CN101444334A - Application of 6-0- acetyl-2,3,4-tri-0-isobutyryl-Beta-D-glucopyranose in cigarette - Google Patents
Application of 6-0- acetyl-2,3,4-tri-0-isobutyryl-Beta-D-glucopyranose in cigarette Download PDFInfo
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- CN101444334A CN101444334A CNA2008102315250A CN200810231525A CN101444334A CN 101444334 A CN101444334 A CN 101444334A CN A2008102315250 A CNA2008102315250 A CN A2008102315250A CN 200810231525 A CN200810231525 A CN 200810231525A CN 101444334 A CN101444334 A CN 101444334A
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Abstract
The invention belongs to the field of tobacco spices, and particularly relates to the application of 6-0- acetyl-2,3,4-tri-0-isobutyryl-Beta-D-glucopyranose in cigarette. The invention is characterized in that 6-0- acetyl-2,3,4-tri-0-isobutyryl-Beta-D-glucopyranose is added into cigarette in the proportion of 0.05-10 Mug/g to tobacco. By adding 6-0- acetyl-2,3,4-tri-0-isobutyryl-Beta-D-glucopyranose in cigarette, the application can acquire the optimum effect.
Description
(1) technical field
The invention belongs to the tobacco spice field, particularly 6-O-acetyl group-2,3, the 4-three-O-isobutyryl-β-application of D-glucopyranose in cigarette.
(2) background technology
The organic acidity composition that contains in flue-cured tobacco and the Turkish tobaccos has tangible correlation to its fragrance.The tobacco leaf that is rich in fragrance, organic acid composition content height; Lack the tobacco leaf of fragrance, organic acid composition content is low.Flue-cured tobacco that volatile acids content is higher or Turkish tobaccos, it is pure and mild to it is generally acknowledged that its flue gas is inhaled flavor, gives off a strong fragrance, and clearly wets one's whistle.But, then can make flue gas produce pungent scorching hot sensation if volatile acids content is too high.Airing cigarette volatile acids content is generally lower, and flue gas alkalescence is stronger, and excitant is bigger, therefore often will replenish organic acid in the production of cigarettes process, and is jealous to improve.Different organic acids is to the difference that influences of the sucking quality of tobacco: lower fatty acid is given flue gas and is inhaled flavor and fragrance characters, and higher fatty acids makes the jealous improvement of cigarette, smoke alcohol and reaches agreeable to the taste then more by regulating the pH value of tobacco.
Isobutyric acid is to the fragrance of flue gas and jealously have an earth shaking effect: it can give fragrance as flue gas cheese and the fruit and pure and mild suction flavor.Yet, because isobutyric acid has volatile characteristic as other low carbon fatty acids, when processing and deposit, cigarette can volatilize gradually, the most important thing is cigarette when burning and sucking not only the combustion zone have extremely high temperature, and also there is quite high temperature the pyrolysis distillation zone, the volatilization that isobutyric acid can be rapid when therefore burning and sucking, thus the quality of cigarette smoke influenced and differ in jealous front and back.
Discover; 6-O-acetyl group-2; 3; 4-three-O-isobutyryl-β-D-glucopyranose (shown in I) is that Turkish tobaccos burn and suck the isobutyric precursor of important fragrance matter in the flue gas of back; it has highly stable physical characteristic; can only under the condition of high temperature cracking take place, discharge free isobutyric acid.Therefore the burning and sucking in the process of whole cigarette, it can stably discharge the isobutyric acid of equivalent from start to finish, when improving the flue gas sucking quality, makes the jealous self-consistentency of flue gas, thereby has reached the purpose of perfuming preferably.But 6-O-acetyl group-2; 3,4-three-O-isobutyryl-β-D-glucopyranose belongs to the natural compound that is present in the tobacco, therefore for 6-O-acetyl group-2; 3, the 4-three-O-isobutyryl-β-mechanism that the D-glucopyranose acts in tobacco and the research of its application are restricted always.
Formula I
(3) summary of the invention
The object of the present invention is to provide 6-O-acetyl group-2,3, the 4-three-O-isobutyryl-β-application of D-glucopyranose in cigarette, to obtain 6-O-acetyl group-2,3,4-three-O-isobutyryl-β-D-glucopyranose makes an addition to the optimum efficiency in the cigarette.
