CN105418713B - A kind of method of the amino-acid modified sojasterol of water-soluble alec - Google Patents
A kind of method of the amino-acid modified sojasterol of water-soluble alec Download PDFInfo
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- CN105418713B CN105418713B CN201510952358.9A CN201510952358A CN105418713B CN 105418713 B CN105418713 B CN 105418713B CN 201510952358 A CN201510952358 A CN 201510952358A CN 105418713 B CN105418713 B CN 105418713B
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- water
- sojasterol
- alec
- sterol
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- 150000001413 amino acids Chemical class 0.000 title claims abstract description 13
- 238000000034 method Methods 0.000 title claims abstract description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 28
- 238000006243 chemical reaction Methods 0.000 claims abstract description 27
- OILXMJHPFNGGTO-UHFFFAOYSA-N (22E)-(24xi)-24-methylcholesta-5,22-dien-3beta-ol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)C=CC(C)C(C)C)C1(C)CC2 OILXMJHPFNGGTO-UHFFFAOYSA-N 0.000 claims abstract description 21
- OQMZNAMGEHIHNN-UHFFFAOYSA-N 7-Dehydrostigmasterol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)C=CC(CC)C(C)C)CCC33)C)C3=CC=C21 OQMZNAMGEHIHNN-UHFFFAOYSA-N 0.000 claims abstract description 21
- HZYXFRGVBOPPNZ-UHFFFAOYSA-N UNPD88870 Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)=CCC(CC)C(C)C)C1(C)CC2 HZYXFRGVBOPPNZ-UHFFFAOYSA-N 0.000 claims abstract description 21
- LGJMUZUPVCAVPU-UHFFFAOYSA-N beta-Sitostanol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(CC)C(C)C)C1(C)CC2 LGJMUZUPVCAVPU-UHFFFAOYSA-N 0.000 claims abstract description 21
- HCXVJBMSMIARIN-PHZDYDNGSA-N stigmasterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)/C=C/[C@@H](CC)C(C)C)[C@@]1(C)CC2 HCXVJBMSMIARIN-PHZDYDNGSA-N 0.000 claims abstract description 21
- 235000016831 stigmasterol Nutrition 0.000 claims abstract description 21
- 229940032091 stigmasterol Drugs 0.000 claims abstract description 21
- BFDNMXAIBMJLBB-UHFFFAOYSA-N stigmasterol Natural products CCC(C=CC(C)C1CCCC2C3CC=C4CC(O)CCC4(C)C3CCC12C)C(C)C BFDNMXAIBMJLBB-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000003054 catalyst Substances 0.000 claims abstract description 17
- 244000068988 Glycine max Species 0.000 claims abstract description 11
- 235000010469 Glycine max Nutrition 0.000 claims abstract description 11
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical compound O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000002360 preparation method Methods 0.000 claims abstract description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 36
- 238000003756 stirring Methods 0.000 claims description 25
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 18
- 239000012065 filter cake Substances 0.000 claims description 18
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 12
- 239000011521 glass Substances 0.000 claims description 12
- 239000006228 supernatant Substances 0.000 claims description 12
- 239000003921 oil Substances 0.000 claims description 11
- 235000019198 oils Nutrition 0.000 claims description 11
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 claims description 10
- 238000002156 mixing Methods 0.000 claims description 10
- 239000007788 liquid Substances 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 238000004458 analytical method Methods 0.000 claims description 7
- 238000002425 crystallisation Methods 0.000 claims description 7
- 230000008025 crystallization Effects 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- RCEAADKTGXTDOA-UHFFFAOYSA-N OS(O)(=O)=O.CCCCCCCCCCCC[Na] Chemical compound OS(O)(=O)=O.CCCCCCCCCCCC[Na] RCEAADKTGXTDOA-UHFFFAOYSA-N 0.000 claims description 6
- 238000004332 deodorization Methods 0.000 claims description 6
- 239000012153 distilled water Substances 0.000 claims description 6
- 239000000706 filtrate Substances 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 6
- 239000012467 final product Substances 0.000 claims description 6
- 238000000227 grinding Methods 0.000 claims description 6
- 239000005457 ice water Substances 0.000 claims description 6
- 238000009413 insulation Methods 0.000 claims description 6
- 238000000874 microwave-assisted extraction Methods 0.000 claims description 6
- 239000004570 mortar (masonry) Substances 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 239000003549 soybean oil Substances 0.000 claims description 6
- 235000012424 soybean oil Nutrition 0.000 claims description 6
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims description 6
- 230000010355 oscillation Effects 0.000 claims description 5
- 238000010898 silica gel chromatography Methods 0.000 claims description 5
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical class OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 4
- 238000010792 warming Methods 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 3
- 239000003517 fume Substances 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- 235000019441 ethanol Nutrition 0.000 claims 2
