CN102617659A - Synthesis method for alpha-ionol glucoside, and application of alpha-ionol glucoside to flavoring of cigarettes - Google Patents
Synthesis method for alpha-ionol glucoside, and application of alpha-ionol glucoside to flavoring of cigarettes Download PDFInfo
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- CN102617659A CN102617659A CN2012100603832A CN201210060383A CN102617659A CN 102617659 A CN102617659 A CN 102617659A CN 2012100603832 A CN2012100603832 A CN 2012100603832A CN 201210060383 A CN201210060383 A CN 201210060383A CN 102617659 A CN102617659 A CN 102617659A
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Abstract
The invention discloses a preparation method for alpha-ionol glucoside. The preparation method is characterized by comprising the following steps of: performing glycosylation on bromo-tetracetylglucose and alpha-ionol, and performing deacetylation by using the methanol solution of sodium methoxide to obtain the alpha-ionol glucoside. The preparation method has the advantages that: the chemical synthesis of the alpha-ionol glucoside can be successfully realized; and the method is mild in reaction condition, favorable for post-treatment, safe, reliable and suitable for industrial production. The synthesized alpha-ionol glucoside is applied to the flavoring of cigarettes, so that the sensory quality of the cigarettes can be effectively improved, and the alpha-ionol glucoside has high cigarette flavoring stability and uniformity.
Description
Technical field
Patent of the present invention relates to the synthetic of α-ionol glucoside and perfumed applications in cigarette.α-ionol glucoside has good thermostability at normal temperatures, is heated to 200 ℃ of beginning cracking, and thermo-cracking can produce flavour ingredients such as α-ionol, α-Zi Luolantong, 3-oxo-α-Zi Luolantong, huge beans triolefin.α-ionol glucoside is applied to have good perfuming effect in the cigarette.
Background technology
The applied research of glucosides class fragrance precursor in cigarette, the application patent that abroad occurs being correlated with since the eighties in 20th century.1998, the research of Japanese Hasegawa Spice Co., Ltd. pointed out that glucosides can discharge fragrance matter when heating, improves tobacco and inhales flavor (JP, P 1042846 (1998-02-17)).At present, vanirone-β-D-glucopyranoside allows as fragrance applications in foodstuffs industry and tobacco industry through U.S. spices association of producers (FEMA) assessment.Dube etc. with the vanirone glucosides add in people's cigarette tissue outer odor type cigarette, no biscuit perfume then can smell (US, P 4941486 (1990-07-7)) before this outer odor type cigarette smoking during suction.Kapeer etc. have studied the flavouring effect of glucosides class fragrance precursor extract in the process of burning and sucking; Think that the glucosides class is not cracking fully rapidly in the process of burning and sucking, but slowly discharge aglycon, thereby make evenly (Kapeer G F of every mouthful of concentration of tobacco aroma; Niz S; Drawer T F. Bound aroma compounds in tobacco smoke condensate [J]. Z LebensmUnters Forsch, 1989,188:512-516).In recent years, domestic colleague also begins to pay attention to this type material, takes to the research of this respect.2002; Zhang Pingyi etc. have carried out Study on Pyrolysis to four kinds of glucosides; And draw as drawing a conclusion: the application of glucosides maybe for the preparation high-temperature resistant essence open up a valid approach (Zhang Pingyi, Lu Huixiu, Jin Qizhang etc. Pyrolysis of Glucopyranosides research [J]. fragrance flavor and cosmetic; 2002,3:5-7).2006, Xie Wancui etc. studied the perfuming cigarette and the slow release effect of glucosides class fragrance precursor, and smoking result shows; Add the cigarette sample flue gas of Geraniol glucosides and release perfume evenly, effect is superior to adding the cigarette of Geraniol, has further proved conclusively the slow releasing function (Xie Wancui of Geraniol glucosides; Liu Yi; Pavilion prestige etc. the perfuming cigarette of glucosides class fragrance precursor and slow release effect [J]. tobacco science and technology, 2006,7:40-42).
