CN105111055B - A kind of method that natural parahydroxyben-zaldehyde is prepared from bamboo shoots - Google Patents
A kind of method that natural parahydroxyben-zaldehyde is prepared from bamboo shoots Download PDFInfo
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- CN105111055B CN105111055B CN201510607938.4A CN201510607938A CN105111055B CN 105111055 B CN105111055 B CN 105111055B CN 201510607938 A CN201510607938 A CN 201510607938A CN 105111055 B CN105111055 B CN 105111055B
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- parahydroxyben
- zaldehyde
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Abstract
The invention discloses a kind of method that natural parahydroxyben-zaldehyde is prepared from bamboo shoots, bamboo shoots crushing is extracted with alcohol reflux, the extract solution after ethanol is reclaimed to be adsorbed with macroporous absorbent resin, eluted using ethanol solution, chloroform, ethyl acetate or extracting n-butyl alcohol are used after eluent concentration, silica gel mixed sample is added after concentration to dry, upper prop, column chromatography is carried out by mobile phase of the mixed solution of petroleum ether and acetone or ethyl acetate, collect eluent containing target component, recycling design it is dry parahydroxyben-zaldehyde crude product, recrystallization, obtain the sterling of parahydroxyben-zaldehyde；The inventive method is without using organic solvents such as acid or alkali, and preparation process is environmentally safe, and technique is simple and with low cost, and product yield is high, is adapted to industrialization production.
Description
Technical field
The invention belongs to day biological technical field, more particularly to a kind of side that natural parahydroxyben-zaldehyde is prepared from bamboo shoots
Method.
Background technology
Bamboo shoots are the tender stems of grass family perennial plant bamboo, from ancient times referred to as " treasure in dish ", edible existing in China
The history of more than 2500 years.Bamboo shoots are fresh and tender, and meat is crisp, and delicious flavour is nutritious, are a kind of low sugar, low fat, the day of high protein
Right functional food.The main function of bamboo shoots at edible aspect, in addition, bamboo shoots also in the form of extract in food, drink, guarantor
It is strong（Function）It is used widely in the field such as food, natural drug and food additives and cosmetic additive agent.On bamboo shoots
Extraction separation, Structural Identification and the bioactivity research of chemical composition show that parahydroxyben-zaldehyde is the main component of bamboo shoots
One of, and show strong tyrosinase, it is rightγ- aminobutyric acid (GABA) transaminase and succinic semialdehyde dehydrogenase (
SSADH) inhibitory action.In addition, parahydroxyben-zaldehyde has good bacteriostasis, be usually used in food, cosmetics, medicine it is anti-
In terms of rotten, mould proof and sterilization.
Parahydroxyben-zaldehyde is the intermediate of a kind of important medicine, agricultural chemicals, dyestuff, spices and food feed additive,
With the fast development of China's medicine, agricultural chemicals and perfume industry, domestic, parahydroxyben-zaldehyde consumption figure rapid growth has much out
Hair prospect.Contain active aldehyde radical and phenolic hydroxyl group in its molecular structure, show special reactivity, synthesis can be extended many
Plant functional compounds.In terms of medicine, available for cardiovascular medicament esmolol, oral antibiotic oxyammonia benzylpenicillin
(Amoxicillin) and the synthesis of antibacterial trimethoprim (TMP) trimethoprim；In terms of agricultural chemicals, parahydroxyben-zaldehyde is main
Synthesis as herbicide Brominal and dichlobenil.In terms of spices, available for synthesis anisaldehyde, vanillic aldehyde, syringaldehyde, foreign jasmine
Many rare spices such as jasmine and raspberry ketone.Parahydroxyben-zaldehyde manufactures NAB National Association 0f Broadcasters as U.S.'s flavorant（FEMA）、(FAO/
WHO) the flavorant that the combination food additive Committee of Experts passes through, the addition scope in food is respectively 1~30 mg/
kg。
Antioxidant is an important component of food additives, can prevent food composition from causing change because of oxidation
Matter, in order to improve the oxidation resistance of food, often in food processing, storage, preservation process addition antioxidant, is used at present
More than comparing is artificial synthesized antioxidant, such as butylated hydroxy anisole synthetized oxidation preventive agent, such as butylated hydroxy anisole（BHA)
, dibutyl hydroxy toluene (BHT), propylgallate (PG) and tert-butylhydroquinone (TBHQ), but toxicity test shows,
Synthetized oxidation preventive agent has certain toxicity and carcinogenesis, and increasing country starts to limit or prohibits the use of some synthesis
Antioxidant.Therefore, the development trend that synthetized oxidation preventive agent is food industry from now on, exploitation safety are replaced with natural
Nontoxic, natural, efficient natural by be antioxidant research developing direction.
