Berry aroma compound and preparation method thereof and blackcurrant essence

Abstract

The present invention relates to the technical field of spices, and in particular to a berry aroma compound and a preparation method thereof and a blackcurrant flavor, wherein the berry aroma compound has the following structural formula: chemical name is 4-methyl-3-pentenoic acid 4-methyl-5-thiazole ethanol ester. The compound of the present invention has an obvious berry-like fruity aroma, and its aroma is obvious, the fragrance lasts for a long time, and the fidelity of the flavor quality is improved, and it has a wide range of application prospects; and the preparation method of the berry aroma compound 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, and the berry aroma compound prepared at the same time has a fruity aroma similar to that of berries, and has potential application value in daily chemicals such as aromatherapy; the blackcurrant flavor added with the berry aroma compound has a natural berry aroma, and has good practicality in the application of flavor formulas.

Description

Technical Field

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

[0002] Compounds with berry aroma are widely used in flavors to prepare pleasant berry flavors. The raw materials commonly used to prepare berry flavors are mainly synthetic spices such as 2-methyl-2-pentenoic acid, leaf alcohol, furanol, and ethyl hexanoate. If these spices are used alone, they do not have the obvious characteristic aroma of berries. Perfumers need to have mature perfumery skills to prepare flavors that match the berry taste experience. Therefore, the development of a compound with a distinct berry-like fruity aroma can significantly reduce the difficulty of preparing berry flavors, improve the fidelity of flavor quality, and has broad application prospects. Summary of the invention

[0003] In order to overcome the shortcomings and deficiencies in the prior art, the purpose of the present invention is to provide a berry aroma compound, which has a distinct berry-like fruity aroma, a distinct aroma, a long lasting aroma, improves the authenticity of the flavor quality, and has broad application prospects.

[0004] Another object of the present invention is to provide a method for preparing a berry aroma compound, 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 berry aroma compound has a natural berry aroma and is very practical in the application of flavor formulations.

[0005] Another object of the present invention is to provide a blackcurrant flavor, which is added with berry aroma compounds so that the final flavor has a berry aroma and has good practicality.

[0006] The object of the present invention is achieved by the following technical solution: A berry aroma compound has the following structural formula: , chemical name is 4-methyl-3-pentenoic acid 4-methyl-5-thiazolylethanol ester.

[0007] The compound of the present invention has obvious berry-like fruit aroma, has a distinct aroma, lasts for a long time, improves the authenticity of the essence quality, and has broad application prospects.

[0008] The present invention also provides a method for preparing a berry aroma compound, which is prepared by the following steps:

[0009]

[0010] S1, take 4-methyl-3-pentenoic acid, dichloromethane and dichlorothionyl, add 4-methyl-3-pentenoic acid and dichloromethane to a reactor in sequence, mix well and then cool to -8~-0°C, add dichlorothionyl dropwise to the reactor while stirring to react for 4-10h, then add an appropriate amount of sodium chloride solution, stir well and let stand, collect the lower organic phase in the reactor, concentrate under reduced pressure to recover dichloromethane, collect the fraction with a vapor temperature of 93-97°C at a pressure of 480-520Pa, and obtain 4-methyl-3-pentenoyl chloride for standby use;

[0011]

[0012] S2. Take 4-methyl-5-thiazoleethanol and 4-methyl-3-pentenoyl chloride, add 4-methyl-5-thiazoleethanol into a reactor, cool to -8~-0°C, then slowly add 4-methyl-3-pentenoyl chloride into the reactor and react for 2-6h. After the reaction is completed, perform reduced pressure distillation, collect the fraction with a vapor temperature of 132-137°C at a pressure of 270-290Pa, and obtain 4-methyl-3-pentenoic acid 4-methyl-5-thiazoleethanol ester.

[0013] The berry aroma compound in the present invention is prepared by adopting the above method, and the berry aroma compound prepared by the above method has a strong berry aroma, a distinct aroma, a long lasting aroma, and has potential application value in daily chemical products such as aromatherapy; the preparation method is simple and efficient, easy to operate and control, the product quality is high, the cost is low, and it is conducive to industrial production. At the same time, the berry aroma compound prepared has a natural berry aroma and has good practicality in the application of flavor formulas.

[0014] Preferably, in step S1, the weight ratio of the 4-methyl-3-pentenoic acid, dichloromethane and thionyl chloride is 3.0-3.8:8.5-9.5:3.0-4.0.

