CN101125828A - Synthesis method for alpha-carbonylenamine derivative cooling agent (3-MPC) and application thereof - Google Patents

Synthesis method for alpha-carbonylenamine derivative cooling agent (3-MPC) and application thereof Download PDF

Info

Publication number
CN101125828A
CN101125828A CN 200710066050 CN200710066050A CN101125828A CN 101125828 A CN101125828 A CN 101125828A CN 200710066050 CN200710066050 CN 200710066050 CN 200710066050 A CN200710066050 A CN 200710066050A CN 101125828 A CN101125828 A CN 101125828A
Authority
CN
Grant status
Application
Patent type
Prior art keywords
solution
solvent
cooling agents
characterized
mpc
Prior art date
Application number
CN 200710066050
Other languages
Chinese (zh)
Inventor
军 倪
昆 古
成会玲
杨伟祖
冰 谢
陈永宽
Original Assignee
云南瑞升烟草技术(集团)有限公司
Priority date (The priority date 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 date listed.)
Filing date
Publication date

Links

Abstract

The invention relates to a synthesis method of Alpha-keto-based enamine derivative cooling agent (3-MPC), which is characterized in that methyl-cyclopentene alcohol ketone and pyrrolidine are taken as raw materials and mixed by mass ratio of 1:1.8-2.0, and catalyst p-toluene sulphonic acid is added by 0.2-0.5 percent of the mass ratio of cyclopentene alcohol ketone and pyrrolidine, refluxed through solvent, and water is added when the solvent is steamed, pH value is regulated by NaOH solution to be approximately equal to 9, then the reaction solution is extracted by ether, after extraction, the organic layer is combined and washed by Na2CO3 solution, then the solvent is dried by anhydrous Na2SO4 and steamed, thereby acquiring brown-yellow oily liquid which is processed by column chromatography with alkali alumina, and light yellow oily liquid Alpha-Keto-based enamine derivative cooling agent product is acquired. The non-menthol cooling agent 3-MPC synthesized by the invention is implemented by certain concentration into cut tobacco of cigarettes, toothpaste and chewing gum and has the effects of even cool taste which lasts for a long time and prominent comfortable feeling, etc.