Glucosides is one of main existence form of flavour ingredient in the tobacco, and the flavouring essence quality of tobacco is had outstanding contribution.Prepare the glucosides class fragrance precursor that tobacco contains through chemosynthesis, and study its cracking character and release behavior, significant for exploitation, the compensating aroma Study on Technology of characteristic perfume material.But the extraction that at present mainly also concentrates on tobacco itself for the research of glucosides class fragrance precursor in the tobacco with separate, the research of its further chemosynthesis is rarely had report.Because the content of glucosides class fragrance precursor is few in the tobacco, can only could really realize its widespread use in cigarette through further investigation to its chemosynthesis.
Ionol and verivate thereof are one type of important fragrance matters in the tobacco, and the tobacco aroma quality is had material impact.Research shows that ionol and verivate thereof are except being produced by the carrotenoid degraded, and glucosides also is its important existence form and one of source, and the cracking of VT alcohols glucosides can produce the tobacco characteristic perfume.Because its content in tobacco is extremely low, and still do not have the relevant report of chemical synthesis and preparation method at present yet, in tobacco, use and be restricted yet.
Summary of the invention
The object of the invention just is being based on above-mentioned prior art situation and a kind of α-compound method of ionol glucoside and the perfumed applications in cigarette thereof that provide; It is the α-ionol glucoside that can discharge tobacco characteristic flavour ingredient through the chemical synthesis preparation; And be applied to perfuming cigarette, improve the organoleptic quality of cigarette.
The present invention is directed to the characteristic of α-ionol glucoside, a kind of preparation method who is suitable for suitability for industrialized production is provided, simultaneously product is used in tobacco, grasped its tobacco flavoring characteristic.The molecular structure of α-ionol glucoside is following:
The objective of the invention is to realize through following technical scheme: the method for α of the present invention-ionol glucoside at first adopts Bromotetraacetylgluc,se and α-ionol to carry out glycosylation reaction; It is deacetylated to adopt the methanol solution of sodium methylate to carry out then, and then obtains α-ionol glucoside.Concrete compound method is following:
(1) glycosylation reaction: α-ionol is dissolved in reaction solvent (like methylene dichloride, toluene, benzene, acetone etc.); Adding is equivalent to the new preparation silver carbonate catalyzer of α-ionol 1% ~ 20% (x) amount and an amount of water-removal additive (like molecular sieve, SODIUM SULPHATE ANHYDROUS 99PCT); After fully stirring 0.5 ~ 1h; Under the reflux state, in reaction system, slowly drip the Bromotetraacetylgluc,se solution that is equivalent to α-ionol 30% ~ 80% (x) amount, after dropwising; Continue reaction 2 ~ 10h, entire reaction course need be carried out under the lucifuge condition.After reaction finishes, remove catalyzer, water-removal additive and reaction solvent, residue is dissolved in ETHYLE ACETATE, and successively with after washing with sodium hydrogen carbonate solution, saturated nacl aqueous solution, frozen water, isolates organic phase, obtains crude product after removing ETHYLE ACETATE.Crude product is carried out the gradient elution silica gel column chromatography, and eluent is sherwood oil and ETHYLE ACETATE mixed solvent, in the elution process in the two ratio of the ascending order of polarity adjustment.Collect R
f(the TLC developping agent is: sherwood oil (60 ℃-90 ℃): ETHYLE ACETATE=4:1), promptly obtain α-ionol tetraacetyl-glucose glycosides, productive rate is about 25% to=0.66 component.The structural characterization result of product is: 1. FT-IR (KBr), ν/cm
-1: 2921 (ν
(C-H):-CH
3,-CH
2-), 1755 (ν
(C=O):-COOCH
3), 1664 (ν
(C=C)), 1618 (ν
(C=C)), 1452 (δ
As (C-H):-CH
3,-CH
2-), 1360 (δ
S (C-H):-CH
3), 1141 (ν
(C-O-C)), 1049 (ν
(C-O-C)); 2. ESI-MS, m/z:547 (M+Na)
+3.