[0015] Preferably, in step S1, a sodium chloride solution with a mass concentration of 3-7% is used.

[0016] Preferably, in step S2, the weight ratio of the 4-methyl-5-thiazoleethanol to the 4-methyl-3-pentenoyl chloride is 1.2-1.8:1.0-1.5.

[0017] Preferably, in step S2, an appropriate amount of catalyst is also added, and the catalyst is cyclohexane.

[0018] The invention also provides a blackcurrant essence, which comprises the following raw materials in parts by weight: 8.3-8.8 parts of glycerol, 28-34 parts of propylene glycol, 4.4-5.4 parts of ethyl maltol, 1.0-1.6 parts of leaf alcohol, 7-8 parts of 2-methyl-2-pentenoic acid, 11-13 parts of 4-methyl-3-pentenoic acid 4-methyl-5-thiazoleethanol ester, 5.0-5.6 parts of raspberry ketone, 16.5-17.5 parts of neotame, 0.2-0.8 parts of peach aldehyde, 0.3-0.8 parts of gamma-nonalactone, 2.4-3.0 parts of natural menthol, 0.1-0.3 parts of cinnamaldehyde, 0.2-0.8 parts of furanone acetate, 1.0-1.6 parts of ethyl caproate, 0.3-1.0 parts of allyl caproate, 0.8-1.6 parts of hexyl acetate and 4.0-4.8 parts of furanone acetate.

[0019] Preferably, the blackcurrant essence 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 the reaction device, mix, and shake repeatedly to obtain black currant essence.

[0022] The essence of the present invention is added with berry aroma compounds so that the finally prepared essence has a berry aroma similar to that of berry, and has good practicality.

[0023] The beneficial effects of the present invention are: the compound of the present invention has obvious berry-like fruity aroma, the aroma is obvious, the aroma lasts for a long time, the authenticity of the flavor quality is improved, and it has a wide application prospect.

[0024] The preparation method of the berry aroma compound of the present invention is simple and efficient, the operation and control are convenient, the produced product is high in quality, the cost is low, and it is conducive to industrial production. At the same time, the prepared berry aroma compound has a berry-like fruit aroma and has potential application value in daily chemicals such as aromatherapy. The blackcurrant essence added with the berry aroma compound has a berry-like aroma and has good practicality. BRIEF DESCRIPTION OF THE DRAWINGS

[0025] Figure 1 It is a gas chromatogram of 4-methyl-3-pentenoic acid 4-methyl-5-thiazoleethanol ester 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 berry aroma compound having the following structural formula: , chemical name is 4-methyl-3-pentenoic acid 4-methyl-5-thiazolylethanol ester.

[0029] The berry aroma compound is prepared by the following steps:

[0030] S1, take 4-methyl-3-pentenoic acid, dichloromethane and dichlorothionyl, add 4-methyl-3-pentenoic acid and dichloromethane to a reactor in sequence, mix well and then cool to -8°C, add dichlorothionyl dropwise to the reactor while stirring to react for 4h, then add 3L of sodium chloride solution, stir well and let stand, collect the lower organic phase in the reactor, concentrate under reduced pressure to recover dichloromethane, collect the fraction with a vapor temperature of 93-97°C at a pressure of 480Pa, and obtain 4-methyl-3-pentenoyl chloride for standby use;

[0031] S2. Take 4-methyl-5-thiazoleethanol and 4-methyl-3-pentenoyl chloride, add 4-methyl-5-thiazoleethanol into the reactor, cool to -8°C, and then slowly add 4-methyl-3-pentenoyl chloride into the reactor to react for 2 hours. After the reaction is completed, distill under reduced pressure, collect the fraction with a vapor temperature of 132-137°C at a pressure of 270Pa, and obtain 4-methyl-3-pentenoic acid 4-methyl-5-thiazoleethanol ester.

[0032] In step S1, the weight ratio of the 4-methyl-3-pentenoic acid, dichloromethane and thionyl chloride is 3.0:8.5:3.0.

[0033] In step S1, a sodium chloride solution with a mass% of 3% is used.

[0034] In step S2, the weight ratio of the 4-methyl-5-thiazoleethanol and 4-methyl-3-pentenoyl chloride is 1.2:1.0.

[0035] In step S2, an appropriate amount of catalyst is also added, and the catalyst is cyclohexane.

