CN111170969B - Compound with caramel cream flavor, preparation method thereof and edible essence - Google Patents
Compound with caramel cream flavor, preparation method thereof and edible essence Download PDFInfo
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- CN111170969B CN111170969B CN202010061846.1A CN202010061846A CN111170969B CN 111170969 B CN111170969 B CN 111170969B CN 202010061846 A CN202010061846 A CN 202010061846A CN 111170969 B CN111170969 B CN 111170969B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/205—Heterocyclic compounds
- A23L27/2052—Heterocyclic compounds having oxygen or sulfur as the only hetero atoms
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/206—Dairy flavours
Abstract
The invention relates to a compound with a caramel cream flavor, a preparation method thereof and edible essence. The compound having a caramel cream flavor has the following structural formula:
the aromatic furfuryl ester compound has the fragrance different from that of the traditional aliphatic furfuryl ester compound, has the burnt butter fragrance of special caramel and milk fragrance, has the fragrance intensity slightly higher than that of furfuryl thioacetate, has the fragrance complexity close to furfurylthiol, and can be used for perfuming food.
Description
Technical Field
The invention relates to the field of chemical synthesis, in particular to a compound with a caramel cream flavor, a preparation method thereof and an edible essence.
Background
In sesame oil composition testing, sesame is found to contain many furfuryl thio compounds, and most of them have coffee or sesame-like aroma characteristics. Among them, furfuryl mercaptan is commonly called caffeoaldehyde and is mainly used for endowing food with coffee-like top aroma and body aroma, and fatty acid esterification products of furfuryl mercaptan have softer aroma and are often used for coffee-like body aroma, such as furfuryl thioacetate and furfuryl thiopropionate which are widely applied to food flavoring. However, the aroma characteristics of the traditional esterification products of the furfurylthiol are coffee flavor and the aroma is single.
Disclosure of Invention
Based on this, there is a need for a bran ester compound having a caramel and milk-like caramel cream flavor.
In addition, a preparation method of the compound with the flavor of the caramel cream and the edible essence are also provided.
A compound having a caramel cream flavor, having the formula:
a method for preparing a compound having a caramel cream flavor, comprising the steps of:
reacting furfuryl mercaptan with phenylacetyl chloride to obtain a compound with a caramel cream flavor, wherein the compound with the caramel cream flavor has the following structural formula:
in one embodiment, in the step of reacting furfuryl mercaptan with phenylacetyl chloride, the reaction temperature is 0-30 ℃ and the reaction time is 2-5 hours.
In one embodiment, the off-gas produced in the step of reacting furfuryl mercaptan with phenylacetyl chloride is absorbed with a basic solution.
In one embodiment, the step of reacting furfuryl mercaptan with phenylacetyl chloride further comprises: distilling the reacted reagent, and collecting the fraction at 135-149 deg.c under 200-300 Pa to obtain purified furfuryl thiophenylacetate.
In one embodiment, the method further comprises the step of reacting phenylacetic acid with thionyl chloride to obtain phenylacetyl chloride.
In one embodiment, in the step of reacting phenylacetic acid with thionyl chloride, the reaction temperature is 70-78 ℃, and the reaction time is 1-2 h.
In one embodiment, after the step of reacting phenylacetic acid with thionyl chloride, the method further comprises the following steps: and distilling the reacted solution to remove excessive thionyl chloride to obtain purified phenylacetyl chloride.
In one embodiment, the gas generated in the step of reacting phenylacetic acid with thionyl chloride is absorbed with an alkaline solution.
An edible essence comprising the above compound having a caramel cream smell or a compound having a caramel cream smell obtained by the preparation method of the above compound having a caramel cream smell.
Compared with furfuryl mercaptan, furfuryl thioacetate, furfuryl thiopropionate and the like, the characteristic aroma of the furfuryl ester compound is remarkably changed. The aromatic furfuryl ester compound has the fragrance different from that of the traditional aliphatic furfuryl ester compound, has the burnt butter fragrance of special caramel and milk fragrance, has the fragrance intensity slightly higher than that of furfuryl thioacetate, has the fragrance complexity close to furfurylthiol, and can be used for perfuming food.
