CN101974040A - Five-carbon or six-carbon monosaccharide-L-menthoxyacetyl acid monoester compound as well as preparation method and application thereof - Google Patents
Five-carbon or six-carbon monosaccharide-L-menthoxyacetyl acid monoester compound as well as preparation method and application thereof Download PDFInfo
- Publication number
- CN101974040A CN101974040A CN 201010524908 CN201010524908A CN101974040A CN 101974040 A CN101974040 A CN 101974040A CN 201010524908 CN201010524908 CN 201010524908 CN 201010524908 A CN201010524908 A CN 201010524908A CN 101974040 A CN101974040 A CN 101974040A
- Authority
- CN
- China
- Prior art keywords
- carbon
- meng
- ethoxyacetic acid
- monose
- preparation
- 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.)
- Granted
Links
- 229910052799 carbon Inorganic materials 0.000 title claims abstract description 90
- 150000001875 compounds Chemical class 0.000 title claims abstract description 51
- 238000002360 preparation method Methods 0.000 title claims abstract description 30
- 239000002253 acid Substances 0.000 title abstract 5
- 241000208125 Nicotiana Species 0.000 claims abstract description 44
- 235000002637 Nicotiana tabacum Nutrition 0.000 claims abstract description 44
- 239000003906 humectant Substances 0.000 claims abstract description 20
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 77
- LPQOADBMXVRBNX-UHFFFAOYSA-N ac1ldcw0 Chemical compound Cl.C1CN(C)CCN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN3CCSC1=C32 LPQOADBMXVRBNX-UHFFFAOYSA-N 0.000 claims description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 21
- 150000002148 esters Chemical class 0.000 claims description 20
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 19
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 18
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 16
- 238000006482 condensation reaction Methods 0.000 claims description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 15
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 11
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- 239000000600 sorbitol Substances 0.000 claims description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 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 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 5
- 229920000728 polyester Polymers 0.000 claims description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 4
- PYMYPHUHKUWMLA-LMVFSUKVSA-N Ribose Natural products OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 claims description 4
- ZWWWLCMDTZFSOO-UHFFFAOYSA-N diethoxyphosphorylformonitrile Chemical compound CCOP(=O)(C#N)OCC ZWWWLCMDTZFSOO-UHFFFAOYSA-N 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 4
- MEIRRNXMZYDVDW-MQQKCMAXSA-N (2E,4E)-2,4-hexadien-1-ol Chemical compound C\C=C\C=C\CO MEIRRNXMZYDVDW-MQQKCMAXSA-N 0.000 claims description 3
- WQZGKKKJIJFFOK-CBPJZXOFSA-N D-Gulose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@H](O)[C@H]1O WQZGKKKJIJFFOK-CBPJZXOFSA-N 0.000 claims description 3
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 3
- ZAQJHHRNXZUBTE-NQXXGFSBSA-N D-ribulose Chemical compound OC[C@@H](O)[C@@H](O)C(=O)CO ZAQJHHRNXZUBTE-NQXXGFSBSA-N 0.000 claims description 3
- ZAQJHHRNXZUBTE-UHFFFAOYSA-N D-threo-2-Pentulose Natural products OCC(O)C(O)C(=O)CO ZAQJHHRNXZUBTE-UHFFFAOYSA-N 0.000 claims description 3
- ZAQJHHRNXZUBTE-WUJLRWPWSA-N D-xylulose Chemical compound OC[C@@H](O)[C@H](O)C(=O)CO ZAQJHHRNXZUBTE-WUJLRWPWSA-N 0.000 claims description 3
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 claims description 3
- 229930195725 Mannitol Natural products 0.000 claims description 3
- SRBFZHDQGSBBOR-STGXQOJASA-N alpha-D-lyxopyranose Chemical compound O[C@@H]1CO[C@H](O)[C@@H](O)[C@H]1O SRBFZHDQGSBBOR-STGXQOJASA-N 0.000 claims description 3
- -1 carbon monose compound Chemical class 0.000 claims description 3
- 238000005660 chlorination reaction Methods 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- 239000008103 glucose Substances 0.000 claims description 3
- DCPMPXBYPZGNDC-UHFFFAOYSA-N hydron;methanediimine;chloride Chemical compound Cl.N=C=N DCPMPXBYPZGNDC-UHFFFAOYSA-N 0.000 claims description 3
- 239000000594 mannitol Substances 0.000 claims description 3
- 235000010355 mannitol Nutrition 0.000 claims description 3
- 238000000746 purification Methods 0.000 claims description 3
- 229960003487 xylose Drugs 0.000 claims description 3
- GPIQOFWTZXXOOV-UHFFFAOYSA-N 2-chloro-4,6-dimethoxy-1,3,5-triazine Chemical compound COC1=NC(Cl)=NC(OC)=N1 GPIQOFWTZXXOOV-UHFFFAOYSA-N 0.000 claims description 2
- HMFHBZSHGGEWLO-SOOFDHNKSA-N D-ribofuranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-SOOFDHNKSA-N 0.000 claims description 2
- 229930091371 Fructose Natural products 0.000 claims description 2
- 239000005715 Fructose Substances 0.000 claims description 2
- LKDRXBCSQODPBY-AMVSKUEXSA-N L-(-)-Sorbose Chemical compound OCC1(O)OC[C@H](O)[C@@H](O)[C@@H]1O LKDRXBCSQODPBY-AMVSKUEXSA-N 0.000 claims description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 2
- HMFHBZSHGGEWLO-UHFFFAOYSA-N alpha-D-Furanose-Ribose Natural products OCC1OC(O)C(O)C1O HMFHBZSHGGEWLO-UHFFFAOYSA-N 0.000 claims description 2
- WQZGKKKJIJFFOK-PQMKYFCFSA-N alpha-D-mannose Chemical compound OC[C@H]1O[C@H](O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-PQMKYFCFSA-N 0.000 claims description 2
- SRBFZHDQGSBBOR-LECHCGJUSA-N alpha-D-xylose Chemical compound O[C@@H]1CO[C@H](O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-LECHCGJUSA-N 0.000 claims description 2
- SRBFZHDQGSBBOR-QMKXCQHVSA-N alpha-L-arabinopyranose Chemical compound O[C@H]1CO[C@@H](O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-QMKXCQHVSA-N 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 238000004440 column chromatography Methods 0.000 claims description 2
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims description 2
- 229940011051 isopropyl acetate Drugs 0.000 claims description 2
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 239000002994 raw material Substances 0.000 claims description 2
- 238000001953 recrystallisation Methods 0.000 claims description 2
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 2
