragrant sour extract, tea polyphenol extract thing etc.) outside, not any novel antioxidant is favored by food industry, closes
It is not only expensive but also safe to the human body in the presence of threatening into antioxidant, in fact, applying more synthesis in the market
Antioxidant BHT (BHT) and the existing relevant report weighing-appliance of butylated hydroxy anisole (BHA) have potentially
Carcinogenic hidden danger.Therefore, the anti-oxidant efficiency for antioxidant being improved under the premise of limited available antioxidant is scientists face
The a major challenge faced.
In order to improve the oxidation stability of emulsion, in addition to single antioxidant is added, tentatively can will not toward contact
With antioxidant carry out compound use and reach the syneryistic effect of antioxidation activity.At present both at home and abroad in oil-in-water type breast
The simple application of separate sources anti-oxidation active substance is confined in shape liquid system the research of polyphenoils more, and on difference
The research acted synergistically between polyphenoils is few.Have not yet to see on dodecyl gallate and alpha-tocopherol in emulsus
The report of interaction in liquid.
The content of the invention
The purpose of the present invention is the Synergistic that different antioxidant progress compound uses is reached to antioxidation activity
Effect.
Molal weight is taken to compare 1:1 dodecyl gallate (100 μm of ol) and alpha-tocopherol (100 μm of ol) is dissolved in 10mL
Methanol, vibration shakes up up and down or ultrasound shakes up well mixed, produces composite antioxidant.
The dodecyl gallate purity is 98%, and the alpha-tocopherol purity is more than or equal to 96%.
The composite antioxidant is added in oil-in-water emulsion, it is 30 μM to make its ultimate density in emulsion.
The compound action effect of antioxidant is realized by following scheme：Lipid hydroperoxide in results of regular determination emulsion
With the content of hexanal, compare the POV values and acetaldehyde of emulsion of the addition composite antioxidant with adding single antioxidant
Variation tendency, and calculate dodecyl gallate and alpha-tocopherol interaction index.
Making for existing natural is improved the beneficial effects of the invention are as follows the compound use by antioxidant
With efficiency, and improve oil-in-water emulsion oxidation stability.
Brief description of the drawings
Fig. 1 is dodecyl gallate and influence schematic diagram of the alpha-tocopherol compound use to emulsion peroxide value, its
Middle Control does not represent that not plus antioxidant R12 represents dodecyl gallate, and TOH represents alpha-tocopherol, and R12+TOH represents this
Invent the dodecyl gallate and alpha-tocopherol compound use.
Fig. 2 is the influence schematic diagram that dodecyl gallate crosses hexanal content with alpha-tocopherol compound use to emulsion,
Wherein Control does not represent that not plus antioxidant R12 represents dodecyl gallate, and TOH represents alpha-tocopherol, and R12+TOH is represented
Dodecyl gallate of the present invention and alpha-tocopherol compound use.
Embodiment
Specific embodiments of the present invention are described in further detail below in conjunction with instantiation.
In the present invention, if not refering in particular to, raw material and equipment used etc. is commercially available or commonly used in the art.
Method in following embodiments, is the conventional method of this area unless otherwise instructed.
Molal weight is taken to compare 1:1 dodecyl gallate (100 μm of ol) and alpha-tocopherol (100 μm of ol) is dissolved in 10mL
Methanol, vibration shakes up up and down or ultrasound shakes up well mixed, obtains composite antioxidant.
It is prepared by emulsion：1L 10mM phosphate buffer (PH=7.0) is prepared, 0.1g Tween 20 are added.Take
1w% corn oils are dissolved in 99w%PBS buffer solutions, obtain thick emulsion with high speed dispersor stirring 2min, are existed with high pressure homogenizer
40MPa homogeneous obtains emulsion twice, is eventually adding NaN3(0.02%, w/v) is used as bacteriostatic agent.
Composite antioxidant is added in above-mentioned oil-in-water emulsion, it is 30 μM to make its ultimate density in emulsion.
The compound action effect embodiment of antioxidant：Lipid hydroperoxide and hexanal in results of regular determination emulsion
Content, and compare the hydroperoxides and the Lag time of hexanal of emulsion during with individually adding antioxidant, calculate nutgall
Sour lauryl and alpha-tocopherol interaction index.