Description

a-酮基烯胺衍生物凉味剂(3-MPC)的合成方法及其应用技术领域本发明涉及日用化工产品技术领域,具体地说是一种01-酮基烯胺衍生物[3-甲基-2-(1-吡咯垸基)-2-环戊烯-l-酮(简称3-MPC)]凉味剂的合成方法及其应用。 a- keto enamine derivatives cooling agent (3-MPC) and synthesis method TECHNICAL FIELD The present invention relates to a technical field household chemical products, in particular to a 01- keto enamine derivative [3 - methyl-2- (1-pyrrolidinyl embankment yl) -2-cyclopenten-one -l- (referred to as 3-MPC)] synthesis and use of cooling agents. 背景技术凉味剂在食品工业、日化工业、烟草工业和医药工业等领域是一类重要的有机原料, 己成为人们日常生活中必不可少的添加剂,特别是口香糖、巻烟、食品和护肤用品等更是离不开凉味剂。 BACKGROUND cooling agents are an important class of organic raw materials in the food industry, the chemical industry, the tobacco industry and the pharmaceutical industry and other fields, it has become an everyday essential additives, in particular chewing gum, Volume smoke, food and skin care supplies more indispensable cooling agents. 而且,从目前国内外的食品工业、化妆品工业和医药工业来看,市场对凉味剂的需求在逐年增加。 Moreover, from the current domestic and international food industry, cosmetics industry and pharmaceutical industry, the market demand for cooling agents is increasing year by year. 传统上,使用(-)薄荷醇作为凉味剂,但薄荷醇的挥发度较高,凉感的持续时间较短, 加之它对人眼睛的刺激性较强。 Traditionally, the use of (-) menthol as cooling agents, but higher volatility of menthol, the duration of a short cool feeling, combined with a strong eye irritation its people. 因此,开发新型非薄荷醇凉味剂产品,满足人们寻求更为长效的凉味剂产品,达到凉感持续时间长、感觉较为均匀的凉味产品具有十分重要的意义。 Therefore, the development of new non-menthol cooling agents products to meet more people to seek long-term cooling agents products in order to cool feeling lasted for a long time, I feel even more cool taste of the product is of great importance. 发明内容本发明的目的是提供一种新型的a-酮基烯胺衍生物类(非薄荷醇)凉味剂(即3-MPC ) 的合成方法,以及在口香糖、牙膏、巻烟烟丝中有应用。 SUMMARY OF THE INVENTION An object of the present invention is to provide a novel a- keto enamine derivatives (non-menthol) cooling agents (i.e., 3-MPC) in the synthetic methods, as well as chewing gum, toothpaste, Volume in tobacco application. 本发明是在于以甲基环戊烯醇酮(MCP)和四氢吡咯烷为原料,以对甲苯磺酸为催化剂,在溶剂回流状态下一步反应,制成a-酮基烯胺衍生物G-甲基-2-(l-吡咯烷基)-2-环戊烯-l-酮(3-MPC)。 The present invention is characterized methyl cyclopentenolone (MCP) and tetrahydro-pyrrolidine as starting material, p - toluenesulfonic acid as catalyst, in a solvent in the next reaction reflux prepare a- keto enamine derivative G - methyl -2- (L-pyrrolidinyl) -2-cyclopenten-one -l- (3-MPC). 本发明的3-甲基-2-(l-吡咯烷基)-2-环戊烯-l-酮(3-MPC)的合成方法是:以甲基环戊烯醇酮(MCP)和四氢吡咯烷为原料(反应物料),按质量比为l : 1.8 — 2.0混合,加入反应物料总量0.2—0.5%的催化剂对甲苯磺酸,用溶剂回流,停止反应并蒸去溶剂,加入反应物料总量3倍的水,再用NaOH溶液调节pH"9,然后用乙醚萃取该反应液,萃取完毕之后,合并有机层,有机层再用Na2C03溶液洗涤,再用无水Na2S04干燥,用旋转蒸发仪蒸去溶剂,得到棕黄色油状液体,用碱性氧化铝进行柱层析洗脱,得到淡黄色的油状液体a-酮基烯胺衍生物凉味剂产品。合成反应所采用的溶剂是甲醇或乙醇,用量为反应物料总量的8倍。回流反应时间为7-ll小时,最好为9小时。在柱层析过程中的洗脱液为石油醚:乙酸乙酯=60 : 1。 Methyl invention -2- (L-pyrrolidinyl) -2-cyclopenten-one -l- (3-MPC) are: methyl cyclopentenolone (MCP) and tetrakis hydrogen pyrrolidine as starting material (the reaction mass), a mass ratio of l: 1.8 - 2.0 were mixed, 0.2-0.5% of the total reaction mass of the catalyst p-toluenesulfonic acid, refluxed with a solvent, the reaction was stopped and the solvent was distilled off, the reaction was added 3 times the total mass of water, with NaOH solution to adjust pH "9, the reaction solution was then extracted with ether, after completion of the extraction, the organic layers were combined, and the organic layer was washed with Na2C03 solution, dried over anhydrous Na2S04 and dried using a rotary evaporator and the solvent was evaporated to give a brown oily liquid chromatography column was eluted with basic alumina to give a pale yellow oily liquid a- keto enamine derivatives cooling agents product synthesis reaction solvent used is methanol or ethanol, in an amount of 8 times the total mass of the reaction the reaction time was 7-ll hours, preferably 9 hours eluent for the chromatography column with petroleum ether: ethyl acetate = 60: 1 .

