JP4905529B2 - Acrylamide production suppression method and its application - Google Patents

Description

  The present invention relates to a method for inhibiting the production of acrylamide known as a carcinogenic substance or a substance causing neuropathy and its use, and an edible substance containing an organic substance having an amino group and / or a sugar having an acrylamide-producing ability. A method for suppressing the generation of acrylamide generated by heat-treating the material to a relatively high temperature. Specifically, when heat-treating an edible material that may generate acrylamide by heat treatment, the edible material is suppressed from generating acrylamide. The present invention relates to a method for suppressing the production of acrylamide, characterized by containing an organic substance having a function, and heat-treating it, and its use.

  Recently, according to Non-Patent Document 1, a considerable amount of acrylamide, known as a carcinogenic substance, is present in processed foods that we frequently eat on a daily basis, such as potato chips, french fries, bread, and fried bread. Contained and concerns about health effects.

  On the other hand, regarding the mechanism of acrylamide production, in Non-Patent Document 2, an amino acid such as L-asparagine and a reducing sugar such as D-glucose contained in a food material are heated to a high temperature exceeding 100 ° C. to cause Maillard reaction. A mechanism has been proposed for waking up and producing acrylamide.

  Thus, although it has been found that acrylamide is produced in the heat processing step of edible materials, there is no known method for reducing the amount of production or further actively suppressing the production of acrylamide. Establishment of a method is desired. This can be seen from the fact that Non-Patent Document 3 has announced that “study on acrylamide production inhibition and toxicity inhibition will be carried out immediately”.

Eden Taleke et al., "Journal of Agricultural and Food Chemistry", 50, 4998-5006 (2002). Donald S. Mottram et al., Nature, 419, 448-450 (2002). Ministry of Health, Labor and Welfare website, "About acrylamide in processed foods", Ministry of Health, Labor and Welfare, Food Health Department, Topics dated October 31, 2002, http: // www. mhlw. go. jp. / Houdou / 2002/10 / h1031-2. html

  The present invention establishes a method for actively suppressing the amount of acrylamide produced by heat-treating edible materials at a high temperature, and is a safer composition for foods, cosmetics, pharmaceuticals, or intermediate products thereof. It is an issue to provide.

  The inventors of the present invention focused on the mechanism of acrylamide formation and conducted extensive research on the effects of coexistence of various sugars with organic substances having amino groups at high temperatures. Includes a saccharide and / or phenolic substance having acrylamide production inhibitory ability, and more specifically, α, α-trehalose, α, β-trehalose, reduced palatinose, α-glucosyl α, α-trehalose, α-maltosyl one or more carbohydrates selected from α, α-trehalose, D-mannitol, D-erythritol, and β-cyclodextrin, and / or catechins such as catechin, epicatechin, epigallocatechin, quercetin, Flavonoids such as isoquercitrin, rutin, naringin, hesperidin, kaempferol, cinnamic acid, quinic acid, 3 , 4-dihydrocinnamic acid, 3-coumaric acid, 4-coumaric acid, p-nitrophenol, curcumin, scopoletin, propyl p-hydroxybenzoate and proanthocyanidins or their carbohydrate derivatives Compared with the case where the specific organic substance does not coexist by heat-treating the above phenolic substance in the presence of an organic substance having an amino group and a saccharide that can react with this and produce acrylamide. Thus, the inventors have found a completely new fact that production of acrylamide can be remarkably suppressed, and based on this fact, the present invention has been completed.

  That is, the present invention is characterized in that when an edible material that may generate acrylamide by heat treatment is heat-treated, the edible material is heat-treated by containing an organic substance having an ability to suppress acrylamide formation. A method for suppressing the production of acrylamide, specifically, an edible material that contains an organic substance having an amino group and a saccharide capable of reacting with this and capable of producing acrylamide to produce acrylamide by heat treatment. In the treatment, the edible material contains an organic substance having an ability to inhibit acrylamide formation and heat-treated, and an acrylamide production inhibition method is established, and the production of acrylamide produced using this method is established. Compositions such as suppressed foods, drinks, cosmetics, pharmaceuticals, or intermediate products thereof, acrylamide Acrylamide production inhibitors containing organic substances with inhibitory ability as active ingredients, foods and drinks, cosmetics, pharmaceuticals, or intermediate products with acrylamide production inhibitory ability containing organic substances with acrylamide production inhibitory ability, etc. The above-mentioned problems are solved by providing the composition.

  According to the method for inhibiting the production of acrylamide of the present invention, when an edible material that may generate acrylamide by heat treatment is subjected to heat treatment, the organic substance having an amino group that is included in and / or included in the edible material; In this way, the production of acrylamide from saccharides capable of producing acrylamide can be remarkably suppressed. In addition, by applying the method for inhibiting acrylamide production of the present invention to the production of various compositions such as foods, cosmetics, pharmaceuticals, or intermediate products thereof, there is little risk of causing carcinogenesis and neuropathy. A composition can be produced.

  The edible material that may generate acrylamide by heat treatment as used in the present invention refers to an organic substance having an amino group and / or a saccharide that reacts with this and has an ability to form acrylamide, and / or a saccharide that includes and / or contains the same. It means all edible materials that can produce acrylamide by heat treatment.

  Examples of the organic substance having an amino group in the present invention include glycine, L-alanine, L-valine, L-leucine, L-isoleucine, L-serine, L-threonine, L-aspartic acid, L-glutamic acid, An amino acid selected from L-asparagine, L-glutamine, L-lysine, L-arginine, L-cysteine, L-methionine, L-phenylalanine, L-tryptophan, and L-proline, or an amino acid thereof as a constituent amino acid Examples thereof include peptides and proteins.

  As an edible material containing an organic substance having an amino group, the organic substance having an amino group, or one or more of the organic substances having the amino group, for example, agricultural products, livestock products, marine products, processed products thereof, etc. More specifically, for example, in addition to the amino acid-based and / or nucleic acid-based seasoning containing the organic substance having the amino group, soy sauce, miso, sauce, grilled meat sauce, ketchup, mayonnaise, Examples include seasonings such as butter, cheese, vinegar, mirin, sake, wine, carrero, stew, dashi, oyster extract, bonito extract, kelp extract, shiitake extract, yeast extract and meat extract.

  The saccharide having acrylamide-forming ability in the present invention means all saccharides that may react with an organic substance having an amino group to produce acrylamide, and examples thereof include D-xylose and L-arabinose. One or more monosaccharides selected from D-glucose, D-fructose and D-galactose, one selected from D-xylose, L-arabinose, D-glucose, D-fructose and D-galactose Reducing oligosaccharides containing two or more saccharides as constituent sugars, non-reducing oligosaccharides such as sucrose, raffinose and stachyose containing D-fructose as constituent sugars, which are easily decomposed by heat and acid, and L- Examples include L-ascorbic acids such as ascorbic acid, L-ascorbic acid derivatives, or salts thereof. Examples of L-ascorbic acid derivatives include L-ascorbic acid 2-glucoside, L-ascorbic acid 5-glucoside, L-ascorbic acid 6-glucoside, L-ascorbic acid 2-phosphate, L-ascorbic acid 6-fatty acid ester, etc. Is mentioned. Examples of the salt of L-ascorbic acid or an L-ascorbic acid derivative include alkali metal salts such as sodium salt of L-ascorbic acid or L-ascorbic acid derivative, or alkaline earth metal salts such as magnesium salt.

  Examples of edible materials containing saccharides having acrylamide-forming ability include the aforementioned saccharides, or one or more of them, such as agricultural products, livestock products, marine products or processed products thereof. More specifically, for example, sugar sweeteners such as glucose, fructose, isomerized sugar, starch syrup, reduced starch syrup, lactose, sugar and the like containing the above-mentioned sugars can be mentioned.

  The edible material containing an organic substance having an amino group and / or a saccharide capable of producing acrylamide by reacting with the organic substance will be specifically described with examples of foods and drinks. In addition to the ingredients, for example, sliced potatoes, boiled potatoes, steamed potatoes, mashed potatoes, potatoes to be reconstituted, potato flour, germinated wheat, cracked wheat, flour, wheat germ, dough, gluten, germinated barley, germinated rice, Rice grits, rice flour, corn grits, corn flour, buckwheat flour, soy flour, defatted soybeans, soybean casein, boiled beans, paste beans, germinated soybeans, etc., and further, these materials can be blended in one or more kinds. Agricultural products and processed products including premix products and intermediate products such as sponge mix, donut mix, tempura powder, tempura seed set, salad mix etc. For example, refrigerated or frozen meat, carcass, milk, skim milk, fresh cream, milk casein, butter, cheese, whey, whole egg, liquid egg, egg yolk, egg white, boiled egg, or the like Processed products, and further, for example, marine products such as chilled or frozen fish, fillets, surimi, dried fish, salted fish, shelled shellfish, or processed products thereof.

  The organic substance having the ability to suppress acrylamide generation in the present invention means that acrylamide is allowed to coexist when heat-treating an edible material containing the organic substance having an amino group and the saccharide having the acrylamide generating ability. It means all organic substances that have the action of suppressing the production of Examples of organic substances having acrylamide production inhibitory ability include saccharides having acrylamide production inhibitory ability and / or phenolic substances, and saccharides having acrylamide production inhibitory ability include, for example, α, α-trehalose, α , Β-trehalose, reduced palatinose, α-glucosyl α, α-trehalose, α-maltosyl α, α-trehalose, D-mannitol, D-erythritol, and β-cyclodextrin, and acrylamide. Examples of phenolic substances having the ability to suppress production include catechins such as catechin, epicatechin, and epigallocatechin, flavonoids such as quercetin, isoquercitrin, rutin, naringin, hesperidin, kaempferol, cinnamic acid, quina Acid, 3,4-dihydrocinnamic acid, 3 -Phenolic substances such as coumaric acid, 4-coumaric acid, p-nitrophenol, curcumin, scopoletin, propyl p-hydroxybenzoate and proanthocyanidins or their carbohydrate derivatives, and one kind selected from these organic substances Alternatively, two or more kinds can be advantageously used in the present invention. In particular, carbohydrates such as α, α-trehalose and / or α, β-trehalose, and phenolic substances such as rutin, naringin and / or hesperidin are sugars having organic groups having amino groups and acrylamide-forming ability. In the edible material containing the quality, generation of acrylamide by heat treatment is remarkably suppressed.

