A nut aroma compound and preparation method thereof and nut aroma coffee aroma base

Abstract

The present invention relates to the technical field of spices, and in particular to a nut aroma compound and a preparation method thereof and a nut aroma coffee aroma base, having the following structural formula: chemical name is o-chlorobenzoic acid 4-methylcoumarin-7-mercapto ester. The compound of the present invention has a strong coffee aroma, and its aroma is obvious, and the aroma retention time is long, and it has potential application value in daily chemicals such as aromatherapy; the method for preparing the mixture is simple and efficient, and the operation and control are convenient, the product quality produced is high, the cost is low, and it is conducive to industrial production, and the nut aroma compound obtained at the same time has an aroma similar to that of nut aroma, which can effectively overcome the disadvantages of conventional flavors as flavor additives in the past, and can make the aroma base added with nut aroma compounds have an aroma similar to that of nut aroma.

Description

Technical Field

[0001] The invention relates to the technical field of spices, and in particular to a nut aroma compound and a preparation method thereof and a nut aroma coffee aroma base. Background Art

[0002] Sensory omics is the latest development in the field of aromatherapy and other daily chemicals. It explains the essence of the fragrance of aromatherapy and other daily chemicals at the molecular level. The results of sensory omics research show that there are only about 230 volatile components that significantly contribute to the aroma of aromatherapy and other daily chemicals. For a certain food, the real aroma components are only more than 30. This provides analysts and perfumers with the possibility to reproduce the flavor of aromatherapy and other daily chemicals through constructive cooperation.

[0003] There are thousands of coffee flavors, among which nutty aroma is an important part of the characteristic flavor of coffee. The diversity of nutty aroma also makes coffee present a variety of flavor experiences. However, the aroma raw materials used to reflect its characteristic aroma are relatively limited. Therefore, the development of compounds with cucumber characteristic aroma is conducive to enriching the scope of use of aroma raw materials. In addition, the development of compounds with nutty aroma can enrich the flavor categories of coffee, especially in daily chemicals such as aromatherapy. It has potential application value. Summary of the invention

[0004] In order to overcome the shortcomings and deficiencies in the prior art, the purpose of the present invention is to provide a nut aroma compound, which has a strong coffee aroma, a distinct aroma, a long lasting aroma, and has potential application value in daily chemicals such as aromatherapy.

[0005] Another object of the present invention is to provide a method for preparing nut aroma compounds, which is simple and efficient, easy to operate and control, has high product quality and low cost, is conducive to industrial production, and at the same time, the prepared nut aroma compounds have an aroma similar to that of nuts, which can effectively overcome the disadvantages of conventional flavors as flavor additives.

[0006] Another object of the present invention is to provide a nutty coffee aroma base, which is added with nutty aroma compounds so that the final aroma base has an aroma similar to that of nuts and has good practicality.

[0007] The object of the present invention is achieved by the following technical solution: A nut aroma compound has the following structural formula: , chemical name is 4-methylcoumarin-7-mercapto-2-chlorobenzoate.

[0008] The compound of the invention has a strong coffee aroma, which is obvious and lasts for a long time, and has potential application value in daily chemicals such as aromatherapy.

[0009] The present invention also provides a method for preparing a nut aroma compound, comprising the following steps:

[0010]

[0011] S1. Take salicylic acid, chloroform and thionyl chloride, add salicylic acid and chloroform into a reaction kettle and mix them evenly, place in an ice water bath, then add thionyl chloride into the reaction kettle and heat to 50° C. to react for 5 hours, return to room temperature to obtain a chloroform solution of o-chlorobenzoyl chloride, and set aside;

[0012]

