CN114315586B - Acacia vanillate and preparation method and application thereof in tobacco industry - Google Patents
Acacia vanillate and preparation method and application thereof in tobacco industry Download PDFInfo
- Publication number
- CN114315586B CN114315586B CN202111590480.8A CN202111590480A CN114315586B CN 114315586 B CN114315586 B CN 114315586B CN 202111590480 A CN202111590480 A CN 202111590480A CN 114315586 B CN114315586 B CN 114315586B
- Authority
- CN
- China
- Prior art keywords
- farnesyl
- preparation
- tobacco
- vanillic acid
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 235000002637 Nicotiana tabacum Nutrition 0.000 title claims abstract description 29
- 238000002360 preparation method Methods 0.000 title claims description 29
- 235000010643 Leucaena leucocephala Nutrition 0.000 title description 3
- 241000220479 Acacia Species 0.000 title 1
- 244000061176 Nicotiana tabacum Species 0.000 title 1
- WKOLLVMJNQIZCI-UHFFFAOYSA-M vanillate Chemical compound COC1=CC(C([O-])=O)=CC=C1O WKOLLVMJNQIZCI-UHFFFAOYSA-M 0.000 title 1
- 241000208125 Nicotiana Species 0.000 claims abstract description 28
- -1 farnesyl vanillate Chemical compound 0.000 claims abstract description 25
- 239000003205 fragrance Substances 0.000 claims abstract description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 30
- 150000001875 compounds Chemical class 0.000 claims description 24
- 235000013599 spices Nutrition 0.000 claims description 22
- YQUVCSBJEUQKSH-UHFFFAOYSA-N protochatechuic acid Natural products OC(=O)C1=CC=C(O)C(O)=C1 YQUVCSBJEUQKSH-UHFFFAOYSA-N 0.000 claims description 17
- TUUBOHWZSQXCSW-UHFFFAOYSA-N vanillic acid Natural products COC1=CC(O)=CC(C(O)=O)=C1 TUUBOHWZSQXCSW-UHFFFAOYSA-N 0.000 claims description 17
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 12
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 239000003995 emulsifying agent Substances 0.000 claims description 8
- 239000000796 flavoring agent Substances 0.000 claims description 7
- CRDAMVZIKSXKFV-FBXUGWQNSA-N (2-cis,6-cis)-farnesol Chemical compound CC(C)=CCC\C(C)=C/CC\C(C)=C/CO CRDAMVZIKSXKFV-FBXUGWQNSA-N 0.000 claims description 6
- 239000000260 (2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol Substances 0.000 claims description 6
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 claims description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 6
- 239000002270 dispersing agent Substances 0.000 claims description 6
- 229940043259 farnesol Drugs 0.000 claims description 6
- 229930002886 farnesol Natural products 0.000 claims description 6
- 235000019634 flavors Nutrition 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- CRDAMVZIKSXKFV-UHFFFAOYSA-N trans-Farnesol Natural products CC(C)=CCCC(C)=CCCC(C)=CCO CRDAMVZIKSXKFV-UHFFFAOYSA-N 0.000 claims description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 5
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 claims description 4
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- XJUZRXYOEPSWMB-UHFFFAOYSA-N Chloromethyl methyl ether Chemical compound COCCl XJUZRXYOEPSWMB-UHFFFAOYSA-N 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 3
- 229940061627 chloromethyl methyl ether Drugs 0.000 claims description 3
- 229940075507 glyceryl monostearate Drugs 0.000 claims description 3
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 2
- 239000004166 Lanolin Substances 0.000 claims description 2
- 239000002202 Polyethylene glycol Substances 0.000 claims description 2
- 229920001213 Polysorbate 20 Polymers 0.000 claims description 2
- 229920001214 Polysorbate 60 Polymers 0.000 claims description 2
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 claims description 2
- 235000013871 bee wax Nutrition 0.000 claims description 2
- 239000012166 beeswax Substances 0.000 claims description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 claims description 2
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 2
- 239000000194 fatty acid Substances 0.000 claims description 2
- 229930195729 fatty acid Natural products 0.000 claims description 2
- 150000004665 fatty acids Chemical class 0.000 claims description 2
- 125000005456 glyceride group Chemical group 0.000 claims description 2
- 235000011187 glycerol Nutrition 0.000 claims description 2
- 229940087068 glyceryl caprylate Drugs 0.000 claims description 2
- 235000019388 lanolin Nutrition 0.000 claims description 2
- 229940039717 lanolin Drugs 0.000 claims description 2