Drawings
FIG. 1 is a process flow diagram of a method of preparing a compound having a caramel cream flavor according to one embodiment;
FIG. 2 is a gas chromatogram of the compound having a caramel cream flavor prepared in example 1.
Detailed Description
In order that the invention may be more fully understood, reference will now be made to the following description taken in conjunction with the accompanying drawings. The detailed description sets forth the preferred embodiments of the invention. This invention may, however, be embodied in many different forms and should not be construed as limited to the embodiments set forth herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete.
Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. The terminology used in the description of the invention herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention.
An embodiment of a compound having a caramel cream flavor has the following structural formula:
the compound with the burnt butter flavor is named as furfuryl thioacetate, and the molecular formula is as follows: c13H12O2S, molecular weight is 232.
The traditional furfuryl ester compounds and furfuryl mercaptan have coffee-like flavor body fragrance, such as furfuryl thioacetate, furfuryl thiopropionate and the like, and compared with the furfuryl mercaptan, the furfuryl thioacetate, the furfuryl thiopropionate and the like, the characteristic fragrance of the furfuryl ester compounds is obviously changed. The aromatic furfuryl ester compound has the fragrance different from that of the traditional aliphatic furfuryl ester compound, has the burnt butter fragrance of special caramel and milk fragrance, has the fragrance intensity slightly higher than that of furfuryl thioacetate, has the fragrance complexity close to furfurylthiol, and can be used for perfuming food.
Referring to fig. 1, a method for preparing a compound having a caramel cream flavor according to an embodiment is a method for preparing a compound having a caramel cream flavor according to the above embodiment, including the steps of:
step S110: reacting phenylacetic acid with thionyl chloride to obtain phenylacetyl chloride.
Wherein, the structural formula of phenylacetyl chloride is as follows:
specifically, the molar ratio of the phenylacetic acid to the thionyl chloride is 1: 1.05-1: 1.5. In one embodiment, in the step of reacting phenylacetic acid with thionyl chloride, the phenylacetic acid is added to the reaction vessel first, and then thionyl chloride is slowly added. The phenylacetic acid and the thionyl chloride react relatively quickly, so the thionyl chloride is slowly dripped in the reaction process, the reaction is prevented from being too fast, and a large amount of generated tail gas is difficult to completely absorb.
The reaction of step S110 is carried out under heating. Specifically, the reaction temperature is 70 ℃ to 78 ℃. The reaction time is 1-2 h.
The gas generated in step S110 is absorbed with an alkaline solution. In one embodiment, the alkaline solution is an aqueous sodium hydroxide solution. Further, the mass concentration of the aqueous sodium hydroxide solution was 10%. It is understood that in other embodiments, the alkaline solution may be a common alkaline solution such as an aqueous solution of potassium hydroxide, an aqueous solution of sodium carbonate, or the like. The concentration of the alkaline aqueous solution is not limited to 10% by mass, and may be other concentrations.
Specifically, the method also comprises a purification step after the step of reacting phenylacetic acid with thionyl chloride. In one embodiment, the step of purifying comprises: and distilling the reacted solution to remove excessive thionyl chloride to obtain purified phenylacetyl chloride.
In one embodiment, step S110 is: adding phenylacetic acid into a reaction container, then dropwise adding thionyl chloride, and after the dropwise adding of the thionyl chloride is finished, heating to 70-78 ℃ to continue reacting for 1-2 h. And tail gas generated in the reaction process is absorbed by a sodium hydroxide aqueous solution with the mass concentration of 10%. After the reaction is finished, reduced pressure distillation is carried out to obtain purified phenylacetyl chloride.
