CN105481818B - A kind of flavouring humectation isocoumarin class compound and its preparation method and application - Google Patents
A kind of flavouring humectation isocoumarin class compound and its preparation method and application Download PDFInfo
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- CN105481818B CN105481818B CN201510810018.2A CN201510810018A CN105481818B CN 105481818 B CN105481818 B CN 105481818B CN 201510810018 A CN201510810018 A CN 201510810018A CN 105481818 B CN105481818 B CN 105481818B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/76—Benzo[c]pyrans
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- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
- A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
- A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
- A24B15/18—Treatment of tobacco products or tobacco substitutes
- A24B15/28—Treatment of tobacco products or tobacco substitutes by chemical substances
- A24B15/30—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances
- A24B15/36—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring
- A24B15/40—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring having only oxygen or sulfur as hetero atoms
- A24B15/403—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring having only oxygen or sulfur as hetero atoms having only oxygen as hetero atoms
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Abstract
The invention discloses a kind of isocoumarin class compound, which is named as：Heterochromatic alkene -6- the alcohol of 5- ((E) -4- hydroxy-3-methyls-butyl -2- alkene) -3- (methylol) -1H-, molecular formula C15H18O4, there are following structuresThe invention also discloses the preparation methods and purposes of above-mentioned isocoumarin class compound.It is demonstrated experimentally that the isocoumarin class compound of the present invention has the purposes for improving cigarette smoking quality；It is matched in appropriate proportions with humectant simultaneously, there is good physics and sense organ humectation effect to cigarette, and can soft cigarette smoke, the mellow and full sense of raising cigarette smoke and comfort and the effect for assigning cigarette smoke faint scent.
Description
Technical field
The invention belongs to technical field of tobacco chemistry, and in particular to an unusually sweet smell beans that extract for the first time in a kind of cigarette from drying
Chlorins compound.Meanwhile it being answered the invention further relates to the preparation method of the isocoumarin class compound and its combining with humectant
With the purposes improved in cigarette smoking quality.
Background technology
Tobacco is the plant that chemical composition is the most complicated in the world, and secondary metabolite is very abundant, by decades
Research, people identify the monomer chemistries substance come just more than more than 3000 kind from tobacco at present, but also there are many ingredient still
It does not identify and.It has been widely recognized although Smoking is harmful to your health, tobacco still has by force thousands of consumer
Big attraction, except nicotine it is additive in addition to, abundant fragrance matter also plays an important role in tobacco.
Isocoumarin is the basic structure of some natural products, is distributed widely in nature, and type is various.People once used
A variety of methods synthesize such compound.The derivative of such compound removes with antibacterial, anti-inflammatory, anticancer, inhibits egg
Outside the white physiology such as enzyme and weeding and bioactivity, some compounds also have fragrance characteristic outstanding, are important fragrance chemical combination
Object.Structure-activity relationship in order to study this kind of compound finds compound with practical value, and people also carry out such compound
A large amount of bioactivity research.The present invention from drying cigarette it is isolated it is a kind of have improve cigarette smoking quality function
Relevant report is not yet seen in isocoumarin class compound, the compound.
Mainly use the polyhydroxy substances such as glycerine, propylene glycol, sorbierite as humectant, humectant in China's cigarette industry
Main purpose be to maintain the moisture content of pipe tobacco in process, improve the resist processing of pipe tobacco, but above-mentioned humectant at
There is prodigious association with its formulation composition and its blending in product smoking property of cigarette comfort level.The present invention passes through a kind of isolated tool
Having improves the isocoumarin class compound of cigarette smoking quality function, which improves the suction product of cigarette with humectant cooperation
Matter also has no relevant report.
Invention content
The purpose of the present invention is to provide a kind of new isocoumarin class compounds.
It is a further object to provide a kind of methods preparing the isocoumarin class compound.
The present invention also aims to provide purposes of the isocoumarin class compound in improving cigarette smoking quality.
Unless otherwise indicated, the percentage employed in the present invention is weight percent.
First aspect present invention is related to a kind of new isocoumarin class compound isolated from drying cigarette, under having
State structural formula：
The compound is named as：5- ((E) -4- hydroxy-3-methyls-butyl -2- alkene) -3- (methylol) -1H- is heterochromatic
Alkene -6- alcohol, English are entitled：[5-((E)-4-hydroxy-3-methylbut-2-enyl)-3-(hydroxymethyl)-1H-
isochromen-6-ol], molecular formula C15H18O4, it is light yellow gum object.
