CN106365969A - Preparation method and application of carvone - Google Patents
Preparation method and application of carvone Download PDFInfo
- Publication number
- CN106365969A CN106365969A CN201610675900.5A CN201610675900A CN106365969A CN 106365969 A CN106365969 A CN 106365969A CN 201610675900 A CN201610675900 A CN 201610675900A CN 106365969 A CN106365969 A CN 106365969A
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- China
- Prior art keywords
- eucarvone
- extraction
- caraway oil
- preparation
- silica gel
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/79—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
Abstract
The invention relates to a preparation method for carvone and application of carvone to prevention and treatment of insects attacking stored tobacco. The preparation method provided by the invention comprises the following steps: with caraway as a raw material, extracting caraway oil at first and then separating carvone from the caraway oil. The preparation method is rich in raw materials, simple in production process and low in production cost. Carvone is applied to prevention and treatment of insects attacking stored tobacco, exerts good effect on stifling, contact killing and repelling of insects attacking stored tobacco and can be used for development of green biopesticides.
Description
Technical field
The present invention relates to Nicotiana tabacum L. insect protected drug world, more particularly, to a kind of preparation method and applications of Eucarvone.
Background technology
Nicotiana tabacum L. is subject to the infringement of insect in storage, wherein with lasioderma serricorne
(lasiodermaserricornefabricius) for sociales, red flour beetle (triboliumcastaneumherbst) it is
It is only second to the species of sociales.Estimate according to coresta, the loss that cigarette beetle is caused to storage Nicotiana tabacum L. every year is about 1%.China
Once the degree that causes harm of national stored tobacco pestses was investigated in the nineties in 20th century, the mass loss rate causing because of insect pest every year
It is about 1.64%, wherein cigarette beetle causes harm the mass loss causing much larger than other stored tobacco pestses.Conventional insect prevents tabacco barn
Control and fumigated the most generally with hydrogen phosphide (aluminum phosphate) at present, but the life-time service of hydrogen phosphide (aluminum phosphate) can be good for environment and the mankind
Kang Zaocheng necessarily affects.Thus, in April, 2010, U.S. Environmental Protection Agency (EPA) (epa) has issued aluminum phosphate and magnesium phosphide fumigant in pesticide
Using limit.Therefore, develop one kind efficiently, the compound of environmentally safe, free of contamination preventing and treating tobacco storage insect has
Important society and economic implications.
Fructus cari carvi (carumcarvi l) is the fruit of samphire caraway, is annual herb.Existing North China, west
North, Sichuan are the main place of production.There is warming middle-JIAO and strengthening the spleen, wind dispelling cold relieving, be used for controlling cold indigestion pain, cold syndrome of the stomach singultuss, lumbago, tremble with fear
Stagnant stomachache, hernia.
Content of the invention
It is an object of the invention to a kind of preparation method that Eucarvone is provided, and Eucarvone is used for preventing and treating tobacco storage
The application of insect.
A kind of preparation method of Eucarvone that the present invention provides, comprises the following steps:
Step 1) prepare caraway oil: with the Fructus cari carvi pulverized as raw material, carried using the way of distillation or supercritical extraction
Take caraway oil;
Step 2) chromatography prepares Eucarvone: be separating medium using silica gel, caraway oil and silica gel weight than for 1:5~
1:15, carries out normal-phase silica gel column chromatography, and mobile phase is the mixed liquor of normal hexane and ethyl acetate, using normal hexane: ethyl acetate
Volume ratio carries out gradient elution segmentation successively for 0:1~1:0, and 1 column volume is a stream part, obtains 10 stream part sections, stream part
Section 56, recycling design, obtain Eucarvone.
The preferred version of the present invention is, described step 1) in the way of distillation particularly as follows: the Fructus cari carvi pulverized is placed in volatilization
In oil extractor, using extraction by steam distillation 3~5h, processed with anhydrous sodium sulfate drying, obtain final product caraway oil.