- 239000007810 chemical reaction solvent Substances 0.000 claims 1
- 230000003578 releasing effect Effects 0.000 abstract description 10
- 238000012360 testing method Methods 0.000 abstract description 7
- 239000003205 fragrance Substances 0.000 abstract description 4
- 239000000126 substance Substances 0.000 abstract description 2
- 230000002457 bidirectional effect Effects 0.000 abstract 1
- 150000002772 monosaccharides Chemical class 0.000 abstract 1
- 238000010189 synthetic method Methods 0.000 abstract 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 24
- 238000000034 method Methods 0.000 description 17
- 238000001269 time-of-flight mass spectrometry Methods 0.000 description 16
- 230000000694 effects Effects 0.000 description 13
- 235000013772 propylene glycol Nutrition 0.000 description 8
- 235000019504 cigarettes Nutrition 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 150000004880 oxines Chemical class 0.000 description 7
- 239000000796 flavoring agent Substances 0.000 description 6
- 235000019634 flavors Nutrition 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 150000002240 furans Chemical class 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 230000001681 protective effect Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000002353 D-glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 2
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- PQLFROTZSIMBKR-UHFFFAOYSA-N ethenyl carbonochloridate Chemical compound ClC(=O)OC=C PQLFROTZSIMBKR-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 229950003934 mannite hexanitrate Drugs 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 2
- 239000002304 perfume Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- IVRIRQXJSNCSPQ-UHFFFAOYSA-N propan-2-yl carbonochloridate Chemical compound CC(C)OC(Cl)=O IVRIRQXJSNCSPQ-UHFFFAOYSA-N 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 235000013599 spices Nutrition 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- 229940084778 1,4-sorbitan Drugs 0.000 description 1
- OBTZDIRUQWFRFZ-UHFFFAOYSA-N 2-(5-methylfuran-2-yl)-n-(4-methylphenyl)quinoline-4-carboxamide Chemical compound O1C(C)=CC=C1C1=CC(C(=O)NC=2C=CC(C)=CC=2)=C(C=CC=C2)C2=N1 OBTZDIRUQWFRFZ-UHFFFAOYSA-N 0.000 description 1
- BMTZEAOGFDXDAD-UHFFFAOYSA-M 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholin-4-ium;chloride Chemical compound [Cl-].COC1=NC(OC)=NC([N+]2(C)CCOCC2)=N1 BMTZEAOGFDXDAD-UHFFFAOYSA-M 0.000 description 1
- RFSUNEUAIZKAJO-VRPWFDPXSA-N D-Fructose Natural products OC[C@H]1OC(O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-VRPWFDPXSA-N 0.000 description 1
- LKDRXBCSQODPBY-IANNHFEVSA-N D-sorbose Chemical compound OCC1(O)OC[C@@H](O)[C@H](O)[C@H]1O LKDRXBCSQODPBY-IANNHFEVSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical group CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 1
- 239000012982 microporous membrane Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 235000019633 pungent taste Nutrition 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 230000035807 sensation Effects 0.000 description 1
- 235000019615 sensations Nutrition 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a five-carbon or six-carbon monosaccharide-L-menthoxyacetyl acid monoester compound as well as a preparation method and application thereof, which relate to a monosaccharide monoester tobacco humectant. The invention is used for preparing a novel five-carbon or six-carbon monosaccharide-L-menthoxyacetyl acid monoester compound shown in a formula (1) through a chemical synthetic method and for testing the moisture-preserving, damp-proof and material-fragrance slow-releasing effects of the five-carbon or six-carbon monosaccharide-L-menthoxyacetyl acid monoester compound used as the tobacco humectant. Test results indicate that the monosaccharide-L-menthoxyacetyl acid monoester compound has the moisture-preserving, damp-proof and material-fragrance slow-releasing actions for tobacco and is a novel tobacco humectant having a bidirectional moisture-preserving action and a material-fragrance slow-releasing action; and in the formula (1), R represents the residue of five-carbon monosaccharide or six-carbon monosaccharide.
Description
Technical field
The invention belongs to technical field of tobacco, relate to a class monose monoesters class tobacco humectant, be specifically related to five carbon or six carbon monose-L-ethoxyacetic acid in Meng monoester class compound, Preparation Method And The Use.
Background technology
Cigarette humectation performance and cigarette quality are in close relations, and flavouring humectation technical study is one of main direction of science and technology coming years research of China's tobacco industry and scientific and technical innovation.At present, the humectant that adopts in China's production of cigarettes is mainly polyhydroxy substances such as glycerine, propylene glycol, Xylitol, mainly relies on moisture in its absorbing environmental to keep pipe tobacco wetting and play the humectation effect, belongs to unidirectional humectant; Though this type of humectant can be kept the water ratio of pipe tobacco in the course of processing, improve the anti-processibility of pipe tobacco, it keeps the finished cigarettes water ratio and improves the effect of sucking comfort level really not satisfactory.In addition, because this type of poly-hydroxy class humectant does not have moisture-proof role, water ratio with tobacco that this type of humectant is handled is subjected to the influence of environment temperature, humidity bigger, promptly tobacco easily dries out and causes its dry sensation and pungency to strengthen in the exsiccant environment, and tobacco easily absorbs moisture and causes its moldy metamorphism in the warm environment of humidity.Therefore, research and develop novel having preserve moisture, moistureproof and the two-way or compound humectant of the fragrant effect of slowly-releasing material is arranged simultaneously, humectation performance and the international competitiveness that improves China's cigarette product had important practical significance.
