WO2021100678A1 - Plant extract containing 2-acetyl-1-pyrroline - Google Patents
Plant extract containing 2-acetyl-1-pyrroline Download PDFInfo
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- WO2021100678A1 WO2021100678A1 PCT/JP2020/042701 JP2020042701W WO2021100678A1 WO 2021100678 A1 WO2021100678 A1 WO 2021100678A1 JP 2020042701 W JP2020042701 W JP 2020042701W WO 2021100678 A1 WO2021100678 A1 WO 2021100678A1
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- Prior art keywords
- acetyl
- pyrrolin
- plant
- pyrroline
- ppm
- Prior art date
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
- A23L2/52—Adding ingredients
- A23L2/56—Flavouring or bittering agents
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L23/00—Soups; Sauces; Preparation or treatment thereof
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/20—Synthetic spices, flavouring agents or condiments
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/20—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
Definitions
- the present invention relates to a plant extract containing 2-acetyl-1-pyrrolin and a method for producing the same.
- the present invention also relates to compositions containing 2-acetyl-1-pyrrolin and certain cooking oils.
- the present invention further relates to the plant extract or a fragrance composition containing the composition, and various products containing the fragrance composition.
- the present invention also relates to a method for stabilizing 2-acetyl-1-pyrrolin.
- 2-Acetyl-1-pyrrolin is known as an aroma component contained in the aroma of grains such as rice or cooked meat (J. Agric. Food Chem., 1993, 41, 1458-1461, Non-Patent Document 1). .. Since this compound has a very characteristic popcorn-like scent and a very low threshold value, it is attracting attention as a perfume material used in foods and the like.
- 2-acetyl-1-pyrroline is a very unstable compound and is known to be colored due to polymerization by polymerization (J. Agric. Food Chem., 1983, 31, 823-). 826, Non-Patent Document 2).
- Patent Document 1 Japanese Patent Application Laid-Open No. 2007-153785
- Patent Document 2 a method of obtaining 2-acetyl-1-pyrroline as a diluted solution by azeotropic distillation with ethanol or another solvent at the time of purification can be industrialized. It has been reported that 2-acetyl-1-pyrrolin can be obtained in a stable state. Further, in Japanese Patent Application Laid-Open No.
- Patent Document 2 when purifying 2-acetyl-1-pyrrolin by vacuum distillation, the solvent and the receiver containing the solvent are cooled, and the receiver is charged with 2 It has been reported that by distilling -acetyl-1-pyrrolin, not only an azeotropic solvent but also a high boiling point solvent can be used as a diluting solvent.
- a method for producing a plant extract containing 2-acetyl-1-pyrrolin comprising an extraction step of extracting a plant material containing 2-acetyl-1-pyrrolin with one or two edible oils selected from the group consisting of triesters (MCTs) of medium chain fatty acids and glycerin and triacetin. How to make an extract.
- MCTs triesters
- the production method according to [1] which comprises a pretreatment step of treating the plant raw material by steam distillation, water extraction or hot water extraction before the extraction step.
- the production method according to [1] or [2] which comprises a post-treatment step of dehydrating and filtering the extract obtained in the extraction step.
- the fragrance composition according to [8] which contains 1 ppb to 1000 ppm of 2-acetyl-1-pyrrolin.
- 2-Acetyl-1-pyrroline comprises mixing 2-acetyl-1-pyrrolin with one or two edible oils selected from the group consisting of triesters (MCTs) of medium chain fatty acids and glycerin and triacetin. -1-Method for stabilizing pyrolin.
- MCTs triesters
- -1-Method for stabilizing pyrolin [12] The stability according to [11], wherein the residual rate of 2-acetyl-1-pyrrolin is 60% or more when 2-acetyl-1-pyrrolin having a concentration of 10 ppm is stored in a dark place at 30 ° C. for 2 months. How to make it.
- 2-acetyl-1-pyrrolin when combined with a specific cooking oil, 2-acetyl-1-pyrrolin can be stably present, thereby sustaining the characteristic aroma of 2-acetyl-1-pyrrolin. Therefore, it can be suitably used as a fragrance material used in various products. According to one aspect of the present invention, by extracting 2-acetyl-1-pyrrolin from a plant, not only 2-acetyl-1-pyrrolin can be obtained on an industrial scale by a simple and safe method, but also natural. It is possible to provide a fragrance material with a rich sense.
- a method for producing a plant extract containing 2-acetyl-1-pyrrolin which is one aspect of the present invention, will be described.
- a plant raw material containing 2-acetyl-1-pyrrolin is composed of a triester (MCT) of a medium-chain fatty acid and glycerin and triacetin. It is characterized by including an extraction step of extracting with one or two selected edible oils.
- the method for producing a plant extract of the present invention extracts 2-acetyl-1-pyrrolin from a plant raw material, it is excellent in safety and 2-acetyl-1 without going through a complicated purification step.
- -Pyrrolin can be obtained on an industrial scale.