  Commercially available saccharides can also be advantageously used as the saccharide having the ability to suppress acrylamide production. For example, α, α-trehalose is a high-purity water-containing crystal α, α-trehalose (trade name “Trehha” sold by Hayashibara Corporation), and α, β-trehalose is a reagent grade crystal α, β- Trehalose (trade name “Neotrehalose” sold by Hayashibara Biochemical Laboratories Co., Ltd.) has reduced palatinose as powdered reduced palatinose (Mitsui Sugar Co., Ltd., trade name “Paratinit”) or (Selestar Japan sales, product name “ "Isomadex"), etc., as D-mannitol, powder crystal mannitol (sold by Towa Kasei Co., Ltd., trade name "mannitol"), etc., as D-erythritol, powder crystal erythritol (sold by Mitsubishi Chemical Foods, (Product name "Erythritol") or (Niken Chemicals Co., Ltd., trade name "Eli Sweet"), etc. As the cyclodextrin, such as high-purity β- cyclodextrin (Ensuiko Sugar Refining Co., Ltd. sold under the trade name of "Dixie Pearl β-100") can be advantageously used.

  Examples of the phenolic substance having acrylamide production-inhibiting ability in the present invention include commercially available reagent grade catechins such as catechin, epicatechin and epigallocatechin, quercetin, isoquercitrin, rutin, naringin, hesperidin and the like. Flavonoids, kaempferol, cinnamic acid, quinic acid, 3,4-dihydrocinnamic acid, 3-coumaric acid, 4-coumaric acid, p-nitrophenol, curcumin, scopoletin, propyl p-hydroxybenzoate and proanthocyanidins Alternatively, not only phenolic substances such as these saccharide derivatives but also their mixtures and saccharide derivatives sold as health foods can be advantageously used. For example, green tea polyphenols (sold by Tokyo Food Techno Co., Ltd., registered trademark “Polyphenone”) and the like as catechins, and sugar-transferred rutin (sold by Hayashibara Corporation, trade name “αG rutin”) as flavonoids. Flavonoids such as sugar transfer naringin, sugar transfer hesperidin (trade name “αG Hesperidin”, trade name “αG Hesperidin”) and sugar transfer isoquercitrin (trade name “Sanmerin”, Saneigen FFI Co., Ltd.) Derivatives can also be used advantageously.

  In the present invention, in order to sufficiently exhibit the acrylamide production-inhibiting action, when the organic substance having an acrylamide production-inhibiting ability is a saccharide, the organic substance having an amino group or the saccharide having an acrylamide-producing ability has a molar ratio. The ratio is usually 0.5 or more, preferably 0.75 or more, more preferably 1.0 or more. If the molar ratio is less than 0.5, the acrylamide formation inhibitory action due to coexistence may not be sufficiently exhibited. Moreover, when the organic substance which has acrylamide production inhibitory ability is a phenolic substance, it is 0.004 or more normally by molar ratio with respect to the organic substance which has an amino group, or saccharide | sugar which has acrylamide production ability, Preferably it is 0.00. It is desirable to contain 01 or more, more preferably 0.02 or more. If the molar ratio is less than 0.004, the acrylamide production inhibitory action due to coexistence may not be fully exhibited.

  The heat treatment referred to in the present invention means a heat treatment at a temperature at which an organic substance having an amino group contained in an edible material reacts with a sugar having acrylamide-forming ability to produce acrylamide, and is usually , 80 ° C. or higher, specifically about 100 ° C. to 240 ° C. The heating method is not particularly limited, and examples thereof include baking, frying, roasting, microwave heating, retort heating, induction heating, pressure heating, boiling, steaming, boiling, Examples of the method include heat sterilization.

  In general, the amount of acrylamide produced from an organic substance having an amino group contained in an edible material and a saccharide capable of producing acrylamide increases as the heating temperature increases and the heating time increases. Furthermore, as shown in the experimental section described later, the amount of acrylamide generated increases as the moisture content of the sample (edible material) decreases even at the same heating temperature and heating time. The organic substance having the ability to suppress acrylamide production in the present invention can suppress the production of acrylamide in both cases where the moisture content of the sample (edible material) is high and low. In particular, in order to remarkably suppress the formation of acrylamide, the water content of the sample (edible material) during the heat treatment is usually preferably about 10% by mass or more.

  Various compositions such as foods, drinks, cosmetics, pharmaceuticals, or intermediate products thereof in which acrylamide production is suppressed can be produced by using the method for suppressing acrylamide production of the present invention. The operation of adding an organic substance having an ability to suppress acrylamide generation to an edible material for producing various compositions such as foods, cosmetics or pharmaceuticals may be performed before the edible material is heat-treated, The raw material for preparing the edible material may be added or added and / or mixed immediately before the heat treatment. As a specific method of inclusion, for example, methods such as mixing, kneading, dissolving, dispersing, suspending, emulsifying, penetrating, coating, spraying, coating, pouring, and dipping can be appropriately selected. In addition, if necessary, an organic substance having an ability to suppress acrylamide production, such as a sugar and / or a phenolic substance, may be produced and contained in plant cells such as fruits and vegetables by genetic manipulation. An edible material can also be advantageously implemented.

  In the present invention, α, α-trehalose, α, β-trehalose, reduced palatinose, α-glucosyl α, α-trehalose, α-maltosyl α, α-trehalose, D-mannitol, D- having acrylamide production inhibitory ability One or more carbohydrates selected from erythritol and β-cyclodextrin and / or catechins such as catechin, epicatechin and epigallocatechin, flavonoids such as quercetin, isoquercitrin, rutin, naringin and hesperidin , Kaempferol, cinnamic acid, quinic acid, 3,4-dihydrocinnamic acid, 3-coumaric acid, 4-coumaric acid, p-nitrophenol, curcumin, scopoletin, propyl p-hydroxybenzoate and proanthocyanidins One or more selected from saccharide derivatives of It is also possible to advantageously carry out an acrylamide production inhibitor by containing the above-mentioned phenolic substance as an active ingredient and appropriately combining them as necessary.

  Further, in the present invention, an edible material-containing composition having an acrylamide production-inhibiting ability by containing the organic substance having the ability to inhibit acrylamide production in an edible material that produces acrylamide by heat treatment. It can also be advantageously carried out. Further, by combining the saccharide and / or phenolic substance having the ability to suppress acrylamide generation with the organic substance having the amino group and / or the saccharide having the acrylamide generating ability, It is also advantageous to finish the composition with More specifically, for example, glycine, L-alanine, L-valine, L-leucine, L-isoleucine, L-serine, L-threonine, L-aspartic acid, L-glutamic acid, L-asparagine Amino acid selected from L-glutamine, L-lysine, L-arginine, L-cysteine, L-methionine, L-phenylalanine, L-tryptophan and L-proline, or a peptide containing these amino acids as constituent amino acids Or an organic substance having an amino group such as protein, one or more monosaccharides selected from D-xylose, L-arabinose, D-glucose, D-fructose and D-galactose, D-xylose, L- From arabinose, D-glucose, D-fructose and D-galactose One or more reducing oligosaccharides containing one or more saccharides as constituent sugars, non-reducing oligosaccharides containing D-fructose as constituent sugars, and L-ascorbic acids In the case of saccharides and the like, although depending on the amount of saccharides coexisting or the amount of organic substances having amino groups, as saccharides having an ability to suppress acrylamide production, for example, α, α-trehalose and / or α , Β-trehalose in a molar ratio of 0.5 or more, preferably 0.75 or more, more preferably 1.0 or more, and / or a phenolic substance having acrylamide production inhibitory ability, for example, rutin, naringin and / or Alternatively, hesperidin may contain 0.004 or more, preferably 0.01 or more, more preferably 0.02 or more in a molar ratio in the seasoning or sugar. Thus, the resulting composition such as seasonings and sugars becomes a composition having an ability to suppress the formation of acrylamide, and even if this is heat-treated alone or with other materials, the formation of acrylamide is not caused. It is possible to obtain an excellent effect of being remarkably suppressed and substantially preventing its generation.

  In addition, the organic substance having the ability to suppress the formation of acrylamide is mixed with L-ascorbic acids to contain the L-ascorbic acid-containing composition for various uses having the ability to suppress the formation of acrylamide, preferably Further, it can be advantageously carried out as a solid composition such as powder, granule, tablet and the like which is easy to handle and has good storage stability. Such an L-ascorbic acid-containing composition is a composition that requires L-ascorbic acid, and is used for the production of a composition containing an edible material that may generate acrylamide by heat treatment. By using it, it can suppress effectively that acrylamide produces | generates in those manufacturing processes. Such an L-ascorbic acid-containing composition is used to produce various compositions such as high-safety and high-quality foods, cosmetics, pharmaceuticals, or intermediate products thereof with enhanced L-ascorbic acid (vitamin C). Can be advantageously used.

