CN103005007A - Fat-soluble antioxidant of bamboo leaves and preparation method thereof - Google Patents
Fat-soluble antioxidant of bamboo leaves and preparation method thereof Download PDFInfo
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- CN103005007A CN103005007A CN2012105716023A CN201210571602A CN103005007A CN 103005007 A CN103005007 A CN 103005007A CN 2012105716023 A CN2012105716023 A CN 2012105716023A CN 201210571602 A CN201210571602 A CN 201210571602A CN 103005007 A CN103005007 A CN 103005007A
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Abstract
The invention discloses a fat-soluble antioxidant of bamboo leaves AOB-o. The total phenols content is more than or equal to 20%; the p-coumaric acid content is more than or equal to 0.5%; the solubility of the fat-soluble antioxidant of bamboo leaves in ethyl acetate is more than or equal to 3%; the fat-soluble antioxidant of bamboo leaves is yellowish-brown or tawny powder, and has slight ester smell; the fat-soluble antioxidant of bamboo leaves can be directly dissolved in edible fat and oil, medium-long-chain fatty acid and a non-polar solvent, and shows up good anti-lipid peroxidation property and thermal stability; the formation of acrylamide in heat-processed foods rich in starch can be effectively restrained; and the fat-soluble antioxidant of bamboo leaves can be used as an antioxidant for the oil and fat and an inhibitor for the acrylamide in the food industry simultaneously. The invention further discloses a preparation method of the fat-soluble antioxidant of bamboo leaves AOB-o.
Description
Technical field
The present invention relates to natural goods food additives field, specifically refer to fat-soluble AOB (AOB-o) and its production and use.Relate more specifically to the lipid-antioxidant activity effect in oil prodution industry and high temperature thereof, the high oily food manufacturing industry of processing and the inhibitory action that the amyloid Assessments of Acrylamide Generated in Heated Foodstuffs of richness is formed.
Background technology
Oxidation of Fat and Oils is a key factor that affects oil quality.The product of Oxidation of Fat and Oils can produce harmful effect to local flavor, color and luster and the quality of edible oil and fat and goods thereof, as reducing nutritional quality, shorten shelf life, producing new hazardous material.Food antioxidant refers to stop or to delay the food additives that Oxidation of Fat and Oils is rotten, improve food stability and prolongation shelf life.Directly adding antioxidant in grease is to delay the most effective method of its oxidation deterioration.Oil antioxidant commonly used in the at present food industry mainly contains: butylated hydroxy anisole (BHA), dibutyl hydroxy toluene (BHT), n-propyl gallate (PG), ditert-butylhydro quinone (TBHQ), vitamin E, vitamin(e) C palmitate (AP), Rosmarinus officinalis extract, oil-soluble tea polyphenol (OTP) etc.Wherein BHA, BHT, PG, TBHQ are the chemical synthesis antioxidant, and be best with the TBHQ antioxidant effect; Vitamin(e) C palmitate (AP), oil-soluble tea polyphenol (OTP) are the novel synthetized oxidation preventive agents that occurs in recent years, treat as natural goods, they are respectively the complex compounds of vitamin C and palmitic acid, Tea Polyphenols and aliphatic acid, can be used as fat-soluble antioxidant and nutrition fortifier and make an addition in grease or the food.Although the food antioxidant of chemical synthesis is cheap, there is certain security hidden danger, oneself is extensively restricted in the use of BHT and BHA, and TBHQ is the antioxidant that is most widely used at present, yet also by the developed countries such as Canada and European Union forbidding; Natural is comparatively safe, but because price is expensive, has limited to a certain extent them in industrial application.
AOB (Antioxidant ofbamboo leaves, AOB) be the antioxidant from natural food of the inventor's a kind of safe and efficient economy of formulating, list " People's Republic of China's food additives use sanitary standard " in (GB2760) at the beginning of 2004, oneself application of approval comprises substantially water-free fat and oil at present, shortening nut and seed class, the frying surface goods, ready-to-eat cereal, bakery product, the pickle cured meat product class, the stewed meat products class, (smoked, burn, roasting) meat, fried meat, Western-style ham, the meat enema class, the fermentation meat product class, aquatic products and goods thereof, Juice (meat) beverage, 16 classes (GB2760-2011) such as tea beverage class and dilated food.AOB adopts special process, the phenol preparation that obtains from the tender leaf of grass family (Graminae), Bambusoideae (Bambusoideae), Phyllostachys (Phyllostachys Sieb.Et Zucc) kind, its antioxidant content mainly is flavones and phenolic acid compound.Wherein, flavone compound mainly is the flavone c-glycoside take orientoside, Lutonaretin, Vitexina and Saponaretin as representative, and phenolic acid compound mainly is the derivative of cinnamic acid, comprises p-Coumaric Acid, chlorogenic acid, caffeic acid and forulic acid etc.AOB has good antioxidation activity, can the establishment lipid peroxidation, generation to lipid peroxidation product MDA (MDA) has obvious inhibitory action, can effectively resist acidolysis, pyrolysis and enzymolysis, oneself is applied in Western Sausage, Chinese style bowel lavage, pickled and cured meat, dilated food and flavouring, and obtains good result.A large amount of research and application tests show, AOB is except having good antioxygenic property, also show the effect that carcinogen in the establishment thermally processed foods (acrylamide) forms, as fried food (such as potato chips, instant noodles, fried chicken, deep-fried twisted dough sticks, fried dough twist etc.) just the height of hazards of acrylamide expose and the excessive risk field.But existing AOB preparation (the unified AOB-w that is denoted as) is a kind of composition of medium polarity bigger than normal, and is water-soluble strong, a little less than the oil-soluble, limited to a great extent its application in oils industry and high oil food field.