[0036] A blackcurrant flavor comprises the following raw materials in parts by weight: 8.3 parts of glycerin, 28 parts of propylene glycol, 4.4 parts of ethyl maltol, 1.0 parts of leaf alcohol, 5.0 parts of oleic acid, 16.5 parts of neotame, 0.2 parts of peach aldehyde, 0.3 parts of γ-nonalactone, 2.4 parts of natural menthol, 0.1 parts of cinnamaldehyde, 0.2 parts of furfural, 1.0 parts of ethyl caproate, 0.3 parts of allyl caproate, 0.8 parts of hexyl acetate and 4.0 parts of furanone acetate.

[0037] The blackcurrant essence 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 the reaction device, mix, and shake repeatedly to obtain black currant essence.

[0040] Example 2

[0041] A berry aroma compound having the following structural formula: , chemical name is 4-methyl-3-pentenoic acid 4-methyl-5-thiazolylethanol ester.

[0042] The berry aroma compound is prepared by the following steps:

[0043] S1, take 4-methyl-3-pentenoic acid, dichloromethane and dichlorothionyl, add 4-methyl-3-pentenoic acid and dichloromethane to a reactor in sequence, mix well and cool to -4°C, add dichlorothionyl dropwise to the reactor while stirring to react for 8h, then add 3L of sodium chloride solution, stir well and let stand, collect the lower organic phase in the reactor, concentrate under reduced pressure to recover dichloromethane, collect the fraction with a vapor temperature of 93-97°C at a pressure of 500Pa, and obtain 4-methyl-3-pentenoyl chloride for standby use;

[0044] S2. Take 4-methyl-5-thiazoleethanol and 4-methyl-3-pentenoyl chloride, add 4-methyl-5-thiazoleethanol into the reactor, cool to -4°C, and then slowly add 4-methyl-3-pentenoyl chloride into the reactor to react for 3 hours. After the reaction is completed, distill under reduced pressure, collect the fraction with a vapor temperature of 132-137°C at a pressure of 280Pa, and obtain 4-methyl-3-pentenoic acid 4-methyl-5-thiazoleethanol ester.

[0045] In step S1, the weight ratio of the 4-methyl-3-pentenoic acid, dichloromethane and dithionyl chloride is 3.4:9.0:3.5.

[0046] In step S1, a sodium chloride solution with a mass% of 5% is used.

[0047] In step S2, the weight ratio of the 4-methyl-5-thiazoleethanol and 4-methyl-3-pentenoyl chloride is 1.6:1.3.

[0048] In step S2, an appropriate amount of catalyst is also added, and the catalyst is cyclohexane.

[0049] A blackcurrant flavor comprises the following raw materials in parts by weight: 8.5 parts of glycerol, 31.5 parts of propylene glycol, 4.8 parts of ethyl maltol, 1.2 parts of leaf alcohol, 7.3 parts of 2-methyl-2-pentenoic acid, 12.6 parts of 4-methyl-3-pentenoic acid 4-methyl-5-thiazoleethanol ester, 5.3 parts of raspberry ketone, 16.9 parts of neotame, 0.4 parts of peach aldehyde, 0.6 parts of gamma-nonalactone, 2.7 parts of natural menthol, 0.2 parts of cinnamaldehyde, 0.6 parts of furfural, 1.2 parts of ethyl caproate, 0.7 parts of allyl caproate, 1.2 parts of hexyl acetate and 4.3 parts of furanone acetate.

[0050] The blackcurrant essence 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 the reaction device, mix, and shake repeatedly to obtain black currant essence.

[0053] Example 3

[0054] A berry aroma compound having the following structural formula: , chemical name is 4-methyl-3-pentenoic acid 4-methyl-5-thiazolylethanol ester.

[0055] The berry aroma compound is prepared by the following steps:

[0056] S1, take 4-methyl-3-pentenoic acid, dichloromethane and dichlorothionyl, add 4-methyl-3-pentenoic acid and dichloromethane to a reactor in sequence, mix well and cool to -1°C, add dichlorothionyl dropwise to the reactor while stirring, react for 10 hours, then add 3L of sodium chloride solution, stir well and let stand, collect the lower organic phase in the reactor, concentrate under reduced pressure to recover dichloromethane, collect the fraction with a vapor temperature of 97°C at a pressure of 520Pa, and obtain 4-methyl-3-pentenoyl chloride for standby use;

[0057] S2. Take 4-methyl-5-thiazoleethanol and 4-methyl-3-pentenoyl chloride, add 4-methyl-5-thiazoleethanol into the reactor, cool to -1°C, and then slowly add 4-methyl-3-pentenoyl chloride into the reactor to react for 6 hours. After the reaction is completed, distill under reduced pressure, collect the fraction with a vapor temperature of 137°C at a pressure of 290Pa, and obtain 4-methyl-5-thiazoleethanol 4-methyl-3-pentenoate.