- 229920001223 polyethylene glycol Polymers 0.000 claims description 2
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 claims description 2
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 claims description 2
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 claims description 2
- 229920000136 polysorbate Polymers 0.000 claims description 2
- 229920000053 polysorbate 80 Polymers 0.000 claims description 2
- GHBFNMLVSPCDGN-UHFFFAOYSA-N rac-1-monooctanoylglycerol Chemical compound CCCCCCCC(=O)OCC(O)CO GHBFNMLVSPCDGN-UHFFFAOYSA-N 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 claims description 2
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 claims description 2
- 239000000600 sorbitol Substances 0.000 claims description 2
- 229960002920 sorbitol Drugs 0.000 claims description 2
- 238000009472 formulation Methods 0.000 claims 2
- 239000002585 base Substances 0.000 claims 1
- 238000005886 esterification reaction Methods 0.000 claims 1
- 235000013311 vegetables Nutrition 0.000 claims 1
- 230000007794 irritation Effects 0.000 abstract description 16
- 235000019505 tobacco product Nutrition 0.000 abstract description 14
- 239000003571 electronic cigarette Substances 0.000 abstract description 3
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract description 2
- 206010013781 dry mouth Diseases 0.000 abstract 1
- 239000000779 smoke Substances 0.000 description 15
- 235000019504 cigarettes Nutrition 0.000 description 11
- 235000009508 confectionery Nutrition 0.000 description 11
- 238000011156 evaluation Methods 0.000 description 10
- 230000001953 sensory effect Effects 0.000 description 8
- WKOLLVMJNQIZCI-UHFFFAOYSA-N vanillic acid Chemical compound COC1=CC(C(O)=O)=CC=C1O WKOLLVMJNQIZCI-UHFFFAOYSA-N 0.000 description 8
- 238000001704 evaporation Methods 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 239000000243 solution Substances 0.000 description 6
- 235000013399 edible fruits Nutrition 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 239000002304 perfume Substances 0.000 description 5
- 206010013911 Dysgeusia Diseases 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 244000290333 Vanilla fragrans Species 0.000 description 3
- 235000009499 Vanilla fragrans Nutrition 0.000 description 3
- 235000012036 Vanilla tahitensis Nutrition 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 2
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 2
- 240000007472 Leucaena leucocephala Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 208000005946 Xerostomia Diseases 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229960000956 coumarin Drugs 0.000 description 2
- 235000001671 coumarin Nutrition 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 210000000214 mouth Anatomy 0.000 description 2
- 229930014626 natural product Natural products 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000013589 supplement Substances 0.000 description 2
- 235000019605 sweet taste sensations Nutrition 0.000 description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 description 1
- 239000005792 Geraniol Substances 0.000 description 1
- YKVWPZJHENXDAJ-VOTSOKGWSA-N Megastigmatrienone Chemical compound CC1=CC(=O)CC(C)(C)C1\C=C\C=C YKVWPZJHENXDAJ-VOTSOKGWSA-N 0.000 description 1
- 241000745768 Pluchea carolinensis Species 0.000 description 1
- 244000269722 Thea sinensis Species 0.000 description 1
- 238000000889 atomisation Methods 0.000 description 1
- 239000012496 blank sample Substances 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000004030 farnesyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 235000020765 fenugreek extract Nutrition 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 229940113087 geraniol Drugs 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Landscapes
- Manufacture Of Tobacco Products (AREA)
- Fats And Perfumes (AREA)
Abstract
The invention discloses a farnesyl vanillate which has the following structure:
Description
Technical Field
The invention relates to the technical field of tobacco product production and processing, in particular to farnesyl vanillate, a preparation method thereof and application thereof in the tobacco industry. The flavoring agent can be applied to the flavoring links of tobacco products and electronic cigarette production and manufacture, and is used for reducing the irritation of the tobacco products, enriching and coordinating the tobacco fragrance.
