CN107700278B - Cigarette paper additive with effects of returning sweet and moistening throat and application thereof - Google Patents

Cigarette paper additive with effects of returning sweet and moistening throat and application thereof Download PDF

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Publication number
CN107700278B
CN107700278B CN201710767857.XA CN201710767857A CN107700278B CN 107700278 B CN107700278 B CN 107700278B CN 201710767857 A CN201710767857 A CN 201710767857A CN 107700278 B CN107700278 B CN 107700278B
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additive
cigarette paper
rose
cigarette
percent
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CN107700278A (en
Inventor
张承明
孔维松
王晓辉
李雪梅
杨叶昆
倪朝敏
李晶
刘欣
杨光宇
李松
伊奥尔
王迪
李迎华
许健
韩莹
端凯
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China Tobacco Yunnan Industrial Co Ltd
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China Tobacco Yunnan Industrial Co Ltd
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    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
    • D21H21/14—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties characterised by function or properties in or on the paper
    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24D—CIGARS; CIGARETTES; TOBACCO SMOKE FILTERS; MOUTHPIECES FOR CIGARS OR CIGARETTES; MANUFACTURE OF TOBACCO SMOKE FILTERS OR MOUTHPIECES
    • A24D1/00—Cigars; Cigarettes
    • A24D1/02—Cigars; Cigarettes with special covers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
    • C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
    • C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
    • C07D311/30—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only not hydrogenated in the hetero ring, e.g. flavones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
    • C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
    • C07D311/40—Separation, e.g. from natural material; Purification
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
    • D21H17/02—Material of vegetable origin
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
    • D21H17/03—Non-macromolecular organic compounds
    • D21H17/05—Non-macromolecular organic compounds containing elements other than carbon and hydrogen only
    • D21H17/06—Alcohols; Phenols; Ethers; Aldehydes; Ketones; Acetals; Ketals
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
    • D21H17/03—Non-macromolecular organic compounds
    • D21H17/05—Non-macromolecular organic compounds containing elements other than carbon and hydrogen only
    • D21H17/14—Carboxylic acids; Derivatives thereof
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
    • D21H17/20—Macromolecular organic compounds
    • D21H17/21—Macromolecular organic compounds of natural origin; Derivatives thereof
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
    • D21H17/60—Waxes

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Fats And Perfumes (AREA)
  • Cosmetics (AREA)

Abstract

The invention discloses a cigarette paper additive with the effects of returning sweetness and wetting throat and application thereof. Uniformly mixing rose honey, phenethyl alcohol, phenethyl propionate, phenethyl formate, vanillin, ethyl vanillin, rose flavone-U, royal jelly, propylene glycol, beeswax absolute oil, rose essential oil, fructus phyllanthi extract and water to obtain the product. Wherein the rose flavone-U is a new flavonoid compound separated from waste residue after the production of rose essential oil, and has the following structural formula:Is named as: 7- (3-hydroxypropyl) -8, 2' -dimethoxyflavone. In the cigarette paper preparation process, the additive is coated according to 1-2% of the weight of the cigarette paper, so that the sweet feeling of cigarette smoke is obviously enhanced, the smoke is smoother and smoother when passing through the throat, the irritation of the throat is obviously reduced, and the throat comfort of cigarette smoking can be obviously improved. The additive of the invention has less dosage, easy realization of the adding process, small influence on the chemical balance of cigarettes and no obvious change to the style of cigarettes.

Description

Cigarette paper additive with effects of returning sweet and moistening throat and application thereof
Technical Field
the invention belongs to the technical field of cigarette additives, and particularly relates to a cigarette paper additive with the effects of returning sweetness and moistening throat. Meanwhile, the invention also relates to the specific application of the additive in cigarette production.
