CN117510450A - 一种麦芽酚碳酸酯及其合成方法与应用 - Google Patents
一种麦芽酚碳酸酯及其合成方法与应用 Download PDFInfo
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- maltol
- carbonate
- chloroformate
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- butyl
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- GXCLVBGFBYZDAG-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine Chemical compound CN(CCC1=CNC2=C1C=CC=C2)CC=C GXCLVBGFBYZDAG-UHFFFAOYSA-N 0.000 title claims description 6
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 title claims description 6
- 238000010189 synthetic method Methods 0.000 title description 3
- XPCTZQVDEJYUGT-UHFFFAOYSA-N 3-hydroxy-2-methyl-4-pyrone Chemical compound CC=1OC=CC(=O)C=1O XPCTZQVDEJYUGT-UHFFFAOYSA-N 0.000 claims abstract description 141
- HYMLWHLQFGRFIY-UHFFFAOYSA-N Maltol Natural products CC1OC=CC(=O)C1=O HYMLWHLQFGRFIY-UHFFFAOYSA-N 0.000 claims abstract description 72
- 229940043353 maltol Drugs 0.000 claims abstract description 72
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims abstract description 39
- 235000019504 cigarettes Nutrition 0.000 claims abstract description 36
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims abstract description 18
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims abstract description 9
- -1 maltol carbonates Chemical class 0.000 claims abstract description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 27
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 8
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 241000208125 Nicotiana Species 0.000 claims description 4
- 235000002637 Nicotiana tabacum Nutrition 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 claims description 4
- 150000007530 organic bases Chemical class 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 238000005406 washing Methods 0.000 claims description 4
- QVCQPIJMAAOGKX-UHFFFAOYSA-N (2,4,5-trimethylphenyl)thiourea Chemical compound CC1=CC(C)=C(NC(N)=S)C=C1C QVCQPIJMAAOGKX-UHFFFAOYSA-N 0.000 claims description 2
- YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 239000002585 base Substances 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- YSMHTFWPDRJCMN-UHFFFAOYSA-N butan-2-yl carbonochloridate Chemical compound CCC(C)OC(Cl)=O YSMHTFWPDRJCMN-UHFFFAOYSA-N 0.000 claims description 2
- AFPOMDNRTZLRMD-UHFFFAOYSA-N dodecyl carbonochloridate Chemical compound CCCCCCCCCCCCOC(Cl)=O AFPOMDNRTZLRMD-UHFFFAOYSA-N 0.000 claims description 2
