CN106977416B - A kind of method of quick preparation high-purity hydroxyl-alpha-sanshool - Google Patents
A kind of method of quick preparation high-purity hydroxyl-alpha-sanshool Download PDFInfo
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- CN106977416B CN106977416B CN201710278494.3A CN201710278494A CN106977416B CN 106977416 B CN106977416 B CN 106977416B CN 201710278494 A CN201710278494 A CN 201710278494A CN 106977416 B CN106977416 B CN 106977416B
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- LHFKHAVGGJJQFF-UHFFFAOYSA-N hydroxyl-alpha-sanshool Natural products CC=CC=CC=CCCC=CC(=O)NCC(C)(C)O LHFKHAVGGJJQFF-UHFFFAOYSA-N 0.000 title claims abstract description 40
- 238000000034 method Methods 0.000 title claims abstract description 29
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims abstract description 24
- 238000000605 extraction Methods 0.000 claims abstract description 16
- 239000007788 liquid Substances 0.000 claims abstract description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 60
- 241000949456 Zanthoxylum Species 0.000 claims description 16
- 239000000341 volatile oil Substances 0.000 claims description 14
- 239000000287 crude extract Substances 0.000 claims description 12
- 239000006228 supernatant Substances 0.000 claims description 12
- 238000001035 drying Methods 0.000 claims description 10
- 239000003921 oil Substances 0.000 claims description 8
- 238000002604 ultrasonography Methods 0.000 claims description 7
- 238000005119 centrifugation Methods 0.000 claims description 6
- 239000000706 filtrate Substances 0.000 claims description 6
- 210000002966 serum Anatomy 0.000 claims description 6
- 230000009514 concussion Effects 0.000 claims description 4
- 239000002994 raw material Substances 0.000 claims description 4
- 230000006837 decompression Effects 0.000 claims 2
- 241001079064 Zanthoxylum schinifolium Species 0.000 claims 1
- 238000005374 membrane filtration Methods 0.000 claims 1
- 229920001144 Hydroxy alpha sanshool Polymers 0.000 abstract description 15
- 238000004128 high performance liquid chromatography Methods 0.000 abstract description 9
- 230000010355 oscillation Effects 0.000 abstract description 7
- 238000004440 column chromatography Methods 0.000 abstract description 3
- 238000002474 experimental method Methods 0.000 abstract description 3
- LHFKHAVGGJJQFF-UEOYEZOQSA-N Hydroxy-alpha-sanshool Chemical compound C\C=C\C=C\C=C/CC\C=C\C(=O)NCC(C)(C)O LHFKHAVGGJJQFF-UEOYEZOQSA-N 0.000 abstract 2
- 239000000126 substance Substances 0.000 description 13
- PSKIOIDCXFHNJA-UHFFFAOYSA-N Sanshool Natural products CC=CC=CC=CCCC=CC=CC(=O)NC(C)C PSKIOIDCXFHNJA-UHFFFAOYSA-N 0.000 description 10
- 244000089698 Zanthoxylum simulans Species 0.000 description 10
- SBXYHCVXUCYYJT-UEOYEZOQSA-N alpha-Sanshool Chemical compound C\C=C\C=C\C=C/CC\C=C\C(=O)NCC(C)C SBXYHCVXUCYYJT-UEOYEZOQSA-N 0.000 description 7
- 235000019640 taste Nutrition 0.000 description 7
- 239000012528 membrane Substances 0.000 description 5
- 150000001408 amides Chemical class 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- KVUKDCFEXVWYBN-UHFFFAOYSA-N gamma-sanshooel Natural products CC=CC=CC=CCCC=CC=CC(=O)NCC(C)C KVUKDCFEXVWYBN-UHFFFAOYSA-N 0.000 description 4
- KVUKDCFEXVWYBN-JDXPBYPHSA-N gamma-sanshool Chemical compound C\C=C\C=C\C=C/CC\C=C\C=C\C(=O)NCC(C)C KVUKDCFEXVWYBN-JDXPBYPHSA-N 0.000 description 4
- 238000002386 leaching Methods 0.000 description 4
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 4
- LHFKHAVGGJJQFF-UMYNZBAMSA-N (2e,6e,8e,10e)-n-(2-hydroxy-2-methylpropyl)dodeca-2,6,8,10-tetraenamide Chemical compound C\C=C\C=C\C=C\CC\C=C\C(=O)NCC(C)(C)O LHFKHAVGGJJQFF-UMYNZBAMSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 235000002566 Capsicum Nutrition 0.000 description 3
- 239000006002 Pepper Substances 0.000 description 3
- 241000722363 Piper Species 0.000 description 3
- 235000016761 Piper aduncum Nutrition 0.000 description 3
- 235000017804 Piper guineense Nutrition 0.000 description 3
- 235000008184 Piper nigrum Nutrition 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 2