Background
The cigarette paper is a special thin-leaf paper for wrapping tobacco to make cigarettes, and is characterized in that: the paper is compact, soft and fine, has high opacity, and has high longitudinal tensile strength, certain air permeability and proper burning speed. The preparation process of the cigarette paper mainly comprises the following steps: the bleached hemp pulp is used as main raw material, and a part of bleached wood pulp or straw pulp is mixed, and then the mixture is undergone the processes of high-viscosity pulping, calcium carbonate and small quantity of combustion adjuvant (for coordinating combustion speed of cigarette paper and tobacco shred) are added, and then the above-mentioned materials are made into paper by means of long-net paper-making machine, and finally cut and rolled into disk so as to obtain the invented finished product. The cigarette paper has the functions of wrapping tobacco shreds, adjusting the combustibility of cigarettes, improving cigarette ash, reducing harmful components such as tar, sidestream smoke CO and the like generated in the smoking process of the cigarettes, and can improve the smoking quality of cigarette products, and the function research in the aspect draws more and more attention of scientific researchers.
With the increasing rise of anti-smoking sports in the world, the tobacco industry of various countries reduces the tar content of cigarettes; with the continuous low tar content of cigarettes, the tar can be reduced and the higher smoking quality can be obtained only by developing a cigarette smoking taste compensation technology, so that the quality and the characteristics of the original product can be maintained. Therefore, tobacco enterprises need to develop corresponding cigarette taste compensation technology in the processes of reducing tar and improving the smoking quality of cigarette products. Because the cigarette paper flavoring technology is easy to realize industrialization and has little influence on the chemical balance of cigarettes, the cigarette paper has been widely applied to the tobacco industry for improving the smoking quality of cigarettes. Various new technologies thus developed: the flavoring technology of the inclusion compound, the flavoring technology of the capsule, the flavoring technology of the microporous polymer, the flavoring technology of the ion exchange resin, the flavoring technology of the adsorbent and the like are widely applied, and the functional cigarette paper with different shapes and colors is developed and used for improving the smoking quality of the cigarette.
The Yunnan cigarette product has sufficient and strong fragrance, moderate strength and strong smoking satisfaction. However, compared with the provincial competitive brands, due to the difference of taste preference of consumers, the problems of slightly lack of smoking comfort and slightly exposed irritation and dry feeling exist in part of provincial markets, the smoking quality of the product is urgently needed to be improved, and the development significance of the related technology is great.
Disclosure of Invention
Aiming at the defects of the prior art, the invention provides a cigarette paper additive which is prepared from new flavonoids and has the effects of returning sweet and moistening throat, so as to reduce the throat irritation of smoke and improve the throat comfort of cigarettes during smoking.
The invention also aims to provide the specific application of the additive in the production of cigarette paper.
The purpose of the invention is realized by the following technical scheme.
all percentages used herein are by weight unless otherwise indicated.
A cigarette paper additive with the effects of returning sweet and moistening throat is prepared from the following raw materials in percentage by mass: 9 to 12 percent of rose honey, 0.2 to 0.3 percent of phenethyl alcohol, 0.15 to 0.2 percent of phenethyl propionate, 0.08 to 0.1 percent of phenethyl formate, 0.04 to 0.06 percent of vanillin, 0.1 to 0.15 percent of ethyl vanillin, 0.2 to 0.3 percent of rose flavone-U, 2 to 4 percent of royal jelly, 9 to 12 percent of propylene glycol, 0.8 to 1.2 percent of beeswax absolute, 0.2 to 0.3 percent of rose essential oil, 1.5 to 2 percent of phyllanthus emblica extract and the balance of water; the raw materials are uniformly mixed and fully dissolved to obtain a light yellow transparent solution, namely the required cigarette paper additive.
The additive formula comprises the following components: the propylene glycol is a cosolvent, so that the solubility of each component in the formula can be increased, each component in the formula can be fully dissolved, and trace precipitation and turbidity caused by direct preparation with water are avoided.
Phenethyl alcohol, phenethyl formate, phenethyl propionate, vanillin and ethyl vanillin are monomer perfumes. Phenethyl alcohol has a fresh and sweet rose-like floral aroma; the ethyl benzoate has fresh flower fragrance and fruit fragrance; the ethyl benzene propionate is fragrant and sweet, has fragrance similar to that of red rose, has fruit bottom fragrance, and has flavor similar to that of thick honey and strawberry; vanillin and ethyl vanillin have a strong vanilla flavor and the sweetness taste of sweet chocolate.
the rose honey and royal jelly pyrolysis products are in acid reaction, can play a role in neutralizing alkaline substances in smoke, can reduce the impure gas and the irritation of cigarettes, and can increase the mellow feeling of the smoke of the cigarettes.
