CN114213317A - Organic acid arecoline and preparation method thereof - Google Patents
Organic acid arecoline and preparation method thereof Download PDFInfo
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- CN114213317A CN114213317A CN202111583680.0A CN202111583680A CN114213317A CN 114213317 A CN114213317 A CN 114213317A CN 202111583680 A CN202111583680 A CN 202111583680A CN 114213317 A CN114213317 A CN 114213317A
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- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
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Abstract
The invention relates to an organic acid arecoline and a preparation method thereof, wherein the molecular formula of the organic acid arecoline is C8H13NO2R, R is selected from C3H5O3、C7H5O2、C5H7O3、C4H5O5、C6H7O7、C4H5O6、C7H5O4And C4H5O4One kind of (1). The organic acid arecoline is a new kind of arecoline salt, and other organic acid arecoline salts are prepared by using hydrobromic acid as a raw material.
Description
Technical Field
The invention relates to the technical field of organic compounds, in particular to organic acid arecoline and a preparation method thereof.
Background
Arecoline (Arecoline) has chemical name of N-methyl-1, 2, 5, 6-tetrahydronicotinic acid methyl ester and molecular formula of C8H13NO2It is an M, N receptor agonist, has anticholinergic effect on central nervous system, and can be used asSynthesis of other M receptor agonists.
Compared with free arecoline, the arecoline salt has the characteristics of higher stability, better water solubility and the like. Arecoline is an alkaloid similar to nicotine, can bring physiological effects similar to nicotine while being sucked, and has similar properties. However, the existing betel nut alkali salts are few in variety, and some of the existing betel nut alkali salts are poor in taste or physiological effect, so that new betel nut alkali salts need to be developed.
Disclosure of Invention
Based on the above, the invention provides the organic acid arecoline which is a novel arecoline salt and has good taste and strong physiological effect.
An organic acid arecoline with molecular formula of C8H13NO2R and R are selected from C3H5O3、C7H5O2、C5H7O3、C4H5O5、C6H7O7、C4H5O6、C7H5O4And C4H5O4One kind of (1).
The invention also provides a preparation method of the organic acid arecoline, which comprises the following steps:
providing an areca-nut hydrobromate solution and an inorganic alkali solution, adding the inorganic alkali solution into the areca-nut hydrobromate solution, stirring, and uniformly mixing to obtain a solution A;
adding organic acid into the solution A, and stirring to obtain a solution B;
carrying out reduced pressure distillation on the solution B, and evaporating the solvent in the solution B to obtain a solid C;
dissolving the solid C in an organic solvent, and filtering to obtain a solution D;
and drying the solution D, and separating out crystals to obtain the organic acid arecoline.
In one embodiment, in the arecoline hydrobromide solution and the inorganic alkali solution, the molar ratio of the arecoline hydrobromide to the inorganic alkali is (1-2): (1-3).
In one embodiment, the molar ratio of the arecoline hydrobromide to the organic acid in the arecoline hydrobromide solution and the organic acid is 1: (1-3).
In one embodiment, the inorganic base solution is selected from one or a combination of at least two of sodium carbonate, sodium bicarbonate, sodium hydroxide, potassium carbonate, potassium bicarbonate, and potassium hydroxide.
In one embodiment, the solvent of the areca hydrobromate solution is water or small molecular alcohols.
In one embodiment, the organic acid is selected from one or more of lactic acid, benzoic acid, levulinic acid, malic acid, citric acid, tartaric acid, gentisic acid and succinic acid.
In one embodiment, the temperature of the reduced pressure distillation is 50-60 ℃, and the vacuum degree is 0.1-0.2 MPa.
In one embodiment, the organic solvent is absolute ethanol.
In one embodiment, the solution D is dried to precipitate crystals, and the preparation method comprises: and transferring the solution D to a crystallizing dish, placing the crystallizing dish in a fume hood at normal temperature in an open manner, separating out crystals, filtering, taking filter residues, washing the filter residues, and drying the filter residues at low temperature to obtain the organic acid arecoline.
