CN105481818A - Aroma-enhancing moisture-retaining isocoumarin compound, and preparation method and application thereof - Google Patents
Aroma-enhancing moisture-retaining isocoumarin compound, and preparation method and application thereof Download PDFInfo
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- CN105481818A CN105481818A CN201510810018.2A CN201510810018A CN105481818A CN 105481818 A CN105481818 A CN 105481818A CN 201510810018 A CN201510810018 A CN 201510810018A CN 105481818 A CN105481818 A CN 105481818A
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- C07—ORGANIC CHEMISTRY
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- 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 an isocoumarin compound, which is named as 5-((E)-4-hydroxy-3-methyl-butyl-3-ene)-3-(hydroxymethyl)-1H-isochromen-6-ol and has a molecular formula of C15H18O4. The structure of the isocoumarin compound is described in the specification. The invention also discloses a preparation method and application of the isocoumarin compound. Experiments prove that the isocoumarin compound provided by the invention is capable of improving the smoking quality of cigarettes; and through mixing of the isocoumarin compound with a moisture-retaining agent according to a proper ratio, good physical and sensory moisture-retaining effects are exerted on cigarettes, the smoke of cigarettes can be softened, the mellow and full sensation and amenity of the smoke of cigarettes can be improved, and the smoke of cigarettes is endowed with delicate fragrance.
Description
Technical field
The invention belongs to technical field of tobacco chemistry, be specifically related to a kind ofly from airing cigarette, extract the Isocoumarin compounds obtained first.Meanwhile, the invention still further relates to the preparation method of this Isocoumarin compounds and improving the purposes in cigarette smoking quality with humectant combined utilization.
Background technology
Tobacco is the plant that chemical composition is the most complicated in the world, and secondary metabolite is very abundant, and through the research of decades, the monomer chemistries material that people identify out at present from tobacco just more than kind more than 3000, and also has many compositions not yet to identify out.Extensively approved although Smoking is harmful to your health, tobacco still has powerful magnetism to thousands of human consumer, except Nicotine additive except, fragrance matter abundant in tobacco also plays an important role.
Isocoumarin is the basic structure of some natural products, is distributed widely in occurring in nature, of a great variety.People once synthesized this compounds by multiple method.The derivative of this compounds is except having antibacterial, anti-inflammatory, anticancer, the physiology such as protease inhibition and weeding and biological activity, and some compounds also have outstanding fragrance characteristic, are important flavor compounds.In order to the structure activity relationship studying this compounds finds compound with practical value, people have also carried out a large amount of bioactivity research to this compounds.The present invention is separated to obtain from airing cigarette a kind ofly has the Isocoumarin compounds improving cigarette smoking quality function, and this compound it is not yet seen relevant report.
Mainly adopt the polyhydroxy substances such as glycerine, propylene glycol, sorbyl alcohol as humectant in China's cigarette industry, the main purpose of humectant is the water ratio maintaining pipe tobacco in the course of processing, improve the resist processing of pipe tobacco, but above-mentioned humectant is sucked in comfort level at finished cigarettes and is had very large associating with its formulation composition and blending thereof.The present invention a kind ofly has the Isocoumarin compounds improving cigarette smoking quality function by being separated to obtain, and this compound coordinates the suction quality improving cigarette also to have no relevant report with humectant.
Summary of the invention
The object of the present invention is to provide a kind of new Isocoumarin compounds.
Another object of the present invention is to provide a kind of method preparing described Isocoumarin compounds.
The present invention also aims to provide described Isocoumarin compounds improving the purposes in cigarette smoking quality.
Except as otherwise noted, the percentage ratio adopted in the present invention is weight percentage.
First aspect present invention relates to isolated a kind of new Isocoumarin compounds from airing cigarette, and it has following structural formula:
The called after of this compound: 5-((E)-4-hydroxy-3-methyl-butyl-2-alkene) the heterochromatic alkene of-3-(methylol)-1H--6-alcohol, English by name: [5-((E)-4-hydroxy-3-methylbut-2-enyl)-3-(hydroxymethyl)-1H-isochromen-6-ol], molecular formula is C
15h
18o
4, be light yellow gum thing.