  Among the compositions that can be produced by adopting the method for inhibiting acrylamide production of the present invention, foods and drinks include foods and drinks produced by heat treatment for animals including humans and pets, such as potato chips and french fries. , Fried onion, corn chips, banana chips, vegetable chips, fried rice crackers, fried confectionery such as university candy, kaki kempi, karinto, snacks Deep-fried foods such as noodles (instant noodles), rice crackers, taro, dorayaki, Japanese confectionery such as buns, salmon roasts, takoyaki, wheat koshi, western confectionery or snack foods such as biscuits, crackers, cookies, pretzels, cereals, popcorn, Bread, pizza, pie, sponge cake, waffle, castella, dough Processed wheat products such as tsutsu, processed meat products such as ham and sausage, processed eggs such as roasted eggs, dashi roll eggs, broiled eggs, boiled eggs, fishery processed products such as kamaboko, chikuwa, hanpen, fish sausage, yakiniku, Grilled chicken, grilled pork, grilled fish, grilled rice ball, grilled rice cake, fried rice, hamburger, dumplings, gratin, hayashi rice, curry rice, risotto, quiche and other prepared foods, amino acid beverage, peptide beverage, soy milk beverage, milk beverage, lactic acid beverage, fruit juice beverage, Vegetable drinks, cocoa drinks, coffee drinks, soft drinks such as amazake and shiruko, tea processed products and tea drinks such as barley tea, roasted tea, Chinese tea and tea, juices such as fruits, vegetables and herbs, dried fruits, preserves, sauces and chutneys , Jam, marmalade, spread, jelly, candy, canned, bottled, boiled, fried, grilled Fruits, processed vegetables, sweet chestnuts, peanuts, almonds, chocolate powder, coffee powder, coffee, cocoa, curry powder, green sesame, roasted rice, roasted wheat flour, roasted wheat germ food, roasted rice Roasted processed foods such as embryo foods, seasoned processed agricultural products, processed meat products, processed egg products, processed fishery products, foods and beverages such as bottles and cans, cookies, biscuits, beef jerky, Various foods and drinks such as pet foods such as processed vegetable products, feeds and feeds can be mentioned. These foods and drinks obtained using the method for inhibiting acrylamide production of the present invention have a significantly reduced amount of acrylamide even when heat-treated, and are safe and routine with little risk of causing carcinogenesis or neuropathy. It can be advantageously used as a food and drink that can be consumed.

  Among the compositions that can be produced by adopting the method for inhibiting acrylamide production of the present invention, cosmetics include, for example, lotions, creams, emulsions, gels, powders, pastes, blocks, soaps, cosmetic soaps, and skin washing powders. , Face washing cream, face washing foam, facial rinse, body shampoo, body rinse, shampoo, rinse, hair wash powder and other cleansing cosmetics, set lotion, hair blow, tics, hair cream, pomade, hair spray, hair liquid, hair tonic, hair Lotion, hair nourishing, hair dye, scalp hair treatment, lotion, vanishing cream, emollient cream, emollient lotion, pack cosmetic (jelly peel-off type, jelly-type wipe, paste-type washout, powder )), Cleansing cream, cold cream, hand cream, hand lotion, emulsion, moisturizer, after shaving lotion, shaving lotion, pre-shave lotion, after shaving cream, after shaving foam, pre-shave cream, cosmetic oil, baby oil, etc. Cosmetics, foundation (liquid, cream, solid, etc.), talcum powder, baby powder, body powder, perfume powder, makeup base, funny (cream, paste, liquid, solid, powder, etc.), eye shadow, Makeup cosmetics such as eye cream, mascara, eyebrows, eyelash cosmetics, blusher, cheek lotion, perfume, fragrance perfume, powder perfume, eau de cologne, perfume cologne, eau de toilette Incense cosmetics, tanning cream, tanning lotion, tanning oil, sunscreen cream, tanning lotion, tanning sunscreen cosmetics, manicure, pedicure, nail color, nail lacquer, enamel remover, nail cream, nail cosmetics Nail cosmetics such as eyeliner cosmetics, lipsticks, lip balm, lip cosmetics such as lip gloss, lip gloss, oral cosmetics such as toothpaste and mouthwash, bath cosmetics such as bath salt, bath oil, bath cosmetics, etc. Can be mentioned. These cosmetics obtained by using the method for inhibiting acrylamide production of the present invention have a significantly reduced amount of acrylamide even when subjected to heat treatment, and are safe and daily with little risk of causing carcinogenesis or neuropathy. It can be advantageously used as a usable cosmetic.

  Among the compositions that can be produced by adopting the method for inhibiting acrylamide production according to the present invention, examples of pharmaceuticals include, for example, drinks, extracts, elixirs, capsules, granules, pills, eye ointments, and oral mucosa patches. Agents, suspensions, emulsions, plasters, suppositories, powders, spirits, tablets, syrups, injections, tinctures, eye drops, ear drops, nasal drops, troches, ointments, fragrances Nasal sprays, limonades, liniments, fluid extracts, lotions, poultices, sprays, coatings, baths, patches, pasta, poultices and the like. These pharmaceuticals obtained by using the method for inhibiting acrylamide production of the present invention have a significantly reduced amount of acrylamide even when subjected to heat treatment, and are safe and daily with little risk of causing carcinogenesis or neuropathy. It can be advantageously used as a pharmaceutical that can be administered.

  Hereinafter, the present invention will be specifically described by experiments.

<Experiment 1: Production of acrylamide from amino acids and various sugars by heat treatment>
The acrylamide production test from amino acids and various sugars by heat treatment is performed according to the method of Donald S. Mottram et al. Described in Non-Patent Document 2, using L-asparagine as an amino acid as follows. went. D-glucose, D-fructose, D-galactose, α, α-trehalose, α, β-trehalose, maltose, sucrose, lactose, or 1 mmol of L-ascorbic acid was weighed, and 1 mmol of L-asparagine was collected in advance. Each was added to a 20 ml test tube with a stopper, and 1 ml of 0.5 M phosphate buffer (pH 6.0) was added thereto. Next, each test tube was sealed and heat-treated in an oil bath (oil bath) at 150 ° C. for 20 minutes. Immediately after the heat treatment, the mixture was cooled to room temperature in running water. Acrylamide produced in the sample is a brominated derivative (2-bromo) according to “Guidelines for test methods for evaluation of chemicals for water supply” (former Ministry of Health and Welfare, Water Environment Department, Water Environment Department, March 2000). After being converted to propenamide, the peak of retention time corresponding to the standard acrylamide derivative was quantified as a derivative derived from acrylamide in the sample using gas chromatography.

Gas chromatography analysis was performed under the following conditions.
(Gas chromatography conditions)
Gas chromatograph: Shimadzu GC-14A
Column: TC-FFAP capillary column (manufactured by GL Sciences Inc., inner diameter 0.53 mm, length 30 m, film thickness 1 μm)
Column temperature: held at 120 ° C. for 5 minutes, then heated to 240 ° C. at a heating rate of 7.5 ° C./min. Carrier gas: helium (1 ml / min)
Detection: Hydrogen flame ionization detector (FID)
Sample inlet temperature: 250 ° C
Sample injection volume: 4 μl (total volume injection)

  The test results are shown in Table 1. The acrylamide production rate (%) was shown as a relative value when the amount of acrylamide produced when D-glucose was used as a carbohydrate was 100%. Throughout Experiments 1 to 10, the amount of acrylamide produced (mg) in the table was shown as a value converted per mol of L-asparagine.

  As shown in Table 1, in the heat treatment with L-asparagine, D-glucose, D-fructose, and L-ascorbic acid produced a relatively large amount of acrylamide. Among them, the amount of acrylamide produced from L-ascorbic acid was a large amount of 4 times or more that of D-glucose. Although D-glucose and maltose, sucrose, and lactose were less in amount than D-glucose and D-fructose, acrylamide was produced by heat treatment with L-asparagine. On the other hand, no acrylamide was formed from L-asparagine and α, α-trehalose or α, β-trehalose even after heat treatment. Although it was known that α, α-trehalose and α, β-trehalose, which are non-reducing carbohydrates, were not inherently susceptible to the Maillard reaction with amino acids, this was also confirmed by the results in Table 1. Similarly, sucrose, which is a non-reducing saccharide, was confirmed to produce acrylamide because sucrose is a saccharide that is susceptible to thermal decomposition, and D-glucose and D-fructose produced by decomposition of sucrose by heat treatment. Is presumed to have reacted with L-asparagine. Hereinafter, experiments when D-glucose is used as a saccharide having an acrylamide-forming ability in heat treatment with L-asparagine are performed as Experiments 2 to 8, and experiments when L-ascorbic acid is used are performed as Experiment 9 To 12.

<Experiment 2: Effect of Coexistence of Various Carbohydrates on Production of Acrylamide from L-Asparagine and D-Glucose>
The influence of various carbohydrates on the production of acrylamide from L-asparagine and D-glucose by heat treatment was investigated. 1 mmol of any of the carbohydrates shown in Table 2 was added to a 20-ml stoppered test tube in which 1 mmol of L-asparagine and 1 mmol of D-glucose had been collected in advance. However, 720 mg (corresponding to about 0.63 to 0.74 mmol) was uniformly used for the two kinds of α-cyclodextrin and β-cyclodextrin. Otherwise, the same method as in Experiment 1 was used to determine the amount of acrylamide produced. Only L-asparagine and D-glucose were used, and no other carbohydrate was added as a control. The results are shown in Table 2. The acrylamide production rate (%) was shown as a relative value when the acrylamide production amount (mg) when only L-asparagine and D-glucose were used was 100%.

  As is clear from the results in Table 2, it has been found that depending on the type of carbohydrate, coexistence significantly suppresses the production of acrylamide from L-asparagine and D-glucose in the heat treatment. Specifically, α, α-trehalose, α, β-trehalose, reduced palatinose, α-glucosyl α, α-trehalose, D-mannitol, D-erythritol, and β-cyclodextrin are L-asparagine and D-glucose. It was confirmed that the production rate of acrylamide from the above was suppressed to less than 50%, and in particular, α, α-trehalose and α, β-trehalose significantly reduced the production rate (%) of acrylamide to less than 20%. Although the saccharides having the ability to suppress the formation of acrylamide are all non-reducing, it has been known that non-reducing carbohydrates are less likely to cause Maillard reaction with organic substances having amino groups. However, it is a completely unexpected finding that the production of acrylamide due to the reaction between the reducing sugar and the organic substance having an amino group is remarkably suppressed, and shows an active action effect.

