CN105837442B - The separation method of aroma component divaricatic acid ethyl ester in tongue delicate fragrance type spices - Google Patents
The separation method of aroma component divaricatic acid ethyl ester in tongue delicate fragrance type spices Download PDFInfo
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Abstract
The present invention provides a kind of separation method of aroma component divaricatic acid ethyl ester in tongue delicate fragrance type spices, sample to be separated is obtained by pretreatment, by pretreated oak moss or tree moss concrete ethyl acetate solution, it is slowly dropped to silicagel column upper surface, obtain one-level sample solution to be separated, it is object aroma component divaricatic acid ethyl ester after eluent removing solvent after secondary separation；This method is with the important aroma component divaricatic acid ethyl ester in column chromatography for separation method separating natural tongue delicate fragrance raw material, good separating effect, purity are high, extraction process is relatively simple, it can be achieved using two-stage separation, avoid the instrument and equipment of the complicated and time consumptions such as Soxhlet extraction device, and product yield is high, prepared by the industrial mass for being suitable for divaricatic acid ethyl ester, the source of horn of plenty natural perfume material provides technological approaches.
Description
Technical field
The present invention relates to a kind of separation method of aroma component divaricatic acid ethyl ester in tongue delicate fragrance type spices.
Background technology
Tongue green grass or young crops fragrant perfume mainly includes tree moss and medicinal extract, the absolute oil product of oak moss, by flat using Usneaceae is belonged to
A kind of Lecanorales lichen of branch clothing category is made as raw material through certain processing technology.Produce tree moss concrete, absolute oil
Raw material is tree moss, and oakmoss concrete, the raw material of absolute oil are oak moss, wherein, be grown on the European middle and south and Mediterranean south this
The quality of the blue or green fragrant fragrant perfume of tongue prepared by the lichens raw material of the country such as pressgang, France and Italy is the most excellent.Tongue green grass or young crops odor type
Spices due to uniqueness liverwort material natural delicate fragrance and strong resin breath, be important natural perfume material, food,
The fields such as cosmetics, flavouring essence for tobacco are using extremely wide.
But as a kind of natural perfume material, containing invalid components such as substantial amounts of pigment and vegetable waxs in medicinal extract and absolute oil, lead
Cause aroma quality and the purity of spices not good enough, next to that also often causing the composition of people's allergy containing some in medicinal extract and absolute oil
With a considerable amount of heavy metals, the product quality for food service industry and daily use chemicals industry has buried potential safety hazard.Have been reported that and show rubber
The compositions such as tongue, the atranorine in tree moss product, chloro atranorine, lichenic acid are probably the thing for inducing human allergy's reaction
Matter.Point out should not contain in cosmetics in European consumer goods Science committee (SCCP) report (SCCP/0847/04) A Lan phenol,
The compositions such as chloro A Lan phenol.Oak moss product application when cosmetics, the content of A Lan phenol and chloro A Lan phenol should be down to 2ppm with
Under, tree moss product is similar to oak moss product, and the content and processing mode of its A Lan phenol and chloro A Lan phenol are entered with reference to oak moss product
Row constraint.
In view of this, researcher starts to extract or synthesizes the important aroma component in tongue delicate fragrance spices, is caused with these
Fragrant composition carries out the compounding of essence, restructuring, is deployed into the replacement essence with tongue delicate fragrance style characteristic and is used.Such as China specially
Sharp CA103333A has been compounded using the composition such as everninic acid ethyl ester, red star clothing acetoacetic ester a kind of has natural tongue delicate fragrance true to nature
The essence of type spices aromatic style.Wu Guosheng of Chinese Academy of Sciences's Shanghai Institute of Organic Chemistry etc. closes in the chemistry of patent the main essence of oak moss
Cheng Zhong, disclose a kind of main note composition -3,6- dimethyl-β-resorcylic acid methyl esters (i.e. β-orcin carboxylate methyl ester) of oak moss
Preparation method.