- SBXYHCVXUCYYJT-UMYNZBAMSA-N beta-sanshool Chemical compound C\C=C\C=C\C=C\CC\C=C\C(=O)NCC(C)C SBXYHCVXUCYYJT-UMYNZBAMSA-N 0.000 description 2
- 239000008157 edible vegetable oil Substances 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 235000019634 flavors Nutrition 0.000 description 2
- -1 hydroxyl-γ-sanshool Chemical compound 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 235000008534 Capsicum annuum var annuum Nutrition 0.000 description 1
- 240000008384 Capsicum annuum var. annuum Species 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 235000019604 hot taste sensations Nutrition 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 239000008601 oleoresin Substances 0.000 description 1
- 238000011017 operating method Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000004153 renaturation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 239000002195 soluble material Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- 238000000825 ultraviolet detection Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/22—Separation; Purification; Stabilisation; Use of additives
- C07C231/24—Separation; Purification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicines Containing Plant Substances (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
Abstract
本发明公开了一种快速制备高纯度羟基‑α‑山椒素的方法，采用恒温振荡提取、正己烷萃取以及紫外照射处理三个关键步骤，此外该制备方法不需要特殊的仪器设备，如制备型或半制备型高效液相色谱仪，使得制备方法相比于传统的柱层析法更加简单、耗时更短、成本低，因此可以为一般的实验室和一般操作水平的人员用来制备高纯度的羟基‑α‑山椒素以进行其所需实验，极大的提高了工作效率。
The invention discloses a method for rapidly preparing high-purity hydroxy-α-sanshool, which adopts three key steps of constant temperature oscillation extraction, n-hexane extraction and ultraviolet irradiation treatment. Or semi-preparative high-performance liquid chromatograph, which makes the preparation method simpler, less time-consuming and lower in cost than traditional column chromatography, so it can be used by general laboratories and general operating level personnel to prepare high-performance liquid chromatography. Purity of hydroxy-α-sanshool to carry out the required experiments, which greatly improves the work efficiency.
Description
Technical field
The present invention relates to Separation of Natural Products purification arts, and in particular to a kind of quickly preparation high-purity hydroxyl-alpha-Chinese pepper
The method of element.
Background technique
Zanthoxylum essential oil is directly to impregnate Chinese prickly ash with edible oil or using organic solvent extraction, supercritical CO2The methods of extraction system
The xanthoxylum oleoresin obtained mixes the made flavored oils with spicy hot taste with appropriate amount of edible oil.The processing of Zanthoxylum essential oil greatly reduces
Chinese prickly ash causes the loss and microbial contamination of effective component in the links such as storing and selling, and solves pepper grain and zanthoxylum powder
Agent is inconvenient therefore more and more popular with consumers to culinary art and edible bring.But current Zanthoxylum essential oil market and lack of standardization, product
Label only indicates raw material mostly, and the spicy components content as Zanthoxylum essential oil important indicator does not appear on label.How
High-purity numb-taste components are isolated, the heat as the quantitative standard items of the numb taste of Chinese prickly ash and products thereof to be always studies in China
Point and each Chinese prickly ash manufacturing enterprise focus of attention.
In the application of Chinese prickly ash, most important is still its flavor, the strong numb taste as caused by how unsaturated amide
It is the important quality indicator that Chinese prickly ash can become one of Chinese " eight big tastes ".Numb taste in Chinese prickly ash is by amide substance (numb taste object
Matter) caused by, research shows that these substances include γ-sanshool, hydroxyl-γ-sanshool, β-sanshool, hydroxy-beta-Chinese pepper
Element, γ-sanshool, hydroxyl-γ-sanshool, hydroxyl-ε-sanshool, hydroxyl-γ-different sanshool, xanthoxlin, different xanthoxlin etc..