In one embodiment, phenylacetic acid and thionyl chloride are reacted to provide phenylacetyl chloride according to the following reaction scheme:
the preparation step of phenylacetyl chloride is not limited to step S110, and may be any other method commonly used in the art. Alternatively, phenylacetyl chloride may be purchased directly, in which case step S110 may be omitted.
Step S120: reacting furfuryl mercaptan with phenylacetyl chloride to obtain a compound having a caramel cream taste.
Wherein the structural formulas of the furfuryl mercaptan and the compound with the caramel cream flavor are respectively as follows:
furfuryl mercaptan:
compound with a caramel cream flavour:
wherein the molar ratio of the furfuryl mercaptan to the phenylacetyl chloride is 1: 1-1: 1.5. In one embodiment, in the step of reacting furfuryl mercaptan with phenylacetyl chloride, furfuryl mercaptan is added to the reaction vessel and phenylacetyl chloride is added dropwise. Because the reaction between furfuryl mercaptan and phenylacetyl chloride is fast, the phenylacetyl chloride is slowly dripped in the reaction process, the reaction is prevented from being too fast, and a large amount of tail gas generated is difficult to completely absorb.
Specifically, step S120 is performed at room temperature. In one embodiment, the temperature of the reaction is from 0 ℃ to 30 ℃. The reaction time is 2-5 h. Further, the reaction temperature was 25 ℃ and the reaction time was 3 hours.
And absorbing tail gas generated in the reaction process of the step S120 by using an alkaline solution. Specifically, the alkaline solution may be an aqueous sodium hydroxide solution. In one embodiment, the aqueous sodium hydroxide solution has a mass concentration of 10%. It is understood that in other embodiments, the alkaline solution may be a common alkaline solution such as an aqueous solution of potassium hydroxide, an aqueous solution of sodium carbonate, or the like. The concentration of the alkaline aqueous solution is not limited to 10% by mass, and may be other concentrations.
The step of reacting furfuryl mercaptan with phenylacetyl chloride is followed by a purification step. Specifically, the purification step comprises: distilling the reacted reagent, and collecting the fraction at 135-149 deg.c under 200-300 Pa to obtain purified furfuryl thiophenylacetate.
In one embodiment, step S120 is: adding furfuryl mercaptan into the reaction solution, then dropwise adding phenylacetyl chloride at 0-30 ℃, reacting for 2-5 h after dropwise adding, and absorbing tail gas generated in the reaction process by using a sodium hydroxide aqueous solution with the mass concentration of 10%. After the reaction is finished, carrying out reduced pressure distillation, and collecting the fraction with the temperature of 135-149 ℃ under the pressure of 200-300 Pa to obtain the furfuryl sulfophenylacetate.
Specifically, in step S120, the synthetic route of the reaction is as follows:
the compound with the burnt butter flavor is named as furfuryl thioacetate, and the molecular formula is as follows: c13H12O2S, molecular weight is 232.
The preparation method of the compound with the caramel cream flavor at least has the following advantages:
(1) the preparation method of the compound can prepare the caramel cream-flavor compound with caramel and milk flavor, and the characteristic aroma of the furfuryl ester compound is obviously changed relative to furfuryl mercaptan, furfuryl thioacetate, furfuryl thiopropionate and the like. The aromatic furfuryl ester compound has the fragrance different from that of the traditional aliphatic furfuryl ester compound, has the burnt butter fragrance of special caramel and milk fragrance, has the fragrance intensity slightly higher than that of furfuryl thioacetate, has the fragrance complexity close to furfurylthiol, and can be used for perfuming food.
(2) The preparation method of the compound with the caramel cream flavor has simple process and high yield, and can be used for industrial production.
An essence for food according to an embodiment is characterized by comprising the compound having a caramel cream flavor according to the above embodiment or a compound having a caramel cream flavor obtained by the method for producing the compound having a caramel cream flavor. The compound with the caramel cream flavor has special caramel and milk flavors, the fragrance intensity is slightly higher than that of furfuryl thioacetate, the fragrance complexity is close to that of furfurylthiol, and therefore, the compound can be used in edible essence.