[0013] S2, take 7-mercapto-4-methylcoumarin and anhydrous magnesium sulfate, add the chloroform solution of o-chlorobenzoyl chloride obtained in step S1 into a reactor and place it in an ice-water bath, slowly add 7-mercapto-4-methylcoumarin dropwise into the reactor, pass the generated tail gas into an aqueous sodium hydroxide solution with a mass concentration of 8-12% for absorption, react at room temperature for 3-8 hours, add a certain amount of an aqueous sodium carbonate solution with a mass concentration of 8-12% into the reactor in an ice-water bath, stir until the solution no longer bubbles, transfer the liquid into a separatory funnel, discard the aqueous phase, add an appropriate amount of anhydrous magnesium sulfate to the organic phase, stir and mix, let stand for 20-28 hours, use a rotary evaporator, at 25-35°C and a pressure of 450-550Pa, recover the dichloromethane in the organic phase, and then collect the fraction with a liquid temperature of 138-143°C at a pressure of 350Pa to obtain a light yellow liquid, which is a nut aroma compound.

[0014] The nut aroma compound of the present invention is prepared by adopting the above method, and the nut aroma compound prepared by the above method has a strong coffee aroma, and its aroma is obvious and lasts for a long time, and has potential application value in daily chemical products such as aromatherapy; the preparation method is simple and efficient, and the operation and control are convenient, the product quality is high, the cost is low, and it is conducive to industrial production. At the same time, the prepared nut aroma compound has an aroma similar to the aroma of nuts, which can effectively overcome the disadvantages of conventional flavors as flavor additives.

[0015] Preferably, in step S1, the weight ratio of salicylic acid, chloroform and thionyl chloride is 1.36-1.46:2.6-3.6:2.0-3.0.

[0016] Preferably, in step S2, the volume ratio of the chloroform solution of 7-mercapto-4-methylcoumarin and o-chlorobenzoyl chloride is 0.4-0.8:1.5-2.5.

[0017] Preferably, in step S2, the volume ratio of the 7-mercapto-4-methylcoumarin to the sodium carbonate aqueous solution is 0.4-0.8:0.8-1.2.

[0018] The present invention also provides a nutty coffee aroma base, which comprises the following raw materials in parts by weight: 4-7 parts of 4-methylcoumarin-7-mercaptolate o-chlorobenzoate, 1-4 parts of furfuryl mercaptan, 1-3 parts of acetyl pyrazine, 0.1-0.5 parts of 2,5-dimethyl pyrazine, 0.3-0.8 parts of 2,6-dimethyl pyrazine, 0.1-0.5 parts of 2,3,5-trimethyl pyrazine, 0.05-0.15 parts of tetramethyl pyrazine, 7-11 parts of isoeugenol, 3-6 parts of ethyl crotonate, 10-14 parts of furfuryl alcohol, 1.4-2.2 parts of 2-acetyl furan, 3.0-4.0 parts of furfural and 55-65 parts of anhydrous ethanol.

[0019] Preferably, the nutty coffee aroma base is prepared by the following steps:

[0020] 1) Weigh the raw materials according to weight and set aside;

[0021] 2) Add the above raw materials into a reaction device, mix, and shake repeatedly to obtain a nutty coffee aroma base.

[0022] The nutty coffee aroma base of the present invention is prepared by the above raw materials and preparation method, and the aroma base prepared by the above raw materials and preparation method is added with nut aroma compounds so that the finally prepared aroma base has an aroma similar to that of nuts, and has good practicality.

[0023] The beneficial effects of the present invention are as follows: the nut aroma compound of the present invention has a strong coffee aroma, the aroma is obvious, the aroma lasts for a long time, and has potential application value in daily chemicals such as aromatherapy.

[0024] The preparation method of the nut aroma compound of the present invention is simple and efficient, the operation and control are convenient, the product quality is high, the cost is low, and it is conducive to industrial production. At the same time, the prepared nut aroma compound has an aroma similar to that of nuts, which can effectively overcome the disadvantages of conventional flavors as flavor additives in the past; and the nut aroma coffee flavor base prepared by using the nut aroma compound has an aroma similar to that of nuts, and has good practicality. BRIEF DESCRIPTION OF THE DRAWINGS

[0025] Figure 1 It is a gas chromatogram of 4-methylcoumarin-7-mercapto-1-chlorobenzoate obtained in Example 4 of the present invention. DETAILED DESCRIPTION

[0026] In order to facilitate the understanding of those skilled in the art, the following embodiments and attached Figure 1 The present invention is further described, and the contents mentioned in the implementation modes are not intended to limit the present invention.