Sanshool can be divided into α-sanshool, β-sanshool, γ-sanshool, hydroxyl-alpha-sanshool, hydroxy-beta-sanshool, hydroxyl-again
γ-sanshool, hydroxyl-ε-sanshool etc., and hydroxyl-alpha-sanshool therein and hydroxyl-γ-sanshool relative amount are obvious
Greater than other sanshools.These sanshools have UV absorption phenomenon in 200nm to 300nm, and occur most at 270nm
Big absorption peak.
From Chinese prickly ash extracting and developing, purifying obtains the amide substance of high-purity is a kind of extremely difficult method.
03132341.3 discloses a kind of technique using supercritical fluid technique separation Chinese prickly ash spicy component, the process equipment manipulation skill
Art is more demanding, and prepared spicy component is preliminary extract, and such methods need stronger operating experience, the weight of experiment
Renaturation is very poor, and unstable result, time-consuming, and prepared spicy component is preliminary extract, is only used for industrialized production
In, as the raw material of food and drug, it is not suitable for the standard items quantitative as numb taste.And 201210175527.9 use thin layer
The method that analysis method extracts high-purity hydroxyl sanshool from Zanthoxylum essential oil, although having filled up the blank of this respect, in preparation process
Still the chromatographic column of liquid chromatogram is used, preparation cost increases.
In view of the above-mentioned problems, the present invention is extracted using constant temperature oscillation, n-hexane extraction and ultraviolet irradiation three-step approach are to flower
Hydroxyl-alpha-sanshool in green pepper oil extracts, and furthermore the preparation method does not need special instrument and equipment, so that preparation method
It is simpler compared to traditional column chromatography, time-consuming shorter, at low cost, greatly improve working efficiency.
Summary of the invention
The shortcomings that in order to overcome the prior art, the technical solution of the present invention is to provide a kind of quick preparation high-purity hydroxyls
Base-α-sanshool method.This method is easy to operate, does not need professional too strong technical staff and operates, expends simultaneously
Time is obviously shortened, and without using preparative or semipreparative high performance liquid chromatography instrument in manufacturing process, reduces preparation cost,
And hydroxyl-alpha-sanshool the purity is high obtained.
In order to achieve the above object, the invention adopts the following technical scheme:
A kind of method of quick preparation high-purity hydroxyl-alpha-sanshool, comprising the following steps:
(1) using Zanthoxylum essential oil as raw material, methanol is added into Zanthoxylum essential oil, is then successively shaken, ultrasound, centrifugation, is obtained
Take supernatant；
(2) n-hexane is added into supernatant to be extracted, obtains subnatant；
(3) subnatant chromatographed, filtered, filtrate is finally subjected to evaporated under reduced pressure, obtain crude extract；
(4) it after crude extract being dissolved in methanol, is transferred in serum bottle and carries out ultraviolet light irradiation, subtracted after irradiation
Pressure is evaporated up to hydroxyl-alpha-sanshool.
Further, the volume ratio of Zanthoxylum essential oil and methanol is 1:20 in the step (1) of the present invention；The Zanthoxylum essential oil is red
Zanthoxylum essential oil.It is shaken in step (1) using isothermal vibration device, temperature is 40 DEG C, and the concussion time is 1h, revolving speed 160rpm.Step
(1) ultrasonic time is 5min in.Centrifugal speed is 4000r/min, centrifugation time 15min in step (1).The upper step
(2) the solid-liquid ratio 1:2 of supernatant and n-hexane in, extraction times 3 times；The step (2) is filtered into 0.22 μm of organic system filter membrane
Filtering.Step (3) evaporated under reduced pressure uses Rotary Evaporators evaporated under reduced pressure, and drying condition is vacuum degree 0.09Mpa, and temperature is
45 DEG C, drying time 2h.Methanol is hplc grade methanol, dosage 20ml in the step (4).The ultraviolet lamp power be 20 ~
30w, wavelength 254nm, the distance of irradiation are 15 ~ 20cm, and the time of irradiation is 2 ~ 4h.Step (4) evaporated under reduced pressure uses
Rotary Evaporators evaporated under reduced pressure, drying condition are vacuum degree 0.09Mpa, and temperature is 45 DEG C, drying time 1h.