Background
Because tobacco leaves per se contain a great amount of components, the tobacco products inevitably bring bad experiences of irritation, miscellaneous gases and the like to the oral cavity during combustion and suction, and the fields of tobacco product production and processing and manufacturing are used for reducing the irritation of tobacco, enriching and harmonizing the natural spice of the tobacco fragrance have high demands. Natural extraction of perfume such as vanilla extract can supplement tobacco fragrance and alleviate odor absorption; the coffee extract can be used for baking tobacco aroma and improving odor absorption; the black fenugreek extract can supplement tobacco fragrance and alleviate odor absorption. Synthetic flavors such as megastigmatrienone can enhance sweet taste and improve flavor absorption. Coumarin is a common flavoring substance for tobacco. Coumarin is prohibited from being used in tobacco because of damage to the liver, kidneys, etc. The novel spice which is natural and healthy in taste, pure and rich in fragrance and modified based on natural products is used for producing, processing and manufacturing tobacco products, and is always a target for the life and struggle of the technicians in the technical field of tobacco product manufacturing.
Disclosure of Invention
The invention is based on the synthetic modification transformation of natural products of vanillic acid and farnesol, and a novel natural perfume compound is obtained, belongs to a novel compound, is not reported in any synthetic preparation and perfume application, and is more suitable for being used in advance in the industry of tobacco.
The specific technical scheme of the invention is as follows:
an farnesyl vanillate having the structure:
wherein R represents a H, C C10 alkyl group, preferably a C1C 6 alkyl group, such as methyl, ethyl, n-propyl, isopropyl.
In one specific example of the present invention,
the chemical name is: (2E, 6E) -3,7, 11-trimethyldodecyl-2, 6, 10-trien-1-yl 4-hydroxy-3-methoxybenzoate (VF).
The invention also aims to provide a preparation method of the farnesyl vanillate, which comprises the following steps:
(1) Reacting a compound of formula 1 with chloromethyl methyl ether in the presence of alkali to obtain a compound of formula 3,
(2) Esterifying the compound of formula 3 with farnesol to obtain a compound of formula 4,
(3) The compound of formula 4 reacts under the condition of trifluoroacetic acid to obtain the farnesyl vanillic acid.
Wherein R is 1 R when H is represented 2 Is CH 3 OCH 2 ,R 1 R represents C1-C10 alkyl 2 ＝R 1 。
Preferably, the solvent in the step (1) is tetrahydrofuran, the alkali is triethylamine, and potassium iodide is used as a catalyst to react for 12 hours at room temperature; the solvent of the step (2) is methylene dichloride, and 1-ethyl- (3-dimethylaminopropyl) carbodiimide hydrochloride and 4-dimethylaminopyridine are used as catalysts to react for 12 hours at room temperature; the solvent in the step (3) is dichloromethane, and the reaction is carried out for 0.5h at room temperature. The room temperature of the invention is 20-30 ℃.
One specific example is as follows:
(1) The compound of formula 1 is dissolved in tetrahydrofuran, chloromethyl methyl ether (compound of formula 2), triethylamine and potassium iodide are added, and the mixture is reacted for 12 hours at room temperature. Evaporating and concentrating the solvent after the reaction is completed, extracting the solvent by using saturated saline and dichloromethane, drying an organic layer by using anhydrous sodium sulfate, and evaporating and concentrating the organic layer to obtain a compound shown in a formula 3;
(2) The compound of formula 3 was dissolved in dichloromethane, farnesol, EDCI and DMAP were added and reacted at room temperature for 12 hours. Evaporating and concentrating the solvent after the reaction is completed, extracting with saturated saline water and dichloromethane, drying an organic layer by anhydrous sodium sulfate, evaporating and concentrating to obtain a solid, namely a crude product, and purifying by column chromatography to obtain a compound shown in a formula 4;
(3) Dissolving intermediate 4 in dichloromethane, adding trifluoroacetic acid, reacting at room temperature for 0.5h, cooling the reaction liquid to room temperature, decompressing and evaporating the solvent, washing the obtained solid with saturated sodium bicarbonate solution, filtering to obtain a crude product, and purifying by column chromatography to obtain the compound.
The invention also provides application of the farnesyl vanillic acid (serving as a flavoring substance) in the tobacco industry, which can reduce the irritation, burnt smell and mouth dryness of a pure tobacco product, improve the fragrant and sweet taste of the smoke, and enhance the flavoring, so that the original smoke is rich and coordinated in fragrance, has faint scent of fruit tree, pure fragrance and natural taste, and the smoke is transparent and sweet. The farnesyl vanillic acid can be prepared into a spice preparation, and the mass percentage of the spice preparation in tobacco is 0.001% -1%.