The beeswax absolute, the rose essential oil and the fructus phyllanthi extract are natural extracts. The beeswax absolute has mild sweet fragrance and wax fragrance, and has herbal smell similar to coumarin. The rose essential oil has strong rose characteristic sweet fragrance, sweet and full fragrance and thick and elegant bottom. The fructus phyllanthi extract has the effects of clearing heat, relieving sore throat, moistening lung, eliminating phlegm, promoting fluid production and quenching thirst.
The rose flavone-U is a new flavonoid compound separated from waste residue after the production of rose essential oil, and has the following structural formula:
The compound was a pale yellow gum, designated: 7- (3-hydroxypropyl) -8, 2' -dimethoxyflavone, English name: 7- (3-hydroxyproyl) -6, 2' -dimethoxy-flavanone, common name is rose flavone-U. Can obviously increase the sweet feeling of the cigarette smoke and has the functions of promoting the production of body fluid and returning sweet.
The method for preparing the 7- (3-hydroxypropyl) -8, 2' -dimethoxyflavone comprises the following steps:
(1) Sample extraction: ultrasonically extracting waste residues after the production of the rose essential oil for 2-5 times by using a solvent, wherein the weight of the solvent used in each extraction is 2-6 times that of the waste residues, the extraction time is 30-60 minutes each time, combining the extracting solutions, filtering, concentrating the filtrate under reduced pressure until just precipitates, standing for 20-60 minutes, and filtering the precipitates to obtain a sample extracting solution;
(2) MCI decoloration: loading the sample extractive solution on MCI column, collecting eluate, and concentrating under reduced pressure to obtain extract;
(3) Silica gel column chromatography: performing silica gel column chromatography on the extract, wherein the silica gel filled in the column is 160-200 meshes, and the weight of the silica gel is 6-10 times that of the extract; performing gradient elution with chloroform-acetone solution at volume ratio of 20:1,9:1,8:2,7:3,6:4 and 1:1, collecting gradient eluates of each gradient, concentrating, monitoring by TLC, and mixing the same fractions;
(4) High performance liquid chromatography separation: and (3) separating and purifying the eluent obtained by eluting chloroform-acetone with the ratio of 8:2 by adopting high performance liquid chromatography, detecting the wavelength of 358nm by using an ultraviolet detector, collecting chromatographic peaks for 30-45 min, accumulating for multiple times, and evaporating to dryness to obtain the compound.
Further, in the step (1), the solvent is an acetone aqueous solution with a volume concentration of 70-100%, an ethanol aqueous solution with a volume concentration of 70-100% or a methanol aqueous solution with a volume concentration of 70-100%.
In the step (3), before the extract is subjected to silica gel column chromatography, acetone or methanol which is 1.5-3 times of the weight of the extract is used for dissolving the extract, then 80-100 meshes of silica gel which is 0.8-1.2 times of the weight of the extract is used for mixing the sample, and then the sample is loaded.
in the step (3), during gradient elution, no component flows out each time, namely no component remains in the distillation flask after the solvent is evaporated, and then the next gradient is changed.
In the step (4), the high performance liquid chromatography separation and purification uses a methanol aqueous solution with a volume concentration of 45-65% as a mobile phase, the flow rate is 15-25 mL/min, a Zorba xPrepHT GF reversed-phase preparation column with the thickness of 21.2 x 250mm and 5 mu m as a stationary phase, the detection wavelength of an ultraviolet detector is 358nm, 0.5-1.0 mL of sample is injected each time, chromatographic peaks of 38.6min are collected, and the chromatographic peaks are evaporated to dryness after multiple accumulation.