As the main aroma component of tongue delicate fragrance type spices, divaricatic acid ethyl ester content is larger, domestic rubber in being particularly
Tongue, tree moss product, the content nearly 20% of divaricatic acid ethyl ester.Patent CN102351706 A disclose divaricatic acid ethyl ester
A kind of methodology of organic synthesis.But have not yet to see using soft Evernia in column chromatography for separation tongue delicate fragrance type natural perfume material
The various documents and patent report of acetoacetic ester.Therefore, it is necessary to develop it is a kind of it is fast and effective, be suitable for industrialized mass production
Separation method, the kind of flavor formula field is enriched, go out more preferable composition for the blending staff development of essence and flavoring agent industry
Necessary perfume material is provided.
The content of the invention
It is an object of the invention to provide a kind of separation method of aroma component divaricatic acid ethyl ester in tongue delicate fragrance type spices,
Important aroma component divaricatic acid ethyl ester in tongue delicate fragrance natural perfume material is extracted using column chromatography for separation method, how quick solved
Effectively, the problem of being suitable for industrialized mass production.
The present invention technical solution be：
The separation method of aroma component divaricatic acid ethyl ester in a kind of tongue delicate fragrance type spices, including：
Step 1, tree moss concrete or oakmoss concrete raw material are weighed, add acetonitrile thereto, after being stirred vigorously, standing 10~
It is layered after 20min, upper solution is filtered by vacuum using Buchner funnel, removes precipitation, receives tree moss concrete or oakmoss concrete
Acetonitrile solution；
Step 2, the sample solution that step 1 obtains removed into acetonitrile solvent therein by Rotary Evaporators, obtain treating point
From sample；
Step 3, wet method dress post：100~300 mesh silica gel are taken in beaker, the appropriate eluant, eluent configured is added, fully stirs
Continuously poured into after mixing in silicagel column, using 40~200cm of column length, 4~50cm of diameter silicagel column；
Step 4, the sample to be separated for obtaining step 2 are dissolved with ethyl acetate, and solution is slowly dropped on silicagel column
Surface, opening regulating valve makes sample solution fully enter in silica gel；
Step 5, from the post eluant, eluent suitable for reading for being slowly added into step 3, observe the change of colour band, treat the leading portion yellow band of sample
Behind the bottom for reaching silicagel column, yl moiety colour band is received with sample bottle, after chromatography terminates, it is removed according to the method for step 2
In solvent, obtain one-level sample solution to be separated；
Step 6,100~300 mesh silica gel are taken in beaker, add the appropriate eluant, eluent configured, it is continuous after being sufficiently stirred
Pour into silicagel column, using 40~200cm of column length, 3~20cm of diameter silicagel column；
Step 7, eluant, eluent of the sample that step 5 obtains in step 6 dissolved, solution is slowly dropped to the silicon of step 6
Glue post upper surface, opening regulating valve makes sample solution fully enter in silica gel, then adds the eluent sample of step 6；
Step 8, after reaching the bottom of pillar after the colour band forward position of sample, efflux is received with triangular flask, with thin layer silica gel
Plate point sample method detects chromatographic solution, judges whether target components flow out under uviol lamp, and the component that treating sample has UV absorption flows out
When, use sample bottle instead and receive eluent, untill all components for having UV absorption all elute, eluent removes solvent
It is object aroma component divaricatic acid ethyl ester afterwards.
Further, described silicagel column is equipped with tetrafluoroethene regulating valve and core.
Further, the mass ratio of raw material and acetonitrile is 1 in step 1:2.5~5.
Further, in step 3, described eluant, eluent is petroleum ether and ethyl acetate mixed solvent, petroleum ether and acetic acid
The volume ratio of ethyl ester is 9~15:1.
Further, in step 6, described eluant, eluent is petroleum ether and ethyl acetate mixed solvent, petroleum ether and acetic acid
The volume ratio of ethyl ester is 18~25:1.
Further, step 4 and the material used in the column chromatography in step 7 and the mass ratio of silica gel are 1:4~1:80.
