CN106380473B - A kind of lactone compound, preparation method and use - Google Patents
A kind of lactone compound, preparation method and use Download PDFInfo
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- CN106380473B CN106380473B CN201610743725.9A CN201610743725A CN106380473B CN 106380473 B CN106380473 B CN 106380473B CN 201610743725 A CN201610743725 A CN 201610743725A CN 106380473 B CN106380473 B CN 106380473B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
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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
Abstract
The invention discloses a kind of lactone compound, has following structure：The Compound nomenclature is 8,9 dihydro 7,7 methyl 1H furans [3,4 f] chromene 3 (7H) ketone, molecular formula C13H14O3.Purposes the invention also discloses the preparation method of above-claimed cpd and for improving cigarette smoking quality.
Description
Technical field
The invention belongs to technical field of tobacco chemistry, and in particular to extract obtained lactone in a kind of cigarette from drying first
Compound.Meanwhile the invention further relates to the preparation method of the compound and the use in conjunction of itself and humectant to improve cigarette smoking
Purposes in 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 material just kind more than 3000, and also many compositions are still come from tobacco at present
Do not identify and.It has been widely recognized although Smoking is harmful to your health, tobacco still has by force to thousands of consumer
Big attraction, except nicotine it is additive in addition to, in tobacco enrich fragrance matter also play an important role.
Lactone refers to the ester type compound that the carboxyl in same molecule is dehydrated and formed with hydroxyl interaction, such chemical combination
Thing generally existing in natural plants, also there is the document report for being widely present such compound in natural plants, except with wide
General pharmacological action, lactone or a kind of important volatile compound, are naturally occurring in various fruit and spice berry, such
Compound has been widely used in the formula of the flavoring essences such as various beverages, bakery product.The present invention separates from drying cigarette
A kind of lactone compound for having and improving cigarette smoking quality function is arrived, relevant report is not yet seen in the compound.
Mainly using polyhydroxy substances such as glycerine, propane diols, sorbierites as humectant, the main mesh of humectant in China's cigarette industry
The moisture content in the pipe tobacco in process is maintained, improve the resist processing of pipe tobacco, but above-mentioned humectant is inhaled to finished cigarettes
Have in food comfort level with its formulation composition and its blending it is very big associate, by it is isolated it is a kind of have improve cigarette smoking
The lactone compound of quality function, the compound coordinate the suction quality for improving cigarette also to have no relevant report with humectant.
The content of the invention
It is an object of the invention to provide a kind of new lactone compound.
It is a further object to provide a kind of method for preparing the lactone compound.
The present invention also aims to provide purposes of the lactone compound in cigarette smoking quality is improved.
Unless otherwise indicated, the percentage employed in the present invention is percetage by weight.
The first aspect of the present invention is related to isolates a kind of new lactone compound from drying cigarette, and it has following knots
Structure formula：
The compound is named as：8,9- dihydro -7,7- methyl isophthalic acid H furans [3,4-f] chromene -3 (7H) -one, English name
For：8,9-dihydro-7,7-dimethyl-1H-furo[3,4-f]chromen-3(7H)-one；Molecular formula is C13H14O3, it is
Light yellow gum thing.
The second aspect of the present invention is related to a kind of preparation of lactone compound described according to the first aspect of the invention
Method, the preparation method comprise 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, and with the
One solvent soaking simultaneously extracts the tobacco leaf 3~5 times, each 24h~72h, and extract solution is merged, filtered and is obtained after concentrating described
Tobacco extract medicinal extract；Wherein described first solvent is the mixture selected from methanol, the organic solvent of ethanol or acetone and water, when
When first solvent is methanol or the mixture of ethanol and water, wherein methanol or ethanol 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
Dry column-packing, then it 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 is entered
Row gradient elution, collected volume 8:The eluent obtained during 2 chloroform-acetone solution elution, referred to as the first eluent；
(3) high pressure liquid chromatography isolates and purifies：By the first above-mentioned eluent be passed through high pressure liquid chromatography separate it is pure
Change, the high pressure liquid chromatography uses 21.2mm × 250mm, 5 μm of C18Chromatographic column, flow rate of mobile phase 20mL/min, mobile phase
For 54wt% methanol, UV-detector Detection wavelength is 315nm, each μ L of sample introduction 200 of the first eluent, color after each sample introduction
Spectral peak retention time eluent corresponding when being 26.8min, referred to as the second eluent, after the second eluent desolvation
Produce the lactone compound.