Summary of the invention
The object of the present invention is to provide a kind of five carbon monose or six carbon monose-L-ethoxyacetic acid in Meng monoester class compound.
Second purpose of the present invention is to disclose the preparation method of such five carbon or six carbon monose-L-ethoxyacetic acid in Meng monoester class compound.
The 3rd purpose of the present invention is to disclose the purposes of such five carbon or six carbon monose-L-ethoxyacetic acid in Meng monoester class compound.
The object of the present invention is achieved like this:
A kind of five carbon or six carbon monose-L-ethoxyacetic acid in Meng monoester class compound with following general formula:
Wherein, R represents the residue of five carbon monose or six carbon monose; Above-mentioned five carbon monose are preferably from wood sugar, ribose, pectinose, lyxose, ribulose or xylulose, six carbon monose are preferably from glucose, semi-lactosi, seminose, sorbose, gulose, fructose, N.F,USP MANNITOL, sorbyl alcohol, 1,4-anhydrous sorbitol or 3, the 6-anhydrous sorbitol.
Second purpose of the present invention is achieved in that
The preparation method of a kind of five carbon as claimed in claim 1 or six carbon monose-L-ethoxyacetic acid in Meng monoester class compound comprises the steps:
In starting raw material L-ethoxyacetic acid in the Meng and five carbon monose or six carbon monose adding solvent, under the catalyzer existence condition, add condensing agent and carry out condensation reaction, after reaction for some time, through aftertreatment, make L-ethoxyacetic acid in the Meng monoesters and the polyesters mixture of corresponding five carbon or six carbon monose, gained monoesters and polyesters mixture promptly get five carbon or six carbon monose-L-ethoxyacetic acid in Meng monoester class compound accordingly through recrystallization or column chromatography purification.
Its concrete preparation method is described below:
Molar feed ratio when L-ethoxyacetic acid in the Meng and five carbon monose or the reaction of six carbon monose compound condensations is 1.0 ﹕ 0.2～10.0, and preferred molar feed ratio is 1.0 ﹕ 1.0～3.0.
Solvent for use is during condensation reaction: ether solvent (ether, isopropyl ether or methyl tertiary butyl ether), sherwood oil, normal heptane, tetrahydrofuran (THF),
N,
N-dimethyl formamide,
N-methyl-2-pyrrolidone, dimethyl sulfoxide (DMSO), water, ethyl acetate, isopropyl acetate, methylene dichloride, chloroform, C
3～C
8Aliphatic ketone, benzene, toluene or pyridine, preferred solvent be tetrahydrofuran (THF),
N,
N-dimethyl formamide, methylene dichloride, ethyl acetate or pyridine.
Catalyst system therefor is during condensation reaction: the 4-Dimethylamino pyridine; The molar feed ratio of catalyzer and L-ethoxyacetic acid in the Meng is 0.01～1.0 ﹕ 1.0, and preferred molar feed ratio is 0.05～0.3 ﹕ 1.0.
Used condensing agent is during condensation reaction: chloro-formic ester class (methyl-chloroformate, Vinyl chloroformate or isopropyl chlorocarbonate), dicyclohexylcarbodiimide (DCC), 1-ethyl-3-(3-dimethylamine propyl) carbodiimide hydrochloride (EDCI), phosphinylidyne diimidazole (CDI), N-ethoxycarbonyl-2-oxyethyl group-1,2-dihydroquinoline (EEDQ), diethyl phosphorocyanidate (DEPC), 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT) or chlorination 4-(4,6-dimethoxy-1,3,5-triazine-2-yl)-4-methylmorpholine salt (DMTMM).
The molar feed ratio of used condensing agent and L-ethoxyacetic acid in the Meng is 1.0～5.0 ﹕ 1.0, and preferred molar feed ratio is 1.0～2.0 ﹕ 1.0.
Setting-up point is-10 ℃～130 ℃, and preferable reaction temperature is 0～50 ℃; Condensation reaction time is 20 minutes～48 hours, and the preferred reaction time is 1～24 hour.
The 3rd purpose of the present invention is achieved in that
Five carbon disclosed in this invention or six carbon monose-L-ethoxyacetic acid in Meng monoester class compound can be used as tobacco humectant; because this class wetting Agent for Printing Inks has certain water-soluble and fat-soluble simultaneously; can stablize the cigarette water ratio by the bilayer protective membrane of being separated by, reach the effect of humectation, protection against the tide and slowly-releasing material perfume (or spice) at tobacco surface formation profit.
Compared with prior art, beneficial effect of the present invention is as follows:
1, five carbon disclosed in this invention or six carbon monose-L-ethoxyacetic acid in Meng monoesters class tobacco humectant can have simultaneously by form the bilayer protective membrane that profit is separated by on tobacco surface and preserves moisture and moistureproof two kinds of effects; the tobacco of handling through this class humectant dries out very slow in the exsiccant climatope; and it is also very slow to absorb moisture in the climatope of humidity, can effectively slow down the variation of tobacco moisture with envrionment conditions.
2, five carbon disclosed in this invention or six carbon monose-L-ethoxyacetic acid in Meng monoesters class tobacco humectant also can be separated by the bilayer protective membrane and the volatilization that significantly slow down flavour ingredient in the tobacco by the profit that forms on tobacco surface, thereby has the fragrant effect of certain slowly-releasing material.