- one or two kinds of edible oils selected from the group consisting of triester (MCT) of medium chain fatty acid and glycerin and triacetin are used as an extraction solvent.
- MCT triester
- 2-Acetyl-1-pyrrolin can be stably present in the obtained plant extract for a long period of time, and the characteristic aroma of 2-acetyl-1-pyrrolin can be maintained.
- a plant material containing 2-acetyl-1-pyrrolin is extracted with one or two edible oils selected from the group consisting of triesters (MCTs) of medium-chain fatty acids and glycerin and triacetin.
- MCTs triesters
- the plant raw material is not particularly limited as long as it contains 2-acetyl-1-pyrrolin.
- Examples of such plant raw materials include one or more selected from the group consisting of pandan leaf, dadacha beans, aromatic rice and corn.
- pandan leaf is preferable because it contains a large amount of 2-acetyl-1-pyrrolin.
- the extraction solvent one or two kinds of edible oils selected from the group consisting of triester (MCT) of medium-chain fatty acid and glycerin and triacetin are used. These cooking oils have the effect of retaining 2-acetyl-1-pyrrolin in a stable state. In the present invention, by using these cooking oils as an extraction solvent, 2-acetyl-1-pyrrolin can be stably present in the obtained plant extract as it is.
- MCT examples include a triester of a medium-chain fatty acid having 5 to 12 carbon atoms, preferably 6 to 10 carbon atoms and glycerin.
- the ratio of cooking oil to plant raw materials is preferably 1: 1 to 1:30, more preferably 1: 2 to 1:15, and even more preferably 1: 3 to 1:10.
- the extraction method is not particularly limited, and 2-acetyl-1-pyrrolin can be obtained from the plant material by bringing the plant material into contact with the plant material by immersing the plant material in the cooking oil which is the extraction solvent or by heating and refluxing. Extract.
- the plant material may be pulverized in advance.
- a plant material may be used as a substrate for fermentation treatment with bacteria, fungi, or the like.
- the extraction temperature may be any of heating, room temperature and cooling conditions, but is not particularly limited, but from the viewpoint of extraction efficiency, 10 to 100 ° C. is preferable, 25 to 90 ° C. is more preferable, and 30 ° C. -70 ° C is more preferable.
- the extraction time may be determined in consideration of the extraction efficiency and is not particularly limited, but is usually preferably 0.5 to 72 hours, more preferably 1 to 24 hours, still more preferably 1 to 12 hours from the viewpoint of stability. ..
- the extraction pressure may be normal pressure, reduced pressure, or pressurized, and is not particularly limited, but usually, normal pressure is preferable from the viewpoint of stability.
- the same plant material may be extracted multiple times. Further, different plant raw materials may be extracted a plurality of times with the extraction solvent from which the plant raw materials are extracted for the purpose of increasing the concentration of 2-acetyl-1-pyrrolin in the plant extract.
- the extract can be separated to obtain a plant extract by any method such as cooling, standing or centrifuging.
- a pretreatment step of treating the plant raw material by steam distillation, water extraction or warm water extraction may be performed before the extraction step.
- Conditions such as temperature, time and pressure may be appropriately determined by those skilled in the art depending on the treatment method.
- the temperature of water is preferably 10 to 30 ° C.
- the temperature of water is preferably 30 to 60 ° C.
- the pH value of water or hot water may be adjusted to the range of 5-9 with a buffer such as phosphate buffer from the viewpoint of stability. preferable.
- the pretreatment extract can be separated by any method such as cooling, standing or centrifuging.
- the extraction step is performed by bringing the pretreatment extract into contact with cooking oil.
- the plant extract containing 2-acetyl-1-pyrrolin obtained in the extraction step can be used as it is as a fragrance material, but it is preferable to carry out a post-treatment step of dehydration and filtration.
- a post-treatment step of dehydration and filtration By performing the post-treatment step, the solid matter unnecessary for the solvent can be removed, the water content can be removed, and the stability of 2-acetyl-1-pyrrolin can be further enhanced.
- Plant extract containing 2-acetyl-1-pyrrolin can be obtained by the method for producing a plant extract of the present invention.
- the obtained plant extract may be used as it is as a perfume material, or if necessary, one or two edible species selected from the group consisting of triester (MCT) of medium-chain fatty acid and glycerin and triacetin. It may be diluted with oil and used as a fragrance material.
- the cooking oil used as the diluent may be the same as or different from the extraction solvent.
- the content (mass basis) of 2-acetyl-1-pyrrolin is preferably 1 ppb to 1000 ppm, more preferably 0.1 to 500 ppm, still more preferably 10 to 100 ppm.
- the plant extract of the present invention is rich in natural feeling and can be suitably used as a fragrance material for various products, especially beverages, foods, pharmaceuticals, quasi-drugs, tobacco, cosmetics, oral care products and feeds. it can. Further, in the plant extract of the present invention, one or two kinds of edible oil selected from the group consisting of triester (MCT) of medium-chain fatty acid and glycerin and triacetin are used as the extraction solvent, and the edible oil is used as a carrier as it is. Since 2-acetyl-1-pyrrolin is retained as a substance, 2-acetyl-1-pyrrolin can be stably present.