<Experiment 3: Effect of D-glucose amount on acrylamide production from L-asparagine and D-glucose and effect of coexistence of α, α-trehalose>
The influence of the amount of D-glucose on the acrylamide production from L-asparagine and D-glucose in the heat treatment and the effect of coexistence with α, α-trehalose that significantly suppressed the production of the acrylamide in Experiment 2 were examined. In a 20-ml test tube with a stopper, from which 1 mmol of L-asparagine has been previously collected, D-glucose is added at 0.01, 0.10, 0.25, 0.50, 1.00, 1.33, or Processing was performed in the same manner as in Experiment 1 except that 2.00 mmol was added, and the amount of acrylamide produced was quantified. In addition, a test system in which 1 mmol of α, α-trehalose was further added to the reaction system was also tested in the same manner. The results are shown in Table 3. In the table, the molar ratio is the molar ratio of α, α-trehalose to D-glucose, and the acrylamide production rate (%) is the acrylamide when no α, α-trehalose is added in each D-glucose amount. The relative value of the α, α-trehalose added system when the production amount (mg) is 100% is shown.

  As is apparent from the results in Table 3, in the α, α-trehalose-free system, the amount of acrylamide produced from L-asparagine increased as the amount of D-glucose increased. Acrylamide produced from 1 mmol of L-asparagine was almost constant with no significant difference in the range of D-glucose amount from 0.50 mmol to 2.00 mmol. On the other hand, in the 1 mmol α, α-trehalose addition system, an increase in the amount of acrylamide with the increase in the amount of D-glucose was observed, but the level was low, and the molar ratio of α, α-trehalose to D-glucose was within the tested range. In the case of 0.5 or more, the acrylamide production rate (%) in the α, α-trehalose added system was less than 50% in the non-added system. In particular, α, α-trehalose is less than 25% when the molar ratio of α, α-trehalose to D-glucose is 0.75 or more, and less than 20% when the molar ratio is 1 or more. %) Was significantly suppressed.

<Experiment 4: Effect of α, α-trehalose coexistence amount on acrylamide production from L-asparagine and D-glucose>
In Experiment 2, the dose dependency of the acrylamide production inhibitory ability was examined for α, α-trehalose, which had a remarkable effect of inhibiting acrylamide production from L-asparagine and D-glucose during heat treatment. In a 20-ml test tube with a stopper, from which 1 mmol of L-asparagine and 1 mmol of D-glucose had been collected in advance, 0.00, 0.10, 0.25, 0.50, 0.75, 1.00, Treatment was performed using the same method as in Experiment 1 except that 1.50 or 2.00 mmol of α, α-trehalose was added, and the amount of acrylamide produced was quantified. The results are shown in Table 4. The acrylamide production rate (%) was shown as a relative value when the amount of acrylamide produced (mg) without addition of α, α-trehalose was 100%.

  As is apparent from the results in Table 4, the amount of acrylamide produced from equimolar L-asparagine and D-glucose decreases as the amount of α, α-trehalose to coexist increases, and α, α-trehalose is In a dose-dependent manner, acrylamide production from L-asparagine and D-glucose in the heat treatment is suppressed. When the molar ratio to L-asparagine or D-glucose is 1 or more, the degree of inhibition is almost constant, and acrylamide is produced. The rate (%) was suppressed to less than 15%. Moreover, under this condition, by using α, α-trehalose having a molar ratio of 0.5 or more with respect to L-asparagine or D-glucose, the production rate (%) of acrylamide is suppressed to less than 50%. It was found that by using α, α-trehalose of 0.75 or more, it was suppressed to less than 25%.

<Experiment 5: Production amount of acrylamide from various amino acids and D-glucose, and influence of coexistence of α, α-trehalose on acrylamide production>
The amount of acrylamide produced from various amino acids and D-glucose and the influence of α, α-trehalose coexistence on acrylamide production were investigated. The amount of acrylamide produced was treated in the same manner as in Experiment 1 except that 1 mmol of D-glucose was added to a 20-ml stoppered test tube in which 1 mmol of various amino acids shown in Table 5 were previously collected. (Mg) was measured. Further, a test system in which 1 mmol of α, α-trehalose was further coexisted with the reaction system was also tested in the same manner. The results are shown in Table 5. The acrylamide production rate (%) indicates the relative value of the α, α-trehalose addition system when the acrylamide production amount (mg) in each amino acid without addition of α, α-trehalose is 100%. It was.

  As shown in Table 5, the amount of acrylamide produced by heating with D-glucose varies depending on the type of amino acid, and two amino acids producing relatively large amounts of acrylamide are L-asparagine and L-isoleucine. It was. As is apparent from the results in Table 5, it was found that α, α-trehalose significantly suppressed acrylamide production from L-isoleucine as in the case of L-asparagine. Although acrylamide is produced less than L-asparagine and L-isoleucine, glycine, L-alanine, L-valine, L-leucine, L-serine, L-threonine, L-aspartic acid, L- In the case of amino acids such as glutamic acid, L-glutamine, L-lysine, L-arginine, L-cysteine, L-methionine, L-phenylalanine, L-tryptophan and L-proline, α, α-trehalose is In any case, this generation was suppressed to some extent. L-valine, L-leucine, L-isoleucine, L-threonine, L-methionine, L-phenylalanine, L-tryptophan and the like are known as essential amino acids essential for the growth and maintenance of humans and animals. ing.

  In Experiment 1 to Experiment 5, the acrylamide formation reaction by heat treatment was tested using an aqueous solution model with relatively high water content. In the following Experiments 6 to 8, a drying model having a relatively low water content that is closer to an actual edible material was used. Further, in order to completely dissolve L-asparagine at the stage of sample preparation, the amount used for the test was reduced to 0.1 mmol. In the dry model test, first, pharmacopoeia potato starch is used as a base material, and 0.1 mmol of L-asparagine and 0.1 mmol of D-glucose and a buffer solution are added thereto to obtain a paste, which is appropriately dried. Samples having various moisture contents were prepared by the above. Next, this was sealed and heat-treated, and the effects of acrylamide formation and carbohydrate coexistence on it were examined under various water content conditions.

<Experiment 6: Effect of coexistence of various non-reducing carbohydrates on the amount of acrylamide produced from L-asparagine and D-glucose by heat treatment>
The effect of the coexistence of various carbohydrates on the amount of acrylamide produced from L-asparagine and D-glucose by heat treatment was examined in a dry model test. In a 20-ml test tube with a stopper, from which 1 g of pharmacopeel potato starch, 0.1 mmol (13 mg) of L-asparagine and 0.1 mmol (18 mg) of D-glucose had been collected, 0.1 mmol / ml) was added to 1 ml and 0.05 M phosphate buffer (pH 6.0) 0.25 ml, and the mixture was stirred to obtain a paste having a water content of about 50%. Next, when the water content was reduced to about 10%, it was vacuum dried at 60 ° C. for 2 hours, and then stored in a humidity desiccator with a relative humidity of 22.4% for 2 days. Further, when the moisture content was reduced to about 1%, it was vacuum-dried at 60 ° C. for 16 hours. Next, after measuring the water content of each sample, these were heat-treated in an oil bath (oil bath) at 180 ° C. for 20 minutes, and the produced acrylamide was measured by gas chromatography. In parallel, a sample (paste-like material having a water content of about 50%) in which moisture was not adjusted by vacuum drying was also tested in the same manner. In addition, α, α-trehalose, α, β-trehalose, sucrose, and D-mannitol, which showed a relatively strong acrylamide production inhibitory effect in the aqueous solution model test of Experiment 2, were used as the coexisting test carbohydrates, and the same non-reduction A total of six kinds of carbohydrates, D-sorbitol and maltitol, were used. The moisture content of the sample was measured using an electronic moisture meter (manufactured by Shimadzu Corporation, trade name “MOISTURE BALANCE EB-330MOC”). Acrylamide was measured by gas chromatography in the same manner as in Experiment 1 after adding 10 ml of deionized water to each test tube after heat treatment and stirring well. Only L-asparagine and D-glucose were used, and no other carbohydrate was added as a control. The results are shown in Table 6. The acrylamide production rate (%) was shown as a relative value when the amount of acrylamide production (mg) of the control was 100%.

  As is clear from the results in Table 6, α, α-trehalose, α, β-, similar to the results of Experiment 2, were obtained under any conditions where the water content of the sample was about 50%, about 10% and about 1%. When trehalose and D-mannitol were allowed to coexist, it was confirmed that the production of acrylamide from L-asparagine and D-glucose by heating was remarkably suppressed. Further, in detail, as the moisture content of the sample decreases to about 50%, about 10%, and about 1%, the effect of suppressing the formation of acrylamide by the coexistence of carbohydrate tends to decrease, but the moisture content is about It has been found that when these carbohydrates are allowed to coexist in 10% or more of the samples, the production of acrylamide can be well suppressed. On the other hand, sucrose was different from the result of Experiment 2, and the production rate (%) of acrylamide increased to 113 to 127% of the control. This is presumably because heating under conditions with a relatively low water content promoted the decomposition of sucrose, resulting in a saccharide with strong acrylamide-forming ability. Moreover, the acrylamide production inhibitory effect of D-sorbitol and maltitol was weak and was almost the same as the result of Experiment 2.

<Experiment 7: Influence of moisture content of sample and heating temperature on acrylamide production from L-asparagine and D-glucose and influence of coexistence of α, α-trehalose>
Further details on the effect of water content and heating temperature of acrylamide on the amount of acrylamide produced from L-asparagine and D-glucose, and the effect of coexisting α, α-trehalose as a saccharide having acrylamide production-inhibiting ability I investigated. Samples with different moisture contents were prepared by variously changing the time for vacuum drying at 60 ° C., and the same as Experiment 6 except that the temperature of the heat treatment was tested at 150 ° C., 180 ° C. and 200 ° C. The amount of acrylamide produced was measured. A control treated in the same manner in a test system without α, α-trehalose was used as a control. The results are shown in Table 7. The acrylamide production rate (%) was expressed as a relative value when the acrylamide production amount (mg) at each water content of the control sample was 100%.