- 150000003431 steroids Chemical class 0.000 claims 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims 1
- 244000046052 Phaseolus vulgaris Species 0.000 claims 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 claims 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 229930182558 Sterol Natural products 0.000 abstract description 18
- 150000003432 sterols Chemical class 0.000 abstract description 18
- 235000003702 sterols Nutrition 0.000 abstract description 18
- 235000013305 food Nutrition 0.000 abstract description 8
- 239000006227 byproduct Substances 0.000 abstract description 4
- 230000032050 esterification Effects 0.000 abstract description 4
- 238000005886 esterification reaction Methods 0.000 abstract description 4
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 abstract description 2
- 239000000047 product Substances 0.000 abstract description 2
- 235000013361 beverage Nutrition 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 239000000839 emulsion Substances 0.000 description 7
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 6
- 238000005516 engineering process Methods 0.000 description 6
- 230000005855 radiation Effects 0.000 description 5
- 235000019483 Peanut oil Nutrition 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 4
- 239000000312 peanut oil Substances 0.000 description 4
- 239000003643 water by type Substances 0.000 description 4
- 235000012000 cholesterol Nutrition 0.000 description 3
- 125000005456 glyceride group Chemical group 0.000 description 3
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 229920002892 amber Polymers 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000009423 ventilation Methods 0.000 description 2
- MTJGVAJYTOXFJH-UHFFFAOYSA-N 3-aminonaphthalene-1,5-disulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 MTJGVAJYTOXFJH-UHFFFAOYSA-N 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 125000003275 alpha amino acid group Chemical group 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 230000000767 anti-ulcer Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- 235000014121 butter Nutrition 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000007385 chemical modification Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- NXMUXTAGFPJGTQ-UHFFFAOYSA-N decanoic acid;octanoic acid Chemical compound CCCCCCCC(O)=O.CCCCCCCCCC(O)=O NXMUXTAGFPJGTQ-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000003324 growth hormone secretagogue Substances 0.000 description 1
- 235000013310 margarine Nutrition 0.000 description 1
- 239000003264 margarine Substances 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 235000013622 meat product Nutrition 0.000 description 1
- 230000000050 nutritive effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 150000005691 triesters Chemical class 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
- 238000002137 ultrasound extraction Methods 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 238000009941 weaving Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
-
- 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
- A23L2/38—Other non-alcoholic beverages
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Nutrition Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Abstract
The invention discloses a kind of method of the water-soluble amino-acid modified sojasterol of alec, belong to the modified field of sterol.The present invention uses multistage microwave amplifier sterol from soybean, and catalyst is obtained, sterol and succinyl oxide are carried out into esterification, carried out esterification products and be modified with the caviar rich in amino acid again, you can obtain the sterol of good water solubility, modified soybean sterol of the invention is due to improving the water-insoluble of script stigmasterol containing hydrophilic radical, can apply in the food of water-based, and the catalyst green non-pollution added in modified-reaction, byproduct of reaction is few, and preparation cost is cheap.
Description
Technical field
The invention discloses a kind of method of the water-soluble amino-acid modified sojasterol of alec, belong to the modified field of sterol.
Background technology
Sterol, is obtained by physical purification from corn and soybean, with being of high nutritive value, the features such as physiologically active is strong.
Phytosterol can reduce the risk of cardiovascular disease by reducing cholesterol.It is widely used in food, medicine, cosmetics, animal
The field such as growth stimulator and sheet processing, printing, weaving, it is particularly very universal as food additives in Europe.Phytosterol
It is primarily present in vegetable fat part, it is possible to use the difference in terms of raw material composition and physicochemical property, extracts phytosterol
Material.Common extracting method has：Solvent crystallization, saponification method, complexometry, enzyme process, supercritical CO2Extraction, microwave radiation technology
Extraction method and ultrasound assisted extraction method etc..