甲基环戊烯醇酮和四氢吡咯垸的质量比为i : 1.2—1.4,最好为i : 1.9。 Methyl cyclopentenolone pyrrolidine embankment and mass ratio i: 1.2-1.4, preferably i: 1.9. 本发明的3-甲基-2-(l-吡咯垸基)-2-环戊烯-l-酮(3-MPC)与醇类溶剂配制成溶液后,直接添加到口香糖、化妆品、牙膏、巻烟烟丝中制成成品。 After the present invention is 3-methyl -2- (L-pyrrol embankment yl) -2-cyclopenten-one -l- (3-MPC) and the solution was formulated as an alcoholic solvent, added directly to the chewing gum, cosmetics, toothpaste, Volume finished products in tobacco. 本发明的非薄荷醇凉味剂3-MPC在巻烟烟丝中的应用是:将3-MPC与醇类溶剂配成溶液后,按0.001-1% (烟草重量百分比)后施加到巻烟烟丝上,施加方法为喷洒在叶组烟丝上在空气中晾干即可。 Application of a non-menthol cooling agent 3-MPC of the present invention is in tobacco Volume: after 3-MPC prepare a solution with an alcoholic solvent, according 0.001 to 1% (by weight tobacco) is applied to the tobacco by Volume , the application method is sprayed onto the group of tobacco leaves to dry in air. 本发明的非薄荷醇凉味剂3-MPC在其它方面的应用是:将3-MPC与醇类溶剂配成溶液后,按0.001-1% (烟草重量百分比)施加到牙膏、口香糖配料中,混合均匀制成即可。 Application of a non-menthol cooling agents of the present invention 3-MPC is in other respects: after 3-MPC prepare a solution with an alcoholic solvent, according 0.001 to 1% (by weight tobacco) is applied to the toothpaste, chewing gum ingredients, It can be made uniform mixing. 所述的醇类溶剂为乙醇或丙二醇或甘油。 The alcoholic solvent is ethanol or propylene glycol or glycerol. 采用本发明所合成的非薄荷醇凉味剂3-MPC,并以一定的浓度分别施加在巻烟烟丝、 牙膏、口香糖中,具有凉味均匀,持续时间长,舒适感明显等功效。 Non-menthol cooling agents synthesized 3-MPC present invention, and are applied at a certain concentration in Volume in tobacco, toothpaste, chewing gum, having a cool taste uniform, long duration, and other effects significant comfort. 具体实施方式本发明是通过催化合成法来合成非薄荷醇凉味剂3-MPC。 DETAILED DESCRIPTION The present invention is synthesized non-menthol cooling agents by catalytic synthesis 3-MPC. 实施例l:取甲基环戊烯醇酮(MCP) 33.6g、四氢吡咯烷60.5g、对甲苯磺酸0.19g,(按反应物料8倍量溶剂)甲醇754g,将甲基环戊烯醇酮与四氢吡咯烷混合,加入催化剂对甲苯磺酸,快速升温至回流状态,回流时间是7小时,停止反应并蒸去溶剂,加入283g水(按反应物料3 倍量),再用30。 Example l: Take methyl cyclopentenolone (MCP) 33.6g, tetrahydro-pyrrolidine 60.5g, p-toluenesulfonic acid 0.19g, (8 times the amount of the reaction mass by solvent) methanol 754g, methyl cyclopentene alcohol was mixed with tetrahydro-pyrrolidine-one, p-toluenesulfonic acid catalyst was added quickly warmed to reflux, reflux time is 7 hours, the reaction was stopped and the solvent was evaporated, water was added 283g (the amount of the reaction mass by 3 times), then 30 . /。 /. 的NaOH溶液调节pH"9,然后用乙醚萃取该反应液,萃取完毕之后,合并有机层,有机层再用0.5mol/LNa2CO3溶液洗涤,再用无水Na2S04干燥,用旋转蒸发仪蒸去溶剂,得到棕黄色油状液体,用400目的碱性氧化铝进行柱层析,洗脱液为石油醚:乙酸乙酯=60: 1,得到淡黄色的油状液体为a-酮基烯胺衍生物类凉味剂(3-MPC)产品。产物经红外光谱、质谱及核磁共振谱加以表征:3-MPC为淡黄色的油状液体;IR, v,(cm懇1》2963.9, 2923.6, 2867.2(-CH2-、 -CH3), 1694.1(C=0), 1616.2(OC), 1488.8, 1458.7, 1448.8, 1409.6, 1395.3, 1352.5, 1328.6(-CH2-,-CH3); MS(EI, 70ev): 165(M+), 136, 122, 108, 95, 70。 iHNMR谱解析: NaOH solution to adjust the pH "9, the reaction solution was then extracted with ether, after completion of the extraction, the organic layers were combined, and the organic layer was washed with 0.5mol / LNa2CO3 solution, dried over anhydrous Na2S04 dried, the solvent was distilled off on a rotary evaporator, to give brown oily liquid, which was chromatographed on basic alumina 400 mesh, eluent petroleum ether: ethyl acetate = 60: 1, to give a pale yellow oily liquid is a- keto enamine derivatives cool . flavor (3-MPC) product the product to be characterized by IR, MS and NMR Characterization: 3-MPC as a pale yellow oily liquid; IR, v, (cm Ken 1 "2963.9, 2923.6, 2867.2 (-CH2- , -CH3), 1694.1 (C = 0), 1616.2 (OC), 1488.8, 1458.7, 1448.8, 1409.6, 1395.3, 1352.5, 1328.6 (-CH2 -, - CH3); MS (EI, 70ev): 165 (M +) , 136, 122, 108, 95, 70. iHNMR Elucidation:

CNMR谱解析:17.5 29.7实施例2:取按甲基环戊烯醇酮(MCP) 33.6g、四氢吡咯垸63.8g、对甲苯磺酸0.28g,甲醇780g, 将甲基环戊烯醇酮与四氢吡咯垸混合,加入催化剂对甲苯磺酸,快速升温至回流状态,回流时间是9小时,停止反应并蒸去溶剂,加入293g水,再用30%的NaOH溶液调节pH"9, 然后用乙醚萃取该反应液,萃取完毕之后,合并有机层,有机层再用0.5mol/LNa2CO3溶液洗涤,再用无水Na2S04干燥,用旋转蒸发仪蒸去溶剂,得到棕黄色油状液体,用400目的碱性氧化铝进行柱层析,洗脱液为石油醚:乙酸乙酯=60 : 1,得到淡黄色的油状液体为3-MPC产品。产物经红外光谱、质谱及核磁共振谱加以表征与实施例l相同。 CNMR spectral analysis: 17.5 29.7 Example 2: taking by methyl cyclopentenolone (MCP) 33.6g, pyrrolidine embankment 63.8g, p-toluenesulfonic acid 0.28g, methanol 780g, methyl cyclopentenolone mixed with pyrrolidine embankment, p-toluenesulfonic acid catalyst was added quickly warmed to reflux, reflux time is 9 hours, the solvent was distilled off and the reaction was stopped, 293g water was added, then 30% NaOH solution to adjust pH "9, and after the reaction solution was extracted with diethyl ether, is completed, the organic layers were combined, and the organic layer was washed with 0.5mol / LNa2CO3 solution, dried over anhydrous Na2S04 and dried on a rotary evaporator the solvent was evaporated to give a brown oily liquid, 400 mesh column chromatography on basic alumina, eluent petroleum ether: ethyl acetate = 60: 1, to give a pale yellow oily liquid product to be 3-MPC products characterized by IR, MS and NMR spectra with the embodiment. the same as in Example l.

实施例3:取甲基环戊烯醇酮(MCP) 33.6g、四氢吡咯垸67.2g、对甲苯磺酸0.5g,甲醇810g, 将甲基环戊烯醇酮与四氢吡咯垸混合,加入催化剂对甲苯磺酸,快速升温至回流状态,回流时间是11小时,停止反应并蒸去溶剂,加入300g水,再用3(P/。的NaOH溶液调节pH"9, 然后用乙醚萃取该反应液,萃取完毕之后,合并有机层,有机层再用0.5mol/LNa2CO3溶液洗涤,再用无水Na2S04干燥,用旋转蒸发仪蒸去溶剂,得到棕黄色油状液体,用400目 Example 3: To methyl cyclopentenolone (MCP) 33.6g, 67.2 g of pyrrolidine embankment, p-toluenesulfonic acid 0.5g, 810G methanol, methyl cyclopentenolone embankment mixed with pyrrolidine, the catalyst was added p-toluenesulfonic acid, quickly warmed to reflux, reflux time is 11 hours, the solvent was distilled off and the reaction was stopped, 300g water was added, then 3 (P /. NaOH solution to adjust the pH "9, which was then extracted with ether The reaction solution, after completion of the extraction, the organic layers were combined, and the organic layer was washed with 0.5mol / LNa2CO3 solution, dried over anhydrous Na2S04 and dried on a rotary evaporator the solvent was evaporated to give a brown oily liquid, 400 mesh

