CN112759585A - Compound with tomato aroma, preparation method thereof and daily essence - Google Patents
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Abstract
The invention relates to the field of spices, and particularly relates to a compound with tomato fragrance, a preparation method thereof and a daily essence. The invention discloses a compound with tomato aroma, which has a structure shown in a formula (I). Researches show that the compound with tomato aroma has remarkable tomato aroma characteristics, high aroma intensity, long aroma retention time and stable aroma. The invention also provides a preparation method of the compound with tomato aroma, and the preparation method has the advantages of simple and convenient process flow, easily obtained preparation raw materials and suitability for batch production. The invention further provides a daily essence containing the compound with tomato aroma.
Description
Technical Field
The invention relates to the field of spices, and particularly relates to a compound with tomato fragrance, a preparation method thereof and a daily essence.
Background
The perfume can endow the daily product with special fragrance, so that the daily product has pleasant fragrance characteristics on the basis of practicability.
The tomato aroma characteristics have obvious identification degree. Fresh tomatoes have a green aroma, are sour and sweet, and carry a little greasy smell, while ripe tomatoes have a more pronounced sour and sweet berry-like aroma. However, no compound has been found to have the aroma characteristics of cooked tomatoes when used alone. Therefore, the preparation of the compound with tomato aroma is of great significance through a chemical synthesis method.
Disclosure of Invention
Based on the above, the invention provides a compound with tomato aroma, and researches show that the compound has remarkable tomato aroma, strong aroma retention capacity and stable and lasting aroma.
In order to achieve the above purpose of the present invention, the following technical solutions are adopted:
in one aspect of the present invention, a compound having tomato aroma is provided, which has a structure represented by formula (I):
in one aspect of the present invention, there is also provided a method for preparing a compound having tomato aroma, comprising the steps of:
(1) mixing furfuryl alcohol and dimethyl carbonate with an organic solvent, and reacting under the conditions of a catalyst and heating to prepare the ditrfuryl carbonate, wherein the structural formula of the furfuryl alcohol is shown in the specification
The structural formula of the dimethyl carbonate is
The structural formula of the carbonic acid bifurfuryl ester is shown in the specification
(2) Mixing ditrfuryl carbonate and ethylMixing maltol with organic solvent, and reacting under the presence of catalyst and heating to obtain compound with tomato fragrance, wherein ethyl maltol has a structural formula
In a specific embodiment, the heating temperature in the step (1) is 55-70 ℃, and the heating time is 20-30 h; and/or
The heating temperature in the step (2) is 55-70 ℃, and the heating time is 8-12 h.
In a specific embodiment, the molar ratio of furfuryl alcohol to dimethyl carbonate is 1:1 to 2: 1.
In a specific embodiment, the molar ratio of the ditrfuryl carbonate to the ethyl maltol is 1:1 to 2: 1.
In a specific embodiment, the catalyst in step (1) and the catalyst in step (2) are each independently selected from at least one of concentrated sulfuric acid having a concentration of 98 (v/v)% and p-toluenesulfonic acid, aluminum trichloride, and 4-dimethylaminopyridine.
In a specific embodiment, the organic solvent in step (1) and the organic solvent in step (2) are each independently selected from at least one of chloroform, cyclohexane, toluene, and dichloromethane.
In a specific embodiment, after the step (1) and before the step (2), the method further comprises the step of concentrating the solution after the reaction in the step (1) to prepare the purified bifurfuryl carbonate.
In a specific embodiment, after the step (2), the method further comprises the steps of concentrating the solution obtained after the reaction in the step (2), dissolving and filtering the concentrated solute, and preparing the purified compound with the specific tomato aroma.
In another aspect of the present invention, there is further provided a perfume composition comprising the compound having tomato aroma described above.