- MCT triester
- the residual rate of 2-acetyl-1-pyrroline is 60% when 2-acetyl-1-pyrroline at a concentration (mass basis) of 10 ppm is stored for 2 months in a dark place at 30 ° C.
- 70% or more is more preferable, and 80% or more is further preferable.
- the residual rate (%) of 2-acetyl-1-pyrrolin can be calculated by the following formula. (Concentration of 2-acetyl-1-pyrrolin when stored in a dark place at 30 ° C. for 2 months ppm) / (Concentration of 2-acetyl-1-pyrrolin at the start of stability test 10 ppm) ⁇ 100 (%)
- composition of the present invention consists of 2-acetyl-1-pyrrolin, a triester (MCT) of a medium-chain fatty acid and glycerin, and triacetin. It is characterized by containing one or two selected edible oils.
- 2-Acetyl-1-pyrrolin may be extracted from a plant material containing 2-acetyl-1-pyrrolin, or may be obtained by synthesis.
- 2-acetyl-1-pyrrolin is dissolved or dispersed in one or two edible oils selected from the group consisting of triesters (MCTs) of medium-chain fatty acids and glycerin and triacetin.
- the residual rate of 2-acetyl-1-pyrrolin when 2-acetyl-1-pyrrolin at a concentration of 10 ppm is stored for 2 months in a dark place at 30 ° C. is 60% or more. 70% or more is more preferable, and 80% or more is further preferable.
- the fragrance composition of the present invention is characterized by containing the plant extract or the composition.
- the content (mass basis) of 2-acetyl-1-pyrrolin is appropriately determined according to the intended use and purpose, and is not particularly limited, but is usually 0.01 ppb to 1000 ppm. It is preferably 0.1 ppb to 10 ppm, more preferably 1 ppb to 100 ppb.
- the fragrance composition of the present invention may contain various additives.
- Additives are not particularly limited, and examples thereof include antioxidants, preservatives, antibacterial agents, pH adjusters, diluents, carriers, and other additives. These additives may be used alone or in combination of two or more.
- Antioxidants include butylhydroxytoluene, butylhydroxyanisole, citric acid, glutathione, selenium, lycopene, vitamin A, vitamin E, vitamin C, etc., pyrolopyrrole derivatives, and free radicals obtained from extracts from various plants. Examples thereof include enzymes having antioxidant properties such as scavengers (free radicals), superoxide dismutase and glutathione peroxidase.
- Preservatives or antibacterial agents include benzoic acid, sodium benzoate, isopropyl paraoxybenzoate, isobutyl paraoxybenzoate, ethyl paraoxybenzoate, methyl paraoxybenzoate, butyl paraoxybenzoate, propyl paraoxybenzoate, sodium hyposulfate, hyposulfate.
- pH adjuster examples include adipic acid, citric acid, trisodium citrate, gluconodeltalactone, gluconic acid, potassium gluconate, sodium gluconate, DL-tartaric acid, L-tartaric acid, DL-potassium hydrogen tartrate, and L.
- -Potataric acid hydrogen DL-Sodium tartarate, L-Sodium tartarate, potassium carbonate (anhydrous), sodium hydrogen carbonate, sodium carbonate, carbon dioxide, lactic acid, sodium lactate, glacial acetic acid, disodium dihydrogen pyrophosphate, fumaric acid, fumal Examples thereof include monosodium acid, DL-tartaric acid, DL-sodium malate, phosphoric acid, dipotassium hydrogen phosphate, potassium dihydrogen phosphate, disodium hydrogen phosphate, and sodium dihydrogen phosphate.
- the diluent or carrier is not particularly limited as long as it does not interfere with the effects of the present invention.
- sugars such as sucrose, glucose, dextrin, starches, cyclodextrin, trehalose, lactose, maltose, palatinose, xylose, candy, liquid sugar;
- Alcohols such as ethanol, propylene glycol and glycerin;
- Sugar alcohols such as reduced starch syrup, reduced maltose starch syrup, sorbitol, lactitol, palatinit, mannitol, xylitol, erythritol, maltitol;
- examples thereof include polysaccharides such as gum arabic, xanthan gum, carrageenan, guar gum and gellan gum.
- additives include chelating agents, fragrances, spice extracts, edible plant extracts, fruit extracts, cold pressed oil low boiling fractions, known antioxidants (eg BHT, BHA, ⁇ -tocopherols, vitamins).
- Preservatives eg, sorbic acid, benzoic acid, shirako protein extract
- shelf life improvers eg, sodium acetate, glycine, glycerin fatty acid ester, lysozyme, chitosan
- the perfume composition of the present invention can be blended or aromatized in beverages, foods, pharmaceuticals, quasi-drugs, tobacco, cosmetics, oral care products, feeds and the like.