In the cigarette paper preparation process, the additive is coated according to 1-2% of the weight of the cigarette paper, so that the sweet feeling of cigarette smoke is obviously enhanced, the smoke is smoother and smoother when passing through the throat, the irritation of the throat is obviously reduced, and the throat comfort of cigarette smoking can be obviously improved.
the preparation method of the cigarette paper comprises the following steps: defibering, pulping, blending long and short fiber proportion, functional auxiliary agents, adding fillers, and then forming dehydrated paper, wherein after the paper is formed, the additive is added into the formed wet paper in a spraying manner, and the addition amount of the additive is 1-2% of the dry weight of the cigarette paper; and then squeezing, drying, reeling and rewinding to obtain the cigarette paper added with the additive. The cigarette paper is used for preparing cigarettes, the same cigarette paper without the additive is used as a reference, sensory evaluation is carried out according to GB5606.4-2005 standard, and the evaluation result shows that: after the additive is added into cigarette paper, the sweet feeling of cigarette mainstream smoke is obviously enhanced, the smoke is smoother and smoother when passing through the throat, the irritation of the throat is obviously reduced, and the throat comfort of cigarette smoking can be obviously improved.
The invention has the beneficial effects that:
1. The additive is simple to prepare, all the components are uniformly mixed according to a proportion, and the additive has strong sweet fragrance and very outstanding smell and fragrance characteristics. The cigarette paper has an obvious effect when being coated by 1-2% in the preparation process of the cigarette paper, the sweet feeling of cigarette smoke is obviously enhanced, the smoke becomes smooth and fluent when passing through the throat, the irritation of the throat is obviously reduced, and the throat comfort of cigarette smoking can be obviously improved. The problems of slight lack of smoking comfort, slight exposure of irritation and dryness of the cigarettes can be relieved to a certain extent.
2. the additive is added to the cigarette paper in the cigarette paper production process, the adding process is easy to realize, the additive dosage is small, the influence on the cigarette chemical balance by the cigarette paper addition is small, and the cigarette style can not be obviously changed.
3. except for the rose flavone-U, the raw materials of the additive can be purchased from the market, the additive has mature production and supply, and the manufacturing cost of the additive is low.
4. The key component rose flavone-U in the additive is obtained by separating waste residue after the production of rose essential oil, and has wide raw material source and low cost; the compound can comprehensively utilize waste resources and improve the added value of rose processing. The flavonoid has outstanding taste improving effect, has a natural and light aftertaste after being taken, and can make smoke smoother and smoother when passing through the throat.
Drawings
FIG. 1 is the nuclear magnetic resonance carbon spectrum of rose flavone-U of the present invention (13C NMR)；
FIG. 2 shows the NMR spectrum of rose flavone-U of the present invention1H NMR)；
FIG. 3 is a key HMBC correlation chart of the rose flavone-U of the present invention.
Detailed Description
in order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention will be further described in detail with reference to the accompanying drawings and embodiments. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention. The raw materials and equipment used in the examples are commercially available or commonly used in the art, unless otherwise specified, and the methods in the examples are conventional in the art, unless otherwise specified.
Example-1 preparation of the Compound Riboflavone-U
The waste residue sample after producing the rose essential oil comes from Xinjiang Hotan and the variety is Damascus rose. Taking 100kg of waste residue, and ultrasonically extracting with 95% ethanol 300L for 4 times, each time for 30 min. Mixing extractive solutions, and concentrating under reduced pressure to 1/4 of the volume; standing, filtering to remove precipitate, decolorizing the solution after filtering to remove precipitate with MCI column, and concentrating under reduced pressure to obtain 6.8kg extract; 680g of extract is taken, 1.2kg of acetone is added into the extract for dissolution, 900g of 100-mesh silica gel is added for sample mixing, 4.5kg of 200-mesh silica gel is used for loading into a column, and the column is loaded after sample mixing; gradient elution is carried out by chloroform-acetone mixed organic solvent with volume ratio of 20:1,9:1,8:2,7:3,6:4 and 1:1 respectively, gradient eluent is collected and concentrated, TLC monitoring is carried out, the same parts are combined to obtain 6 parts A-F, wherein 183g of the collected part B (8:2) of a sample is taken as a mobile phase, 56% methanol is taken as a mobile phase, the flow rate is 20mL/min, 21.2 x 250mm, 5μm ZorbaxPrepHT GF reversed-phase preparation column is taken as a stationary phase, the detection wavelength of an ultraviolet detector is 358nm, 1.0mL of sample is fed each time, 38.6min chromatographic peaks are collected, and the rose flavone-U compound is obtained after multiple accumulation and evaporation.