1. The organic acid arecoline is a new kind of arecoline alkali salt, is prepared by adopting the corresponding organic acid as a raw material, generates the corresponding organic acid arecoline alkali salt, can obtain the same physiological effect of chewing areca when being used as an aerosol generating substrate of an aerosol generating device, has good taste and strong physiological effect, and the higher the content is, the stronger the physiological effect is;
2. the preparation method of the organic acid arecoline adopts the hydrobromic acid arecoline as a raw material, firstly uses inorganic base to neutralize the hydrobromic acid to obtain an alkaline intermediate product solution A, then adds organic acid to perform a neutralization reaction with the solution A to generate a crude product solution B of the arecoline salt corresponding to the organic acid, and the solution B is optimized to obtain the organic acid arecoline corresponding to the organic acid.
Drawings
FIG. 1 is a hydrogen spectrum of arecoline lactate according to example 1 of the present invention;
FIG. 2 is a carbon spectrum of arecoline lactate according to example 1 of the present invention.
Detailed Description
In order that the invention may be more fully understood, reference will now be made to the following description. This invention may, however, be embodied in many different forms and should not be construed as limited to the embodiments set forth herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete.
Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. The terminology used in the description of the invention herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention.
The invention provides an organic acid arecoline, the molecular formula of which is C8H13NO2R and R are selected from C3H5O3(lactic acid) C7H5O2(benzoic acid), C5H7O3(levulinic acid), C4H5O5(malic acid), C6H7O7(citric acid), C4H5O6(tartaric acid), C7H5O4(gentisic acid) and C4H5O4(succinic acid).
The organic acid arecoline is a new kind of arecoline base salt, is prepared by adopting the corresponding organic acid as a raw material, generates the corresponding organic acid arecoline base salt, can obtain the same physiological effect of chewing areca when being used as an aerosol generating substrate of an aerosol generating device, and has good taste, strong physiological effect, higher content and stronger physiological effect.
The invention also provides a preparation method of the organic acid arecoline, which comprises the following steps:
s100: providing an areca-nut hydrobromate solution and an inorganic alkali solution, adding the inorganic alkali solution into the areca-nut hydrobromate solution, stirring, and uniformly mixing to obtain a solution A.
Optionally, the solvent of the arecoline hydrobromide solution is water or small molecular alcohol such as methanol, ethanol, propanol, etc., wherein the ethanol can be 95% (volume ratio) ethanol, and the arecoline hydrobromide solution is dissolved in the solvent.
Optionally, the mass content of arecoline hydrobromide in the arecoline hydrobromide solution is 10% to 50%, it can be understood that any concentration of the arecoline hydrobromide solution can react with the inorganic alkali solution to generate solution a, and further react with the subsequent organic acid, but if the mass content of arecoline hydrobromide is too small, for example, less than 10%, the reaction rate is slow, or the yield is low, and the economic benefit is low; if the arecoline bromate content is too large, for example, greater than 50%, the crystallization effect may be affected by adding other raw materials at a time in a large amount.
Optionally, in the arecoline hydrobromide solution and the inorganic alkali solution, the molar ratio of the arecoline hydrobromide to the inorganic alkali is (1-2): (1-3), the molar amount of the inorganic base is equal to or slightly larger than that of the arecoline hydrobromide, and the hydrobromic acid is completely neutralized.
Optionally, the inorganic alkali solution is one or a combination of at least two of sodium carbonate, sodium bicarbonate, sodium hydroxide, potassium carbonate, potassium bicarbonate and potassium hydroxide, and the inorganic alkali solution has strong alkalinity and good solubility and can well neutralize hydrobromic acid.
S200: adding organic acid into the solution A, and stirring to obtain a solution B.
Optionally, in the arecoline hydrobromide solution and the organic acid, the molar ratio of the arecoline hydrobromide to the organic acid is 1: (1-3), the molar quantity of the organic acid is more than or equal to that of the arecoline hydrobromide, so that the reaction of the arecoline hydrobromide and the organic acid can be promoted to be carried out in the forward reaction direction.
Optionally, the organic acid is selected from one or more of lactic acid, benzoic acid, levulinic acid, malic acid, citric acid, tartaric acid, gentisic acid and succinic acid, and the betel nut alkali salt corresponding to the organic acid has good performance, is suitable for suction of the aerosol generating device, and has good experience.
S300: and distilling the solution B under reduced pressure, and evaporating the solvent in the solution B to obtain a solid C.
Optionally, the temperature of the reduced pressure distillation is 50-60 ℃, and the vacuum degree is 0.1-0.2 MPa.
S400: the solid C was dissolved in an organic solvent and filtered to obtain a solution D.
Alternatively, the organic solvent is absolute ethanol, can dissolve the solid C, provides a good environment for crystal formation, and is easily evaporated in a subsequent drying step.