Present inventive concept are as follows: the present invention uses methanol to extract the sanshool in Zanthoxylum essential oil first, carries out after extraction
Concussion, ultrasound, centrifugation, grease and oil soluble material are removed.Extraction 3 times is repeated using n-hexane, by the flavor in Chinese prickly ash
Matter all removes, and to obtain the spicy components (sanshool) of high-purity, is then chromatographed, is filtered, being evaporated to obtain coarse extraction
Object.Finally sanshool is dissolved using methanol, provides polar environment for sanshool, and obtains purity after ultraviolet light and is greater than
The content of 98% hydroxyl-alpha-sanshool, impurity and other isomers and other amide substances is less than 1%.Such purity
Hydroxyl-alpha-sanshool can be used for all bio-chemical characteristics and numb taste evaluation experimental, the entire preparation method used time is 7 ~ 9
A hour.
Compared with the prior art, the invention has the following advantages:
1, present invention employs constant temperature oscillations to extract, n-hexane extraction and ultraviolet irradiation handle three key steps, makes
It is simpler compared to traditional column chromatography, time-consuming shorter to obtain preparation method, traditional extraction separation and purification method generally consumes
When 24 ~ 48 hours, and complicated for operation, empirical relatively strong, less reproducible, method overall process provided by the invention only needs 7 ~ 9
A hour, and it is easy to operate.And in patent No. CN201210309645.4 in step (1) drying time just up to 0.5 ~ 2h, step
(3) drying time also up to 2~6h, not only prompts operating procedure more, more complicated in, and the time spent is longer, and to operation
The requirement of personnel is higher, once there is residual solvent, then will affect the extraction of next step.
2, since present invention employs ultraviolet irradiations to handle, using light reaction and chemical reaction so that hydroxyl-alpha-sanshool
Isomer hydroxy-beta-sanshool and hydroxyl-ε-sanshool converted to its (hydroxyl-alpha-sanshool), and then improve
Hydroxyl-alpha-sanshool purity, finally makes the purity of target substance (hydroxyl-alpha-sanshool) to reach 98% or more.It is much high
In the concentration of the extracted hydroxyl-alpha-sanshool 82.82% of patent No. CN201210175527.9.
3, since quickly preparation high-purity hydroxyl-alpha-sanshool method does not need special instrument to one kind provided by the invention
Device equipment, such as preparative or semipreparative high performance liquid chromatography instrument, and it is easy to operate, it is time-consuming short, it is at low cost, therefore can be one
As laboratory and the personnel of general operation level be used to prepare hydroxyl-alpha-sanshool of high-purity to carry out experiment needed for it,
Greatly improve working efficiency.
Detailed description of the invention
Substance HPLC map prepared by Fig. 1 embodiment 1；
Substance HPLC map prepared by Fig. 2 embodiment 2；
Substance HPLC map prepared by Fig. 3 embodiment 3.
Specific embodiment
The present invention is specifically described below by embodiment, it is necessary to which indicated herein is that following embodiment is only used
In invention is further explained, it should not be understood as limiting the scope of the invention.The people that is skilled in technique in the field
Member can make some nonessential modifications and adaptations to the present invention according to the content of aforementioned present invention.
Embodiment 1
(1) 30 mL pericarpium zanthoxyli bungeani oil are taken, methanol is added in 1:20 by volume, uses 40 DEG C of oscillation 1h of constant temperature oscillator, revolving speed
Leaching liquor is moved into centrifuge tube after 4000 r/min are centrifuged 15 min and takes supernatant by 160 rpm, then 5 min of ultrasound；
(2) supernatant is extracted, solid-liquid ratio 1:2 with n-hexane, is extracted 3 times, by the subnatant parlkaline of extraction
Aluminum oxide column, gained chromatographic solution cross 0.22 μm of organic system filter membrane, finally by filtrate 45 DEG C of (vacuum degrees of Rotary Evaporators
0.09Mpa) evaporated under reduced pressure 2h obtains crude extract；
(3) it takes 10mg crude extract to be dissolved in 20mL hplc grade methanol, is put into serum bottle, carried out at ultraviolet irradiation
Reason, ultraviolet irradiation condition are ultraviolet lamp power 20w, and ultraviolet wavelength 254nm, article is apart from ultraviolet lamp 15cm, irradiation time
It is 2 hours, with 45 DEG C of (vacuum degree 0.09Mpa) evaporated under reduced pressure 1h of Rotary Evaporators up to hydroxyl-alpha-sanshool after irradiation.