Identification of the Structure of the Compound: the structure of the prepared compound was identified by the following method:
HRESI-MS shows that the peak of the excimer ion is 363.1215[ M + Na ]]+(calculated 363.1208), combined1H NMR and DEPT spectra confirm that the molecular formula is C19H18O5The unsaturation degree was 11.
The infrared spectrum shows hydroxyl (3428), carbonyl (1665) and aromatic rings (1618, 1552 and 1463cm-1) The resonance absorption peak of (1). The ultraviolet spectrum has maximum absorption at 210, 256 and 358nmIt also indicates that aromatic ring structures may be present in the compound.
Process for preparing compounds1h and13C NMR spectra (see Table 1, FIG. 1 and FIG. 2) show that they contain 20 carbons and 20 hydrogens, including 1,2,4, 5-tetrasubstituted phenyl ring (C-5 to C-10, H-5, H-6), 1, 2-disubstituted phenyl ring (C-1' to C-6', H-3' to H-6'), 1 α, β -unsaturated carbonyl (C-2, C-3, C-4, H-3), 1 hydroxypropyl (C-1' to C-3 ', H-3 ')2-1″～H2-3 "), two methoxy groups (δ)C56.2q and 55.9q, deltaH3.81s and 3.79 s). The compound is assumed to be a flavonoid compound according to typical 2 benzene rings, alpha, beta-unsaturated carbonyl and double bond signals. The compounds were further confirmed to have flavonoid structures based on HMBC correlations of H-3 with C-2, C-4, C-10, C-1', H-5 with C-4, C-9, C-10, H-8 with C-6, C-7, C-9, C-10, and H-6' with C-2 (see FIG. 3).
After the parent compound is identified, the remaining substituents, hydroxypropyl and methoxy, can be considered as substituents on the flavone. Two methoxyhydrogens (. delta.) can be observed in the HMBC spectra of the compounds (see FIG. 3)H3.81 and 3.79) in connection with HMBC at C-6 and C-2', it can be speculated that two methoxy groups are substituted at the C-6 and C-2' positions, respectively; according to H2-1″(δH2.72) and C-6, C-7, C-8, H2-2″(δH1.89) and C-7, and H-8 (. delta.))H6.80) and C-1 "HMBC, it was confirmed that the hydroxypropyl substitution was at the C-7 position. In addition, the typical proton signal on the benzene ring [ H-5, delta ]H 7.19s；H-8,δH6.80s，H-3′δH6.93(d)7.6；H-4′，δH 7.36(t)7.6；H-5′，δH 6.88(t)7.6；H-6′，δH 7.82(d)7.6]It was also confirmed that the flavone compound of the present invention has a 6, 7-disubstituted ring B and a 2' -monosubstituted ring C. To this end, the structure of the compound was determined and the compound was named: 7- (3-hydroxypropyl) -8, 2' -dimethoxyflavone, common name is rose flavone-U.
TABLE 1 preparation of the compounds of the invention1H NMR and13C NMR data (CDCl)3)
Infrared, ultraviolet and mass spectral data of compounds: violet spectrum (methanol), lambdamax(log ε)358(3.73), 256(3.95), 210 (4.33); infrared spectroscopy (potassium bromide pellet): v ismax3428、2857、1665、1618、1552、1463、1150、1258、1150、1064cm-1；1H and13C NMR data (500 and 125MHz in CDCl as solvent)3) See Table-1; positive ion mode ESIMS M/z363[ M + Na ]]+(ii) a Positive ion mode HRESIMS M/z363.1215[ M + Na ]]+(calculated 363.1208, C20H20NaO5)。
additive preparation example 1
The additive in the embodiment is prepared from the following raw materials: 10% of rose honey, 0.25% of phenethyl alcohol, 0.15% of phenethyl propionate, 0.1% of phenethyl formate, 0.04% of vanillin, 0.12% of ethyl vanillin, 0.2% of rose flavone-U, 4% of royal jelly, 10% of propylene glycol, 1% of beeswax absolute, 0.25% of rose essential oil, 2% of phyllanthus emblica extract and 71.89% of water. The components are uniformly mixed according to the proportion and are fully dissolved to obtain a light yellow transparent solution with strong sweet fragrance, namely the additive disclosed by the invention. 1.2% of the additive of this example was added to a certain brand of cigarette paper in Yunnan. Rolling to obtain cigarette, performing sensory evaluation according to GB5606.4-2005 standard, and using cigarette without the additive as control. The evaluation results show that: the cigarette paper is added with the additive, so that the cigarette has full and fine fragrance, smoke is smoother and smoother when passing through the throat, the sweet feeling is obviously enhanced, and the smoking comfort is improved.