Second aspect of the present invention is related to a kind of preparation of the isocoumarin class compound according to a first aspect of the present invention
Method, the preparation method include the following steps：
(1) tobacco extract medicinal extract is prepared:To dry cigarette tobacco leaf as raw material, tobacco leaf is crushed or is cut into segment, is used in combination the
One solvent soaking simultaneously extracts the tobacco leaf 3~5 times, every time for 24 hours~72h, is obtained after extracting solution is merged, filters and concentrated described
Tobacco extract medicinal extract；Wherein described first solvent is the mixture selected from methanol, the organic solvent of ethyl alcohol or acetone and water, when
When first solvent is methanol or the mixture of ethyl alcohol and water, wherein methanol or ethyl alcohol account for the 80wt% of first solvent~
100wt%, when first solvent is the mixture of acetone and water, wherein acetone account for the 60wt% of first solvent~
90wt%；And first solvent：Tobacco=(2-4):(4-6), weight ratio；
(2) silica gel column chromatography：After above-mentioned tobacco extract medicinal extract is mixed with 160~300 mesh silica gel of its 2-4 times of weight
Then dry column-packing is followed successively by 1 with volume ratio:0,20:1,9:1,8:2,7:3,6:4,1:1 and 1:2 chloroform-acetone solution into
Row gradient elution will volume ratio be wherein 8:The eluent obtained when 2 chloroform-acetone solution elution is known as the first eluent；
(3) high pressure liquid chromatography isolates and purifies：Above-mentioned first eluent is passed through high pressure liquid chromatography to isolate and purify,
The high pressure liquid chromatography uses 21.2mm × 250mm, 5 μm of C18Chromatographic column, flow rate of mobile phase 20mL/min, mobile phase are
55% methanol, UV detector Detection wavelength are 315nm, each 200 μ L of sample introduction of the first eluent, chromatographic peak after each sample introduction
Corresponding eluent when retention time is 28.2min, referred to as the second eluent remove second eluent after solvent to obtain the final product
The isocoumarin class compound.
In a preferred embodiment of the present invention, further include the steps that purifying further below：It will be in the high pressure liquid
The isocoumarin class compound obtained after phase chromatographic isolation is again dissolved in pure methanol, and using pure methanol as mobile phase, leads to
It crosses gel column and carries out chromatography, the isocoumarin class compound further purified.
In a preferred embodiment of the present invention, in step (2), before being mixed with 160~300 mesh silica gel, first
By the second solvent dissolving selected from pure methanol, straight alcohol or pure acetone of its 1.5~3 times of weight of the tobacco extract medicinal extract
Afterwards with 80~100 mesh silica gel mixed samples of 0.8~1.2 times of weight for tobacco extract medicinal extract.
Third aspect present invention, which is related to the isocoumarin class compound described according to a first aspect of the present invention, is improving cigarette
Purposes in suction quality.
Fourth aspect present invention is related to the isocoumarin class compound described according to a first aspect of the present invention and is used for soft volume
Cigarette flue gas improves the mellow and full sense of cigarette smoke and comfort or the purposes for assigning cigarette smoke faint scent with humectant synergistic effect.
Compared with prior art, the invention has the advantages that：The isocoumarin class compound of the present invention is for the first time
It is separated, structure novel.Show that the compound of the present invention is bright to cigarette flavouring upgrading effect through cigarette addition experiment
It is aobvious, it can be obviously improved cigarette flavor concentration, increase perfume quantity, improve cigarette sense organ suction quality, had as cigarette additive
Wide application prospect.The compound of the present invention matches in appropriate proportions with humectant, has the use for improving cigarette smoking quality
On the way, there is good physics and sense organ humectation effect, and the soft cigarette smoke of energy, the mellow and full sense for improving cigarette smoke to cigarette
With comfort and have the effect of assign cigarette smoke faint scent.The compounds of this invention is simple in structure, can be obviously improved cigarette pumping
Quality is inhaled, can be used as the guiding compound of tobacco aromaticss research and development and with humectant with the use of improvement cigarette smoking quality
It is prepared by new additive.