The technical solution used in the present invention is as follows:
6-O-acetyl group-2,3, the 4-three-O-isobutyryl-β-application of D-glucopyranose in cigarette makes an addition in the cigarette with the amount of 0.05-10 μ g/g tobacco.
Preferably, addition is more preferably 0.5 μ g/g of 0.1-5 μ g/g tobacco.
The 6-O-acetyl group-2 that the present invention will manually synthesize, 3,4-three-O-isobutyryl-β-D-glucopyranose adds cigarette, burn and suck by smoking machine, contain isobutyric granule phase substance with the cambridge filter reservation, pass through suitable processing then, carry out the analysis of qualitative, quantitative with GC-MS, carry out check analysis by the blank sample that does not add this glucose ester together, thereby determine its cracking rate of transform when burning and sucking; Specific as follows:
1. cigarette Zhi Yaoqiu and puffing regimens
Cigarette Zhi Yaoqiu: cigarette weight 0.89g; Cigarette props up resistance to suction 1000pa;
Cigarette props up specification 84mm * 24.5mm; Filter length 30mm;
Puffing regimens: 23 ℃ of environment temperatures; Relative humidity 62%; Air velocity 200mm/s;
2. sample treatment
Measure a certain amount of 98% the concentrated sulfuric acid, add an amount of distilled water it is mixed with 20% sulfuric acid solution; Take by weighing a certain amount of sodium hydrate solid, it is dissolved in be mixed with 5% dilute sodium hydroxide aqueous solution in an amount of water; 6.000g formula (I) compound is dissolved in an amount of table perfume (or spice), then spray is added in the 10kg pipe tobacco equably, rolling into the test cigarette props up, choose 60 test cigarettes that cigarette weight, resistance to suction meet the cigarette product standard-required, place the environment balance 24h of relative humidity 65% and temperature (22 ± 2) ℃, under standard conditions, aspirate with the SM400 smoking machine, 7 mouthfuls of average puff numbers, cigarette props up and burns and sucks length 46mm, captures the flue gas granule phase substance with cambridge filter, and every filter disc captures the flue gas granule phase substance of 5 cigarette.Inhale and finish, take out filter disc, with the granule phase substance that 30mL * 12 cambridge filters of 4 dichloromethane extractions are held back, extract is used 30mL * 45% sodium hydrate aqueous solution extraction again, after adding 45mL 20% sulfuric acid in the extract, use 50mL * 3 dichloromethane extractions again, add the 20g anhydrous sodium sulfate drying in the extract, filter, filtrate water-bath under normal pressure is concentrated into 2.0mL.The flue gas treatment fluid that contrast is handled by same puffing regimens and method for the cigarette that does not add formula (I) compound.
3. the preparation of standard liquid and qualitative and quantitative analysis
Take by weighing isobutyric acid 0.0118g, be settled to 25mL with carrene, be mixed with standard sample solution, concentration is 0.472mg/mL, and stepwise dilution is to needed concentration during use.(internal standard i.d.), takes by weighing the 0.0401g acetoxyphenyl, is settled to 25mL with carrene, marks standard liquid in being made into, and concentration is 1.604mg/mL as interior mark with acetoxyphenyl.
Utilize GC-MS to analyze, contrast does not add in the cigarette mainstream flue gas granule phase substance of formula I isobutyric acid in the isobutyric acid and the cigarette mainstream flue gas granule phase substance that has added formula I compound, as shown in Figure 1, 2, can find to add that isobutyric content increases widely in the cigarette granule phase substance of formula I compound.
Simultaneously wherein isobutyric acid content is carried out quantitative analysis, and to obtain the cleavage rate of formula I in cigarette according to the amount of the formula I compound that adds be 26.10 μ g/mg, and promptly 1mg formula I compound is added in the cigarette through cracking and discharges and the isobutyric acid transferred in the main flume granule phase substance is 26.10 μ g.