The beneficial effects of the invention are as follows：The separation side of aroma component divaricatic acid ethyl ester in this kind of tongue delicate fragrance type spices
Method, divaricatic acid ethyl ester is isolated from natural tongue delicate fragrance spices using column chromatography first, separation process does not introduce acid
Alkali, it is clean that the low boiling point solvent of use is easy to volatilization, confirms through mass spectral analysis, divaricatic acid ethyl ester with it is other in spices
Compound, which realizes, to be kept completely separate；Isolated divaricatic acid ethyl ester is directed to natural plant pefume, whole process
It is not introduced into other impurity, it is not necessary to by programs such as safety evaluations, be used directly for matching somebody with somebody for the high-grade essence such as food, cosmetics
System；Using handling in advance natural perfume material, insoluble part therein is removed, alleviates resistance during column chromatography for separation
Power, shorten disengaging time；Separating step is easy, can be achieved using two-stage separation, avoids the complexity such as Soxhlet extraction device
Time-consuming instrument and equipment, and product yield is high, prepared by the industrial mass for being suitable for divaricatic acid ethyl ester, horn of plenty natural perfume
The source of material provides technological approaches.
Brief description of the drawings
Fig. 1 is the structural formula for the divaricatic acid ethyl ester that embodiment 1 is isolated from tree moss concrete.
Embodiment
In order to illustrate more clearly of the present invention, the present invention is done further with reference to preferred embodiments and drawings
It is bright.Specifically described content is illustrative and be not restrictive below, should not be limited the scope of the invention with this.
The separation method of important aroma component divaricatic acid ethyl ester in the tongue delicate fragrance raw material of embodiment, including dissolving, mistake
The steps such as filter, concentration and column chromatography.Embodiment is with the important aroma component in column chromatography for separation method separating natural tongue delicate fragrance raw material
Divaricatic acid ethyl ester, good separating effect, purity are high, and extraction process is relatively simple, is further beneficial to industrialized mass production
The source of abundant perfume material provides technological approaches, has a extensive future.
Embodiment 1
Pretreatment：30g tree moss concrete is weighed, 75g acetonitrile is added thereto, stands 15min after being sufficiently stirred, use cloth
Family name's funnel removes insoluble part therein, and the dissolving part of tree moss concrete removes acetonitrile solvent therein with Rotary Evaporators, obtained
It is standby after being dissolved with ethyl acetate to sample to be separated, the sample.
Fill post：120g silica gel is taken in 1000ml beakers, adds volume ratio 9 thereto:1 petroleum ether and ethyl acetate
Mixed solvent, it is sufficiently stirred and continuously pours into a diameter of 4cm afterwards, in the glass silica gel post that column length is 40cm, and it is mixed to be continuously added this
Bonding solvent rinses repeatedly as eluant, eluent so that silica gel is able to the effect for reaching Equalsettlement, while ensures the height of eluant, eluent
Higher than silica gel.
Just separation：By pretreated tree moss concrete ethyl acetate solution, silicagel column upper surface is slowly dropped to, opens silicon
Glue post regulating valve makes sample solution fully enter in silica gel, and volume ratio is used as petroleum ether from suitable for reading be slowly added into of post：Acetic acid second
Ester=9:1 eluant, eluent, the change of colour band is observed, after the leading portion yellow band of sample reaches the bottom of silicagel column, use sample bottle
Yl moiety colour band is received, after chromatography terminates, solvent therein is removed using Rotary Evaporators, obtains one-level sample to be separated
Solution.
Secondary separation：100g silica gel is weighed in 1000ml beakers, uses volume ratio as 18:1 petroleum ether and acetic acid second
Ester mixed solvent is according to preceding method by silica gel loaded in a diameter of 3cm, the glass silica gel post that column length is 40cm；One-level is separated
Sample is petroleum ether with volume ratio：Ethyl acetate=18:Loading after 1 eluant, eluent dissolving, is slowly added dropwise silicagel column upper surface, beats
Opening regulating valve makes sample solution fully enter in silica gel, then the addition step eluent sample.