Description of the drawings
Fig. 1 is the carbon-13 nmr spectra of isocoumarin class compound of the present invention；
Fig. 2 is the nuclear magnetic resonance spectroscopy of isocoumarin class compound of the present invention；
Fig. 3 is the main HMBC relevant indicators of isocoumarin class compound of the present invention.
Specific implementation mode
The structure of isocoumarin class compound prepared by the present invention is to determine to come by the following method.Of the present inventionization
Conjunction object is light yellow gum object；Ultraviolet spectra (solvent is methanol), λmax(logε)210(3.65),270(3.36),292
(3.14),315(3.27)nm；Infrared spectrum (pressing potassium bromide troche) νmax 3422,3068,2963,2856,1612,1573,
1463,1354,1165,1054cm-1；High resolution mass spectrum (HRESIMS) provides quasi-molecular ion peak m/z 285.1109[M+Na]+
(calculated value 285.1103).In conjunction with1H and13C H NMR spectroscopies provide a molecular formula C15H18O4, degree of unsaturation 7.The compound
Spectral data and known compound versicolol B are closely similar, are a difference in that in known compound versicolol B
Two methyl and a methoxyl group respectively by the compounds of this invention two oxidation methylene and a hydroxyl replace.These
Supposition is further confirmed by HMBC correlations.In HMBC spectrums, it is observed that H2- 9 is related to C-3's and C-4, H2-
4'With C-2', C-3'And C-5'Correlation and Ar-OH and C-6, C-7 it is related to C-5's, to prove three hydroxyls connect respectively
It is connected on the C-9 of compound, C-4'On C-6.Meanwhile it can also be observed that H in ROESY spectrums2-4'With H-2'Correlation, from
And it is E configuration to prove isopentene group.So far the structure of this compound is determined.
1. compound of table1H NMR and13C NMR datas (CCl3)
The compounds of this invention is separated for the first time, is determined as by above-mentioned nuclear magnetic resonance and measuring method of mass spectrum different
Coumarin kind compound, and characterize its concrete structure.Show through cigarette addition experiment：The compound has improvement cigarette smoking
The purposes of quality, and being used in combination with humectant, can soft cigarette smoke, improve flue gas mellow and full sense and comfort, also
Have the effect of assigning cigarette smoke faint scent.The compounds of this invention is simple in structure, can be obviously improved cigarette smoking quality, can be used as
It is prepared by the guiding compound of tobacco aromaticss research and development and the new additive that improvement cigarette smoking quality is used in combination with humectant.
The present invention is described in further detail with reference to the accompanying drawings and examples, but not in any way to the present invention
Limit, be based on present invention teach that made by any transformation or improvement, each fall within protection scope of the present invention.
The raw materials used in the present invention is not limited by area and kind, and the present invention may be implemented in the tobacco in any source place, under
With the tobacco material of the cigarette industry Co., Ltd different sources in Yunnan, the present invention will be further described in face.Unless
It is otherwise noted, the percentage employed in the present invention is weight percent.In the examples where no specific technique or condition is specified,
It is carried out according to technology or condition described in document in the art or according to product description.Agents useful for same or instrument are not noted
Bright production firm person, being can be by buying the conventional products obtained.If the solution in the present invention only gives solute, do not have
There is open solvent, then those skilled in the art should know that solvent is water.Pure methanol refers to 100% methanol, straight alcohol in the present invention
Refer to 100% ethyl alcohol, pure acetone refers to 100% acetone.