The GC-MS condition is as follows: (1) chromatographic condition: HP-5 chromatographic column (30m * 250 μ m * 0.25 μ m), adopt temperature programming: 45 ℃ of initial temperature, rise to 60 ℃ with 5 ℃/min, rise to 70 ℃ with 2 ℃/min again, be raised to 130 ℃ with 10 ℃/min again, prolong and hold 3min.250 ℃ of injector temperatures; Carrier gas is a high-pure helium, flow velocity 1.0mL/min; Sample size 2.0 μ L, split ratio 100:1.(2) mass spectrum condition: the ionization mode is electron bombard, electron energy 70eV, 280 ℃ of interface temperature, electron multiplier voltage 1.89KV; Sweep limits 35-500u adopts the ion scan mode of selecting, and isobutyric acid selects 55,73 and 88, and acetoxyphenyl selects 94 and 136.
Above cleavage rate is to draw under the isobutyric acid situation that exists in not considering mainstream smoke gas phase object and flow measurement flue gas.
Described formula I compound can prepare according to laxative remedy:
1) be raw material with 6-O-trityl-β-D-methyl glucopyranoside shown in the formula (II) and isobutyric anhydride, with the pyridine is solvent, be heated to 70-130 ℃ under the stirring, after reacting completely, cooling and reactant liquor being added in the mixed liquor of frozen water and glacial acetic acid is reacted, and obtains 2,3 shown in the formula (III) behind the recrystallization, 4-three isobutyric acids-6-O-trityl-β-D-methyl glucopyranoside ester, its Chinese style (II) compound feeds intake amount of substance than being 3-8:1 with isobutyric anhydride; Whenever the compound (II) that rubs needs to add 1-6L pyridine, 15-25L frozen water and 2-10L glacial acetic acid;
2) formula (III) compound is added distilled water after with sour A dissolving again and add hot reflux, stop heating behind 15～180min and remove and to anhydrate and acid, add capacity methyl alcohol, after the sedimentation and filtration that generates removed, the crystallization of laying equal stress on except that desolvating again obtains the compound 2 shown in the formula (IV), 3,4-three isobutyric acids-β-D-methyl glucopyranoside ester, sour A are one of following: the acetic acid solution of the glacial acetic acid solution of glacial acetic acid, saturated HBr, hydrochloric acid, p-methyl benzenesulfonic acid or saturated hydrochloric acid; Rate of charge adds 1-5L acid A and 100～1000mL distilled water meter according to every 1mol compound (III);
3) formula (IV) compound is dissolved in the pyridine, add acetylation reagent then, fully behind the reaction 1-24h, separation and purification obtains the 6-O-acetyl group-2 shown in the formula (V), 3,4-three-O-isobutyryl-β-D-methyl glucopyranoside, its Chinese style (IV) compound feeds intake amount of substance than being 1:1-6 with acetylation reagent, and every 1mol compound (IV) adds 50～500mL pyridine;
4) formula (V) compound is dissolved in the glacial acetic acid solution of anhydrous HBr that mass concentration is 20-50%, fully mixing the back adds in the carrene, wash to neutral back drying, except that desolvating, and then will be dissolved in except that the material after desolvating in the acetone soln, back flow reaction 1-6h behind the adding silver carbonate, promptly get described formula (I) compound after separating purification, the rate of charge of described each material is glacial acetic acid solution, the acetone soln of 1-10L, the 2-20g silver carbonate that every 1mol compound (V) adds the anhydrous HBr of 1-5L.
Formula (II) formula (III)
Formula (IV) formula (V)
(4) description of drawings
Fig. 1 has added isobutyric gas chromatogram in the main flume granule phase substance of cigarette of formula I compound;
Fig. 2 is an isobutyric gas chromatogram in the main flume granule phase substance of cigarette of not adding type I compound.