[0027] Example 1

[0028] A nutty aroma compound having the following structural formula:

[0029] , chemical name is 4-methylcoumarin-7-mercapto-2-chlorobenzoate.

[0030] The nut aroma compound is prepared by the following steps:

[0031] S1. Take salicylic acid, chloroform and thionyl chloride, add salicylic acid and chloroform into a reaction kettle and mix them evenly, place in an ice water bath, then add thionyl chloride into the reaction kettle and heat to 50° C. to react for 5 hours, return to room temperature to obtain a chloroform solution of o-chlorobenzoyl chloride, and set aside;

[0032] S2. Take 7-mercapto-4-methylcoumarin and anhydrous magnesium sulfate, add the chloroform solution of o-chlorobenzoyl chloride obtained in step S1 into a reactor and place it in an ice-water bath, slowly add 7-mercapto-4-methylcoumarin dropwise into the reactor, pass the generated tail gas into an 8% sodium hydroxide aqueous solution for absorption, react at room temperature for 3 hours, add a certain amount of 8% sodium carbonate aqueous solution into the reactor in an ice-water bath, stir until the solution no longer bubbles, transfer the liquid into a separatory funnel, discard the aqueous phase, add an appropriate amount of anhydrous magnesium sulfate to the organic phase, stir and mix, let stand for 20 hours, use a rotary evaporator, at 25°C and 450Pa pressure, recover the dichloromethane in the organic phase, and then collect the fraction with a liquid temperature of 138-143°C at 350Pa pressure to obtain a light yellow liquid, which is a nut aroma compound.

[0033] In step S1, the weight ratio of salicylic acid, chloroform and thionyl chloride is 1.36:2.6:2.0.

[0034] In step S2, the volume ratio of the chloroform solution of 7-mercapto-4-methylcoumarin and o-chlorobenzoyl chloride is 0.4:1.5.

[0035] In step S2, the volume ratio of the 7-mercapto-4-methylcoumarin to the sodium carbonate aqueous solution is 0.4:0.8.

[0036] A nutty coffee aroma base comprises the following raw materials in parts by weight: 4 parts of 4-methylcoumarin-7-mercaptolate o-chlorobenzoate, 1 part of furfuryl mercaptan, 1 part of acetyl pyrazine, 0.1 part of 2,5-dimethylpyrazine, 0.3 part of 2,6-dimethylpyrazine, 0.1 part of 2,3,5-trimethylpyrazine, 0.05 part of tetramethylpyrazine, 7 parts of isoeugenol, 3 parts of ethyl crotonate, 10 parts of furfuryl alcohol, 1.4 parts of 2-acetylfuran, 3.0 parts of furfural and 55 parts of anhydrous ethanol.

[0037] The nutty coffee aroma base is prepared by the following steps:

[0038] 1) Weigh the raw materials according to weight and set aside;

[0039] 2) Add the above raw materials into a reaction device, mix, and shake repeatedly to obtain a nutty coffee aroma base.

[0040] Example 2

[0041] A nutty aroma compound having the following structural formula:

[0042] , chemical name is 4-methylcoumarin-7-mercapto-2-chlorobenzoate.

[0043] The nut aroma compound is prepared by the following steps:

[0044] S1. Take salicylic acid, chloroform and thionyl chloride, add salicylic acid and chloroform into a reaction kettle and mix them evenly, place in an ice water bath, then add thionyl chloride into the reaction kettle and heat to 50° C. to react for 5 hours, return to room temperature to obtain a chloroform solution of o-chlorobenzoyl chloride, and set aside;

[0045] S2, take 7-mercapto-4-methylcoumarin and anhydrous magnesium sulfate, add the chloroform solution of o-chlorobenzoyl chloride obtained in step S1 into a reactor and place it in an ice-water bath, slowly add 7-mercapto-4-methylcoumarin dropwise into the reactor, pass the generated tail gas into a 10% sodium hydroxide aqueous solution for absorption, react at room temperature for 5 hours, add a certain amount of 10% sodium carbonate aqueous solution into the reactor in an ice-water bath, stir until the solution no longer bubbles, transfer the liquid into a separatory funnel, discard the aqueous phase, add an appropriate amount of anhydrous magnesium sulfate to the organic phase, stir and mix, let stand for 24 hours, use a rotary evaporator, at 30°C and 500Pa pressure, recover the dichloromethane in the organic phase, and then collect the fraction with a liquid temperature of 138-143°C at a pressure of 350Pa to obtain a light yellow liquid, which is a nut aroma compound.

