CN105017190A - Preparation method and use of benzolactone compound in tobacco - Google Patents
Preparation method and use of benzolactone compound in tobacco Download PDFInfo
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- CN105017190A CN105017190A CN201510357481.6A CN201510357481A CN105017190A CN 105017190 A CN105017190 A CN 105017190A CN 201510357481 A CN201510357481 A CN 201510357481A CN 105017190 A CN105017190 A CN 105017190A
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- medicinal extract
- acetone
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- lactone compound
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
- C07D307/88—Benzo [c] furans; Hydrogenated benzo [c] furans with one oxygen atom directly attached in position 1 or 3
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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
- A24B15/406—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 in a five-membered ring
-
- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
- A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
- A24B3/00—Preparing tobacco in the factory
- A24B3/12—Steaming, curing, or flavouring tobacco
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- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
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- General Chemical & Material Sciences (AREA)
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Abstract
The invention discloses one kind benzo lactone compound as shown in formula (I) and its preparation method and application,
, formula (I) belongs to technical field of tobacco chemistry. Using tobacco leaf as raw material,With high concentration methanol aqueous solution,High concentration ethanol aqueous solution or high concentration aqueous acetone solution are extracted as Extraction solvent,Extracting solution merges,Filtering,Medicinal extract is concentrated under reduced pressure into; Medicinal extract carries out silica gel column chromatography with silica gel dry column-packing; Gradient elution is carried out using chloroform-acetone mixed solvent as eluant, eluent,TLC monitoring merges identical part and is concentrated; The part that the chloroform-acetone mixed solvent elution collection for being 7:3 with volume proportion is concentrated to get further is isolated and purified with high pressure liquid chromatography up to required benzo lactone compound. Cigarette addition experiment shows: the soft cigarette smoke of compound energy, the exquisiteness for increasing flue gas, oral cavity moisture feeling have promotion.
Description
Technical field
The invention belongs to technical field of tobacco chemistry, be specifically related to a kind ofly from tobacco, extract the benzo lactone compound obtained first.Meanwhile, the invention still further relates to the preparation method of this compound and improving the application 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, 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.Along with the fast development of China's economy, the requirement of cigarette consumption person to product inner quality is more and more higher, extensively approved although Smoking is harmful to your health, but tobacco still has powerful magnetism to thousands of human consumer, except Nicotine additive except, fragrance matter abundant in tobacco also plays an important role.
Lactone refers to that carboxyl in same a part and hydroxyl interact and dewaters and the ester compound formed, this compounds ubiquity in natural phant, also the bibliographical information that there is this compounds is had in tobacco, except having pharmacological action widely, lactone or the important volatile compound of a class, can play the effect of flavouring humectation to tobacco.It is natural is present in various fruit and spice berry, and this compounds has now been widely used in the formula of the food flavours such as various beverage, bakery product.The present invention is separated to obtain from tobacco a kind ofly has the benzo lactone compound improving cigarette smoking quality function, and this compound it is not yet seen relevant report.
Summary of the invention
The object of the present invention is to provide a kind of new benzo lactone compound.
Another object of the present invention is to provide a kind of method preparing described benzo lactone compound.
The present invention also aims to provide described benzo lactone compound improving the application in cigarette smoking quality.
Except as otherwise noted, the percentage ratio adopted in the present invention is mass percent.
The present invention isolates a kind of new benzo lactone compound from tobacco, and its molecular formula is C
12h
12o
4, there is the structural formula as shown in formula I:
This Compound nomenclature is 6-(3-hydroxypropanoyl)-5-methyl isobenzofuran-1 (3H)-one; English name is: 6-(3-hydroxypropanoyl)-5-methylisobenzofuran-1 (3H)-one, is light yellow gum thing.