The invention also provides a spice preparation of the farnesyl vanillic acid for tobacco, which comprises the farnesyl vanillic acid. Further, the composition also comprises an emulsifying agent and a dispersing agent. The emulsifier comprises one or more of sorbitol, glyceryl monostearate, glyceryl caprylate, partial glyceride mixture of saturated plant fatty acid, tween 20, tween 40, tween 60, tween 80, polyethylene glycol, sodium carboxymethyl cellulose, beeswax and lanolin, and the dispersing agent is one or more of water, propylene glycol, 0-80% ethanol and glycerol.
The weight percentage of the emulsifier in the spice preparation is 0.001-5%, the weight percentage of the dispersant is 10-90%, and the weight percentage of the farnesyl vanillic acid is 5-89.999%.
The invention has the following advantages:
1. the spice preparation prepared from the farnesyl vanillate disclosed by the invention is clear and transparent in appearance state, good in fluidity, and capable of meeting the use requirements of tobacco industry and electronic cigarette spices, has faint fruit tree fragrance, prominent sweet feel and small fragrance irritation, does not have unnatural feel and irritation of the traditional spice, and has sensory quality far superior to that of the common natural extract in the market.
2. After the spice preparation of the farnesyl vanilla ester is applied to tobacco products, the irritation, burnt taste and mouth dryness of the pure tobacco products can be reduced, the fragrant, mellow and sweet performance of the smoke taste is improved, the original smoke fragrance is rich and coordinated, the faint fruit tree fragrance is realized, the fragrance is pure, the taste is natural, the smoke is thoroughly and back sweet, and the quality and sensory smoking experience of the tobacco products are greatly improved.
Detailed Description
The invention will be further illustrated with reference to specific examples. It is to be understood that these examples are illustrative of the present invention and are not intended to limit the scope of the present invention. The experimental procedures, which do not address the specific conditions in the examples below, are generally carried out under conventional conditions or under conditions recommended by the manufacturer.
Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art. In addition, any methods and materials similar or equivalent to those described herein can be used in the methods of the present invention. The preferred methods and materials described herein are presented for illustrative purposes only.
Example 1: preparation of (2E, 6E) -3,7, 11-trimethyldodecyl-2, 6, 10-trien-1-yl 4-hydroxy-3-methoxybenzoate (VF)
The compound of formula 1 (10 mmol,1 eq) was dissolved in 10mL tetrahydrofuran, and the compound of formula 2 (12 mmol,1.2 eq), 500. Mu.L triethylamine and (1 mmol,0.1 eq) potassium iodide were added and reacted at room temperature for 12h. After completion of the reaction, the solvent was concentrated by evaporation, extracted with saturated brine and DCM, and the organic layer was dried over anhydrous sodium sulfate and concentrated by evaporation to give the compound of formula 3 in 89% yield. MS (ESI) m/z 213[ M+H ]] + 。
The compound of formula 3 (10 mmol,1 eq) was dissolved in 10mL DCM, farnesol (12 mmol,1.2 eq), EDCI (12 mmol,1.2 eq) and DMAP (5 mmol,0.5 eq) were added and reacted for 12h at room temperature. After completion of the reaction, the solvent was concentrated, extracted with saturated brine and DCM, the organic layer was a DCM solution of the compound of formula 4, dried over anhydrous sodium sulfate, 200 μl of trifluoroacetic acid was added, reacted at room temperature for 0.5h, and then washed and concentrated with saturated sodium bicarbonate solution, and the target compound VF was purified by column chromatography in 78% yield. MS (ESI) m-z:373[M+H] + .1H NMR(400MHz,DMSO-d 6 )δ9.56(s,1H),7.62(dd,J＝9.1,1.9Hz,1H),7.49(d,J＝1.8Hz,1H),7.15(d,J＝9.1Hz,1H),5.41–5.34(m,1H),5.15–5.07(m,1H),5.11–5.05(m,1H),4.78–4.72(m,2H),3.84(s,3H),2.18–2.04(m,6H),1.97–1.89(m,2H),1.70–1.66(m,3H),1.66–1.58(m,9H).