In a preferred embodiment of the present invention, the step of it also includes purifying further below：Will be in the high pressure liquid
The lactone compound obtained after phase chromatographic isolation is again dissolved in pure methanol, and using pure methanol as mobile phase, by solidifying
Glue post carries out chromatography, the lactone compound further purified.
In a preferred embodiment of the present invention, in step (2), before being mixed with 160~300 mesh silica gel, first
The tobacco extract medicinal extract the second solvent selected from pure methanol, straight alcohol or pure acetone of its 1.5~3 times of weight is dissolved
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 is related to lactone compound described according to the first aspect of the invention and taken out in improvement cigarette
Inhale the purposes in quality.
Fourth aspect present invention is related to lactone compound described according to the first aspect of the invention with humectant with suitable
When purposes of the proportions for lifting the flue gas fragrance of a flower.
Compared with prior art, the invention has the advantages that：The lactone compound of the present invention is to be divided first
Separate out what is come, structure is novel.Show that it is matched in appropriate proportions with humectant through cigarette addition experiment, having, which improves cigarette, takes out
The purposes of quality is inhaled, there is good physics and sense organ humectation to act on to cigarette, and the effect of the flue gas fragrance of a flower can be increased.
Brief description of the drawings
Fig. 1 is the carbon-13 nmr spectra of lactone compound of the present invention；
Fig. 2 is the proton nmr spectra of lactone compound of the present invention；
Fig. 3 is the main HMBC relevant indicators of lactone compound of the present invention.
Embodiment
The compounds of this invention is light yellow gum thing, high resolution mass spectrum HR-ESI-MS m/z:241.0848[M+Na]+(meter
Calculation value 241.0841, C13H14NaO3), with reference to1H and13C H NMR spectroscopies determine that molecular formula is C13H14O3, degree of unsaturation 7.Ultraviolet light
Spectrum has absorption maximum 210,278,315, illustrates aromatic ring structure in compound be present.IR, which is shown in molecular structure of compounds, carbonyl
Base (1725cm-1) and aromatic ring (1610,1562 and 1458cm-1).Compound1H and13C H NMR spectroscopies (table -1) show that it contains 13
Individual carbon and 14 hydrogen, including 11,2,3,4- quaternary phenyl ring (C-4~C-7, C-4a and C-7a, H-6 and H-7), 1 is humorous
Dimethyl dihydro chromene ring (C-8~C-12, H2-8、H2- 9 and H6- 11,12), an ester carbonyl group (δC168.8s) and an oxygen
Methylene (the δ of changeC72.7t δH5.45s).Its HMBC coherent signal is further analyzed, according to H2- 3 and C-1, C-4, C-4a,
It is benzofuran lactone structure that C-7a, H-7 and C-1, C-4a, C-7a HMBC related (figure -3), which can speculate compound,.Compound
HMBC spectrum in H can be observed2- 8 and C-4, C-5, C-4a；H2- 9 is long-range related to C-4's, can speculate humorous dimethyl dihydro color
Alkene ring is substituted in C-4 the and C-5 positions of compound, and C-8 positions carbon is connected to the C-4 positions of phenyl ring.So far, the structure of compound obtains
To determination, the Compound nomenclature is：8,9- dihydros -7,7- methyl isophthalic acid H furans [3,4-f] chromene -3 (7H) -one.