Prepare the method for above-mentioned benzo lactone compound, the method comprises the following steps:
Step (1), medicinal extract extracts: (the present invention is to the granularity not requirement after tobacco leaf pulverizing to pulverize tobacco sample or be cut into segment, the concrete length of the segment be cut into is not limited), with high concentration methanol (w%:80% ~ 100%) or high concentration ethanol (w%:80% ~ 100%) or high density acetone (w%:60% ~ 90%) for Extraction solvent carries out soak extraction, Extraction solvent: tobacco (weight ratio)=2 ~ 4:1, soak 24h ~ 72h, extract 3 ~ 5 times, united extraction liquid, filtering and concentrating becomes medicinal extract;
Step (2), silica gel column chromatography: the medicinal extract weight that step (1) obtains is after the pure methyl alcohol of its 1.5 ~ 3 times amount, straight alcohol or pure acetone dissolve, with 80 ~ 100 order silica gel mixed samples that weight is medicinal extract 0.8 ~ 1.2 times, simultaneously, with 160 ~ 300 order silica gel dry column-packings that weight is medicinal extract 2 ~ 4 times amount, then dry method loading, carries out silica gel column chromatography; The mixed solvent being followed successively by the chloroform-acetone of (1:0,20:1,9:1,8:2,7:3,6:4,1:1 and 1:2) using volume proportion carries out gradient elution as eluent, merges identical part, collects each several part elutriant and concentrates; 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; Step (3), high pressure liquid chromatography separation and purification: the mixed solvent wash-out of the chloroform-acetone with volume proportion being 7:3 is collected the concentrated part obtained and namely obtains described benzo lactone compound with high pressure liquid chromatography separation and purification further.
High pressure liquid chromatography separation and purification adopts column length × internal diameter to be 21.2mm × 250mm, and inner film thickness is the C of 5 μm
18chromatographic column, flow velocity is 20mL/min, moving phase to be mass concentration be 35% methanol aqueous solution, UV-detector determined wavelength is 312nm, each sample introduction 200 μ L, collects the chromatographic peak of 22.4min, evaporate to dryness after repeatedly cumulative.
After described high performance liquid chromatography separation and purification, a preferred subsequent process scheme is that gained compound uses pure dissolve with methanol again, then with pure methyl alcohol for moving phase, is separated with gel filtration chromatography, with further separation and purification.
The structure of the benzo lactone compound 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) 312 (3.22), 280 (3.57), 214 (4.05) nm; Infrared spectra (pressing potassium bromide troche) ν
max3442,2918,1735,1657,1610,1542,1476,1387,1259,1142,1064,869,768cm
-1; High resolution mass spectrum (HRESIMS) provides quasi-molecular ion peak m/z 219.0652 [M-H]
-(calculated value 219.0657).Shown in composition graphs 1 and Fig. 2
1h and
13c NMR spectrum provides a molecular formula C
12h
12o
4, degree of unsaturation is 7.From
1h and
13cNMR composes (attribution data is in table 1) signal can find out in compound have 1,2,4, a 5-quaternary phenyl ring, a 3-hydroxypropanoyl, an oxidation methylene radical, ester carbonyl group, a methyl.Lactone is constituted by Sauerstoffatom according to the HMBC of H-2' with C-3' relevant (Fig. 3) susceptible of proof C-2' and C-3'.-1 of phenyl ring is connected to, according to methyl hydrogen H-1' and C-1, C-2 susceptible of proof methyl substituted relevant with the HMBC of C-3 in C-2 position according to the HMBC of H-8 and C-1, H-6 and C-7 relevant susceptible of proof 3-hydroxypropanoyl.So far the structure of this compound is determined.
Table 1. compound
1h NMR and
13c NMR data (C
5d
5n)
This compound has been carried out the perfuming experiment of cigarette, be Hong Yun Red River group product " purple cloud and mist " for interpolation cigarette, often propping up pipe tobacco weight is 0.65g.Above-mentioned benzo lactone compound ethanol is made into 0.65% (m/v, g/mL) solution, add by essence and flavoring agent injector, divide 5 μ L, 10 μ L, 15 μ L, 20 μ L, tetra-injection volumes, the benzo lactone compound of injection accounts for 0.05 ‰, 0.1 ‰, 0.15 ‰, 0.2 ‰ of pipe tobacco total amount respectively, not add benzo lactone compound for contrast.After having injected, at room temperature open wide and put 2h, allow solvent evaporates.Then cigarette sample is balanced 48h under (22 ± 1) DEG C, relative humidity 60% ± 2% condition, smoke panel test for expert sensory.Smoking result shows: in cigarette, add this compound, can soft cigarette smoke, increase the exquisiteness of flue gas, oral cavity moisture feeling has lifting, fragrance is more clear, optimum addition is between 0.05 ‰ ~ 0.15 ‰.