S500: and drying the solution D, and separating out crystals to obtain the organic acid arecoline.
Optionally, the preparation method of the precipitated crystal by drying the solution D comprises the following steps: and transferring the solution D to a crystallizing dish, placing the crystallizing dish in a fume hood at normal temperature in an open manner, separating out crystals, filtering, taking filter residues, washing the filter residues, and drying the filter residues at low temperature to obtain the organic acid arecoline. Generally, the solution D is transferred to a crystallization dish and placed in a fume hood open to allow crystals to precipitate in about 48 hours, and optionally for at least 48 hours in practice.
The preparation method of the organic acid arecoline adopts the hydrobromic acid arecoline as a raw material, firstly uses inorganic base to neutralize the hydrobromic acid to obtain an alkaline intermediate product solution A, then adds organic acid to perform a neutralization reaction with the solution A to generate a crude product solution B of the arecoline salt corresponding to the organic acid, and the solution B is optimized to obtain the organic acid arecoline corresponding to the organic acid.
The following is an example description.
Example 1
The arecoline is lactic acid arecoline with molecular formula C11H18NO5。
The preparation method of the organic acid arecoline comprises the following steps:
s10: 5g of arecoline hydrobromide is dissolved in 20g of water to obtain the arecoline hydrobromide solution.
S20: 1.35g of sodium carbonate was dissolved in 12.15g of ultrapure water to obtain a sodium carbonate solution.
S100: adding sodium carbonate solution into areca-nut hydrobromate solution, stirring, and uniformly mixing to obtain solution A.
S200: to the solution A, 6.18g of lactic acid having a concentration of 80 wt% was slowly added, followed by stirring to obtain a solution B.
S300: and (3) carrying out reduced pressure distillation on the solution B, wherein the temperature of the reduced pressure distillation is (52 +/-2) DEG C, the vacuum degree is 0.1MPa, and evaporating the solvent in the solution B to obtain a solid C.
S400: the solid C was dissolved in absolute ethanol and filtered to obtain a solution D.
S500: and transferring the solution D to a crystallizing dish, placing the crystallizing dish in a fume hood in an open manner at normal temperature, separating out crystals after 48 hours, filtering, taking filter residues, washing the filter residues, and drying the filter residues at low temperature to obtain the arecoline lactate.
Example 2
The arecoline is lactic acid arecoline with molecular formula C11H18NO5。
The preparation method of the organic acid arecoline comprises the following steps:
s10: 9g of arecoline hydrobromide is dissolved in 15g of 95 percent ethanol to obtain the arecoline hydrobromide solution.
S20: sodium bicarbonate solution was obtained by dissolving 4.5g of sodium bicarbonate in 22g of ultrapure water.
S100: adding the sodium bicarbonate solution into the areca-nut hydrobromate solution, stirring, and uniformly mixing to obtain a solution A.
S200: 4.5g of lactic acid having a concentration of 80 wt% was slowly added to the solution A, followed by stirring to obtain a solution B.
S300: and (3) carrying out reduced pressure distillation on the solution B, wherein the temperature of the reduced pressure distillation is (53 +/-2) DEG C, the vacuum degree is 0.15MPa, and evaporating the solvent in the solution B to obtain a solid C.
S400: the solid C was dissolved in absolute ethanol and filtered to obtain a solution D.
S500: and transferring the solution D to a crystallizing dish, placing the crystallizing dish in a fume hood at normal temperature in an open manner, precipitating crystals after 48 hours, filtering, washing and drying at low temperature to obtain the arecoline lactate.
Example 3
The arecoline is lactic acid arecoline with molecular formula C11H18NO5。
The preparation method of the organic acid arecoline comprises the following steps:
s10: dissolving arecoline hydrobromide 8g in water 20g to obtain arecoline hydrobromide solution.
S20: 1.5g of sodium hydroxide was dissolved in 15g of ultrapure water to obtain a sodium hydroxide solution.
S100: adding the sodium hydroxide solution into the areca-nut hydrobromate solution, stirring and uniformly mixing to obtain a solution A.
S200: 6.8g of lactic acid having a concentration of 80 wt% was slowly added to the solution A, followed by stirring to obtain a solution B.
S300: and (3) carrying out reduced pressure distillation on the solution B, wherein the temperature of the reduced pressure distillation is (55 +/-3) DEG C, the vacuum degree is 0.12MPa, and evaporating the solvent in the solution B to obtain a solid C.