[0058] In step S1, the weight ratio of the 4-methyl-3-pentenoic acid, dichloromethane and dithionyl chloride is 3.8:9.5:4.0.

[0059] In step S1, a sodium chloride solution with a mass% of 7% is used.

[0060] In step S2, the weight ratio of the 4-methyl-5-thiazoleethanol and 4-methyl-3-pentenoyl chloride is 1.8:1.5.

[0061] In step S2, an appropriate amount of catalyst is also added, and the catalyst is cyclohexane.

[0062] A blackcurrant flavor comprises the following raw materials in parts by weight: 8.8 parts of glycerol, 34 parts of propylene glycol, 5.4 parts of ethyl maltol, 1.6 parts of leaf alcohol, 8 parts of 2-methyl-2-pentenoic acid, 13 parts of 4-methyl-3-pentenoic acid 4-methyl-5-thiazoleethanol ester, 5.6 parts of raspberry ketone, 17.5 parts of neotame, 0.8 parts of peach aldehyde, 0.8 parts of gamma-nonalactone, 3.0 parts of natural menthol, 0.3 parts of cinnamaldehyde, 0.8 parts of furfural, 1.6 parts of ethyl caproate, 1.0 parts of allyl caproate, 1.6 parts of hexyl acetate and 4.8 parts of furanone acetate.

[0063] The blackcurrant essence 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 the reaction device, mix, and shake repeatedly to obtain black currant essence.

[0066] Example 4

[0067] A berry aroma compound having the following structural formula: , chemical name is 4-methyl-3-pentenoic acid 4-methyl-5-thiazolylethanol ester.

[0068] The berry aroma compound is prepared by the following steps:

[0069] S1, take 3.42kg of 4-methyl-3-pentenoic acid, 6.8L of dichloromethane and 2.2L of dithionyl chloride, add 4-methyl-3-pentenoic acid and dichloromethane to a reactor in sequence, mix well and cool to -5°C, add dichlorothionyl chloride dropwise to the reactor while stirring and react for 8h, then add 3L of 5% sodium chloride solution by mass, stir well and let stand, collect the lower organic phase in the reactor, concentrate under reduced pressure to recover dichloromethane, collect the fraction with a vapor temperature of 93-97°C at a pressure of 500Pa, and obtain 4-methyl-3-pentenoyl chloride for standby use;

[0070] S2. Take 1.43 kg of 4-methyl-5-thiazoleethanol and 1.33 kg of 4-methyl-3-pentenoyl chloride, add 4-methyl-5-thiazoleethanol into the reactor, cool to -5°C, and then slowly add 4-methyl-3-pentenoyl chloride into the reactor to react for 3 hours. After the reaction is completed, distill under reduced pressure, collect the fraction with a vapor temperature of 132-137°C at a pressure of 280 Pa to obtain 4-methyl-3-pentenoic acid 4-methyl-5-thiazoleethanol ester.

[0071] In step S2, an appropriate amount of catalyst is also added, and the catalyst is cyclohexane.

[0072] A blackcurrant flavor comprises the following raw materials by weight: 8.5 g of glycerol, 31.5 g of propylene glycol, 4.8 g of ethyl maltol, 1.2 g of leaf alcohol, 7.3 g of 2-methyl-2-pentenoic acid, 12.6 g of 4-methyl-3-pentenoic acid 4-methyl-5-thiazoleethanol ester, 5.3 g of raspberry ketone, 16.9 g of neotame, 0.4 g of peach aldehyde, 0.6 g of γ-nonalactone, 2.7 g of natural menthol, 0.2 g of cinnamaldehyde, 0.6 g of furfural, 1.2 g of ethyl caproate, 0.7 g of allyl caproate, 1.2 g of hexyl acetate and 4.3 g of furanone acetate.

[0073] The blackcurrant essence 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 the reaction device, mix, and shake repeatedly to obtain black currant essence.