的碱性氧化铝进行柱层析,洗脱液为石油醚:乙酸乙酯=60: l,得到淡黄色的油状液体为3-MPC产品。 Basic alumina column chromatography, eluent petroleum ether: ethyl acetate = 60: l, to give a pale yellow oily liquid product of 3-MPC. 产物经红外光谱、质谱及核磁共振谱加以表征与实施例i相同。 The product to be characterized by IR, MS and NMR spectra identical to Example i. 实施例4:制备方法同实施例1〜3,溶剂用乙醇替换。 Example 4: Preparation method as in Example 1 ~ 3, the solvent replaced with ethanol. 实施例5:按质量比计算,将49份磷酸氢钙、1.2份羧甲基纤维素、25份甘油、3份月桂醇硫酸钠、l份焦磷酸钠、1.3份香料、19.5份水混合均匀,经陈化后的(牙膏)膏体备用(牙膏基质);将上述合成得到的3-MPC溶解于乙醇溶液中,配制成溶液,然后以(含3-MPC) 0.001% (牙膏基质重量百分比)添加量加到上述膏体中,进一步混合均匀,经研磨、真空脱气、罐装即可。 Example 5: calculated mass ratio, 49 parts of calcium hydrogen phosphate, 1.2 parts of carboxymethyl cellulose, 25 parts glycerol, 3 parts of sodium lauryl sulfate, l part of sodium pyrophosphate, 1.3 parts perfume, 19.5 parts of water were mixed uniformly , after the aging (toothpaste) alternate paste (toothpaste matrix); synthesized above obtained 3-MPC was dissolved in ethanol to prepare a solution, and then (containing 3-MPC) 0.001% (weight percent of the toothpaste matrix ) added to the added amount of the paste further mixed, milled, vacuum degassing, can be canned. 经使用,与对照样品相比,该牙膏具有口腔凉爽、凉味持续时间长的特点。 It was used, compared to a control sample, with the toothpaste oral cool, cool taste characteristics of long duration. 实施例6:上述合成的3-MPC溶解于丙二醇溶液中配制成溶液,以(含3-MPC) 0.2% 添加量应用于牙膏膏体,其他同实施例5。 Example 6: 3-MPC synthesized above were dissolved in propylene glycol solution was formulated as a solution, the addition amount of 0.2% (including 3-MPC) paste is applied to toothpaste, with other embodiments 5. 实施例7:上述合成的3-MPC溶解于甘油溶液中配制成溶液,以(含3-MPC) 1%添加量应用于牙膏膏体,其他同实施例5。 Example 7: 3-MPC synthesized above was dissolved in glycerol solution formulated as a solution, added in an amount of 1% (including 3-MPC) paste is applied to toothpaste, with other embodiments 5. 实施例8:按质量比计算,将5份白砂糖、15份胶姆糖基础剂、64.4份葡萄糖浆、5 份填充剂、5份食用增塑剂、5份甘油、0.5份天然香料、0.1份抗氧化剂混合均匀备用(口香糖基质);将上述合成得到的3-MPC溶解于乙醇溶液中,配制成溶液,然后以(含3-MPC) 0.001% (口香糖基质重量百分比)添加量加到备用的混合体中,进一步混合均匀,经研磨后压成片状口香糖。 