1H-NMR (CDCl
3), δ: 0.87 (6H; H-11, H-12), 1.16 (2H; H-2), 1.24 (3H; H-13), 1.61 (3H; H-10), 1.91 (2H; H-3), 2.03 (12H; 4H-Ac), 2.14 (1H; H-6), 4.01 (2H; H-6'), 4.10 (1H; H-5'), 4.17 (1H; H-9), 4.37 (1H; H-4'), 4.85 (1H; H-3'), 5.10 (1H; H-2'), 5.25 (1H; H-1', J
1-2=7.82Hz), 5.35 (1H; H-7), 5.41 (1H; H-8), 5.51 (1H; H-4).The J of H-1'
1-2=7.82Hz explains that product is the beta comfiguration glucosides.The reaction formula of this step reaction is following:
(2) deacetylated reaction: α-ionol tetraacetyl-glucose glycosides is well-dispersed in the methyl alcohol; And to the methanol solution that wherein slowly drips the sodium methylate that is equivalent to α-ionol tetraacetyl-glucose glycosides 1% ~ 10% (massfraction) amount; After dropwising, continue stirring reaction 0.5 ~ 2h.After reaction finishes, remove methyl alcohol, residue carries out the gradient elution silica gel column chromatography, and eluent is ETHYLE ACETATE and methanol mixed solvent, adjusts the ratio of the two in the elution process in the ascending order of polarity.Collect R
f(the TLC developping agent is: ETHYLE ACETATE: methyl alcohol=8:1), promptly obtain α-ionol glucoside, productive rate is about 89% to=0.55 component.The structural characterization result of product is: 1. FT-IR (KBr), ν/cm
-1: 3409 (ν
(O-H):, 2915 (ν
(C-H):-CH
3,-CH
2-), 1647 (ν
(C=C)), 1451 (δ
As (C-H):-CH
3,-CH
2-), 1373 (δ
S (C-H):-CH
3), 1077 (ν
(C-O-C)), 1038 (ν
(C-O-C)); 2. ESI-MS, m/z:379 (M+Na)
+, 735 (2M+Na)
+3.
1H-NMR (MeOD), δ: 0.89 (6H; H-11, H-12), 1.18 (2H; H-2), 1.27 (3H; H-13), 1.60 (3H; H-10), 2.01 (2H; H-3), 2.14 (1H; H-6), 3.17 (2H; H-6'), 3.27 (1H; H-5'), 3.34 (1H; H-9), 3.67 (1H; H-4'), 3.84 (1H; H-3'), 4.36 (1H; H-2'), 4.44 (1H; H-1', J
1-2=7.64Hz), 5.36 (1H; H-7), 5.43 (1H; H-8), 5.54 (1H; H-4).The J of H-1'
1-2=7.64Hz explains that product is the beta comfiguration glucosides.The reaction formula of this step reaction is following:
The characteristics of synthesizing α-ionol glucoside through aforesaid method are:
(1) α-ionol glucoside has good thermostability, thermogravimetric (TGA) analysis revealed, and the glycosidic link of product ruptures about 200 ℃.
(2) α-ionol glucoside thermo-cracking can produce flavour ingredients such as α-ionol, α-Zi Luolantong, 3-oxo-α-Zi Luolantong, huge beans triolefin.
The synthetic α of the institute-above-mentioned thermal properties of ionol glucoside has proved its application possibility in perfuming cigarette.
Through the synthetic α of aforesaid method institute-effect of ionol glucoside in tobacco flavoring is following:
(1) the synthetic α of institute-ionol glucoside is pressed in the addition adding cigarette of 10-500ppm, can effectively be improved fragrance matter, perfume quantity, assorted gas, the fine and smooth soft degree of cigarette smoke and return sweet sense, product has good perfuming cigarette effect.The GC/MS analysis revealed of sample cigarette mainstream flue gas granule phase substance; After adding α-ionol glucoside; Can effectively discharge characteristic flavour ingredients such as α-ionol, α-Zi Luolantong, 3-oxo-α-Zi Luolantong in the main flume, and the burst size of Megastigmatrienone can increase also.