  As is apparent from the results in Table 7, acrylamide is formed by the coexistence of L-asparagine and D-glucose and α, α-trehalose at any heating temperature of 150 ° C., 180 ° C. and 200 ° C. Well suppressed. Similar to the result of Experiment 6, although the acrylamide production suppression effect by α, α-trehalose tended to weaken as the water content of the sample decreased, when the water content of the sample was about 10% or more In the presence of L-asparagine and D-glucose and equimolar α, α-trehalose at any heating temperature of 150 ° C., 180 ° C. and 200 ° C., acrylamide production is reduced to less than 30% of the control. It has been found that it can be significantly reduced.

<Experiment 8: Effect of moisture content of sample and amount of α, α-trehalose coexisting on acrylamide production from L-asparagine and D-glucose>
The influence of the water content of the sample and the amount of α, α-trehalose coexisting on the amount of acrylamide produced from L-asparagine and D-glucose was examined. The amount of acrylamide produced was the same as in Experiment 6 except that the amount of α, α-trehalose added was changed to 0.010, 0.025, 0.050, 0.075, 0.100 and 0.500 mmol. Was measured. A control treated in the same manner in a test system without α, α-trehalose was used as a control. The results are shown in Table 8. The acrylamide production rate (%) was shown as a relative value when the amount of acrylamide production (mg) in the control was 100%.

  As is apparent from the results in Table 8, acrylamide production from L-asparagine and D-glucose is α, at any of the conditions where the moisture content of the sample is about 50%, about 10% and about 1%. As the amount of α-trehalose added was increased, the amount was suppressed. In this dry model test, α, α-trehalose having a molar ratio of 0.5 or more with L-asparagine or D-glucose coexists to produce acrylamide when the water content of the sample is about 1%. It was found that the rate (%) can be suppressed to less than 65%, and the acrylamide production rate (%) can be suppressed to less than 55% when the water content of the sample is about 10%.

  From the results of the dry model tests shown in Experiments 6 to 8 above, (1) even when the moisture content of the sample is low, heating can be achieved by coexisting α, α-trehalose, α, β-trehalose and mannitol. That the formation of acrylamide from L-asparagine and D-glucose by treatment can be remarkably suppressed; and (2) when the water content of the sample is about 10% or more, α, α in an equimolar amount with L-asparagine and D-glucose. -The presence of trehalose can remarkably suppress the formation of acrylamide, and (3) the presence of 0.5 or more α, α-trehalose in a molar ratio to L-asparagine or D-glucose, It was found that even when the content is small, the production rate (%) of acrylamide can be suppressed to less than 65%.

  Next, it was found from the results of Experiment 1 that L-ascorbic acid has higher acrylamide-producing ability than D-glucose. In the following Experiments 9 to 12, as saccharides having acrylamide-producing ability, Experiments were performed using L-ascorbic acid. Further, in order to completely dissolve L-asparagine, the amount used for the test was reduced to 0.1 mmol. Furthermore, in Experiments 10 to 12, the heating temperature was set to 100 ° C. in consideration of cooking conditions of edible materials such as fruits or vegetables containing L-ascorbic acid.

<Experiment 9: Effect of Coexistence of Various Carbohydrates on Production of Acrylamide from L-Asparagine and L-Ascorbic Acid>
The influence of various carbohydrates on the production of acrylamide from L-asparagine and L-ascorbic acid by heat treatment was examined. To a 20-ml test tube with a stopper, from which 0.1 mmol of L-asparagine has been collected in advance, a 0.1 M L-ascorbic acid aqueous solution and a 0.1 M sodium L-ascorbate aqueous solution are appropriately mixed to adjust the pH. 1 ml of the mixed solution prepared to 4.0 (0.1 mmol as L-ascorbic acid) was added, and then 0.1 mmol of any of the carbohydrates shown in Table 6 was added. However, three kinds of α-maltotriosyl α, α-trehalose, α-cyclodextrin and β-cyclodextrin were uniformly used in an amount of 200 mg (corresponding to about 0.17 to 0.24 mmol). The amount of acrylamide produced was quantified using the same method as in Experiment 1 except that the heat treatment conditions were 150 ° C. and 20 minutes. Only L-asparagine and L-ascorbic acid were used, and no other carbohydrate was added as a control. The results are shown in Table 9. The acrylamide production rate (%) is shown as a relative value when the amount of acrylamide produced (mg) when only L-asparagine and L-ascorbic acid are used is 100%.

  As is apparent from the results in Table 9, L-asparagine in the heat treatment is caused by the presence of a specific saccharide in the same manner as in the case where D-glucose is used as the acrylamide-producing saccharide in Experiment 2. It has been found that the production of acrylamide from L-ascorbic acid is significantly suppressed. Specifically, α, α-trehalose, α, β-trehalose, D-mannitol, D-erythritol, reduced palatinose, α-glucosyl α, α-trehalose, α-maltosyl α, α-trehalose and β-cyclodextrin are , The rate of acrylamide formation from L-asparagine and L-ascorbic acid is suppressed to less than 50%. In particular, α, α-trehalose and α, β-trehalose significantly reduce the acrylamide generation rate (%) to less than 16%. It was confirmed to suppress. In this experiment, sucrose did not suppress the production of acrylamide, but on the contrary, the result was different from the result of Experiment 2. This is presumably because sucrose was hydrolyzed to D-glucose and D-fructose under the heat treatment conditions, and these reacted with L-asparagine to produce acrylamide. In addition, considering the results of this experiment and Experiment 2, α-maltosyl α, α-trehalose is a saccharide that has the ability to suppress the formation of acrylamide, similar to α, α-trehalose and α-glucosyl α, α-trehalose. It is clear that there is.

<Experiment 10: Effect of reaction pH on acrylamide production from L-asparagine and L-ascorbic acid and effect of coexistence of α, α-trehalose>
The influence of reaction pH on the acrylamide production from L-asparagine and L-ascorbic acid in the heat treatment and the effect of coexistence with α, α-trehalose were examined. To a 20-ml test tube with a stopper, from which 0.1 mmol of L-asparagine has been collected in advance, a 0.1 M L-ascorbic acid aqueous solution and a 0.1 M sodium L-ascorbate aqueous solution are appropriately mixed to adjust the pH. 1 ml (0.1 mmol as L-ascorbic acid) was added to each of the mixed solutions prepared to be 3, 4, 5, 6, or 6.5, and the heat treatment conditions were 100 ° C. for 20 minutes. The amount of acrylamide produced was quantified using the same method. A test system in which 0.1 mmol of α, α-trehalose was further added to the above reaction system was also tested in the same manner. The results are shown in Table 10. In the table, acrylamide production rate (%) is the amount of acrylamide produced when only L-asparagine, L-ascorbic acid and sodium L-ascorbate are used and no α, α-trehalose is added under each pH condition. The relative value of the α, α-trehalose addition system when the mg) is 100% is shown.

  As shown in Table 10, in both the α, α-trehalose non-added system and the added system, the change in pH before and after the heat treatment was small. It was also found that acrylamide was produced even at a heating temperature of 100 ° C., although the amount of sample used was small and the heating temperature was low, so that the amount produced was small. As is clear from the results in Table 10, the amount of acrylamide produced in the α, α-trehalose-free system increased as the reaction pH increased, and increased rapidly at pH 6 and pH 6.5. In the α, α-trehalose-added system, the amount of acrylamide produced is significantly lower at any reaction pH than in the non-added system, and the presence of α, α-trehalose can provide a remarkable production-suppressing effect. confirmed.

<Experiment 11: Effect of Coexisting Amount of α, α-Trehalose on Acrylamide Production from L-Asparagine and L-Ascorbic Acid>
Regarding α, α-trehalose, the dose dependency of the ability to suppress acrylamide production from L-asparagine and L-ascorbic acid in heat treatment was examined. To a 20 ml test tube with a stopper, from which 0.1 mmol of L-asparagine had been collected in advance, 1 ml of a mixed solution of L-ascorbic acid and sodium L-ascorbate having a pH of 6 used in Experiment 10 (0 as L-ascorbic acids). 0.1 mmol), and then 0.000, 0.010, 0.025, 0.050, 0.075, 0.100, 0.150, 0.250, or 0.500 mmol of α, α-trehalose The amount of acrylamide produced was quantified by the same method as in Experiment 1 except that each of the above was added. The results are shown in Table 11. Acrylamide production rate (%) is relative to L-asparagine, L-ascorbic acid, and sodium L-ascorbate, with no addition of α, α-trehalose and 100% acrylamide production (mg). Indicated by value.

  As is apparent from the results in Table 11, the amount of acrylamide produced from L-asparagine and L-ascorbic acid decreases as the amount of α, α-trehalose to coexist increases, and α, α-trehalose Dependently, acrylamide production from L-asparagine and L-ascorbic acid in heat treatment is suppressed, and when the molar ratio to L-asparagine or L-ascorbic acid is 1 or more, the degree of inhibition is almost constant, and acrylamide is produced. The rate (%) was suppressed to less than 15%. Under the present conditions, by using α, α-trehalose having a molar ratio of 0.5 or more with respect to L-asparagine or L-ascorbic acid, the production rate (%) of acrylamide is suppressed to 75%, and the molar ratio is 0.00. It was found that by using 75 or more α, α-trehalose, it was suppressed to less than 50%.