Example 8: mass calculated ratio, 5 parts of sugar, 15 parts gum base agent, 64.4 parts glucose syrup, 5 parts of a filler, 5 parts of edible plasticizer, 5 parts of glycerin, 0.5 parts of natural flavor, 0.1 spare parts antioxidant mixed (gum base); synthesized above obtained 3-MPC was dissolved in ethanol to prepare a solution, and then 0.001% (by weight gum base) added in an amount (including 3-MPC) was added to the standby a mixture, and further mixed, pressed into a sheet by grinding after chewing gum. 经使用,与对照样相比,该口香糖具有口味清新,凉味感均匀、持久等特点。 Once used, compared with the control sample, the chewing gum has a fresh taste, even a cooling sensation, lasting characteristics. 实施例9:上述合成的3-MPC溶解于丙二醇溶液中配制成溶液,以(含3-MPC) 0.2% 添加量应用于口香糖备用料上,其他同实施例8。 Example 9: 3-MPC synthesized above were dissolved in propylene glycol solution was formulated as a solution, the addition amount of 0.2% (including 3-MPC) is applied to prepare a chewing gum selected materials, the other with Example 8. 实施例10:上述合成的3-MPC溶解于甘油溶液中配制成溶液,以(含3-MPC) 1%添加量应用于口香糖备用料上,其他同实施例8。 Example 10: 3-MPC synthesized above was dissolved in glycerol solution formulated as a solution, added in an amount of 1% (including 3-MPC) is applied to prepare a chewing gum selected materials, the other with Example 8. 实施例11:将上述合成得到的3-MPC溶解于乙醇溶液中,配制成溶液,然后以(含3-MPC) 0.001% (烟丝质量百分比)添加量,将溶液均匀喷洒在烟丝上,在空气中晾干, 手工巻烟进行评吸。 Example 11: The above synthesis obtained 3-MPC was dissolved in ethanol to prepare a solution, and then 0.001% (tobacco mass%) Amount added (containing 3-MPC), the solution was uniformly sprayed on the tobacco in the air in dry, Volume fumigatus hand smoking. 经使用,与对照样相比,该巻烟具有明显的凉味感,持久均匀,而且口感舒适。 It was used, as compared with the control sample, which has obvious smoke Volume a cooling sensation, uniform durable, and comfortable texture. 实施例12:将上述合成得到的3-MPC溶解于甘油溶液中,配制成溶液,然后以(含3-MPC) 1% (烟丝质量百分比)添加量,将溶液均匀喷洒在烟丝上,其余同实施例ll。 Example 12: The above synthesis obtained 3-MPC was dissolved in glycerol solution to prepare a solution, and then with 1% (tobacco mass%) Amount added (containing 3-MPC), the solution was uniformly sprayed on the tobacco, and the rest with Example ll embodiment.