(2) institute's synthetic α-ionol glucoside has good perfuming cigarette stability.After cigarette sample opened wide and places January, the perfuming effect of product remained unchanged basically.The GC/MS analysis revealed of sample cigarette mainstream flue gas granule phase substance adds the cigarette sample of α-ionol glucoside and places front and back, and the burst size of characteristic flavour ingredient almost remains unchanged.
(3) flavouring essence quality of section has good consistence before and after the cigarette of the interpolation synthetic α of institute-ionol glucoside.The GC/MS analysis revealed by mouth flue gas granule phase substance of sample cigarette, the burst size of each mouthful of characteristic flavour ingredient number has good homogeneous property.
Advantage of the present invention:
Can successfully realize the chemosynthesis of α-ionol glucoside through compound method of the present invention, reaction conditions is gentle, and aftertreatment is simple, and is safe and reliable, is suitable for implementing suitability for industrialized production.The synthetic α of institute of the present invention-ionol glucoside has good thermostability, and thermo-cracking can discharge flavour ingredients such as α-ionol, α-Zi Luolantong, 3-oxo-α-Zi Luolantong, huge beans triolefin; Be applied in the cigarette; Can effectively discharge characteristic flavour ingredients such as α-ionol, α-Zi Luolantong, 3-oxo-α-Zi Luolantong; Can also increase simultaneously the burst size of Megastigmatrienone; Thereby thereby obviously can effectively improve the organoleptic quality of cigarette, and have good perfuming cigarette stability and homogeneity.
Description of drawings
Fig. 1 is thermogravimetric analysis (TGA) figure of the synthetic α of institute of the present invention-ionol glucoside.
Embodiment
The present invention does below in conjunction with embodiment and further describes:
Embodiment 1: α-ionol tetraacetyl-glucose glycosides synthetic
20mmol α-ionol is dissolved in the 40mL methylene dichloride; Add 2mmol silver carbonate and 5g activation 4 molecular sieves; After magnetic agitation is fully disperseed 30min; Reflux state slowly drips the dichloromethane solution (also can be toluene, benzene or acetone soln) that 20 mL contain the 16mmol Bromotetraacetylgluc,se down, dropwises continued stirring and refluxing reaction 6h.Entire reaction course needs lucifuge to carry out.After reaction finishes; Filter, revolve steam slurry like material, then slurry like material is dissolved in the 200mL ETHYLE ACETATE; Use 2 * 100mL saturated sodium bicarbonate solution, 2 * 100mL saturated nacl aqueous solution, the washing of 2 * 100mL frozen water successively; The anhydrous sodium sulfate drying organic phase is revolved to steam and is removed ETHYLE ACETATE, and soup compound is carried out the gradient elution silica gel column chromatography.The gradient ratio of eluent is followed successively by sherwood oil: ETHYLE ACETATE=1:0; 20:1; 15:1; 10:1; 8:1; 6:1; 4:1.Collect R
f(the TLC developping agent is: sherwood oil (60 ℃-90 ℃): ETHYLE ACETATE=4:1), promptly obtain α-ionol tetraacetyl-glucose glycosides 2.1g, productive rate is about 25% to=0.66 component.
Embodiment 2: the synthetic and thermal properties of α-ionol glucoside
1.0g α-ionol tetraacetyl-glucose glycosides is added in the 20mL methyl alcohol; Fully stir; The formation unit for uniform suspension, to wherein slowly dripping the methanol solution that 1mL contains the 0.05g sodium methylate, the phenomenon of light-yellow precipitate will appear separating out again after change is clarified earlier in reaction system under stirring.Dropwise, continue stirring reaction 30min.After reaction finishes, revolve to steam and remove methyl alcohol, residue carries out the gradient elution silica gel column chromatography.The gradient ratio of eluent is followed successively by ETHYLE ACETATE: methyl alcohol=1:0; 30:1; 25:1; 20:1; 15:1; 10:1; 8:1.Collect R
f(the TLC developping agent is: ETHYLE ACETATE: methyl alcohol=8:1), promptly obtain α-ionol glucoside 0.6g, productive rate is about 89% to=0.55 component.