Infrared, the ultraviolet and mass spectrometric data of compound：UV(MeOH)λmax(logε)315(3.26)、278(3.68)、210
(4.15)nm；IR(KBr)λmax 3076、2918、1725、1610、1562、1458、1260、1123、1085、867、759cm-1；
ESIMS (positive ion mode) m/z 241 [M+Na]+；HRESIMS (positive ion mode) m/z 241.0848 [M+Na]+(calculated value
241.0841, C13H14NaO3)。
The compound of table -11H NMR and13C NMR datas (C5D5N)
The compounds of this invention is separated first, is defined as by above-mentioned nuclear magnetic resonance and measuring method of mass spectrum interior
Ester type compound, and characterize its concrete structure.Show through cigarette addition experiment：The compound has improvement cigarette smoking quality
Purposes, and can be used in combination with humectant, the effect of the flue gas fragrance of a flower can be increased.The compounds of this invention is simple in construction, improves volume
The effect of cigarette suction quality is obvious, improvement volume can be used in combination as the guiding compound of tobacco aromaticss research and development and with humectant
It is prepared by the new additive of cigarette suction quality.
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
It is any limitation as, based on present invention teach that any conversion or improvement made, each fall within protection scope of the present invention.
The present invention is raw materials used not to be limited by area and kind, and the tobacco in any source place can realize the present invention, 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 percetage by weight.In the examples where no specific technique or condition is specified,
Carried out according to the technology described by document in the art or condition 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% ethanol, pure acetone refers to 100% acetone.
Embodiment 1
A kind of lactone compound C13H14O3Preparation 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, and with first
Solvent soaking simultaneously extracts the tobacco leaf 4 times, each 54h, and extract solution is merged, filtered and the tobacco extract is obtained after concentrating
Medicinal extract；Wherein described first solvent is the mixture selected from methanol, the organic solvent of ethanol or acetone and water, when described first molten
When agent is methanol or the mixture of ethanol and water, wherein methanol or ethanol 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 with 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 the careless times of weight of extract medicinal extract 3, 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, and it is 8 to collect wherein volume:2 chloroform-acetone
The eluent that solution obtains when eluting, referred to as the first eluent；
(3) high pressure liquid chromatography isolates and purifies：By the first above-mentioned eluent be passed through high pressure liquid chromatography separate it is pure
Change, the high pressure liquid chromatography uses 21.2mm × 250mm, 5 μm of C18Chromatographic column, flow rate of mobile phase 20mL/min, mobile phase
For 54wt% methanol, UV-detector Detection wavelength is 315nm, each μ L of sample introduction 200 of the first eluent, color after each sample introduction
Spectral peak retention time eluent corresponding when being 26.8min, referred to as the second eluent, after the second eluent desolvation
Produce the lactone compound.
The step of preparation method also includes purifying further below：It will be obtained after the high pressure liquid chromatography separates
To the lactone compound be again dissolved in pure methanol, and using pure methanol as mobile phase, chromatography is carried out by gel column,
The lactone compound further purified.
Embodiment 2
For drying cigarette sample source used in Tengchong In Yunnan Province, kind is that Tengchong rises soft raw cigarette.By tobacco leaf sampling 2.0kg crush with
95% methanol extracts 5 times, extracts 24h every time, and extract solution merges, and filtering, be concentrated under reduced pressure to obtain tobacco extract medicinal extract 95g.Will
The above-mentioned tobacco extract medicinal extract thick silica gel mixed sample of 100 mesh that 120g is used after the pure methanol dissolving of its 2.0 weight multiple, then with
Post is filled after 0.6kg 160 mesh silica gel mixing 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 is
8:2 chloroform-acetone elution fraction pacifies the prompt preparative high-performance liquid chromatographic of logical sequence 1,100 half separation, using 54% methanol as flowing
Phase, Zorbax SB-C18It is stationary phase that (21.2 × 250mm, 5 μm), which prepares post, flow rate of mobile phase 20ml/min, ultraviolet detection
Device Detection wavelength is 315nm, each μ L of sample introduction 200, is collected corresponding when chromatographic peak retention time after each sample introduction is 26.8min
Eluent, it is repeatedly cumulative after desolvation；Products therefrom is dissolved with pure methanol again, then using pure methanol as mobile phase, is used
Sephadex LH-20 gel filtration chromatographies separate, and produce the lactone compound further purified.