Embodiment 2
(1) 30 mL pericarpium zanthoxyli bungeani oil are taken, methanol is added in 1:20 by volume, uses 40 DEG C of oscillation 1h of constant temperature oscillator, revolving speed
Leaching liquor is moved into centrifuge tube after 4000 r/min are centrifuged 15 min and takes supernatant by 160 rpm, then 5 min of ultrasound；
(2) supernatant is extracted, solid-liquid ratio 1:2 with n-hexane, is extracted 3 times, by the subnatant parlkaline of extraction
Aluminum oxide column, gained chromatographic solution cross 0.22 μm of organic system filter membrane, finally by filtrate 45 DEG C of (vacuum degrees of Rotary Evaporators
0.09Mpa) evaporated under reduced pressure 2h obtains crude extract；
(3) it takes 10mg crude extract to be dissolved in 20mL hplc grade methanol, is put into serum bottle, carried out at ultraviolet irradiation
Reason, ultraviolet irradiation condition are ultraviolet lamp power 30w, and ultraviolet wavelength 254nm, article is apart from ultraviolet lamp 20cm, irradiation time
It is 4 hours, with 45 DEG C of (vacuum degree 0.09Mpa) evaporated under reduced pressure 1h of Rotary Evaporators up to hydroxyl-alpha-sanshool after irradiation.
Embodiment 2
(1) 30 mL pericarpium zanthoxyli bungeani oil are taken, methanol is added in 1:20 by volume, uses 40 DEG C of oscillation 1h of constant temperature oscillator, revolving speed
Leaching liquor is moved into centrifuge tube after 4000 r/min are centrifuged 15 min and takes supernatant by 160 rpm, then 5 min of ultrasound；
(2) supernatant is extracted, solid-liquid ratio 1:2 with n-hexane, is extracted 3 times, by the subnatant parlkaline of extraction
Aluminum oxide column, gained chromatographic solution cross 0.22 μm of organic system filter membrane, finally by filtrate 45 DEG C of (vacuum degrees of Rotary Evaporators
0.09Mpa) evaporated under reduced pressure 2h obtains crude extract；
(3) it takes 10mg crude extract to be dissolved in 20mL hplc grade methanol, is put into serum bottle, carried out at ultraviolet irradiation
Reason, ultraviolet irradiation condition are ultraviolet lamp power 25w, and ultraviolet wavelength 254nm, article is apart from ultraviolet lamp 18cm, irradiation time
It is 3 hours, with 45 DEG C of (vacuum degree 0.09Mpa) evaporated under reduced pressure 1h of Rotary Evaporators up to hydroxyl-alpha-sanshool after irradiation.
Test case 1
(1) take 30mL pericarpium zanthoxyli bungeani oily, methanol is added in 1:20 by volume, uses 40 DEG C of oscillation 1h of constant temperature oscillator, revolving speed
Leaching liquor is moved into centrifuge tube and takes supernatant after 4000r/min centrifugation 15min by 160rpm, then 5 min of ultrasound；
(2) supernatant is extracted, solid-liquid ratio 1:2 with n-hexane, is extracted 3 times, by the subnatant parlkaline of extraction
Aluminum oxide column, gained chromatographic solution cross 0.22 μm of organic system filter membrane, finally by filtrate 45 DEG C of (vacuum degrees of Rotary Evaporators
0.09Mpa) evaporated under reduced pressure 2h obtains crude extract；
(3) it takes 10mg crude extract to be dissolved in 20mL hplc grade methanol, is put into serum bottle, to after reaction, with rotation
45 DEG C of (vacuum degree 0.09Mpa) evaporated under reduced pressure of evaporimeter, being evaporated time 1h can be obtained hydroxyl-alpha-sanshool.
Test case 2
The above-mentioned substance being prepared is subjected to spectral detection, is detected, is examined using high performance liquid chromatography (HPLC)
Survey condition is chromatographic column: 1100-5 C18 column of MN Nucleodur (4 × 125 mm, 5 μm)；Mobile phase: A water；B
Acetonitrile；Flow velocity: 0.5 mL/min；Column temperature: 25 DEG C；Ultraviolet detection wavelength: 270 nm；Sample volume: 20 μ L.Elution program such as table 1
It is shown.