After reaching the bottom of pillar after the colour band forward position of sample, efflux is received with triangular flask, with thin layer silica gel plate point sample
Method detects chromatographic solution, judges whether target components flow out under uviol lamp, when the component that sample has UV absorption flows out, uses instead
Sample bottle receives eluent, untill all components for having UV absorption all elute.Object is identified：Eluent concentrates
After remove solvent content therein, obtain white needles thing, determined through melting point apparatus, the fusing point of the solids is 43~45
DEG C, through Bruker-DRX500 type NMRs, Micromass GC-TOF high resolution mass spectrums instrument, Bruker ALPHA
Infrared spectrometer confirm, it is isolated for divaricatic acid ethyl ester, its structure it is as shown in Figure 1.Through Agilent 6890-5975
GC-MS types gaseous mass analyzer determines, and the purity of isolated divaricatic acid ethyl ester is more than 99%.
Embodiment 2
Pretreatment：40g oakmoss concrete is weighed, 160g acetonitrile is added thereto, 20min is stood after being sufficiently stirred, is used
Buchner funnel removes insoluble part therein, and the dissolving part of oakmoss concrete removes acetonitrile solvent therein with Rotary Evaporators,
Sample to be separated is obtained, the sample is standby after being dissolved with ethyl acetate.
Fill post：160g silica gel is taken in 1000ml beakers, adds volume ratio 15 thereto:1 petroleum ether and ethyl acetate
Mixed solvent, be sufficiently stirred and continuously pour into a diameter of 20cm afterwards, in the glass silica gel post that column length is 100cm, and be continuously added
The mixed solvent rinses repeatedly as eluant, eluent so that silica gel is able to the effect for reaching Equalsettlement, while ensures eluant, eluent
Highly it is higher than silica gel.
Just separation：By pretreated oakmoss concrete ethyl acetate solution, silicagel column upper surface is slowly dropped to, opens silicon
Glue post regulating valve makes sample solution fully enter in silica gel, is petroleum ether from the post volume ratio suitable for reading that is slowly added into：Ethyl acetate=
15:1 eluant, eluent, the change of colour band is observed, after the leading portion yellow band of sample reaches the bottom of silicagel column, received with sample bottle
Yl moiety colour band, after chromatography terminates, solvent therein is removed using Rotary Evaporators, it is molten to obtain one-level sample to be separated
Liquid.
Secondary separation：130g silica gel is weighed in 1000ml beakers, uses volume ratio as 25:1 petroleum ether and acetic acid second
Ester mixed solvent is according to preceding method by silica gel loaded in a diameter of 4cm, the glass silica gel post that column length is 40cm；One-level is separated
Sample is petroleum ether with volume ratio：Ethyl acetate=25:Loading after 1 eluant, eluent dissolving, is slowly added dropwise silicagel column upper surface, beats
Opening regulating valve makes sample solution fully enter in silica gel, then the addition step eluent sample.
After reaching the bottom of pillar after the colour band forward position of sample, efflux is received with triangular flask, with thin layer silica gel plate point sample
Method detects chromatographic solution, judges whether target components flow out under uviol lamp, when the component that sample has UV absorption flows out, uses instead
Sample bottle receives eluent, untill all components for having UV absorption all elute.Object is identified：Eluent concentrates
After remove solvent content therein, obtain white needles thing, determined through melting point apparatus, the fusing point of the solids is 43~45
DEG C, through Bruker-DRX500 type NMRs, Micromass GC-TOF high resolution mass spectrums instrument, Bruker ALPHA
Infrared spectrometer confirm, it is isolated for divaricatic acid ethyl ester, its structure it is as shown in Figure 1.Through Agilent 6890-5975
GC-MS types gaseous mass analyzer determines, and the purity of isolated divaricatic acid ethyl ester is more than 99%.
Embodiment 3
Pretreatment：50g oakmoss concrete is weighed, 250g acetonitrile is added thereto, 25min is stood after being sufficiently stirred, is used
Buchner funnel removes insoluble part therein, and the dissolving part of oakmoss concrete removes acetonitrile solvent therein with Rotary Evaporators,
Sample to be separated is obtained, the sample is standby after being dissolved with ethyl acetate.