- 125000003438 dodecyl 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])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000913 palmityl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- XHRRYUDVWPPWIP-UHFFFAOYSA-N pentyl carbonochloridate Chemical compound CCCCCOC(Cl)=O XHRRYUDVWPPWIP-UHFFFAOYSA-N 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- UJJDEOLXODWCGK-UHFFFAOYSA-N tert-butyl carbonochloridate Chemical compound CC(C)(C)OC(Cl)=O UJJDEOLXODWCGK-UHFFFAOYSA-N 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 239000003205 fragrance Substances 0.000 abstract description 20
- 238000001308 synthesis method Methods 0.000 abstract description 4
- 235000009508 confectionery Nutrition 0.000 description 17
- 229940125904 compound 1 Drugs 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- 238000004227 thermal cracking Methods 0.000 description 9
- 239000000796 flavoring agent Substances 0.000 description 8
- 235000019634 flavors Nutrition 0.000 description 8
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 239000012494 Quartz wool Substances 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 210000000214 mouth Anatomy 0.000 description 4
- 239000010453 quartz Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- HIHOEGPXVVKJPP-JTQLQIEISA-N 5-fluoro-2-[[(1s)-1-(5-fluoropyridin-2-yl)ethyl]amino]-6-[(5-methyl-1h-pyrazol-3-yl)amino]pyridine-3-carbonitrile Chemical compound N([C@@H](C)C=1N=CC(F)=CC=1)C(C(=CC=1F)C#N)=NC=1NC=1C=C(C)NN=1 HIHOEGPXVVKJPP-JTQLQIEISA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000010835 comparative analysis Methods 0.000 description 3
- 238000005336 cracking Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000003359 percent control normalization Methods 0.000 description 3
- 239000000779 smoke Substances 0.000 description 3
- YGSIRXHFAUFUEJ-GPTQDWHKSA-N 2-Methyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypyran-4-one Chemical compound O1C=CC(=O)C(O[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)=C1C YGSIRXHFAUFUEJ-GPTQDWHKSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 235000019445 benzyl alcohol Nutrition 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 2
- JFOZKMSJYSPYLN-QHCPKHFHSA-N lifitegrast Chemical compound CS(=O)(=O)C1=CC=CC(C[C@H](NC(=O)C=2C(=C3CCN(CC3=CC=2Cl)C(=O)C=2C=C3OC=CC3=CC=2)Cl)C(O)=O)=C1 JFOZKMSJYSPYLN-QHCPKHFHSA-N 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000003546 flue gas Substances 0.000 description 1
- 229930182478 glucoside Natural products 0.000 description 1