The following are specific examples:
example 1
The preparation process of the compound with a caramel cream flavor of the embodiment is specifically as follows:
(1) preparation of phenylacetyl chloride:
adding phenylacetic acid (2.5L) into a 10L reaction kettle, slowly adding thionyl chloride (1.5L), heating to 78 ℃ after dropwise adding, reacting, absorbing tail gas generated in the reaction process by a sodium hydroxide aqueous solution with the mass concentration of 10%, stirring for 1 hour, and distilling under reduced pressure to obtain phenylacetyl chloride (3.0 kg).
(2) Preparation of furfuryl thiophenylacetate:
adding furfuryl mercaptan (2.0L, commercially available from Hongxin Riyu Fine chemical Co., Ltd., Hubei) into a 10L reaction kettle, slowly dropwise adding phenylacetyl chloride (3.0kg) at 25 ℃, reacting for 3 hours after dropwise adding, and absorbing tail gas generated in the reaction process by using a sodium hydroxide aqueous solution with the mass concentration of 10%. After the reaction is finished, carrying out reduced pressure distillation, and collecting the fraction with the temperature of 135-142 ℃ under the pressure of 200Pa to obtain the furfuryl thiophenylacetate (4.2 kg).
The furfuryl thiophenylacetate prepared in this example has the following NMR spectral characteristics:
1H NMR(400MHz，CD3Cl)：7.58(d，1H，J＝7.2Hz)，7.35-7.21(m，5H)，6.44-6.37(m，1H)，6.10(d，1H，J＝7.6Hz)，3.99(s，2H)，3.65(s，2H)。
13C NMR(100MHz，CD3Cl)：202.9，151.4，142.0，138.7，129.6，127.5，110.7，106.8，33.4，32.4。
the data of the mass spectrometry analysis of furfuryl thiophenylacetate prepared in this example are as follows:
MS(ESI，m/z)：255.0(M+Na+) (ii) a The theoretical calculation data of the high-resolution electrospray ionization mass spectrum is [ C ]13H12NaO2S]+(M+Na+): 255.0450, the actual measured value was 255.0476.
The gas chromatography analysis of the compound having a caramel cream taste prepared in example 1 was performed using a gas chromatography apparatus of agilent 7820A, and the gas chromatogram shown in fig. 2 was obtained.
As can be seen from the above experimental data, furfuryl thiophenylacetate, a compound having a caramel cream flavor, was successfully prepared in example 1.
Example 2
The preparation process of the compound with a caramel cream flavor of the embodiment is specifically as follows:
(1) preparation of phenylacetyl chloride:
adding phenylacetic acid (2.5L) into a 10L reaction kettle, slowly adding thionyl chloride (1.5L), heating to 70 ℃ after dropwise adding, reacting, absorbing tail gas generated in the reaction process by a sodium hydroxide aqueous solution with the mass concentration of 10%, stirring for 2 hours, and distilling under reduced pressure to obtain phenylacetyl chloride (3.0 kg).
(2) Preparation of furfuryl thiophenylacetate:
adding furfuryl mercaptan (2.0L, commercially available from Hongxin Riyu Fine chemical Co., Ltd., Hubei) into a 10L reaction kettle, slowly dropwise adding phenylacetyl chloride (3.0kg) at 30 ℃, reacting for 2 hours after dropwise adding, and absorbing tail gas generated in the reaction process by using a sodium hydroxide aqueous solution with the mass concentration of 10%. After the reaction, the reaction mixture was distilled under reduced pressure, and the fraction having a temperature of 142 to 149 ℃ was collected under 300Pa to obtain furfuryl thiophenylacetate (4.2 kg).