Acrylamide (AA) is a kind of white crystal sample material, and relative molecular mass 71.08 is stable, soluble in water under the room temperature, and polymerization and copolymerization easily occur in ethanol, ether, acetone and other organic solvent, hydrolysis occurs in sour environment generate acrylic acid.The researcher of Stockholm Univ Sweden in 2002 finds, in fried, the high temperature bakery product content of acrylamide than acrylamide in the drinking-water of World Health Organization's regulation limit the quantity of (0.5 μ g/L) exceed more than 500 times.October in the same year, the research in Britain Reading university and Nestle research center shows jointly, the acrylamide in the food be mainly derived from asparagine in the rich amyloid raw-food materials such as potato and cereal and reduced sugar at high temperature (＞120 ℃) produce by Maillard reaction.Acrylamide is a kind of neurotoxin and carcinogenic substance, and international cancer research institution (International Agency Research on Cancer, IARC) classifies acrylamide as 2A group " human possible carcinogenic substance ".Therefore, reduce food endogenous chemical pollutant acrylamide content oneself become the target that the food industry technological progress is chased.Control frying temperature, the time and with low pH value solution rinsing raw material, in grease or formula for a product, add phenol antioxidant (such as AOB-w, Tea Polyphenols, Bulbus Allii Cepae extract, apple polyphenol extract etc.) and can effectively reduce the acrylamide content in the fried food, play the effect that prevents acrylamide toxicity.Common plant polyphenol mostly is the hydrophily food antioxidant, and addition manner is mainly and makes an addition in blending process or the soaking solution.
Along with the whole society to the improving constantly of food security and nutrient health attention rate, that the frying oil that various high-grade special greases, nutrition oil, household oil and food industry are used, shortening, margarine oil's wet goods product are needed badly is natural, safety, high-quality, efficient oil-soluble inhibitor.Increase at present the fat-soluble conventional method of antioxidant solvent method, emulsion process and molecular modification method are arranged.The product system that front two kinds of methods obtain is unstable, and low temperature or high speed centrifugation can make dissolved matter separate out once again.In order to increase the solubility of AOB-w in grease, the inventor once attempted the microemulsified with AOB-w, but the stability of AOB microemulsion is subjected to environment (such as temperature etc.) impact very large in actual use.Because the high temperature frying is processing mode common in the food industry, microemulsion is easy to breakdown of emulsion so that oil product outward appearance and quality all descend greatly under the hot conditions.
Summary of the invention
The technical problem to be solved in the present invention provides a kind of fat-soluble AOB (AOB-o) and its production and use.
In order to solve the problems of the technologies described above, the invention provides a kind of fat-soluble AOB AOB-o, total phenol content 〉=20%, p-Coumaric Acid content 〉=0.5%, the solubility in ethyl acetate 〉=3%, yellowish-brown or yellowish-brown powder, slightly ester flavor; Can directly be dissolved in edible oil and fat, middle LCFA and the non-polar solven, have the non-oxidizability and the heat endurance that are better than commercially available similar oil antioxidant product (oil-soluble tea polyphenol, ditert-butylhydro quinone), and the formation of the rich amyloid Assessments of Acrylamide Generated in Heated Foodstuffs of energy establishment, can in food industry, use as oil antioxidant and acrylic amide restrainer simultaneously.
Improvement as fat-soluble AOB AOB-o of the present invention: take water-soluble AOB AOB-w as raw material, with the fat acyl chloride (acylate of aliphatic acid; during reaction as the aliphatic acid donor) ester exchange Powdered, the graininess or the Formulation that form, dissolve in edible oil and fat and/or in, become liquid formulation in the LCFA.
Further improvement as fat-soluble AOB AOB-o of the present invention: the infrared transmission spectra behind pressing potassium bromide troche all is presented at 1700cm
-1Near strong carbonyl absorption peak is arranged, and 3400cm
-1Near hydroxyl absworption peak significantly weakens than AOB-w.
The present invention provides the preparation method of a kind of fat-soluble AOB AOB-o simultaneously, may further comprise the steps:
1) in low polar solvent I, under the effect of base catalyst, water-soluble AOB AOB-w and fat acyl chloride are in 30 ℃ ~ 50 ℃ acylation reaction 5h ~ 10h; Water-soluble AOB AOB-w: fat acyl chloride: the mol ratio of base catalyst is 1:0.5 ~ 2.5:0.8 ~ 3;
2) with step 1) the pH value of gained product transfers to neutrality, vibration evenly, standing demix; Get the organic phase on upper strata, the washing final vacuum is concentrated, gets fat-soluble AOB AOB-o crude product.
Further improvement as the preparation method of fat-soluble AOB AOB-o of the present invention: fat-soluble AOB AOB-o crude product is made with extra care:
After fat-soluble AOB AOB-o crude product volumetric concentration was the dissolving of 85% ~ 92% ethanol-water solution, with low polar solvent I extraction, then concentrated, drying got fat-soluble AOB AOB-o.
Remarks explanations: above-mentioned volumetric concentration is that the consumption of 85% ~ 92% ethanol-water solution only need guarantee that fat-soluble AOB AOB-o crude product is got final product by whole dissolvings.
Further improvement as the preparation method of fat-soluble AOB AOB-o of the present invention: the base catalyst step 1) is sodium acetate, sodium acid carbonate or triethylamine.
Further improvement as the preparation method of fat-soluble AOB AOB-o of the present invention: fat acyl chloride is the fat acyl chloride that forms after the aliphatic acid of C8 ~ C18 chain length and the acylating reagent acidylate.
Further improvement as the preparation method of fat-soluble AOB AOB-o of the present invention:
The aliphatic acid of C8 ~ C18 chain length is sad, capric acid, palmitic acid, laurate, cinnamic acid or stearic acid;
Acylating reagent is nitrosyl chloride, chlorosulfuric acid, phosphoryl chloride phosphorus oxychloride or thionyl chloride.
In the present invention, fat acyl chloride can be selected lauroyl chloride, cinnamoyl chloride, palmitoyl chloride, stearyl chloride; The palmitoyl chloride of preferred C16.