(5) specific embodiment:
Below with specific embodiment technical scheme of the present invention is described, but protection scope of the present invention is not limited thereto:
Embodiment 1-5
Take by weighing 0.0005g respectively, 0.0025g, 0.025g, 0.25g and 1.25g acetate three isobutyric acid glucopyranosyl esters (formula (I) compound), be dissolved in respectively in 200mL 95% ethanol, add respectively in the process of perfuming in Deidro Deluxe (golden yellow firmly) cigarette shreds of 50kg, carry out cigarette, screening meets following cigarette Zhi Yaoqiu (cigarette weight 0.89g; Cigarette props up resistance to suction 1000pa; Cigarette props up specification 84mm * 24.5mm; Filter length 30mm) each 100 of cigarette are 22 ± 1 ℃ in temperature, and humidity is in 65% ± 3% the temperature and humidity regulator behind the equilibrium water conten, smokes panel test with the blank sample contrast of handling through the same terms equilibrium water conten.The result is as shown in table 1:
Table 1 smoking result
Claims (3)
1.6-O-acetyl group-2; 3; 4-three-O-isobutyryl-β-the application of D-glucopyranose in cigarette, described 6-O-acetyl group-2,3; 4-three-O-isobutyryl-β-D-glucopyranose is suc as formula shown in (I); it is characterized in that 6-O-acetyl group-2,3; 4-three-O-isobutyryl-β-D-glucopyranose makes an addition in the cigarette with the amount of 0.05-10 μ g/g tobacco
Formula I.
2. 6-O-acetyl group-2,3 as claimed in claim 1, the 4-three-O-isobutyryl-β-application of D-glucopyranose in cigarette is characterized in that, addition is a 0.1-5 μ g/g tobacco.
3. 6-O-acetyl group-2,3 as claimed in claim 2, the 4-three-O-isobutyryl-β-application of D-glucopyranose in cigarette is characterized in that, addition is 0.5 μ g/g tobacco.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2008102315250A CN101444334A (en) | 2008-12-26 | 2008-12-26 | Application of 6-0- acetyl-2,3,4-tri-0-isobutyryl-Beta-D-glucopyranose in cigarette |
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| Application Number | Priority Date | Filing Date | Title |
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| CNA2008102315250A CN101444334A (en) | 2008-12-26 | 2008-12-26 | Application of 6-0- acetyl-2,3,4-tri-0-isobutyryl-Beta-D-glucopyranose in cigarette |
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| CN101444334A true CN101444334A (en) | 2009-06-03 |
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| CNA2008102315250A Pending CN101444334A (en) | 2008-12-26 | 2008-12-26 | Application of 6-0- acetyl-2,3,4-tri-0-isobutyryl-Beta-D-glucopyranose in cigarette |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102617659A (en) * | 2012-03-09 | 2012-08-01 | 中国烟草总公司郑州烟草研究院 | Synthesis method for alpha-ionol glucoside, and application of alpha-ionol glucoside to flavoring of cigarettes |
| CN104323419A (en) * | 2014-09-03 | 2015-02-04 | 湖南中烟工业有限责任公司 | Application of pyridine zinc complex in tobacco product |
| CN110477439A (en) * | 2019-07-09 | 2019-11-22 | 河南中烟工业有限责任公司 | For heating the sugar ester essence and reconstituted tobacoo and the cigarette that do not burn of the cigarette that do not burn |
| CN111748410A (en) * | 2020-07-01 | 2020-10-09 | 云南绅博源生物科技有限公司 | Sweet essence for adding to tobacco and preparation method thereof |
-
2008
- 2008-12-26 CN CNA2008102315250A patent/CN101444334A/en active Pending
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102617659A (en) * | 2012-03-09 | 2012-08-01 | 中国烟草总公司郑州烟草研究院 | Synthesis method for alpha-ionol glucoside, and application of alpha-ionol glucoside to flavoring of cigarettes |
| CN104323419A (en) * | 2014-09-03 | 2015-02-04 | 湖南中烟工业有限责任公司 | Application of pyridine zinc complex in tobacco product |
| CN104323419B (en) * | 2014-09-03 | 2016-07-13 | 湖南中烟工业有限责任公司 | The application in tobacco product of the pyridine Zn complex |
| CN110477439A (en) * | 2019-07-09 | 2019-11-22 | 河南中烟工业有限责任公司 | For heating the sugar ester essence and reconstituted tobacoo and the cigarette that do not burn of the cigarette that do not burn |
| CN110477439B (en) * | 2019-07-09 | 2022-02-25 | 河南中烟工业有限责任公司 | Sugar ester essence for heating non-burning cigarette, tobacco sheet and non-burning cigarette |
| CN111748410A (en) * | 2020-07-01 | 2020-10-09 | 云南绅博源生物科技有限公司 | Sweet essence for adding to tobacco and preparation method thereof |
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Open date: 20090603 |