JP6678015B2 - New smoke imparting agent and method for producing the same - Google Patents

Description

  The present invention relates to a novel smoke-imparting agent which can be prepared safely and easily without using components derived from smoked products or chemically synthesized compounds, and which can impart a good smoke feeling, and a method for producing the same.

  Smoke treatment is a process in which wood is burned or smoked in a smoke chamber to generate smoke and attach it to foods such as meat, meat products, eggs, and the like. It is known for providing antiseptic properties. The unique flavor is called smoke flavor and is a major feature of smoked products. Originally, the purpose of the smoke treatment was to improve the preservability, but in the modern age with improved preservation technology, the main purpose is to give smoke flavors, that is, to give a smoke feeling in search of the uniqueness of smoke products. It has become.

  Smoke that produces smoke flavor contains more than 200 types of volatile components and solid components. Among the components that contribute to smoke flavor, aldehydes, ketones, and phenols are known. Among them, an important component is a guaiacol compound.

  Conventionally known methods for producing guaiacol compounds include methods that use organic solvents / reagents that cannot be used as foods and drinks, and methods that require high-temperature, high-pressure treatment that involves danger in work. Almost. For example, Patent Document 1 discloses a method for producing 5-nitroguaiacol by electrolytic hydroxylation of p-nitroanisole.

  Patent Literature 2 discloses a method for producing a 4-vinylguaiacol polymer compound having anticancer activity by heating ferulic acid under alkaline conditions such as an aqueous solution of sodium bicarbonate. Although this production method can be said to be a safe and simple method, the produced guaiacol polymer has poor volatility and cannot be used for the purpose of imparting a smoke feeling.

  In recent years, methods for producing guaiacol compounds using microorganisms and enzymes have also been reported. For example, Patent Document 3 discloses a method for producing vanillin and guaiacol useful as a flavor by a fermentation method using a specific microorganism. Patent Literature 4 discloses that an undiluted liquor having a high content of 4-vinylguaiacol can be produced by adding a ferulic acid esterase enzyme during the production of a distilled spirit. However, these methods are not efficient as a method for producing a guaiacol compound for use as a smoke-imparting agent.

  On the other hand, a method for enhancing the smoke feeling of foods and drinks has also been reported. Patent Document 5 discloses that at least one selected from a smoked product and an extract fraction extracted from the smoked product contains a sulfur-containing amino acid and a sulfur-containing amino acid. A method for adding a sulfur-containing compound such as a peptide or a sulfur-containing vitamin is described. Patent Literature 6 describes a method for improving the smoke feeling by adding sucralose to a smoked product. These are methods for enhancing the smoke sensation derived from the scented product, and do not newly generate the smoke sensation itself.

  As described above, smoke can be safely and easily prepared using only substances and methods that are safe for the human body without actually performing smoke treatment or using components derived from smoked smoke products. Sensitizers have not been previously known.

JP-A-59-21584 JP 2012-111736 A JP-A-11-069990 JP 2014-57536 A JP 2005-46109 A JP-A-2000-166462

  An object of the present invention is to provide a smoke-imparting agent that is highly safe, easy to manufacture, and highly versatile for foods and drinks, and a method for manufacturing the same.

  The present inventors have intensively studied a method capable of imparting a high-quality smoke feeling without using a smoked product actually smoked as a raw material and using only a safe substance and a method for the human body. It has been found that a reaction product obtained by heating ferulic acid in the presence of an amine compound is a component capable of imparting a good smoke sensation, and furthermore, it is possible to prepare a component imparting a smoke sensation under relatively low temperature heating conditions. As a result, the present inventors have found that it is possible to prepare a component that imparts a safe and high-quality smoke feeling while avoiding generation of harmful components due to high heat treatment, and completed the present invention.

  That is, the present invention provides a highly safe, easy-to-manufacture, and highly versatile smoked product for foods and drinks, comprising a reactant obtained by heating ferulic acid in the presence of an amine compound as an active ingredient. Providing an imparting agent.