Additive preparation example 2
The additive in the embodiment is prepared from the following raw materials: 10% of rose honey, 0.2% of phenethyl alcohol, 0.2% of phenethyl propionate, 0.08% of phenethyl formate, 0.04% of vanillin, 0.1% of ethyl vanillin, 0.25% of rose flavone-U, 3% of royal jelly, 10% of propylene glycol, 1% of beeswax absolute, 0.3% of rose essential oil, 1.8% of phyllanthus emblica extract and 73.23% of water. The components are uniformly mixed according to the proportion and are fully dissolved to obtain a light yellow transparent solution with strong sweet fragrance, namely the additive disclosed by the invention. 1.5% of the additive of this example was added to a certain brand of cigarette paper in Yunnan. Rolling to obtain cigarette, performing sensory evaluation according to GB5606.4-2005 standard, and using cigarette without the additive as control. The evaluation results show that: the cigarette paper is added with the additive, so that the cigarette has rich aroma and very prominent sweet and sweet characteristics; the aftertaste of the oral cavity is comfortable and clean, the mouth cavity has light sweet feeling, the stimulation of the throat is reduced, the smoke is smoother and smoother, and the suction comfort is improved.
Additive preparation example 3
The additive in the embodiment is prepared from the following raw materials: 12% of rose honey, 0.2% of phenethyl alcohol, 0.2% of phenethyl propionate, 0.1% of phenethyl formate, 0.04% of vanillin, 0.12% of ethyl vanillin, 0.25% of rose flavone-U, 3% of royal jelly, 12% of propylene glycol, 1.2% of beeswax absolute, 0.3% of rose essential oil, 2% of phyllanthus emblica extract and 68.59% of water. The components are uniformly mixed according to the proportion and are fully dissolved to obtain a light yellow transparent solution with strong sweet fragrance, namely the additive disclosed by the invention. 2% of the additive of the embodiment is added into a certain brand of cigarette paper in Yunnan. Rolling to obtain cigarette, performing sensory evaluation according to GB5606.4-2005 standard, and using cigarette without the additive as control. The evaluation results show that: the cigarette paper is added with the additive, so that the cigarette smoke has rich aroma, the characteristics of dense sweetness and aroma are very obvious, the cigarette has light sweet feeling, the throat irritation is reduced, the smoke is smoother and smoother, the smoking comfort is improved, and the cigarette smoke is slightly incompatible with the original aroma of the original cigarette.
additive preparation example 4
The additive in the embodiment is prepared from the following raw materials: 12% of rose honey, 0.3% of phenethyl alcohol, 0.2% of phenethyl propionate, 0.1% of phenethyl formate, 0.06% of vanillin, 0.15% of ethyl vanillin, 0.3% of rose flavone-U, 4% of royal jelly, 12% of propylene glycol, 1.2% of beeswax absolute, 0.2% of rose essential oil, 1.8% of phyllanthus emblica extract and 67.69% of water. The components are uniformly mixed according to the proportion and are fully dissolved to obtain a light yellow transparent solution with strong sweet fragrance, namely the additive disclosed by the invention. 1.6% of the additive of this example was added to a certain brand of cigarette paper in Yunnan. Rolling to obtain cigarette, performing sensory evaluation according to GB5606.4-2005 standard, and using cigarette without the additive as control. The evaluation results show that: the cigarette paper is added with the additive, so that the comfort of the throat sucked by the cigarette is obviously improved, the smoke is smoother and smoother, the special fresh and sweet aroma of the cloud cigarette is enhanced, the aftertaste of the oral cavity is comfortable, and the sweet feeling is prominent.