- Beverages include, for example, carbonated beverages, fruit beverages, fruit-free beverages, vegetable beverages, favorite beverages, alcoholic beverages, non-alcoholic beverages, tea beverages, herbal teas, coffee beverages, functional beverages, sugarless beverages, sports beverages, nutrition. ⁇ Nourishing drinks, dairy products, dairy products, lactic acid bacteria beverages, yogurt beverages, dairy beverages, soups, various instant beverages, etc.
- Foods include, for example, cold confectionery, Japanese confectionery, Western confectionery, desserts, ice cream, sherbet, baked confectionery, bakery, candy, chewing gum, tablets, gummy, oil and fat products, margarine, coffee whitener, cheese food, dressing.
- Pharmaceuticals include medicated cosmetics, medicated lotions, tablets, liquid medicines, capsule-type medicines, granular medicines, and the like.
- quasi-drugs examples include supplements, medicated cosmetics, medicated bath salts, and repellents.
- cigarettes examples include heat-not-burn tobacco, cigarettes, cigarettes, smokeless tobacco, pipes, xel, water tobacco, and electronic cigarettes.
- cosmetics include fragrance products, basic cosmetics, hair cosmetics, finishing cosmetics, toiletry products, bathing agents, body care products, hair care products, cleaning agents, kitchen detergents, soaps, soft finishing agents, and air fresheners.
- Oral care products include mouthwashes, toothpastes, toothpastes, liquid toothpastes, oral care gums, oral care candy, and mouth sprays.
- feed examples include livestock feed, fish feed, pet feed, and the like.
- the content (mass basis) of 2-acetyl-1-pyrrolin in various products may be appropriately determined according to the purpose and application, and is not particularly limited, but is usually preferably in the range of 0.02 ppt to 20 ppb, and 0.
- the range of 2 ppt to 2 ppt is more preferable, and the range of 2 ppt to 200 ppt is even more preferable. It is preferable to blend or perfume the perfume composition of the present invention in an amount such that the content of 2-acetyl-1-pyrrolin in various products falls within the above range.
- 2-acetyl-1-pyrrolin is a very unstable compound, it is selected from the group consisting of triester (MCT) of medium-chain fatty acid and glycerin and triacetin.
- MCT triester
- 2-Acetyl-1-pyrrolin can be stabilized by mixing with one or two edible oils. That is, the present invention comprises mixing 2-acetyl-1-pyrrolin with one or two edible oils selected from the group consisting of triesters (MCTs) of medium chain fatty acids and glycerin and triacetin. It also includes methods for stabilizing 2-acetyl-1-pyrrolin. According to the method of the present invention, 2-acetyl-1-pyrrolin can be stably present for a long period of time.
- the residual rate of 2-acetyl-1-pyrroline is 60% when 2-acetyl-1-pyrroline at a concentration (mass basis) of 10 ppm is stored for 2 months in a dark place at 30 ° C. As mentioned above, it is more preferably 70% or more, still more preferably 80% or more.
- the residual rate of 2-acetyl-1-pyrrolin when 2-acetyl-1-pyrrolin at a concentration (mass basis) of 1 ppm is stored for 2 months in a dark place at 30 ° C. is 60%. As mentioned above, it is more preferably 70% or more, still more preferably 80% or more.
- the residual rate of 2-acetyl-1-pyrrolin when 2-acetyl-1-pyrrolin at a concentration (mass basis) of 100 ppm is stored for 2 months in a dark place at 30 ° C. It is 60% or more, more preferably 70% or more, still more preferably 80% or more.
- Example 1 10 g of Pandan leaf (commercially available) was used as a plant raw material, and 50 g of a phosphate buffer solution having a pH of 7 was added. After stirring at room temperature for 1 hour, MCT (tri (caprylic capric acid) glyceryl, MCT with a carbon number of C6: C8 ratio of 6: 4) was added as edible oil, and extraction was performed while stirring at room temperature for 30 minutes. It was. The obtained oil layer was used as a plant extract, and it was confirmed by gas chromatography that 2-acetyl-1-pyrrolin was contained.
- MCT tri (caprylic capric acid) glyceryl, MCT with a carbon number of C6: C8 ratio of 6: 4
- Test Example 1 (Sensory evaluation) 0.1 g of shrimp flavor and 100 g of powdered soup were mixed, 100 mL of boiling water was added and mixed well to prepare a bisque of shrimp, and comparison and evaluation were performed with and without addition of the plant extract obtained in Example 1. .. A panel of 8 people each performed a sensory evaluation.
- Each panel evaluated the four items shown in Table 3, and compared "blank products” and “Example 1 plant extract additive products”, and added 1 point to those with superiority and 0 points to those without. .. The following is the total score of the panel of 8 people.
- Example 1 It was found that the plant extract additive has a strong overall titer and has an effect of increasing the thickness of the taste. It was also found that it gives a scent reminiscent of the body of shrimp.
- the 2-acetyl-1-pyrrolin concentration (mass basis) at the start of the storage stability test was 1 ppm or 10 ppm.