Compared with prior art, the present invention has following beneficial effect:
The compounds of this invention is separated first, is determined as benzo lactone compound, and characterize its concrete structure by above-mentioned nucleus magnetic resonance and measuring method of mass spectrum.Add experiment through cigarette to show: this compound can soft cigarette smoke, increase the exquisiteness of flue gas, oral cavity moisture feeling has lifting, fragrance more clear.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 for improving the new additive preparation of cigarette smoking quality.
Accompanying drawing explanation
Fig. 1 is the carbon-13 nmr spectra of benzo lactone compound of the present invention;
Fig. 2 is the proton nmr spectra of benzo lactone compound of the present invention;
Fig. 3 is the main of benzo lactone compound of the present invention
1h-
1h COSY with HMBC is relevant.
Embodiment
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.
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
Prepare benzo lactone compound C
12h
12o
4, comprise medicinal extract extraction, silica gel column chromatography, high pressure liquid chromatography separation, specifically adopt following steps:
Step (1), medicinal extract extracts: get tobacco leaf and pulverize, be Extraction solvent with high concentration methanol (w%:90%) or high concentration ethanol (w%:95%) or high density acetone (w%:75%), Extraction solvent: tobacco (weight ratio)=3:1, soak 54h, extract 4 times, united extraction liquid, filtering and concentrating become medicinal extract.
Step (2), silica gel column chromatography: the medicinal extract weight that step (1) obtains is after the pure methyl alcohol of its 3 times amount, straight alcohol or pure acetone dissolve, with 80 ~ 100 order silica gel mixed samples that weight is medicinal extract 2.5 times, meanwhile, silica gel column chromatography is carried out with the 250 order silica gel dry column-packings that weight is medicinal extract 2.5 times amount; The mixed solvent being followed successively by the chloroform-acetone of (1:0,20:1,9:1,8:2,7:3,6:4,1:1 and 1:2) using volume proportion carries out gradient elution as eluent, and TLC monitoring merges identical part, collects each several part elutriant and concentrates.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;
Step (3), high pressure liquid chromatography is separated: the mixed solvent wash-out of the chloroform-acetone with volume proportion being 7:3 is collected the concentrated part obtained and namely obtains described benzo lactone compound with high pressure liquid chromatography separation and purification further, high pressure liquid chromatography separation and purification adopts 21.2mm × 250mm, the C of 5 μm
18chromatographic column, flow velocity is 20mL/min, and moving phase is the methyl alcohol of 35%, and UV-detector determined wavelength is 312nm, each sample introduction 200 μ L, collects the chromatographic peak of 22.4min, repeatedly cumulative rear evaporate to dryness.
Material after high pressure lipuid chromatography (HPLC) separation and purification, a preferred aftertreatment scheme is that gained compound uses pure dissolve with methanol again, then with pure methyl alcohol for moving phase, is separated with gel filtration chromatography, with further separation and purification.