Second aspect present invention relates to a kind of preparation method of Isocoumarin compounds described according to a first aspect of the present invention, and this preparation method comprises the following steps:
(1) tobacco extract medicinal extract is prepared: with airing cigarette tobacco leaf for raw material, tobacco leaf is pulverized or is cut into segment, and extract described tobacco leaf 3 ~ 5 times, each 24h ~ 72h with the first solvent soaking, extracting solution is merged, filters and obtain described tobacco extract medicinal extract after concentrating; Wherein said first solvent is selected from the organic solvent of methyl alcohol, ethanol or acetone and the mixture of water, when described first solvent is the mixture of methyl alcohol or ethanol and water, wherein methyl alcohol or ethanol account for the 80wt% ~ 100wt% of this first solvent, when described first solvent is the mixture of acetone and water, wherein acetone accounts for the 60wt% ~ 90wt% of this first solvent; And the first solvent: tobacco=(2-4): (4-6), weight ratio;
(2) silica gel column chromatography: dry column-packing after above-mentioned tobacco extract medicinal extract is mixed with 160 ~ 300 order silica gel of its 2-4 times of weight, then carry out gradient elution by the chloroform-acetone solution that volume ratio is followed successively by 1:0,20:1,9:1,8:2,7:3,6:4,1:1 and 1:2, the elutriant obtained when wherein volume ratio is the chloroform-acetone solution wash-out of 8:2 is called the first elutriant;
(3) high pressure liquid chromatography separation and purification: above-mentioned first elutriant is passed into high pressure liquid chromatography and carries out separation and purification, this high pressure liquid chromatography adopts 21.2mm × 250mm, the C of 5 μm
18chromatographic column, flow rate of mobile phase is 20mL/min, moving phase is the methyl alcohol of 55%, UV-detector determined wavelength is 315nm, first elutriant each sample introduction 200 μ L, elutriant corresponding when chromatographic peak retention time is 28.2min after each sample introduction, is called the second elutriant, namely obtains described Isocoumarin compounds by after this second elutriant desolvation.
In a preferred embodiment of the present invention, it also comprises the step of following further purification: the described Isocoumarin compounds obtained after described high pressure liquid chromatography separation is dissolved in pure methyl alcohol again, and with pure methyl alcohol for moving phase, carry out chromatographic separation by gel column, obtain the Isocoumarin compounds of purifying further.
In a preferred embodiment of the present invention, in step (2), before mixing with described 160 ~ 300 order silica gel, first by 80 ~ 100 order silica gel mixed samples that are selected from second dissolution with solvents of pure methyl alcohol, straight alcohol or pure acetone after with 0.8 ~ 1.2 times of weight for tobacco extract medicinal extract of described tobacco extract medicinal extract by its 1.5 ~ 3 times of weight.
Third aspect present invention relates to Isocoumarin compounds described according to a first aspect of the present invention and is improving the purposes in cigarette smoking quality.
Fourth aspect present invention relate to according to a first aspect of the present invention described Isocoumarin compounds for soft cigarette smoke, act synergistically with humectant the purposes improving the mellow and full sense of cigarette smoke and comfortableness or give cigarette smoke delicate fragrance.
Compared with prior art, the present invention has following beneficial effect: Isocoumarin compounds of the present invention is separated first, novel structure.Add experiment through cigarette to show, compound of the present invention, to cigarette flavouring upgrading successful, significantly can promote cigarette flavor concentration, increases perfume quantity, improve cigarette sense organ suction quality, have broad application prospects as cigaret additive.Compound of the present invention and humectant are with suitable proportion proportioning, there is the purposes improving cigarette smoking quality, to cigarette, there is good physics and sense organ humectation effect, and can soft cigarette smoke, improve the mellow and full sense of cigarette smoke and comfortableness and there is the effect of giving cigarette smoke delicate fragrance.The compounds of this invention structure is simple, obviously can improve cigarette smoking quality, can be used as the guiding compound of tobacco aromatics using research and development and prepares with the use of the new additive improving cigarette smoking quality with humectant.