- the residual rates of 2-acetyl-1-pyrrolin are shown in Tables 5 and 6 below, respectively.
- the stability of 2-acetyl-1-pyrrolin in an alcohol solvent depends on the concentration of 2-acetyl-1-pyrrolin, and the storage stability when the concentration of 2-acetyl-1-pyrrolin is 100 ppm. Was found to decrease. Since the alcohol solvent is easily mixed with water, it cannot be dehydrated when it contains water. From the results of Test Example 2, it has been found that the stability of 2-acetyl-1-pyrrolin decreases when it contains water. Therefore, the stability of 2-acetyl-1-pyrrolin when stored for a long period of time. Is expected to decline further. In addition, since the alcohol solvent does not separate from water, it is not possible to extract the solvent from the distillate after steam distillation or the water extract of the plant. Even when the pretreatment step of treating the plant raw material by steam distillation, water extraction or warm water extraction is performed before the extraction step, edible oils such as MCT can be extracted from the aqueous solution which is the pretreatment liquid. It is considered to have an advantage.
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Abstract
The present invention relates to a method in which, in order to use 2-acetyl-1-pyrroline as a perfume material, 2-acetyl-1-pyrroline is stabilized for a long time, thereby enabling the characteristic fragrance of 2-acetyl-1-pyrroline to last. According to the present invention, 2-acetyl-1-pyrroline is used in combination with one or two edible oils selected from the group consisting of triesters (MCTs) of medium-chain fatty acids and glycerin and triacetin to stabilize 2-acetyl-1-pyrroline, thereby enabling the characteristic fragrance of 2-acetyl-1-pyrroline to last. Accordingly, the present invention can be suitably used as a perfume material for a variety of products.
Description
本発明は、２－アセチル－１－ピロリンを含む植物抽出物およびその製造方法に関する。また、本発明は、２－アセチル－１－ピロリンおよび特定の食用油を含む組成物に関する。本発明はさらに、前記植物抽出物または前記組成物を含む香料組成物、ならびに前記香料組成物を含む各種製品に関する。また、本発明は、２－アセチル－１－ピロリンの安定化方法に関する。
The present invention relates to a plant extract containing 2-acetyl-1-pyrrolin and a method for producing the same. The present invention also relates to compositions containing 2-acetyl-1-pyrrolin and certain cooking oils. The present invention further relates to the plant extract or a fragrance composition containing the composition, and various products containing the fragrance composition. The present invention also relates to a method for stabilizing 2-acetyl-1-pyrrolin.
２－アセチル－１－ピロリンは米などの穀物あるいは調理肉の香気中に含まれる香気成分として知られている（J. Agric. Food Chem., 1993, 41, 1458-1461、非特許文献１）。この化合物は、ポップコーン様の極めて特徴的な香りと非常に低い閾値を持っていることから、食品などに用いられる香料素材として注目されている。
一方、２－アセチル－１－ピロリンは非常に不安定な化合物であり、重合によるポリマー化等が原因で着色することが知られている（J. Agric. Food Chem., 1983, 31, 823-826、非特許文献２）。そのため、２－アセチル－１－ピロリンの合成方法は現在までに多く報告されているが、工業化が可能な規模での合成方法の報告は少ない。
例えば、特開２００７－１５３７８５号公報（特許文献１）では、精製時にエタノールまたはその他の溶媒と共沸蒸留することにより、２－アセチル－１－ピロリンを希釈溶液として得る方法が工業化可能であり、安定な状態で２－アセチル－１－ピロリンを得られることが報告されている。
また、特開２０１４－７３９９９号公報（特許文献２）では、２－アセチル－１－ピロリンを減圧蒸留により精製する際に、溶媒および該溶媒を入れた受器を冷却し、その受器に２－アセチル－１－ピロリンを留出させることで、共沸可能な溶媒に限られず、高沸点溶媒も希釈溶媒として使用できることが報告されている。 2-Acetyl-1-pyrrolin is known as an aroma component contained in the aroma of grains such as rice or cooked meat (J. Agric. Food Chem., 1993, 41, 1458-1461, Non-Patent Document 1). .. Since this compound has a very characteristic popcorn-like scent and a very low threshold value, it is attracting attention as a perfume material used in foods and the like.
On the other hand, 2-acetyl-1-pyrroline is a very unstable compound and is known to be colored due to polymerization by polymerization (J. Agric. Food Chem., 1983, 31, 823-). 826, Non-Patent Document 2). Therefore, many methods for synthesizing 2-acetyl-1-pyrrolin have been reported so far, but there are few reports on methods for synthesizing 2-acetyl-1-pyrrolin on a scale that can be industrialized.
For example, in Japanese Patent Application Laid-Open No. 2007-153785 (Patent Document 1), a method of obtaining 2-acetyl-1-pyrroline as a diluted solution by azeotropic distillation with ethanol or another solvent at the time of purification can be industrialized. It has been reported that 2-acetyl-1-pyrrolin can be obtained in a stable state.