Further improvement as the preparation method of fat-soluble AOB AOB-o of the present invention:
Step 1) in: low polar solvent I is ethyl acetate, n-hexane, benzene or acetone, and the amount ratio of water-soluble AOB AOB-w and low polar solvent I is 1g:25 ~ 125mL;
Step 2) in: the watery hydrochloric acid take concentration as 0.8 ~ 1.2mol/L, dilute sulfuric acid or rare nitric acid regulating step 1) the pH value of gained product transfers 7.0 ± 0.5.
Further improvement as the preparation method of fat-soluble AOB AOB-o of the present invention:
In the step that the AOB-o crude product is made with extra care, low polar solvent I is benzinum, ether or n-hexane.
Optimal process parameter of the present invention is as follows:
Water-soluble AOB AOB-w (hereinafter to be referred as AOB-w): fat acyl chloride: the mol ratio of base catalyst is 1:0.8 ~ 1.5:0.8 ~ 1.5.
Step 1 in preparation method of the present invention) in:
When reaction temperature was lower than 30 ℃, AOB-w can't be esterified, and modified-reaction occurs hardly.When temperature was higher than 50 ℃, the AOB-o sample color and luster that obtains was partially black, the antioxygenic property variation, be dissolved in edible oil and/or in, larger on east of oil impact behind the LCFA.Evidence, preferred range of reaction temperature is 35 ℃ ~ 45 ℃.
Step 1 in preparation method of the present invention) react under the raw material ratio that sets and the temperature conditions, the time is too short, and degree of esterification is inadequate, and dissolubility is relatively poor; Overlong time, degree of esterification is too high, and is esterified because crossing polyhydroxy although oil-soluble is better, easily causes antioxygenic property to descend.Evidence, the preferred reaction time is 6h ~ 8h.
Sample yield of the present invention is generally 0.65 ~ 0.90g/g (AOB-o/AOB-w).
Fat-soluble AOB AOB-o provided by the invention (hereinafter to be referred as AOB-o) can directly be dissolved in edible oil and fat and/or in, LCFA, indissoluble or water insoluble; Effect with Anti-oxidant.Preparation method of the present invention is oxygen acidylate method, AOB-o of the present invention is had be better than the anti-oxidant and acrylamide rejection of commercially available similar oil antioxidant product (OTP, TBHQ, frying oil antioxidant).
The infrared transmission spectra of AOB-o of the present invention behind pressing potassium bromide troche is presented at 1700cm
-1Near strong carbonyl absorption peak is arranged, and 3400cm
-1Near hydroxyl absworption peak significantly weakens (seeing Fig. 1) than AOB-w.
AOB-o ultra-violet absorption spectrum of the present invention has the last one absworption peak (seeing Fig. 2) at 240～280nm and 300～350nm among.
AOB-o of the present invention can directly be dissolved in edible oil and fat (such as palm oil, peanut oil, corn oil, rapeseed oil, lard, butter, butter, fish oil, camellia oil, pecan oil, linseed oil, olive oil, sunflower oil, purple perilla wet goods), general addition is the 0.01-0.05% of oil quality mark, in also AOB-o can being added to certain proportion (mass fraction 1 ~ 20%), in the long-chain fat acid solution (such as hot certain herbaceous plants with big flowers acid glyceride, glyceryl laurate ester, tristerin etc.), as the oil antioxidant use of liquid state.
The present invention compared with prior art, its advantage is: (AOB-w) compares with water-soluble AOB, AOB-o of the present invention can directly be dissolved in edible oil and fat, middle LCFA and the non-polar solven, shows good anti peroxidation of lipid performance and heat endurance.Adopt grease oxidation rancid instrument (Rancimat) to compare 130 ℃ of lower AOB-o and the impact of other antioxidants on lard and the test of palmitic antioxidative stabilizer, the result shows that AOB-o can make 3.74 times of the antioxygenic property increases of lard, palmitic antioxygenic property increase by 1.58 times, and the performance of Anti-oxidant and heat endurance thereof are better than commercially available similar oil antioxidant product (OTP, TBHQ, frying oil antioxidant) under its high temperature.AOB-o of the present invention is used for the fried potato goods, service life that can the significant prolongation frying oil, and significantly reduce the content of acrylamide in the goods, shows anti-oxidant and suppress the double effects of the third poison.AOB-o is applied to food processing industry or the rich grease-contained field of health care products of oil prodution industry, the high oil of high temperature, can prolong the antioxygenic property of lipid, and show the heat endurance that is better than commercial like product (OTP, TBHQ, frying oil antioxidant), therefore in food industry, have broad application prospects.
In sum, main purpose of the present invention is on the basis of water-soluble AOB (AOB-w), further obtain the oil-soluble goods, can directly make an addition in the edible oil and fat, bring into play Anti-oxidant and suppress the double action that acrylamide forms in mode more easily.
Description of drawings
Below in conjunction with accompanying drawing the specific embodiment of the present invention is described in further detail.
Fig. 1: AOB-o and AOB-w infrared transmission spectra comparison diagram;
Fig. 2: AOB-o and AOB-w ultra-violet absorption spectrum comparison diagram;
Fig. 3: AOB-o and AOB-w RPLC (RP-HPLC) finger-print comparison diagram;
Among Fig. 3: the 1--chlorogenic acid; The 2--caffeic acid; The 3--Lutonaretin; The 4--orientoside; The 5--p-Coumaric Acid; The 6--Saponaretin; The 7--Vitexina; The 8--forulic acid.
(annotate: different instruments, different splitter even different time sample introduction, the retention time of each component can be different, but the eluting order of each component is basic identical in the RP-HPLC spectrogram.)
The specific embodiment
The preparation of embodiment 1 palmitoyl chloride (being routine techniques)
Take by weighing palmitic acid 12.821g (0.05mol), put in the 250mL cucurbit, add 7.254mL thionyl chloride (0.10mol), slowly shake, with 1mol/L NaOH solution absorption tail gas (HCl and SO
2) or reaction unit being placed fume hood, 37 ℃ of reaction 5h are to without Bubble formation, and after the cooling during without solid, decompression distillation steams residual thionyl chloride.Identify that through UV scanning thionyl chloride is whether residual and whether the fat acyl chloride peak arranged.