[0046] In step S1, the weight ratio of salicylic acid, chloroform and thionyl chloride is 1.4:3.0:2.5.

[0047] In step S2, the volume ratio of the chloroform solution of 7-mercapto-4-methylcoumarin and o-chlorobenzoyl chloride is 0.6:2.0.

[0048] In step S2, the volume ratio of the 7-mercapto-4-methylcoumarin to the sodium carbonate aqueous solution is 0.6:1.0.

[0049] A nutty coffee aroma base comprises the following raw materials in parts by weight: 6 parts of 4-methylcoumarin-7-mercaptolate o-chlorobenzoate, 3 parts of furfuryl mercaptan, 2 parts of acetyl pyrazine, 0.3 parts of 2,5-dimethyl pyrazine, 0.5 parts of 2,6-dimethyl pyrazine, 0.3 parts of 2,3,5-trimethyl pyrazine, 0.10 parts of tetramethyl pyrazine, 9 parts of isoeugenol, 5 parts of ethyl crotonate, 12 parts of furfuryl alcohol, 1.8 parts of 2-acetyl furan, 3.5 parts of furfural and 60 parts of anhydrous ethanol.

[0050] The nutty coffee aroma base is prepared by the following steps:

[0051] 1) Weigh the raw materials according to weight and set aside;

[0052] 2) Add the above raw materials into a reaction device, mix, and shake repeatedly to obtain a nutty coffee aroma base.

[0053] Example 3

[0054] A nutty aroma compound having the following structural formula:

[0055] , chemical name is 4-methylcoumarin-7-mercapto-2-chlorobenzoate.

[0056] The nut aroma compound is prepared by the following steps:

[0057] S1. Take salicylic acid, chloroform and thionyl chloride, add salicylic acid and chloroform into a reaction kettle and mix them evenly, place in an ice water bath, then add thionyl chloride into the reaction kettle and heat to 50° C. to react for 5 hours, return to room temperature to obtain a chloroform solution of o-chlorobenzoyl chloride, and set aside;

[0058] S2, take 7-mercapto-4-methylcoumarin and anhydrous magnesium sulfate, add the chloroform solution of o-chlorobenzoyl chloride obtained in step S1 into a reactor and place it in an ice-water bath, slowly add 7-mercapto-4-methylcoumarin dropwise into the reactor, pass the generated tail gas into a 12% sodium hydroxide aqueous solution for absorption, react at room temperature for 8 hours, add a certain amount of 12% sodium carbonate aqueous solution into the reactor in an ice-water bath, stir until the solution no longer bubbles, transfer the liquid into a separatory funnel, discard the aqueous phase, add an appropriate amount of anhydrous magnesium sulfate to the organic phase, stir and mix, let stand for 28 hours, use a rotary evaporator, at 35°C and 550Pa pressure, recover the dichloromethane in the organic phase, and then collect the fraction with a liquid temperature of 138-143°C at 350Pa pressure to obtain a light yellow liquid, which is a nut aroma compound.

[0059] In step S1, the weight ratio of salicylic acid, chloroform and thionyl chloride is 1.46:3.6:3.0.

[0060] In step S2, the volume ratio of the chloroform solution of 7-mercapto-4-methylcoumarin and o-chlorobenzoyl chloride is 0.8:2.5.

[0061] In step S2, the volume ratio of the 7-mercapto-4-methylcoumarin to the sodium carbonate aqueous solution is 0.8:1.2.