Example 2: preparation of farnesyl vanillic acid spice preparation
Adding the purified product VF (purity > 99%) prepared in the example 1 into a mixing tank, adding an emulsifying agent (composed of glyceryl monostearate and glyceryl octoate in a weight ratio of 1:1:0.5), stirring and mixing for 0.5h under a certain temperature condition, cooling the feed liquid, conveying the feed liquid to a high-pressure homogenizer, and uniformly mixing the feed liquid with 80% ethanol solution to obtain the spice preparation of the farnesyl vanillate.
The addition amount of the farnesyl vanillic acid is 45-49.999% of the mass of the spice preparation. The addition amount of the emulsifier is 0.001-5% of the mass of the spice preparation; the mixing condition is that the temperature is 60-80 ℃, and the stirring speed is 200-350 rpm; the high-pressure homogenizing condition is that the feeding temperature is 45 ℃, and the homogenizing pressure is 10-20 Mpa. The 80% ethanol solution is 50% of the perfume preparation by mass.
Example 3: evaluation of appearance State, solubility, smell aroma, sensory evaluation of the Vanilla Acacia ester spice preparation of the invention
Using the farnesyl oxalate perfume preparation of example 2 as an example, the appearance state, smell and sensory evaluation were carried out, and the results were as follows:
appearance state: clear, transparent and non-layering after standing.
Smell and aroma sense: the light fruit tree has faint scent, sweet scent, small fragrance irritation, strong volatility and large fragrance irritation, and the fragrance is different from natural spice vanillic acid, geraniol, farnesol and the like.
Sensory evaluation test of tobacco smearing: the tobacco has the advantages of reduced irritation, outstanding sweet feeling, soft and mellow taste, good harmony, clear characteristics, sweet and fragrant smoke, natural fragrance and the like.
Uniformly spraying the tobacco spice preparation into tobacco shreds in an atomization mode, wherein the tobacco spice preparation accounts for 0.1% of the mass of the tobacco shreds; the tobacco shreds obtained in this way are balanced for 48 hours in a constant-temperature (22 ℃ +/-2 ℃) constant-humidity (RH 60% +/-5%) box, and cigarettes are made to correspondingly make parallel-like cigarette products 1 and 2 respectively. The sensory quality and stability of the tea are respectively identified, and main evaluation indexes are indexes such as aroma characteristics, harmony, aroma quality, sweet feeling, aftertaste, miscellaneous gases and irritation, and each index is fully divided into 10 minutes.
A higher aroma characteristic score indicates a more pronounced sensory change in aroma imparted to the tobacco product.
The higher the coordination and the fragrance quality score, the better the coordination between the fragrance and the smoke, the purer and fresh fragrance quality and less unpleasant smell.
The higher the sweet score, the lower the dryness of the added smoke, and the better the comfort experience.
The higher the irritation fraction is, the lower the irritation of the smoke is, the taste is soft, the low score is used for representing that the smoke is choked, and the irritation to the throat is large;
the higher the impurity gas score is, the purer the added smoke is, the lower the score is, the turbidity of the smoke is indicated, and the flavor is unclear.
The higher the aftertaste score, the longer the duration of the smoke scent in the mouth, and the increased aftertaste.
The suction evaluation is performed by a suction evaluation group consisting of 7 special suction evaluation experts of cigarettes, and the average suction evaluation results are shown in table 1:
table 1 average score of sensory evaluation results
| Project | Fragrance characteristics (10) | Coordination (10) | Fragrance quality (10) | Sweet feeling (10) | Aftertaste (10) | Miscellaneous gas (10) | Irritation (10) |
| Blank cigarette sample | 2 | 2 | 2 | 1 | 1 | 1 | 0 |
| Cigarette product 1 | 7 | 8 | 8 | 8 | 6 | 7 | 5 |
| Cigarette product 2 | 8 | 8 | 7 | 8 | 5 | 6 | 6 |
As can be seen by comparing blank samples, the spice preparation of the tobacco farnesyl oxalate disclosed by the invention is added into a formula of a cigarette leaf set, so that the aroma quality of cigarettes can be effectively improved, the sweet feeling is prominent, the obtained cigarettes have coordinated smoke, light fruit and wood fragrance, the aroma quality and the aroma quantity are obviously increased, the sweet aroma of the cigarettes can be increased, the taste is improved, and the quality of the cigarettes is improved.
The above description is merely a preferred embodiment of the present invention, the protection scope of the present invention is not limited to the above embodiments, and all technical solutions belonging to the concept of the present invention belong to the protection scope of the present invention, and it should be noted that, for those skilled in the art, the number, proportion and concentration of the raw materials and auxiliary materials should be regarded as the protection scope of the present invention without departing from the principle of the present invention.