The palmitoyl chloride finished product stores in 4 ℃ of condition lower seals, and strict water proof is preserved (palmitoyl chloride is met water and namely decomposed).
UV scanning authentication method (absorbing wavelength 250nm place is fat acyl chloride, and the 280nm place then is the complete thionyl chloride of unreacted).
Sample concentration: 0.01mL/mL chloroform.
The standby AOB-o of embodiment 2 oxygen acidylate legal systems
AOB-w is purchased from Hangzhou Youmeite Technology Co., Ltd., general flavone content 〉=20%, phenolic content 〉=20%, Lutonaretin 〉=2.0%.Taking by weighing AOB-w17.114g (calculates by the mean molecule quantity of 8 characteristic phenolic compounds wherein and to be about 0.2mol; lower same) as raw material; add proper amount of acetone (about 500mL; raw material is immersed in the acetone; can adopt Sonication assisted treatment), add lauroyl chloride (lauric acylate, during reaction as the laurate donor) 115.6mL (0.5mol); divide 3 times and add sodium acid carbonate 40.205g (0.5mol), 35 ℃ of reaction 8h.After reaction finishes, add 1mol/L watery hydrochloric acid and regulate pH7.0, layering is left standstill in vibration.After washing was positioned at twice of the organic layer (consumption of each pure water is 250mL) on upper strata, Vacuum Concentration reclaimed acetone to doing, and collects AOB-o crude product 25.96g.
After dissolving above-mentioned AOB-o crude product with 91% ethanol-water solution (v/v) 200mL, with benzinum (30-60 ℃) extracting twice (each solvent load is 200mL), Vacuum Concentration (under 40 ℃) is to viscous liquid, vacuum drying to moisture is lower than 8% of mass ratio, fat-soluble AOB (AOB-o) 14.01g that obtains making with extra care.
The standby AOB-o of embodiment 3 oxygen acidylate legal systems
The same AOB-w17.114g that takes by weighing is as reaction substrate; add an amount of benzene (about 800mL; raw material is immersed in the benzene; can adopt Sonication assisted treatment); add the cinnamoyl chloride (acylate of cinnamic acid; during reaction as the cinnamic acid donor) 14.3mL (0.1mol), add sodium acetate 16.406g (0.2mol), 40 ℃ of reaction 8h minutes for 3 times.After reaction finishes, add 1mol/L watery hydrochloric acid and regulate pH7.0, layering is left standstill in an amount of vibration.After washing was positioned at twice of the organic layer (consumption of each pure water is 250mL) on upper strata, Vacuum Concentration reclaimed benzene to doing, and collects to get AOB-o crude product 29.24g.
Behind 88% ethanol-water solution (v/v) 200mL dissolving AOB-o crude product, with benzinum (30-60 ℃) extracting twice (each solvent load is 200mL), Vacuum Concentration (under 40 ℃) is to viscous liquid, vacuum microwave drying to moisture is lower than 8% of mass ratio, fat-soluble AOB (AOB-o) 13.30g that obtains making with extra care.
The standby AOB-o of embodiment 4 oxygen acidylate legal systems
The same AOB-w17.114g that takes by weighing is as reaction substrate; add an amount of ethyl acetate (about 500mL; raw material is immersed in the ethyl acetate; can adopt Sonication assisted treatment); add the palmitoyl chloride (acylate of palmitic acid; during reaction as the palmitic acid donor) 60.8mL (0.2mol), add sodium acid carbonate 16.802g (0.2mol), 35 ℃ of reaction 6h minutes for 3 times.After reaction finishes, add 1mol/L watery hydrochloric acid and regulate pH7.0, layering is left standstill in an amount of vibration.After twice of the organic layer washing, Vacuum Concentration reclaims ethyl acetate to doing, and collects AOB-o crude product 22.35g.
After dissolving above-mentioned AOB-o crude product with 90% ethanol-water solution (v/v) 200mL, with benzinum (30-60 ℃) extracting twice (each solvent load is 200mL), Vacuum Concentration (under 40 ℃) is to viscous liquid, vacuum freeze drying to moisture is lower than 8% of mass ratio, the fat-soluble AOB AOB-o11.64g that obtains making with extra care.
AOB-o sample and the raw material (AOB-w) thereof of embodiment 4 gained are carried out infrared spectrum analysis according to the method for GB/T6040 regulation behind pressing potassium bromide troche, measurement result is seen Fig. 1.AOB-w is at 3400cm
-1, 2930cm
-1, 1610cm
-1, 1075cm
-1Deng near have characteristic to absorb, show respectively the stretching vibration of hydrocarbon key on phenolic hydroxyl group, the phenyl ring, phenyl ring skeleton and carbonyl; And AOB-o is at 3400cm
-1About the phenolic hydroxyl group absworption peak greatly weaken, at 1700cm
-1Near the strong carbonyl absorption peak of appearance.
AOB-o sample and the raw material (AOB-w) thereof of embodiment 4 gained are dissolved in the solution that the pure methyl alcohol of analysis is made into 0.15mg/mL left and right sides concentration, carry out UV scanning in 200nm～400nm wave-length coverage, ultraviolet spectrogram is seen Fig. 2.AOB-o and AOB-w all have the last one absworption peak between 240～280nm, strong absworption peak once between 300～350nm, but the AOB-o peak strength weakens than AOB-w is obvious.
Remarks explanations: the AOB-o sample of embodiment 2, embodiment 3 gained after testing, the spectrogram of gained infrared spectrum and ultraviolet spectra is identical with embodiment 4 gained samples.
The mensuration of the total phenol content of embodiment 5AOB-o, p-Coumaric Acid content, acetic acid ethyl dissolution degree and HPLC finger-print
(1) mensuration of total phenol content
Forint (Folin) reagent is extremely unstable under alkali condition, can make phenolic compound reduction and is blue reaction.In P-hydroxybenzoic acid concentration 0.0005～0.016mg/mL scope, its concentration and absorbance meet Beer law, and available P-hydroxybenzoic acid is that reference substance carries out the total phenol content that quantitative colorimetric estimation gets sample.