Another preferred version of the present invention is, described step 1) in supercritical extraction particularly as follows: by the Tibetan pulverized fennel
Fragrant mature peel is placed in extraction kettle, extraction kettle and separating still is preheated, basin is cooled down;Open co2Gas cylinder send
Gas, and open high-pressure pump boosting;Temperature be 35~50 DEG C, pressure be 5.0~30.0mpa, co2Flow is 40~80l/h's
Under the conditions of, carry out constant temperature and pressure cycling extraction, discharging after extracting 0.5~2 hour, obtain final product caraway oil.
The present invention is preventing and treating the application in tobacco storage insect with entering to provide Eucarvone.
Described tobacco storage insect includes lasioderma serricorne, red flour beetle.
The preparation method of the present invention has the advantage that
1. simple production process, low production cost.
2. Eucarvone has fabulous fumigating, tag and repellent activity to tobacco storage insect lasioderma serricorne, red flour beetle etc., can
Prevent and treat aspect to apply in tobacco storage insect.
3. Eucarvone have efficiently, the characteristic of low toxicity, low-residual, low cost, green safety, green bio can be developed into
Pesticide.
Brief description:
Fig. 1 is Eucarvone chemical structural formula;
Fig. 2 is Eucarvone1H-nmr spectrogram;
Fig. 3 is Eucarvone13C-nmr spectrogram.
Specific embodiment
For apparent explanation goal of the invention and technical scheme, it is described in further detail by following embodiments.
Embodiment 1
1) vapor distillation preparation: take Fructus cari carvi 1.0kg, pulverize in rearmounted volatile oil extractor, using vapor distillation
Method extracts 4h, is processed with anhydrous sodium sulfate drying, obtains caraway oil 38.4ml, be stored in 4 DEG C of fresh keeping chamber of refrigerator standby.
2) supercritical co2Prepared by extraction process: take Fructus cari carvi 1.0kg, pulverize in rearmounted extraction kettle, first to extraction kettle, point
Preheated from kettle, basin is cooled down, when reaching predetermined temperature, opened co2Gas cylinder is supplied gas, and opens high-pressure pump boosting, when
When temperature, pressure reach predetermined value, start the cycle over extraction, fixedly separated pressure 10.0mpa during extraction, 40 DEG C of separation temperature, co2
Flow be 60l/h, constant temperature and pressure extract 1.5 hours after discharging, obtain caraway oil 41.0ml, be stored in 4 DEG C of fresh keeping chamber of refrigerator standby
With.
3) compound separates: Fructus cari carvi volatile oil 20ml, is separating medium using silica gel, oils and silica-gel materials weight ratio
For 1:10, through normal-phase silica gel column chromatography, mobile phase is the mixed liquor of normal hexane and ethyl acetate, using normal hexane: ethyl acetate
Volume ratio carries out gradient elution segmentation successively for 0:1~1:0, that is, initial solvent be normal hexane 100%, terminate for ethyl acetate be
100%;1 column volume is a stream part, obtains 10 stream part sections, stream part section 56, recycling design, obtains Eucarvone 7.6g.
Embodiment 2
1) vapor distillation preparation: take Fructus cari carvi 1.0kg, pulverize in rearmounted volatile oil extractor, using vapor distillation
Method extracts 5h, is processed with anhydrous sodium sulfate drying, obtains final product caraway oil 39.1ml, be stored in 4 DEG C of fresh keeping chamber of refrigerator standby.
2) supercritical co2Prepared by extraction process: take Fructus cari carvi 1.0kg, pulverize in rearmounted extraction kettle, first to extraction kettle, point
Preheated from kettle, basin is cooled down, when reaching predetermined temperature, opened co2Gas cylinder is supplied gas, and opens high-pressure pump boosting, when
When temperature, pressure reach predetermined value, start the cycle over extraction, fixedly separated pressure 5.0mpa during extraction, 35 DEG C of separation temperature, co2
Flow be 40l/h, constant temperature and pressure extract 2 hours after discharging, obtain final product caraway oil, be stored in 4 DEG C of fresh keeping chamber of refrigerator standby.
3) compound separates: Fructus cari carvi peel volatile oil 20ml, is separating medium using silica gel, oils and silica-gel materials weight
Amount ratio is 1:5, and through normal-phase silica gel column chromatography, mobile phase is the mixed liquor of normal hexane and ethyl acetate, using normal hexane: acetic acid second
Ester volume ratio carries out gradient elution segmentation successively for 0:1~1:0, and 1 column volume is a stream part, obtains 10 stream part sections, stream
Part section 56, recycling design, that is, obtain Eucarvone 7.5g.
Embodiment 3
1) vapor distillation preparation: take Fructus cari carvi 1.0kg, pulverize in rearmounted volatile oil extractor, using vapor distillation
Method extracts 3h, is processed with anhydrous sodium sulfate drying, obtains final product caraway oil 37.8ml, be stored in 4 DEG C of fresh keeping chamber of refrigerator standby.
2) supercritical co2Prepared by extraction process: take Fructus cari carvi 1.0kg, pulverize in rearmounted extraction kettle, first to extraction kettle, point
Preheated from kettle, basin is cooled down, when reaching predetermined temperature, opened co2Gas cylinder is supplied gas, and opens high-pressure pump boosting, when
When temperature, pressure reach predetermined value, start the cycle over extraction, fixedly separated pressure 30mpa during extraction, 50 DEG C of separation temperature, co2Stream
Measure as 80l/h, constant temperature and pressure extract 0.5 hour after discharging, obtain final product caraway oil, be stored in 4 DEG C of fresh keeping chamber of refrigerator standby.
3) compound separates: Fructus cari carvi peel volatile oil 20ml, is separating medium using silica gel, oils and silica-gel materials weight
Amount ratio is 1:10, and through normal-phase silica gel column chromatography, mobile phase is the mixed liquor of normal hexane and ethyl acetate, using normal hexane: acetic acid
Ethyl ester volume ratio carries out gradient elution segmentation successively for 0:1~1:0, and 1 column volume is a stream part, obtains 10 stream part sections,
Stream part section 56, recycling design, that is, obtain Eucarvone 7.8g.
Structural Identification
Colorless oil.1h-nmr(cdcl3,500mhz)δ(ppm):1.78(3h,m,10-ch3),1.82(3h,m,7-
ch3),2.11(1h,m,h-5),2.39(1h,m,h-3),2.45(1h,m,h-5),2.57(1h,s,h-3),2.69(1h,s,h-
4),4.76(1h,s,h-9),4.81(1h,s,h-9),7.65(1h,s,h-6);13c-nmr(cdcl3,125mhz)δ(ppm):
199.34(c-2),146.69(c-8),144.40(c-6),135.45(c-1),110.47(c-9),43.20(c-3),42.55
(c-4),31.30(c-5),20.50(c-10),15.63(c-7).According to1H-nmr and13The data of c-nmr is it may be determined that compound
For Eucarvone.
Embodiment 4
Drug effect toxicology test is studied
1st, fumigation activity method of testing
10 test worms are put into diameter 2.5cm, in the vial of high 5.5cm, the Eucarvone of 3 variable concentrations of preparation is just own
Alkane diluent, then draws 10 μ l dilution drops on the filter paper in bottle cap with liquid-transfering gun, separately takes untreated filter paper Deca
Normal hexane compares, and after volatilization 20s, tightens rapidly bottle cap sealing, forms a confined space, bottleneck scribbles politef
(floun), prevent from touching the filter paper containing medicament for examination insecticide.Each concentration is repeated 5 times, and each repeats 10 test worms.Process
After be placed in temperature be (29 ± 1) DEG C, relative humidity be (75 ± 5) % constant incubator in cultivate 24h, observe and record test worm
Death condition, calculate lc50.
Experimental drug: the compound of the embodiment of the present invention 1;
Positive control drug: methyl bromide, hydrogen phosphide;
The results are shown in Table 1:
The fumigation activity to lasioderma serricorne and red flour beetle for table 1 Eucarvone
**The data referencing document of methyl bromide: liu, z.l., ho, s.h., 1999.bioactivity of the
essential oil extracted from evodiarutaecarpa hook f.et thomas against the
grain storage insects,sitophiluszeamaismotsch and triboliumcastaneum(herbst)
.journal of stored products research,35,317–328.