The present invention's raw tobacco material used does not limit by area and kind, all can realize the present invention, and below to derive from the raw tobacco material of cigarette industry limited liability company Different sources in Yunnan, the present invention will be further described:
Embodiment 2
Tobacco sample derives from Yunnan Yuxi, and kind is Yuxi K326.Tobacco is sampled 2.0kg and pulverize methyl alcohol soak extraction 5 times with 95%, extract 24h, Extraction solvent: the weight ratio=2:1 of tobacco leaf, extracting solution merges at every turn, and filter, concentrating under reduced pressure becomes medicinal extract, obtains medicinal extract 105g.Medicinal extract weight is after the pure dissolve with methanol of its 2.0 times amount, with the thick silica gel mixed sample of 100 order of 120g, the 160 order silica gel dress posts of 0.6kg, carry out silica gel column chromatography, 1:0 is followed successively by 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 and concentrates, obtain 8 parts, wherein chloroform-acetone the wash-out with volume proportion being 7:3 is concentrated prompt logical sequence 1,100 half preparative high-performance liquid chromatographic of part peace obtained to be separated, methyl alcohol with 35% is moving phase, Zorbax SB-C18 (21.2 × 250mm, 5 μm) preparative column is stationary phase, flow velocity is 20ml/min, UV-detector determined wavelength is 312nm, each sample introduction 200 μ L, collect the chromatographic peak of 22.4min, repeatedly cumulative rear evaporate to dryness, products therefrom uses pure dissolve with methanol again, then with pure methyl alcohol for moving phase, is separated, obtains this new compound with Sephadex LH-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
Tobacco sample derives from Dali, and kind is cloud and mist 200, tobacco is sampled 3.5kg and is cut into segment, and the alcohol immersion with 95% extracts 4 times, each extraction 48h, Extraction solvent: the weight ratio=4:1 of tobacco leaf, extracting solution merges, filter, concentrating under reduced pressure becomes medicinal extract, obtains medicinal extract 250g.Medicinal extract weight is after the pure dissolve with methanol of its 2.0 times amount, with the thick silica gel mixed sample of 80 order of 250g, the 200 order silica gel dress posts of 1kg, carry out silica gel column chromatography, 1:0 is followed successively by with volume proportion, 20:1, 9:1, 8:27:3, 6:4, 1:1, chloroform-acetone the gradient elution of 1:2, TLC monitoring merges identical part and concentrates, obtain 8 parts, wherein chloroform-acetone the wash-out with volume proportion being 7:3 is concentrated prompt logical sequence 1,100 half preparative high-performance liquid chromatographic of part peace obtained to be separated, methyl alcohol with 35% is moving phase, Zorbax SB-C18 (21.2 × 250mm, 5 μm) preparative column is stationary phase, flow velocity is 20ml/min, UV-detector determined wavelength is 312nm, each sample introduction 200 μ L, collect the chromatographic peak of 22.4min, repeatedly cumulative rear evaporate to dryness, obtain this new compound.
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
Tobacco sample derives from Kunming, Yunnan, and kind is the large gold dollar of safflower, tobacco is sampled 5kg and pulverizes, the acetone soak extraction with 75% 3 times, each extraction 72h, Extraction solvent: the weight ratio=3:1 of tobacco leaf, extracting solution merges, filter, concentrating under reduced pressure becomes medicinal extract, obtains medicinal extract 380g.Medicinal extract weight is after the pure dissolve with methanol of its 1.6 times amount, with the thick silica gel mixed sample of 90 order of 400g, the 180 order silica gel dress posts of 1.5kg, carry out silica gel column chromatography, 1:0 is followed successively by 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 and concentrates, obtain 8 parts, wherein chloroform-acetone the wash-out with volume proportion being 7:3 is concentrated prompt logical sequence 1,100 half preparative high-performance liquid chromatographic of part peace obtained to be separated, methyl alcohol with 35% is moving phase, Zorbax SB-C18 (21.2 × 250mm, 5 μm) preparative column is stationary phase, flow velocity is 20ml/min, UV-detector determined wavelength is 312nm, each sample introduction 200 μ L, collect the chromatographic peak of 22.4min, repeatedly cumulative rear evaporate to dryness, products therefrom uses pure dissolve with methanol again, then with pure methyl alcohol for moving phase, is separated, obtains this new compound with Sephadex LH-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 5