Research of the present invention to the chemical composition of bamboo shoots, extracts main component there is provided the preparation technology of parahydroxyben-zaldehyde,
The yield and purity for extracting parahydroxyben-zaldehyde are very high, and technique is simple and with low cost, and then enter industrialized production, satisfaction pair
The wilderness demand of hydroxy benzaldehyde commercially, is with a wide range of applications.
The content of the invention
It is an object of the invention to provide a kind of method that parahydroxyben-zaldehyde is extracted from bamboo shoots, applicant has to bamboo shoots
The research for imitating composition provides the technique for extracting parahydroxyben-zaldehyde, and operating procedure is few, and purity is high, is adapted to large-scale production.
Bamboo kind raw material available for the present invention is not particularly limited, and can be the bamboo not belonged to together, preferably Dendrocalamus
Bamboo shoots based on, such as imperial pearl, sinocalamus latiflorus, mangosteen.Bamboo shoots can be that bamboo shoots meat can also be bamboo shoots complete stool, can also be the useless of bamboo shoots
Gurry such as bamboo shoot head and bamboo shoot shell etc..
The method that the present invention prepares natural parahydroxyben-zaldehyde from bamboo shoots, comprises the following steps：
（1）Bamboo shoots are crushed, flowed back with the ethanol solution of 5~10 times of mass percent concentration 50~90% of bamboo shoots quality
Extract, flow back 2~3 hours every time, filtering, merging filtrate；
（2）By step（1）Filtrate is concentrated into after no ethanol, is separated precipitation, is obtained solution；
（3）By step（2）Solution is adsorbed with macroporous resin column, is eluted with the ethanol solution of mass percent concentration 40~90%,
The eluent containing target component is collected, no ethanol is concentrated into and obtains concentrate；Target product is determined using thin-layer chromatography；
（4）Concentrate carries out extraction 2~4 times using chloroform, ethyl acetate or n-butanol, and combining extraction liquid is concentrated to give leaching
Cream, admixes the silica gel of 1.5 times of medicinal extract quality, mixes sample silica gel and carries out conventional drying, is then loaded to silicagel column and is eluted；
（5）Eluted, collected as mobile phase using petroleum ether-acetone mixture or petroleum ether-ethyl acetate mixed liquor
After eluent containing target component, recycling design, parahydroxyben-zaldehyde crude product is obtained；
（6）By step（5）Parahydroxyben-zaldehyde crude product is recrystallized in organic solvent, and crystallographic is obtained after drying
Parahydroxyben-zaldehyde.
The step（2）Be separated into conventional centrifugation.
The step（3）It is to be completed on the conventional macroporous absorbent resin of prior art, macroporous absorbent resin is clear with ethanol
Also reusable after washing, macroporous absorbent resin is D-101, AB-8, HZ-816 or HP-20.
The step（4）In to mix sample and silica gel for chromatography be 100~300 mesh column layer chromatography silicone rubbers.
The step（5）Petrochina ether-acetone mixture be petroleum ether and acetone by volume the ︰ 1 of 8 ︰ 1~6 ratio mix
Close and be made；Petroleum ether-ethyl acetate mixed liquor is the ratio mixing system of petroleum ether and ethyl acetate by volume for the ︰ 1 of 6 ︰ 1~3
.
The step（6）Recrystallization solvent be petroleum ether and acetone by volume 1:The solution of 2 ratios mixing.
The present invention has following advantages and effect：Natural parahydroxyben-zaldehyde is prepared using such scheme, without using acid
Or the organic solvent such as alkali, preparation process is environmentally safe and with low cost, and product yield is high, is adapted to industrialization production.
Embodiment
The present invention is described in further detail below by embodiment, but protection scope of the present invention be not limited to it is described
Content.