The P-hydroxybenzoic acid standard liquid: take by weighing the P-hydroxybenzoic acid standard items 25.0mg that is dried to constant weight, the dissolve with ethanol solution with 90% also is settled to 100mL, is made into 0.250mg/mL P-hydroxybenzoic acid standard liquid.
Accurately draw P-hydroxybenzoic acid standard liquid 0,0.05,0.10,0.20,0.40,0.80,1.20mL, be equivalent to be diluted with water to respectively 10.0mL in P-hydroxybenzoic acid 0,0.0125,0.025,0.050,0.10,0.20, the 0.30mg immigration 25mL tool plug test tube; Each adds 1.0mL Folin reagent and 2.0mL20%Na
2CO
3The aqueous solution (mass fraction), test tube heats 30min in 50 ℃ ± 1 ℃ water bath with thermostatic control, then with water cooling and be diluted to 25mL.Room temperature is placed 30min, measures the absorbance of 745nm with the 1cm cuvette.Take trap as ordinate, concentration is as abscissa drawing standard curve or ask for equation of linear regression.
Take by weighing the AOB-o sample of embodiment 2, embodiment 3 and embodiment 4 preparations, being made into concentration with volume ratio 90% ethanolic solution is solution about 2mg/mL, with the qualitative filter paper filtration, namely gets sample.Accurately draw sample solution 1mL, by the operating procedure in the above-mentioned standard curve making, the place carries out absorbance measurement in the 745nm wavelength.
According to standard working curve, obtain the P-hydroxybenzoic acid content that is equivalent to the sample absorbance.P-hydroxybenzoic acid content is with w
1Expression, its numerical value represents with %, by formula (1) calculates the total phenol content of sample:
In the formula:
w
1---the total phenol content in the sample, %;
m
1---the phenolic content in the test solution that the establishing criteria opisometer is calculated, unit are milligram (mg);
V
2---liquid cumulative volume to be measured, unit are milliliter (mL);
m
2---for the sample sampling amount, unit is milligram (mg);
V
1---liquid to be measured divides gets volume, and unit is milliliter (mL).
Measurement result shows that the total phenol content of the AOB-o sample of embodiment 2, embodiment 3 and embodiment 4 preparations is respectively 22.57%, 23.19% and 28.46%.
(2) p-Coumaric Acid assay
Sample dissolves through methyl alcohol, take acetonitrile-1% acetic acid aqueous solution as mobile phase, be liquid-phase chromatographic column (the Luna C18ODS post of filler in order to C18, column length 250mm, internal diameter 4.6mm, in-built C18 filler, particle diameter 5 μ m or suitable person) and UV-detector or PDAD, p-Coumaric Acid in the sample is carried out RPLC separation and mensuration, and more qualitative with the standard items retention time, the peak area external standard method is quantitative.
The configuration of standard reserving solution: accurately take by weighing p-Coumaric Acid standard items 10mg (being accurate to 0.0001g), with methyl alcohol dissolving and be settled to 10mL, mixing is put in the refrigerator and is preserved.This solution 1mL contains p-Coumaric Acid 1.0mg.
Accurately draw a certain amount of p-Coumaric Acid standard liquid, dilute respectively 8,10,16,32,64,128 and 256 times, difference sample introduction 10 μ L, under following regulation chromatographic condition, carry out chromatography, according to different sample sizes and the corresponding spectrum peak area of p-Coumaric Acid standard liquid, take chromatographic peak area as ordinate, p-Coumaric Acid concentration is abscissa, the drawing standard curve.
Chromatographic column: Luna C18ODS post, column length 250mm, internal diameter 4.6mm, in-built C18 filler, particle diameter 5 μ m or suitable person.
The reference color spectral condition is as follows:
Detect wavelength: 330nm.Column temperature: 40 ℃.Mobile phase: A. acetonitrile; B.1% acetic acid aqueous solution (v/v).Condition of gradient elution: during 0～15min, A15%, B85%; During 15～25min, A15%～40%, B85%～0%; During 25 ~ 34min, A40%, B60%; During 34～40min, A40%～15%, B60%～85%.Flow: 1.0mL/min.Sample size: 10 μ L.
Sample detection: accurately take by weighing AOB sample 100mg (being accurate to 0.0001g), with dissolve with methanol solution and be settled to 100mL, filter through miillpore filter (0.45 μ m), namely get sample solution.Accurately draw sample solution 10 μ L, under the regulation chromatographic condition, carry out chromatography, qualitative with retention time, the peak area external standard method is quantitative.
P-Coumaric Acid content is with w
2Expression, its numerical value represent with %, by formula (2) calculating:
In the formula:
w
2---the content of p-Coumaric Acid in the sample, %;
c
1---the p-Coumaric Acid concentration in the test solution that the establishing criteria opisometer is calculated, unit is every milliliter (mg/mL) of milligram;
V
3---for the sample constant volume, unit is milliliter (mL);
m
3---for the sample sampling amount, unit is milligram (mg).
Measurement result shows that the p-Coumaric Acid content of embodiment 2, embodiment 3 and embodiment 4 preparation AOB-o is respectively 0.60%, 0.62% and 0.71%.
(3) mensuration of acetic acid ethyl dissolution degree
Get the tool plug triangular flask of 200mL, be dried to constant weight (m
4) after, accurately take by weighing 100g ethyl acetate (being accurate to 0.01g), then the AOB-o sample (being accurate to 0.01g) that adds 5～10g embodiment 2, embodiment 3 and embodiment 4 preparations, stir at the following edged of 25 ℃ of conditions, it is fully dissolved, leave standstill 10min, pour out supernatant, bottle and residue are dried to constant weight (m
6), according to the Mass Calculation acetic acid ethyl dissolution degree that alleviates.