[0062] A nutty coffee aroma base comprises the following raw materials in parts by weight: 7 parts of 4-methylcoumarin-7-mercaptolate o-chlorobenzoate, 4 parts of furfuryl mercaptan, 3 parts of acetyl pyrazine, 0.5 parts of 2,5-dimethylpyrazine, 0.8 parts of 2,6-dimethylpyrazine, 0.5 parts of 2,3,5-trimethylpyrazine, 0.15 parts of tetramethylpyrazine, 11 parts of isoeugenol, 6 parts of ethyl crotonate, 14 parts of furfuryl alcohol, 2.2 parts of 2-acetylfuran, 4.0 parts of furfural and 65 parts of anhydrous ethanol.

[0063] The nutty coffee aroma base is prepared by the following steps:

[0064] 1) Weigh the raw materials according to weight and set aside;

[0065] 2) Add the above raw materials into a reaction device, mix, and shake repeatedly to obtain a nutty coffee aroma base.

[0066] Example 4

[0067] A nutty aroma compound having the following structural formula:

[0068] , chemical name is 4-methylcoumarin-7-mercapto-2-chlorobenzoate.

[0069] The nut aroma compound is prepared by the following steps:

[0070] S1. Take 1.38 kg of salicylic acid, 2 L of chloroform and 1.46 L of thionyl chloride, add salicylic acid and chloroform into a reaction kettle and mix well, place in an ice-water bath, then add thionyl chloride into the reaction kettle and heat to 50° C. to react for 5 h, return to room temperature, and obtain a 2 mol / L o-chlorobenzoyl chloride chloroform solution for standby use;

[0071] S2, take 59.2mL 7-mercapto-4-methylcoumarin and 30g anhydrous magnesium sulfate, take 200mL of the 2mol / L chlorobenzoyl chloride chloroform solution obtained in step S1, add it to a reactor and place it in an ice-water bath, slowly add 7-mercapto-4-methylcoumarin dropwise to the reactor, and pass the generated tail gas into a 10% sodium hydroxide aqueous solution for absorption, react at room temperature for 5h, in an ice-water bath, add 100mL of a 10% sodium carbonate aqueous solution to the reactor, stir until the solution is no longer bubbling, transfer the liquid into a separatory funnel, discard the aqueous phase, add an appropriate amount of anhydrous magnesium sulfate to the organic phase, stir and mix, let stand for 24h, use a rotary evaporator, at 30°C and 500Pa pressure, recover the dichloromethane in the organic phase, and then collect the fraction with a liquid temperature of 138-143°C at a pressure of 350Pa to obtain a light yellow liquid, which is a nut aroma compound.

[0072] A nutty coffee aroma base comprises the following raw materials by weight: 5.5 mL of 4-methylcoumarin-7-mercapto 2-chlorobenzoate, 2.6 mL of furfurylthiol, 1.3 mL of acetylpyrazine, 0.3 mL of 2,5-dimethylpyrazine, 0.5 mL of 2,6-dimethylpyrazine, 0.2 mL of 2,3,5-trimethylpyrazine, 0.1 mL of tetramethylpyrazine, 8.6 mL of isoeugenol, 4.3 mL of ethyl crotonate, 11.6 mL of furfuryl alcohol, 1.8 mL of 2-acetylfuran, 3.2 mL of furfural and 60 mL of anhydrous ethanol.

[0073] The nutty coffee aroma base is prepared by the following steps:

[0074] 1) Weigh the raw materials according to weight and set aside;

[0075] 2) Add the above raw materials into a reaction device, mix, and shake repeatedly to obtain a nutty coffee aroma base.

[0076] The gas chromatogram of the obtained o-chlorobenzoic acid 4-methylcoumarin-7-mercapto ester is as follows: Figure 1 shown.

[0077] Aroma evaluation:

[0078] Five perfumers with more than five years of work experience were invited to make the following evaluations on the aroma of 4-methylcoumarin-7-mercapto-2-chlorobenzoate: Among them, five perfumers believed that the compound exhibited the characteristic aroma of coffee.