3, five carbon disclosed in this invention or six carbon monose-own British plain spirits of L-ethoxyacetic acid in Meng monoesters class tobacco humectant, but but thermo-cracking or degraded produce flavour ingredient in aspiration procedure, make the more comfortable harmony of fragrance of cigarette, and these flavour ingredients itself promptly are present in the tobacco, just content is lower, therefore, this class tobacco humectant free from extraneous odour disclosed in this invention is good with the consistency of tobacco.
4, compare with widely used propylene glycol or glycerine on the present tobacco industry, product toxicological harmless after five carbon disclosed in this invention or six carbon monose-L-ethoxyacetic acid in Meng monoesters class tobacco humectant burning, safe in utilization, more help the security of sucking of tobacco, be easy to apply.
Embodiment
Can further describe the present invention by the following examples, yet scope of the present invention is not limited to following embodiment.One of skill in the art can understand, and under the prerequisite that does not deviate from the spirit and scope of the present invention, can carry out various variations and modification to the present invention.
Embodiment 1:
The preparation of 6-(L-ethoxyacetic acid in the Meng)-D-glucopyanosyl ester (Compound I):
In reaction flask, add D-glucose 18.0g(0.1 mol successively), L-ethoxyacetic acid in Meng 25.72g(0.12 mol) and pyridine 200 ml, stirring at room is to the solid dissolving, add 4-Dimethylamino pyridine 2.46g(0.02 mol), after reaction solution is cooled to 0～5 ℃, add dicyclohexylcarbodiimide 26.83g(0.13 mol), 0～5 ℃ is continued stirring reaction 30min, naturally be warming up to stirring at room reaction 18h then, after reaction finishes, remove solvent under reduced pressure, resistates is dissolved among ethyl acetate 200 ml, solid is separated out in filtration, filtrate is used 10% aqueous hydrochloric acid, 50 ml successively, saturated aqueous sodium carbonate 50 ml and saturated aqueous common salt 50 ml washing, the gained ethyl acetate solution is through anhydrous Na
2SO
4Drying is filtered, and removes ethyl acetate under reduced pressure, get L-ethoxyacetic acid in the Meng monoesters and the polyesters mixture of glucose, this mixture gets 6-(L-ethoxyacetic acid in the Meng)-D-glucopyanosyl ester 25.2 g, yield 67.0% through purification by silica gel column chromatography (elutriant is: Lv Fang ﹕ methyl alcohol=10 ﹕ 1); HR-TOFMS (+Q)
M/z: 377.2170 ([C
18H
32O
8+ H]
+Calculated value: 377.2175).
Embodiment 2:
The preparation of 6-(L-ethoxyacetic acid in the Meng)-D-gala pyrans sugar ester (Compound I I):
Operating process just substitutes D-glucose with embodiment 1 with the D-semi-lactosi, dicyclohexylcarbodiimide substitutes with 1-ethyl-3-(3-dimethylamine propyl) carbodiimide hydrochloride, and pyridine is used
N,
N-dimethyl formamide substitutes, and gets 6-(L-ethoxyacetic acid in the Meng)-D-gala pyrans sugar ester, yield 63.5%; HR-TOFMS (+Q)
M/z: 377.2183 ([C
18H
32O
8+ H]
+Calculated value: 377.2175).
Embodiment 3:
The preparation of 6-(L-ethoxyacetic acid in the Meng)-D-mannopyranose ester (compound III):
Operating process is that D-glucose is substituted with the D-seminose with embodiment 1, and dicyclohexylcarbodiimide substitutes with N-ethoxycarbonyl-2-oxyethyl group-1,2-dihydroquinoline, gets 6-(L-ethoxyacetic acid in the Meng)-D-mannopyranose ester, yield 52.7%; HR-TOFMS (+Q)
M/z: 377.2178 ([C
18H
32O
8+ H]
+Calculated value: 377.2175).
Embodiment 4:
The preparation of 1-(L-ethoxyacetic acid in the Meng)-D-sorb pyrans sugar ester (compound IV):
Operating process just uses the D-sorbose to substitute D-glucose with embodiment 1, and dicyclohexylcarbodiimide substitutes with the phosphinylidyne diimidazole, and pyridine substitutes with methylene dichloride, gets 1-(L-ethoxyacetic acid in the Meng)-D-sorb pyrans sugar ester, yield 50.0%; HR-TOFMS (+Q)
M/z: 377.2168 ([C
18H
32O
8+ H]
+Calculated value: 377.2175).
Embodiment 5:
The preparation of 1-(L-ethoxyacetic acid in the Meng)-D-fruit pyrans sugar ester (compound V)
Operating process just substitutes D-glucose with embodiment 1 with D-fructose, dicyclohexylcarbodiimide substitutes with methyl-chloroformate, gets 1-(L-ethoxyacetic acid in the Meng)-D-fruit pyrans sugar ester, yield 59.0%; HR-TOFMS (+Q)
M/z: 399.2003 ([C
18H
32O
8+ Na]
+Calculated value: 399.1995).
Embodiment 6:
The preparation of the ancient Lip river pyrans sugar ester of 6-(L-ethoxyacetic acid in the Meng)-D-(compound VI):
Operating process just substitutes D-glucose with embodiment 1 with the D-gulose, get the ancient Lip river of 6-(L-ethoxyacetic acid in the Meng)-D-pyrans sugar ester, yield 51.1%; HR-TOFMS (+Q)
M/z: 377.2170 ([C
18H
32O
8+ H]
+Calculated value: 377.2175).
Embodiment 7:
The preparation of 1-(L-ethoxyacetic acid in the Meng)-Nitranitol (compound VI I):
Operating process just substitutes D-glucose with embodiment 1 with N.F,USP MANNITOL, get 1-(L-ethoxyacetic acid in the Meng)-Nitranitol, yield 52.8%; HR-TOFMS (+Q)
M/z: 379.2330 ([C
18H
34O
8+ H]
+Calculated value: 379.2332).