  Until now, when trying to impart smoke to foods and drinks in a safe way, it was necessary to actually use smoke extract or use an extract obtained from smoke-treated foods, etc. Even without performing such a complicated smoke treatment, it was found that by using a reactant obtained by a simple treatment of heating ferulic acid in the presence of an amine compound, a high-quality smoke feeling was obtained, The present invention has been made. The ferulic acid heating reactant which is a component for imparting a smoke feeling of the present invention is a heat reactant generated at a relatively low heating temperature such as 80 to 200 ° C. The present invention provides a smoke-imparting agent for foods and drinks that is safe and has a good smoke-like effect without using components such as smoke treatment using high heat, and thus generating no harmful substances due to high heat treatment. be able to.

  The reaction product obtained by heating the ferulic acid of the present invention in the presence of an amine compound includes 4-vinylguaiacol, 4-ethylguaiacol, 4-propylguaiacol, and guaiacol. Wherein at least one guaiacol compound is contained.

  In the present invention, as the amine compound used for preparing a reaction product obtained by heating ferulic acid in the presence of the amine compound, which is a smoke-imparting component of the smoke imparting agent, a free primary amino Examples include any one or more compounds selected from among amino acids, peptides, and proteins having a group, and ammonium salts. The heating temperature when reacting ferulic acid in the presence of an amine compound can be in the range of 80 to 200 ° C.

  The present invention comprises a step of heating ferulic acid at a temperature of 80 to 200 ° C. in the presence of an amine compound, a method for producing a guaiacol-type compound-containing reactant used for imparting smoke to a food or drink, or ferulic acid. A method for imparting smoke to food or drink, characterized by adding a guaiacol-containing compound-containing reaction product obtained by heating in the presence of an amine compound to the food or drink.

  The present invention relates to [1] a smoke-imparting agent for foods and drinks containing, as an active ingredient, a reactant obtained by heating ferulic acid in the presence of an amine compound, and [2] the presence of an amine compound in ferulic acid. The reaction product obtained by heating under the above is, in the reaction product, one or more kinds selected from 4-vinylguaiacol, 4-ethylguaiacol, 4-propylguaiacol, and guaiacol. An amino acid or peptide comprising a guaiacol compound, wherein the smoke-imparting agent for food or drink according to the above [1] or [3] an amine compound has a free primary amino group. And a protein, and at least one compound selected from ammonium salts, wherein the agent for imparting a smoked feeling to food or drink according to the above [1] or [2], [4] The food or drink according to any of [1] to [3] above, wherein the reaction product obtained by heating is a reaction product obtained by heating within a heating temperature range of 80 to 200 ° C. A smoke-imparting agent for the product.

  Further, the present invention comprises a step of [5] heating ferulic acid at a temperature of 80 to 200 ° C. in the presence of an amine compound, and containing a guaiacol compound used for imparting smoke to food or drink. A method for producing a reactant, and [6] adding a guaiacol compound-containing reactant obtained by heating ferulic acid in the presence of an amine compound to the food or drink, wherein , And a method of applying.

  The present invention provides a highly versatile smoke-imparting agent that is highly safe, easy to manufacture, and can impart a good smoke feeling to food and drink, and a method for producing the same.

  The present invention comprises a smoke-imparting agent for a food or drink, comprising a reaction product obtained by heating ferulic acid in the presence of an amine compound as an active ingredient, and a method for producing the same. Here, the smoke feeling refers to a unique flavor, also called smoke odor, which is felt when a smoked product is ingested.

  In the present invention, as the ferulic acid used for preparing a reaction product obtained by heating ferulic acid, which is a smoke-imparting component, in the presence of an amine compound, commercially available ferulic acid (which is approved as a food additive) High-purity one) can be used. In addition, fruits containing ferulic acid (ferulic acid-containing substances) such as sugar beet, corn, wheat, rice, and their brans, potatoes, carrots, vegetable peels such as tomatoes, various berries, grapes, apples and other fruit peels; Bark or the like may be used as it is. Since ferulic acid is mainly present as a glycoside in these natural products, in order to release ferulic acid, these natural products are subjected to a chemical treatment such as acid decomposition, enzymatic decomposition, alkali extraction, or an extraction treatment. It is preferable to use it as a chemically treated product or extract obtained by subjecting the same to a further purification treatment, and it is more preferable to use the chemically treated product or extract as a crudely purified product or purified product of ferulic acid.