Phytosterol have reduce cholesterol, anti-inflammatory, bring down a fever, antiulcer, the effect such as antitumor and antibacterial.Phytosterol is
A kind of structure and the biochemical characteristic sterols material similar to cholesterol.This " class fat " be widely present in the root of plant, stem,
In leaf and fruit, can not synthesize in human body, unique approach is by meal ingestion.It is widely used in medical science, industry, day
Change, agricultural, are a kind of Multipurpose pure crudes.The current application of sterol and its derivative in food focuses mostly in edible
In the fat-soluble food products such as oil, butter, margarine, meat products, there is certain oil-soluble mainly due to phytosterol, and
What most phytosterol derivatives improved is the lipophile of phytosterol, and the water-insoluble of phytosterol, cause its
Water-based food, using being also very limited, therefore, the water solubility for improving phytosterol is very necessary.
The content of the invention
Present invention mainly solves technical problem：Water-insoluble and low oil-soluble for current phytosterol, cause it
In water-based food, using being also very limited, and chemical modification catalyst toxicity is larger, big for environment pollution, reaction
Temperature is high, the problem more than byproduct of reaction, there is provided a kind of preparation method of the water-soluble amino-acid modified sojasterol of alec, this
Multistage microwave amplifier sterol is used in invention from soybean, and catalyst is obtained, and sterol and succinyl oxide carried out into esterification, then with richness
Caviar containing amino acid carries out esterification products and is modified, you can obtain the sterol of good water solubility, modified soybean of the invention
Sterol can be applied in the food of water-based due to improving the water-insoluble of script stigmasterol containing hydrophilic radical,
And the catalyst green non-pollution added in modified-reaction, byproduct of reaction is few, and preparation cost is cheap.
In order to solve the above-mentioned technical problem, the technical solution adopted in the present invention is：
(1) 300~500g soybean oils processing deodorization distillate is taken, is 3 by solid-to-liquid ratio:1 in distillate add by mole
Than being 1:1 mixing absolute ethyl alcohol and toluene, be put into Microwave Extraction instrument, with the power of 600W 0.2~0.3MPa pressure
After lower microwave radiation technology reacts 2~3min, it is put into refrigerator, it is 4~6 DEG C to set temperature, filters thick after 5~6h of ice analysis crystallization
Stigmasterol；
(2) weigh 30~35g thick stigmasterol obtained above and pour into 250mL burnings together with 100~150mL cyclohexanone
In cup, 55~65 DEG C are heated in immigration water-bath, be placed on homogenizer, stirred with the rotating speed of 800~900r/min
Until after thick stigmasterol is completely dissolved, making it naturally cool to room temperature and being filtrated to get filter cake, then filter cake is pressed into above-mentioned steps
Drying is standby to constant weight during baking oven is put into after operating 3~5 times repeatedly；
(3) take 3~5g lauryl sodium sulfate to be put into mortar, the concentration for adding 2~3 times of its volume is 0.01mol/L
Hydrochloric acid solution, be put into Muffle furnace after grinding 3~5min in the fume hood, 1~2h is calcined at 300~400 DEG C and is obtained 12
Alkylsurfuric acid catalyst；
(4) take 30~50g Leishans alec to be put into 500mL beakers, add the steaming that 200~300mL temperature is 40~50 DEG C
Distilled water, is put into sonic oscillation instrument after being stirred with glass bar, after vibrating 30~40min with the power ultrasonic of 200~300W
It is put into screw centrifuge, separating removal filter residue with the 10~20min of rotating speed centrifugal treating of 7000~8000r/min obtains supernatant
Liquid；
(5) it is in molar ratio 1 by standby filter cake and succinyl oxide:1.5 mixed after be dissolved in both gross masses 2~3
In toluene again, 110~120 DEG C are heated in immigration oil bath pan, reaction solution is crossed silica gel column chromatography by 10~20h of insulation reaction
Obtain sojasterol monomester succinate；
(6) it is 2 by 400~500mL volume ratios:1 dichloromethane and acetonitrile mixture is fitted into conical flask with cover, then adds
Enter dodecyl sulphate catalyst obtained in 2~5g, move into ice-water bath, 40~50g sojasterol ambers are added at 2~4 DEG C
Amber acid monoester, is slowly stirred with glass bar and instills the supernatant that 30~50mL is centrifugally separating to obtain points for 3~5 times under stirring
Liquid, control rate of addition makes completion of dropping in its 30~35min, and after continuing to stir 5~10min, filtering removes filter residue by filtrate
It is put into rotary evaporator, is warming up to 85~95 DEG C, it is amino-acid modified big to obtain final product a kind of water-soluble alec after revolving removal solvent
Stigmasterol.