Embodiment 8:
The preparation of 1-(L-ethoxyacetic acid in the Meng)-sorbitol ester (compound VIII):
Operating process just substitutes D-glucose with embodiment 1 with sorbyl alcohol, get 1-(L-ethoxyacetic acid in the Meng)-sorbitol ester, yield 59.0%; HR-TOFMS (+Q)
M/z: 379.2338 ([C
18H
34O
8+ H]
+Calculated value: 379.2332).
Embodiment 9:
6-(L-ethoxyacetic acid in the Meng)-1, the preparation of 4-sorbitan ester (Compound I X):
Operating process is with embodiment 1, just with D-glucose with 1, the 4-anhydrous sorbitol substitutes, must 6-(L-ethoxyacetic acid in the Meng)-1,4-sorbitan ester, yield 80.2%; HR-TOFMS (+Q)
M/z: 361.2220 ([C
18H
32O
7+ H]
+Calculated value: 361.2226).
Embodiment 10:
1-(L-ethoxyacetic acid in the Meng)-3, the preparation of 6-sorbitan ester (compounds X):
Operating process is with embodiment 1, just with D-glucose with 3, the 6-anhydrous sorbitol substitutes, must 1-(L-ethoxyacetic acid in the Meng)-3,6-sorbitan ester, yield 80.0%; HR-TOFMS (+Q)
M/z: 361.2229 ([C
18H
32O
7+ H]
+Calculated value: 361.2226).
Embodiment 11:
The preparation of 5-(L-ethoxyacetic acid in the Meng)-D-wood furans sugar ester (compounds X I):
Operating process is that D-glucose is substituted with the D-wood sugar with embodiment 1, and dicyclohexylcarbodiimide substitutes with Vinyl chloroformate, and pyridine substitutes with dimethyl sulfoxide (DMSO), gets 5-(L-ethoxyacetic acid in the Meng)-D-wood furans sugar ester, yield 55.2%; HR-TOFMS (+Q)
M/z: 369.1882 ([C
17H
30O
7+ Na]
+Calculated value: 369.1889).
Embodiment 12:
The preparation of 5-(L-ethoxyacetic acid in the Meng)-D-nuclear furans sugar ester (compounds X II):
Operating process just substitutes D-glucose with embodiment 1 with D-ribose, dicyclohexylcarbodiimide substitutes with isopropyl chlorocarbonate, gets 5-(L-ethoxyacetic acid in the Meng)-D-nuclear furans sugar ester, yield 53.0%; HR-TOFMS (+Q)
M/z: 369.1885 ([C
17H
30O
7+ Na]
+Calculated value: 369.1889).
Embodiment 13:
The preparation of 5-(L-ethoxyacetic acid in the Meng)-D-arbinofuranose ester (compounds X III):
Operating process just substitutes D-glucose with embodiment 1 with the D-pectinose, dicyclohexylcarbodiimide substitutes with diethyl phosphorocyanidate, gets 5-(L-ethoxyacetic acid in the Meng)-D-arbinofuranose ester, yield 50.2%; HR-TOFMS (+Q)
M/z: 347.2080 ([C
17H
30O
7+ H]
+Calculated value: 347.2070).
Embodiment 14:
The preparation of 5-(L-ethoxyacetic acid in the Meng)-D-lysol furans sugar ester (compounds X IV):
Operating process just substitutes D-glucose with embodiment 1 with the D-lyxose, get 5-(L-ethoxyacetic acid in the Meng)-D-lysol furans sugar ester, yield 55.5%; HR-TOFMS (+Q)
M/z: 347.2073 ([C
17H
30O
7+ H]
+Calculated value: 347.2070).
Embodiment 15:
The preparation of 1-(L-ethoxyacetic acid in the Meng)-D-ribulose ester (compounds X V):
Operating process just substitutes D-glucose with embodiment 1 with the D-ribulose, dicyclohexylcarbodiimide substitutes with chlorination 4-(4,6-dimethoxy-1,3,5-triazines-2-yl)-4-methylmorpholine salt, and pyridine is used
N,
N-dimethyl formamide substitutes, and gets 1-(L-ethoxyacetic acid in the Meng)-D-ribulose ester, yield 46.3%; HR-TOFMS (+Q)
M/z: 347.2062 ([C
17H
30O
7+ H]
+Calculated value: 347.2070).
Embodiment 16:
The preparation of 1-(L-ethoxyacetic acid in the Meng)-D-xylulose ester (compounds X VI):
Operating process just substitutes D-glucose with embodiment 1 with the D-xylulose, get 1-(L-ethoxyacetic acid in the Meng)-D-xylulose ester, yield 47.0%; HR-TOFMS (+Q)
M/z: 347.2066 ([C
17H
30O
7+ H]
+Calculated value: 347.2070).
Embodiment 17:
The effect test of humectation, protection against the tide and slowly-releasing material perfume (or spice):
For five carbon disclosed in this invention or six carbon monose-L-ethoxyacetic acid in Meng monoester class compound (Compound I ~ XVI), estimate the fragrant effect of its humectation, protection against the tide and slowly-releasing material with the following method.
(1) humectation and moisture-proof role test
Tobacco sample with the adding propylene glycol is contrast, to above-mentioned five carbon or six carbon monose-L-ethoxyacetic acid in Meng monoester class compound (Compound I～XVI) the humectation effect of pipe tobacco has been carried out the experiment contrast.Propylene glycol and above-mentioned monose monoester class compound solution are added respectively in the pipe tobacco (consumption of humectant be pipe tobacco weight 0.05～1%); Tobacco sample after will handling then places four climatic chambers (four conditions are respectively: 10 ℃ of temperature and relative humidity 40%, 30 ℃ of temperature and relative humidity 40%, 10 ℃ of temperature and relative humidity 80%, 30 ℃ of temperature and relative humidity 80%) that condition is different respectively, every 24h weighs 1 time, weigh altogether 6 times, calculate the water ratio of pipe tobacco respectively.