The acetic acid ethyl dissolution degree is with w
3Expression, its numerical value is to restrain each hectogram ethyl acetate (g/100g) expression, and by formula calculate (3)::
w
3=m
4+m
5-m
6……………………………………(3)
In the formula:
w
3The acetic acid ethyl dissolution degree of-sample, unit is gram each hectogram (g/100g);
m
4The weight of-dry Vee formation bottle, unit is gram (g);
m
5-for the sample sampling amount, unit is gram (g);
m
6The quality of-dry Vee formation bottle and residue, unit is gram (g).
Measurement result shows that the acetic acid ethyl dissolution degree of embodiment 2, embodiment 3 and embodiment 4 preparation AOB-o is respectively 3.69g/100g, 3.75g/100g and 4.62g/100g.
(4) mensuration of HPLC finger-print
AOB-o sample and raw material A OB-w thereof use respectively methyl alcohol (chromatographically pure) dissolving, take acetonitrile (chromatographically pure)-1% acetic acid (top grade the is pure) aqueous solution as mobile phase, be liquid-phase chromatographic column and UV-detector or the diode array detector of filler in order to C18, contrast with the standard diagram and the sample collection of illustrative plates that contain eight reference substances such as Lutonaretin, orientoside, Saponaretin, Vitexina, p-Coumaric Acid, chlorogenic acid, caffeic acid, forulic acid, determine active ingredient and the classification difference of AOB-o sample.
Standard reserving solution: take by weighing respectively a small amount of Lutonaretin, orientoside, Saponaretin, Vitexina, p-Coumaric Acid, chlorogenic acid, caffeic acid, forulic acid standard items (purity 〉=98.0%), dissolve and be settled to 10mL with methyl alcohol (chromatographically pure), mixing, put in the refrigerator and preserve, this solution is the mixed mark solution of eight reference substances.
Chromatographic column: Luna C18ODS post, column length 250mm, internal diameter 4.6mm, in-built C18 filler, particle diameter 5 μ m or suitable person.
The reference color spectral condition is as follows:
Detect wavelength: 330nm.Column temperature: 40 ℃.Mobile phase: A. acetonitrile; B.1% acetic acid aqueous solution (v/v).Condition of gradient elution: during 0～15min, A15%, B85%; During 15～25min, A15%～40%, B85%～0%; During 25 ~ 34min, A40%, B60%; During 34～40min, A40%～15%, B60%～85%.Flow: 1.0mL/min.Sample size: 10 μ L.
Take by weighing the AOB-o sample 10.75mg of embodiment 4 preparation, dissolve and be settled to 5mL with methyl alcohol (chromatographically pure), through miillpore filter (0.45 μ m) filtration, namely get sample solution.Accurately draw sample solution 10 μ L, under above-mentioned chromatographic condition, carry out chromatography, qualitative with retention time.
Measurement result is seen Fig. 3.
Remarks explanations: the AOB-o sample of embodiment 2, embodiment 3 gained after testing, the AOB-o of the result of gained HPLC finger-print such as embodiment 4 gained.
Embodiment 6AOB-o is on the impact of lard antioxidative stabilizer
Leaf fat is purchased from market, Hangzhou, boils to get experiment lard.Take by weighing 20g lard, press respectively the AOB-o sample that mass fraction 0,0.01%, 0.02%, 0.03%, 0.04%, 0.05% concentration add embodiment 2, embodiment 3 and embodiment 4 preparations, Sonication assisted treatment 10min is to accelerate its dissolving mixing.Take by weighing the lard sample behind the interpolation AOB-o about 3g; adopt grease oxidation rancid instrument (Rancimat) to compare 130 ℃ of lower AOB-o and the impact of other antioxidants on lard and the test of palmitic antioxidative stabilizer; air velocity is 20L/h; method according to the GB/T21121-2007 regulation is tested, and compares the AOB-o sample to the impact of lard antioxidative stabilizer by the protection factor (PF).Result of the test is as shown in table 1.
Show that AOB-o can significantly strengthen the antioxidative stabilizer of lard, and it is not on existing proportional relationship between the impact of lard antioxidative stabilizer and the additive capacity, strengthen the lard antioxidation when mass fraction is 0.02% addition the most obvious, the AOB-o sample that adds mass fraction 0.02% embodiment 2, embodiment 3 and embodiment 4 can strengthen respectively 2.93 times of lard antioxidative stabilizers, 3.32 times and 3.74 times.
Table 1AOB-o is on the impact of lard antioxidative stabilizer
Embodiment 7AOB-o is on the impact of palm oil antioxidative stabilizer
Take by weighing 20g and do not contain the palm oil that adds antioxidant, press respectively the AOB-o sample that mass fraction 0,0.01%, 0.02%, 0.03%, 0.04%, 0.05% dosage add embodiment 2, embodiment 3 and embodiment 4 preparations, Sonication assisted treatment 10min is to accelerate its dissolving mixing.Take by weighing the palm oil sample behind the interpolation AOB-o about 3g; adopt grease oxidation rancid instrument (Rancimat) to compare 130 ℃ of lower AOB-o and the impact of other antioxidants on lard and the test of palmitic antioxidative stabilizer; air velocity is 20L/h; method according to the GB/T21121-2007 regulation is tested, and compares the AOB-o sample to the impact on the palm oil antioxidative stabilizer by the protection factor (PF).
Result of the test is as shown in table 2, show that AOB-o can significantly strengthen the palm oil antioxidative stabilizer, it is not on existing proportional relationship between the impact of palm oil antioxidative stabilizer and the additive capacity, strengthen the palm oil antioxidation with mass fraction 0.03% addition the most obvious, add mass fraction 0.03% embodiment 2, embodiment 3 and embodiment 4AOB-o sample and can strengthen respectively 1.20 times of palm oil antioxidative stabilizers, 1.31 times and 1.58 times.