The compound having tomato aroma prepared above can be named as 2-ethyl-4-oxo-4H-pyran-3-yl (furan-2-ylmethyl) carbonate. The gas chromatographic analysis shows that the main fragrant substances of the tomatoes are cis-3-hexenal, cis-3-hexenol, linalool, beta-ionone, beta-damascone, 3-methylbutyric acid, 3-methylbutanol and the like, but the substances do not have the characteristic fragrance emitted by the tomatoes when being used alone. Therefore, the compound with tomato aroma prepared by the invention has the advantages of obvious tomato aroma characteristic when being used alone, high aroma intensity, stable and lasting aroma and wide application in the preparation process of essence and daily products.
The compound with tomato aroma prepared by the invention has the advantages of wide and easily available raw materials, simple and convenient process flow and suitability for wide popularization and application.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings used in the description of the embodiments or the prior art will be briefly described below, and it is obvious that the drawings in the following description are some embodiments of the present invention, and other drawings can be obtained by those skilled in the art without creative efforts.
FIG. 1 is a nuclear magnetic resonance hydrogen spectrum of a compound having tomato aroma prepared in one embodiment of the present invention;
FIG. 2 is a nuclear magnetic resonance carbon spectrum of a compound having tomato aroma prepared in one example of the present invention;
fig. 3 is a gas chromatogram of compounds with tomato aroma prepared in one example of the invention.
Detailed Description
Reference will now be made in detail to embodiments of the invention, one or more examples of which are described below. Each example is provided by way of explanation, not limitation, of the invention. In fact, it will be apparent to those skilled in the art that various modifications and variations can be made in the present invention without departing from the scope or spirit of the invention. For instance, features illustrated or described as part of one embodiment, can be used on another embodiment to yield a still further embodiment.
It is therefore intended that the present invention cover the modifications and variations of this invention provided they come within the scope of the appended claims and their equivalents. Other objects, features and aspects of the present invention are disclosed in or are apparent from the following detailed description. It is to be understood by one of ordinary skill in the art that the present discussion is a description of exemplary embodiments only, and is not intended as limiting the broader aspects of the present invention.
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. As used herein, the term "and/or" includes any and all combinations of one or more of the associated listed items.
Other than as shown in the operating examples, or where otherwise indicated, all numbers expressing quantities of ingredients, physical and chemical properties, and so forth used in the specification and claims are to be understood as being modified in all instances by the term "about". Accordingly, unless indicated to the contrary, the numerical parameters set forth in the specification and attached claims are approximations that can be calculated by one skilled in the art using the teachings disclosed herein to achieve the desired properties, and such approximations are suitable. The use of numerical ranges by endpoints includes all numbers within that range and any range within that range, for example, 1 to 5 includes 1, 1.3, 1.5, 1.7, 2, 2.85, 3, 4, 4.50, and 5, and the like.
In one aspect of the present invention, a compound having tomato aroma is provided, which has a structure represented by formula (I):
according to the invention, through research, the main fragrant substances of the tomatoes are cis-3-hexenal, cis-3-hexenol, linalool, beta-ionone, beta-damascone, 3-methylbutyric acid, 3-methylbutanol and the like, but the substances do not have the characteristic fragrance emitted by the tomatoes when being used alone. The compound with the structure can have remarkable tomato aroma characteristics by being used alone, and has high aroma intensity and stable and lasting aroma.
In one aspect of the present invention, there is also provided a method for preparing a compound having tomato aroma, comprising the steps of:
(1) mixing furfuryl alcohol and dimethyl carbonate with an organic solvent, and reacting under the conditions of a catalyst and heating to prepare the ditrfuryl carbonate, wherein the structural formula of the furfuryl alcohol is shown in the specification
The structural formula of the dimethyl carbonate is
The structural formula of the carbonic acid bifurfuryl ester is shown in the specification
(2) Mixing ditrfuryl carbonate and ethyl maltol with organic solvent, and reacting under heating in the presence of catalyst to obtain compound with tomato fragrance, wherein the structural formula of ethyl maltol is shown in the specification
The compound with tomato aroma prepared by the invention has the advantages of wide and easily available raw materials, simple and convenient process flow and suitability for wide popularization and application.