Test result shows, (Compound I～XVI) all has humectation and moisture-proof role in various degree to five carbon or six carbon monose-L-ethoxyacetic acid in Meng monoester class compound, and its effect is better than the propylene glycol control group.
(2) the fragrant effect test of slowly-releasing material
Tobacco sample with the adding propylene glycol is contrast, to above-mentioned five carbon or six carbon monose-L-ethoxyacetic acid in Meng monoester class compound (Compound I～XVI) the fragrant effect of slowly-releasing material of pipe tobacco has been carried out the experiment contrast.Propylene glycol and above-mentioned monose monoester class compound solution are added respectively in the pipe tobacco (consumption of humectant be pipe tobacco weight 0.05～1%); After various tobacco sample were all placed certain hour, each 0.5 gram of sampling was that solvent carries out supersound extraction with the methylene dichloride respectively; Dichloromethane solution after the extraction utilizes gas chromatograph-mass spectrometer to analyze the content of flavor matter in the filtrate behind filtering with microporous membrane.
Test result shows, the content of typical flavor matter all is higher than the tobacco sample that propylene glycol was handled to some extent in the tobacco sample that above-mentioned monose monoester class compound was handled, and shows that five carbon disclosed in this invention or six carbon monose-L-ethoxyacetic acid in Meng monoester class compound has certain flavour ingredient evaporable effect in the pipe tobacco that slows down.
Claims (10)
1. five carbon or six carbon monose-L-ethoxyacetic acid in Meng monoester class compound with following general formula:
Wherein, R represents the residue of five carbon monose or six carbon monose; Above-mentioned five carbon monose are preferably from wood sugar, ribose, pectinose, lyxose, ribulose or xylulose; Six carbon monose are preferably from glucose, semi-lactosi, seminose, sorbose, gulose, fructose, N.F,USP MANNITOL, sorbyl alcohol, 1,4-anhydrous sorbitol or 3,6-anhydrous sorbitol.
2. the preparation method of five carbon as claimed in claim 1 or six carbon monose-L-ethoxyacetic acid in Meng monoester class compound is characterized in that, comprises the steps:
In starting raw material L-ethoxyacetic acid in the Meng and five carbon monose or six carbon monose adding solvent, under the catalyzer condition, add condensing agent and carry out condensation reaction, after reaction for some time, through aftertreatment, make L-ethoxyacetic acid in the Meng monoesters and the polyesters mixture of corresponding five carbon or six carbon monose, gained monoesters and polyesters mixture promptly get five carbon or six carbon monose-L-ethoxyacetic acid in Meng monoester class compound accordingly through recrystallization or column chromatography purification;
Solvent for use is during condensation reaction: ether solvent, sherwood oil, normal heptane, tetrahydrofuran (THF),
N,
N-dimethyl formamide,
N-methyl-2-pyrrolidone, dimethyl sulfoxide (DMSO), water, ethyl acetate, isopropyl acetate, methylene dichloride, chloroform, C
3～C
8Aliphatic ketone, benzene, toluene or pyridine;
Catalyst system therefor is during condensation reaction: the 4-Dimethylamino pyridine;
Used condensing agent is during condensation reaction: chloro-formic ester class, dicyclohexylcarbodiimide, 1-ethyl-3-(3-dimethylamine propyl) carbodiimide hydrochloride, phosphinylidyne diimidazole, N-ethoxycarbonyl-2-oxyethyl group-1,2-dihydroquinoline, diethyl phosphorocyanidate, 2-chloro-4,6-dimethoxy-1,3,5-triazine or chlorination 4-(4,6-dimethoxy-1,3,5-triazines-2-yl)-4-methylmorpholine salt.
3. the preparation method of five carbon as claimed in claim 2 or six carbon monose-L-ethoxyacetic acid in Meng monoester class compound is characterized in that, described condensation reaction solvent for use be preferably tetrahydrofuran (THF),
N,
N-dimethyl formamide, methylene dichloride, ethyl acetate or pyridine.
4. the preparation method of five carbon as claimed in claim 2 or six carbon monose-L-ethoxyacetic acid in Meng monoester class compound, it is characterized in that the molar feed ratio when described L-ethoxyacetic acid in the Meng and five carbon monose or the reaction of six carbon monose compound condensations is 1.0 ﹕ 0.2～10.0.
5. the preparation method of five carbon as claimed in claim 4 or six carbon monose-L-ethoxyacetic acid in Meng monoester class compound, it is characterized in that the molar feed ratio when described L-ethoxyacetic acid in the Meng and five carbon monose or the reaction of six carbon monose compound condensations is preferably 1.0 ﹕ 1.0～3.0.
6. the preparation method of five carbon as claimed in claim 2 or six carbon monose-L-ethoxyacetic acid in Meng monoester class compound is characterized in that the molar feed ratio of condensing agent and L-ethoxyacetic acid in the Meng is 1.0～5.0 ﹕ 1.0 in the described condensation reaction.
7. the preparation method of five carbon as claimed in claim 6 or six carbon monose-L-ethoxyacetic acid in Meng monoester class compound is characterized in that the molar feed ratio of condensing agent and L-ethoxyacetic acid in the Meng is preferably 1.0～2.0 ﹕ 1.0 in the described condensation reaction.
8. the preparation method of five carbon as claimed in claim 2 or six carbon monose-L-ethoxyacetic acid in Meng monoester class compound is characterized in that the molar feed ratio of catalyzer and L-ethoxyacetic acid in the Meng is 0.01～1.0 ﹕ 1.0 in the described condensation reaction; Setting-up point is-10 ℃～130 ℃; Condensation reaction time is 20 minutes～48 hours.