Accompanying drawing explanation
Fig. 1 is the carbon-13 nmr spectra of Isocoumarin compounds of the present invention;
Fig. 2 is the proton nmr spectra of Isocoumarin compounds of the present invention;
Fig. 3 is the main HMBC relevant indicators of Isocoumarin compounds of the present invention.
Embodiment
The structure of the Isocoumarin compounds prepared by the present invention measures out by the following method.The compounds of this invention is light yellow gum thing; UV spectrum (solvent is methyl alcohol), λ
max(log ε) 210 (3.65), 270 (3.36), 292 (3.14), 315 (3.27) nm; Infrared spectra (pressing potassium bromide troche) ν
max3422,3068,2963,2856,1612,1573,1463,1354,1165,1054cm
-1; High resolution mass spectrum (HRESIMS) provides quasi-molecular ion peak m/z285.1109 [M+Na]
+(calculated value 285.1103).In conjunction with
1h and
13cNMR spectrum provides a molecular formula C
15h
18o
4, degree of unsaturation is 7.Spectral data and the known compound versicololB of this compound are closely similar, difference be two methyl in known compound versicololB and methoxyl group respectively by the oxidation methylene radical of two in the compounds of this invention and a hydroxyl replace.These suppositions are confirmed further by HMBC is relevant.In HMBC spectrum, we observed H
2-9 relevant to C-3 and C-4, H
2relevant and Ar-OH and C-6, C-7 and the C-5's of-4' and C-2', C-3' and C-5' is relevant, thus proves that three hydroxyls are connected to the C-9 of compound, on C-4' and C-6.Meanwhile, H can also be observed in ROESY spectrum
2-4' is relevant to H-2''s, thus proves that isopentene group is E.So far the structure of this compound is determined.
Table 1. compound
1hNMR and
13cNMR data (CCl
3)
The compounds of this invention is separated first, is defined as Isocoumarin compounds by above-mentioned nucleus magnetic resonance and measuring method of mass spectrum, and characterizes its concrete structure.Add experiment through cigarette to show: this compound has the purposes improving cigarette smoking quality, and can with humectant conbined usage, can soft cigarette smoke, improve the mellow and full sense of flue gas and comfortableness, also there is the effect of giving cigarette smoke delicate fragrance.The compounds of this invention structure is simple, obviously can improve cigarette smoking quality, can be used as the guiding compound of tobacco aromatics using research and development and prepares with the new additive that humectant conbined usage improves cigarette smoking quality.
Below in conjunction with drawings and Examples, the present invention is described in further detail, but limited the present invention never in any form, and any conversion done based on training centre of the present invention or improvement, all fall into 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 all can realize the present invention, and to derive from the tobacco material of cigarette industry limited liability company Different sources in Yunnan, the present invention will be further described below.Except as otherwise noted, the percentage ratio adopted in the present invention is weight percentage.Unreceipted concrete technology or condition person in embodiment, according to the technology described by the document in this area or condition or carry out according to product description.Agents useful for same or the unreceipted production firm person of instrument, being can by buying the conventional products obtained.If the solution in the present invention only gives solute, do not disclose solvent, then those skilled in the art should know solvent is water.In the present invention, pure methyl alcohol refers to 100% methyl alcohol, and straight alcohol refers to 100% ethanol, and pure acetone refers to 100% acetone.