Application process of the invention：The obtained modified soybean sterol of 20~30mL present invention is taken in 500ml containers, then is added
Enter 5~10mL peanut oil, 3~5mL Glycerin, mixed triester with caprylic acid capric acid, mixing is heated to 100~120 DEG C, and the clear solution of formation is
Oil phase, then be poured into the reaction vessel of 1L, and 100~150mL deionized waters are added thereto to, it is heated to 80~82
DEG C, to stir 15~25min under 5000~6000r/min rotating speeds, after stirring gained emulsion high pressure homogenizer with 4000~
The pressure treatment of 4500psi 1~3 time, 20~25 DEG C are cooled to after treatment by emulsion, afterwards by the 0.6 of water-based beverage gross weight
~1% is added in beverage, you can the water-based beverage for planting sojasterol is obtained.
The beneficial effects of the invention are as follows：
(1) modified soybean sterol of the invention improves the water-insoluble of script stigmasterol, can apply in water-based
In food；
(2) the catalyst green non-pollution that the present invention is added, byproduct of reaction is few, and preparation cost is cheap.
Specific embodiment
300~500g soybean oils processing deodorization distillate is taken first, is 3 by solid-to-liquid ratio:1 in distillate add by mole
Than being 1:1 mixing absolute ethyl alcohol and toluene, be put into Microwave Extraction instrument, with the power of 600W 0.2~0.3MPa pressure
After lower microwave radiation technology reacts 2~3min, it is put into refrigerator, it is 4~6 DEG C to set temperature, filters thick after 5~6h of ice analysis crystallization
Stigmasterol；Weigh 30~35g thick stigmasterol obtained above and pour into 250mL beakers together with 100~150mL cyclohexanone
In, 55~65 DEG C are heated in immigration water-bath, it is placed on homogenizer, it is straight with the rotating speed stirring of 800~900r/min
After being completely dissolved to thick stigmasterol, it is naturally cooled to room temperature and be filtrated to get filter cake, then filter cake is anti-by above-mentioned steps
Drying is standby to constant weight during baking oven is put into after operating 3~5 times again；Take 3~5g lauryl sodium sulfate to be put into mortar, add
The concentration of 2~3 times of its volume is the hydrochloric acid solution of 0.01mol/L, and Muffle furnace is put into after grinding 3~5min in fume hood,
1~2h is calcined at 300~400 DEG C dodecyl sulphate catalyst is obtained；30~50g Leishans alec is taken to be put into 500mL beakers,
The distilled water for adding 200~300mL temperature to be 40~50 DEG C, is put into sonic oscillation instrument, with 200 after being stirred with glass bar
The power ultrasonic of~300W is put into screw centrifuge after vibrating 30~40min, at the rotating speed centrifugation of 7000~8000r/min
10~20min of reason separates removal filter residue and obtains supernatant；It is in molar ratio 1 by standby filter cake and succinyl oxide:1.5 are mixed
It is dissolved in afterwards in the toluene of 2~3 times of both gross masses, moves into and be heated to 110~120 DEG C in oil bath pan, 10~20h of insulation reaction,
Reaction solution is crossed into silica gel column chromatography and obtains sojasterol monomester succinate；It is 2 by 400~500mL volume ratios:1 dichloromethane
It is fitted into conical flask with cover with acetonitrile mixture, adds dodecyl sulphate catalyst obtained in 2~5g, moves into ice-water bath
In, 40~50g sojasterol monomester succinates are added at 2~4 DEG C, it is slowly stirred with glass bar and points 3 under stirring
Instill the supernatant that 30~50mL is centrifugally separating to obtain for~5 times, control rate of addition makes completion of dropping in its 30~35min, after
After 5~10min of continuous stirring, be put into filtrate in rotary evaporator by filtering removal filter residue, is warming up to 85~95 DEG C, and revolving removal is molten
A kind of amino-acid modified sojasterol of water-soluble alec is obtained final product after agent.