9. the preparation method of five carbon as claimed in claim 8 or six carbon monose-L-ethoxyacetic acid in Meng monoester class compound is characterized in that the molar feed ratio of catalyzer and L-ethoxyacetic acid in the Meng is preferably 0.05～0.3 ﹕ 1.0 in the described condensation reaction; Setting-up point is preferably 0～50 ℃; Condensation reaction time is preferably 1～24 hour.
10. five carbon as claimed in claim 1 or six carbon monose-L-ethoxyacetic acid in Meng monoester class compound are as the application of tobacco humectant.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 201010524908 CN101974040B (en) | 2010-10-29 | 2010-10-29 | Five-carbon or six-carbon monosaccharide-L-menthoxyacetyl acid monoester compound as well as preparation method and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 201010524908 CN101974040B (en) | 2010-10-29 | 2010-10-29 | Five-carbon or six-carbon monosaccharide-L-menthoxyacetyl acid monoester compound as well as preparation method and application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101974040A true CN101974040A (en) | 2011-02-16 |
| CN101974040B CN101974040B (en) | 2013-01-30 |
Family
ID=43573957
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 201010524908 Expired - Fee Related CN101974040B (en) | 2010-10-29 | 2010-10-29 | Five-carbon or six-carbon monosaccharide-L-menthoxyacetyl acid monoester compound as well as preparation method and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN101974040B (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102304154A (en) * | 2011-09-05 | 2012-01-04 | 川渝中烟工业公司 | Monosaccharide alpha-ionol carbonic acid monoester compounds and preparation method and use thereof |
| CN102311465A (en) * | 2011-09-05 | 2012-01-11 | 川渝中烟工业公司 | Monosaccharide geraniol carbonate monoester compound and preparation method and application thereof |
| CN102311464A (en) * | 2011-09-05 | 2012-01-11 | 川渝中烟工业公司 | Monomenthyloxycarbonyl monosugar ester compounds, preparation method thereof and purpose thereof |
| CN102336789A (en) * | 2011-09-05 | 2012-02-01 | 川渝中烟工业有限责任公司 | Monosaccharide beta-ionol carbonic acid monoester compound, and preparation method and purpose |
| CN102702275A (en) * | 2012-05-23 | 2012-10-03 | 河南中烟工业有限责任公司 | Novel humectant for tobacco and preparation method of humectant |
| CN102875611A (en) * | 2012-09-07 | 2013-01-16 | 河南中烟工业有限责任公司 | Humectants 1-O-carboxymethyl-D-furan mannose for cigarettes and preparation method of humectants 1-O-carboxymethyl-D-furan mannose |
| CN106854225A (en) * | 2016-12-14 | 2017-06-16 | 盐城市春竹香料有限公司 | A kind of preparation method and applications of glucose ester |
| 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 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0069512A2 (en) * | 1981-07-08 | 1983-01-12 | Pfizer Inc. | Salts of N-substituted-2-pyrrolidone-4-carboxylic acids as humectants |
| CN1204482A (en) * | 1998-07-16 | 1999-01-13 | 吕次昌 | Moist-keeping agent for tobacco |
| CN1860126A (en) * | 2003-10-02 | 2006-11-08 | 花王株式会社 | Glycerol carbonate glycoside |
-
2010
- 2010-10-29 CN CN 201010524908 patent/CN101974040B/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0069512A2 (en) * | 1981-07-08 | 1983-01-12 | Pfizer Inc. | Salts of N-substituted-2-pyrrolidone-4-carboxylic acids as humectants |
| CN1204482A (en) * | 1998-07-16 | 1999-01-13 | 吕次昌 | Moist-keeping agent for tobacco |
| CN1860126A (en) * | 2003-10-02 | 2006-11-08 | 花王株式会社 | Glycerol carbonate glycoside |
Non-Patent Citations (1)
| Title |
|---|
| 《CHEM ABSTRACT》 19591231 Nielsen, Jorgen Tormod等 cis- and trans-2,5-Dimethoxy-2,5-dihydrofuran 全文 1-10 第53卷, 第6966期 * |
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102336789B (en) * | 2011-09-05 | 2014-02-26 | 川渝中烟工业有限责任公司 | Monosaccharide beta-ionol carbonic acid monoester compound, and preparation method and purpose |
| CN102311464B (en) * | 2011-09-05 | 2014-03-26 | 川渝中烟工业有限责任公司 | Monomenthyloxycarbonyl monosugar ester compounds, preparation method thereof and purpose thereof |
| CN102311464A (en) * | 2011-09-05 | 2012-01-11 | 川渝中烟工业公司 | Monomenthyloxycarbonyl monosugar ester compounds, preparation method thereof and purpose thereof |
| CN102336789A (en) * | 2011-09-05 | 2012-02-01 | 川渝中烟工业有限责任公司 | Monosaccharide beta-ionol carbonic acid monoester compound, and preparation method and purpose |
| CN102311465B (en) * | 2011-09-05 | 2014-02-26 | 川渝中烟工业有限责任公司 | Monosaccharide geraniol carbonate monoester compound and preparation method and application thereof |
| CN102304154B (en) * | 2011-09-05 | 2014-05-07 | 川渝中烟工业有限责任公司 | Monosaccharide alpha-ionol carbonic acid monoester compounds and preparation method and use thereof |
| CN102311465A (en) * | 2011-09-05 | 2012-01-11 | 川渝中烟工业公司 | Monosaccharide geraniol carbonate monoester compound and preparation method and application thereof |
| CN102304154A (en) * | 2011-09-05 | 2012-01-04 | 川渝中烟工业公司 | Monosaccharide alpha-ionol carbonic acid monoester compounds and preparation method and use thereof |
| CN102702275B (en) * | 2012-05-23 | 2014-06-18 | 河南中烟工业有限责任公司 | Novel humectant for tobacco and preparation method of humectant |
| CN102702275A (en) * | 2012-05-23 | 2012-10-03 | 河南中烟工业有限责任公司 | Novel humectant for tobacco and preparation method of humectant |
| CN102875611A (en) * | 2012-09-07 | 2013-01-16 | 河南中烟工业有限责任公司 | Humectants 1-O-carboxymethyl-D-furan mannose for cigarettes and preparation method of humectants 1-O-carboxymethyl-D-furan mannose |