Claims (10)

  1. 1、一种α-酮基烯胺衍生物凉味剂的合成方法,其特征在于以甲基环戊烯醇酮和四氢吡咯烷为原料,按质量比为1∶1.8-2.0混合,加入反应物料总量0.2-0.5%的催化剂对甲苯磺酸,用溶剂回流,蒸去溶剂,加入水,再用NaOH溶液调节pH≈9,然后用乙醚萃取该反应液,萃取完毕之后,合并有机层,有机层再用Na2CO3溶液洗涤,再用无水Na2SO4干燥,蒸去溶剂,得到棕黄色油状液体,用碱性氧化铝进行柱层析,得到淡黄色的油状液体α-酮基烯胺衍生物凉味剂产品。 1, a method of synthesizing α- keto enamine derivatives, cooling agents, characterized in that the methyl cyclopentenolone and tetrahydro-pyrrolidine as starting material, a mass ratio of 1:1.8-2.0 mixed, 0.2-0.5% of the total reaction mass of the catalyst p-toluenesulfonic acid was refluxed with a solvent, the solvent was distilled off, water was added, the solution was adjusted with NaOH pH≈9, the reaction solution was then extracted with ether, after completion of the extraction, the organic layers were combined the organic layer was washed with Na2CO3 solution, dried over anhydrous Na2SO4, the solvent was evaporated to give a brown oily liquid, which was chromatographed on basic alumina to give a pale yellow oily liquid α- keto enamine derivatives cooling agents products.
  2. 2、 根据权利要求l所述的a-酮基烯胺衍生物凉味剂的合成方法,其特征在于合成反应所采用的溶剂是甲醇或乙醇,用量为反应物料总量的8倍。 2, synthesis method a- keto enamine derivative of the cooling agent according to claim l, characterized in that the synthetic reaction solvent employed is methanol or ethanol, in an amount of 8 times the total reaction mass.
  3. 3、 根据权利要求l所述的a-酮基烯胺衍生物凉味剂的合成方法,其特征在于回流反应时间为7-ll小时。 3, synthesis a- keto enamine derivative of the cooling agent according to claim l, characterized in that the reaction time was 7-ll hours.
  4. 4、 根据权利要求1或3所述5-MPC的合成方法,其特征在于回流反应时间最好为9小时。 4, according to claim 1 or 3 5-MPC synthesis method as claimed in claim, characterized in that the reaction time is preferably refluxed for 9 hours.
  5. 5、 根据权利要求l所述的a-酮基烯胺衍生物凉味剂的合成方法,其特征在于甲基环戊烯醇酮和四氢吡咯烷的质量比为l : 1.2—1.4,最好为l : 1.9。 5. The method of claim synthetic a- keto enamine derivatives cooling agents according to claim l, characterized in that the mass and methyl cyclopentenolone tetrahydro-pyrrolidine ratio of l: 1.2-1.4, most good to l: 1.9.
  6. 6、 根据权利要求l所述的a-酮基烯胺衍生物凉味剂的合成方法,其特征是在柱层析过程中的洗脱液为石油醚:乙酸乙酯=60 : l。 6, according to the synthetic method of Claim a- keto enamine derivatives cooling agents according to claim l, wherein the eluent for the chromatography column with petroleum ether: ethyl acetate = 60: l.
  7. 7、 权利要求l所述的a-酮基烯胺衍生物凉味剂的应用,其特征在于将a-酮基烯胺衍生物凉味剂与醇类溶剂配成溶液,按烟草重量百分比0.001-1%喷洒到叶组烟丝上。 7, the application l a- keto enamine derivatives as claimed in claim cooling agents, characterized in that a- keto enamine derivative with an alcoholic solvent cooling agents prepare a solution, by weight percent tobacco 0.001 -1% sprayed onto the tobacco leaf group.
  8. 8、 权利要求l所述的a-酮基烯胺衍生物凉味剂的应用,其特征在于将a-酮基烯胺衍生物凉味剂与醇类溶剂配成溶液,按牙膏基质重量百分比0.001-1%添加,混合均匀。 8, the application l a- keto enamine derivatives as claimed in claim cooling agents, characterized in that a- keto enamine derivative with an alcoholic solvent cooling agents prepare a solution, by weight percent of the toothpaste matrix 0.001 to 1% was added and mixed uniformly.
  9. 9、 权利要求l所述的a-酮基烯胺衍生物凉味剂的应用,其特征在于将a-酮基烯胺衍生物凉味剂与醇类溶剂配成溶液,按口香糖基质重量百分比0.001-1%添加,混合均匀。 9, use as claimed in claim l a- keto enamine derivatives, cooling agents, characterized in that a- keto enamine derivatives cooling agent formulated with an alcoholic solvent solution, the percentage by weight of the chewing gum base 0.001 to 1% was added and mixed uniformly.
  10. 10、 根据权利要求7或8或9所述的a-酮基烯胺衍生物凉味剂的应用,其特征在于所述的醇类溶剂为乙醇或丙二醇或甘油。 Application of a- keto enamine derivative 10 cooling agents, according to claim 7 or 8 or 9, wherein said alcoholic solvent is ethanol or propylene glycol or glycerol.
CN 200710066050 2007-07-20 2007-07-20 Synthesis method for alpha-carbonylenamine derivative cooling agent (3-MPC) and application thereof CN101125828A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN 200710066050 CN101125828A (en) 2007-07-20 2007-07-20 Synthesis method for alpha-carbonylenamine derivative cooling agent (3-MPC) and application thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN 200710066050 CN101125828A (en) 2007-07-20 2007-07-20 Synthesis method for alpha-carbonylenamine derivative cooling agent (3-MPC) and application thereof