2nd, contact toxicity method of testing
The adult sprouting wings one week about is taken out from culture bottle, the Eucarvone normal hexane dilution of 3 variable concentrations of preparation
Liquid, (is placed in operation on ice bag) with liquid-transfering gun drop 0.5 μ l on the pronotary of test worm, puts into diameter 2.5cm after process, high
In 5.5cm vial, normal hexane is matched group, and each concentration is repeated 5 times, and each repeats 10 test worms.Treatment group and matched group
Being placed in temperature is (29 ± 1) DEG C, and relative humidity cultivates 24h in the constant incubator for (75 ± 5) %, observes and records test worm
Death condition, calculates ld50.
Experimental drug: the compound of the embodiment of the present invention 1;
Positive control drug: pyrethrin;
The results are shown in Table 2:
The contact toxicity to lasioderma serricorne and red flour beetle for table 2 Eucarvone
3rd, repellent activity method of testing
The circular filter paper of a diameter of 9cm is cut out as two halves from centre, draws 500 μ l Eucarvone normal hexane dilutions with liquid-transfering gun
Liquid (3 concentration of setting: 31.45,7.86 and 1.57nl/cm2, 5 repetitions of each concentration) drip on wherein half filter paper, another
Half is processed as comparison with blank solvent, naturally dries 30s, (ware wall is coated poly- to be pasted onto culture dish bottom in opposite directions with solid gum
Tetrafluoroethene).20 test worms are poured into culture dish central authorities, processes during observed and recorded 2h, 4h, 24h and 48h and compare examination on filter paper
The distribution situation of worm, calculates scattering ratio pr (%), formula is as follows:
Pr (%)=[(nc nt)/(nc+nt)] × 100
Nc is the quantity of test worm on blank filter paper, and nt is the quantity of test worm on administration group filter paper.
Experimental drug: the compound of the embodiment of the present invention 1;
Positive control drug: diethyltoluamide;
The results are shown in Table 3, table 4:
Table 3 Eucarvone scattering ratio (pr% ± se) to lasioderma serricorne in 2h, 4h, 24h, 48h
Table 4 Eucarvone scattering ratio (pr% ± se) to red flour beetle in 2h, 4h, 24h, 48h
Above experimental result shows, the compounds of this invention has to preventing and treating tobacco storage insect lasioderma serricorne, red flour beetle etc.
Preferably prevention effect.
The foregoing describe the preferred embodiment for the present invention, so it is not limited to the present invention.Those skilled in the art couple
Embodiment disclosed herein can carry out the improvement without departing from scope and spirit and change.
Claims (8)
1. a kind of preparation method of Eucarvone is it is characterised in that comprise the following steps:
Step 1) prepare caraway oil: with the Fructus cari carvi pulverized as raw material, using steam distillation or supercritical extraction
Extract caraway oil;
Step 2) chromatography prepares Eucarvone: be separating medium using silica gel, caraway oil and silica gel weight are than for 1:5~1:
15, carry out normal-phase silica gel column chromatography, mobile phase is the mixed liquor of normal hexane and ethyl acetate, using normal hexane: ethyl acetate body
Long-pending ratio carries out gradient elution segmentation successively for 0:1~1:0, and 1 column volume is a stream part, obtains 10 stream part sections, stream part section
56, recycling design, obtain Eucarvone.
2. the preparation method of Eucarvone as claimed in claim 1 is it is characterised in that step 1) described in the way of distillation particularly as follows:
The Fructus cari carvi pulverized is placed in volatile oil extractor, using extraction by steam distillation 3~5h, then is done with anhydrous sodium sulfate
Dry process, obtains final product caraway oil.
3. Eucarvone preparation method as claimed in claim 1 is it is characterised in that step 1) described in supercritical extraction concrete
For: the Fructus cari carvi pulverized mature peel is placed in extraction kettle, extraction kettle and separating still are preheated, basin is carried out cold
But;Open co2Gas cylinder is supplied gas, and opens high-pressure pump boosting;Temperature be 35~50 DEG C, pressure be 5.0~30.0mpa, co2Stream
Under conditions of measuring as 40~80l/h, carry out constant temperature and pressure cycling extraction, discharging after extracting 0.5~2 hour, obtain final product caraway oil.