- 229930182470 glycoside Natural products 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/34—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D309/36—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
- C07D309/40—Oxygen atoms attached in positions 3 and 4, e.g. maltol
-
- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
- A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
- A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
- A24B15/18—Treatment of tobacco products or tobacco substitutes
- A24B15/28—Treatment of tobacco products or tobacco substitutes by chemical substances
- A24B15/30—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances
- A24B15/36—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring
- A24B15/40—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring having only oxygen or sulfur as hetero atoms
- A24B15/403—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring having only oxygen or sulfur as hetero atoms having only oxygen as hetero atoms
-
- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
- A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
- A24B3/00—Preparing tobacco in the factory
- A24B3/12—Steaming, curing, or flavouring tobacco
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Manufacture Of Tobacco Products (AREA)
Abstract
本申请公开了一种麦芽酚碳酸酯及其合成方法与应用,将麦芽酚溶于二氯甲烷中,加入氯甲酸酯或固体光气,反应后得到麦芽酚碳酸酯。麦芽酚碳酸酯中的一种或几种,经与丙二醇、丙三醇混合后应用于加热卷烟加香,麦芽酚碳酸酯在加热卷烟工作时裂解释放麦芽酚,其主要作用是凸显加热卷烟焦甜香气,提高加热卷烟口腔舒适性。
Description
技术领域
本申请涉及香料技术领域,特别是涉及一种麦芽酚碳酸酯及其合成方法与应用。
背景技术
加热卷烟依靠热源加热形成主流烟气气溶胶,其加热而非燃烧的产品属性,导致烟丝受热发生的裂解反应较为简单,香气成分释放受限,存在香气不足、烟气浓度较低、消费者满足感不强等问题。如何对加热卷烟进行香气补偿,增加香气质及香气量、实现香气均匀释放及增强消费者满足感,是该领域亟需解决的关键技术问题之一。
麦芽酚是一种在食品和卷烟领域广泛应用的香料,可以增加烘焙食品、糖果、卷烟烟气的焦甜香香气。然而麦芽酚嗅香较重,应用于卷烟中在嗅闻时会掩盖卷烟的自然香气,因此,有文献报道合成了潜香化合物麦芽酚糖苷和麦芽酚锌配合物,应用于常规卷烟加香,糖苷键和配位键在卷烟燃吸时可裂解释放出麦芽酚。但由于加热卷烟烟丝受热温度区间为100-260℃,文献所述的麦芽酚糖苷和麦芽酚锌配合物在加热卷烟中难以有效裂解,因此,有必要开发在加热卷烟温度下可裂解的麦芽酚潜香化合物。
发明内容
为解决上述技术问题,本发明提供一种麦芽酚碳酸酯及其合成方法与应用,本发明的麦芽酚碳酸酯在加热卷烟温度下可裂解,释放出麦芽酚,添加至加热卷烟中,可赋予明显的焦甜香风格。
本发明提供的技术方案如下:
一种麦芽酚碳酸酯,所述麦芽酚碳酸酯的分子式如下:
其中,R所代表的的基团选自:正戊基、异丁基、仲丁基、叔丁基、月桂基、十六烷基、苄基和麦芽酚基中的一种。
一种麦芽酚碳酸酯的制备方法,所述麦芽酚碳酸酯的制备过程如下:将麦芽酚溶于二氯甲烷中,再依次加入三乙胺(三乙胺是碱、缚酸剂)和氯甲酸酯,室温反应至反应完全后,反应后的溶液依次经洗涤、干燥、减压浓缩得到麦芽酚碳酸酯。
上述的麦芽酚碳酸酯的制备方法合成路线如下:
优选地,氯甲酸酯为氯甲酸正戊酯、氯甲酸异丁酯、氯甲酸仲丁酯、氯甲酸叔丁酯、氯甲酸月桂酯、氯甲酸十六酯和氯甲酸苄酯中的一种。
优选地,所得到的麦芽酚碳酸酯具体为麦芽酚碳酸烷基酯,所述麦芽酚碳酸烷基酯包括如下分子式的物质:
优选地,所加入的麦芽酚、三乙胺和氯甲酸苄酯物质的量之比为1:(1~1.5):(1~1.2)。
一种麦芽酚碳酸酯的制备方法,所述麦芽酚碳酸酯的制备过程如下:将麦芽酚溶于溶剂中,加入有机碱(有机碱的作用是分解固体光气使其生成光气,同时还可以作为缚酸剂,促进反应的进行),然后缓慢加入固体光气的溶液,室温反应至反应完全,反应后的溶液经洗涤、干燥,减压浓缩得到麦芽酚碳酸酯。
上述的麦芽酚碳酸酯的制备方法合成路线如下:
优选地,所得到的麦芽酚碳酸酯具体为麦芽酚碳酸二酯,分子式如下:
优选地,所述有机碱为三乙胺、吡啶中的一种,所述溶剂为二氯甲烷、甲苯中的一种,所加入的麦芽酚、碱和固体光气的物质的量之比为1:(1~1.5):(0.16~0.25)。
一种加热卷烟,其内添加有上述所述的麦芽酚碳酸酯或上述所述的制备方法得到的麦芽酚碳酸酯。
优选地,所述麦芽酚碳酸酯经丙二醇或丙三醇稀释后加入到加热卷烟中,麦芽酚碳酸酯经稀释后加入到加热卷烟中,以保证其在加热卷烟中的分布均匀性,麦芽酚碳酸酯的添加量为加热卷烟烟丝质量的万分之一至千分之一之间。
本申请相对于现有技术存在如下优点:
本发明的方法以麦芽酚为原料,通过一步反应得到麦芽酚碳酸酯,产率高,制备操作方法简便;所制备得到的麦芽酚碳酸酯基本无嗅,改善了麦芽酚嗅香重的缺点;碳酸酯键为热不稳定键,受热易分解,因此,麦芽酚碳酸酯在加热卷烟温度下裂解释放出麦芽酚,添加至加热卷烟中,可赋予明显的焦甜香风格。
具体实施方式
为了使本领域的技术人员更好地理解本申请中的技术方案,下面将对本申请实施例中的技术方案进行清楚、完整地描述,显然,所描述的实施例仅仅是本申请的一部分实施例,而不是全部的实施例。基于本申请中的实施例,本领域普通技术人员在没有做出创造性劳动前提下所获得的所有其他实施例,都属于本申请保护的范围。
实施例1:
化合物1a~1g的合成方法如下:
麦芽酚(1.26g,10mmol)溶于30mL二氯甲烷中,加入三乙胺(1.11g,11mmol),冷至0℃,缓慢滴加氯甲酸酯(10.5mmol),加毕升至室温反应至完全,反应液用饱和NaCl溶液洗涤2次,无水Na2SO4干燥,减压浓缩得到化合物1a~1g。
化合物1a的核磁数据:1H NMR(600MHz,CDCl3)δ7.68(d,J=5.7Hz,1H),6.42(d,J=5.7Hz,1H),4.27(t,J=6.8Hz,2H),1.88–1.70(m,2H),1.61
1.30(m,4H),0.92(t,J=7.0Hz,3H).13C NMR(150MHz,CDCl3)δ171.9,159.2,154.2,152.1,139.1,117.0,69.8,28.2,27.7,22.3,14.9,13.9。
化合物1b的核磁数据:1H NMR(600MHz,CDCl3)δ7.68(d,J=5.7Hz,1H),6.42(d,J=5.7Hz,1H),4.06(d,J=6.7Hz,2H),2.33(s,3H),2.06(dt,J=13.5,6.7Hz,1H),1.00(d,J=6.8Hz,6H).13C NMR(150MHz,CDCl3)δ171.9,159.2,154.2,152.1,139.1,117.0,75.5,27.8,18.8,14.9。
化合物1c的核磁数据:1H NMR(600MHz,CDCl3)δ7.68(d,J=5.7Hz,1H),6.42(d,J=5.7Hz,1H),5.09–4.48(m,1H),2.32(s,3H),1.81–1.72(m,1H),1.71–1.61(m,1H),1.36(d,J=6.3Hz,3H),0.99(t,J=7.5Hz,3H).13C NMR(150MHz,CDCl3)δ171.97,159.13,154.21,151.71,139.13,117.00,78.72,28.67,19.19,14.90,9.52。
化合物1d的核磁数据:1H NMR(600MHz,CDCl3)δ7.69(d,J=5.7Hz,1H),6.40(d,J=5.7Hz,1H),2.31(s,3H),1.55(s,9H).13C NMR(150MHz,CDCl3)δ172.1,159.1,154.2,150.1,139.0,116.9,84.5,27.5,14.9。
化合物1e的核磁数据:1H NMR(600MHz,CDCl3)δ7.68(d,J=5.7Hz,1H),6.42(d,J=5.7Hz,1H),4.27(t,J=6.8Hz,2H),2.32(s,3H),1.84–1.71(m,2H),1.30(m,18H),0.90(t,J=7.0Hz,3H).13C NMR(150MHz,CDCl3)δ171.9,159.2,154.2,152.1,139.1,117.0,71.4,30.9,29.7,29.7,29.6,29.6,29.5,29.2,28.0,26.6,22.3,14.6,13.9。
化合物1f的核磁数据:1H NMR(600MHz,CDCl3)δ7.67(d,J=5.7Hz,1H),6.42(d,J=5.7Hz,1H),4.26(t,J=6.8Hz,2H),2.32(s,3H),1.79–1.62(m,2H),1.26(m,26H),0.88(t,J=7.0Hz,3H).13C NMR(150MHz,CDCl3)δ171.9,159.2,154.2,152.1,139.1,117.0,69.8,31.9,29.7,29.7,29.7,29.6,29.6,29.5,29.4,29.2,28.5,25.6,22.7,14.9,14.1。
化合物1g的核磁数据:1H NMR(600MHz,CDCl3)δ7.67(d,J=5.7Hz,1H),7.36-7.43(m,5H),6.42(d,J=5.8Hz,1H),5.29(s,2H),2.29(s,3H).13C NMR(150MHz,CDCl3)δ171.8,159.3,154.3,152.0,139.1,134.5,128.7,128.4,117.0,71.7,14.9。
实施例2:
化合物1h的合成方法如下:
麦芽酚(1.26g,10mmol)溶于二氯甲烷中,加入三乙胺(12.12g,12mmol),缓慢滴加固体光气(0.59g,0.2mmol)的二氯甲烷溶液,加毕室温反应至完全,反应液用饱和NaCl溶液洗涤2次,无水Na2SO4干燥,减压浓缩,残留物进行硅胶柱层析,石油醚/乙酸乙酯=2/1洗脱,得到化合物1h。