Claims (9)
1. An farnesyl vanillate characterized by the following structure:
2. a method for preparing farnesyl vanillic acid according to claim 1, comprising the following steps:
(1) Reacting a compound of formula 1 with chloromethyl methyl ether in the presence of alkali to obtain a compound of formula 3,
(2) Using 1-ethyl- (3-dimethylaminopropyl) carbodiimide hydrochloride and 4-dimethylaminopyridine as catalysts, carrying out esterification reaction on the compound shown in the formula 3 and farnesol to obtain a compound shown in the formula 4,
(3) Reacting the compound of formula 4 under trifluoroacetic acid to obtain farnesyl vanillic acid according to claim 1,
3. the preparation method according to claim 2, wherein the solvent in the step (1) is tetrahydrofuran, the base is triethylamine, and potassium iodide is used as a catalyst, and the reaction is carried out for 12 hours at room temperature; the solvent in the step (2) is methylene dichloride, and the reaction is carried out for 12 hours at room temperature; the solvent in the step (3) is dichloromethane, and the reaction is carried out for 0.5h at room temperature.
4. Use of farnesyl vanillic acid according to claim 1 in the tobacco industry.
5. The use according to claim 4, characterized in that farnesyl vanillic acid is made into a flavour preparation, the mass percentage of the flavour preparation in the tobacco being between 0.001% and 1%.
6. A flavor formulation of farnesyl vanillic acid for tobacco, characterized by comprising farnesyl vanillic acid according to claim 1.
7. The fragrance formulation of claim 6 further comprising an emulsifier and a dispersant.
8. The spice preparation according to claim 7, wherein the emulsifier comprises one or more selected from the group consisting of sorbitol, glyceryl monostearate, glyceryl caprylate, partial glyceride mixture of saturated vegetable fatty acids, tween 20, tween 40, tween 60, tween 80, polyethylene glycol, sodium carboxymethyl cellulose, beeswax and lanolin, and the dispersing agent is one or more selected from the group consisting of water, propylene glycol, 0-80% ethanol and glycerin.
9. The spice preparation according to claim 8, wherein the mass percentage of the emulsifier in the spice preparation is 0.001% -5%, the mass percentage of the dispersing agent is 10% -90%, and the mass percentage of the farnesyl vanillic acid is 5% -89.999%.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111590480.8A CN114315586B (en) | 2021-12-23 | 2021-12-23 | Acacia vanillate and preparation method and application thereof in tobacco industry |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111590480.8A CN114315586B (en) | 2021-12-23 | 2021-12-23 | Acacia vanillate and preparation method and application thereof in tobacco industry |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN114315586A CN114315586A (en) | 2022-04-12 |
| CN114315586B true CN114315586B (en) | 2023-12-08 |
Family
ID=81054055
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202111590480.8A Active CN114315586B (en) | 2021-12-23 | 2021-12-23 | Acacia vanillate and preparation method and application thereof in tobacco industry |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN114315586B (en) |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008090440A1 (en) * | 2007-01-22 | 2008-07-31 | Carlo Ghisalberti | Lipid-based gynaecologic suppository |
| CN101318905A (en) * | 2008-07-15 | 2008-12-10 | 中国林业科学研究院林产化学工业研究所 | Method for synthesizing gallic acid terpene alcohol ester with auxiliary supersonic wave |
| CN104530152A (en) * | 2015-01-15 | 2015-04-22 | 佛山市赛维斯医药科技有限公司 | Compound containing acrylonitrile base and trifluoro methoxyphenyl O-galactoside structure and application |
| CN109864331A (en) * | 2019-04-11 | 2019-06-11 | 滁州卷烟材料厂 | A kind of cigarette flavors additive and preparation method thereof |
| CN111454288A (en) * | 2019-01-22 | 2020-07-28 | 上海交通大学医学院附属仁济医院 | Phosphoramidite containing phenolic hydroxyl, preparation method and application thereof |
-
2021
- 2021-12-23 CN CN202111590480.8A patent/CN114315586B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008090440A1 (en) * | 2007-01-22 | 2008-07-31 | Carlo Ghisalberti | Lipid-based gynaecologic suppository |