In the present invention, the heating temperature in the step (1) is 55 to 70 ℃ and the heating time is 20 to 30 hours. In a preferred embodiment, the heating temperature in step (1) is 62 ℃ and the heating time is 24 h.
In the present invention, the heating temperature in the step (2) is 55 ℃ to 70 ℃ and the heating time is 8 hours to 12 hours. In a preferred embodiment, the heating temperature in step (2) is 62 ℃ and the heating time is 10 h.
In the present invention, the molar ratio of furfuryl alcohol to dimethyl carbonate is 1:1 to 2:1, and may be 1.5:1, 1.7:1, or 1.8:1, for example. In a preferred embodiment, the molar ratio of furfuryl alcohol to dimethyl carbonate is 2: 1.
In the present invention, the molar ratio of the difurfuryl carbonate to the ethyl maltol is 1:1 to 2:1, and may be 1.3:1, 1.5:1, or 1.8:1, for example. In a preferred embodiment, the molar ratio of ditrfuryl carbonate to ethyl maltol is 1.5: 1.
In the present invention, as a further explanation, the catalyst in the step (1) and the catalyst in the step (2) are each independently at least one selected from the group consisting of concentrated sulfuric acid having a concentration of 98 (v/v)%, p-toluenesulfonic acid, aluminum trichloride and 4-dimethylaminopyridine. In a preferred embodiment, the catalyst in step (1) is selected from concentrated sulfuric acid having a concentration of 98 (v/v)% and the catalyst in step (2) is selected from p-toluenesulfonic acid.
In the present invention, as a further explanation, the organic solvent in the step (1) and the organic solvent in the step (2) are each independently at least one selected from chloroform, cyclohexane, toluene, and dichloromethane. In a preferred embodiment, both the organic solvent in step (1) and the organic solvent in step (2) are selected from chloroform.
In the present invention, as a further explanation, the method further comprises a step of preparing a purified bifurfuryl carbonate by concentrating the solution after the reaction in the step (1) after the step (1) and before the step (2).
In the present invention, as a further explanation, the method further comprises the step of concentrating the solution after the reaction in the step (2), dissolving the concentrated solute, and filtering to prepare the purified compound with specific tomato aroma after the concentration.
In the present invention, the pressure for concentration is 100Pa to 400Pa, and the time for concentration is 10min to 60 min. In a preferred embodiment, the pressure of the concentration is 150Pa and the time of concentration is 20 min.
In the present invention, as a further explanation, the solvent used for dissolving the solute is at least one selected from the group consisting of ethanol, 1, 3-propanediol and 4-oxo-2, 6-hexanediol. In a preferred embodiment, the solvent used for solute dissolution is ethanol.
In another aspect of the present invention, there is further provided a daily essence, which comprises the compound with tomato aroma described above.
In the invention, the daily essence can be perfume essence, essence in skin care products or essence in clothes cleaning daily necessities.
The compound having tomato aroma, the preparation method thereof and the daily essence of the present invention will be described in further detail with reference to the following specific examples.
Unless otherwise specified, reagents or materials used in the examples of the present invention are commercially available.
Example 1 preparation of compounds having tomato aroma
The specific process for preparing compounds with tomato aroma in this example is as follows:
the method comprises the following steps: preparation of ditrfuryl carbonate
1962g of furfuryl alcohol, 3L of chloroform and 901g of dimethyl carbonate are sequentially added into a 10L reaction kettle, 10mL of concentrated sulfuric acid is added dropwise, the temperature is raised to 62 ℃, the reaction is carried out for 24h, then the mixture is concentrated for 20min under the conditions that the temperature is 40 ℃ and the pressure is 150Pa, and the solvent is removed, so that 2222g of ditrfuryl carbonate is obtained.