化合物1g的核磁数据:1H NMR(600MHz,CDCl3)δ7.70(d,J=5.8Hz,1H),6.43(d,J=5.7Hz,1H),2.47(s,3H).13C NMR(150MHz,CDCl3)δ171.5,160.2,154.5,139.1,117.0,15.1。
实施例3:
化合物1d的热裂解:
制样:裂解石英管中塞入适量石英棉,称取样品约0.1mg加入到石英管中,再塞入适量石英棉,待热裂解分析。无氧热裂解条件:初始温度:50℃;以20℃/ms分别升温到150℃、200℃、250℃、300℃后,保持15s,然后将裂解产物导入GC-MS进行分析。热裂解产物如表1所示,主要为麦芽酚。
表1化合物1g热裂解产物
序号 | 时间(min) | 化合物名称 |
1 | 16.59 | 麦芽酚 |
实施例4:
化合物1g的热裂解:
制样:裂解石英管中塞入适量石英棉,称取样品约0.1mg加入到石英管中,再塞入适量石英棉,待热裂解分析。无氧热裂解条件:初始温度:50℃;以20℃/ms分别升温到150℃、200℃、250℃、300℃后,保持15s,然后将裂解产物导入GC-MS进行分析。热裂解产物如表2所示,主要为麦芽酚和苯甲醇。
表2化合物1g热裂解产物
序号 | 时间(min) | 化合物名称 |
1 | 14.10 | 苯甲醇 |
2 | 16.62 | 麦芽酚 |
实施例5:
麦芽酚碳酸酯在加热卷烟中的应用:
称取化合物1d 200mg,以丙二醇定容至2mL,并依次稀释。将配置好的不同浓度溶液均匀地加入到加热卷烟中,添加梯度量为卷烟薄片质量的0.01%,0.02%,0.05%,0.1%,同空白样品对照评吸,结果如表3所示。由表3可知:化合物1d在卷烟加香中的作用主要是增强焦甜香韵、提高口腔舒适度。
表3对照评吸结果
空白对照 | 香气质香气量一般,口感一般。 |
麦芽酚0.02%对照 | 嗅香过重 |
0.01% | 焦甜香有所增加 |
0.02% | 焦甜香增加,口腔舒适度有改善 |
0.05% | 焦甜香明显,口腔舒适度提高 |
0.1% | 焦甜香过于显露 |
称取化合物1h 200mg,以丙二醇定容至2mL,并依次稀释。将配置好的不同浓度溶液均匀地加入到加热卷烟中,添加梯度量为卷烟薄片质量的0.01%,0.02%,0.05%,0.1%,同空白样品对照评吸,结果如表4所示。由表4可知,化合物1h在卷烟加香中的作用主要是增强焦甜香韵和花香香韵。
表4对照评吸结果
添加量 | 评吸结果 |
空白对照 | 香气质香气量一般,口感一般。 |
麦芽酚0.05%对照 | 嗅香过重 |
0.01% | 焦甜香有所增加,有花香 |
0.02% | 甜香增加,与花香较协调 |
0.05% | 焦甜香明显,花香过于显露 |
0.1% | 焦甜香、花香过于显露 |
称取化合物1d和1h各100mg,以丙二醇定容至2mL,并依次稀释。将配置好的不同浓度溶液均匀地加入到加热卷烟中,添加梯度量为卷烟薄片质量的0.01%,0.02%,0.05%,0.1%,同空白样品对照评吸,结果如表5所示。由表5可知:化合物1d和1h混合在卷烟加香中的作用主要是增强焦甜香韵和花香,提高口腔舒适度。
表5对照评吸结果
空白对照 | 香气质香气量一般,口感一般。 |
麦芽酚0.02%对照 | 嗅香过重 |
0.01% | 焦甜香有所增加 |
0.02% | 焦甜香增加 |
0.05% | 焦甜香明显,口腔舒适度增加 |
0.1% | 焦甜香过于显露 |
对所公开的实施例的上述说明,使本领域专业技术人员能够实现或使用本发明。对这些实施例的多种修改对本领域的专业技术人员来说将是显而易见的,本文中所定义的一般原理可以在不脱离本发明的精神或范围的情况下,在其它实施例中实现。因此,本发明将不会被限制于本文所示的这些实施例,而是要符合与本文所公开的原理和新颖特点相一致的最宽的范围。
Claims (10)
1.一种麦芽酚碳酸酯,其特征在于,所述麦芽酚碳酸酯的分子式如下:
其中,R所代表的的基团选自:正戊基、异丁基、仲丁基、叔丁基、月桂基、十六烷基、苄基和麦芽酚基中的一种。
2.一种麦芽酚碳酸酯的制备方法,其特征在于,所述麦芽酚碳酸酯的制备过程如下:将麦芽酚溶于二氯甲烷中,再依次加入三乙胺和氯甲酸酯,室温反应至反应完全后,反应后的溶液依次经洗涤、干燥、减压浓缩得到麦芽酚碳酸酯。
3.根据权利要求2所述的麦芽酚碳酸酯的制备方法,其特征在于,氯甲酸酯为氯甲酸正戊酯、氯甲酸异丁酯、氯甲酸仲丁酯、氯甲酸叔丁酯、氯甲酸月桂酯、氯甲酸十六酯和氯甲酸苄酯中的一种。
4.根据权利要求3所述的麦芽酚碳酸酯的制备方法,其特征在于,所得到的麦芽酚碳酸酯具体为麦芽酚碳酸烷基酯,所述麦芽酚碳酸烷基酯包括如下分子式的物质:
5.根据权利要求2所述的麦芽酚碳酸酯的制备方法,其特征在于,所加入的麦芽酚、三乙胺和氯甲酸苄酯物质的量之比为1:(1~1.5):(1~1.2)。
6.一种麦芽酚碳酸酯的制备方法,其特征在于,所述麦芽酚碳酸酯的制备过程如下:将麦芽酚溶于溶剂中,加入有机碱,然后缓慢加入固体光气的溶液,室温反应至反应完全,反应后的溶液经洗涤、干燥,减压浓缩得到麦芽酚碳酸酯。
7.根据权利要求6所述的麦芽酚碳酸酯的制备方法,其特征在于,所得到的麦芽酚碳酸酯具体为麦芽酚碳酸二酯,分子式如下:
8.根据权利要求6所述的麦芽酚碳酸酯的制备方法,其特征在于,所述有机碱为三乙胺、吡啶中的一种,所述溶剂为二氯甲烷、甲苯中的一种,所加入的麦芽酚、碱和固体光气的物质的量之比为1:(1~1.5):(0.16~0.25)。
9.一种加热卷烟,其特征在于,其内添加有权利要求1所述的麦芽酚碳酸酯或权利要求2-8中任一项所述的制备方法得到的麦芽酚碳酸酯。
10.根据权利要求9所述的加热卷烟,其特征在于,所述麦芽酚碳酸酯经丙二醇或丙三醇稀释后加入到加热卷烟中,麦芽酚碳酸酯的添加量为加热卷烟烟丝质量的万分之一至千分之一之间。
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