Additive preparation example 5
The additive in the embodiment is prepared from the following raw materials: 9% of rose honey, 0.2% of phenethyl alcohol, 0.15% of phenethyl propionate, 0.1% of phenethyl formate, 0.04% of vanillin, 0.1% of ethyl vanillin, 0.2% of rose flavone-U, 2% of royal jelly, 9% of propylene glycol, 0.8% of beeswax absolute, 0.2% of rose essential oil, 1.5% of phyllanthus emblica extract and 76.71% of water. The components are uniformly mixed according to the proportion and are fully dissolved to obtain a light yellow transparent solution with strong sweet fragrance, namely the additive disclosed by the invention. 1.0% of the additive of the embodiment is added into a certain brand of cigarette paper in Yunnan. Rolling to obtain cigarette, performing sensory evaluation according to GB5606.4-2005 standard, and using cigarette without the additive as control. The evaluation results show that: the cigarette paper is added with the additive, so that the comfort of the throat of cigarette smoking is obviously improved, the irritation is reduced, the sweet taste of honey and the sweet taste of the oral cavity are prominent, but the fragrance amount is slightly insufficient.
additive preparation example 6
The additive in the embodiment is prepared from the following raw materials: 10% of rose honey, 0.25% of phenethyl alcohol, 0.2% of phenethyl propionate, 0.1% of phenethyl formate, 0.05% of vanillin, 0.12% of ethyl vanillin, 0.25% of rose flavone-U, 3% of royal jelly, 10% of propylene glycol, 1% of beeswax absolute, 0.25% of rose essential oil, 1.8% of phyllanthus emblica extract and 72.98% of water. The components are uniformly mixed according to the proportion and are fully dissolved to obtain a light yellow transparent solution with strong sweet fragrance, namely the additive disclosed by the invention. 1.5% of the additive of this example was added to a certain brand of cigarette paper in Yunnan. Rolling to obtain cigarette, performing sensory evaluation according to GB5606.4-2005 standard, and using cigarette without the additive as control. The evaluation results show that: the cigarette paper is added with the additive, so that the cigarette has rich fragrance, good harmony with the original fragrance of the tobacco, more exquisite and smooth smoke, obvious effect of reducing the irritation of the throat, clean aftertaste and prominent mouth rewweet.
Additive preparation example 7
The additive in the embodiment is prepared from the following raw materials: 10% of rose honey, 0.2% of phenethyl alcohol, 0.15% of phenethyl propionate, 0.09% of phenethyl formate, 0.04% of vanillin, 0.12% of ethyl vanillin, 0.3% of rose flavone-U, 4% of royal jelly, 10% of propylene glycol, 1% of beeswax absolute, 0.3% of rose essential oil, 2% of phyllanthus emblica extract and 71.8% of water. The components are uniformly mixed according to the proportion and are fully dissolved to obtain a light yellow transparent solution with strong sweet fragrance, namely the additive disclosed by the invention. 1.6% of the additive of this example was added to a certain brand of cigarette paper in Yunnan. Rolling to obtain cigarette, performing sensory evaluation according to GB5606.4-2005 standard, and using cigarette without the additive as control. The evaluation results show that: the cigarette paper is added with the additive, so that the throat dryness and prickle of cigarette smoke are obviously reduced, the smoke is more mellow and smooth through the throat, the aftertaste is comfortable and clean, the sweet feeling is prominent, and the special fresh and sweet fragrance of cloud cigarette is enhanced.
Sensory evaluation experiment:
Sensory evaluation was performed on the cigarette samples of additive preparation examples 1 to 7 according to the method of GB5606.4-2005, and the evaluation results are shown in Table-2. As can be seen from the results of the panel test in Table 2, the additive preparations 1 to 7 had a combined score of 91 or more, which was higher than that of the control sample. The cigarette paper added with the additive can improve the throat comfort of cigarette smoking, the smoke becomes smoother when passing through the throat, and the sharp sensation of the throat is reduced.