  In the present invention, as the amine compound used for preparing a reaction product obtained by heating ferulic acid, which is a smoke-imparting component, in the presence of an amine compound, primary, secondary, and tertiary amino groups Any compound may be used as long as it is a compound having trimethylamines, dimethylamines, animal and plant proteins, peptides, amino acids, and metal salts thereof, ammonium carbonate, ammonium acetate, ammonium lactate, and organic acids such as ammonium phosphate. Any of ammonium salts and the like can be mentioned. The amine compounds may be used alone or in combination of two or more. Further, as amine compounds, for example, whey protein, milk protein such as casein, egg white protein, egg protein such as egg yolk protein, plasma protein, blood protein such as blood cell protein, meat protein, protein such as muscle protein such as fish meat protein, Peptides obtained by subjecting these proteins to chemical treatment, enzymatic treatment, physical treatment, or the like, or fungi such as animals and plants, lactic acid bacteria, and yeast rich in proteins and peptides may be used.

  Among these amine compounds, in particular, having a free primary amino group, amino acids, peptides, or proteins, and any one or more compounds selected from ammonium salts of inorganic acids or organic acids, This is preferable because the efficiency of producing a smoke-imparting component from ferulic acid is improved. For this reason, when using an amino acid, a peptide, or a protein, the raw material used is subjected to a decomposition treatment such as a well-known acid hydrolysis method or an enzymatic decomposition method to generate a free primary amino group. It is preferably used, and in this case, the amino acid release rate is preferably 10 w / w% or more, and more preferably 40 w / w% or more.

  In the present invention, the method itself of preparing a reaction product by heat-treating ferulic acid in the presence of an amine compound is not particularly limited. For example, a method in which an amine compound is added to heated ferulic acid or a ferulic acid-containing substance, and further heated if necessary, ferulic acid or a ferulic acid-containing substance is added to the heated amine compound to be heated And a method in which ferulic acid or a ferulic acid-containing substance and an amine compound are mixed in advance to form a mixture and then heated.

  In the present invention, when a reaction product is prepared by heat-treating ferulic acid in the presence of an amine compound, the quantitative ratio of ferulic acid to the amine compound is determined by the guaiacol compound in the resultant obtained after the heat treatment. Is not particularly limited as long as it is an amount ratio of at least 2 ppm or more, and varies depending on the heating reaction conditions, but as a weight ratio of ferulic acid to the amine compound, it is usually 1:50 to 50: 1, preferably 1:25 to 25: 1, more preferably 1:10 to 10: 1.

  In the present invention, when heat treatment of ferulic acid in the presence of an amine compound, the heat treatment may be performed in a powder state, or in water, ethanol, alcohol such as glycerol, or a liquid such as animal and vegetable oils and fats. The heat treatment may be performed in any state of fats and oils, but the pH at the time of heat treatment in a liquid medium is preferably pH 7.0 or less in order to suppress generation of components unnecessary for imparting a smoke feeling.

  The temperature for the heat treatment is preferably at least 80 ° C. in order to efficiently generate the components involved in imparting the smoke sensation obtained by the heat treatment, and 200 ° C. in order to suppress the generation of components unnecessary for imparting the smoke sensation. It is preferable that the temperature is not higher than ° C. Furthermore, more preferably, it is 90-170 degreeC, Most preferably, it is 100-130 degreeC.

  The time for the heat treatment may be appropriately adjusted depending on the balance with the heating temperature.However, in order to suppress the efficient generation of components involved in imparting the smoke sensation and the generation of components unnecessary for imparting the smoke sensation, for example, 80 ° C. For about 5 to 10 hours, for heat treatment at 120 ° C. for about 30 minutes to 2 hours, preferably for about 30 to 1 hour, and for about 200 ° C. for about 5 to 15 minutes.

  In the present invention, a reaction product obtained by heat-treating ferulic acid in the presence of an amine compound includes a group consisting of 4-vinylguaiacol, 4-ethylguaiacol, 4-propylguaiacol and guaiacol. And at least one guaiacol compound selected from the group consisting of guaiacol compounds, and particularly preferably 4-vinyl guaiacol.