Tobacco sample derives from Dali, and kind is cloud and mist 200, tobacco is sampled 3.5kg and is cut into segment, and the alcohol immersion with 80% extracts 3 times, each extraction 72h, Extraction solvent: the weight ratio=2:1 of tobacco leaf, extracting solution merges, filter, concentrating under reduced pressure becomes medicinal extract, obtains medicinal extract 250g.Medicinal extract weight is after the pure dissolve with methanol of its 1.5 times amount, with weight be medicinal extract 1.2 times the thick silica gel mixed sample of 100 order, with weight be medicinal extract 2 times amount 300 order silica gel dress posts carry out silica gel column chromatography, be followed successively by 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 and concentrates, and obtains 8 parts, is wherein followed successively by 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 and concentrates, obtain 8 parts, wherein chloroform-acetone the wash-out with volume proportion being 7:3 is concentrated prompt logical sequence 1,100 half preparative high-performance liquid chromatographic of part peace obtained to be separated, methyl alcohol with 35% is moving phase, Zorbax SB-C18 (21.2 × 250mm, 5 μm) preparative column is stationary phase, flow velocity is 20ml/min, UV-detector determined wavelength is 312nm, each sample introduction 200 μ L, collects the chromatographic peak of 22.4min, repeatedly cumulative rear evaporate to dryness, products therefrom uses pure dissolve with methanol again, then with pure methyl alcohol for moving phase, is separated, obtains this new compound with Sephadex LH-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 6
Tobacco sample derives from Dali, and kind is cloud and mist 200, and tobacco is sampled 3.5kg and pulverize, the alcohol immersion with 100% extracts 5 times, each extraction 24h, Extraction solvent: the weight ratio=3:1 of tobacco leaf, extracting solution merges, filter, concentrating under reduced pressure becomes medicinal extract, obtains medicinal extract 251g.Medicinal extract weight is after the pure dissolve with methanol of its 3.0 times amount, with weight be medicinal extract 0.8 times the thick silica gel mixed sample of 90 order, with weight be medicinal extract 4 times amount 160 order silica gel dress posts carry out silica gel column chromatography, be followed successively by 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 and concentrates, and obtains 8 parts, is wherein followed successively by 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 and concentrates, obtain 8 parts, wherein chloroform-acetone the wash-out with volume proportion being 7:3 is concentrated prompt logical sequence 1,100 half preparative high-performance liquid chromatographic of part peace obtained to be separated, methyl alcohol with 35% is moving phase, Zorbax SB-C18 (21.2 × 250mm, 5 μm) preparative column is stationary phase, flow velocity is 20ml/min, UV-detector determined wavelength is 312nm, each sample introduction 200 μ L, collects the chromatographic peak of 22.4min, repeatedly cumulative rear evaporate to dryness, obtains this new compound.
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 7
Tobacco sample derives from Dali, and kind is cloud and mist 200, tobacco is sampled 3.5kg and is cut into segment, the methyl alcohol soak extraction with 80% 5 times, each extraction 24h, Extraction solvent: the weight ratio=3.5:1 of tobacco leaf, extracting solution merges, filter, concentrating under reduced pressure becomes medicinal extract, obtains medicinal extract 248g.Medicinal extract weight be its 1.5 times amount straight alcohol dissolve after, with weight be medicinal extract 0.85 times the thick silica gel mixed sample of 100 order, with weight be medicinal extract 4 times amount 160 order silica gel dress posts carry out silica gel column chromatography, be followed successively by 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 and concentrates, and obtains 8 parts, is wherein followed successively by 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 and concentrates, obtain 8 parts, wherein chloroform-acetone the wash-out with volume proportion being 7:3 is concentrated prompt logical sequence 1,100 half preparative high-performance liquid chromatographic of part peace obtained to be separated, methyl alcohol with 35% is moving phase, Zorbax SB-C18 (21.2 × 250mm, 5 μm) preparative column is stationary phase, flow velocity is 20ml/min, UV-detector determined wavelength is 312nm, each sample introduction 200 μ L, collects the chromatographic peak of 22.4min, repeatedly cumulative rear evaporate to dryness, obtains this new compound.