Example 1
300g soybean oils processing deodorization distillate is taken first, is 3 by solid-to-liquid ratio:1 is in molar ratio to being added in distillate
1:1 mixing absolute ethyl alcohol and toluene, be put into Microwave Extraction instrument, with the power of 600W under the pressure of 0.2MPa microwave radiation technology
After reaction 2min, it is put into refrigerator, it is 4 DEG C to set temperature, thick stigmasterol is filtered to obtain after ice analysis crystallization 5h；Weigh 30g above-mentioned
Obtained thick stigmasterol is poured into 250mL beakers together with 100mL cyclohexanone, and 55 DEG C are heated in immigration water-bath, is put
Put on homogenizer, with the rotating speed stirring of 800r/min until after thick stigmasterol is completely dissolved, naturally cooling to it
Room temperature is simultaneously filtrated to get filter cake, then is put into after filter cake is operated into 3 times repeatedly by above-mentioned steps in baking oven and dries to constant weight, standby；
Take 3g lauryl sodium sulfate to be put into mortar, the concentration of 2 times of its volume is added for the hydrochloric acid solution of 0.01mol/L, in ventilation
Muffle furnace is put into after grinding 3min in cupboard, 1h is calcined at 300 DEG C dodecyl sulphate catalyst is obtained；Take 30g Leishans alec
It is put into 500mL beakers, the distilled water for adding 200mL temperature to be 40 DEG C is put into sonic oscillation instrument after being stirred with glass bar
In, to be put into screw centrifuge after the power ultrasonic vibration 30min of 200W, with the rotating speed centrifugal treating 10min of 7000r/min
Separate removal filter residue and obtain supernatant；It is in molar ratio 1 by standby filter cake and succinyl oxide:1.5 mixed after be dissolved in both
In the toluene that 2 times of gross mass, 110 DEG C are heated in immigration oil bath pan, reaction solution is crossed silica gel column chromatography and obtained by insulation reaction 10h
To sojasterol monomester succinate；It is 2 by 400mL volume ratios:1 dichloromethane and acetonitrile mixture loads conical flask with cover
In, dodecyl sulphate catalyst obtained in 2g is added, move into ice-water bath, 40g sojasterol butanedioic acids are added at 2 DEG C
Monoesters, is slowly stirred with glass bar and instills the supernatant that 30mL is centrifugally separating to obtain points for 3 times under stirring, and control is added dropwise
Speed makes completion of dropping in its 30min, and after continuing to stir 5min, be put into filtrate in rotary evaporator by filtering removal filter residue, rises
Temperature obtains final product a kind of amino-acid modified sojasterol of water-soluble alec to 85 DEG C after revolving removal solvent.
The obtained modified soybean sterol of the 20mL present invention is taken in 500ml containers, the pungent capric acid of 5mL peanut oil, 3mL is added
Glyceride, mixing is heated to 100 DEG C, and the clear solution of formation is oil phase, then is poured into the reaction vessel of 1L, and
100mL deionized waters are added thereto to, 80 DEG C are heated to, to stir 15min under 5000r/min rotating speeds, gained emulsion after stirring
With high pressure homogenizer with the pressure treatment 1 time of 4000psi, emulsion is cooled to 20 DEG C after treatment, afterwards by water-based beverage gross weight
The 0.6% of amount is added in beverage, you can the water-based beverage for planting sojasterol is obtained.