Embodiment 1
A kind of isocoumarin class compound C15H18O4Preparation method, specifically include following steps：
(1) tobacco extract medicinal extract is prepared:Using airing tobacco as raw material, tobacco leaf is crushed or is cut into segment, is used in combination first
Solvent soaking simultaneously extracts the tobacco leaf 4 times, each 54h, and the tobacco extract is obtained after extracting solution is merged, filters and concentrated
Medicinal extract；Wherein described first solvent is the mixture selected from methanol, the organic solvent of ethyl alcohol or acetone and water, when described first molten
When agent is methanol or the mixture of ethyl alcohol and water, wherein methanol or ethyl alcohol account for the 95wt% of first solvent, when described first molten
When agent is the mixture of acetone and water, wherein acetone accounts for the 70wt% of first solvent；And first solvent：Tobacco=3:5, weight
Than；
(2) silica gel column chromatography：By the tobacco extract medicinal extract its 2.5 times of weight selected from pure methanol, straight alcohol or
Pure acetone the second solvent dissolving after with for tobacco extract medicinal extract 1.2 times of weight 80~100 mesh silica gel mixed samples, then with cigarette
Dry column-packing after the 250 mesh silica gel mixing of careless 3 times of weight of extract medicinal extract, is then followed successively by 1 with volume ratio:0,20:1,9:1,
8:2,7:3,6:4,1:1 and 1:2 chloroform-acetone solution carries out gradient elution, will volume ratio be wherein 8:2 chloroform-acetone
The eluent that solution obtains when eluting is known as the first eluent；
(3) high pressure liquid chromatography isolates and purifies：Above-mentioned first eluent is passed through high pressure liquid chromatography to isolate and purify,
The high pressure liquid chromatography uses 21.2mm × 250mm, 5 μm of C18Chromatographic column, flow rate of mobile phase 20mL/min, mobile phase are
55% methanol, UV detector Detection wavelength are 315nm, each 200 μ L of sample introduction of the first eluent, chromatographic peak after each sample introduction
Corresponding eluent when retention time is 28.2min, referred to as the second eluent remove second eluent after solvent to obtain the final product
The isocoumarin class compound.
The preparation method further includes the steps that purifying further below：It will be obtained after the high pressure liquid chromatography detaches
To the isocoumarin class compound be again dissolved in pure methanol, and using pure methanol as mobile phase, chromatographed by gel column
Separation, the isocoumarin class compound further purified.
Embodiment 2
For drying cigarette sample source used in Yunnan Yuxi, kind is Yuxi river and mountain cigarette.By tobacco leaf sampling 2.0kg crush with
95% methanol extracts 5 times, and for 24 hours, extracting solution merges for extraction every time, and tobacco extract medicinal extract 95g is concentrated under reduced pressure to obtain in filtering.It will
Its 2.0 weight multiple of above-mentioned tobacco extract medicinal extract pure methanol dissolving after use 120g the thick silica gel mixed sample of 100 mesh, then with
Dress column carries out silica gel column chromatography after the 160 mesh silica gel mixing of 0.6kg, is 1 with volume proportion:0,20:1,9:1,8:2,7:3,6:
4,1:1,1:2 chloroform-acetone gradient elution, TLC monitorings merge identical part, obtain 8 parts, wherein volume proportion is
8:The peace prompt logical sequence 1,100 half preparative high-performance liquid chromatographic separation of 2 chloroform-acetone elution fraction, is flowing with 55% methanol
Phase, it is stationary phase, flow rate of mobile phase 20ml/min, ultraviolet detection that Zorbax SB-C18 (21.2 × 250mm, 5 μm), which prepare column,
Device Detection wavelength is 315nm, 200 μ L of each sample introduction, is collected corresponding when chromatographic peak retention time is 28.2min after each sample introduction
Eluent, remove solvent after repeatedly cumulative；Products therefrom is dissolved with pure methanol again, then using pure methanol as mobile phase, is used
Sephadex LH-20 gel filtration chromatographies detach to get the isocoumarin class compound further purified.
Wherein, it when gradient elution, when the elution of the mixed solvent of each ratio, is eluted to until no ingredient washes down, then
Change the mixed solvent of next ratio.
Embodiment 3
For drying cigarette sample source used in Dali, kind is that cigarette is stepped in Yunlong day.Tobacco leaf sampling 3.5kg is shredded, with
95% ethyl alcohol extracts 4 times, extracts 48h every time, and extracting solution merges, and tobacco extract medicinal extract 245g is concentrated under reduced pressure to obtain in filtering.It will
Its 2.0 times of weight of above-mentioned tobacco extract medicinal extract pure methanol dissolving after use 250g the thick silica gel mixed sample of 80 mesh, then with 1.2kg
200 mesh silica gel mixing after dress column carry out silica gel column chromatography, with volume proportion be 1:0,20:1,9:1,8:2,7:3,6:4,1:1,
1:2 chloroform-acetone gradient elution, TLC monitorings merge identical part, obtain 8 parts, and wherein volume proportion is 8:2
The peace prompt logical sequence 1,100 half preparative high-performance liquid chromatographic separation of chloroform-acetone elution fraction, using 55% methanol as mobile phase,
It is stationary phase, flow rate of mobile phase 20ml/min, UV detector that Zorbax SB-C18 (21.2 × 250mm, 5 μm), which prepare column,
Detection wavelength is 315nm, 200 μ L of each sample introduction, is collected corresponding when chromatographic peak retention time is 28.2min after each sample introduction
Eluent removes solvent after repeatedly adding up；Products therefrom is dissolved with pure methanol again, then using pure methanol as mobile phase, is used
Sephadex LH-20 gel filtration chromatographies detach to get the isocoumarin class compound further purified.