Step two: preparation of 2-ethyl-4-oxo-4H-pyran-3-yl (furan-2-ylmethyl) carbonate
Placing 2222g of the prepared difurfuryl carbonate into a 10L reaction kettle, adding 3L of chloroform, then adding 934g of ethyl maltol, then adding 50g of p-toluenesulfonic acid, heating to 62 ℃, and carrying out heat preservation reaction for 10 hours. Then, the mixture was concentrated at 40 ℃ and 150Pa for 20min to remove the solvent. Then, at 50 ℃, the residual solid after concentration is dissolved by 500mL of ethanol, then 2L of ultrapure water is added, natural cooling is carried out, standing is carried out for 24H, and precipitated solid is collected by filtration, thus obtaining 1533g of 2-ethyl-4-oxo-4H-pyran-3-yl (furan-2-ylmethyl) carbonate.
(1) 2-Ethyl-4-oxo-4H-pyran-3-yl (furan-2-ylmethyl) carbonate has the following NMR spectral characteristics:
hydrogen nuclear magnetic resonance spectroscopy:
1H NMR(400MHz,CD3Cl):7.77-7.65(m,2H),6.50-6.32(m,3H),5.15(s,2H),2.01(q,2H,J＝4.4Hz),1.07(t,3H,J＝4.4Hz)。
nuclear magnetic resonance carbon spectrum:
3C NMR(100MHz,CD3Cl):157.2,155.5,152.1,150.6,149.3,143.6,136.9,110.8,107.7,103.9,62.9,21.0,10.8。
the NMR hydrogen spectrum and NMR carbon spectrum of 2-ethyl-4-oxo-4H-pyran-3-yl (furan-2-ylmethyl) carbonate are shown in figure 1 and figure 2 respectively.
(2) 2-Ethyl-4-oxo-4H-pyran-3-yl (furan-2-ylmethyl) carbonate has the following mass spectral characteristics:
MS(ESI,m/z)287.2(M+Na+) (ii) a The theoretical calculation data of the high-resolution electrospray ionization mass spectrum is [ C ]13H12NaO6]+(M+Na+)287.0526, the actual measured value was 287.0541.
(3) The prepared 2-ethyl-4-oxo-4H-pyran-3-yl (furan-2-ylmethyl) carbonate was subjected to gas chromatography using an Agilent technologies, Inc. model 7820A gas chromatograph, to obtain a gas chromatogram shown in FIG. 3.
From the above experimental data, example 1 successfully prepared the specific tomato aroma compound 2-ethyl-4-oxo-4H-pyran-3-yl (furan-2-ylmethyl) carbonate.
Example 2 preparation of compounds with tomato aroma
The process for preparing compounds having tomato aroma in example 2 is substantially the same as the process for preparing example 1, except that: furfuryl alcohol, dimethyl carbonate, ditrfuryl carbonate and ethyl maltol.
The preparation method of the compound with tomato aroma described in example 2 comprises the following steps:
the method comprises the following steps: preparation of ditrfuryl carbonate
1668g of furfuryl alcohol, 3L of chloroform and 901g of dimethyl carbonate are sequentially added into a 10L reaction kettle, 10mL of concentrated sulfuric acid is dropwise added, the temperature is raised to 62 ℃, the reaction is carried out for 24h, then the mixture is concentrated for 20min under the conditions that the temperature is 40 ℃ and the pressure is 150Pa, and the solvent is removed, thus 1887g of the ditrfuryl carbonate is obtained.
Step two: preparation of 2-ethyl-4-oxo-4H-pyran-3-yl (furan-2-ylmethyl) carbonate
Placing 1887g of the prepared dicarfuryl carbonate into a 10L reaction kettle, adding 3L of chloroform, adding 916g of ethyl maltol, adding 45g of p-toluenesulfonic acid, heating to 62 ℃, keeping the temperature and reacting for 8 hours, concentrating for 20min at the temperature of 40 ℃ and the pressure of 150Pa, and removing the solvent. Then, at 50 ℃, the solid remaining after concentration was dissolved in 300mL of ethanol, and then 1.2L of ultrapure water was added, followed by natural cooling and standing for 24 hours, and the precipitated solid was collected by filtration to obtain 1405g of 2-ethyl-4-oxo-4H-pyran-3-yl (furan-2-ylmethyl) carbonate.
Experiments prove that the compound with tomato aroma prepared in example 2 is the same as the compound with tomato aroma prepared in example 1, and is not described again.
Example 3 preparation of Compounds with tomato aroma
The process for preparing compounds having tomato aroma in example 3 is substantially the same as the process for preparing example 1, except that: furfuryl alcohol, dimethyl carbonate, ditrfuryl carbonate and ethyl maltol.
The preparation method of the compound with tomato aroma described in example 3 comprises the following steps:
the method comprises the following steps: preparation of ditrfuryl carbonate
1786g of furfuryl alcohol, 3L of chloroform and 901g of dimethyl carbonate are sequentially added into a 10L reaction kettle, 10mL of concentrated sulfuric acid is dropwise added, the temperature is raised to 62 ℃, the reaction is carried out for 24h, then the mixture is concentrated for 20min under the conditions that the temperature is 40 ℃ and the pressure is 150Pa, and the solvent is removed, thus obtaining 1999g of the ditrfuryl carbonate.
Step two: preparation of 2-ethyl-4-oxo-4H-pyran-3-yl (furan-2-ylmethyl) carbonate
1999g of the prepared carbonic acid ditrfuryl ester is put into a 10L reaction kettle, 3L of chloroform is added, 701g of ethyl maltol is added, 40g of p-toluenesulfonic acid is added, and the temperature is raised to 62 ℃ for heat preservation reaction for 8 hours. Then, the mixture was concentrated at 40 ℃ and 150Pa for 20min to remove the solvent. Then, at 50 ℃, dissolving the residual solid after concentration by 300mL of ethanol, then adding 1.2L of ultrapure water, naturally cooling, standing for 24H, filtering and collecting the precipitated solid to obtain 1287g of 2-ethyl-4-oxo-4H-pyran-3-yl (furan-2-ylmethyl) carbonate.
Experiments prove that the compound with tomato aroma prepared in example 3 is the same as the compound with tomato aroma prepared in example 1, and is not described again.
And (3) fragrance testing:
the aroma intensity of 2-ethyl-4-oxo-4H-pyran-3-yl (furan-2-ylmethyl) carbonate and ethyl maltol acetate obtained in example 1 was evaluated by a 10-position odorator under a well ventilated and no noticeable odor atmosphere by scoring for 1 to 10 points, and the evaluation results are shown in Table 1, taking the average of the scores.
The specific method for testing the fragrance retention time is as follows: 2 strips of fragrance-smelling test paper were dipped in 0.1g of 2-ethyl-4-oxo-4H-pyran-3-yl (furan-2-ylmethyl) carbonate and 0.1g of ethyl maltol acetate, respectively, which were prepared in example 1. The test paper is placed on a fragrance smelling frame, 10 fragrance flavourists smell the test paper once every 1 hour in an environment with good ventilation and no obvious smell, when the fragrance flavourists cannot sense the fragrance of the fragrance smelling test paper, the fragrance remaining time is recorded, the average value of the fragrance remaining time recorded by the 10 fragrance flavourists is taken, and the measured fragrance remaining time is shown in table 1.
TABLE 1 aroma Properties of 2-Ethyl-4-oxo-4H-pyran-3-yl (furan-2-ylmethyl) carbonate in example 1
The fragrance test result shows that the compound with tomato fragrance prepared by the invention has obvious fragrance characteristics, high fragrance intensity and long fragrance retention time.
The aroma characteristics of the compounds with tomato aroma prepared in examples 2 and 3 are similar to those of the compounds with tomato aroma prepared in example 1.
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 several embodiments 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. A compound having tomato aroma, having the structure of formula (I):
2. the method for preparing compounds with tomato aroma according to claim 1, characterized by comprising the following steps:
(1) mixing furfuryl alcohol and dimethyl carbonate with an organic solvent, and reacting under the conditions of a catalyst and heating to prepare the ditrfuryl carbonate, wherein the structural formula of the furfuryl alcohol is shown in the specification
The structural formula of the dimethyl carbonate is shown as
The structural formula of the carbonic acid ditrfuryl ester is shown as
(2) Mixing the ditrfuryl carbonate and ethyl maltol with an organic solvent, and reacting under the conditions of a catalyst and heating to prepare a compound with tomato fragrance, wherein the structural formula of the ethyl maltol is shown in the specification
3. The method for preparing compounds with tomato aroma according to claim 2, wherein the heating temperature in step (1) is 55-70 ℃, and the heating time is 20-30 h; and/or
The heating temperature in the step (2) is 55-70 ℃, and the heating time is 8-12 h.
4. The method for preparing a compound having tomato aroma according to claim 2, wherein the molar ratio of the furfuryl alcohol to the dimethyl carbonate is 1:1 to 2: 1.
5. The method for preparing a compound having tomato aroma according to claim 2, wherein the molar ratio of the difurfuryl carbonate to the ethyl maltol is 1:1 to 2: 1.
6. The method for preparing a compound having tomato aroma according to any one of claims 2 to 5, wherein the catalyst in step (1) and the catalyst in step (2) are each independently selected from at least one of concentrated sulfuric acid having a concentration of 98 (v/v)%, p-toluenesulfonic acid, aluminum trichloride, and 4-dimethylaminopyridine.
7. The method for preparing a compound having tomato aroma according to any one of claims 2 to 5, wherein the organic solvent in step (1) and the organic solvent in step (2) are each independently selected from at least one of chloroform, cyclohexane, toluene, and dichloromethane.
8. The method for preparing a compound having tomato aroma according to claim 2, further comprising the step of concentrating the solution after the reaction of step (1) to prepare purified bifurfuryl carbonate, after the step (1) and before the step (2).
9. The method for preparing a compound having tomato aroma according to any one of claims 2 to 5 and 8, further comprising the steps of concentrating the solution after the reaction in step (2), dissolving the concentrated solute, and filtering to prepare a purified compound having specific tomato aroma.
10. A daily essence comprising the compound having tomato aroma of claim 1.
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|---|---|---|---|---|
| CN115819379A (en) * | 2021-09-16 | 2023-03-21 | 中国科学院大连化学物理研究所 | Preparation method of dimethylfurfuryl carbonate |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102827108A (en) * | 2012-07-24 | 2012-12-19 | 北京金骄生物质化工有限公司 | Bio-based functional material as well as preparation method and application thereof |
| CN108299359A (en) * | 2018-03-20 | 2018-07-20 | 东南大学 | A kind of furans esters of gallic acid tobacco aromaticss and preparation method thereof and the application in cigarette |
-
2021
- 2021-01-04 CN CN202110003052.4A patent/CN112759585B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102827108A (en) * | 2012-07-24 | 2012-12-19 | 北京金骄生物质化工有限公司 | Bio-based functional material as well as preparation method and application thereof |
| CN108299359A (en) * | 2018-03-20 | 2018-07-20 | 东南大学 | A kind of furans esters of gallic acid tobacco aromaticss and preparation method thereof and the application in cigarette |
Non-Patent Citations (3)
| Title |
|---|
| JIAN-XING XU ET AL.: "Palladium-Catalyzed Decarboxylative Carbonylative Transformation of Benzyl Aryl Carbonates:Direct Synthesis of Aryl 2-Arylacetates", 《ORG. LETT.》 * |
| 张华: "几个新型香料在香精中的应用", 《香料香精化妆品》 * |
| 马洪亮 等: "檀香类香料的合成及发展", 《香料香精化妆品》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115819379A (en) * | 2021-09-16 | 2023-03-21 | 中国科学院大连化学物理研究所 | Preparation method of dimethylfurfuryl carbonate |
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Address after: No. 8, Xixi Road, Liaobu Town, Dongguan City, Guangdong Province, 523000 Patentee after: Botton Spices Co.,Ltd. Address before: 523411 No.8 Dadiao Road, liangbian village, Liaobu Town, Dongguan City, Guangdong Province Patentee before: DONGGUAN BOTON FLAVORS & FRAGRANCES Co.,Ltd. |
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