Wherein, during gradient elution, during the elution of the mixed solvent of each ratio, it is eluted to untill no composition 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% ethanol extracts 4 times, extracts 48h every time, and extract solution merges, and filtering, be concentrated under reduced pressure to obtain tobacco extract medicinal extract 245g.Will
The above-mentioned tobacco extract medicinal extract thick silica gel mixed sample of 80 mesh that 250g is used after the dissolving of the pure methanol of its 2.0 times of weight, then with 1.2kg
200 mesh silica gel mixing after fill post 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
Chloroform-acetone elution fraction pacifies the prompt preparative high-performance liquid chromatographic of logical sequence 1,100 half separation, using 54wt% methanol as mobile phase,
Zorbax SB-C18It is stationary phase that (21.2 × 250mm, 5 μm), which prepares post, flow rate of mobile phase 20ml/min, UV-detector inspection
Survey wavelength is 315nm, each μ L of sample introduction 200, collects corresponding when chromatographic peak retention time after each sample introduction is 26.8min wash
De- liquid, desolvation 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 separate, and produce the lactone compound further purified.
Wherein, during gradient elution, during the elution of the mixed solvent of each ratio, it is eluted to untill no composition 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, 72h is extracted every time, extract solution merges, and filtering, be concentrated under reduced pressure to obtain tobacco extract medicinal extract
385g.By the above-mentioned tobacco extract medicinal extract thick silica gel mixed sample of 90 mesh that 400g is used after the pure methanol dissolving of its 1.6 times of weight, then
Post is filled after being mixed with 2.4kg 180 mesh silica gel 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
For 8:2 chloroform-acetone elution fraction pacifies the prompt preparative high-performance liquid chromatographic of logical sequence 1,100 half separation, using 54% methanol as flowing
Phase, Zorbax SB-C18It is stationary phase that (21.2 × 250mm, 5 μm), which prepares post, flow velocity 20ml/min, UV-detector detection
Wavelength is 315nm, each μ L of sample introduction 200, collects elution corresponding when chromatographic peak retention time after each sample introduction is 26.8min
Liquid, desolvation after repeatedly adding up；Products therefrom is dissolved with pure methanol again, then using pure methanol as mobile phase, uses Sephadex
LH-20 gel filtration chromatographies separate, and produce the lactone compound further purified.
Wherein, during gradient elution, during the elution of the mixed solvent of each ratio, it is eluted to untill no composition washes down, then
Change the mixed solvent of next ratio.
The identification of embodiment 5- compound structures
Compound prepared by Example 1, the structure of the lactone compound that method described above is prepared pass through following
Method is measured.The compounds of this invention is light yellow gum thing, high resolution mass spectrum HR-ESI-MS m/z:241.0848[M+
Na]+(calculated value 241.0841, C13H14NaO3), with reference to1H and13C H NMR spectroscopies determine that molecular formula is C13H14O3, degree of unsaturation 6.
Ultraviolet spectra has absorption maximum 210,278,315, illustrates aromatic ring structure in compound be present.IR shows molecular structure of compounds
In have carbonyl (1725cm-1) and aromatic ring (1610,1562 and 1458cm-1).Compound1H and13C H NMR spectroscopies (table -1) show it
Containing 13 carbon and 14 hydrogen, including 11,2,3,4- quaternary phenyl ring (C-4~C-7, C-4a, and C-7a；H-6and
H-7), 1 humorous dimethyl dihydro chromene ring (C-8~C-12；H2-8,H2-9,and H6- 11,12), an ester carbonyl group (δC
168.8s) and one oxidation methylene (δC72.7t δH5.45s).Its HMBC coherent signal is further analyzed, according to H2-3
With C-1, C-4, C-4a, C-7a, it is benzofuran lactone structure that H-7 and C-1, C-4a, C-7a (figure -3), which can speculate compound,.Change
H can be observed in the HMBC spectrums of compound2- 8 and C-4, C-5, C-4a；H2- 9 is long-range related to C-4's, can speculate humorous dimethyl two
Hydrogen chromene ring is substituted in C-4 the and C-5 positions of compound, and C-8 positions carbon is connected to the C-4 positions of phenyl ring.So far, the knot of compound
Structure is determined that the Compound nomenclature is：8,9- dihydros -7,7- methyl isophthalic acid H furans [3,4-f] chromene -3 (7H) -one.