Example 3
The preparation process of the compound with a caramel cream flavor of the embodiment is specifically as follows:
(1) preparation of phenylacetyl chloride:
adding phenylacetic acid (2.5L) into a 10L reaction kettle, slowly adding thionyl chloride (1.5L), heating to 75 ℃ after dropwise adding, reacting, absorbing tail gas generated in the reaction process by a sodium hydroxide aqueous solution with the mass concentration of 10%, stirring for 1.5 hours, and distilling under reduced pressure to obtain phenylacetyl chloride (3.0 kg).
(2) Preparation of furfuryl thiophenylacetate:
adding furfuryl mercaptan (2.0L, commercially available from Hongxin Riyu Fine chemical Co., Ltd., Hubei) into a 10L reaction kettle, slowly dropwise adding phenylacetyl chloride (3.0kg) at 0 ℃, reacting for 5 hours after dropwise adding, and absorbing tail gas generated in the reaction process by using a sodium hydroxide aqueous solution with the mass concentration of 10%. After the reaction is finished, carrying out reduced pressure distillation, and collecting the fraction with the temperature of 140-146 ℃ under the pressure of 250Pa to obtain the furfuryl thiophenylacetate (4.2 kg).
Experiments have shown that the compounds prepared in examples 2 and 3 are identical to the compound prepared in example 1 and are not described in further detail herein.
Comparative example 1
The preparation of the compound of comparative example 1 is specifically as follows:
(1) preparation of benzoyl chloride:
benzoic acid (115g) was added to a 500mL reactor followed by thionyl chloride (73.3mL), the temperature was raised to 78 deg.C and the reaction was stirred for 1 h. And tail gas generated in the reaction process is absorbed by a sodium hydroxide aqueous solution with the mass concentration of 10%. After completion of the reaction, distillation was carried out under reduced pressure to give benzoyl chloride (123 g).
(2) Preparation of furfuryl thiobenzoate:
adding furfuryl mercaptan (94g) into a 500mL reaction kettle, slowly dropwise adding benzoyl chloride (120g) at 25 ℃, reacting for 3 hours after dropwise adding, and absorbing tail gas generated in the reaction process by using a sodium hydroxide aqueous solution with the mass concentration of 10%. After the reaction, the mixture was distilled under reduced pressure, and the fraction having a temperature of 137 to 144 ℃ was collected under a pressure of 250Pa to obtain furfuryl thiobenzoate (153 g).
The following are test sections:
1. the aroma characteristics were compared by comparing commercially available furfuryl mercaptan, furfuryl thioacetate with furfuryl thiophenylacetate prepared. Since high concentrations of furfuryl thiol, furfuryl thioacetate, and furfuryl thiophenylacetate all had unpleasant malodorous odors, 1000-fold dilutions were required using dipropylene glycol as a solvent, followed by evaluation of the flavor properties of the above compounds after 1000-fold dilution using (i)0 to 10 odor intensity (where 0 is none, 1 is very weak, 5 is moderate, 10 is very strong) and (ii) complexity level (where 0 is none, 1 is very low, 5 is moderate, 10 is very high). The average scores of fragrance evaluations by 10 perfumers who worked over 5 years are reported in table 1 below.
TABLE 1
As can be seen from table 1 above, the furfuryl thiophenylacetate prepared in example 1 has a significant change in characteristic aroma compared to furfurylthiol and furfuryl thioacetate. Researchers in the field know that subtle changes in the structure of a compound may cause an unexpected change in the aroma of the compound. The above-mentioned furfuryl thiophenylacetate has a complex aroma profile, mainly described as caramel and milk-flavored caramel cream-like aroma, with slightly higher intensity and complexity close to that of furfuryl mercaptan.
2. The aroma characteristics of the compound prepared in comparative example 1 were evaluated using the above test methods, and the data shown in table 2 below were obtained.