Table 2AOB-o is on the impact of palm oil antioxidative stabilizer
The heat endurance of embodiment 8 different antioxidants and to the oxidation-stabilized sex comparison of palm oil
Take do not contain add antioxidant palm oil as subjects, add respectively AOB-o sample, the oil-soluble tea polyphenol (OTP of mass fraction 0.02% embodiment 2, embodiment 3 and embodiment 4 preparations, be purchased from beauteously bio tech ltd of Pu Li, polyphenol content 〉=25%, lower with) and the frying oil antioxidant (be purchased from the Dongguan City Guangyi Food Additive Industry Co, product form is take ditert-butylhydro quinone, the vitamin(e) C palmitate liquid formulation as forming after active ingredient makes an addition to corn oil; Lower same), in 175 ℃ of heating 20min.Get the palm oil sample that adds above-mentioned antioxidant about 3g before and after the heating, adopt grease oxidation rancid instrument (Rancimat) to compare 130 ℃ of lower AOB-o and the impact of other antioxidants on palmitic antioxidative stabilizer test, air velocity is 20L/h, method according to the GB/T21121-2007 regulation is tested, by relatively AOB-o sample and the heat endurance of other antioxidants and the impact of anti-palm oil oxidation stability thereof of induction time.
Result of the test is as shown in table 3.From table, can find out, add different antioxidants after lipid-antioxidant activity stability enhancing is all arranged, best with the frying oil antioxidant effect; Yet all oil sample antioxidative stabilizers all reduce after the heating, and its empty fall is maximum, reaches 71.6%.Behind the heating 20min, the anti-palm oil oxidation stability of OTP descends 58.9%, the anti-palm oil oxidation stability of frying oil antioxidant descends 26.7%, the palm oil oxidation stability of adding mass fraction 0.02% embodiment 2, embodiment 3 and embodiment 4AOB-o sample descends respectively 23.9%, 21.3% and 19.5%, explanation is compared with commercially available similar oil antioxidant product, and AOB-o shows good heat endurance and anti-palm oil oxidisability.
Table 3AOB-o and other antioxidant heat endurances and to the oxidation-stabilized sex comparison of palm oil
Take by weighing 3kg and do not contain the palm oil that adds antioxidant, add respectively AOB-o sample, oil-soluble tea polyphenol (OTP), the frying oil antioxidant of mass fraction 0.02% embodiment 2, embodiment 3 and embodiment 4 preparations, until completely dissolved, in 175 ℃ of potato chips 35s, every group of potato chips consumption is 200g.After the potato chips cooling, add the grease in a certain amount of benzinum (30-60 ℃) submergence 12h extraction potato chips.Accurately take by weighing the 3g oil sample; adopt grease oxidation rancid instrument (Rancimat) to compare 130 ℃ of lower AOB-o and the impact of other antioxidants on palmitic antioxidative stabilizer test; air velocity is 20L/h; test according to the GB/T21121-2007 prescriptive procedure, determine that by the protection factor different antioxidants are on the impact of palm oil antioxidative stabilizer.
Result of the test is as shown in table 4.Adding different antioxidants all can increase the antioxidative stabilizer of potato chips, wherein the frying oil antioxidant can strengthen 1.47 times of potato chips antioxidative stabilizers, OTP can increase by 1.41 times of potato chips antioxidative stabilizers, it is best that the AOB-o sample of the present invention's preparation strengthens the anti-oil peroxidation performance of potato chips, can reach 2.01 times.
The different antioxidants of table 4 are on the impact of potato chips antioxidative stabilizer
| Group | The protection factor |
| 0.02% frying oil antioxidant | 1.47±0.01 |
| 0.02%OTP | 1.41±0.02 |
| The AOB-o of 0.02 |
1.78±0.04 |
| The AOB-o of 0.02% embodiment 3 | 1.91±0.02 |
| The AOB-o of 0.02% embodiment 4 | 2.01±0.03 |
Take by weighing 2kg and do not contain the palm oil that adds antioxidant, add respectively AOB-o sample and ditert-butylhydro quinone (the TBHQ powder formulation of mass fraction 0.02% embodiment 2, embodiment 3 and embodiment 4 preparations, be purchased from the Dongguan City Guangyi Food Additive Industry Co, lower same), until completely dissolved, in 180 ℃ of fries 7min, every group of French fries consumption is 200g.Get an amount of chip potato sample and pulverize rear detection acrylamide content with mortar.Result of the test is as shown in table 5.The result shows, the inhibiting rate that TBHQ generates acrylamide only is that the AOB-o sample of 5.1%, embodiment 2, embodiment 3 and embodiment 4 preparations is respectively 16.5%, 18.8% and 20.6% to the inhibiting rate that acrylamide generates, and effect all is better than TBHQ.
The different antioxidants of table 5 are to the comparison of potato chips acrylamide inhibition
| Group | Acrylamide content (μ g/kg) | Inhibiting rate (%) |
| Blank | 2340±22.37 | 0 |
| 0.02%TBHQ | 2221±27.57 | 5.09±0.31 |
| The AOB-o of 0.02 |
1954±14.57 | 16.5±1.09 |
| The AOB-o of 0.02% embodiment 3 | 1901±17.27 | 18.8±1.25 |
| The AOB-o of 0.02% embodiment 4 | 1858±15.73 | 20.6±1.03 |
Embodiment 11 different antioxidants are on the impact of cake peroxide value
Take by weighing 100g and do not contain the palm oil that adds antioxidant, add respectively AOB-o sample, oil-soluble tea polyphenol (OTP), the ditert-butylhydro quinone (TBHQ powder formulation) of mass fraction 0.02% embodiment 2, embodiment 3 and embodiment 4 preparations, fully stand-by after the dissolving.Take by weighing 300g white sugar and 500g egg, 120r/min beats at a slow speed the butter that adds the different antioxidants of the above-mentioned interpolation of 20g behind the 8min mixing and forms egg and stick with paste, and does contrast with blank oil sample.400g flour and 5g baking powder are added the egg paste, stir evenly at a slow speed the formation batter.Batter is injected in the mould, and 180 ℃ bake 20min.After the cake cooling, add the grease in a certain amount of benzinum (30-60 ℃) submergence 12h extraction cake.Accurately take by weighing 2g and extract oil sample, test according to the method for GB/T5009.37-2003 regulation, measure peroxide (POV) value of each cake sample oil sample.The result is as shown in table 6, add above-mentioned antioxidant and can reduce the POV value that bakes cake, the POV value is 0.319g/100g in the blank sample, bake cake POV value behind the interpolation mass fraction 0.02%TBHQ and reduce to 0.227g/100g, bake cake POV value behind the interpolation mass fraction 0.02%OTP and reduce to 0.253g/100g, add mass fraction 0.02% embodiment 2, embodiment 3 and embodiment 4AOB-o sample and can be down to 0.191g/100g with baking cake POV value, 0.188g/100g and 0.181g/100g, effect is better than TBHQ and OTP.