Embodiment 6-8
The compound that respectively prepared by Example 2-4, is light yellow gum thing.Assay method is same as Example 5, confirms
Compound prepared by embodiment 2-4 is lactone compound 8,9- dihydros -7,7- methyl isophthalic acid H furans [3,4-f] chromene -3
(7H) -one.
Embodiment 9- perfumings are tested
The lactone compound of any preparation in Example 1-4 carries out the perfuming effect experiment of cigarette, and test situation is such as
Under：
It is Hong Yun Red River group product " purple cloud and mist " Cigarette for addition cigarette, the pipe tobacco weight of every is 0.68g.
To be not added with " purple cloud and mist " Cigarette of any other material as blank control.Above-mentioned lactone compound ethanol is water-soluble
Liquid is made into 0.68% (m/v) solution, is added respectively with 5 μ L, 10 μ L, 15 μ L, 20 μ L, tetra- injection volume essence and flavoring agent injectors
Add 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 A1, B1, C1 and D1, smoked panel test for expert sensory.
The Cigarette and blank control cigarette that the lactone compound of the present invention will be with the addition of carry out organoleptic quality evaluations,
As a result show, lactone compound of the invention is used for cigarette flavouring upgrading positive effect, can be obviously improved cigarette flavor concentration,
Increase perfume quantity, improve cigarette sense organ suction quality, had broad application prospects as cigarette additive.
Embodiment 10- and humectant synergy
The lactone compound of any preparation enters them with humectant and cigarette sensory quality is cooperateed with Example 1-4
Effect test, test situation are as follows：
It is Hong Yun Red River group product " purple cloud and mist " Cigarette for addition cigarette, the pipe tobacco weight of every is 0.68g.
To be not added with " purple cloud and mist " Cigarette of any other material as blank control.Above-mentioned lactone compound is matched somebody with somebody with humectant
Into 0.68% (m/v) solution, it is added to respectively with 5 μ L, 10 μ L, 15 μ L, 20 μ L, tetra- injection volumes with essence and flavoring agent injector
In different " purple cloud and mist " Cigarette pipe tobaccos, then by cigarette sample in (22 ± 1) DEG C, the condition of relative humidity 60% ± 2%
Lower balance 48h, respectively obtains Cigarette A2, B2, C2 and D2.Above-mentioned lactone compound is made into 0.68% with humectant
(m/v) solution, different " purples is added to essence and flavoring agent injector with 5 μ L, 10 μ L, 15 μ L, 20 μ L, tetra- injection volumes respectively
In cloud and mist " Cigarette pipe tobacco, then be separately added into the pipe tobacco of above-mentioned kinds of cigarettes cigarette account for tobacco quality 0.1%,
0.4%th, 0.7%, 1% humectant.Wherein described humectant can be any of glycerine, propane diols or sorbierite or it
Mixture.Then cigarette sample is balanced into 48h under the conditions of (22 ± 1) DEG C, relative humidity 60% ± 2%.Respectively obtain
Cigarette A3, B3, C3 and D3.
By the Cigarette for the lactone compound that with the addition of the present invention respectively while it with the addition of lactone of the invention
The Cigarette and blank control cigarette of compound and humectant carry out organoleptic quality evaluations, and smoking result shows：In cigarette
The compound and humectant are added, there is good physics and sense organ humectation to act on to cigarette, can soft cigarette smoke, raising
The mellow and full sense of flue gas and comfortableness, also there is the effect for assigning the cigarette smoke fragrance of a flower.It can be seen that have between the compound and humectant
There is synergy.For lactone compound relative to the optimum addition of pipe tobacco between 0.05 ‰~0.15 ‰, humectant is relative
In pipe tobacco optimum addition between 0.1%~0.7%.The compounds of this invention is simple in construction, can be obviously improved cigarette smoking
Quality, can be as the guiding compound of tobacco aromaticss research and development and with humectant with the use of the new of improvement cigarette smoking quality
It is prepared by additive.