Embodiment 1
A kind of Isocoumarin compounds C
15h
18o
4preparation method, specifically comprise the following steps:
(1) prepare tobacco extract medicinal extract: take airing tobacco as raw material, tobacco leaf is pulverized or is cut into segment, and extract described tobacco leaf 4 times, each 54h with the first solvent soaking, by extracting solution merging, filter and obtain described tobacco extract medicinal extract after concentrating; Wherein said first solvent is selected from the organic solvent of methyl alcohol, ethanol or acetone and the mixture of water, when described first solvent is the mixture of methyl alcohol or ethanol and water, wherein methyl alcohol or ethanol account for the 95wt% of this first solvent, when described first solvent is the mixture of acetone and water, wherein acetone accounts for the 70wt% of this first solvent; And the first solvent: tobacco=3:5, weight ratio;
(2) silica gel column chromatography: by 80 ~ 100 order silica gel mixed samples that are selected from second dissolution with solvents of pure methyl alcohol, straight alcohol or pure acetone after with 1.2 times of weight for tobacco extract medicinal extract of described tobacco extract medicinal extract by its 2.5 times of weight, dry column-packing after mixing with 250 order silica gel of tobacco extract medicinal extract 3 times of weight again, then carry out gradient elution by the chloroform-acetone solution that volume ratio is followed successively by 1:0,20:1,9:1,8:2,7:3,6:4,1:1 and 1:2, the elutriant obtained when wherein volume ratio is the chloroform-acetone solution wash-out of 8:2 is called the first elutriant;
(3) high pressure liquid chromatography separation and purification: above-mentioned first elutriant is passed into high pressure liquid chromatography and carries out separation and purification, this high pressure liquid chromatography adopts 21.2mm × 250mm, the C of 5 μm
18chromatographic column, flow rate of mobile phase is 20mL/min, moving phase is the methyl alcohol of 55%, UV-detector determined wavelength is 315nm, first elutriant each sample introduction 200 μ L, elutriant corresponding when chromatographic peak retention time is 28.2min after each sample introduction, is called the second elutriant, namely obtains described Isocoumarin compounds by after this second elutriant desolvation.
Described preparation method also comprises the step of following further purification: the described Isocoumarin compounds obtained after described high pressure liquid chromatography separation is dissolved in pure methyl alcohol again, and with pure methyl alcohol for moving phase, carry out chromatographic separation by gel column, obtain the Isocoumarin compounds of purifying further.
Embodiment 2
Airing cigarette sample source used is in Yunnan Yuxi, and kind is Yuxi river and mountain cigarette.Tobacco leaf is sampled 2.0kg and pulverize methanol extraction 5 times with 95%, extract 24h, extracting solution merges at every turn, and filter, concentrating under reduced pressure obtains tobacco extract medicinal extract 95g.By the 100 order thick silica gel mixed sample of above-mentioned tobacco extract medicinal extract with 120g after the pure dissolve with methanol of its 2.0 weight multiple, fill post after mixing with the 160 order silica gel of 0.6kg again and carry out silica gel column chromatography, be 1:0 with volume proportion, 20:1, 9:1, 8:2, 7:3, 6:4, 1:1, chloroform-acetone the gradient elution of 1:2, TLC monitoring merges identical part, obtain 8 parts, wherein volume proportion is the prompt logical sequence 1,100 half preparative high-performance liquid chromatographic separation of chloroform-acetone elution fraction peace of 8:2, methyl alcohol with 55% is moving phase, ZorbaxSB-C18 (21.2 × 250mm, 5 μm) preparative column is stationary phase, flow rate of mobile phase is 20ml/min, UV-detector determined wavelength is 315nm, each sample introduction 200 μ L, elutriant corresponding when to collect chromatographic peak retention time after each sample introduction be 28.2min, repeatedly cumulative rear desolvation, products therefrom uses pure dissolve with methanol again, then with pure methyl alcohol for moving phase, is separated, obtains the Isocoumarin compounds of purifying further with SephadexLH-20 gel filtration chromatography.
Wherein, during gradient elution, during the mixed solvent wash-out of each ratio, be eluted to till not having composition to wash down, then change the mixed solvent of next ratio.
Embodiment 3
Airing cigarette sample source used is in Dali, and kind is that cigarette is stepped in sky, Yunlong.Tobacco leaf is sampled 3.5kg chopping, the extraction using alcohol with 95% 4 times, extracts 48h at every turn, and extracting solution merges, and filter, concentrating under reduced pressure obtains tobacco extract medicinal extract 245g.By the 80 order thick silica gel mixed sample of above-mentioned tobacco extract medicinal extract with 250g after the pure dissolve with methanol of its 2.0 times of weight, fill post after mixing with the 200 order silica gel of 1.2kg again and carry out silica gel column chromatography, be 1:0 with volume proportion, 20:1, 9:1, 8:2, 7:3, 6:4, 1:1, chloroform-acetone the gradient elution of 1:2, TLC monitoring merges identical part, obtain 8 parts, wherein volume proportion is the prompt logical sequence 1,100 half preparative high-performance liquid chromatographic separation of chloroform-acetone elution fraction peace of 8:2, methyl alcohol with 55% is moving phase, ZorbaxSB-C18 (21.2 × 250mm, 5 μm) preparative column is stationary phase, flow rate of mobile phase is 20ml/min, UV-detector determined wavelength is 315nm, each sample introduction 200 μ L, elutriant corresponding when to collect chromatographic peak retention time after each sample introduction be 28.2min, repeatedly cumulative rear desolvation, products therefrom uses pure dissolve with methanol again, then with pure methyl alcohol for moving phase, is separated, obtains the Isocoumarin compounds of purifying further with SephadexLH-20 gel filtration chromatography.