| CN101318905A (en) * | 2008-07-15 | 2008-12-10 | 中国林业科学研究院林产化学工业研究所 | Method for synthesizing gallic acid terpene alcohol ester with auxiliary supersonic wave |
| CN104530152A (en) * | 2015-01-15 | 2015-04-22 | 佛山市赛维斯医药科技有限公司 | Compound containing acrylonitrile base and trifluoro methoxyphenyl O-galactoside structure and application |
| CN111454288A (en) * | 2019-01-22 | 2020-07-28 | 上海交通大学医学院附属仁济医院 | Phosphoramidite containing phenolic hydroxyl, preparation method and application thereof |
| CN109864331A (en) * | 2019-04-11 | 2019-06-11 | 滁州卷烟材料厂 | A kind of cigarette flavors additive and preparation method thereof |
Non-Patent Citations (2)
| Title |
|---|
| Inhibition of vertebrate squalene epoxidase by isoprenyl gallates and phenylalkyl gallates;Abe, Ikuro等;Bioorganic & Medicinal Chemistry Letters;第10卷(第22期);2525-2528 * |
| Tea Polyphenols Inhibit Acetyl-CoA:1-Alkyl-sn-Glycero-3-Phosphocholine Acetyltransferase (a Key Enzyme in Platelet-Activating Factor Biosynthesis) and Platelet-Activating Factor-Induced Platelet Aggregation;Sugatani, Junko等;International Archives of Allergy and Immunology;第134卷(第1期);17-28 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN114315586A (en) | 2022-04-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN108504454B (en) | Preparation method of improved cigarette tailing spice and application of improved cigarette tailing spice in cigarettes | |
| CN105542959A (en) | Method for preparing electronic cigarette liquid flavor | |
| US4617419A (en) | Process for preparing natural benzaldehyde and acetaldehyde, natural benzaldehyde and acetaldehyde compositions, products produced thereby and organoleptic utilities therefor | |
| CN111406970A (en) | Sweet-burning base for cigarettes | |
| CN114315586B (en) | Acacia vanillate and preparation method and application thereof in tobacco industry | |
| CN114315587B (en) | Linalyl vanillate, preparation method thereof and application thereof in tobacco industry | |
| WO2010003299A1 (en) | A flavor enhancer and preparation method thereof | |
| US4963193A (en) | Oxo-ionyl esters useful as tobacco flavorants and tobacco products containing same | |
| CN114516797B (en) | Methyl cyclopentenolone menthol carbonate spice and synthetic method and application thereof | |
| CN113277947B (en) | 3- (2-hydroxyphenyl) propionic acid-2-hydroxypropyl ester as cigarette monomer spice and synthesis method and application thereof | |
| CN112759585B (en) | Compound with tomato aroma, preparation method thereof and daily essence | |
| JP7148743B2 (en) | (Z) type solanone, method of preparation and use thereof | |
| US6194019B1 (en) | Delayed release flavorant compositions | |
| CN110862365B (en) | Tobacco sweetener, preparation method and application | |
| CN113331460A (en) | Maillard intermediate and application thereof in tobacco flavoring | |
| US4683342A (en) | Process for preparing natural benzaldehyde and acetaldehyde, natural benzaldehyde and acetaldehyde compositions, products produced thereby and organoleptic utilities therefor | |
| CN112120271A (en) | Preparation of malt tobacco flavor and application of malt tobacco flavor in tobacco | |
| CN114380693B (en) | Methyl cyclopentenol ketogeraniol carbonate spice and synthetic method and application thereof | |
| US4727197A (en) | Process for preparing natural benzaldehyde and acetaldehyde natural benzaldehyde and acetaldehyde compositions, products produced thereby and organoleptic utilities therefor | |
| CN116463171B (en) | Essence for enhancing cigarette aroma and preparation method and application thereof | |
| CN118370402A (en) | Low-tar cigarette expansion tobacco shred essence and use method thereof | |
| US4766002A (en) | Flavoring with α-campholenic alcohol | |
| US3805804A (en) | Method of improved tobacco product containing phenyl-pentenals | |
| US4726384A (en) | Process for preparing natural benzaldehyde and acetaldehyde, natural benzaldehyde and acetaldehyde compositions, products produced thereby and organcleptic utilities therefor | |
| CN118266621A (en) | Litchi flavor essence, litchi flavor electronic cigarette tobacco tar and preparation method thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |