CN107698545A - A kind of preparation method of the spices maltol of natural botanical source - Google Patents
A kind of preparation method of the spices maltol of natural botanical source Download PDFInfo
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- CN107698545A CN107698545A CN201611035985.7A CN201611035985A CN107698545A CN 107698545 A CN107698545 A CN 107698545A CN 201611035985 A CN201611035985 A CN 201611035985A CN 107698545 A CN107698545 A CN 107698545A
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- maltol
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- ethyl acetate
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/34—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D309/36—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
- C07D309/40—Oxygen atoms attached in positions 3 and 4, e.g. maltol
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Abstract
The invention discloses a kind of preparation method of the maltol of natural botanical source.The invention is using evodia rutaecarpa slenderstyle acanthopanax leaf as raw material, after solvent extraction, merges extract solution；Extract solution obtains concentrate with flash concentration recycling design；Maltol crude extract is extracted with ethyl acetate to obtain with after petroleum ether extraction degreasing in concentrate；The crude extract distils to obtain maltol sterling by molecular still.The preparation method of maltol of the present invention have the advantages that raw material from natural plants, preparation process is simple and convenient to operate without using any toxic reagent, technique, yield is high, product purity is high, suitable for industrialized production.
Description
Technical field
The invention belongs to plant technology field, specially a kind of preparation method of the maltol of natural botanical source.
Background technology
Evodia rutaecarpa five adds as studies on plants of Acanthopanax Miq. in Araliaceae, is distributed widely in China Yangtze river basin and the Changjiang river areas to the south,
Its root skin has dispelling wind and eliminating dampness, regulating qi-flowing for eliminating phlegm effect.Arthralgia pain due to rheumatism is cured mainly, soreness of waist and knee joint, oedema, traumatic injury, epersalgia cough, is roared
Asthma, spit blood.Its leaf is also used for treating for skin disease by seedling medicine.Due to its aboundresources, there is great potentiality to be exploited.Evodia rutaecarpa
The chemical constitution study of slenderstyle acanthopanax leaf shows that it contains abundant carbohydrate, triterpenes and flavone compound.
Maltol belongs to food flavor dispensing and fumet class, can promote and reconcile the fragrance of product, cover bad wind
Taste.The palatability of feed can be greatly increased by being added in poultry and livestock feed additive, strengthen the appetite of poultry, therefore it has pole
High research and development value.Industrial synthesis maltol is using the method for Pfizen companies of U.S. invention, using furfural as original mostly
Material, first carry out grignard reaction with chloromethanes and Alpha-Methyl furancarbinol is made, then synthesize maltol by chlorinated hydrolysis.Chaff
Although aldehyde is a kind of with natural material made from natural grain bar, chaff shell etc., but chloromethanes used is petrochemicals,
Therefore so obtained maltol can not can be regarded as natural prodcuts.In order to meet the needs of international market is to native malt phenol, there is
Person is prepared for native malt phenol using natural methanol and natural furfural as raw material, although compared to the maltol reaction bar industrially prepared
Part is gentleer, and reaction is more easy to carry out, but more by everybody in the today for praising highly " green ", the product of natural botanical source
Concern and expectation.
Studies have found that it is present in malt, larch, silver fir, witloof, the coffee roasted, cocoa, point of soybean
Solve in liquid, the barley roasting natural plants such as condensate and wooden vinegar.The method for preparing maltol from these natural plants has U.S.'s use
Extractive crystallization process extracts maltol from wooden vinegar, and chloroform recovery maltol is used from bark of dahurian larch.Japan is from katsura tree leaf
Extracted with chloroform derect seething or from its steam distillation liquid；It is evaporated under reduced pressure from the wood tar obtained by the dry distillation of wood and also may be used
It is separated to maltol.However, preceding method is deposited, contained maltol content in the feed is low, manufacturing process needs to use poisonous examination
The defects of agent or cumbersome making step.On the basis of early stage is studied evodia rutaecarpa slenderstyle acanthopanax leaf, it is found that it has the wheat of rich content
Bud phenol, and there is not been reported for the research to its preparation method.
The content of the invention
For the above-mentioned problems in the prior art, it is an object of the invention to design to provide a kind of natural botanical source
Maltol preparation method, its technique is simple, and the rate of recovery is high, easy to operate, green high-efficient, and it is new to obtain a kind of maltol
Natural botanical source.
To achieve the above object, the technical solution adopted by the present invention：
A kind of preparation method of the maltol of natural botanical source, it is characterised in that comprise the following steps：
(1) extract：The solvent (based on evodia rutaecarpa slender acanthopanax leaf quality) that evodia rutaecarpa slenderstyle acanthopanax leaf is added to 6~10 times of volumes extracts
2-3 times, merge extract solution；
(2) flash concentration：By extract solution in 50 DEG C~100 DEG C of bath temperature, vacuum 0.060Mpa-0.095Mpa bar
It is concentrated in vacuo under part, recycling design, obtains concentrate；
(3) degreasing：Concentrate carries out ungrease treatment with petroleum ether；
(4) prepared by crude extract：The concentrate of ungrease treatment is extracted with ethyl acetate, combined ethyl acetate extract,
Concentration and recovery ethyl acetate produces maltol crude extract to dry cream；
(5) sublimation separation purifies：Maltol crude extract is used into molecular still, is 0.05Pa-0.06Pa in vacuum,
105 DEG C -125 DEG C of temperature, distillation processing is carried out to it, produces maltol white needles.
In step (2)：Cold soaking extraction, homogenate extraction, one kind in heating and refluxing extraction or more can be used in described extraction
Kind.
In step (2)：The solvent is ethanol, water or their mixture.
A kind of preparation method of the maltol of above-mentioned natural botanical source, there is advantages below：
(1) maltol is prepared from natural plants evodia rutaecarpa slenderstyle acanthopanax leaf, not only ensure that its green and healthy environmental protection, Er Qiegeng
It is the increase in a kind of new natural botanical source of maltol；
(2) extract solution uses flash concentration, has that concentrate heating temperature is relatively low, heated time is shorter, concentration speed is fast,
Efficiency high, the advantage such as simple to operate, easy to use, energy-conserving and environment-protective；
(3) compared with conventional purification methods, avoiding high temperature distillation causes the carbonization and decomposition of maltol, substantially increases
The rate of recovery of maltol.
Brief description of the drawings
Fig. 1 maltols HPLC detects collection of illustrative plates
Fig. 2 maltols1H-NMR collection of illustrative plates
Fig. 3 maltols13C-NMR collection of illustrative plates
Embodiment
Below in conjunction with specific embodiment, the present invention will be further described.
Embodiment 1
(1) extract：Evodia rutaecarpa slenderstyle acanthopanax leaf is added to 15% ethanol solution of 8 times of volumes (based on evodia rutaecarpa slender acanthopanax leaf quality)
Heating and refluxing extraction 3 times, 2 hours every time, merge extract solution；
(2) flash concentration：It is dense that extract solution is carried out under conditions of 60 DEG C of bath temperature, vacuum 0.075Mpa to vacuum
Contracting, recycling design, obtains concentrate；
(3) degreasing：Concentrate carries out ungrease treatment 3 times with petroleum ether extraction；
(4) prepared by crude extract：The concentrate of ungrease treatment is extracted with ethyl acetate 4 times, combined ethyl acetate extraction
Liquid, concentration and recovery ethyl acetate to dry cream, produce maltol crude extract；
(5) sublimation separation purifies：Maltol crude extract is used into molecular still, is 0.06Pa in vacuum, temperature 105
DEG C, distillation processing is carried out to it, produces maltol white needles.
Embodiment 2
(1) extract：Evodia rutaecarpa slenderstyle acanthopanax leaf is added to 80% ethanol solution of 6 times of volumes (based on evodia rutaecarpa slender acanthopanax leaf quality)
Homogenate extraction 2 times, merge extract solution；
(2) flash concentration：It is dense that extract solution is carried out under conditions of 70 DEG C of bath temperature, vacuum 0.095Mpa to vacuum
Contracting, recycling design, obtains concentrate；
(3) degreasing：Concentrate carries out ungrease treatment 3 times with petroleum ether extraction；
(4) prepared by crude extract：The concentrate of ungrease treatment is extracted with ethyl acetate 3 times, combined ethyl acetate extraction
Liquid, concentration and recovery ethyl acetate to dry cream, produce maltol crude extract；
(5) sublimation separation purifies：Maltol crude extract is used into molecular still, is 0.055Pa in vacuum, temperature
110 DEG C, distillation processing is carried out to it, produces maltol white needles.
Embodiment 3
(1) extract：Evodia rutaecarpa slenderstyle acanthopanax leaf is added to absolute ethyl alcohol (based on evodia rutaecarpa slender acanthopanax leaf quality) room of 10 times of volumes
The lower cold soaking of temperature extracts 2 times, 7 days every time, merges extract solution；
(2) flash concentration：It is dense that extract solution is carried out under conditions of 80 DEG C of bath temperature, vacuum 0.092Mpa to vacuum
Contracting, recycling design, obtains concentrate；
(3) degreasing：Concentrate carries out ungrease treatment 5 times with petroleum ether extraction；
(4) prepared by crude extract：The concentrate of ungrease treatment is extracted with ethyl acetate 3 times, combined ethyl acetate extraction
Liquid, concentration and recovery ethyl acetate to dry cream, produce maltol crude extract；
(5) sublimation separation purifies：Maltol crude extract is used into molecular still, is 0.052Pa in vacuum, temperature
115 DEG C, distillation processing is carried out to it, produces maltol white needles.
The purity test of embodiment 4
Instrument：LC-10AT type high performance liquid chromatographs, SPD-10A type UV-vis detectors, CBM-10A type chromatogram works
Stand, chromatographic column Promosil C18(4.6mm × 250mm, 5 μm)；Mobile phase：0.1% formic acid water-acetonitrile (72: 28)；Flow velocity：
0.5mL/min；Column temperature：30℃；Detection time is 25min, Detection wavelength：276nm.
The maltol white needles obtained in Example 1-3 any embodiments, accurately weighed, be dissolved in water simultaneously constant volume,
Shake up, cross 0.45 μm of miillpore filter filtration, be measured by above-mentioned chromatographic condition, HPLC detection collection of illustrative plates is shown in Fig. 1.
The Structural Identification of embodiment 5
The maltol white needles obtained in Example 1-3 any embodiments, deuterochloroform solvent, use DRX 400/
300 NMRs (Bruker companies) analyze its nuclear magnetic data.Main nuclear magnetic data is as follows：1H-NMR (600MHz, CD3OD)
δ：2.33 (3H, s, CH3), 6.37 (1H, d, J=5.5Hz, H-5), 7.92 (1H, d, J=5.5Hz, H-6)；13C-NMR
(150MHz, CD3OD)δ：156.4 (C-2), 152.4 (C-3), 175.4 (C-4), 114.5 (C-5), 144.7 (C-6), 14.4
(CH3).Spectrogram is as shown in Figure 2 and Figure 3.Maltol structural formula is as follows：
The general principle and principal character and advantages of the present invention of the present invention has been shown and described in above example.One's own profession
The technical staff of industry is not it should be appreciated that the present invention is limited by above-described embodiment and experimental example, in above-described embodiment and specification
Description merely illustrates the principles of the invention, rather than the scope limiting the invention in any way, and is not departing from model of the present invention
On the premise of enclosing, various changes and modifications of the present invention are possible, and these changes and improvements are both fallen within claimed scope.
Claims (3)
1. a kind of preparation method of the maltol of natural botanical source, it is characterised in that comprise the following steps：
(1) extract：The solvent (based on evodia rutaecarpa slender acanthopanax leaf quality) that evodia rutaecarpa slenderstyle acanthopanax leaf is added to 6~10 times of volumes extracts 2-3
It is secondary, merge extract solution；
(2) flash concentration：By extract solution under conditions of 50 DEG C~100 DEG C of bath temperature, vacuum 0.060Mpa-0.095Mpa
It is concentrated in vacuo, recycling design, obtains concentrate；
(3) degreasing：Concentrate carries out ungrease treatment with petroleum ether；
(4) prepared by crude extract：The concentrate of ungrease treatment is extracted with ethyl acetate, combined ethyl acetate extract, concentrated
Ethyl acetate is reclaimed to dry cream, produces maltol crude extract；
(5) sublimation separation purifies：Maltol crude extract is used into molecular still, is 0.05Pa-0.06Pa in vacuum, temperature
105 DEG C -125 DEG C, distillation processing is carried out to it, produces maltol white needles.
A kind of 2. preparation method of the maltol of natural botanical source as claimed in claim 1, it is characterised in that step (2)
In：The one or more in cold soaking extraction, homogenate extraction, heating and refluxing extraction can be used in described extraction.
A kind of 3. preparation method of the maltol of natural botanical source as claimed in claim 1 or 2, it is characterised in that step
(2) in：The solvent is ethanol, water or their mixture.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201611035985.7A CN107698545A (en) | 2016-11-19 | 2016-11-19 | A kind of preparation method of the spices maltol of natural botanical source |
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| CN201611035985.7A CN107698545A (en) | 2016-11-19 | 2016-11-19 | A kind of preparation method of the spices maltol of natural botanical source |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114858939A (en) * | 2022-04-27 | 2022-08-05 | 国家烟草质量监督检验中心 | Method for simultaneously determining eugenol, maltol, ethyl maltol, vanillin and ethyl vanillin in novel atomized product |
Citations (6)
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|---|---|---|---|---|
| US5221756A (en) * | 1992-02-21 | 1993-06-22 | Florasynth, Inc. | Method for the recovery and purification of maltol |
| US5646312A (en) * | 1996-01-03 | 1997-07-08 | Florasynth, Inc. | Process of aqueous extraction of maltol |
| CA2259481A1 (en) * | 1998-02-09 | 1999-08-09 | Kemestrie Inc. | Direct extraction and/or purification of high purity maltol and essential oils by sublimation process |
| US6384246B1 (en) * | 2001-02-26 | 2002-05-07 | Council Of Scientific & Industrial Research | Process for the preparation of maltol from plants belonging to the genus Abies |
| CN103113339A (en) * | 2012-11-11 | 2013-05-22 | 安徽金禾实业股份有限公司 | Maltol separation and purification method |
| CN105943576A (en) * | 2016-05-09 | 2016-09-21 | 南京明宽信息咨询中心 | Extracting method of radix acanthopanacis semticosi and radix acanthopanacis semticosi health product |
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2016
- 2016-11-19 CN CN201611035985.7A patent/CN107698545A/en active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5221756A (en) * | 1992-02-21 | 1993-06-22 | Florasynth, Inc. | Method for the recovery and purification of maltol |
| US5646312A (en) * | 1996-01-03 | 1997-07-08 | Florasynth, Inc. | Process of aqueous extraction of maltol |
| CA2259481A1 (en) * | 1998-02-09 | 1999-08-09 | Kemestrie Inc. | Direct extraction and/or purification of high purity maltol and essential oils by sublimation process |
| US6384246B1 (en) * | 2001-02-26 | 2002-05-07 | Council Of Scientific & Industrial Research | Process for the preparation of maltol from plants belonging to the genus Abies |
| CN103113339A (en) * | 2012-11-11 | 2013-05-22 | 安徽金禾实业股份有限公司 | Maltol separation and purification method |
| CN105943576A (en) * | 2016-05-09 | 2016-09-21 | 南京明宽信息咨询中心 | Extracting method of radix acanthopanacis semticosi and radix acanthopanacis semticosi health product |
Non-Patent Citations (2)
| Title |
|---|
| KAI-YUE CAO等: "Chemical Constituents from Leaves of Oplopanax horridus", 《CHINESE HERBAL MEDICINES》 * |
| 李小军等: "吴茱萸五加叶化学成分研究", 《中草药》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114858939A (en) * | 2022-04-27 | 2022-08-05 | 国家烟草质量监督检验中心 | Method for simultaneously determining eugenol, maltol, ethyl maltol, vanillin and ethyl vanillin in novel atomized product |
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Address after: 410205 Jinhongyuan Incubation Building A505, 229 Tongzipo West Road, Changsha High-tech Development Zone, Changsha City, Hunan Province Applicant after: Changsha Broad-Ocean Bio-Science Co.,Ltd. Address before: 410205 55F, Building A, Lugu International Industrial Park, 229 Tongzipo West Road, Yuelu District, Changsha City, Hunan Province Applicant before: Changsha Broad-Ocean Bio-Science Co.,Ltd. |
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Application publication date: 20180216 |