Table 2 aroma characteristics of the compounds prepared in comparative example 1
| Compound (I) | Odor characteristics | Strength of | Complexity of |
| Furfuryl thiobenzoate | Burnt smell, rubber-like pungent smell | 8.1 | 7.2 |
As can be seen from table 2 above, furfuryl thiobenzoate is highly irritating, presents an unpleasant rubber-like irritating odor, is accompanied by a burnt odor, has no characteristic milk-like aroma, and cannot be used as a perfume. The furfuryl thiophenylacetate obtained in example 1 has obvious milk fragrance characteristics and no rubber smell, and compared with the smell of furfuryl thiobenzoate, the fragrance of the furfuryl thiophenylacetate is obviously changed, and the unexpected fragrance change enables the furfuryl thiophenylacetate to endow unique fragrance characteristics to products in baking and coffee flavoring processes.
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 a caramel cream flavor, having the formula:
2. a method for preparing a compound having a caramel cream flavor, comprising the steps of:
reacting furfuryl mercaptan with phenylacetyl chloride to obtain a compound with a caramel cream flavor, wherein the compound with the caramel cream flavor has the following structural formula:
3. the method for preparing a compound having a caramel cream flavor as claimed in claim 2, wherein in the step of reacting furfuryl mercaptan with phenylacetyl chloride, the reaction temperature is 0 to 30 ℃ and the reaction time is 2 to 5 hours.
4. The method for producing a compound having a caramel cream flavor as claimed in claim 2, wherein the off-gas generated in the step of reacting furfuryl mercaptan with phenylacetyl chloride is absorbed with an alkaline solution.
5. The method for preparing a compound having a caramel cream flavor as claimed in claim 2, wherein the step of reacting furfuryl mercaptan with phenylacetyl chloride is followed by: distilling the reacted reagent, and collecting the fraction at 135-149 deg.c under 200-300 Pa to obtain purified furfuryl thiophenylacetate.
6. The method of claim 2, further comprising the step of reacting phenylacetic acid with thionyl chloride to obtain said phenylacetyl chloride.
7. The method for producing a compound having a caramel cream flavor according to claim 6, wherein the step of reacting phenylacetic acid with thionyl chloride is carried out at a reaction temperature of 70 to 78 ℃ for a reaction time of 1 to 2 hours.
8. The method of claim 6, wherein the step of reacting phenylacetic acid with thionyl chloride is followed by purifying: and distilling the reacted solution to remove excessive thionyl chloride to obtain purified phenylacetyl chloride.
9. The method for producing a compound having a caramel cream flavor as claimed in claim 6, wherein the gas generated in the step of reacting phenylacetic acid with thionyl chloride is absorbed by an alkaline solution.
10. An essence for food, comprising the compound having a caramel cream flavor produced by the method for producing a compound having a caramel cream flavor according to any one of claims 2 to 9.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101506187A (en) * | 2006-08-04 | 2009-08-12 | 弗门尼舍有限公司 | New furyl thioalkanals useful in the flavor industry |
| CN101885714A (en) * | 2010-07-17 | 2010-11-17 | 天津市化学试剂研究所 | Edible flavor difurfuryl thioether |
| CN107033027A (en) * | 2016-11-17 | 2017-08-11 | 东莞波顿香料有限公司 | A kind of aromatic aldehyde schiff bases and its preparation method and application |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101506187A (en) * | 2006-08-04 | 2009-08-12 | 弗门尼舍有限公司 | New furyl thioalkanals useful in the flavor industry |
| CN101885714A (en) * | 2010-07-17 | 2010-11-17 | 天津市化学试剂研究所 | Edible flavor difurfuryl thioether |
| CN107033027A (en) * | 2016-11-17 | 2017-08-11 | 东莞波顿香料有限公司 | A kind of aromatic aldehyde schiff bases and its preparation method and application |
Non-Patent Citations (1)
| Title |
|---|
| 两种焦糖色的特征风味成分和4-甲基咪唑分析;林琪 等;《中国测试》;20180731;第44卷(第7期);第51-55页 * |
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|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant | ||
| CP03 | Change of name, title or address | ||
| CP03 | Change of name, title or address |
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. |