Wherein, it when gradient elution, when the elution of the mixed solvent of each ratio, is eluted to until no ingredient washes down, then
Change the mixed solvent of next ratio.
Embodiment 4
For drying cigarette sample source used in Kunming, Yunnan, kind is Songming safflower cigarette.Tobacco leaf sampling 5kg is crushed, with
75% acetone ultrasonic extraction 3 times extracts 72h every time, and extracting solution merges, and tobacco extract medicinal extract is concentrated under reduced pressure to obtain in filtering
385g.The thick silica gel mixed sample of 90 mesh of 400g will be used after the pure methanol dissolving of its 1.6 times of weight of above-mentioned tobacco extract medicinal extract, then
Column is filled after being mixed with the 180 mesh silica gel of 2.4kg and carries out silica gel column chromatography, is 1 with volume proportion:0,20:1,9:1,8:2,7:3,
6:4,1:1,1:2 chloroform-acetone gradient elution, TLC monitorings merge identical part, obtain 8 parts, wherein volume proportion
It is 8:The peace prompt logical sequence 1,100 half preparative high-performance liquid chromatographic separation of 2 chloroform-acetone elution fraction, is flowing with 55% methanol
Phase, it is stationary phase, flow velocity 20ml/min, UV detector detection that Zorbax SB-C18 (21.2 × 250mm, 5 μm), which prepare column,
Wavelength is 315nm, 200 μ L of each sample introduction, collects elution corresponding when chromatographic peak retention time is 28.2min after each sample introduction
Liquid removes solvent after repeatedly adding up；Products therefrom is dissolved with pure methanol again, then using pure methanol as mobile phase, is used
SephadexLH-20 gel filtration chromatographies detach to get the isocoumarin class compound further purified.
Wherein, it when gradient elution, when the elution of the mixed solvent of each ratio, is eluted to until no ingredient washes down, then
Change the mixed solvent of next ratio.
The identification of embodiment 5- compound structures
Compound prepared by Example 1, the structure for the isocoumarin class compound that method described above is prepared pass through
Following methods are measured.The compounds of this invention is light yellow gum object；Ultraviolet spectra (solvent is methanol), λmax(logε)210
(3.65),270(3.36),292(3.14),315(3.27)nm；Infrared spectrum (pressing potassium bromide troche) νmax 3422,3068,
2963,2856,1612,1573,1463,1354,1165,1054cm-1；High resolution mass spectrum (HRESIMS) provides quasi-molecular ion
Peak m/z 285.1109[M+Na]+(calculated value 285.1103).In conjunction with1H and13C H NMR spectroscopies provide a molecular formula C15H18O4, no
Saturation degree is 7.The spectral data and known compound versicolol B of the compound are closely similar, are a difference in that knownization
Two methyl and a methoxyl group closed in object versicolol B aoxidize methylene by two in the compounds of this invention respectively
Replaced with a hydroxyl.These suppositions are further confirmed by HMBC correlations.In HMBC spectrums, it is observed that
H2- 9 is related to C-3's and C-4, H2-4'With C-2', C-3'And C-5'Correlation and Ar-OH and C-6, C-7 and C-5 phase
It closes, to prove that three hydroxyls are connected to the C-9, C-4&apos of compound;On C-6.Meanwhile it can also be seen in ROESY spectrums
Observe H2-4'With H-2'Correlation, to prove isopentene group be E configuration.So far the structure of this compound is determined.