Embodiment 1
Take fresh Dendrocalamus sinicus（Dendrocalamus sinicus）Bamboo shoots 5kg, with 25kg mass percent concentration
80% alcohol reflux is extracted 3 times, and 3 hours every time, filtering, merging filtrate, filtrate was reduced to after no ethanol, and precipitation is gone in centrifugation,
Obtain solution；Solution is added in macroreticular resin D-101 posts and adsorbed, after 3 times of water elutions, using the second of mass percent concentration 80%
Alcoholic solution is eluted, and is collected the eluent containing target component, is concentrated into no ethanol and obtains concentrate；Concentrate is extracted using chloroform
3 times, combining extraction liquid is concentrated to give medicinal extract, admixes 100 mesh column layer chromatography silicone rubbers of 1.5 times of medicinal extract quality, mixes sample silica gel and carries out often
Drying is advised, silicagel column is then loaded to and is eluted；With petroleum ether and the mixed liquor of acetone（Petroleum ether and acetone 6 ︰ by volume
1 ratio is mixed to prepare）Eluted, collect after the eluent containing target component, recycling design, obtain parahydroxyben-zaldehyde thick
Product；In petroleum ether-acetone mixture（Petroleum ether and acetone by volume 1:The solution of 2 ratios mixing）It is middle to be recrystallized, obtain
7.8g parahydroxyben-zaldehyde products, are detected through high-efficient liquid phase technique, and purity is up to 98%.
Obtained parahydroxyben-zaldehyde is subjected to detection instrument and condition：
Instrument：PE Series 200LC；Detector：PE Series 200 UV/VIS Detector；Chromatographic software：PE
The TCWS chromatographic work stations of Series 200；
Chromatographic condition：Chromatographic column：Diamonsil C18 posts（5 μm, 4.6mm × 250mm）；Mobile phase：The phosphorus of acetonitrile -0.1%
Aqueous acid（%~50% of 15min gradeds 10）；Detection wavelength：230 nm；Flow velocity：1.0 mL/min；Column temperature：30 ℃.
Embodiment 2
Take fresh Dendrocalamus sinicus（Dendrocalamus sinicus）Bamboo shoots 5kg, with 35kg mass percent concentration
70% alcohol reflux is extracted 2 times, and 3 hours every time, filtering, merging filtrate, filtrate was reduced to after no ethanol, and precipitation is gone in centrifugation,
Obtain solution；Solution is added in macroreticular resin AB-8 posts and adsorbed, after 2 times of water elutions, using the ethanol of mass percent concentration 80%
Solution is eluted, and is collected the eluent containing target component, is concentrated into no ethanol and obtains concentrate；Concentrate is extracted using ethyl acetate
Take 2 times, combining extraction liquid is concentrated to give medicinal extract, admix 200 mesh column layer chromatography silicone rubbers of 1.5 times of medicinal extract quality, mix the progress of sample silica gel
Conventional drying, is then loaded to normal phase silicagel column and is eluted；With petroleum ether and the mixed liquor of ethyl acetate（Petroleum ether and acetic acid
Ethyl ester 4 ︰ 1 by volume ratio is mixed to prepare）Eluted, collect the eluent containing target component, after recycling design, obtained pair
Hydroxy benzaldehyde crude product；In petroleum ether-acetone mixture（Petroleum ether and acetone by volume 1:The solution of 2 ratios mixing）In enter
Row recrystallization, obtains 6.9g parahydroxyben-zaldehyde products, is detected through high-efficient liquid phase technique, purity ＞ 98%.