S400: the solid C was dissolved in absolute ethanol and filtered to obtain a solution D.
S500: and transferring the solution D to a crystallizing dish, placing the crystallizing dish in a fume hood in an open manner at normal temperature, separating out crystals after 48 hours, filtering, taking filter residues, washing the filter residues, and drying the filter residues at low temperature to obtain the arecoline lactate.
Example 4
The arecoline is a benzoic acid arecoline with a molecular formula of C15H18NO4。
The preparation method of the organic acid arecoline comprises the following steps:
s10: 10g of arecoline hydrobromide is dissolved in 32g of 95% ethanol to obtain the arecoline hydrobromide solution.
S20: 3.2g of potassium carbonate was dissolved in 20g of ultrapure water to obtain a potassium carbonate solution.
S100: adding the potassium carbonate solution into the areca-nut hydrobromate solution, stirring, and uniformly mixing to obtain a solution A.
S200: 6.3g of benzoic acid having a concentration of 85% by weight was slowly added to the solution A, followed by stirring to obtain a solution B.
S300: and (3) carrying out reduced pressure distillation on the solution B, wherein the temperature of the reduced pressure distillation is (55 +/-2) DEG C, the vacuum degree is 0.2MPa, and evaporating the solvent in the solution B to obtain a solid C.
S400: the solid C was dissolved in absolute ethanol and filtered to obtain a solution D.
S500: and transferring the solution D to a crystallizing dish, placing the crystallizing dish in a fume hood in an open manner at normal temperature, separating out crystals after 48 hours, filtering, taking filter residues, washing the filter residues, and drying the filter residues at low temperature to obtain the betelnut benzoate.
Example 5
The organic acid arecoline in this embodiment is arecoline malate, and the molecular formula of the organic acid arecoline is C12H18NO7。
The preparation method of the organic acid arecoline comprises the following steps:
s10: dissolving arecoline hydrobromide 12g in water 30g to obtain arecoline hydrobromide solution.
S20: 2.8g of sodium carbonate was dissolved in 18g of ultrapure water to obtain a sodium carbonate solution.
S100: adding sodium carbonate solution into areca-nut hydrobromate solution, stirring, and uniformly mixing to obtain solution A.
S200: 9.1g of malic acid having a concentration of 82 wt% was slowly added to the solution A, followed by stirring to obtain a solution B.
S300: and (3) carrying out reduced pressure distillation on the solution B, wherein the temperature of the reduced pressure distillation is (58 +/-2) DEG C, the vacuum degree is 0.15MPa, and evaporating the solvent in the solution B to obtain a solid C.
S400: the solid C was dissolved in absolute ethanol and filtered to obtain a solution D.
S500: and transferring the solution D to a crystallizing dish, placing the crystallizing dish in a fume hood in an open manner at normal temperature, separating out crystals after 48 hours, filtering, washing filter residues, and drying the filter residues at low temperature to obtain the arecoline malate.
The hydrogen spectrum and the carbon spectrum of arecoline lactate of example 1 were tested, and the test results are shown in fig. 1 and 2.
The arecoline lactate according to example 1, the arecoline benzoate according to example 4, and the arecoline malate according to example 5 were formulated as an aerosol-generating substrate according to table 1.
TABLE 1
The same batch of atomizers without aerosol generating substrates are respectively injected with No. 1-19 aerosol generating substrates, No. 1 is a comparative example, and the mixture is kept stand for 30 minutes. 90 test users were provided with 1-19 randomly numbered aerosol generating devices and during the test the users took a sample of the aerosol generating substrate according to the usual habit of aspirating the aerosol generating substrate, took a sufficient amount of breath, and then returned to the pharynx in a gentle manner to exhale the inhaled aerosol vapor slowly from the nasal cavity. Each flavor was pumped for 3 minutes each time.
TABLE 2
From the evaluation results, the aerosol generating substrate containing arecoline lactate, arecoline benzoate and arecoline malate can be sucked to obtain the same physiological effect of chewing areca, and the higher the content is, the stronger the physiological effect is.
The technical features of the embodiments described above may be arbitrarily combined, and for the sake of brevity, all possible combinations of the technical features in the embodiments described above are not described, but should be considered as being within the scope of the present specification as long as there is no contradiction between the combinations of the technical features.