Wherein, during gradient elution, during the mixed solvent wash-out of each ratio, be eluted to till not having composition to wash down, then change the mixed solvent of next ratio.
Embodiment 4
Airing cigarette sample source used is in Kunming, Yunnan, and kind is Songming safflower cigarette.Tobacco leaf is sampled 5kg to pulverize, the supersound extraction 3 times of the acetone with 75%, extracts 72h at every turn, and extracting solution merges, and filter, concentrating under reduced pressure obtains tobacco extract medicinal extract 385g.By the 90 order thick silica gel mixed sample of above-mentioned tobacco extract medicinal extract with 400g after the pure dissolve with methanol of its 1.6 times of weight, fill post after mixing with the 180 order silica gel of 2.4kg again and carry out silica gel column chromatography, be 1:0 with volume proportion, 20:1, 9:1, 8:2, 7:3, 6:4, 1:1, chloroform-acetone the gradient elution of 1:2, TLC monitoring merges identical part, obtain 8 parts, wherein volume proportion is the prompt logical sequence 1,100 half preparative high-performance liquid chromatographic separation of chloroform-acetone elution fraction peace of 8:2, methyl alcohol with 55% is moving phase, ZorbaxSB-C18 (21.2 × 250mm, 5 μm) preparative column is stationary phase, flow velocity is 20ml/min, UV-detector determined wavelength is 315nm, each sample introduction 200 μ L, elutriant corresponding when to collect chromatographic peak retention time after each sample introduction be 28.2min, repeatedly cumulative rear desolvation, products therefrom uses pure dissolve with methanol again, then with pure methyl alcohol for moving phase, is separated, obtains the Isocoumarin compounds of purifying further with SephadexLH-20 gel filtration chromatography.
Wherein, during gradient elution, during the mixed solvent wash-out of each ratio, be eluted to till not having composition to wash down, then change the mixed solvent of next ratio.
The qualification of embodiment 5-compound structure
Compound prepared by Example 1, the structure of the Isocoumarin compounds prepared with aforesaid method measures by the following method.The compounds of this invention is light yellow gum thing; UV spectrum (solvent is methyl alcohol), λ
max(log ε) 210 (3.65), 270 (3.36), 292 (3.14), 315 (3.27) nm; Infrared spectra (pressing potassium bromide troche) ν
max3422,3068,2963,2856,1612,1573,1463,1354,1165,1054cm
-1; High resolution mass spectrum (HRESIMS) provides quasi-molecular ion peak m/z285.1109 [M+Na]
+(calculated value 285.1103).In conjunction with
1h and
13cNMR spectrum provides a molecular formula C
15h
18o
4, degree of unsaturation is 7.Spectral data and the known compound versicololB of this compound are closely similar, difference be two methyl in known compound versicololB and methoxyl group respectively by the oxidation methylene radical of two in the compounds of this invention and a hydroxyl replace.These suppositions are confirmed further by HMBC is relevant.In HMBC spectrum, we observed H
2-9 relevant to C-3 and C-4, H
2relevant and Ar-OH and C-6, C-7 and the C-5's of-4' and C-2', C-3' and C-5' is relevant, thus proves that three hydroxyls are connected to the C-9 of compound, on C-4' and C-6.Meanwhile, H can also be observed in ROESY spectrum
2-4' is relevant to H-2''s, thus proves that isopentene group is E.So far the structure of this compound is determined.