[0076] The mass spectrum of the obtained 4-methyl-3-pentenoic acid 4-methyl-5-thiazole ethanol ester is as follows Figure 1 As shown, the mass spectrometry data are as follows:

[0077] MS (ESI, m / z) 262.1 (M + Na + );Theoretical calculation data of high resolution electrospray ionization mass spectrometry is [C 12 H 17 NNaO2S] + (M + Na + ) 262.0782, the actual measured value is 262.0806.

[0078] Aroma evaluation:

[0079] Five perfumers with more than five years of work experience were invited to give the following evaluations on the aroma of the compound: Among them, five perfumers believed that the compound exhibited a distinct berry-like aroma.

[0080] 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 berry aroma compound, characterized in that: It has the following structural formula: , chemical name is 4-methyl-3-pentenoic acid 4-methyl-5-thiazolylethanol ester.

2. A method for preparing a berry aroma compound, characterized in that: Prepared by the following steps: S1, take 4-methyl-3-pentenoic acid, dichloromethane and dichlorothionyl, add 4-methyl-3-pentenoic acid and dichloromethane to a reactor in sequence, mix well and then cool to -8~-0°C, add dichlorothionyl dropwise to the reactor while stirring to react for 4-10h, then add an appropriate amount of sodium chloride solution, stir well and let stand, collect the lower organic phase in the reactor, concentrate under reduced pressure to recover dichloromethane, and perform reduced pressure distillation to collect the fractions to obtain 4-methyl-3-pentenoyl chloride for standby use; S2. Take 4-methyl-5-thiazoleethanol and 4-methyl-3-pentenoyl chloride, add 4-methyl-5-thiazoleethanol into the reaction kettle, cool it to -8~-0°C, and then slowly add 4-methyl-3-pentenoyl chloride into the reaction kettle to react for 2-6h. After the reaction is completed, distill under reduced pressure and collect the fractions to obtain 4-methyl-3-pentenoic acid 4-methyl-5-thiazoleethanol ester.

3. The method for preparing a berry aroma compound according to claim 2, characterized in that: In step S1, during the reduced pressure distillation, a fraction with a vapor temperature of 93-97° C. is collected at a pressure of 480-520 Pa.

4. The method for preparing a berry aroma compound according to claim 2, characterized in that: In step S2, during the reduced pressure distillation, a fraction with a vapor temperature of 132-137° C. is collected at a pressure of 270-290 Pa.

5. The method for preparing a berry aroma compound according to claim 2, characterized in that: In step S1, the weight ratio of the 4-methyl-3-pentenoic acid, dichloromethane and thionyl chloride is 3.0-3.8:8.5-9.5:3.0-4.

0.

6. The method for preparing a berry aroma compound according to claim 2, characterized in that: In step S1, a sodium chloride solution with a mass concentration of 3-7% is used.

7. The method for preparing a berry aroma compound according to claim 2, characterized in that: In step S2, the weight ratio of the 4-methyl-5-thiazoleethanol and 4-methyl-3-pentenoyl chloride is 1.2-1.8:1.0-1.

5.

8. The method for preparing a berry aroma compound according to claim 2, characterized in that: In step S2, an appropriate amount of catalyst is also added, and the catalyst is cyclohexane.

9. A blackcurrant essence, characterized in that: The invention comprises the following raw materials in parts by weight: 8.3-8.8 parts of glycerol, 28-34 parts of propylene glycol, 4.4-5.4 parts of ethyl maltol, 1.0-1.6 parts of leaf alcohol, 7-8 parts of 2-methyl-2-pentenoic acid, 11-13 parts of 4-methyl-3-pentenoic acid 4-methyl-5-thiazoleethanol ester, 5.0-5.6 parts of raspberry ketone, 16.5-17.5 parts of neotame, 0.2-0.8 parts of peach aldehyde, 0.3-0.8 parts of gamma-nonalactone, 2.4-3.0 parts of natural menthol, 0.1-0.3 parts of cinnamaldehyde, 0.2-0.8 parts of furanone acetate, 1.0-1.6 parts of ethyl caproate, 0.3-1.0 parts of allyl caproate, 0.8-1.6 parts of hexyl acetate and 4.0-4.8 parts of furanone acetate.

10. A blackcurrant essence according to claim 9, characterized in that: The blackcurrant essence is prepared by the following steps: 1) Weigh the raw materials according to weight and set aside; 2) Add the above raw materials into the reaction device, mix, and shake repeatedly to obtain black currant essence.

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