Example 2
400g soybean oils processing deodorization distillate is taken first, is 3 by solid-to-liquid ratio:1 is in molar ratio to being added in distillate
1:The absolute ethyl alcohol and toluene of 1 mixing, are put into Microwave Extraction instrument, and with the power of 600W, microwave is auxiliary under the pressure of 0.25MPa
After helping reaction 2min, it is put into refrigerator, it is 5 DEG C to set temperature, thick stigmasterol is filtered to obtain after ice analysis crystallization 5.5h；Weigh 33g
Thick stigmasterol obtained above is poured into 250mL beakers together with 125mL cyclohexanone, and 60 are heated in immigration water-bath
DEG C, it is placed on homogenizer, with the rotating speed stirring of 850r/min until after thick stigmasterol is completely dissolved, making it naturally cold
But to room temperature and filter cake is filtrated to get, then is put into after filter cake is operated into 4 times repeatedly by above-mentioned steps in baking oven and dries to constant weight, it is standby
With；Take 4g lauryl sodium sulfate to be put into mortar, the concentration of 2 times of its volume is added for the hydrochloric acid solution of 0.01mol/L, logical
Muffle furnace is put into after grinding 4min in wind cupboard, 1.5h is calcined at 350 DEG C dodecyl sulphate catalyst is obtained；Take 40g Leishans
Alec is put into 500mL beakers, the distilled water for adding 250mL temperature to be 45 DEG C, is put into ultrasound after being stirred with glass bar and is shaken
Swing in instrument, be put into screw centrifuge after vibrating 35min with the power ultrasonic of 250W, with the rotating speed centrifugal treating of 7500r/min
15min separates removal filter residue and obtains supernatant；It is in molar ratio 1 by standby filter cake and succinyl oxide:1.5 mixed after be dissolved in
In the toluene of both 2 times of gross masses, 115 DEG C are heated in immigration oil bath pan, reaction solution is crossed silica gel column layer by insulation reaction 15h
Analysis obtains sojasterol monomester succinate；It is 2 by 450mL volume ratios:1 dichloromethane and acetonitrile mixture loads tool plug taper
In bottle, dodecyl sulphate catalyst obtained in 4g is added, moved into ice-water bath, 45g sojasterol ambers are added at 3 DEG C
Acid monoester, is slowly stirred with glass bar and instills the supernatant that 40mL is centrifugally separating to obtain, control drop points for 4 times under stirring
Acceleration makes completion of dropping in its 33min, and after continuing to stir 8min, be put into filtrate in rotary evaporator by filtering removal filter residue,
90 DEG C are warming up to, a kind of amino-acid modified sojasterol of water-soluble alec is obtained final product after revolving removal solvent.
The obtained modified soybean sterol of the 25mL present invention is taken in 500ml containers, the pungent capric acid of 8mL peanut oil, 4mL is added
Glyceride, mixing is heated to 110 DEG C, and the clear solution of formation is oil phase, then is poured into the reaction vessel of 1L, and
125mL deionized waters are added thereto to, 81 DEG C are heated to, to stir 20min under 5500r/min rotating speeds, gained emulsion after stirring
With high pressure homogenizer with the pressure treatment 2 times of 4250psi, emulsion is cooled to 23 DEG C after treatment, afterwards by water-based beverage gross weight
The 0.8% of amount is added in beverage, you can the water-based beverage for planting sojasterol is obtained.
Example 3
500g soybean oils processing deodorization distillate is taken first, is 3 by solid-to-liquid ratio:1 is in molar ratio to being added in distillate
1:1 mixing absolute ethyl alcohol and toluene, be put into Microwave Extraction instrument, with the power of 600W under the pressure of 0.3MPa microwave radiation technology
After reaction 3min, it is put into refrigerator, it is 6 DEG C to set temperature, thick stigmasterol is filtered to obtain after ice analysis crystallization 6h；Weigh 35g above-mentioned
Obtained thick stigmasterol is poured into 250mL beakers together with 150mL cyclohexanone, and 65 DEG C are heated in immigration water-bath, is put
Put on homogenizer, with the rotating speed stirring of 900r/min until after thick stigmasterol is completely dissolved, naturally cooling to it
Room temperature is simultaneously filtrated to get filter cake, then is put into after filter cake is operated into 5 times repeatedly by above-mentioned steps in baking oven and dries to constant weight, standby；
Take 5g lauryl sodium sulfate to be put into mortar, the concentration of 3 times of its volume is added for the hydrochloric acid solution of 0.01mol/L, in ventilation
Muffle furnace is put into after grinding 5min in cupboard, 2h is calcined at 400 DEG C dodecyl sulphate catalyst is obtained；Take 50g Leishans alec
It is put into 500mL beakers, the distilled water for adding 300mL temperature to be 50 DEG C is put into sonic oscillation instrument after being stirred with glass bar
In, to be put into screw centrifuge after the power ultrasonic vibration 40min of 300W, with the rotating speed centrifugal treating 20min of 8000r/min
Separate removal filter residue and obtain supernatant；It is in molar ratio 1 by standby filter cake and succinyl oxide:1.5 mixed after be dissolved in both
In the toluene that 3 times of gross mass, 120 DEG C are heated in immigration oil bath pan, reaction solution is crossed silica gel column chromatography and obtained by insulation reaction 20h
To sojasterol monomester succinate；It is 2 by 500mL volume ratios:1 dichloromethane and acetonitrile mixture loads conical flask with cover
In, dodecyl sulphate catalyst obtained in 5g is added, move into ice-water bath, 50g sojasterol butanedioic acids are added at 4 DEG C
Monoesters, is slowly stirred with glass bar and instills the supernatant that 50mL is centrifugally separating to obtain points for 5 times under stirring, and control is added dropwise
Speed makes completion of dropping in its 35min, and after continuing to stir 10min, be put into filtrate in rotary evaporator by filtering removal filter residue, rises
Temperature obtains final product a kind of amino-acid modified sojasterol of water-soluble alec to 95 DEG C after revolving removal solvent.