Thermogravimetric analysis (TGA) result of the synthetic α of institute-ionol glucoside
as shown in Figure 1.
The TGA analysis revealed, the glycosidic link fracture temperature of α-ionol glucoside is 190 ℃, the fastest weightless temperature is 210 ℃.
The Py-GC/MS analytical results such as the following table of the synthetic α of institute-ionol glucoside:
The Py-GC/MS analysis revealed, the synthetic α of institute-ionol glucoside thermo-cracking can produce flavour ingredients such as α-ionol, α-Zi Luolantong, 3-oxo-α-Zi Luolantong, huge beans triolefin.
Embodiment 3: the perfuming cigarette of α-ionol glucoside is used
α-ionol glucoside is dissolved in the ethanol; And be expelled in the blank cigarette of fire-cured tobacco type that pre-equilibration crosses by the addition of 100ppm; Balance was added the changing conditions of front and back aroma characteristic, flue gas characteristic and mouthfeel characteristic and is carried out sensory evaluation after 48 hours to cigarette under the condition of 22 ℃ of temperature, relative humidity 60%.Sensory evaluation is the result show; α-ionol glucoside has good perfuming cigarette effect; Can obviously improve fragrance matter, perfume quantity, assorted gas, the fine and smooth soft degree of cigarette smoke and return sweet sense, and the flavouring essence quality of section has good consistence before and after the Cigarette.The sample cigarette opens wide the sensory evaluation of placing after 1 month and shows, the organoleptic quality of sample cigarette changes not obvious before and after placing.
The release conditions and the unlimited burst size of placing characteristic flavour ingredient after 1 month of adding the cigarette sample main flume characteristic flavour ingredient of α-ionol glucoside change like following table:
Can find out by table; Compare with blank cigarette; Add behind α-ionol glucoside the main flume grain and newly produced α-ionol, α-Zi Luolantong, 3-oxo-α-Zi Luolantong in mutually, and the burst size of four kinds of isomer of Megastigmatrienone also all increases.The sample cigarette was placed after 1 month, and the burst size of various characteristic flavour ingredients almost remains unchanged in the main flume, and this has proved that also α-ionol glucoside has satisfactory stability property on perfuming cigarette is used.
Add α-ionol glucoside cigarette sample main flume characteristic flavour ingredient by mouthful release conditions such as following table:
Can find out that by table the burst size of adding each mouthful of characteristic flavour ingredient number of the glucosidic cigarette of α-ionol has good homogeneous property.
Claims (9)
1. the preparation method of α-ionol glucoside; It is characterized in that: the glycosylation reaction that at first adopts Bromotetraacetylgluc,se and α-ionol; It is deacetylated to adopt the methanol solution of sodium methylate to carry out then, and then obtains α-ionol glucoside, and concrete steps are following:
Glycosylation reaction: α-ionol is dissolved in reaction solvent; Add new preparation silver carbonate catalyzer and the water-removal additive be equivalent to α-ionol 1% ~ 20% x amount, fully stir 0.5 ~ 1h after, under the reflux state; In reaction system, slowly drip the Bromotetraacetylgluc,se solution that is equivalent to α-ionol 30% ~ 80% x amount; After dropwising, continue reaction 2 ~ 10h, entire reaction course is carried out under the lucifuge condition; After reaction finishes, remove catalyzer, water-removal additive and reaction solvent, residue is dissolved in ETHYLE ACETATE, and after washing with saturated sodium bicarbonate solution, saturated nacl aqueous solution, frozen water successively, isolates organic phase, obtains crude product after removing ETHYLE ACETATE; Crude product is carried out the gradient elution silica gel column chromatography, collect R
f=0.66 component promptly obtains α-ionol tetraacetyl-glucose glycosides;
Deacetylated reaction: α-ionol tetraacetyl-glucose glycosides is well-dispersed in the methyl alcohol; And to the methanol solution that wherein slowly drips the sodium methylate that is equivalent to α-ionol tetraacetyl-glucose glycosides 1% ~ 10% massfraction amount; After dropwising, continue stirring reaction 0.5 ~ 2h; Reaction is removed methyl alcohol after finishing, and residue carries out the gradient elution silica gel column chromatography, collects R
f=0.55 component promptly obtains α-ionol glucoside.