  In the present invention, a reaction product obtained by heat-treating ferulic acid in the presence of an amine compound is prepared as a smoke-imparting agent for food or drink, which contains a smoke-imparting component. The content of the guaiacol compound in the smoke-imparting agent is usually adjusted to 2 ppm or more, more preferably 5 ppm or more, further preferably 10 ppm or more.

  The smoke imparting agent of the present invention includes, as necessary, various food and drink additives, protein acid hydrolysates, enzymatic degradation products, yeast extracts, animal and plant fish and shellfish extracts, flavors and the like, together with seasoning materials for food and drink. May be used. Further, the smoke-imparting agent of the present invention may be in any form of solid or liquid.

  The method of using the smoke imparting agent of the present invention is the same as a normal food or drink additive or seasoning, except that it is added to the food or drink to be used. The timing may be any time, such as during the production of food or drink, after the production of food or drink, or at the time of eating.

  Foods and drinks to be used for the smoke-imparting agent of the present invention may be any foods and drinks as long as they have a smoked flavor, for example, livestock meat, fish meat, hams, Processed meat products such as sausages (including livestock meat and fish meat), dairy products such as cheese, eggs, processed egg products, and the like are included. The amount of the smoke-imparting agent of the present invention to be added to food or drink depends on the type of food or drink, the required degree of smoke, and the like, and may be appropriately set.

  Hereinafter, examples of the present invention will be described, but the present invention is not limited to these examples.

<Reaction product preparation example 1>
Pig-derived gelatin was heat-treated in the presence of hydrochloric acid and spray-dried to obtain an acid-decomposed powder of gelatin (hereinafter referred to as powder 1). The free amino acid ratio (the ratio of the amount of free amino acids to the total amount of amino acids; the same applies hereinafter) in the acid-decomposed powder of the gelatin was measured by an amino acid analyzer (manufactured by Hitachi, Ltd.) and found to be 98 w / w%. The defatted soybean protein was treated with protease and spray-dried to obtain a soybean protein enzymatically decomposed powder (free amino acid ratio: 54 w / w%; hereinafter, referred to as powder 2). Further, the same operation was performed except that dry brewer's yeast was used instead of the defatted soybean protein, to obtain an enzyme-decomposed yeast extract powder (free amino acid ratio: 42 w / w%; hereinafter, referred to as powder 3).

  1 g of ferulic acid (powder) and 5 g of DL-alanine (powder) were powder-mixed, and heated at 120 ° C. for 45 minutes to obtain a reaction product of Example 1. The same except that powder 1, powder 2, powder 3, powder defatted soybean protein (raw material of powder 2, free amino acid ratio: 1 w / w%) and ammonium acetate (powder) were used instead of DL-alanine. Of Example 2 (powder 1), Example 3 (powder 2), Example 4 (powder 3), Example 5 (powder defatted soybean protein) and Example 6 (ammonium acetate) Were obtained. The same heating reaction was carried out using only ferulic acid to obtain a heat-treated ferulic acid (Comparative Example 1).

  The obtained reactants of Examples 1 to 6 and the heat-treated product of Comparative Example 1 were subjected to solid phase extraction by the SPME method and analyzed using a gas chromatograph mass spectrometer (manufactured by Shimadzu Corporation). From the results of the retention time and mass spectrometry, it was found that each reaction product contained 4-vinylguaiacol, 4-ethylguaiacol, 4-propylguaiacol and guaiacol. Furthermore, each component was quantified using a standard sample of these guaiacol compounds. Table 1 shows the results of quantification of the sum of these.

<Evaluation Example 1 of Reactant>
Using soy sauce, broth, aged hon mirin and salt, Control 1 of Mentsuyu was prepared according to a conventional method. Control 2 was obtained by adding a commercially available smoke liquid (manufactured by Red Arrow Co.) to Control 1 at a concentration of 0.01 v / v%. The reactants of Examples 1 to 6 and the heat-treated product of Comparative Example 1 were added to Control 1 so as to be 0.005 v / v%, respectively, to prepare respective evaluation test plots. The salt content concentration in each evaluation test group was adjusted to be approximately the same.

