A decenoate compound, a preparation method and application thereof

Abstract

The present application relates to the technical field of chemical essence and flavor, and particularly relates to a decenoic acid ester compound, a preparation method and application thereof, and comprises the following steps: (1) preparing 2-(4-methyl-benzylidene) heptanal: under the condition of an inorganic alkaline reagent, p-methylbenzaldehyde and n-heptanal are subjected to aldol condensation reaction to synthesize 2-(4-methyl-benzylidene) heptanal; (2) preparing 2-(4-methyl-benzylidene) heptyl alcohol: under the condition of a reducing agent, 2-(4-methyl-benzylidene) heptanal is reduced to 2-(4-methyl-benzylidene) heptyl alcohol; (3) preparing 5-decenoic acid 2-(4-methyl-benzylidene) heptyl alcohol ester: under the catalysis of an acid, 5-decenoic acid and 2-(4-methyl-benzylidene) heptyl alcohol are subjected to esterification to synthesize 5-decenoic acid 2-(4-methyl-benzylidene) heptyl alcohol ester. The compound in the present application has jasmine aroma and milk aroma, has elegant aroma, has long-lasting aroma, and has important use in the field of daily chemical flavoring.

Description

TECHNICAL FIELD

[0001] The present application relates to the technical field of chemical flavor and fragrance, in particular to a decenoic acid ester compound and a preparation method and application thereof. BACKGROUND

[0002] Flavor and fragrance can impart special fragrance to daily products, so that daily products have pleasant fragrance characteristics on the basis of practicality.

[0003] Jasmine is one of the most favorite flowers due to its elegant fragrance. In the flavor industry, jasmine fragrance belongs to typical floral fresh notes, and the fragrance is delicate and transparent, and has a fresh feeling. Therefore, jasmine flavor has great demand in the daily chemical product field. At present, the jasmine flavor sold on the market still has some difference from the fragrance of jasmine flowers. Moreover, most flavors are volatile, and have short fragrance retention time during use. SUMMARY

[0004] Based on this, the present application provides a decenoic acid ester compound and a preparation method and application thereof. The decenoic acid ester compound has jasmine fragrance, and has milk fragrance notes, and the fragrance is elegant, and has long fragrance retention time.

[0005] A decenoic acid ester compound has the following structural formula:

[0006]

[0007] The chemical name of the compound is 5-decenoic acid 2-(4-methyl-benzylidene) heptanol ester, the molecular formula is C 25 H 38 O2, and the molecular weight is 370. The traditional flavor fragrance is relatively single. The compound has jasmine fragrance, and also has milk fragrance notes, and has long fragrance retention time, and can be widely used in flavor such as shampoo, shower gel and perfume, and has wide application prospect in daily chemical flavoring field.

[0008] Further, a preparation method of the decenoic acid ester compound is provided, comprising the following steps:

[0009] (1) preparing 2-(4-methyl-benzylidene) heptanal:

[0010] In the reaction kettle, add inorganic alkaline reagent, ethanol solution, after the inorganic alkaline reagent is dissolved in the ethanol solution, add p-methyl benzaldehyde and antioxidant, water bath preservation 30-40℃, uniform speed drop adds normal heptanal, after drop adding is finished, continue stirring 15-25min, add acetic acid to adjust the pH of the system to 7, heat and reduce pressure to recover ethanol and p-methyl benzaldehyde, after recovery, cool to 35-45℃, after cooling, wash with saturated brine, then adjust the pH of the system to 8 with saturated brine and sodium carbonate solution, finally distill the organic layer obtained, get light yellow transparent liquid, that is 2-(4-methyl-benzylidene) heptanal;

[0011] (2) Preparation of 2-(4-methyl-benzylidene) heptyl alcohol:

[0012] The alkaline aqueous solution containing reducing agent is configured, 2-(4-methyl-benzylidene) heptanal and ethanol solution are added in the reaction kettle, the prepared alkaline aqueous solution containing reducing agent is added dropwise, washed with 3-6% salt water multiple times, and the organic layer obtained by distillation and separation is obtained. 2-(4-methyl-benzylidene) heptyl alcohol is obtained.