<Experiment 12: Influence of pH and coexistence of α, α-trehalose on acrylamide production from L-asparagine and L-ascorbic acid derivative>
In place of L-ascorbic acid, L-ascorbic acid 2-glucoside (trade name “AA2G” sold by Hayashibara Biochemical Laboratories Co., Ltd.) or L-ascorbic acid 2-phosphate (Roche Vitamin Co., Ltd.) as an L-ascorbic acid derivative L-asparagine and L-ascorbic acid derivative in the same manner as in Experiment 10 except that the heat treatment was performed at 100 ° C. and 125 ° C. using a trisodium salt, registered trademark “Stay-C 50”). The influence of pH and the coexistence of α, α-trehalose on the amount of acrylamide produced from the above was investigated. Moreover, it replaced with the L-ascorbic acid derivative and tested similarly as the control except having used L-ascorbic acid. The results of L-ascorbic acid, L-ascorbic acid 2-glucoside, and L-ascorbic acid 2-phosphate are shown in Table 12, Table 13, and Table 14, respectively. In the table, the acrylamide production rate (%) is the value of the α, α-trehalose added system when the amount of acrylamide produced (mg) is 100% when no α, α-trehalose is added under each pH condition. Relative values are shown.

  As is clear from Table 12, in the case of L-ascorbic acid, the same results as in Experiment 10 were obtained when the heat treatment temperature was 100 ° C, and α, α-trehalose was not obtained when the heat treatment temperature was 125 ° C. The amount of acrylamide produced in the addition system increased as the reaction pH increased, and increased rapidly at pH 6 and pH 6.5. In the α, α-trehalose added system, the amount of acrylamide produced at any reaction pH was significantly lower than that in the non-added system. On the other hand, as is apparent from Table 13, L-ascorbic acid 2-glucoside, which is an L-ascorbic acid derivative, is more stable in heat treatment than L-ascorbic acid, and has a pH of 4 to 6 when the heat treatment temperature is 100 ° C. In the range of .5, and when the heat treatment temperature was 125 ° C., almost no acrylamide was produced in the range of pH 5 to 6.5. Under lower pH conditions, acrylamide was produced at any temperature, but to a lesser extent. The reason why acrylamide is produced from L-ascorbic acid 2-glucoside under a low pH condition is that L-ascorbic acid 2-glucoside is partially hydrolyzed by heat treatment under acidic conditions to produce L-ascorbic acid and D- It is presumed that glucose was produced and acrylamide was produced from the produced L-ascorbic acid and / or D-glucose and L-asparagine. Acrylamide production in this case is also significantly lower in the α, α-trehalose added system than in the non-added system, and it was confirmed that a remarkable production inhibitory effect can be obtained by coexisting α, α-trehalose. . In addition, as is apparent from Table 14, in the case of L-ascorbic acid 2-phosphate, in the heat treatment at 100 ° C., although acrylamide is less produced in the range of pH 4 to 7 than L-ascorbic acid, pH 4 Less than, the production amount of acrylamide equivalent to L-ascorbic acid was shown. In addition, L-ascorbic acid 2-phosphate is less likely to produce acrylamide in the range of pH 4 to 6 in the heat treatment at 125 ° C. compared to L-ascorbic acid. The amount of acrylamide produced was as large as 10 times or more, and the amount of acrylamide produced was the same as that of L-ascorbic acid under the condition where the pH exceeded 6. On the other hand, when this result is compared with the result of L-ascorbic acid 2-glucoside in Table 10, L-ascorbic acid 2-glucoside has a smaller amount of acrylamide generated in a wider pH range and higher heat treatment temperature. It was remarkably superior. Even in the case of L-ascorbic acid 2-phosphate, the production of acrylamide was remarkably suppressed in the α, α-trehalose added system.

<Experiment 13: Effect of coexistence of various phenolic substances on the amount of acrylamide produced from L-asparagine and D-glucose>
The influence of coexistence of various phenolic substances on the production of acrylamide from L-asparagine and D-glucose by heat treatment was investigated. 22 types of phenolic substances shown in Table 15 were added to a 20-ml stoppered test tube in which 0.1 mmol (13.2 mg) of L-asparagine and 0.1 mmol (18.0 mg) of D-glucose had been previously collected. The amount of acrylamide produced was quantified by the same method as in Experiment 1 except that 0.25 mg of any of the above was added and 1 ml of 0.05 M phosphate buffer (pH 6.0) was added thereto. Only L-asparagine and D-glucose were used, and no phenolic substance was added as a control. The results are shown in Table 15. The acrylamide production rate (%) was shown as a relative value when the acrylamide production amount (mg) when only L-asparagine and D-glucose were used was 100%.

  As is apparent from the results in Table 15, depending on the type of phenolic substance, it has been found that coexistence significantly suppresses the production of acrylamide from L-asparagine and D-glucose in the heat treatment. Specifically, among the phenolic substances used in the test, phenolic substances excluding galangin, flavanone, tryptanthrin and coumarin, that is, catechin, epicatechin, epigallocatechin, quercetin, rutin, naringin, hesperidin, kaempferol Cinnamic acid, quinic acid, 3,4-dihydrocinnamic acid, 3-coumaric acid, 4-coumaric acid, p-nitrophenol, curcumin, scopoletin, propyl p-hydroxybenzoate and proanthocyanidins are L-asparagine Alternatively, the acrylamide production rate from L-asparagine and D-glucose is suppressed by coexisting in a molar ratio with respect to D-glucose of 0.004 or more. In particular, rutin, naringin and hesperidin coexist in relatively small amounts, L-asparagine or D-glucose It was confirmed to significantly suppress generation rate acrylamide in the coexistence of about 0.004 in molar ratio (%) to less than 60% against.

<Experiment 14: Effect of coexistence of [alpha], [alpha] -trehalose on acrylamide formation during cooking of french fries>
The effect of coexistence of α, α-trehalose on acrylamide production when actually cooked using food materials was examined using fries as an example.

<Experiment 14-1: Preparation of French fries>
0 g, 0.02 g, 0.06 g, 0.13 g, 0.27 g, 0.53 g of high-purity water-containing crystal α, α-trehalose (registered trademark “Trehha” sold by Hayashibara Corporation) or 30 g of water or 1.3g was added, it processed in the microwave oven for 30 seconds, and it heated and melt | dissolved at about 80 degreeC. Next, 20 g of commercially available dried mashed potato (Miki Foods Co., Ltd., trade name “Queen's Chef Mashed Potato”) was added to each of the obtained liquids and mixed uniformly, and formed into a diameter of 22 mm and a thickness of 3 mm (α, The amount of α-trehalose is 0, 0.1, 0.3, 0.6, 1.2, 2.4 or 6.0% by mass with respect to the dried mashed potato product.) Each obtained molding was fried in cooking oil at 150 ° C. for 4 minutes using an electric fryer (model MACH F3, manufactured by Mach Equipment Co., Ltd.) to prepare french fries. According to the analysis by the present inventors, the dried mashed potato used in this experiment had a moisture content of 7.2% by mass and a saccharide-forming ability of about 8% by mass (D-glucose 3% by mass, D -Fructose 2.8% by mass and sucrose 2.1% by mass).

<Experiment 14-2: Measurement of acrylamide production amount of French fries>
25 g of deionized water was added to 5 g of each of the French fries obtained in Experiment 14-1, and allowed to stand for 10 minutes, and then homogenized for 3 minutes with a homogenizer (model “ULTRA-TU-RRAX”, manufactured by IKA Lab Technics). did. The crushed material was centrifuged at 14,000 rpm for 60 minutes, and the obtained supernatant was frozen at −80 ° C., thawed, and centrifuged again to recover the supernatant. Next, acrylamide-2,3,3, -d3 standard solution (2 ppm) was added to 2 ml of this sample solution as a 0.2 ml internal standard, mixed, and previously conditioned with 5 ml of methanol and 5 ml of deionized water (product) The name “Oasis HBL 500 mg cartridge” (manufactured by Nihon Waters Co., Ltd.) was charged, eluted 10 times with 2 ml of deionized water, and fractionated into a total of 10 fractions. Among these, a fraction containing acrylamide was filtered to obtain a sample for acrylamide analysis. In this experiment, acrylamide was quantified using liquid chromatography-mass spectrometry (LC-MS method) as a measurement method in order to more accurately measure the amount of acrylamide produced in the sample.

LC-MS analysis was performed under the following conditions using a Finigan ion trap type LC / MS / MS system (manufactured by Thermoquest Corporation) as an apparatus.
(LC-MS conditions)
<LC part>
Column; Hydrosphere C18 HS-3C2
(YMC Co., Ltd., inner diameter 2 mm, length 150 mm, particle diameter 5 μm)
Eluent: methanol: water (5:95)
Flow rate; 0.1 ml / ml Column temperature; 40 ° C
Analysis time: 12 minutes Sample injection volume: 20-40 μl
<MS part>
Ionization method: Electrospray (ESI) method Ionization conditions: Sheath gas flow rate 5 (arb), Ox gas flow rate 0 (arb)
Spray voltage 5 (kV), capillary voltage 6 (V)
Capillary temperature 200 ° C,
Tube lens offset voltage 25 (V)
Measurement time: 10 minutes (4 to 7 minutes of LC analysis time is introduced into the ion source)
Detection: Single ion monitoring (SIM)
Acrylamide was measured at m / z 71.5 to 72.6, and internal standard acrylic amide-2,3,3, -d3 was measured at m / z 74.5 to 75.6.

  Each ionization efficiency was determined in advance using acrylamide and a standard product of acrylamide-2,3,3, -d3, which is an internal standard, and the analysis was performed three times per sample, and the peak area of acrylamide detected from the sample was determined. The ratio of the internal standard added to the ratio of the peak areas of acrylamide-2,3,3, -d3 of the internal standard was multiplied. The measured value of these three times was multiplied by the ionization efficiency to obtain a measured value. The test results are shown in Table 13. The amount of acrylamide produced was expressed in ppm per fried potato product.