Embodiment 3
Take fresh Dendrocalamus sinicus（Dendrocalamus sinicus）Bamboo shoots 5kg, with 40kg mass percent concentration
90% alcohol reflux is extracted 3 times, and 2 hours every time, filtering, merging filtrate, filtrate was reduced to after no ethanol, and precipitation is gone in centrifugation,
Obtain solution；Solution is added in macroreticular resin HZ-816 posts and adsorbed, after 3 times of water elutions, using the second of mass percent concentration 85%
Alcoholic solution is eluted, and is collected the eluent containing target component, is concentrated into no ethanol and obtains concentrate；Concentrate is extracted using chloroform
4 times, combining extraction liquid is concentrated to give medicinal extract, admixes 300 mesh column layer chromatography silicone rubbers of 1.5 times of medicinal extract quality, mixes sample silica gel and carries out often
Drying is advised, normal phase silicagel column is then loaded to and is eluted；With petroleum ether and the mixed liquor of acetone（Petroleum ether and acetone press volume
Ratio than 8 ︰ 1 is mixed to prepare）Eluted, collect after the eluent containing target component, recycling design, obtain parahydroxyben-zaldehyde
Crude product；In petroleum ether-acetone mixture（Petroleum ether and acetone by volume 1:The solution of 2 ratios mixing）It is middle to be recrystallized,
7.6 g parahydroxyben-zaldehyde products are obtained, are detected through high-efficient liquid phase technique, purity ＞ 98%.
Embodiment 4
Take fresh Dendrocalamus sinicus（Dendrocalamus sinicus）Bamboo shoots 5kg, with 50kg mass percent concentration
50% alcohol reflux is extracted 3 times, and 3 hours every time, filtering, merging filtrate, filtrate was reduced to after no ethanol, and precipitation is gone in centrifugation,
Obtain solution；Solution is added in macroreticular resin HP-20 posts and adsorbed, after 3 times of water elutions, using the second of mass percent concentration 60%
Alcoholic solution is eluted, and is collected the eluent containing target component, is concentrated into no ethanol and obtains concentrate；Concentrate is extracted using n-butanol
Take 2 times, combining extraction liquid is concentrated to give medicinal extract, admix 200 mesh column layer chromatography silicone rubbers of 1.5 times of medicinal extract quality, mix the progress of sample silica gel
Conventional drying, is then loaded to normal phase silicagel column and is eluted；With petroleum ether and the mixed liquor of ethyl acetate（Petroleum ether and acetic acid
Ethyl ester 6 ︰ 1 by volume ratio is mixed to prepare）Eluted, collect the eluent containing target component, after recycling design, obtained pair
Hydroxy benzaldehyde crude product；In petroleum ether-acetone mixture（Petroleum ether and acetone by volume 1:The solution of 2 ratios mixing）In enter
Row recrystallization, obtains 6.6g parahydroxyben-zaldehyde products, is detected through high-efficient liquid phase technique, purity ＞ 98%.
Embodiment 5
Take fresh Dendrocalamus sinicus（Dendrocalamus sinicus）Bamboo shoots 5kg, with 30kg mass percent concentration
60% alcohol reflux is extracted 3 times, and 3 hours every time, filtering, merging filtrate, filtrate was reduced to after no ethanol, and precipitation is gone in centrifugation,
Obtain solution；Solution is added in macroreticular resin HP-20 posts and adsorbed, after 3 times of water elutions, using the second of mass percent concentration 45%
Alcoholic solution is eluted, and is collected the eluent containing target component, is concentrated into no ethanol and obtains concentrate；Concentrate is extracted using n-butanol
Take 2 times, combining extraction liquid is concentrated to give medicinal extract, admix 300 mesh column layer chromatography silicone rubbers of 1.5 times of medicinal extract quality, mix the progress of sample silica gel
Conventional drying, is then loaded to normal phase silicagel column and is eluted；With petroleum ether and the mixed liquor of ethyl acetate（Petroleum ether and acetic acid
Ethyl ester 3 ︰ 1 by volume ratio is mixed to prepare）Eluted, collect the eluent containing target component, after recycling design, obtained pair
Hydroxy benzaldehyde crude product；In petroleum ether-acetone mixture（Petroleum ether and acetone by volume 1:The solution of 2 ratios mixing）In enter
Row recrystallization, obtains 6.8g parahydroxyben-zaldehyde products, is detected through high-efficient liquid phase technique, purity ＞ 98%.