TABLE-2 additive examples 1-7 cigarette sample smoking evaluation results

Claims (5)

1. A cigarette paper additive with the effects of returning sweet and moistening throat is prepared from the following raw materials in percentage by mass: 9 to 12 percent of rose honey, 0.2 to 0.3 percent of phenethyl alcohol, 0.15 to 0.2 percent of phenethyl propionate, 0.08 to 0.1 percent of phenethyl formate, 0.04 to 0.06 percent of vanillin, 0.1 to 0.15 percent of ethyl vanillin, 0.2 to 0.3 percent of rose flavone-U, 2 to 4 percent of royal jelly, 9 to 12 percent of propylene glycol, 0.8 to 1.2 percent of beeswax absolute, 0.2 to 0.3 percent of rose essential oil, 1.5 to 2 percent of phyllanthus emblica extract and the balance of water;
Wherein the rose flavone-U is a new flavonoid compound separated from waste residue after the production of rose essential oil, and has the following structural formula:
The compound was named: 7- (3-hydroxypropyl) -6, 2' -dimethoxyflavone, English name: 7- (3-hydroxyproyl) -6, 2' -dimethoxy-flavanone;
The preparation method of the rose flavone-U comprises the following steps:
(1) Sample extraction: ultrasonically extracting waste residues after the production of the rose essential oil for 2-5 times by using a solvent, wherein the weight of the solvent used in each extraction is 2-6 times that of the waste residues, the extraction time is 30-60 minutes each time, combining the extracting solutions, filtering, concentrating the filtrate under reduced pressure until just precipitates, standing for 20-60 minutes, and filtering the precipitates to obtain a sample extracting solution;
(2) MCI decoloration: loading the sample extractive solution on MCI column, collecting eluate, and concentrating under reduced pressure to obtain extract;
(3) silica gel column chromatography: performing silica gel column chromatography on the extract, wherein the silica gel filled in the column is 160-200 meshes, and the weight of the silica gel is 6-10 times that of the extract; performing gradient elution with chloroform-acetone solution at volume ratio of 20:1,9:1,8:2,7:3,6:4 and 1:1, collecting gradient eluates of each gradient, concentrating, monitoring by TLC, and mixing the same fractions;
(4) high performance liquid chromatography separation: separating and purifying the eluent obtained by eluting chloroform-acetone with the ratio of 8:2 by adopting high performance liquid chromatography, detecting the wavelength of 358nm by using an ultraviolet detector, collecting chromatographic peaks for 30-45 min, accumulating for multiple times and evaporating to dryness to obtain the compound;
The raw materials are uniformly mixed and fully dissolved to obtain a light yellow transparent solution, namely the required cigarette paper additive.
2. The cigarette paper additive according to claim 1, characterized in that: in the step (1), the solvent is an acetone aqueous solution with the volume concentration of 70-100%, an ethanol aqueous solution with the volume concentration of 70-100% or a methanol aqueous solution with the volume concentration of 70-100%.
3. The cigarette paper additive according to claim 1, characterized in that: in the step (3), before the extract is subjected to silica gel column chromatography, acetone or methanol which is 1.5-3 times of the weight of the extract is used for dissolving the extract, then 80-100 meshes of silica gel which is 0.8-1.2 times of the weight of the extract is used for mixing the sample, and then the sample is loaded.
4. The cigarette paper additive according to claim 1, characterized in that: in the step (4), the high performance liquid chromatography separation and purification uses a methanol aqueous solution with a volume concentration of 45-65% as a mobile phase, the flow rate is 15-25 mL/min, a Zorba xPrepHT GF reversed-phase preparation column with the thickness of 21.2 x 250mm and 5 mu m as a stationary phase, the detection wavelength of an ultraviolet detector is 358nm, 0.5-1.0 mL of sample is injected each time, chromatographic peaks of 38.6min are collected, and the chromatographic peaks are evaporated to dryness after multiple accumulation.
5. The use of the cigarette paper additive of claim 1 in cigarette production, specifically: in the cigarette paper preparation process, the additive is coated according to 1-2% of the weight of the cigarette paper.
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