Case study on implementation
1. the preparation of emulsion
8g NaCl、0.2g KCl、1.38g Na2HPO4With 0.2g KH2PO4It is dissolved in 1L deionized waters and is prepared into 1L 10mM
Phosphate buffer (PH=7.0), add 0.1g Tween 20.1w% corn oils are dissolved in 99w%PBS buffer solutions, with a high speed
Dispersion machine stirring 2min obtains thick emulsion, obtains emulsion twice in 40MPa homogeneous with high pressure homogenizer, adds NaN3
(0.02%, w/v) is used as bacteriostatic agent.
2. the measure of emulsion oxidation product
Emulsion is prepared according to 1 method, being separately added into dodecyl gallate and alpha-tocopherol makes it in emulsion
Concentration be 30 μM, stirring 1h make its be well mixed.Take 5mL to be transferred in ml headspace bottle, seal, 25 DEG C are kept in dark place, survey daily
Determine the peroxide value and hexanal content of emulsion.
The measure of 2.1 emulsion peroxide values
Fe2+Storing solution：Isometric 0.132M BaCl solution and 0.144M FeSO4·7H2O solution is mixed, in centrifuging and taking
Clear liquid, uses brown volumetric flask sealing preserve；Fe3+Standard stock solution：4.9769g FeSO47H2O solution be dissolved in 50mL go from
In sub- water, the dense H of 100mL are added2SO4, 20%KMnO is instilled after heating dissolving4Solution, until solution is red colour-fast and keeps
30s is constant, is settled to 1L, shakes up, and every milliliter of storing solution contains 100 μ g Fe3+.Take appropriate Fe3+Standard stock solution methanol：Just
Butanol (2:1, V/V) it is to obtain Fe that mixed liquor constant volume, which dilutes 10 times,3+Standard working solution.
Fe3+The making of standard curve：0,10,20,40,80,100,200,400 μ L Fe is pipetted respectively3+Standard work is molten
Liquid is separately added into 20 μ L 3.94M potassium thiocyanate solutions, uses methanol in 10mL test tubes：N-butanol (2:1, V/V) mixed solution
It is settled to 5mL.Vortex mixed 10s, room temperature lucifuge stands 20min, and methanol n-butanol mixed liquor is as blank control, in 510nm
Absorbance is determined under wavelength.Determine in triplicate, with absorbance values to corresponding Fe3+Content (μ g) to draw standard bent
Line.
The measure of the peroxide value of emulsion：1mL emulsion is taken, 5mL isooctane is added：Different laruyl alcohol (2:1, V/V) mix
Solution, vortex mixed are closed, then 5min is centrifuged with 5000r/min.1mL supernatants are taken, 20 μ L potassium rhodanides and 20 μ L chlorinations are added
Ferrous iron solution, again with methanol：N-butanol (2:1, V/V) mixed solution is settled to 5mL, vortex mixed 10s, and lucifuge is stood at room temperature
20min, makees blank control with methanol n-butanol mixed solution, absorbance is determined under 510nm wavelength.
Calculation formula：POV=(A × n × 0.5 × K)/(55.86 × m × 2) × 1000
In formula：POV is the peroxide value of sample, meq/kg；A is the absorbance for measuring sample liquid；K is to measure Fe3+Standard
Slope of a curve；55.86 be Fe atomic weight；The quality of grease, g in m samples；0.5 is O/Fe mol ratio；N is in absorption
The volume fraction of clear liquid；2 be the coefficient that oxygen is scaled peroxide value.Result of calculation is accurate to 0.01.
The measure of 2.2 emulsion hexanal contents
The making of hexanal standard curve：The titer of the hexanal containing 0.001mol is prepared, is diluted to respectively containing hexanal 0.002,
0.005,0.01,0.02,0.04,0.06,0.08,0.1,0.2,0.4,0.6,0.8 μm of ol gradient titer, headspace sampling
GC-MS determines hexanal content, using hexanal concentrations as abscissa, and hexanal peak area is that ordinate does standard curve.
Sample is determined：The ml headspace bottle sample introduction of packing is taken every other day.
Headspace sampling condition：65 DEG C of furnace temperature；110 DEG C of quantitative loop temperature；130 DEG C of transmission line temperature；GC equilibration times
13min；Sample injection bottle heating equilibration time 10min；Ml headspace bottle bottle internal pressure 10psi；Bottle pressing time 0.5min；When filling quantitative loop
Between 0.5min；Quantitative loop equilibration time 0.5min；Sample injection time 1min.