Fill post：200g silica gel is taken in 1000ml beakers, adds volume ratio 10 thereto:1 petroleum ether and ethyl acetate
Mixed solvent, be sufficiently stirred and continuously pour into a diameter of 25cm afterwards, in the glass silica gel post that column length is 100cm, and be continuously added
The mixed solvent rinses repeatedly as eluant, eluent so that silica gel is able to the effect for reaching Equalsettlement, while ensures eluant, eluent
Highly it is higher than silica gel.
Just separation：By pretreated oakmoss concrete ethyl acetate solution, silicagel column upper surface is slowly dropped to, opens silicon
Glue post regulating valve makes sample solution fully enter in silica gel, is petroleum ether from the post volume ratio suitable for reading that is slowly added into：Ethyl acetate=
20:1 eluant, eluent, the change of colour band is observed, after the leading portion yellow band of sample reaches the bottom of silicagel column, received with sample bottle
Yl moiety colour band, after chromatography terminates, solvent therein is removed using Rotary Evaporators, it is molten to obtain one-level sample to be separated
Liquid.
Secondary separation：160g silica gel is weighed in 1000ml beakers, uses volume ratio as 25:1 petroleum ether and acetic acid second
The mixed solvent of ester is according to preceding method by silica gel loaded in a diameter of 5cm, the glass silica gel post that column length is 80cm；By a fraction
With volume ratio it is petroleum ether from sample：Ethyl acetate=20:Loading after 1 eluant, eluent dissolving, is slowly added dropwise silicagel column upper surface,
Opening regulating valve makes sample solution fully enter in silica gel, then the addition step eluent sample.
After reaching the bottom of pillar after the colour band forward position of sample, efflux is received with triangular flask, with thin layer silica gel plate point sample
Method detects chromatographic solution, judges whether target components flow out under uviol lamp, when the component that sample has UV absorption flows out, uses instead
Sample bottle receives eluent, untill all components for having UV absorption all elute.Object is identified：Eluent concentrates
After remove solvent content therein, obtain white needles thing, determined through melting point apparatus, the fusing point of the solids is 43~45
DEG C, through Bruker-DRX500 type NMRs, Micromass GC-TOF high resolution mass spectrums instrument, Bruker ALPHA
Infrared spectrometer confirm, it is isolated for divaricatic acid ethyl ester, its structure it is as shown in Figure 1.Through Agilent 6890-5975
GC-MS types gaseous mass analyzer determines, and the purity of isolated divaricatic acid ethyl ester is more than 99%.
Obviously, the above embodiment of the present invention is only intended to clearly illustrate example of the present invention, and is not pair
The restriction of embodiments of the present invention.For those of ordinary skill in the field, may be used also on the basis of the above description
To make other changes in different forms.Here all embodiments can not be exhaustive.It is every to belong to this hair
Row of the obvious changes or variations that bright technical scheme is extended out still in protection scope of the present invention.