Embodiment 6-8
The compound that respectively prepared by Example 2-4 is light yellow gum object.Assay method is same as Example 5, confirms
Compound prepared by embodiment 2-4 is isocoumarin class compound 5- ((E) -4- hydroxy-3-methyls-butyl -2- alkene) -3-
Heterochromatic alkene -6- the alcohol of (methylol) -1H-.
Embodiment 9- flavorings are tested
The isocoumarin class compound of any preparation in Example 1-4 carries out the perfuming effect experiment of cigarette, tests feelings
Condition is as follows：
It is the Red River Hong Yun group product " purple cloud and mist " Cigarette for addition cigarette, every pipe tobacco weight is 0.68g.
To be not added with " purple cloud and mist " Cigarette of any other substance as blank control.By above-mentioned isocoumarin class compound ethyl alcohol
Aqueous solution is made into the solution of 0.68% (m/v), is injected respectively with essence and flavoring agent with 5 μ L, 10 μ L, 15 μ L, 20 μ L, tetra- injection volumes
Machine is added in different " purple cloud and mist " Cigarette pipe tobaccos, then by cigarette sample (22 ± 1) DEG C, relative humidity 60% ±
48h is balanced under the conditions of 2%, is respectively obtained Cigarette A1, B1, C1 and D1, is smoked panel test for expert sensory.
The Cigarette and blank control cigarette that the isocoumarin class compound of the present invention will be added to carry out organoleptic quality
Evaluation, the results showed that, isocoumarin class compound of the invention is with obvious effects for cigarette flavouring upgrading, can be obviously improved cigarette
Fragrance level increases perfume quantity, improves cigarette sense organ suction quality, has broad application prospects as cigarette additive.
The synergistic effect of embodiment 10- and humectant
The isocoumarin class compound of any preparation in Example 1-4 carries out them to cigarette sensory quality with humectant
Synergy experiment, test situation is as follows：
It is the Red River Hong Yun group product " purple cloud and mist " Cigarette for addition cigarette, every pipe tobacco weight is 0.68g.
To be not added with " purple cloud and mist " Cigarette of any other substance as blank control.By above-mentioned isocoumarin class compound humectation
Agent is made into the solution of 0.68% (m/v), is added respectively with 5 μ L, 10 μ L, 15 μ L, 20 μ L, tetra- injection volume essence and flavoring agent injectors
It adds in different " purple cloud and mist " Cigarette pipe tobaccos, then by cigarette sample in (22 ± 1) DEG C, relative humidity 60% ± 2%
Under the conditions of balance 48h, respectively obtain Cigarette A2, B2, C2 and D2.Above-mentioned isocoumarin class compound is made into humectant
The solution of 0.68% (m/v) is added to not with 5 μ L, 10 μ L, 15 μ L, 20 μ L, tetra- injection volumes with essence and flavoring agent injector respectively
In same " purple cloud and mist " Cigarette pipe tobacco, then it is separately added into the pipe tobacco of above-mentioned kinds of cigarettes cigarette and accounts for tobacco quality
0.1%, 0.4%, 0.7%, 1% humectant.The wherein described humectant can be any in glycerine, propylene glycol or sorbierite
Kind or their mixture.Then cigarette sample is balanced into 48h under the conditions of (22 ± 1) DEG C, relative humidity 60% ± 2%.Point
Cigarette A3, B3, C3 and D3 are not obtained.
By the Cigarette for the isocoumarin class compound for being added to the present invention respectively while being added to an unusually sweet smell of the invention
The Cigarette and blank control cigarette of beans chlorins compound and humectant carry out organoleptic quality evaluations, and smoking result shows：
The isocoumarin class compound and humectant that the present invention is added in cigarette there is good physics and sense organ humectation to make cigarette
With, can soft cigarette smoke, improve flue gas mellow and full sense and comfort, also have the effect of imparting cigarette smoke faint scent.It can
Seeing has synergy between the compound and humectant.Isocoumarin class compound exists relative to the optimum addition of pipe tobacco
Between 0.05 ‰~0.15 ‰, humectant relative to pipe tobacco optimum addition between 0.1%~0.7%.
The compounds of this invention is simple in structure, can be obviously improved cigarette smoking quality, can be used as the guide of tobacco aromaticss research and development
Property compound and with humectant with the use of improve cigarette smoking quality new additive prepare.