The obtained modified soybean sterol of the 30mL present invention is taken in 500ml containers, 10mL peanut oil, the 5mL pungent last of the ten Heavenly stems is added
Acid glyceride, mixing is heated to 120 DEG C, and the clear solution of formation is oil phase, then is poured into the reaction vessel of 1L,
And 150mL deionized waters are added thereto to, and 82 DEG C are heated to, to stir 25min under 6000r/min rotating speeds, gained breast after stirring
Emulsion is cooled to 25 DEG C by liquid high pressure homogenizer with the pressure treatment 3 times of 4500psi after treatment, total by water-based beverage afterwards
The 1% of weight is added in beverage, you can the water-based beverage for planting sojasterol is obtained.
Claims (1)
1. a kind of method of the amino-acid modified sojasterol of water-soluble alec, it is characterised in that specific preparation process is：
(1) 300~500g soybean oils processing deodorization distillate is taken, is 3 by solid-to-liquid ratio:1 is in molar ratio to being added in distillate
1:The absolute ethyl alcohol and toluene of 1 mixing, are put into Microwave Extraction instrument, micro- under the pressure of 0.2~0.3MPa with the power of 600W
After 2~3min of ripple assisted reaction, it is put into refrigerator, it is 4~6 DEG C to set temperature, thick beans steroid is filtered to obtain after 5~6h of ice analysis crystallization
Alcohol；
(2) weigh 30~35g thick stigmasterol obtained above and pour into 250mL beakers together with 100~150mL cyclohexanone
In, 55~65 DEG C are heated in immigration water-bath, it is placed on homogenizer, it is straight with the rotating speed stirring of 800~900r/min
After being completely dissolved to thick stigmasterol, it is naturally cooled to room temperature and be filtrated to get filter cake, then filter cake is anti-by above-mentioned steps
Drying is standby to constant weight during baking oven is put into after operating 3~5 times again；
(3) take 3~5g lauryl sodium sulfate to be put into mortar, add the concentration of 2~3 times of its volume for the salt of 0.01mol/L
Acid solution, Muffle furnace is put into after grinding 3~5min in fume hood, 1~2h is calcined at 300~400 DEG C dodecyl is obtained
Sulfuric acid catalyst；
(4) take 30~50g Leishans alec to be put into 500mL beakers, add the distilled water that 200~300mL temperature is 40~50 DEG C,
It is put into after being stirred with glass bar in sonic oscillation instrument, spiral shell is put into after vibrating 30~40min with the power ultrasonic of 200~300W
In whiz scheming, removal filter residue is separated with the 10~20min of rotating speed centrifugal treating of 7000~8000r/min and obtains supernatant；
(5) it is in molar ratio 1 by standby filter cake and succinyl oxide:1.5 mixed after be dissolved in 2~3 times of both gross masses
In toluene, 110~120 DEG C are heated in immigration oil bath pan, reaction solution is crossed silica gel column chromatography and obtained by 10~20h of insulation reaction
Sojasterol monomester succinate；
(6) it is 2 by 400~500mL volume ratios:1 dichloromethane and acetonitrile mixture is fitted into conical flask with cover, adds 2
Dodecyl sulphate catalyst obtained in~5g, is moved into ice-water bath, and 40~50g sojasterol butanedioic acids are added at 2~4 DEG C
Monoesters, is slowly stirred with glass bar and instills the supernatant that 30~50mL is centrifugally separating to obtain points for 3~5 times under stirring,
Control rate of addition makes completion of dropping in its 30~35min, and after continuing to stir 5~10min, be put into for filtrate by filtering removal filter residue
In rotary evaporator, 85~95 DEG C are warming up to, a kind of amino-acid modified soybean steroid of water-soluble alec is obtained final product after revolving removal solvent
Alcohol.
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