[0013] (3) Preparation of 5-decenoic acid 2-(4-methyl-benzylidene) heptyl ester:

[0014] In the reaction kettle, 5-decenoic acid, 2-(4-methyl-benzylidene) heptyl alcohol, catalyst and organic solution are added in turn, heated to 85-90℃, refluxed for 7-9h, after reaction, washed with 3-6% salt water multiple times, recovered the organic solution in the organic layer obtained by separation, and distilled after recovery. Light yellow transparent liquid, that is 5-decenoic acid 2-(4-methyl-benzylidene) heptyl ester.

[0015] Further, the molar ratio of the amount of p-methyl benzaldehyde to normal heptanal in step (1) is 1.2-1.8:1. The hydroxy aldehyde condensation reaction of p-methyl benzaldehyde and normal heptanal is controlled, and the above amount ratio can ensure that the excess of methyl benzaldehyde can promote the forward progress of the hydroxy aldehyde condensation reaction to a certain extent, and can reduce the generation of by-products.

[0016] Further, the inorganic alkaline reagent in step (1) can be any one of potassium hydroxide, sodium hydroxide and calcium hydroxide. The inorganic alkaline reagent is preferably potassium hydroxide, the molar ratio of the amount of potassium hydroxide to normal heptanal is 0.3-0.5:1, and the molar ratio of the amount of ethanol to potassium hydroxide is 8-15:1.

[0017] Further, the antioxidant in step (1) can be at least one of BHT and diphenylamine. The antioxidant is preferably a combination of BHT and diphenylamine, the molar ratio of the amount of BHT, diphenylamine to normal heptanal is 0.002-0.005:0.002-0.005:1, and the addition of antioxidant can better improve the conversion rate of the reaction.

[0018] Further, the time for dropping the n-heptanal in step (1) is 5.5-6.5h. The reaction of p-tolualdehyde and n-heptanal is a Claisen-Schmidt condensation reaction, in which p-tolualdehyde and n-heptanal are condensed in the presence of a catalyst to form an α,β-unsaturated aldehyde with high chemical selectivity. The dropping speed of n-heptanal has certain influence on the conversion rate. The dropping time of n-heptanal is 5.5-6.5h, and the reaction time is 15-30min. The actual time used can be selected according to the amount of reactant.

[0019] Further, the distillation in step (1) is a reduced pressure distillation. In the reduced pressure distillation, the distillate with a vapor temperature of 130-135℃ is collected under a pressure of 250Pa.

[0020] Further, the reducing agent in step (2) can be any one of sodium borohydride and potassium borohydride. The reducing agent is preferably sodium borohydride. The molar ratio of the amount of sodium borohydride to the amount of 2-(4-methyl-benzylidene)heptanal is 0.3-0.35:1.

[0021] Further, the sodium borohydride is configured into an alkaline aqueous solution. Sodium borohydride is easily decomposed to form borane and hydrogen in an acidic and neutral aqueous solution. In an alkaline solution, the presence of hydroxyl ions inhibits the hydrolysis equilibrium, and sodium borohydride is in a stable state, which is conducive to the contact of sodium borohydride with the reactants and accelerates the reaction speed.

[0022] Further, after the 2-(4-methyl-benzylidene)heptanal and the ethanol solution are added in step (2), the solution is cooled to 8-12℃, and the alkaline aqueous solution of sodium borohydride is dropped for 1.5-2h. Dropping sodium borohydride at low temperature is convenient to operate and easy to control the reaction.

[0023] Further, the molar ratio of the amount of ethanol to the amount of 2-(4-methyl-benzylidene)heptanal is 4-4.5:1.

[0024] Further, the distillation in step (2) is a reduced pressure distillation. In the reduced pressure distillation, the distillate with a vapor temperature of 140-145℃ is collected under a pressure of 250Pa.

[0025] Further, the molar ratio of the amount of 5-decenoic acid to the amount of 2-(4-methyl-benzylidene)heptanol in step (3) is 1-1.2:1. The ratio of the substrates in the esterification reaction affects the reaction rate. Excessive 5-decenoic acid can improve the conversion rate of 2-(4-methyl-benzylidene)heptanol, and thus improve the yield of decenoic acid ester compound.

[0026] Further, the catalyst in step (3) can be any one of p-toluenesulfonic acid, concentrated sulfuric acid, concentrated hydrochloric acid, and the organic solution can be any one of cyclohexane, toluene. The catalyst is preferably p-toluenesulfonic acid, and the organic solution is preferably cyclohexane. The molar ratio of p-toluenesulfonic acid to the amount of 2-(4-methyl-benzylidene) heptanol is 0.01-0.02:1, and the molar ratio of cyclohexane to the amount of 2-(4-methyl-benzylidene) heptanol is 3.5-4:1. As an acid catalyst, the carbonyl oxygen of 5-decenoic acid is protonated under acidic conditions, enhancing the electrophilicity of the carbonyl carbon, which accelerates the reaction rate. The carbonyl carbon of 5-decenoic acid is subjected to nucleophilic attack by the alcohol, producing a tetrahedral intermediate with two hydroxyl groups. After proton transfer to one of the two equivalent hydroxyl groups, the group is converted into a good leaving group, and after the group is removed, the carbonyl group is restored and forms an ester.

[0027] Further, the distillation in step (3) is reduced pressure distillation. When reduced pressure distillation is performed, the fraction with a vapor temperature of 190-196℃ is collected at a pressure of 200 Pa.

[0028] Further, the application also provides an application of the decenoic acid ester compound, which comprises the decenoic acid ester compound described above or the decenoic acid ester compound prepared by the preparation method of the decenoic acid ester compound described above, and is applied to daily chemical perfuming as a fragrance.

[0029] Further, the decenoic acid ester compound described above is applied to a shampoo fragrance, and the amount is as follows:

[0030]

[0031]

[0032] Further, the decenoic acid ester compound described above is applied to a shower gel fragrance, and the amount is as follows:

[0033] No. Raw material name Amount (%) 1 Myroxin 0.1-0.2 2 Benzene ethyl dimethyl acetal 0.2-0.25 3 Citral 0.2-0.3 4 Guerlain liquid 0.45-0.6 5 Indole 0.35-0.55 6 2-(4-methyl-benzylidene) heptanol ester of 5-decenoic acid 8-10 7 Tricyclohexyl propionate 1.5-2 8 Geraniol 980 2-3 9 Linalool 3-4 10 Lily flower base 3-4 11 Benzyl acetate 4-7 12 Lilial 6--8 13 Phenylethyl alcohol 10-14 14 HCA 10-15 15 Vanillin 10-15 16 Dipropylene glycol 20-22 Total 100

[0034] Further, the decenoic acid ester compound described above is applied to a shower gel fragrance, and the amount is as follows:

[0035]

[0036]

[0037] Compared with the prior art, the application has the following beneficial effects:

[0038] 1. The decenoic acid ester compound has a jasmine fragrance and a milk fragrance, and the jasmine fragrance has a fragrance retention time of more than 96h, and the milk fragrance has a fragrance retention time of more than 102h.

[0039] 2. The decenoate compound has not been launched in domestic and foreign fragrance companies, and has important use in the field of daily chemical fragrance. BRIEF DESCRIPTION OF DRAWINGS

[0040] Figure 1 Gas chromatogram of the decenoate compound prepared in Example 1. DETAILED DESCRIPTION

[0041] In order to facilitate the understanding of the present application, the present application will be described more fully below with reference to the accompanying drawings. The preferred embodiments of the present application are shown in the drawings. However, the present application can be implemented in many different forms and is not limited to the embodiments described herein. On the contrary, the purpose of providing these embodiments is to make the disclosure of the present application more thorough and comprehensive.

[0042] Unless otherwise defined, 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 application belongs. The terminology used in the description of the application herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the application.

[0043] Example 1

[0044] The preparation method of the decenoate compound of the present embodiment comprises the following steps:

[0045] (1) Preparation of 2-(4-methyl-benzylidene) heptanal:

[0046] In a 1000 mL three-necked flask equipped with a stirrer, a thermometer, a reflux condenser and a dropping funnel, 20.0 g of potassium hydroxide, 16.0 g of water and 200.0 g of ethanol were added. After the potassium hydroxide was completely dissolved, 180.0 g of p-methylbenzaldehyde, 1.0 g of BHT and 0.5 g of diphenylamine were added. The temperature of the flask was maintained at 35°C by water bath. 114.0 g of n-heptanal was added at a uniform speed for 6 hours. After the addition was completed, stirring was continued for 20 minutes. Acetic acid was added to neutralize to pH = 7. Ethanol and p-methylbenzaldehyde were recovered by heating and reducing pressure. After recovery, the temperature was cooled to 40°C, and then washed with 200.0 g of saturated brine. Then, 20.0 g of sodium carbonate and 150.0 g of saturated brine were added to neutralize to pH = 8. Finally, the organic layer obtained by liquid separation was distilled under reduced pressure. The fraction with a vapor temperature of 130-135°C was collected under a pressure of 250 Pa to obtain a light yellow transparent liquid, which was 192.5 g of 2-(4-methyl-benzylidene) heptanal with a GC content of 95%;

[0047] (2) Reduction of 2-(4-methyl-benzylidene) heptanal to 2-(4-methyl-benzylidene) heptanol

[0048] A 1000 mL reaction vessel was charged with 324.0 g of 2-(4-methyl-benzylidene)heptanal and 300.0 g of ethanol and cooled to 10°C, and then a 97.8 g aqueous solution containing 0.2 g of sodium hydroxide and 17.6 g of sodium borohydride was added dropwise over 2 h. Subsequently, the reaction mixture was washed twice with 500 mL of 5% brine, and the organic layer obtained by the liquid separation was distilled under reduced pressure. The fraction having a vapor temperature of 140-145°C was collected at 250 Pa to obtain 291.6 g of 2-(4-methyl-benzylidene)heptanol (94.5% by GC).

[0049] (3) Esterification of 2-(4-methyl-benzylidene)heptanol with 5-decenoic acid to produce a decenoic acid ester compound

[0050] A three-necked flask was sequentially charged with 182.5 g of 5-decenoic acid, 218.0 g of 2-(4-methyl-benzylidene)heptanol, 2.5 g of p-toluenesulfonic acid, and 400 mL of cyclohexane, and heated to 88°C to perform dehydration reaction under reflux for 8 h. After completion of the reaction, the reaction mixture was washed twice with 500 mL of 5% brine, and the organic layer obtained by the liquid separation was distilled under reduced pressure after recovering the cyclohexane. The fraction having a vapor temperature of 190-196°C was collected at 200 Pa to obtain 318.5 g of 2-(4-methyl-benzylidene)heptanol 5-decenoate as a pale yellow transparent liquid (93.6% by GC).

[0051] The 2-(4-methyl-benzylidene)heptanol 5-decenoate obtained in this example had the following NMR spectral characteristics:

[0052] 1 H NMR (400 MHz, CD3Cl): 7.59 (m, 2H), 7.18 (m, 2H), 6.34 (m, 1H), 5.48 (m, 2H), 4.75 (d, 2H), 2.34 (s, 3H), 2.32 (m, 2H), 2.18 (m, 6H), 1.76 (m, 2H), 1.31 (m, 4H), 1.29 (m, 6H), 0.90 (m, 6H);

[0053] 13 C NMR (100 MHz, CD3Cl): 173.1, 143.8, 137.6, 132.2, 130.7, 128.9, 128.9, 128.5, 128.5, 128.0, 123.5, 67.5, 34.1, 33.4, 33.1, 32.2, 32.1, 28.3, 26.9, 24.9, 22.8, 22.8, 21.3, 14.2, 14.1.

[0054] The mass spectrum analysis data of 5-decenoic acid 2-(4-methyl-benzylidene) heptanol ester prepared in the example is as follows:

[0055] MS (ESI, m / z) 393.28 (M+Na + ); high resolution electrospray ionization mass spectrum theoretical calculation data is [C 25 H 38 NaO2] + (M+Na + ) 393.2815, the actual measured value is 393.2810.

[0056] The gas chromatogram of 5-decenoic acid 2-(4-methyl-benzylidene) heptanol ester prepared in the example is as shown in Figure 1

[0057] As can be seen from the above experimental data, the compound prepared in Example 1 is 5-decenoic acid 2-(4-methyl-benzylidene) heptanol ester.

[0058] Example 2

[0059] The preparation method of the decenoic acid ester compound of the example comprises the following steps:

[0060] (1) Aldol condensation reaction of p-methyl benzaldehyde and n-heptanal to prepare 2-(4-methyl-benzylidene) heptanal

[0061] In a 1000 mL three-necked flask equipped with a stirrer, a thermometer, a reflux condenser and a dropping funnel, 30.0 g of potassium hydroxide, 25.0 g of water and 300.0 g of ethanol were added. After the potassium hydroxide was completely dissolved, 270.0 g of p-methyl benzaldehyde, 1.5 g of BHT and 0.8 g of diphenylamine were added. The temperature in the flask was maintained at 38°C by water bath. 170.0 g of n-heptanal was added at a constant speed for 6.5 h. After the addition was completed, the stirring was continued for 25 min. The pH was neutralized to 7 by adding acetic acid. The ethanol and p-methyl benzaldehyde were recovered by heating and reducing the pressure. After the recovery, the temperature was cooled to 40°C. The organic layer obtained by liquid separation was washed with 300.0 g of saturated brine, then neutralized to pH=8 with 30.0 g of sodium carbonate and 225.0 g of saturated brine. Finally, the organic layer obtained by liquid separation was distilled under reduced pressure. The fraction with a vapor temperature of 130-135°C was collected under a pressure of 250 Pa to obtain 228.8 g of 2-(4-methyl-benzylidene) heptanal in the form of a light yellow transparent liquid, and the GC content was 94.6%;

[0062] (2) Reduction of 2-(4-methyl-benzylidene) heptanal to 2-(4-methyl-benzylidene) heptanol

[0063] ​A 146.7 g aqueous solution containing 0.3 g of sodium hydroxide and 26.4 g of sodium borohydride was prepared, and 486.0 g of 2-(4-methyl-benzylidene)heptanal and 450.0 g of ethanol were added to a 1000 mL reaction vessel, which was cooled to 10°C, and then the above aqueous solution of sodium borohydride was added dropwise over 1.8 h. Subsequently, the reaction mixture was washed twice with 750 mL of 5% brine, and the organic layer obtained by the liquid separation was subjected to distillation under reduced pressure, and 435.4 g of 2-(4-methyl-benzylidene)heptanol was collected at 140-145°C under 250 Pa, and the GC content was 93.8%;

[0064] (3) Esterification of 2-(4-methyl-benzylidene)heptanol with 5-decylenic acid to produce a decylenic acid ester compound

[0065] A three-necked flask was sequentially charged with 275.5 g of 5-decylenic acid, 325.0 g of 2-(4-methyl-benzylidene)heptanol, 3.5 g of p-toluenesulfonic acid, and 600 mL of cyclohexane, and the mixture was heated to 90°C and refluxed for 9 h. After the reaction, the mixture was washed twice with 750 mL of 5% brine, and the organic layer obtained by the liquid separation was subjected to distillation under reduced pressure after the cyclohexane was recovered, and 470.8 g of 2-(4-methyl-benzylidene)heptanol 5-decylenate was obtained as a pale yellow transparent liquid at 190-196°C under 200 Pa, and the GC content was 92.9%.

[0066] Example 3

[0067] The method for producing the decylenic acid ester compound of the present embodiment includes the following steps:

[0068] (1) Aldol condensation of p-tolualdehyde with n-heptanal to produce 2-(4-methyl-benzylidene)heptanal

[0069] In a 1000 mL three-necked flask equipped with a stirrer, thermometer, reflux condenser and dropping funnel, 10.0 g of potassium hydroxide, 10.0 g of water and 100.0 g of ethanol were added. After the potassium hydroxide was completely dissolved, 90.0 g of p-tolualdehyde, 0.5 g of BHT and 0.2 g of diphenylamine were added. The flask was maintained at 40°C in a water bath, and 55.0 g of n-heptanal was added at a constant rate over 5.5 hours. After the addition was completed, stirring was continued for 18 minutes. The pH was adjusted to 7 by adding acetic acid, and ethanol and p-tolualdehyde were recovered by heating under reduced pressure. After the recovery was completed, the temperature was lowered to 41°C and the mixture was washed with 100.0 g of saturated brine. The pH was adjusted to 8 by adding 10.0 g of sodium carbonate and 75.0 g of saturated brine. Finally, the organic layer obtained by liquid separation was distilled under reduced pressure. The fraction having a vapor temperature of 130-135°C was collected at a pressure of 250 Pa to obtain 95.6 g of 2-(4-methyl-benzylidene)heptanal as a light yellow transparent liquid. The GC content was 94.7%.

[0070] (2) Reduction of 2-(4-methyl-benzylidene)heptanal to 2-(4-methyl-benzylidene)heptanol

[0071] A 49.2 g aqueous solution containing 0.1 g of sodium hydroxide and 9.0 g of sodium borohydride was prepared. 165.0 g of 2-(4-methyl-benzylidene)heptanal and 150.0 g of ethanol were added to a 1000 mL reaction vessel, and the mixture was cooled to 10°C. The above-mentioned aqueous solution of sodium borohydride was then added dropwise over 1.5 hours. Subsequently, the mixture was washed twice with 250 mL of 5% brine each time. Finally, the organic layer obtained by liquid separation was distilled under reduced pressure. The fraction having a vapor temperature of 140-145°C was collected at a pressure of 250 Pa to obtain 144.6 g of 2-(4-methyl-benzylidene)heptanol. The GC content was 94.1%.

[0072] (3) Esterification of 2-(4-methyl-benzylidene)heptanol with 5-decenoic acid to produce a decenoic acid ester compound

[0073] A three-necked flask was sequentially charged with 92.5 g of 5-decenoic acid, 110.0 g of 2-(4-methyl-benzylidene)heptanol, 1.3 g of p-toluenesulfonic acid and 200 mL of cyclohexane. The mixture was heated to 86°C and subjected to dehydration reaction under reflux for 7.5 hours. After the reaction was completed, the mixture was washed twice with 250 mL of 5% brine each time. Finally, the organic layer obtained by liquid separation was recovered from cyclohexane and distilled under reduced pressure. The fraction having a vapor temperature of 190-196°C was collected at a pressure of 200 Pa to obtain 158.6 g of 5-decenoic acid 2-(4-methyl-benzylidene)heptanol ester as a light yellow transparent liquid. The GC content was 93.4%.

[0074] The example 2-3 is subjected to NMR, mass spectrometry analysis, and the same nuclear magnetic data, mass spectrometry data, etc. as the 5-decenoic acid 2-(4-methyl-benzylidene) heptyl alcohol ester prepared in the example 1 are obtained, indicating that the example 2-3 can prepare the 5-decenoic acid 2-(4-methyl-benzylidene) heptyl alcohol ester.