Claims (6)
1. a kind of lactone compound, it is characterised in that it has following structural formula：
The compound is named as：8,9- dihydro -7,7- methyl isophthalic acid H furans [3,4-f] chromene -3 (7H) -one, English are entitled：8,
9-dihydro-7,7-dimethyl-1H-furo[3,4-f]chromen-3(7H)-one；Molecular formula is C13H14O3。
2. a kind of preparation method of lactone compound according to claim 1, it is characterised in that the preparation method includes
Following steps：
(1) tobacco extract medicinal extract is prepared:Using airing tobacco as raw material, airing tobacco is crushed or is cut into segment, and with first
Solvent soaking simultaneously extracts the tobacco leaf 3~5 times, each 24h~72h, and extract solution is merged, filtered and the cigarette is obtained after concentrating
Careless extract medicinal extract；Wherein described first solvent is the mixture selected from methanol, the organic solvent of ethanol or acetone and water, works as institute
When to state the first solvent be methanol or the mixture of ethanol and water, wherein methanol or ethanol 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
Post 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, it is 8 to collect wherein with volume ratio:The eluent obtained during 2 chloroform-acetone solution elution, referred to as the first eluent；
(3) high pressure liquid chromatography isolates and purifies：The first above-mentioned eluent is passed through into high pressure liquid chromatography to be isolated and purified, should
High pressure liquid chromatography uses 21.2mm × 250mm, 5 μm of C18Chromatographic column, flow rate of mobile phase 20mL/min, mobile phase are
54wt% methanol, UV-detector Detection wavelength are 315nm, each μ L of sample introduction 200 of the first eluent, chromatogram after each sample introduction
Peak retention time eluent corresponding when being 26.8min, referred to as the second eluent, will be after the second eluent desolvation
Obtain the lactone compound.
3. preparation method according to claim 2, it is characterised in that：The step of it also includes purifying further below：Will
Pure methanol is again dissolved in the lactone compound that high pressure liquid chromatography separation obtains afterwards, and using pure methanol as stream
Dynamic phase, chromatography, the lactone compound further purified are carried out by gel column.
4. preparation method according to claim 2, it is characterised in that：In step (2), with 160~300 mesh silica gel
Before mixing, first by the tobacco extract medicinal extract with its 1.5~3 times of weight selected from pure methanol, straight alcohol or pure acetone
80~100 mesh silica gel mixed samples after the dissolving of second solvent with 0.8~1.2 times of weight for tobacco extract medicinal extract.
5. lactone compound according to claim 1 is used for the purposes for improving cigarette smoking quality.
6. lactone compound according to claim 1 is used for soft cigarette smoke, combined with humectant for increasing cigarette
The purposes of the gas fragrance of a flower.
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| CN201610743725.9A CN106380473B (en) | 2016-08-29 | 2016-08-29 | A kind of lactone compound, preparation method and use |
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| CN201610743725.9A CN106380473B (en) | 2016-08-29 | 2016-08-29 | A kind of lactone compound, preparation method and use |
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| CN106380473A CN106380473A (en) | 2017-02-08 |
| CN106380473B true CN106380473B (en) | 2018-01-12 |
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| CN106957322B (en) * | 2017-04-01 | 2018-07-20 | 云南中烟工业有限责任公司 | A kind of isobenzofuran class compound and the preparation method and application thereof that can improve cigarette smoking throat comfort |
| CN106883245B (en) * | 2017-04-01 | 2018-07-24 | 云南中烟工业有限责任公司 | It is a kind of that there is the benzisoxa furfuran compound and the preparation method and application thereof for removing free radical effect |
| CN106858710B (en) * | 2017-04-01 | 2018-03-09 | 云南中烟工业有限责任公司 | A kind of benzisoxa furfuran compound that can improve cigarette smoking effect and preparation method and application |
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