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 8
Tobacco sample derives from Dali, and kind is cloud and mist 200, tobacco is sampled 3.5kg and pulverizes, the methyl alcohol soak extraction with 90% 3 times, each extraction 72h, Extraction solvent: the weight ratio=2.5:1 of tobacco leaf, extracting solution merges, filter, concentrating under reduced pressure becomes medicinal extract, obtains medicinal extract 252g.Medicinal extract weight be its 3.0 times amount straight alcohol dissolve after, with weight be medicinal extract 1.2 times the thick silica gel mixed sample of 80 order, with weight be medicinal extract 2 times amount 300 order silica gel dress posts carry out silica gel column chromatography, be followed successively by 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 and concentrates, and obtains 8 parts, is wherein followed successively by 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 and concentrates, obtain 8 parts, wherein chloroform-acetone the wash-out with volume proportion being 7:3 is concentrated prompt logical sequence 1,100 half preparative high-performance liquid chromatographic of part peace obtained to be separated, methyl alcohol with 35% is moving phase, Zorbax SB-C18 (21.2 × 250mm, 5 μm) preparative column is stationary phase, flow velocity is 20ml/min, UV-detector determined wavelength is 312nm, each sample introduction 200 μ L, collects the chromatographic peak of 22.4min, repeatedly cumulative rear evaporate to dryness, products therefrom uses pure dissolve with methanol again, then with pure methyl alcohol for moving phase, is separated, obtains this new compound with Sephadex LH-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 9
Tobacco sample derives from Dali, and kind is cloud and mist 200, tobacco is sampled 3.5kg and pulverizes, the methyl alcohol soak extraction with 100% 4 times, each extraction 50h, Extraction solvent: the weight ratio=3:1 of tobacco leaf, extracting solution merges, filter, concentrating under reduced pressure becomes medicinal extract, obtains medicinal extract 251g.Medicinal extract weight be its 2.5 times amount straight alcohol dissolve after, with weight be medicinal extract 0.8 times the thick silica gel mixed sample of 90 order, with weight be medicinal extract 2.6 times amount 250 order silica gel dress posts carry out silica gel column chromatography, join successively than being 1:0 with volume, 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 and concentrates, and obtains 8 parts, is followed successively by 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 and concentrates, obtain 8 parts, wherein chloroform-acetone the wash-out with volume proportion being 7:3 is concentrated prompt logical sequence 1,100 half preparative high-performance liquid chromatographic of part peace obtained to be separated, methyl alcohol with 35% is moving phase, Zorbax SB-C18 (21.2 × 250mm, 5 μm) preparative column is stationary phase, flow velocity is 20ml/min, UV-detector determined wavelength is 312nm, each sample introduction 200 μ L, collects the chromatographic peak of 22.4min, repeatedly cumulative rear evaporate to dryness, products therefrom uses pure dissolve with methanol again, then with pure methyl alcohol for moving phase, is separated, obtains this new compound with Sephadex LH-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 10
Tobacco sample derives from Dali, and kind is cloud and mist 200, tobacco is sampled 3.5kg and pulverizes, the acetone soak extraction with 60% 5 times, each extraction 72h, Extraction solvent: the weight ratio=2.4:1 of tobacco leaf, extracting solution merges, filter, concentrating under reduced pressure becomes medicinal extract, obtains medicinal extract 250g.Medicinal extract weight be its 2.8 times amount pure acetone dissolve after, with weight be medicinal extract 1.1 times the thick silica gel mixed sample of 80 order, with weight be medicinal extract 2 times amount 160 order silica gel dress posts carry out silica gel column chromatography, be followed successively by 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 and concentrates, and obtains 8 parts, is wherein followed successively by 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 and concentrates, obtain 8 parts, wherein chloroform-acetone the wash-out with volume proportion being 7:3 is concentrated prompt logical sequence 1,100 half preparative high-performance liquid chromatographic of part peace obtained to be separated, methyl alcohol with 35% is moving phase, Zorbax SB-C18 (21.2 × 250mm, 5 μm) preparative column is stationary phase, flow velocity is 20ml/min, UV-detector determined wavelength is 312nm, each sample introduction 200 μ L, collects the chromatographic peak of 22.4min, repeatedly cumulative rear evaporate to dryness, products therefrom uses pure dissolve with methanol again, then with pure methyl alcohol for moving phase, is separated, obtains this new compound with Sephadex LH-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 11