  As shown in Table 16, the fries prepared without adding α, α-trehalose to dried mashed potato produced 0.71 ppm acrylamide, whereas α, α-trehalose was added to dried mashed potato. As the amount of the french fries prepared in this manner increased, the amount of acrylamide produced decreased, and 0.45 ppm (about 63% compared to the case of no addition) when α, α-trehalose was added at 0.6% by mass. %). In french fries to which α, α-trehalose was added in an amount of 2.4% by mass or more, the amount of acrylamide produced was less than 0.01 ppm, which was less than the detection limit. It has been found that the addition of α, α-trehalose significantly suppresses acrylamide formation during the preparation of french fries. In the case of this experiment, unlike the result of Experiment 4, a relatively small amount of α of 0.6 to 2.4% by mass is obtained with respect to about 8% by mass of sugar having an acrylamide-forming ability contained in the dried mashed potato. , The effect of inhibiting acrylamide formation was significantly recognized by the amount of α-trehalose. This is because the amount of acrylamide produced during the preparation of french fries depends not only on the amount of saccharides having the ability to produce acrylamide contained in the dried mashed potatoes, but also on the amount of organic substances having amino groups. It is presumed that the amount produced is limited.

  As described above, from the results of Experiments 1 to 12, when an edible material containing an organic substance having an amino group and a saccharide capable of producing acrylamide by reacting with this is heated, α, α-trehalose, α , Β-trehalose, reduced palatinose, α-glucosyl α, α-trehalose, α-maltosyl α, α-trehalose, D-mannitol, D-erythritol, and β-cyclodextrin, especially α, α- It has been found that the presence of trehalose or α, β-trehalose can significantly suppress the production of acrylamide. Further, from the results of Experiment 13, it has been found that the production of acrylamide can be remarkably suppressed by the presence of specific phenolic substances, particularly rutin, naringin or hesperidin. Furthermore, from the result of Experiment 14, even when cooking this using actual food material, the amount of acrylamide produced in the cooked food and drink can be significantly reduced by coexisting α, α-trehalose. confirmed.

  Hereinafter, the present invention will be specifically described with reference to examples.

<Potato chips>
The whole potato (Hokkaido, Makein) was washed with water, then peeled off, washed again with water, and then sliced to a thickness of 1.5 mm with a commercial slicer (V Slicer MV-50, manufactured by Shinkosha Co., Ltd.). . After exposing to water and draining, the sliced potato is immersed in an aqueous solution of α, α-trehalose (registered trademark "Treh"), a high-purity hydrous crystal with a concentration of 20% by mass, twice the weight of the sliced potato The α, α-trehalose was infiltrated into the potato by holding at 80 ° C. for 2 hours. Next, the sugar solution was cut, and the potato from which the moisture had been wiped was fried for 2 minutes using an electric fryer (Mach Equipment Co., Ltd., MACHF-3) whose oil temperature was adjusted to 180 ° C. to prepare potato chips. The oil used was an edible mixed oil (edible rapeseed oil and edible soybean oil).

  This product has a good shape and flavor, and since it contains α, α-trehalose, it is a highly safe potato chip in which the production of acrylamide by frying is suppressed, and can be advantageously used as a snack as it is.

<Fries>
After washing the whole potato (Hokkaido, make-in) with water, it is cut into a square pillar-shaped shredded product with a side of about 1 cm by using a shredder, and this is α, α-trehalose containing 0.1% by weight of salt and 20% by weight of salt. (Registered trademark “Trehha” sold by Hayashibara Shoji Co., Ltd.) It was immersed in an aqueous solution and kept at 50 ° C. for 20 minutes. Water was drained, followed by blanching for 3 minutes, and further stored frozen at -20 ° C. This was fried according to a conventional method to prepare french fries.

  This product is good in shape, texture, and flavor, and contains α, β-trehalose, so it is a highly safe fried potato with reduced acrylamide production by frying, Moreover, it can be advantageously used as a side dish.

<Cracker>
A medium seed is prepared by mixing 70 parts by weight of medium flour, 0.25 parts by weight of yeast and 30 parts by weight of water, and then 30 parts by weight of flour, 10 parts by weight of shortening, and D-glucose. 1.5 parts by mass, 1.5 parts by mass of sodium chloride, 0.65 parts by mass of sodium bicarbonate, and 1.5 parts by mass of high-purity water-containing crystal α, α-trehalose (Hayashibara Shoji Co., Ltd., registered trademark “Treha”) I'm going to go home. After forming into a cracker by a conventional method, it was baked in an oven at 180 ° C. for 15 minutes to prepare a soda cracker.

  This product is good in flavor and mouthfeel, and contains α, α-trehalose, so it is a highly safe cracker with suppressed generation of acrylamide by baking. This product can be used as a snack as it is.

<Butter roll>
118 parts by weight of strong powder, 8 parts by weight of sugar, 10 parts by weight of high-purity water-containing crystal α, α-trehalose (Hayashibara Shoji Co., Ltd., registered trademark “Treha”), 1.7 parts by weight of salt, 2 parts by weight of skim milk powder, ocean 2 parts by weight of yeast (manufactured by Sankyo Foods Co., Ltd.), 12 parts by weight of whole egg, 10 parts by weight of unsalted butter, 20 parts by weight of milk, and 75 parts by weight of water are put in a mixer, at 24 ° C., low speed 6 minutes, medium speed 5 After kneading in minutes and temporarily stopping, it was further kneaded for 4.5 minutes at medium speed to create a dough. This was then fermented for 50 minutes as floor time. The dough was divided into 40 g and rounded. After taking a bench time of 20 minutes, fermentation was carried out for 50 minutes in a proofer at 40 ° C. and 80% humidity. After the completion of fermentation, the mixture was baked for 7 minutes in an oven at 230 ° C. and 200 ° C. to prepare a butter roll.

  This product swells plumply, has a good color tone, has a good taste, and contains α, α-trehalose, so it is a highly safe butter roll with suppressed generation of acrylamide by baking.

<Roasted sliced almond>
A commercially available sliced almond (thickness 1 mm) is immersed in an α, β-trehalose (trade name “Neotrehalose” sold by Hayashibara Biochemical Laboratories Co., Ltd.) solution at a concentration of about 50 w / w% at 70 ° C. for 15 minutes. Drained and then roasted at 180 ° C. using an electronic oven to prepare roasted sliced almonds.

  Since this product has a good flavor and contains α, β-trehalose, it is a highly safe roasted slice almond in which the production of acrylamide by roasting is suppressed. This product can be advantageously used as a snack as it is or as various confectionery and bakery ingredients.

<Roasted wheat germ>
After thawing 78 parts by mass of frozen raw wheat germ, 20 parts by mass of hydrated crystal α, α-trehalose (Hayashibara Shoji Co., Ltd., registered trademark “Treha”), Example A-2 of JP-A-7-14376 5 parts by mass of powdered α-glycosyl α, α-trehalose prepared by the method (4.1% α-glucosyl α, α-trehalose in terms of anhydride, 52.5% α-maltosyl α, α-trehalose contained) ) Is mixed with 2 parts by weight of a 5% aqueous solution of Pullulan (Hayashibara Shoji Co., Ltd., trade name “Pullulan PF-20”) prepared in advance, and this is mixed into a sealed extruder. The mixture was heated, kneaded, extruded, granulated, and dried. This was further roasted by a conventional method to prepare roasted wheat germ.

  Since this product has good flavor and contains α, α-trehalose, it is a highly safe roasted wheat germ in which the production of acrylamide by roasting is suppressed. This product is delicious and easy to eat and has excellent storage stability. Moreover, since this product contains abundant minerals such as selenium and zinc, vitamins and dietary fiber, it is suitable as a health food or as a raw material for other foods and drinks.

<Tempura clothes (Tengari)>
After dissolving 20 g of α, α-trehalose (Hayashibara Shoji Co., Ltd., registered trademark “Treha”) in 380 ml of cold water, this was added to a piece of commercially available egg, and then about 230 g of soft flour was sifted. The mixture was lightly mixed to prepare a garment.

  Since this product contains α, α-trehalose, it is a garment that can suppress the formation of acrylamide when used on a natural seed such as meat or vegetable when frying tempura.

<Powdered mashed potato>
100 parts by weight of commercially available dried mashed potato (Miki Foods Co., Ltd., trade name “Queen's Chef Mashed Potato”) and high-purity water-containing crystal α, α-trehalose powder (trade name “Trehha”, Hayashibara Shoji Co., Ltd.) 2.5 mass Part was mixed uniformly to prepare a powdered mashed potato.

  Since this product contains α, α-trehalose, when preparing potato croquettes, etc., it can be used with meat, vegetables, etc., and fried in oil to suppress the formation of acrylamide. It is a composition having a high ability to inhibit acrylamide formation.

<Potato croquette>
Salt and pepper were added to 100 parts by mass of the powdered mashed potato obtained in Example 8, 100 parts by mass of milk and 200 parts by mass of hot water were added, and the mixture was allowed to stand for 10 minutes to return to a plump mashed potato. Next, 100 parts by weight of minced meat and 100 parts by weight of chopped onion were fried in butter, seasoned with salt and pepper, and added to the returned mashed potatoes to form croquettes. According to a conventional method, this was put in the order of flour, eggs and bread crumbs and fried in edible oil at 180 ° C. to prepare potato croquettes. Since this product uses powdered mashed potato containing α, α-trehalose, it is a highly safe potato croquette with suppressed generation of acrylamide during frying.

<Sweet potato snack>
100 parts by weight of wheat flour, 300 parts by weight of grated sweet potato and 30 parts by weight of water are mixed, and 20 parts by weight of high-purity water-containing crystal α, α-trehalose powder (sales of Hayashibara Corporation, registered trademark “Treha”) Then, 0.2 parts by mass of sugar transfer rutin (trade name “αG rutin H”, sold by Hayashibara Shoji Co., Ltd.) was added and mixed, and steamed at 100 ° C. for 10 minutes to obtain a dough. This dough was rolled to a thickness of 1.0 mm, held at 10 ° C. for 12 hours, refrigerated and cured, and cut into a desired shape to obtain a sweet potato snack dough. The dough was then fried in vegetable oil heated to 170 to 180 ° C. to obtain a sweet potato snack. Since this product contains α, α-trehalose and transglycosyl rutin, the production of acrylamide during frying is suppressed, and it is a highly safe sweet potato snack.

