Unlock instant, AI-driven research and patent intelligence for your innovation.

Five-carbon or six-carbon monosaccharide-L-menthoxyacetyl acid monoester compound as well as preparation method and application thereof

A six-carbon monosaccharide and acetic acid monoester technology, which is applied in the field of monosaccharide monoester tobacco humectants, five-carbon or six-carbon monosaccharide-L-menthoxyacetic acid monoester compounds, and can solve the problem of water content in finished cigarettes The effect of smoking comfort is not really satisfactory, the dryness and irritation are enhanced, and the influence of tobacco is greater, so as to achieve the effects of smoking safety, comfortable and harmonious aroma, and easy promotion and application

Inactive Publication Date: 2013-01-30
CHONGQING CHINA TOBACCO IND CO LTD +1
View PDF4 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the humectants used in the production of cigarettes in my country are mainly glycerin, propylene glycol, xylitol and other polyhydroxy substances, which mainly rely on their absorption of moisture in the environment to keep the shredded tobacco moist and play a moisturizing role, which belongs to one-way moisturizing Although this kind of humectant can maintain the moisture content of cut tobacco during processing and improve the processing resistance of cut tobacco, its effect of maintaining the moisture content of finished cigarettes and improving smoking comfort is not really satisfactory
In addition, since this type of polyhydric humectant has no moisture-proof effect, the moisture content of tobacco treated with this type of humectant is greatly affected by the ambient temperature and humidity, that is, in a dry environment, tobacco is easy to lose moisture and cause it to dry. The sensation and irritation are enhanced, and tobacco is easy to absorb moisture in a humid and warm environment, causing it to mold and deteriorate

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Five-carbon or six-carbon monosaccharide-L-menthoxyacetyl acid monoester compound as well as preparation method and application thereof
  • Five-carbon or six-carbon monosaccharide-L-menthoxyacetyl acid monoester compound as well as preparation method and application thereof
  • Five-carbon or six-carbon monosaccharide-L-menthoxyacetyl acid monoester compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Preparation of 6-(L-menthoxyacetic acid)-D-glucopyranosyl ester (compound I):

[0031] Add 18.0 g (0.1 mol) of D-glucose, 25.72 g (0.12 mol) of L-menthoxyacetic acid and 200 ml of pyridine in sequence in the reaction flask, stir at room temperature until the solid dissolves, then add 2.46 g of 4-dimethylaminopyridine ( 0.02 mol), after cooling the reaction liquid to 0-5°C, add 26.83g (0.13 mol) of dicyclohexylcarbodiimide, continue to stir and react for 30min at 0-5°C, then naturally warm up to room temperature and stir for 18h, the reaction ends Afterwards, the solvent was evaporated under reduced pressure, the residue was dissolved in 200 ml of ethyl acetate, and the solid was precipitated by filtration. The filtrate was washed successively with 50 ml of 10% aqueous hydrochloric acid solution, 50 ml of saturated aqueous sodium carbonate solution and 50 ml of saturated brine to obtain acetic acid Ethyl ester solution over anhydrous Na 2 SO 4 Dry, filter, and evaporat...

Embodiment 2

[0033] Preparation of 6-(L-menthoxyacetic acid)-D-galactopyranosyl ester (compound II):

[0034] The operation process is the same as in Example 1, except that D-glucose is replaced with D-galactose, and dicyclohexylcarbodiimide is 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride Substitute for pyridine N , N -Dimethylformamide was substituted to obtain 6-(L-menthoxyacetic acid)-D-galactopyranosyl ester with a yield of 63.5%; HR-TOFMS (+Q) m / z : 377.2183 ( [C 18 h 32 o 8 +H] + Calculated value: 377.2175 ).

Embodiment 3

[0036] Preparation of 6-(L-menthoxyacetic acid)-D-mannopyranosyl ester (compound III):

[0037] The operation process is the same as in Example 1, except that D-glucose is replaced by D-mannose, and dicyclohexylcarbodiimide is replaced by N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline to obtain 6-(L-Mengoxyacetic acid)-D-mannopyranosyl ester, yield 52.7%; HR-TOFMS (+Q) m / z : 377.2178( [C 18 h 32 o 8 +H] + Calculated value: 377.2175 ).

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

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 [0001] The invention belongs to the technical field of tobacco, and relates to a monosaccharide monoester tobacco humectant, in particular to a five-carbon or six-carbon monosaccharide-L-menthoxyacetic acid monoester compound, a preparation method and an application thereof. Background technique [0002] The moisture retention performance of cigarettes is closely related to the quality of cigarettes, and the research on flavor enhancement and moisture retention technology will be one of the main directions of scientific and technological research and technological innovation in my country's tobacco industry in the next few years. At present, the humectants used in the production of cigarettes in my country are mainly glycerin, propylene glycol, xylitol and other polyhydroxy substances, which mainly rely on their absorption of moisture in the environment to keep the shredded tobacco moist and play a moisturizing role, which belongs to one-way moisturizing Altho...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C07H13/04C07H1/00A24B15/40A24B15/34
Inventor 戴亚沈怡周容孙玉峰李东亮汪长国马扩彦
Owner CHONGQING CHINA TOBACCO IND CO LTD