The different antioxidants of table 6 are on the impact of cake peroxide value
| Group | POV value (g/100g) |
| Blank | 0.319±0.015 |
| 0.02%TBHQ | 0.227±0.009 |
| 0.02%OTP | 0.253±0.013 |
| The AOB-o of 0.02 |
0.191±0.008 |
| The AOB-o of 0.02% embodiment 3 | 0.188±0.009 |
| The AOB-o of 0.02% embodiment 4 | 0.181±0.011 |
Comparative Examples 1 ~ Comparative Examples 2
Change the AOB-w among the embodiment 2: fat acyl chloride: the mol ratio of catalyst, and reaction time and reaction temperature, all the other are equal to embodiment 2; Thereby obtain accordingly Comparative Examples 1 ~ Comparative Examples 2.Specifically as shown in table 7.
The preparation parameter of table 7 Comparative Examples 1 ~ Comparative Examples 2
The AOB-o of above-mentioned Comparative Examples 1 ~ Comparative Examples 2 gained is carried out every detection according to embodiment 6 ~ embodiment 11 described methods, and acquired results is as shown in table 8 below.
Table 8 Comparative Examples 1 ~ Comparative Examples 2 preparation and AOB-o Performance Ratio
At last, it is also to be noted that, what more than enumerate only is several specific embodiments of the present invention.Obviously, the invention is not restricted to above embodiment, many distortion can also be arranged.All distortion that those of ordinary skill in the art can directly derive or associate from content disclosed by the invention all should be thought protection scope of the present invention.
Claims (10)
1. fat-soluble AOB AOB-o is characterized in that: total phenol content 〉=20%, p-Coumaric Acid content 〉=0.5%, the solubility in ethyl acetate 〉=3%, yellowish-brown or yellowish-brown powder, slightly ester flavor; Can directly be dissolved in edible oil and fat, middle LCFA and the non-polar solven, show good anti peroxidation of lipid performance and heat endurance; And the formation of the rich amyloid Assessments of Acrylamide Generated in Heated Foodstuffs of energy establishment, can in food industry, use as oil antioxidant and acrylic amide restrainer simultaneously.
2. fat-soluble AOB AOB-o according to claim 1, it is characterized in that: take water-soluble AOB AOB-w as raw material, with Powdered, graininess or Formulation that the fat acyl chloride ester exchange forms, dissolve in edible oil and fat and/or in, become liquid formulation in the LCFA.
3. according to claim 1 or 2 described fat-soluble AOB AOB-o, it is characterized in that: the infrared transmission spectra behind pressing potassium bromide troche all is presented at 1700 cm
-1Near strong carbonyl absorption peak is arranged, and 3400 cm
-1Near hydroxyl absworption peak significantly weakens than AOB-w.
4. the preparation method of a fat-soluble AOB AOB-o is characterized in that may further comprise the steps:
1), in the low polar solvent I, under the effect of base catalyst, water-soluble AOB AOB-w and fat acyl chloride are in 30 ℃ ~ 50 ℃ acylation reaction 5 h ~ 10 h; Water-soluble AOB AOB-w: fat acyl chloride: the mol ratio of base catalyst is 1:0.5 ~ 2.5:0.8 ~ 3;
2), the pH value of step 1) gained product is transferred to neutrality, vibration evenly, standing demix; Get the organic phase on upper strata, the washing final vacuum is concentrated, gets fat-soluble AOB AOB-o crude product.
5. the preparation method of fat-soluble AOB AOB-o according to claim 4 is characterized in that: fat-soluble AOB AOB-o crude product is made with extra care:
After fat-soluble AOB AOB-o crude product volumetric concentration was the dissolving of 85% ~ 92% ethanol-water solution, with the extraction of low polar solvent II, then concentrated, drying got fat-soluble AOB AOB-o.
6. according to claim 4 or the preparation method of 5 described fat-soluble AOB AOB-o, it is characterized in that: the base catalyst in the described step 1) is sodium acetate, sodium acid carbonate or triethylamine.
7. the preparation method of fat-soluble AOB AOB-o according to claim 6 is characterized in that: described fat acyl chloride is the fat acyl chloride that forms after the aliphatic acid of C8 ~ C18 chain length and the acylating reagent acidylate.
8. the preparation method of fat-soluble AOB AOB-o according to claim 7 is characterized in that:
The aliphatic acid of described C8 ~ C18 chain length is sad, capric acid, palmitic acid, laurate, cinnamic acid or stearic acid;
Described acylating reagent is nitrosyl chloride, chlorosulfuric acid, phosphoryl chloride phosphorus oxychloride or thionyl chloride.
9. the preparation method of fat-soluble AOB AOB-o according to claim 8 is characterized in that:
In the described step 1): the low polar solvent I is ethyl acetate, n-hexane, benzene or acetone, and the amount ratio of described water-soluble AOB AOB-w and low polar solvent I is 1 g:25 ~ 125 mL;
Described step 2) in: the watery hydrochloric acid take concentration as 0.8 ~ 1.2 mol/L, dilute sulfuric acid or rare nitric acid regulating step 1) the pH value of gained product transfers 7.0 ± 0.5.
10. the preparation method of fat-soluble AOB AOB-o according to claim 9 is characterized in that:
In the step that described AOB-o crude product is made with extra care, the low polar solvent II is benzinum, ether or n-hexane.
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