Embodiment 6-8
The compound prepared of Example 2-4, is light yellow gum thing respectively.Measuring method is identical with embodiment 5, confirms that compound prepared by embodiment 2-4 is Isocoumarin compounds 5-((E)-4-hydroxy-3-methyl-butyl-2-alkene) the heterochromatic alkene of-3-(methylol)-1H--6-alcohol.
Embodiment 9-Load unload response ratio
The Isocoumarin compounds of arbitrary preparation in Example 1-4 carries out the perfuming effect test of cigarette, and test situation is as follows:
Be Hong Yun Red River group product " purple cloud and mist " Cigarette for interpolation cigarette, the pipe tobacco weight of often propping up is 0.68g.Not add " purple cloud and mist " Cigarette of any other material for blank.Above-mentioned Isocoumarin compounds aqueous ethanolic solution is made into the solution of 0.68% (m/v), be added in different " purple cloud and mist " Cigarette pipe tobaccos with 5 μ L, 10 μ L, 15 μ L, 20 μ L, tetra-injection volume essence and flavoring agent injector respectively, then cigarette sample is balanced 48h under (22 ± 1) DEG C, relative humidity 60% ± 2% condition, obtain Cigarette A1, B1, C1 and D1 respectively, smoke panel test for expert sensory.
The Cigarette and blank cigarette that with the addition of Isocoumarin compounds of the present invention are carried out organoleptic quality evaluations, result shows, Isocoumarin compounds of the present invention is used for cigarette flavouring upgrading successful, significantly can promote cigarette flavor concentration, increase perfume quantity, improve cigarette sense organ suction quality, have broad application prospects as cigaret additive.
The synergy of embodiment 10-and humectant
The Isocoumarin compounds of arbitrary preparation in Example 1-4 and humectant carry out them to be tested the synergy of cigarette sensory quality, and test situation is as follows:
Be Hong Yun Red River group product " purple cloud and mist " Cigarette for interpolation cigarette, the pipe tobacco weight of often propping up is 0.68g.Not add " purple cloud and mist " Cigarette of any other material for blank.Above-mentioned Isocoumarin compounds humectant is made into the solution of 0.68% (m/v), be added in different " purple cloud and mist " Cigarette pipe tobaccos with 5 μ L, 10 μ L, 15 μ L, 20 μ L, tetra-injection volume essence and flavoring agent injector respectively, then cigarette sample is balanced 48h under (22 ± 1) DEG C, relative humidity 60% ± 2% condition, obtain Cigarette A2, B2, C2 and D2 respectively.Above-mentioned Isocoumarin compounds humectant is made into the solution of 0.68% (m/v), be added in different " purple cloud and mist " Cigarette pipe tobaccos with 5 μ L, 10 μ L, 15 μ L, 20 μ L, tetra-injection volume essence and flavoring agent injector, then add the humectant accounting for tobacco quality 0.1%, 0.4%, 0.7%, 1% respectively in the pipe tobacco of above-mentioned kinds of cigarettes cigarette respectively.Wherein said humectant can be the mixture of any one or they in glycerine, propylene glycol or sorbyl alcohol.Then cigarette sample is balanced 48h under (22 ± 1) DEG C, relative humidity 60% ± 2% condition.Obtain Cigarette A3, B3, C3 and D3 respectively.
Organoleptic quality evaluations is carried out by with the addition of the Cigarette of Isocoumarin compounds of the present invention, the Cigarette that with the addition of Isocoumarin compounds of the present invention and humectant and blank cigarette respectively simultaneously, smoking result shows: in cigarette, add Isocoumarin compounds of the present invention and humectant, to cigarette, there is good physics and sense organ humectation effect, can soft cigarette smoke, improve the mellow and full sense of flue gas and comfortableness, also there is the effect of giving cigarette smoke delicate fragrance.Visible have synergy between this compound and humectant.Isocoumarin compounds relative to the optimum addition of pipe tobacco between 0.05 ‰ ~ 0.15 ‰, humectant relative to the optimum addition of pipe tobacco between 0.1% ~ 0.7%.