Claims (6)
- A kind of 1. separation method of aroma component divaricatic acid ethyl ester in tongue delicate fragrance type spices, it is characterised in that including：Step 1, tree moss concrete or oakmoss concrete raw material are weighed, add acetonitrile thereto, after being stirred vigorously, stand 10~20min After be layered, upper solution is filtered by vacuum using Buchner funnel, removes precipitation, and the acetonitrile for receiving tree moss concrete or oakmoss concrete is molten Liquid；Step 2, the sample solution that step 1 obtains removed into acetonitrile solvent therein by Rotary Evaporators, obtained to be separated Sample；Step 3, wet method dress post：Taking 100~300 mesh silica gel, the mixing for adding appropriate petroleum ether and ethyl acetate is molten in beaker Agent is continuously poured into silicagel column, using 40~200cm of column length, 4~50cm of diameter as the eluant, eluent configured after being sufficiently stirred Silicagel column；Step 4, the sample to be separated for obtaining step 2 are dissolved with ethyl acetate, and solution is slowly dropped to silicagel column upper surface, Opening regulating valve makes sample solution fully enter in silica gel；Step 5, from the post eluant, eluent suitable for reading for being slowly added into step 3, observe the change of colour band, treat that the leading portion yellow band of sample reaches Behind the bottom of silicagel column, yl moiety colour band is received with sample bottle, after chromatography terminates, is removed according to the method for step 2 therein Solvent, obtain one-level sample solution to be separated；Step 6,100~300 mesh silica gel are taken in beaker, add the mixed solvent of appropriate petroleum ether and ethyl acetate as configuration Good eluant, eluent, is continuously poured into silicagel column after being sufficiently stirred, using 40~200cm of column length, 3~20cm of diameter silicagel column；Step 7, eluant, eluent of the sample that step 5 obtains in step 6 dissolved, solution is slowly dropped to the silicagel column of step 6 Upper surface, opening regulating valve makes sample solution fully enter in silica gel, then adds the eluent sample of step 6；Step 8, after reaching the bottom of pillar after the colour band forward position of sample, efflux is received with triangular flask, with thin layer silica gel plate point Sample method detects chromatographic solution, judges whether target components flow out under uviol lamp, when the component that sample has UV absorption flows out, changes Eluent is received with sample bottle, untill all components for having UV absorption all elute, after eluent removing solvent i.e. For object aroma component divaricatic acid ethyl ester.
- 2. the separation method of aroma component divaricatic acid ethyl ester, its feature in tongue delicate fragrance type spices as claimed in claim 1 It is：Described silicagel column is equipped with tetrafluoroethene regulating valve and core.
- 3. the separation method of aroma component divaricatic acid ethyl ester, its feature in tongue delicate fragrance type spices as claimed in claim 1 It is：The mass ratio of raw material and acetonitrile is 1 in step 1:2.5~5.
- 4. the separation side of aroma component divaricatic acid ethyl ester in the tongue delicate fragrance type spices as described in claim any one of 1-3 Method, it is characterised in that：In step 3, described eluant, eluent is petroleum ether and ethyl acetate mixed solvent, petroleum ether and ethyl acetate Volume ratio be 9~15:1.
- 5. the separation side of aroma component divaricatic acid ethyl ester in the tongue delicate fragrance type spices as described in claim any one of 1-3 Method, it is characterised in that：In step 6, described eluant, eluent is petroleum ether and ethyl acetate mixed solvent, petroleum ether and ethyl acetate Volume ratio be 18~25:1.
- 6. the separation side of aroma component divaricatic acid ethyl ester in the tongue delicate fragrance type spices as described in claim any one of 1-3 Method, it is characterised in that：Step 4 is 1 with the material used in the column chromatography in step 7 and the mass ratio of silica gel:4~1:80.
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| CN106706794B (en) * | 2017-01-04 | 2018-12-11 | 江苏中烟工业有限责任公司 | A kind of method of main tongue fur faint scent characteristic chicken flavor substance in quantitative analysis ramuscule cigarette mainstream flue gas |
| CN111116371B (en) * | 2019-12-23 | 2022-02-01 | 华宝香精股份有限公司 | Novel moss fen-flavor compound 4-methoxy ethyl olivetolate, preparation method and application thereof |
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| DE3682821D1 (en) * | 1985-05-21 | 1992-01-23 | Shiseido Co Ltd | METHOD FOR PRODUCING A HYPOALLERGENIC MOSS OIL. |
| CN102041174B (en) * | 2011-01-07 | 2012-05-30 | 江苏中烟工业有限责任公司 | Preparation method of moss-scented tobacco flavor and application of moss-scented cigarette flavor in cigarette flavoring |
| CN102351706B (en) * | 2011-08-04 | 2013-08-07 | 江苏中烟工业有限责任公司 | Method for synthesizing ethyldivaricatinate and application of ethyldivaricatinate |
| CN103333743B (en) * | 2013-07-10 | 2014-06-11 | 江苏中烟工业有限责任公司 | Essence with moss faint scent and applications thereof |
| CN104155395B (en) * | 2014-08-15 | 2016-04-27 | 江苏中烟工业有限责任公司 | A kind of high speed adverse current chromatogram method for separating of terpenes component in tree moss concrete |
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