Claims (4)
1. a kind of isocoumarin class compound improves the mellow and full sense of cigarette smoke for soft cigarette smoke, with humectant synergistic effect
With comfort or assign cigarette smoke faint scent purposes, wherein the isocoumarin class compound have following structural formula：
The compound is named as：5- ((E) -4- hydroxy-3-methyls-butyl -2- alkene) heterochromatic alkene -6- of -3- (methylol) -1H-
Alcohol, molecular formula C15H18O4。
2. purposes according to claim 1, wherein the isocoumarin class compound passes through the preparation that comprises the steps of
It is prepared by method：
(1) tobacco extract medicinal extract is prepared:Using airing tobacco as raw material, airing tobacco is crushed or is cut into segment, is used in combination first
Solvent soaking simultaneously extracts the tobacco leaf 3~5 times, every time for 24 hours~72h, and the cigarette is obtained after extracting solution is merged, filters and concentrated
Careless extract medicinal extract；Wherein described first solvent is the mixture selected from methanol, the organic solvent of ethyl alcohol or acetone and water, works as institute
When to state the first solvent be methanol or the mixture of ethyl alcohol and water, wherein methanol or ethyl alcohol account for the 80wt% of first solvent~
100wt%, when first solvent is the mixture of acetone and water, wherein acetone account for the 60wt% of first solvent~
90wt%；And first solvent：Tobacco=(2-4):(4-6), weight ratio；
(2) silica gel column chromatography：Dry method after above-mentioned tobacco extract medicinal extract is mixed with 160~300 mesh silica gel of its 2-4 times of weight
Column is filled, is then followed successively by 1 with volume ratio:0,20:1,9:1,8:2,7:3,6:4,1:1 and 1:2 chloroform-acetone solution carries out ladder
Degree elution will volume ratio be wherein 8:The eluent obtained when 2 chloroform-acetone solution elution is known as the first eluent；
(3) high pressure liquid chromatography isolates and purifies：Above-mentioned first eluent is passed through high pressure liquid chromatography to isolate and purify, the height
Pressure liquid chromatography uses 21.2mm × 250mm, 5 μm of C18Chromatographic column, flow rate of mobile phase 20mL/min, mobile phase are 55%
Methanol, UV detector Detection wavelength are 315nm, each 200 μ L of sample introduction of the first eluent, when chromatographic peak retains after each sample introduction
Between corresponding eluent when being 28.2min, referred to as the second eluent removes second eluent after solvent up to described different
Coumarin kind compound.
3. purposes according to claim 2, wherein the preparation method further includes the steps that purifying further below：It will be
The isocoumarin class compound that the high pressure liquid chromatography separation obtains later is again dissolved in pure methanol, and is with pure methanol
Mobile phase carries out chromatography, the isocoumarin class compound further purified by gel column.
4. in purposes according to claim 2, wherein step (2), before being mixed with 160~300 mesh silica gel, first
By the second solvent dissolving selected from pure methanol, straight alcohol or pure acetone of its 1.5~3 times of weight of the tobacco extract medicinal extract
Afterwards with 80~100 mesh silica gel mixed samples for 0.8~1.2 times of weight of tobacco extract medicinal extract.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201510810018.2A CN105481818B (en) | 2015-11-20 | 2015-11-20 | A kind of flavouring humectation isocoumarin class compound and its preparation method and application |
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| CN105906566B (en) * | 2016-05-19 | 2018-08-03 | 云南中烟工业有限责任公司 | A kind of alkaloid compound, preparation method and use with antibacterial activity in tobacco |
| CN110514784A (en) * | 2019-07-30 | 2019-11-29 | 云南中烟工业有限责任公司 | The method and purposes of fragrance interaction between a kind of two kinds of sour aroma substances of evaluation |
| CN111533720B (en) * | 2020-05-09 | 2022-05-10 | 云南中烟工业有限责任公司 | Pyranolide compound, preparation method thereof, additive containing pyranolide compound and application of pyranolide compound |
| CN114805276B (en) * | 2022-03-14 | 2023-07-14 | 云南中烟工业有限责任公司 | Isochromene compound and preparation method and application thereof |
| CN114920723B (en) * | 2022-03-14 | 2023-07-14 | 云南中烟工业有限责任公司 | Chromene compound with antioxidant activity and preparation method and application thereof |
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