[0075] Example 4

[0076] In this example, the decenoic acid ester compound prepared in the example 1 is applied to the shampoo essence, and the specific amount is as follows:

[0077] No. Raw material name Amount (%) 1 Citral 0.6 2 Geranyl acetate 0.6 3 Hexyl butyrate 0.6 4 Iso-methyl ionone 0.7 5 Ivory 0.7 6 Pyrone 0.75 7 Terpineol 0.8 8 Terpinyl acetate 0.85 9 Vanillin 1 10 2-(4-methyl-benzylidene) heptanol ester of 5-decenoic acid 5 11 Styrax acetate 1.2 12 Ambroxan 1.5 13 Brazilian orange oil 1.5 14 Peach aldehyde 1.5 15 Benzyl acetate 1.5 16 Hexyl acetate 2.3 17 Ethyl tricyclohexane 2.8 18 Dihydro myrcenol 3 19 Linalool 3.5 20 O-t-butyl cyclohexyl acetate 4 21 HCA 7 22 Guerlain liquid 8 23 Lilial 10 24 Clean base 10 25 Dipropylene glycol 30.6 Total 100

[0078] Example 5

[0079] In this example, the decenoic acid ester compound prepared in the example 1 is applied to the shower gel essence, and the specific amount is as follows:

[0080] No. Raw material name Amount (%) 1 Myroxin 0.2 2 Benzene ethyl dimethyl acetal 0.2 3 Citral 0.3 4 Guerlain liquid 0.5 5 Indole 0.5 6 2-(4-methyl-benzylidene) heptanol ester of 5-decenoic acid 10 7 Tricyclohexyl propionate 2 8 Geraniol 980 3 9 Linalool 3.5 10 Lily flower base 5 11 Benzyl acetate 6 12 Lilial 7.5 13 Phenylethyl alcohol 12.5 14 HCA 13.5 15 Vanillin 14.5 16 Dipropylene glycol 20.8 Total 100

[0081] Example 6

[0082] In this example, the decenoic acid ester compound prepared in the example 1 is applied to the perfume essence, and the specific amount is as follows:

[0083]

[0084]

[0085] Test

[0086] (I) aroma evaluation:

[0087] Ten perfumers with more than 5 years of work experience are selected to evaluate the aroma of the 5-decenoic acid 2-(4-methyl-benzylidene) heptyl alcohol ester prepared in the example 1 as follows:

[0088] Ten perfumers unanimously believe that the compound presents the characteristic aroma of jasmine, nine perfumers believe that the compound also has milk aroma, and two perfumers believe that the compound also has tea aroma.

[0089] Therefore, the 5-decenoic acid 2-(4-methyl-benzylidene) heptyl alcohol ester prepared in the example 1 can present natural jasmine fragrance and also has milk aroma.

[0090] (II) fragrance retention test:

[0091] Take 1 piece of smelling paper, dip 0.1 g of 5-decenoic acid 2-(4-methyl-benzylidene) heptyl ester prepared in Example 1, place the smelling paper on a smelling rack, and have 5 perfumers smell it every 2 hours, when more than or equal to 2 perfumers cannot perceive the smell of the smelling paper, record the remaining fragrance time.

[0092] The remaining fragrance test shows that the remaining fragrance time of 5-decenoic acid 2-(4-methyl-benzylidene) heptyl ester jasmine is 96 hours, and the remaining fragrance time of milk fragrance is 102 hours.

[0093] Thus it is shown that 5-decenoic acid 2-(4-methyl-benzylidene) heptyl ester prepared in Example 1 can maintain a longer remaining fragrance time.

[0094] The above describes the technical solutions provided by the embodiments of the present application in detail, and the principles and implementation manners of the embodiments of the present application are described by applying specific examples; the above description of the embodiments is only applicable to helping understand the principles of the embodiments of the present application; meanwhile, for those skilled in the art, the specific implementation manners and application ranges of the embodiments of the present application will be changed, and the above description of the present application should not be understood as a limitation of the present application.