Tobacco sample derives from Dali, and kind is cloud and mist 200, tobacco is sampled 3.5kg and pulverizes, the acetone soak extraction with 90% 3 times, each extraction 24h, Extraction solvent: the weight ratio=2:1 of tobacco leaf, extracting solution merges, filter, concentrating under reduced pressure becomes medicinal extract, obtains medicinal extract 245g.Medicinal extract weight be its 1.5 times amount pure acetone dissolve after, with weight be medicinal extract 1.2 times the thick silica gel mixed sample of 100 order, with weight be medicinal extract 4 times amount 300 order silica gel dress posts carry out silica gel column chromatography, be followed successively by 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 and concentrates, and obtains 8 parts, is wherein followed successively by 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 and concentrates, obtain 8 parts, wherein chloroform-acetone the wash-out with volume proportion being 7:3 is concentrated prompt logical sequence 1,100 half preparative high-performance liquid chromatographic of part peace obtained to be separated, methyl alcohol with 35% is moving phase, Zorbax SB-C18 (21.2 × 250mm, 5 μm) preparative column is stationary phase, flow velocity is 20ml/min, UV-detector determined wavelength is 312nm, each sample introduction 200 μ L, collects the chromatographic peak of 22.4min, repeatedly cumulative rear evaporate to dryness, products therefrom uses pure dissolve with methanol again, then with pure methyl alcohol for moving phase, is separated, obtains this new compound with Sephadex LH-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 12
Tobacco sample derives from Dali, and kind is cloud and mist 200, tobacco is sampled 3.5kg and pulverizes, the acetone soak extraction with 70% 4 times, each extraction 60h, Extraction solvent: the weight ratio=4:1 of tobacco leaf, extracting solution merges, filter, concentrating under reduced pressure becomes medicinal extract, obtains medicinal extract 255g.Medicinal extract weight be its 3.0 times amount pure acetone dissolve after, with weight be medicinal extract 0.8 times the thick silica gel mixed sample of 90 order, 1 with weight be medicinal extract 3.5 times amount 250 order silica gel fill posts carries out silica gel column chromatography, be followed successively by 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 and concentrates, and obtains 8 parts, is wherein followed successively by 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 and concentrates, obtain 8 parts, wherein chloroform-acetone the wash-out with volume proportion being 7:3 is concentrated prompt logical sequence 1,100 half preparative high-performance liquid chromatographic of part peace obtained to be separated, methyl alcohol with 35% is moving phase, Zorbax SB-C18 (21.2 × 250mm, 5 μm) preparative column is stationary phase, flow velocity is 20ml/min, UV-detector determined wavelength is 312nm, each sample introduction 200 μ L, collects the chromatographic peak of 22.4min, repeatedly cumulative rear evaporate to dryness, products therefrom uses pure dissolve with methanol again, then with pure methyl alcohol for moving phase, is separated, obtains this new compound with Sephadex LH-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.
Qualification example 1
The qualification of------compound structure
Compound prepared by Example 1, compound is light yellow gum thing; UV spectrum (solvent is methyl alcohol), λ
max(log ε) 312 (3.22), 280 (3.57), 214 (4.05) nm; Infrared spectra (pressing potassium bromide troche) ν
max3442,2918,1735,1657,1610,1542,1476,1387,1259,1142,1064,869,768cm
-1; High resolution mass spectrum (HRESIMS) provides quasi-molecular ion peak m/z 219.0652 [M-H]
-(calculated value 219.0657).Shown in composition graphs 1 and Fig. 2
1h and
13c NMR spectrum provides a molecular formula C
12h
12o
4, degree of unsaturation is 7.From
1h and
13cNMR composes (attribution data is in table 1) signal can find out in compound have 1,2,4, a 5-quaternary phenyl ring, a 3-hydroxypropanoyl, an oxidation methylene radical, ester carbonyl group, a methyl.Lactone is constituted by Sauerstoffatom according to the HMBC of H-2' with C-3' relevant (Fig. 3) susceptible of proof C-2' and C-3'.-1 of phenyl ring is connected to, according to methyl hydrogen H-1' and C-1, C-2 susceptible of proof methyl substituted relevant with the HMBC of C-3 in C-2 position according to the HMBC of H-8 and C-1, H-6 and C-7 relevant susceptible of proof 3-hydroxypropanoyl.So far the structure of this compound is determined.
Qualification example 2
Compound prepared by Example 2-12 is yellow jelly.Measuring method is identical with embodiment 5, confirms that compound prepared by embodiment 2-12 is described benzo lactone compound---6-(3-hydroxypropanoyl)-5-methyl isobenzofuran-1 (3H)-one.