<Crisp pretzel>
100 parts by weight of flour, 0.8 parts by weight of baking powder, 1 part by weight of salt, 1.5 parts by weight of high-purity water-containing crystal α, α-trehalose powder (trade name “Trehha”, Hayashibara Shoji Co., Ltd.) To this, 35 parts by mass of milk, 13 parts by mass of salad oil, 12 parts by mass of powdered cheese, and 4.5 parts by mass of chopped parsley were added and kneaded to obtain a dough. The dough was rolled to a thickness of 2 mm and then cut into a width of 5 mm to obtain a pretzel dough. Next, this dough was baked in an oven heated to 230 to 260 ° C. for 6 minutes to prepare a crisp pretzel. Since this product contains α, α-trehalose, it is a highly safe crisp pretzel with suppressed generation of acrylamide upon baking.

<Seasoned instant noodles>
Wheat flour (strong flour) 98.5 parts by mass, high-purity water-containing crystal α, α-trehalose powder (Hayashibara Shoji Co., Ltd., registered trademark “Treha”) 1.5 parts by mass, sugar transfer rutin (Hayashibara Corporation sales, product) Name "αG Rutin H") Add 0.5 parts of 0.5% brackish water to 0.01 parts by weight, knead by a conventional method, prepare a 0.9 mm thick noodle string, and use a steamer for 1 minute 15 seconds It was steamed. Next, 30 parts by weight of bird glass cup was added thereto to absorb the soup, and then fried with salad oil at 145 ° C. for 1 minute 20 seconds to prepare seasoned instant noodles. Since this product contains α, α-trehalose and sugar-transferred rutin, it is a highly safe seasoned instant noodle with suppressed production of acrylamide during frying.

<L-ascorbic acid-containing composition>
1 part by mass of L-ascorbic acid powder and 9 parts by mass of high-purity water-containing crystal α, α-trehalose powder (Hayashibara Shoji Co., Ltd., registered trademark “Treha”) are uniformly mixed, granulated, and L-ascorbic acid A containing composition was obtained.

  Since this product contains α, α-trehalose together with L-ascorbic acid, it is a composition that requires L-ascorbic acids and may react with L-ascorbic acid to produce acrylamide. Even when another composition is produced by heat-treating together with an edible material, it is possible to effectively suppress the formation of acrylamide in the production process. This product is a granule that is free from caking, has good fluidity, is easy to handle and has good storage stability, and contains L-ascorbic acid, and is a high-quality food / drink / cosmetic / pharmaceutical product with high safety. Alternatively, it can be advantageously used to produce various compositions such as intermediate products thereof.

<L-ascorbic acid-containing composition>
1 part by mass of L-ascorbic acid 2-glucoside powder (Hayashibara Biochemical Laboratories Co., Ltd., registered trademark “AA2G”) and high-purity water-containing crystal α, α-trehalose powder (Selling Hayashibara Corporation, registered trademark “Treha”) ) 9 parts by mass was uniformly mixed to obtain a powdered L-ascorbic acid-containing composition.

  Since this product contains α, α-trehalose together with L-ascorbic acid 2-glucoside, it is a composition that requires L-ascorbic acids, and this reacts with L-ascorbic acids to give acrylamide. Even when another composition is produced by heat-treating together with an edible material that may be produced, it is possible to effectively suppress the formation of acrylamide in the production process. This product is a powder having good fluidity, free of caking, easy to handle and having good storage stability, and containing high-safety foods, cosmetics, pharmaceuticals or L-ascorbic acids. It can be advantageously used to produce various compositions such as their intermediate products.

<L-ascorbic acid-containing composition>
1 part by mass of L-ascorbic acid powder, 5 parts by mass of high-purity water-containing crystal α, α-trehalose powder (sales by Hayashibara Corporation, registered trademark “Trehha”) and sugar transfer rutin (sales by Hayashibara Corporation, trade name “αG”) Rutin P]) 0.02 part by mass was uniformly mixed and granulated to obtain an L-ascorbic acid-containing composition.

  Since this product contains α, α-trehalose and transglycosyl rutin together with L-ascorbic acid, it is a composition that requires L-ascorbic acids, and this reacts with L-ascorbic acid to acrylamide. Even in the case where other compositions are produced by heat-treating together with an edible material that may produce acrylamide, production of acrylamide can be effectively suppressed in the production process. This product is a granule that is free from caking, has good fluidity, is easy to handle and has good storage stability, and contains L-ascorbic acid, and is a high-quality food / drink / cosmetic / pharmaceutical product with high safety. Alternatively, it can be advantageously used to produce various compositions such as intermediate products thereof.

<W / O type emollient cream>
The following components were mixed according to the following formulation while being heated and dissolved at 80 ° C.

Beeswax 3.0 parts by weight Cetanol 5.0 parts by weight Reduced lanolin 5.0 parts by weight Squalane 31.5 parts by weight Self-emulsifying glyceryl monostearate 4.0 parts by weight Lipophilic glyceryl monostearate 2.0 parts by weight Sorbitan Monolanophosphate 2.0 parts by weight

The following components were separately mixed according to the following composition, and the mixture was gradually added to a solution dissolved at 80 ° C. while stirring, and cooled to 30 ° C. or less to produce a W / O type emollient cream.

Preservative 0.2 parts by mass L-sodium glutamate 3.2 parts by mass L-serine 0.8 parts by mass α, α-trehalose (trade name “Treha”, sold by Hayashibara Corporation)
2.0 parts by mass α, β-trehalose (trade name “Neotrehalose” sold by Hayashibara Biochemical Laboratories Co., Ltd.) 4.0 parts by mass L-ascorbic acid 2-glucoside (sales by Hayashibara Biochemical Laboratories, Inc.) Registered trademark “AA2G”) 1.0 part by mass propylene glycol 5.0 parts by mass purified water 30.5 parts by mass

  Since this product contains α, α-trehalose and α, β-trehalose together with amino acids and L-ascorbic acid 2-glucoside, it is an emollient cream in which the production of acrylamide by heat treatment is suppressed. In addition, this product exhibits excellent moisture retention, and is good for spreading and gloss, and is suitable as a highly safe cosmetic.

<Drink agent>
As an amino acid mixture, L-isoleucine 4 parts by mass, L-leucine 6 parts by mass, L-lysine hydrochloride 8 parts by mass, L-phenylalanine 8 parts by mass, L-tyrosine 1 part by mass, L-tryptophan 8 parts by mass, L-valine A mixture of 8 parts by mass, 1 part by mass of L-aspartic acid, 1 part by mass of L-serine, 1 part by mass of L-methionine, 2 parts by mass of L-threonine, and 8 parts by mass of L-arginine hydrochloride was prepared. Subsequently, 4 parts by mass of this amino acid mixture, 1 part by mass of L-ascorbic acid 2-glucoside powder (trade name “AA2G”, sold by Hayashibara Biochemical Co., Ltd.), high-purity water-containing crystal α, α-trehalose powder (Co., Ltd.) Hayashibara Shoji, registered trademark "Treha") 6 parts by mass, α, β-trehalose (Hayashibara Biochemical Laboratories Co., Ltd., trade name "Neotrehalose") 2 parts by weight, sugar transfer hesperidin (Hayashibara Corporation sales) , Trade name "αG Hesperidin PA") 0.02 parts by mass, thiamine nitrate 0.01 parts by mass, nicotinamide 0.04 parts by mass and water 86.05 parts by mass uniformly mixed into a 50 ml brown bottle After filling, it was sealed, and this was kept at 85 ° C. for 30 minutes and sterilized by heating to prepare a drink.

  Since this product contains α, α-trehalose and α, β-trehalose together with amino acid and L-ascorbic acid 2-glucoside, it is a highly safe amino acid-containing drink with suppressed generation of acrylamide by heat treatment. It is suitable as.

  By applying the method for inhibiting acrylamide production of the present invention to the production of various compositions such as foods, cosmetics, pharmaceuticals, or intermediate products thereof, a highly safe composition that is less likely to cause carcinogenesis and neuropathy. Can be manufactured. In addition, the composition having an acrylamide production inhibitory ability comprising the organic substance having an amino group and / or a saccharide having an acrylamide production ability and an organic substance having an acrylamide production inhibitory ability of the present invention is an agricultural product, As livestock products, marine products or processed products thereof, seasonings, sweeteners, etc., they can be advantageously used in foods, drinks, cosmetics, pharmaceuticals and intermediate products thereof. In particular, when the saccharide having acrylamide-forming ability is L-ascorbic acid, it is a composition that requires L-ascorbic acid as an L-ascorbic acid-containing composition having acrylamide production-inhibiting ability, By using this for the production of foods, beverages, cosmetics, pharmaceuticals, or intermediate products containing other ingredients that may generate acrylamide by heat treatment, it is effective to produce acrylamide in those manufacturing processes. Can be suppressed. The L-ascorbic acid-containing composition is high in safety and is used to produce various compositions such as high-quality foods, cosmetics, pharmaceuticals, or intermediate products thereof with enhanced L-ascorbic acid (vitamin C). Can be advantageously used.

  As described above, the present invention is an invention that exhibits remarkable effects, and contributes greatly to industries that produce or use foods, drinks, cosmetics, pharmaceuticals, or intermediate products thereof. .

Claims (1)

In heating an amino acid with L -ascorbic acid , or an L-ascorbic acid derivative selected from L-ascorbic acid 2-glucoside, L-ascorbic acid 2-phosphate, or a salt thereof , α, α-trehalose or α, A method for inhibiting acrylamide production, wherein β-trehalose is allowed to coexist with L -ascorbic acid or an L-ascorbic acid derivative in a molar ratio of 1 or more.