The above-mentioned embodiments only express one embodiment of the present invention, and the description thereof is more specific and detailed, but not construed as limiting the scope of the invention. It should be noted that, for a person skilled in the art, several variations and modifications can be made without departing from the inventive concept, which falls within the scope of the present invention. Therefore, the protection scope of the present patent shall be subject to the appended claims.
Claims (10)
1. An organic acid arecoline, which is characterized in that the molecular formula of the organic acid arecoline is C8H13NO2R, R is selected from C3H5O3、C7H5O2、C5H7O3、C4H5O5、C6H7O7、C4H5O6、C7H5O4And C4H5O4One kind of (1).
2. The method for preparing arecoline as an organic acid according to claim 1, comprising the steps of:
providing an areca-nut hydrobromate solution and an inorganic alkali solution, adding the inorganic alkali solution into the areca-nut hydrobromate solution, stirring, and uniformly mixing to obtain a solution A;
adding organic acid into the solution A, and stirring to obtain a solution B;
carrying out reduced pressure distillation on the solution B, and evaporating the solvent in the solution B to obtain a solid C;
dissolving the solid C in an organic solvent, and filtering to obtain a solution D;
and drying the solution D, and separating out crystals to obtain the organic acid arecoline.
3. The method for preparing arecoline as an organic acid according to claim 2, wherein the molar ratio of arecoline hydrobromide to inorganic base in the arecoline hydrobromide and inorganic base solutions is (1-2): (1-3).
4. The method of claim 2, wherein the molar ratio of the arecoline hydrobromide to the organic acid in the arecoline hydrobromide solution and the organic acid is 1: (1-3).
5. The method for preparing arecoline as an organic acid in claim 2, wherein said inorganic alkali solution is one or a combination of at least two of sodium carbonate, sodium bicarbonate, sodium hydroxide, potassium carbonate, potassium bicarbonate and potassium hydroxide.
6. The method for preparing arecoline as an organic acid in claim 2, wherein the solvent of the arecoline hydrobromide solution is water or a small alcohol.
7. The method for preparing arecoline as an organic acid in claim 2, wherein said organic acid is selected from one or more of lactic acid, benzoic acid, levulinic acid, malic acid, citric acid, tartaric acid, gentisic acid and succinic acid.
8. The method for preparing arecoline as an organic acid in claim 2, wherein the temperature of the reduced pressure distillation is 50-60 ℃ and the vacuum degree is 0.1-0.2 MPa.
9. The method for preparing arecoline as claimed in claim 2, wherein said organic solvent is absolute ethanol.
10. The method for preparing arecoline as an organic acid in claim 2, wherein said drying said solution D to precipitate crystals is performed by: and transferring the solution D to a crystallizing dish, placing the crystallizing dish in a fume hood in an open manner at normal temperature, separating out crystals, filtering, taking filter residues, washing the filter residues, and drying the filter residues at low temperature to obtain the organic acid arecoline.
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| CN112574099A (en) * | 2020-10-26 | 2021-03-30 | 海南浦金科技有限责任公司 | Method for extracting natural arecoline |
| WO2021190645A1 (en) * | 2020-03-27 | 2021-09-30 | 深圳市水槟榔生物科技有限公司 | Arecoline salt, preparation method therefor and product thereof |
| CN113620865A (en) * | 2021-09-06 | 2021-11-09 | 云南巴菰生物科技股份有限公司 | Betel nut alkali salt and preparation method thereof |
| CN113812665A (en) * | 2021-10-08 | 2021-12-21 | 云南巴菰生物科技股份有限公司 | Electronic cigarette atomized liquid containing betelnut citrate salt and preparation method thereof |
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| WO2021190645A1 (en) * | 2020-03-27 | 2021-09-30 | 深圳市水槟榔生物科技有限公司 | Arecoline salt, preparation method therefor and product thereof |
| CN112574099A (en) * | 2020-10-26 | 2021-03-30 | 海南浦金科技有限责任公司 | Method for extracting natural arecoline |
| CN113620865A (en) * | 2021-09-06 | 2021-11-09 | 云南巴菰生物科技股份有限公司 | Betel nut alkali salt and preparation method thereof |
| CN113812665A (en) * | 2021-10-08 | 2021-12-21 | 云南巴菰生物科技股份有限公司 | Electronic cigarette atomized liquid containing betelnut citrate salt and preparation method thereof |
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