GC-MS conditions of work：Chromatographic column：Agilent HP-5MS(30m×250μm×0.25μm)；Split ratio：7:1；Stream
Fast 1mL/min；65 DEG C of column temperature；280 DEG C of transmission line temperature；230 DEG C of ion source temperature；150 DEG C of level Four bar temperature.
3. the interaction index of dodecyl gallate and alpha-tocopherol
Oxidation product from be detected on a small quantity be transformed into flex point corresponding time for largely producing be exactly Lag Time (p≤
0.05), represented with E.Interact index Q=experiments measured value/theoretical eapectation=[(EBlank-E(A+B)]/{[EBlank-EA]+
[EBlank-EB], wherein, A and B represent alpha-tocopherol and nutgall lauryl respectively, and A+B represents both compound uses, blank group
Refer to without antioxidant.If Q=1, dodecyl gallate shows as summation action with alpha-tocopherol；Q>1, make for collaboration
With conversely, Q<1, it is antagonism.
As illustrated, compared with adding the emulsion of single antioxidant, dodecyl gallate and alpha-tocopherol are answered
Conjunction is used so that the peroxide value and hexanal content climbing speed of emulsion slow down.Dodecyl gallate is combined with alpha-tocopherol
Use, the Lag time of hydroperoxides and hexanal are about increased 4-5 days, it is seen then that dodecyl gallate alpha-tocopherol is answered
Conjunction improves emulsion oxidation stability, i.e., both anti-oxidant efficiency of compound use in emulsion, which are significantly higher than, individually adds
Plus situation.
Dodecyl gallate is respectively 1.333 (peroxide values), 1.111 (oneself with alpha-tocopherol interaction exponential quantity
Aldehyde), interaction index is both greater than 1, it is seen then that dodecyl gallate is synergy in emulsion with alpha-tocopherol.
Claims (3)
1. a kind of dodecyl gallate composite antioxidant for improving emulsion stability, it is characterised in that：Preparation method is,
Molal weight is taken to compare 1:1 dodecyl gallate (100 μm of ol) and alpha-tocopherol (100 μm of ol) is dissolved in 10mL methanol, on
Lower vibration shakes up or ultrasound shakes up well mixed, produces composite antioxidant.
2. a kind of dodecyl gallate composite antioxidant for improving emulsion stability according to claim 1, its
It is characterised by：The dodecyl gallate purity is 98%, and the alpha-tocopherol purity is more than or equal to 96%.
3. a kind of dodecyl gallate composite antioxidant for improving emulsion stability according to claim 1, its
It is characterised by：Specifically used method is, in the oil-in-water emulsion prepared, and composite antioxidant is final in emulsion
Concentration is 30 μM.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111657480A (en) * | 2020-06-30 | 2020-09-15 | 河北工程大学 | Low-fat egg-free salad dressing with probiotic function and preparation method thereof |
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| CN102030810A (en) * | 2010-10-21 | 2011-04-27 | 华南理工大学 | Gallic acid tea sapogenol ester as well as preparation method and application thereof |
| CN102131483A (en) * | 2008-02-08 | 2011-07-20 | 昌达生物科技公司 | Non-polymeric compositions for controllable drug delivery |
| CN104130233A (en) * | 2014-07-03 | 2014-11-05 | 山东圣地嘉禾生物工程有限公司 | Method for preparing natural alpha tocopherol and mixing tocopherol by one-step method |
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2017
- 2017-04-27 CN CN201710286424.2A patent/CN107173664A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102131483A (en) * | 2008-02-08 | 2011-07-20 | 昌达生物科技公司 | Non-polymeric compositions for controllable drug delivery |
| CN102030810A (en) * | 2010-10-21 | 2011-04-27 | 华南理工大学 | Gallic acid tea sapogenol ester as well as preparation method and application thereof |
| CN104130233A (en) * | 2014-07-03 | 2014-11-05 | 山东圣地嘉禾生物工程有限公司 | Method for preparing natural alpha tocopherol and mixing tocopherol by one-step method |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN111657480A (en) * | 2020-06-30 | 2020-09-15 | 河北工程大学 | Low-fat egg-free salad dressing with probiotic function and preparation method thereof |
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