Publications (1)

Publication Number Publication Date
CN101125828A true true CN101125828A (en) 2008-02-20

Family

ID=39093981

Family Applications (1)

Application Number Title Priority Date Filing Date
CN 200710066050 CN101125828A (en) 2007-07-20 2007-07-20 Synthesis method for alpha-carbonylenamine derivative cooling agent (3-MPC) and application thereof

Country Status (1)

Country Link
CN (1) CN101125828A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104961669A (en) * 2015-03-18 2015-10-07 河南农业大学 Preparation method for N-alkyl-2-methyl-5-formyl-3-pyrrole formate and application of N-alkyl2-methyl-5-formyl-3-pyrrole formate in cigarette flavoring
CN105175358A (en) * 2010-12-03 2015-12-23 陶氏益农公司 Processes for the preparation of enamines

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105175358A (en) * 2010-12-03 2015-12-23 陶氏益农公司 Processes for the preparation of enamines
CN104961669A (en) * 2015-03-18 2015-10-07 河南农业大学 Preparation method for N-alkyl-2-methyl-5-formyl-3-pyrrole formate and application of N-alkyl2-methyl-5-formyl-3-pyrrole formate in cigarette flavoring
CN104961669B (en) * 2015-03-18 2018-02-13 河南农业大学 N- methyl-5 hydrocarbon preparing formyl-3-pyrrole carboxylate Its Application in Tobacco Flavoring

Similar Documents

Publication Publication Date Title
WO1985003637A1 (en) Methods and pharmaceutical compositions for the treatment of hyperplastic diseases of the skin
CN103070472A (en) Electronic cigarette liquid capable of effectively improving sensory quality of electronic cigarette
CN101411543A (en) Method for preparing flavoring for cigarette and use
CN101305836A (en) Method and device for preparing expanded stem granule
CN101375735A (en) Method for preparing burley tobacco expanded tobacco shred for low-coke tar flue-cured type cigarette
CN1994164A (en) Acetate plasticizer for improving smoking property of cigarette and method for preparing same
CN103099310A (en) Tobacco moistening agent and application thereof
CN101233890A (en) Hard sugar containing tobacco component
CN104839883A (en) Electronic cigarette liquid with characteristics of tobaccos for tobacco pipes
CN101862024A (en) Refreshing tablets containing tobacco components
CN102100397A (en) Flavoring essence for tobacco and preparation method thereof
CN101485490A (en) Preparation method of additive agent capable of causing flue-cured tobacco to have fragrance of oolong tea, flavoring as well as application in flue-cured tobacco
CN103989245A (en) Chinese flue-cured tobacco type electronic cigarette liquid capable of effectively reducing oral cavity sweet greasy feeling
CN102894465A (en) Tobacco-containing areca catechu and preparation method thereof
JP2004307491A (en) Skin care preparation for external use containing heparinoid
CN102579305A (en) Natural medicine toothpaste with saussurea involucrata as major material
CN103284323A (en) Tobacco sweetening agent for cigarettes and application method of tobacco sweetening agent
CN102058148A (en) Process for baking Hongda tobacco leaves
JPH09510627A (en) Cool sense of composition
CN101942361A (en) Jujube flavor base, and preparation method and application thereof
CN101596014A (en) Method for preparing ultra-low tar cigarette shreds
CN105249524A (en) Fragrance type heating nonflammable tobacco product and preparation method thereof
CN102423114A (en) Low-tar cigarette aroma compensation method
CN102090712A (en) Method for preparing coarse extract of peanut shell total flavones and application thereof in cigarettes
JPH0782588A (en) Controlling method for perfume emission

Legal Events

Date Code Title Description
C06 Publication
C10 Request of examination as to substance
C02 Deemed withdrawal of patent application after publication (patent law 2001)