[0079] The above embodiments are preferred implementation schemes of the present invention. In addition, the present invention may also be implemented in other ways. Any obvious replacement without departing from the concept of the present invention is within the protection scope of the present invention.

Claims

1. A nut aroma compound, characterized in that: It has the following structural formula: , chemical name is 4-methylcoumarin-7-mercapto-2-chlorobenzoate.

2. A method for preparing a nut aroma compound as claimed in claim 1, characterized in that: The steps include: S1. Take salicylic acid, chloroform and thionyl chloride, add salicylic acid and chloroform into a reaction kettle and mix them evenly, place in an ice water bath, then add thionyl chloride into the reaction kettle to react, and return to room temperature to obtain a chloroform solution of o-chlorobenzoyl chloride for standby use; S2, take 7-mercapto-4-methylcoumarin and anhydrous magnesium sulfate, add the chloroform solution of o-chlorobenzoyl chloride obtained in step S1 into a reactor and place it in an ice-water bath, slowly add 7-mercapto-4-methylcoumarin dropwise into the reactor, pass the generated tail gas into a sodium hydroxide aqueous solution for absorption, react at room temperature for 3-8 hours, add a certain amount of sodium carbonate aqueous solution to the reactor in an ice-water bath, stir until the solution no longer bubbles, transfer the liquid into a separatory funnel, discard the aqueous phase, add an appropriate amount of anhydrous magnesium sulfate to the organic phase, stir and mix, let stand for 20-28 hours, rotary evaporate, recover the dichloromethane in the organic phase, and then distill under reduced pressure to obtain a light yellow liquid, which is a nut aroma compound.

3. The method for preparing a nut aroma compound according to claim 2, characterized in that: In step S1, the weight ratio of salicylic acid, chloroform and thionyl chloride is 1.36-1.46:2.6-3.6:2.0-3.

0.

4. The method for preparing a nut aroma compound according to claim 2, characterized in that: In step S2, the volume ratio of the chloroform solution of 7-mercapto-4-methylcoumarin and o-chlorobenzoyl chloride is 0.4-0.8:1.5-2.

5.

5. The method for preparing a nut aroma compound according to claim 2, characterized in that: In step S2, the volume ratio of the 7-mercapto-4-methylcoumarin to the sodium carbonate aqueous solution is 0.4-0.8:0.8-1.

2.

6. The method for preparing a nut aroma compound according to claim 2, characterized in that: In step S2, the mass concentration of the sodium hydroxide aqueous solution is 8-12%; the mass concentration of the sodium carbonate aqueous solution is 8-12%.

7. The method for preparing a nut aroma compound according to claim 2, characterized in that: In step S2, when recovering dichloromethane in the organic phase, the temperature is controlled at 25-35° C. and the pressure is controlled at 450-550 Pa.

8. The method for preparing a nut aroma compound according to claim 2, characterized in that: In step S2, during the reduced pressure distillation, under the condition of a pressure of 300-400 Pa, a fraction with a liquid temperature of 138-143° C. is collected.

9. A nutty coffee aroma base, characterized by: The invention comprises the following raw materials in parts by weight: 4-7 parts of 4-methylcoumarin-7-mercaptolate o-chlorobenzoate, 1-4 parts of furfurylthiol, 1-3 parts of acetylpyrazine, 0.1-0.5 parts of 2,5-dimethylpyrazine, 0.3-0.8 parts of 2,6-dimethylpyrazine, 0.1-0.5 parts of 2,3,5-trimethylpyrazine, 0.05-0.15 parts of tetramethylpyrazine, 7-11 parts of isoeugenol, 3-6 parts of ethyl crotonate, 10-14 parts of furfuryl alcohol, 1.4-2.2 parts of 2-acetylfuran, 3.0-4.0 parts of furfural and 55-65 parts of anhydrous ethanol.

10. The nutty coffee aroma base according to claim 9, characterized in that: The nutty coffee aroma base is prepared by the following steps: 1) Weigh the raw materials according to weight and set aside; 2) Add the above raw materials into a reaction device, mix, and shake repeatedly to obtain a nutty coffee aroma base.

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