Further, in Japanese Patent Application Laid-Open No. 2014-73999 (Patent Document 2), when purifying 2-acetyl-1-pyrrolin by vacuum distillation, the solvent and the receiver containing the solvent are cooled, and the receiver is charged with 2 It has been reported that by distilling -acetyl-1-pyrrolin, not only an azeotropic solvent but also a high boiling point solvent can be used as a diluting solvent.
一方、２－アセチル－１－ピロリンは非常に不安定な化合物であり、重合によるポリマー化等が原因で着色することが知られている（J. Agric. Food Chem., 1983, 31, 823-826、非特許文献２）。そのため、２－アセチル－１－ピロリンの合成方法は現在までに多く報告されているが、工業化が可能な規模での合成方法の報告は少ない。
例えば、特開２００７－１５３７８５号公報（特許文献１）では、精製時にエタノールまたはその他の溶媒と共沸蒸留することにより、２－アセチル－１－ピロリンを希釈溶液として得る方法が工業化可能であり、安定な状態で２－アセチル－１－ピロリンを得られることが報告されている。
また、特開２０１４－７３９９９号公報（特許文献２）では、２－アセチル－１－ピロリンを減圧蒸留により精製する際に、溶媒および該溶媒を入れた受器を冷却し、その受器に２－アセチル－１－ピロリンを留出させることで、共沸可能な溶媒に限られず、高沸点溶媒も希釈溶媒として使用できることが報告されている。 2-Acetyl-1-pyrrolin is known as an aroma component contained in the aroma of grains such as rice or cooked meat (J. Agric. Food Chem., 1993, 41, 1458-1461, Non-Patent Document 1). .. Since this compound has a very characteristic popcorn-like scent and a very low threshold value, it is attracting attention as a perfume material used in foods and the like.
On the other hand, 2-acetyl-1-pyrroline is a very unstable compound and is known to be colored due to polymerization by polymerization (J. Agric. Food Chem., 1983, 31, 823-). 826, Non-Patent Document 2). Therefore, many methods for synthesizing 2-acetyl-1-pyrrolin have been reported so far, but there are few reports on methods for synthesizing 2-acetyl-1-pyrrolin on a scale that can be industrialized.
For example, in Japanese Patent Application Laid-Open No. 2007-153785 (Patent Document 1), a method of obtaining 2-acetyl-1-pyrroline as a diluted solution by azeotropic distillation with ethanol or another solvent at the time of purification can be industrialized. It has been reported that 2-acetyl-1-pyrrolin can be obtained in a stable state.
Further, in Japanese Patent Application Laid-Open No. 2014-73999 (Patent Document 2), when purifying 2-acetyl-1-pyrrolin by vacuum distillation, the solvent and the receiver containing the solvent are cooled, and the receiver is charged with 2 It has been reported that by distilling -acetyl-1-pyrrolin, not only an azeotropic solvent but also a high boiling point solvent can be used as a diluting solvent.
しかしながら、２－アセチル－１－ピロリンを長期間安定化させる方法は知られておらず、２－アセチル－１－ピロリンを香料素材として利用するためには依然として課題があった。
このような状況の下、工業的規模で２－アセチル－１－ピロリンが得られるだけでなく、得られた２－アセチル－１－ピロリンを長期間安定に存在させ、２－アセチル－１－ピロリンの特徴的な香りを持続させる方法を提供することが望ましい。 However, a method for stabilizing 2-acetyl-1-pyrrolin for a long period of time has not been known, and there are still problems in using 2-acetyl-1-pyrrolin as a fragrance material.
Under such circumstances, not only 2-acetyl-1-pyrrolin can be obtained on an industrial scale, but also the obtained 2-acetyl-1-pyrrolin can be stably present for a long period of time, and 2-acetyl-1-pyrrolin can be obtained. It is desirable to provide a method of sustaining the characteristic scent of.
このような状況の下、工業的規模で２－アセチル－１－ピロリンが得られるだけでなく、得られた２－アセチル－１－ピロリンを長期間安定に存在させ、２－アセチル－１－ピロリンの特徴的な香りを持続させる方法を提供することが望ましい。 However, a method for stabilizing 2-acetyl-1-pyrrolin for a long period of time has not been known, and there are still problems in using 2-acetyl-1-pyrrolin as a fragrance material.
Under such circumstances, not only 2-acetyl-1-pyrrolin can be obtained on an industrial scale, but also the obtained 2-acetyl-1-pyrrolin can be stably present for a long period of time, and 2-acetyl-1-pyrrolin can be obtained. It is desirable to provide a method of sustaining the characteristic scent of.