Sensory evaluation was performed on the quality and strength of the smoke sensation in each of the obtained evaluation test sections. The sensory evaluation was performed by a panel of four skilled workers. The sensory evaluation (smoke feeling) was performed according to the following evaluation methods and evaluation criteria. Using Control 1 as a criterion (0), the similarity to Control 2 was evaluated by a three-point scale method.
0 point: no change 1 point: slightly similar 2 points: similar 3 points: very similar

  Table 2 shows the results. The evaluation in the table is the average of the scores of the four panelists. In addition, “*” or “**” at the right shoulder of the numerical values in the table indicates that there is a significant difference from Control 1 at P <0.05 and P <0.01, respectively.

  As shown in Table 2, the reactants of Examples 1 to 6, which were obtained by heating and reacting ferulic acid with amines, were added. In particular, the addition of the reaction product of Example 3 using an enzyme-decomposed product of soybean protein and the reaction product of Example 4 using an enzyme-degraded yeast extract was effective in improving the smoke quality and strength. Was also highly effective.

<Reaction product preparation example 2>
Ferulic acid (powder, the same applies hereinafter) (1 g) and 5 g of powder 2 (prepared in Preparation Example 1; the same applies hereinafter) were powder-mixed and heated at 70 ° C. for 5 hours to obtain a reaction product of Comparative Example 2. I got Further, 1 g of ferulic acid and 100 g of powder 2 were powder-mixed and heated at 120 ° C. for 45 minutes to obtain a reaction product of Example 7. Further, 10 g of ferulic acid and 100 mg of powder 2 were powder-mixed and heated at 120 ° C. for 45 minutes to obtain a reaction product of Example 8. Furthermore, 1 g of ferulic acid and 5 g of powder 2 were powder mixed and heated at 200 ° C. for 10 minutes to obtain a reaction product of Example 9.

<Evaluation example 2 of reactant>
Using the noodle soup prepared in Evaluation Example 1 (Control 1), the reactants of Comparative Example 2, Example 3 and Examples 7 to 9 were added to give 0.005 w / v%, respectively, and each evaluation test group was added. Was prepared. The salt content concentration in each evaluation test plot was adjusted to be about the same.

Sensory evaluation was performed on the quality and strength of the smoke sensation in each evaluation test section. The sensory evaluation was performed by a panel of four skilled workers. The sensory evaluation (smoke feeling) was performed according to the following evaluation methods and evaluation criteria. Using Control 1 as a criterion (0), the similarity to Control 2 was evaluated by a three-point scale method.
0 point: no change 1 point: slightly similar 2 points: similar 3 points: very similar

The results are shown in Table 2. The evaluation in the table is the average of the scores of the four panelists.
In addition, “*” or “**” at the right shoulder of the numerical values in the table indicates P <0.05 and P <0.01, respectively, for the test group to which the reactant of Example 3 was added. Indicates that there is a significant difference.

  As shown in Table 3, the effect of imparting a smoke feeling to the reaction product obtained by heating ferulic acid in the presence of the amine compound was confirmed in each of the test plots of Example 3 and Examples 7 to 9. However, in the reaction product of Example 3, the strongest smoke-imparting effect was confirmed.

    The present invention provides a highly versatile smoke-imparting agent that is highly safe, easy to manufacture, and can impart a good smoke feeling to food and drink, and a method for producing the same.

Claims (2)

  Ferulic acid purified product or ferulic acid partially purified product has a free primary amino group, an amino acid, a peptide, and a protein, and an amine compound which is one or more compounds selected from ammonium salts. A method for producing a guaiacol-type compound-containing reactant used for imparting smoke to food or drink, comprising a step of heating at a temperature of 80 to 200 ° C. in the presence. Ferulic acid purified product or ferulic acid partially purified product has a free primary amino group, an amino acid, a peptide, and a protein, and an amine compound which is one or more compounds selected from ammonium salts. A guaiacol-containing compound-containing reactant is produced by a production method including a step of heating at a temperature of 80 to 200 ° C in the presence, and the guaiacol-containing compound-containing reactant obtained by the production method is added to food or drink. A method for imparting smoke to foods and drinks, characterized by the following.