2. the preparation method of α according to claim 2-ionol glucoside is characterized in that: reaction solvent described in the glycosylation reaction step is methylene dichloride, toluene, benzene or acetone.
3. the preparation method of α according to claim 2-ionol glucoside is characterized in that: said water-removal additive is molecular sieve or SODIUM SULPHATE ANHYDROUS 99PCT.
4. the preparation method of α according to claim 2-ionol glucoside; It is characterized in that: the eluent that the gradient elution in the glycosylation reaction step uses is sherwood oil and ETHYLE ACETATE mixed solvent, in the elution process in the two ratio of the ascending order of polarity adjustment.
5. the preparation method of α according to claim 2-ionol glucoside is characterized in that: collect R
f=0.66 component, used TLC developping agent is: sherwood oil: ETHYLE ACETATE=4:1.
6. the preparation method of α according to claim 2-ionol glucoside; It is characterized in that: the eluent that the gradient elution in the deacetylated reactions step uses is ETHYLE ACETATE and methanol mixed solvent, in the elution process in the two ratio of the ascending order of polarity adjustment.
7. the preparation method of α according to claim 2-ionol glucoside is characterized in that: collect R
f=0.55 component, the TLC developping agent is: ETHYLE ACETATE: methyl alcohol=8:1.
8. α-the application of ionol glucoside in perfuming cigarette described in claim 1; It is characterized in that: α-ionol glucoside is added in the cigarette; Can effectively discharge characteristic flavour ingredients such as α-ionol, α-Zi Luolantong, 3-oxo-α-Zi Luolantong; Simultaneously can also increase the burst size of Megastigmatrienone, thereby effectively improve fragrance matter, perfume quantity, assorted gas, the fine and smooth soft degree of cigarette smoke and return sweet sense.
9. the α according to claim 8-application of ionol glucoside in perfuming cigarette is characterized in that: α-ionol glucoside joins in the cigarette by the addition of 10-500ppm.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103159806A (en) * | 2013-02-27 | 2013-06-19 | 湖北中烟工业有限责任公司 | Preparation method of vanillin glucoside and application of vanillin glucoside in tobacco flavoring |
| CN106167508A (en) * | 2016-07-13 | 2016-11-30 | 上海应用技术学院 | A kind of glucoside compounds with violet fragrance and preparation method thereof |
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| CN101444334A (en) * | 2008-12-26 | 2009-06-03 | 河南中烟工业公司 | Application of 6-0- acetyl-2,3,4-tri-0-isobutyryl-Beta-D-glucopyranose in cigarette |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103159806A (en) * | 2013-02-27 | 2013-06-19 | 湖北中烟工业有限责任公司 | Preparation method of vanillin glucoside and application of vanillin glucoside in tobacco flavoring |
| CN103159806B (en) * | 2013-02-27 | 2015-12-02 | 湖北中烟工业有限责任公司 | The preparation method of vanillin food grade,1000.000000ine mesh glucoside and the application in tobacco flavoring thereof |
| CN106167508A (en) * | 2016-07-13 | 2016-11-30 | 上海应用技术学院 | A kind of glucoside compounds with violet fragrance and preparation method thereof |
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Application publication date: 20120801 |