Embodiment 6
Take fresh Dendrocalamus sinicus（Dendrocalamus sinicus）Bamboo shoots 5kg, with 50kg mass percent concentration
70% alcohol reflux is extracted 3 times, and 3 hours every time, filtering, merging filtrate, filtrate was reduced to after no ethanol, and precipitation is gone in centrifugation,
Obtain solution；Solution is added in macroreticular resin AB-8 posts and adsorbed, after 3 times of water elutions, using the ethanol of mass percent concentration 70%
Solution is eluted, and is collected the eluent containing target component, is concentrated into no ethanol and obtains concentrate；Concentrate is extracted using n-butanol
2 times, combining extraction liquid is concentrated to give medicinal extract, admixes 200 mesh column layer chromatography silicone rubbers of 1.5 times of medicinal extract quality, mixes sample silica gel and carries out often
Drying is advised, silicagel column is then loaded to and is eluted；With petroleum ether and the mixed liquor of acetone（Petroleum ether and acetone 7 ︰ by volume
1 ratio is mixed to prepare）Eluted, collect after the eluent containing target component, recycling design, obtain parahydroxyben-zaldehyde thick
Product；In petroleum ether-acetone mixture（Petroleum ether and acetone by volume 1:The solution of 2 ratios mixing）It is middle to be recrystallized, obtain
7.1g parahydroxyben-zaldehyde products, are detected through high-efficient liquid phase technique, purity ＞ 98%.
Claims (6)
1. a kind of method that natural parahydroxyben-zaldehyde is prepared from bamboo shoots, it is characterised in that following steps：
（1）Bamboo shoots are crushed, with the ethanol solution refluxing extraction of 5~10 times of mass percent concentration 50~90% of bamboo shoots quality,
Backflow 2~3 hours, are filtered, merging filtrate every time；
（2）By step（1）Filtrate is concentrated into after no ethanol, is separated precipitation, is obtained solution；
（3）By step（2）Solution is adsorbed with macroporous absorbent resin, is washed with the ethanol solution of mass percent concentration 40~90%
It is de-, the eluent containing target component is collected, no ethanol is concentrated into and obtains concentrate；
（4）Concentrate carries out extraction 2~4 times using chloroform, ethyl acetate or n-butanol, and combining extraction liquid is concentrated to give medicinal extract, mixes
Enter the silica gel of 1.5 times of medicinal extract quality, mix sample silica gel and carry out conventional drying, be then loaded to normal phase silicagel column and eluted；
（5）Eluted using petroleum ether-acetone mixture or petroleum ether-ethyl acetate mixed liquor as mobile phase, collect and contain mesh
Mark after the eluent of composition, recycling design, obtain parahydroxyben-zaldehyde crude product；
（6）By step（5）Parahydroxyben-zaldehyde crude product is recrystallized, and crystallographic obtains parahydroxyben-zaldehyde after drying；
The macroporous absorbent resin is D-101, AB-8, HZ-816 or HP-20.
2. the method that natural parahydroxyben-zaldehyde is prepared from bamboo shoots according to claim 1, it is characterised in that：It is described
（2）Step is separated into conventional centrifugation.
3. the method that natural parahydroxyben-zaldehyde is prepared from bamboo shoots according to claim 1, it is characterised in that：Step
（4）In to mix sample and silica gel for chromatography be 100~300 mesh column layer chromatography silicone rubbers.
4. the method that natural parahydroxyben-zaldehyde is prepared from bamboo shoots according to claim 3, it is characterised in that：Oil
Ether-acetone mixture is that petroleum ether and acetone ︰ 1 of 8 ︰ 1~6 by volume ratio are mixed to prepare.
5. the method that natural parahydroxyben-zaldehyde is prepared from bamboo shoots according to claim 4, it is characterised in that：Oil
Ether-ethyl acetate mixtures are that petroleum ether and ethyl acetate are mixed to prepare for the ︰ 1 of 6 ︰ 1~3 ratio by volume.
6. the method that natural parahydroxyben-zaldehyde is prepared from bamboo shoots according to claim 5, it is characterised in that：Step
（6）Recrystallization solvent for the ratios of 1 ︰ 2 mixing by volume of petroleum ether and acetone solution.
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| CN108440249A (en) * | 2018-03-14 | 2018-08-24 | 昆明理工大学 | A method of preparing natural gastrodia elata genin |
| CN109627153B (en) * | 2019-01-30 | 2021-07-27 | 桂林医学院 | Method for extracting and separating p-hydroxybenzaldehyde from nostoc commune |
| CN111393276B (en) * | 2019-06-28 | 2022-12-16 | 湖南省农产品加工研究所 | Extraction method of natural p-hydroxybenzaldehyde |
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