The compounds of this invention structure is simple, obviously can improve cigarette smoking quality, can be used as the guiding compound of tobacco aromatics using research and development and prepares with the use of the new additive improving cigarette smoking quality with humectant.
Claims (6)
1. an Isocoumarin compounds, is characterized in that: it has following structural formula:
The called after of this compound: 5-((E)-4-hydroxy-3-methyl-butyl-2-alkene) the heterochromatic alkene of-3-(methylol)-1H--6-alcohol, molecular formula is C
15h
18o
4.
2. a preparation method for Isocoumarin compounds according to claim 1, is characterized in that: this preparation method comprises the following steps:
(1) tobacco extract medicinal extract is prepared: take airing tobacco as raw material, airing tobacco is pulverized or is cut into segment, and extract described tobacco leaf 3 ~ 5 times, each 24h ~ 72h with the first solvent soaking, extracting solution is merged, filters and obtain described tobacco extract medicinal extract after concentrating; Wherein said first solvent is selected from the organic solvent of methyl alcohol, ethanol or acetone and the mixture of water, when described first solvent is the mixture of methyl alcohol or ethanol and water, wherein methyl alcohol or ethanol account for the 80wt% ~ 100wt% of this first solvent, when described first solvent is the mixture of acetone and water, wherein acetone accounts for the 60wt% ~ 90wt% of this first solvent; And the first solvent: tobacco=(2-4): (4-6), weight ratio;
(2) silica gel column chromatography: dry column-packing after above-mentioned tobacco extract medicinal extract is mixed with 160 ~ 300 order silica gel of its 2-4 times of weight, then carry out gradient elution by the chloroform-acetone solution that volume ratio is followed successively by 1:0,20:1,9:1,8:2,7:3,6:4,1:1 and 1:2, the elutriant obtained when wherein volume ratio is the chloroform-acetone solution wash-out of 8:2 is called the first elutriant;
(3) high pressure liquid chromatography separation and purification: above-mentioned first elutriant is passed into high pressure liquid chromatography and carries out separation and purification, this high pressure liquid chromatography adopts 21.2mm × 250mm, the C of 5 μm
18chromatographic column, flow rate of mobile phase is 20mL/min, moving phase is the methyl alcohol of 55%, UV-detector determined wavelength is 315nm, first elutriant each sample introduction 200 μ L, elutriant corresponding when chromatographic peak retention time is 28.2min after each sample introduction, is called the second elutriant, namely obtains described Isocoumarin compounds by after this second elutriant desolvation.
3. preparation method according to claim 2, it is characterized in that: it also comprises the step of following further purification: the described Isocoumarin compounds obtained after described high pressure liquid chromatography separation is dissolved in pure methyl alcohol again, and with pure methyl alcohol for moving phase, carry out chromatographic separation by gel column, obtain the Isocoumarin compounds of purifying further.
4. preparation method according to claim 2, it is characterized in that: in step (2), before mixing with described 160 ~ 300 order silica gel, first by described tobacco extract medicinal extract with its 1.5 ~ 3 times of weight be selected from after the second dissolution with solvents of pure methyl alcohol, straight alcohol or pure acetone with 80 ~ 100 order silica gel mixed samples for tobacco extract medicinal extract 0.8 ~ 1.2 times of weight.
5. Isocoumarin compounds according to claim 1 is for improving the purposes of cigarette smoking quality.
6. Isocoumarin compounds according to claim 1 is used for soft cigarette smoke, act synergistically with humectant the purposes improving the mellow and full sense of cigarette smoke and comfortableness or give cigarette smoke delicate fragrance.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN105906566A (en) * | 2016-05-19 | 2016-08-31 | 云南中烟工业有限责任公司 | Alkaloid compound with antibacterial activity in tobaccos as well as preparation method and use of alkaloid compound |
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| 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 |
| CN111533720A (en) * | 2020-05-09 | 2020-08-14 | 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 |
| 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 |
| CN114805276A (en) * | 2022-03-14 | 2022-07-29 | 云南中烟工业有限责任公司 | Isochromene compound and preparation method and application thereof |
| CN114920723A (en) * | 2022-03-14 | 2022-08-19 | 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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