| CN102875611B (en) * | 2012-09-07 | 2014-12-10 | 河南中烟工业有限责任公司 | Humectants 1-O-carboxymethyl-D-furan mannose for cigarettes and preparation method of humectants 1-O-carboxymethyl-D-furan mannose |
| CN106854225A (en) * | 2016-12-14 | 2017-06-16 | 盐城市春竹香料有限公司 | A kind of preparation method and applications of glucose ester |
| 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN101974040B (en) | 2013-01-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN101974040B (en) | Five-carbon or six-carbon monosaccharide-L-menthoxyacetyl acid monoester compound as well as preparation method and application thereof | |
| CN102311465B (en) | Monosaccharide geraniol carbonate monoester compound and preparation method and application thereof | |
| CN102304155B (en) | Monosaccharide geraniol carbonate diester compound, preparation method and use thereof | |
| CN102304154B (en) | Monosaccharide alpha-ionol carbonic acid monoester compounds and preparation method and use thereof | |
| CN101974042B (en) | Mono-pentose or hexose-(E)-3-(furan-2-yl) acrylic acid diester compound and preparation method and use thereof | |
| CN101974039B (en) | C5 or C6 monosaccharide-(E)-3-(furyl-2-yl) monoacrylate compound, preparation method and application thereof | |
| CN102311464B (en) | Monomenthyloxycarbonyl monosugar ester compounds, preparation method thereof and purpose thereof | |
| CN102286035A (en) | Bimenthoxycarbonylmonose ester compound as well as preparation method and application thereof | |
| US10966452B2 (en) | Tobacco humectant, preparation method and use thereof | |
| BR112013014799B1 (en) | method of preparing an alkyl-substituted amino furan compound | |
| CN108211417B (en) | Preparation method and application of extraction auxiliary substance for extracting flavone from plant | |
| CN101974041A (en) | Five-carbon/five-carbon monosaccharide-L-menthoxyacetic acid diester compound and preparation method and application thereof | |
| CN102336789B (en) | Monosaccharide beta-ionol carbonic acid monoester compound, and preparation method and purpose | |
| JP5295744B2 (en) | Method for producing theacinensin | |
| CN102286034B (en) | Monosaccharide alpha-ionol carbonic acid di-ester compound as well as preparation method and application thereof | |
| JP2010070468A5 (en) | ||
| CN102286033B (en) | Monosaccharide beta-ionol carbonate diester compound as well as preparation method and application thereof | |
| CN102532075B (en) | Aurone compounds in nicotiana tabacum and application thereof | |
| CN107212460B (en) | The natural eutectic solvent humectant for smoke of lemon acid type and its application in cigarette | |
| CN104173220B (en) | Armeniaca mume extract is used as the new application of anti-carbonylation active ingredient | |
| JP4308714B2 (en) | Process for producing natural product-derived glyceroglycolipid | |
| Wolfrom et al. | Action of Heat on D-Fructose. III. 1 Interconversion to D-Glucose | |
| CN116462723A (en) | Furfuryl mercaptan glycoside derivative and preparation method and application thereof | |
| CN108516998A (en) | A kind of preparation method and application of coke sweet tea fragrance emitting agent for cigarettes active ingredient | |
| JP2000336355A (en) | Antioxidant |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C53 | Correction of patent for invention or patent application | ||
| CB03 | Change of inventor or designer information |
Inventor after: Dai Ya Inventor after: Shen Yi Inventor after: Zhou Rong Inventor after: Sun Yufeng Inventor after: Li Dongliang Inventor after: Wang Changguo Inventor after: Ma Kuoyan Inventor before: Dai Ya Inventor before: Shen Yi Inventor before: Ma Kuoyan Inventor before: Zhou Rong |
|
| COR | Change of bibliographic data |
Free format text: CORRECT: INVENTOR; FROM: DAI YA SHEN YI MA KUOYAN ZHOU RONG TO: DAI YA SHEN YI ZHOU RONG SUN YUFENG LI DONGLIANG WANG ZHANGGUO MA KUOYAN |
|
| C53 | Correction of patent for invention or patent application | ||
| CB02 | Change of applicant information |
Address after: 610017 Jackie Chan Road, Chengdu economic and Technological Development Zone, Longquanyi District, Sichuan, China, No. 2, No. Applicant after: China Tobacco Chuanyu Industrial Co., Ltd. Address before: 610017 Jackie Chan Road, Chengdu economic and Technological Development Zone, Longquanyi District, Sichuan, China, No. 2, No. Applicant before: China Tobacco Chuanyu Industrial Corporation |
|
| COR | Change of bibliographic data |
Free format text: CORRECT: APPLICANT; FROM: CHINA TOBACCO CHUANYU INDUSTRIAL CORPORATION TO: CHINA TOBACCO CHUANYU INDUSTRIAL CO., LTD. |
|
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| C41 | Transfer of patent application or patent right or utility model | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20170111 Address after: Nanping Nan'an District of Chongqing City Road 400060 No. 2 Patentee after: CHONGQING CHINA TOBACCO INDUSTRIAL CO., LTD. Patentee after: CHINA TOBACCO SICHUAN INDUSTRIAL CO., LTD. Address before: 610017 Jackie Chan Road, Chengdu economic and Technological Development Zone, Longquanyi District, Sichuan, China, No. 2, No. Patentee before: China Tobacco Chuanyu Industry Co., Ltd. |
|
| CF01 | Termination of patent right due to non-payment of annual fee | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20130130 Termination date: 20171029 |