本発明は、以下に示したとおりのものである。
［１］２－アセチル－１－ピロリンを含む植物抽出物の製造方法であって、
２－アセチル－１－ピロリンを含む植物原料を中鎖脂肪酸とグリセリンとのトリエステル（ＭＣＴ）およびトリアセチンからなる群より選ばれる１種または２種の食用油で抽出する抽出工程を含む、前記植物抽出物の製造方法。
［２］前記抽出工程の前に、水蒸気蒸留、水抽出または温水抽出によって前記植物原料を処理する前処理工程を含む、［１］に記載の製造方法。
［３］前記抽出工程で得られた抽出物を脱水および濾過する後処理工程を含む、［１］または［２］に記載の製造方法。
［４］前記植物原料が、パンダンリーフ、ダダチャ豆、香り米およびトウモロコシからなる群より選ばれる１種以上である、［１］から［３］のいずれか一項に記載の製造方法。
［５］［１］から［４］のいずれか一項に記載の製造方法で製造された植物抽出物であって、２－アセチル－１－ピロリンを１ｐｐｂ～１０００ｐｐｍ含む、植物抽出物。
［６］３０℃暗所で、濃度１０ｐｐｍの２－アセチル－１－ピロリンを２ヶ月間保存したときの２－アセチル－１－ピロリンの残存率が６０％以上である、［５］に記載の植物抽出物。
［７］２－アセチル－１－ピロリン、および
中鎖脂肪酸とグリセリンとのトリエステル（ＭＣＴ）およびトリアセチンからなる群より選ばれる１種または２種の食用油
を含む組成物。
［８］［５］または［６］に記載の植物抽出物、または［７］に記載の組成物を含む香料組成物。
［９］２－アセチル－１－ピロリンを１ｐｐｂ～１０００ｐｐｍ含む、［８］に記載の香料組成物。
［１０］［８］または［９］に記載の香料組成物を含む、飲料、食品、医薬品、医薬部外品、たばこ、香粧品、オーラルケア製品および飼料からなる群より選ばれる製品。
［１１］２－アセチル－１－ピロリンを、中鎖脂肪酸とグリセリンとのトリエステル（ＭＣＴ）およびトリアセチンからなる群より選ばれる１種または２種の食用油と混合することを含む、２－アセチル－１－ピロリンの安定化方法。
［１２］３０℃暗所で濃度１０ｐｐｍの２－アセチル－１－ピロリンを２ヶ月間保存したときの２－アセチル－１－ピロリンの残存率が６０％以上である、［１１］に記載の安定化方法。 The present invention is as shown below.
[1] A method for producing a plant extract containing 2-acetyl-1-pyrrolin.
The plant comprising an extraction step of extracting a plant material containing 2-acetyl-1-pyrrolin with one or two edible oils selected from the group consisting of triesters (MCTs) of medium chain fatty acids and glycerin and triacetin. How to make an extract.
[2] The production method according to [1], which comprises a pretreatment step of treating the plant raw material by steam distillation, water extraction or hot water extraction before the extraction step.
[3] The production method according to [1] or [2], which comprises a post-treatment step of dehydrating and filtering the extract obtained in the extraction step.
[4] The production method according to any one of [1] to [3], wherein the plant raw material is at least one selected from the group consisting of pandan leaf, dadacha beans, aromatic rice and corn.
[5] A plant extract produced by the production method according to any one of [1] to [4], which contains 1 ppb to 1000 ppm of 2-acetyl-1-pyrrolin.
[6] The remaining rate of 2-acetyl-1-pyrrolin when 2-acetyl-1-pyrrolin at a concentration of 10 ppm is stored for 2 months in a dark place at 30 ° C. is 60% or more, according to [5]. Plant extract.
[7] A composition containing one or two edible oils selected from the group consisting of 2-acetyl-1-pyrroline, a triester (MCT) of a medium-chain fatty acid and glycerin, and triacetin.
[8] A fragrance composition containing the plant extract according to [5] or [6] or the composition according to [7].
[9] The fragrance composition according to [8], which contains 1 ppb to 1000 ppm of 2-acetyl-1-pyrrolin.
[10] A product selected from the group consisting of beverages, foods, pharmaceuticals, quasi-drugs, tobacco, cosmetics, oral care products and feeds, which comprises the perfume composition according to [8] or [9].
[11] 2-Acetyl-1-pyrroline comprises mixing 2-acetyl-1-pyrrolin with one or two edible oils selected from the group consisting of triesters (MCTs) of medium chain fatty acids and glycerin and triacetin. -1-Method for stabilizing pyrolin.
[12] The stability according to [11], wherein the residual rate of 2-acetyl-1-pyrrolin is 60% or more when 2-acetyl-1-pyrrolin having a concentration of 10 ppm is stored in a dark place at 30 ° C. for 2 months. How to make it.