4. Eucarvone preparation method as claimed in claim 1 is it is characterised in that comprise the following steps:
Step 1) prepare caraway oil: with the Fructus cari carvi pulverized as raw material, using steam distillation or supercritical extraction
Extract caraway oil;
Step 2) chromatography prepares Eucarvone: be separating medium using silica gel, caraway oil and silica gel weight are than for 1:5~1:
15, carry out normal-phase silica gel column chromatography, mobile phase is the mixed liquor of normal hexane and ethyl acetate, using normal hexane: ethyl acetate body
Long-pending ratio carries out gradient elution segmentation successively for 0:1~1:0, and 1 column volume is a stream part, obtains 10 stream part sections, stream part section
56, recycling design, obtain Eucarvone;
Step 1) described in the way of distillation particularly as follows: the Fructus cari carvi pulverized is placed in volatile oil extractor, using vapor steam
The method that evaporates extracts 3~5h, then is processed with anhydrous sodium sulfate drying, obtains final product caraway oil;
Step 1) described in supercritical extraction particularly as follows: the Fructus cari carvi pulverized mature peel is placed in extraction kettle, to extraction
Take kettle and separating still to be preheated, basin is cooled down;Open co2Gas cylinder is supplied gas, and opens high-pressure pump boosting;In temperature it is
35~50 DEG C, pressure be 5.0~30.0mpa, co2Under conditions of flow is 40~80l/h, carry out constant temperature and pressure cycling extraction,
Discharging after extracting 0.5~2 hour, obtains final product caraway oil.
5. Eucarvone preparation method as claimed in claim 1 is it is characterised in that comprise the following steps:
1) vapor distillation preparation: take Fructus cari carvi 1.0kg, pulverize in rearmounted volatile oil extractor, carried using steam distillation
Take 4h, processed with anhydrous sodium sulfate drying, obtain caraway oil 38.4ml, be stored in 4 DEG C of fresh keeping chamber of refrigerator standby;
2) supercritical co2Prepared by extraction process: take Fructus cari carvi 1.0kg, pulverize in rearmounted extraction kettle, first extraction kettle, separating still are entered
Row preheating, basin is cooled down, and when reaching predetermined temperature, opens co2Gas cylinder is supplied gas, and opens high-pressure pump boosting, when temperature, pressure
When power reaches predetermined value, start the cycle over extraction, fixedly separated pressure 10.0mpa during extraction, 40 DEG C of separation temperature, co2Flow is
60l/h, constant temperature and pressure extract 1.5 hours after discharging, obtain caraway oil 41.0ml, be stored in 4 DEG C of fresh keeping chamber of refrigerator standby;
3) compound separates: Fructus cari carvi volatile oil 20ml, is separating medium using silica gel, oils with silica-gel materials weight ratio as 1:
10, through normal-phase silica gel column chromatography, mobile phase is the mixed liquor of normal hexane and ethyl acetate, using normal hexane: ethyl acetate volume
Carry out gradient elution segmentation successively than for 0:1~1:0, that is, initial solvent be normal hexane 100%, terminate for ethyl acetate be
100%;1 column volume is a stream part, obtains 10 stream part sections, stream part section 56, recycling design, obtains Eucarvone.
6. application in preventing and treating tobacco storage insect for the Eucarvone.
7. application as claimed in claim 6, it is characterised in that described Eucarvone, is arbitrary preparation method in claim 1-5
It is prepared from.
8. the application described in claim 6 or 7 is it is characterised in that described tobacco storage insect includes lasioderma serricorne, red flour beetle.
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CN106977390A (en) * | 2017-04-13 | 2017-07-25 | 嘉兴德扬生物科技有限公司 | A kind of efficient and environmentally friendly anisic acid preparation method |
CN112057483A (en) * | 2020-10-22 | 2020-12-11 | 河北赛谱睿思医药科技有限公司 | Preparation method and application of effective part of traditional Chinese medicine volatile oil |
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Application publication date: 20170201 |