1 HPLC elution program of table
According to HPLC analysis as a result, as shown in Figure 1, hydroxyl-alpha-sanshool purity in the substance that embodiment 1 is prepared
It is 98.07%.As shown in Fig. 2, hydroxyl-alpha-sanshool purity is 98.20% in the substance that embodiment 2 is prepared.Such as Fig. 3 institute
Show, hydroxyl-alpha-sanshool purity is 98.21% in the substance that embodiment 3 is prepared.In the substance that test case 1 is prepared
Hydroxyl-alpha-sanshool is 72%, and hydroxy-beta-sanshool is 9%, and hydroxyl-ε-sanshool is 4%.
Claims (9)
1. a kind of quickly prepare hydroxyl-alpha-sanshool method, which is characterized in that should the preparation method is as follows:
(1) using Zanthoxylum essential oil as raw material, methanol is added into Zanthoxylum essential oil, is then successively shaken, ultrasound, centrifugation, in acquisition
Clear liquid；
(2) n-hexane is added into supernatant to be extracted, obtains subnatant；
(3) subnatant chromatographed, filtered, filtrate is finally subjected to evaporated under reduced pressure, obtain crude extract；
(4) it after crude extract being dissolved in methanol, being transferred in serum bottle and carries out ultraviolet light irradiation, the ultraviolet lamp power is 20 ~
30w, wavelength 254nm, the distance of irradiation are 15 ~ 20cm, and the time of irradiation is 2 ~ 4h, and evaporated under reduced pressure is carried out after irradiation and is
Obtain hydroxyl-alpha-sanshool.
2. according to claim 1 prepare hydroxyl-alpha-sanshool method, it is characterised in that: Chinese prickly ash in the step (1)
The volume ratio of oil and methanol is 1:20；The Zanthoxylum essential oil is pericarpium zanthoxyli bungeani oil.
3. according to claim 1 prepare hydroxyl-alpha-sanshool method, it is characterised in that: use constant temperature in step (1)
Oscillator concussion, temperature are 40 DEG C, and the concussion time is 1h, revolving speed 160rpm.
4. according to claim 1 prepare hydroxyl-alpha-sanshool method, it is characterised in that: ultrasonic time in step (1)
For 5min.
5. according to claim 1 prepare hydroxyl-alpha-sanshool method, it is characterised in that: centrifugal speed in step (1)
For 4000r/min, centrifugation time 15min.
6. according to claim 1 prepare hydroxyl-alpha-sanshool method, it is characterised in that: in the upper step (2)
The solid-liquid ratio 1:2 of clear liquid and n-hexane, extraction times 3 times；0.22 μm of organic system membrane filtration is filtered into the step (3).
7. according to claim 1 prepare hydroxyl-alpha-sanshool method, it is characterised in that: step (3) decompression is steamed
Dry to use Rotary Evaporators evaporated under reduced pressure, drying condition is vacuum degree 0.09Mpa, and temperature is 45 DEG C, drying time 2h.
8. according to claim 1 prepare hydroxyl-alpha-sanshool method, it is characterised in that: methanol in the step (4)
For hplc grade methanol, dosage 20ml.
9. according to claim 1 prepare hydroxyl-alpha-sanshool method, it is characterised in that: step (4) decompression is steamed
Dry to use Rotary Evaporators evaporated under reduced pressure, drying condition is vacuum degree 0.09Mpa, and temperature is 45 DEG C, drying time 1h.
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| CN109824538B (en) * | 2019-03-06 | 2021-10-08 | 四川大学 | Extraction of typical amides from Zanthoxylum bungeanum based on deep eutectic solvent |
| CN112321450B (en) * | 2020-10-23 | 2021-09-10 | 西南交通大学 | Preparation method of hydroxyl-alpha-sanshool monomer |
| CN117618405A (en) * | 2021-08-25 | 2024-03-01 | 沈阳药科大学 | Method for rapidly extracting different sanshool monomers |
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|---|---|---|---|---|
| WO2013135511A1 (en) * | 2012-03-12 | 2013-09-19 | Imax Discovery Gmbh | N-(2,4-dimethylpentan-3-yl)-methylbenzamides and their use as flavoring agents |
| CN102690208B (en) * | 2012-05-31 | 2014-04-16 | 四川大学 | Method for extracting hydroxyl sanshool from zanthoxylum oil |
| CN104030937A (en) * | 2014-06-16 | 2014-09-10 | 中华全国供销合作总社南京野生植物综合利用研究所 | Method for quickly preparing high-content zanthoxylum unsaturated amide components |
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