Arbitrary benzo lactone compound prepared by application examples 1 Example 1-12 carries out the experiment of cigarette additive effect, and test situation is as follows:
Be Hong Yun Red River group product " purple cloud and mist " for interpolation cigarette, often propping up pipe tobacco weight is 0.65g.Above-mentioned benzo lactone compound ethanol is made into 0.65% (m/v, g/mL) solution, add by essence and flavoring agent injector, divide 5 μ L, 10 μ L, 15 μ L, 20 μ L, tetra-injection volumes, the benzo lactone compound of injection accounts for 0.05 ‰, 0.1 ‰, 0.15 ‰, 0.2 ‰ of pipe tobacco total amount respectively, not add benzo lactone compound for contrast.After having injected, at room temperature open wide and put 2h, allow solvent evaporates.Then cigarette sample is balanced 48h under (22 ± 1) DEG C, relative humidity 60% ± 2% condition, smoke panel test for expert sensory.Smoking result shows: in cigarette, add this compound, can soft cigarette smoke, increase the exquisiteness of flue gas, oral cavity moisture feeling has lifting, fragrance more clear, and optimum addition is between 0.05 ‰ ~ 0.15 ‰.The compounds of this invention obviously can improve cigarette smoking quality, can be used as the guiding compound of tobacco aromatics using research and development, and for improving the new additive preparation of cigarette smoking quality.
Claims (8)
1. a kind of benzo lactone compound as shown in formula I,
, formula I;
The called after of this compound: 6-(3-hydroxypropanoyl)-5-methyl isobenzofuran-1 (3
h)-one (6-(3-hydroxypropanoyl)-5-methylisobenzofuran-1 (3
h)-one).
2. the preparation method of benzo lactone compound according to claim 1, is characterized in that, comprise the following steps:
Step (1), medicinal extract extracts: take tobacco leaf as raw material, tobacco leaf is pulverized or is cut into segment, be that Extraction solvent carries out soak extraction with the acetone of the methyl alcohol of concentration expressed in percentage by weight 80% ~ 100%, the ethanol of concentration expressed in percentage by weight 80% ~ 100% or concentration expressed in percentage by weight 60% ~ 90%, Extraction solvent: the weight ratio=2 ~ 4:1 of tobacco leaf, soaks 24 h ~ 72 h, extracts 3 ~ 5 times, united extraction liquid, filtering and concentrating becomes medicinal extract;
Step (2), silica gel column chromatography: the medicinal extract weight that step (1) obtains is that 160 ~ 300 order silica gel dry column-packings of its 2 ~ 4 times amount carry out silica gel column chromatography; With the mixed solvent of chloroform-acetone for eluent carries out gradient elution, thin layer chromatography is followed the tracks of, and merges identical part, collects each several part elutriant and concentrates; During gradient elution, the mixed solvent volume proportion of chloroform-acetone gradually changes to 1:2 from 1:0;
Step (3), high pressure liquid chromatography separation and purification: the mixed solvent wash-out of the chloroform-acetone with volume proportion being 7:3 is collected the concentrated part obtained and namely obtains required benzo lactone compound with high pressure liquid chromatography separation and purification further.
3. benzo lactone compound preparation method according to claim 2, it is characterized in that: in step (3), compound after high pressure liquid chromatography separation and purification uses pure dissolve with methanol again, then with pure methyl alcohol for moving phase, with further gel filtration chromatography separation and purification.
4. benzo lactone compound preparation method according to claim 2, is characterized in that: in step (3), described high pressure liquid chromatography separation and purification is employing 21.2 mm × 250 mm, 5
μthe C of m
18chromatographic column, flow velocity is 20 mL/min, moving phase to be mass concentration be 35% methanol aqueous solution, UV-detector determined wavelength is 312 nm, each sample introduction 200
μl, collects the chromatographic peak of 22.4 min, repeatedly cumulative rear evaporate to dryness.
5. benzo lactone compound preparation method according to claim 2, it is characterized in that: in step (2), described medicinal extract is before silica gel column chromatography,, after medicinal extract dissolves by the pure methyl alcohol of medicinal extract 1.5 ~ 3 times amount, straight alcohol or pure acetone, be 80 ~ 100 order silica gel mixed samples of medicinal extract 0.8 ~ 1.2 times by weight by weight.
6. benzo lactone compound preparation method according to claim 2, it is characterized in that: in step (2), during described gradient elution, the mixed solvent volume proportion of chloroform-acetone is followed successively by 1:0,20:1,9:1,8:2,7:3,6:4,1:1 and 1:2.
7. benzo lactone compound according to claim 1 is improving the application in cigarette smoking quality.
8. benzo lactone compound according to claim 7 is improving the application in cigarette smoking quality, it is characterized in that, adds in pipe tobacco by described benzo lactone compound, and the quality of interpolation is 0.05 ‰-0.15 ‰ of tobacco quality.
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