Claims

1. A decenoate compound, characterized by: has the following structural formula:

2. A method for producing a decenoate compound, characterized by: comprising the following steps: (1) Preparation of 2-(4-methyl-benzylidene) heptanal: In the reaction kettle, add inorganic alkaline reagent, ethanol solution, after the inorganic alkaline reagent is dissolved in the ethanol solution, add p-methyl benzaldehyde and antioxidant, water bath for 30-40℃, uniform speed drop heptanal, after the drop is completed, continue to stir for 15-25min, drop acetic acid to adjust the pH of the system to 7, heat and reduce pressure to recover ethanol and p-methyl benzaldehyde, after recovery, cool to 35-45℃, after cooling, wash with saturated brine, then adjust the pH of the system to 8 with saturated brine and sodium carbonate solution, finally distill the organic layer obtained, get a light yellow transparent liquid, which is 2-(4-methyl-benzylidene) heptanal; (2) Preparation of 2-(4-methyl-benzylidene) heptyl alcohol: The alkaline aqueous solution containing reducing agent is prepared, and 2-(4-methyl-benzylidene) heptanal and ethanol solution are added in the reaction kettle. The prepared alkaline aqueous solution containing reducing agent is added dropwise, and the obtained organic layer is washed with 3-6% salt water multiple times, and then distilled to obtain 2-(4-methyl-benzylidene) heptyl alcohol; (3) Preparation of 5-decenoic acid 2-(4-methyl-benzylidene) heptyl alcohol ester: In the reaction kettle, 5-decenoic acid, 2-(4-methyl-benzylidene) heptyl alcohol, catalyst and organic solution are added in sequence, heated to 85-90℃, refluxed for 7-9h, after reaction, washed with 3-6% salt water multiple times, recovered the organic solution in the organic layer, and then distilled to obtain a light yellow transparent liquid, which is 5-decenoic acid 2-(4-methyl-benzylidene) heptyl alcohol ester.

3. The method for preparing a decenoic acid ester compound according to claim 2, characterized in that: The molar ratio of p-methyl benzaldehyde to n-heptanal in step (1) is 1.2-1.8:

1.

4. The method for preparing a decenoic acid ester compound according to claim 2, characterized in that: The time for dropping n-heptanal in step (1) is 5.5-6.5h.

5. The method for preparing a decenoic acid ester compound according to claim 2, characterized in that: The distillation in step (1) is reduced pressure distillation, and when reduced pressure distillation is performed, the fraction with a vapor temperature of 130-135℃ is collected under a pressure of 250Pa.

6. The method for preparing a decenoic acid ester compound according to claim 2, characterized in that: After adding 2-(4-methyl-benzylidene) heptanal and ethanol solution in step (2), it needs to be cooled to 8-12℃; the time for dropping the alkaline aqueous solution containing reducing agent is 1.5-2h.

7. The method for preparing a decenoic acid ester compound according to claim 2, characterized in that: The distillation in step (2) is reduced pressure distillation, and when reduced pressure distillation is performed, the fraction with a vapor temperature of 140-145℃ is collected under a pressure of 250Pa.

8. The method for preparing a decenoic acid ester compound according to claim 2, characterized in that: The molar ratio of 5-decenoic acid to 2-(4-methyl-benzylidene) heptyl alcohol in step (3) is 1-1.2:

1.

9. The method for preparing a decenoic acid ester compound according to claim 2, characterized in that: The distillation in step (3) is reduced pressure distillation, and when reduced pressure distillation is performed, the fraction with a vapor temperature of 190-196℃ is collected under a pressure of 200Pa.

10. Use of a decenoate compound, characterized by: The decenoate compound of claim 1 or the decenoate compound prepared by the preparation method of any one of claims 2-9 is applied as a fragrance in daily chemical perfuming.

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