［１］２－アセチル－１－ピロリンを含む植物抽出物の製造方法であって、
２－アセチル－１－ピロリンを含む植物原料を中鎖脂肪酸とグリセリンとのトリエステル（ＭＣＴ）およびトリアセチンからなる群より選ばれる１種または２種の食用油で抽出する抽出工程を含む、前記植物抽出物の製造方法。
［２］前記抽出工程の前に、水蒸気蒸留、水抽出または温水抽出によって前記植物原料を処理する前処理工程を含む、［１］に記載の製造方法。
［３］前記抽出工程で得られた抽出物を脱水および濾過する後処理工程を含む、［１］または［２］に記載の製造方法。
［４］前記植物原料が、パンダンリーフ、ダダチャ豆、香り米およびトウモロコシからなる群より選ばれる１種以上である、［１］から［３］のいずれか一項に記載の製造方法。
［５］［１］から［４］のいずれか一項に記載の製造方法で製造された植物抽出物であって、２－アセチル－１－ピロリンを１ｐｐｂ～１０００ｐｐｍ含む、植物抽出物。
［６］３０℃暗所で、濃度１０ｐｐｍの２－アセチル－１－ピロリンを２ヶ月間保存したときの２－アセチル－１－ピロリンの残存率が６０％以上である、［５］に記載の植物抽出物。
［７］２－アセチル－１－ピロリン、および
中鎖脂肪酸とグリセリンとのトリエステル（ＭＣＴ）およびトリアセチンからなる群より選ばれる１種または２種の食用油
を含む組成物。
［８］［５］または［６］に記載の植物抽出物、または［７］に記載の組成物を含む香料組成物。
［９］２－アセチル－１－ピロリンを１ｐｐｂ～１０００ｐｐｍ含む、［８］に記載の香料組成物。
［１０］［８］または［９］に記載の香料組成物を含む、飲料、食品、医薬品、医薬部外品、たばこ、香粧品、オーラルケア製品および飼料からなる群より選ばれる製品。
［１１］２－アセチル－１－ピロリンを、中鎖脂肪酸とグリセリンとのトリエステル（ＭＣＴ）およびトリアセチンからなる群より選ばれる１種または２種の食用油と混合することを含む、２－アセチル－１－ピロリンの安定化方法。
［１２］３０℃暗所で濃度１０ｐｐｍの２－アセチル－１－ピロリンを２ヶ月間保存したときの２－アセチル－１－ピロリンの残存率が６０％以上である、［１１］に記載の安定化方法。 The present invention is as shown below.
[1] A method for producing a plant extract containing 2-acetyl-1-pyrrolin.
The plant comprising an extraction step of extracting a plant material containing 2-acetyl-1-pyrrolin with one or two edible oils selected from the group consisting of triesters (MCTs) of medium chain fatty acids and glycerin and triacetin. How to make an extract.
[2] The production method according to [1], which comprises a pretreatment step of treating the plant raw material by steam distillation, water extraction or hot water extraction before the extraction step.
[3] The production method according to [1] or [2], which comprises a post-treatment step of dehydrating and filtering the extract obtained in the extraction step.
[4] The production method according to any one of [1] to [3], wherein the plant raw material is at least one selected from the group consisting of pandan leaf, dadacha beans, aromatic rice and corn.
[5] A plant extract produced by the production method according to any one of [1] to [4], which contains 1 ppb to 1000 ppm of 2-acetyl-1-pyrrolin.
[6] The remaining rate of 2-acetyl-1-pyrrolin when 2-acetyl-1-pyrrolin at a concentration of 10 ppm is stored for 2 months in a dark place at 30 ° C. is 60% or more, according to [5]. Plant extract.
[7] A composition containing one or two edible oils selected from the group consisting of 2-acetyl-1-pyrroline, a triester (MCT) of a medium-chain fatty acid and glycerin, and triacetin.
[8] A fragrance composition containing the plant extract according to [5] or [6] or the composition according to [7].
[9] The fragrance composition according to [8], which contains 1 ppb to 1000 ppm of 2-acetyl-1-pyrrolin.
[10] A product selected from the group consisting of beverages, foods, pharmaceuticals, quasi-drugs, tobacco, cosmetics, oral care products and feeds, which comprises the perfume composition according to [8] or [9].
[11] 2-Acetyl-1-pyrroline comprises mixing 2-acetyl-1-pyrrolin with one or two edible oils selected from the group consisting of triesters (MCTs) of medium chain fatty acids and glycerin and triacetin. -1-Method for stabilizing pyrolin.
[12] The stability according to [11], wherein the residual rate of 2-acetyl-1-pyrrolin is 60% or more when 2-acetyl-1-pyrrolin having a concentration of 10 ppm is stored in a dark place at 30 ° C. for 2 months. How to make it.
本発明によれば、特定の食用油と組み合わせることで、２－アセチル－１－ピロリンを安定に存在させることができ、それにより２－アセチル－１－ピロリンの特徴的な香りを持続させることができるため、各種製品に用いられる香料素材として好適に用いることができる。
本発明の一態様によれば、２－アセチル－１－ピロリンを植物から抽出することにより、簡便かつ安全な方法で、工業的規模で２－アセチル－１－ピロリンが得られるだけでなく、ナチュラル感に富んだ香料素材を提供することができる。 According to the present invention, when combined with a specific cooking oil, 2-acetyl-1-pyrrolin can be stably present, thereby sustaining the characteristic aroma of 2-acetyl-1-pyrrolin. Therefore, it can be suitably used as a fragrance material used in various products.
According to one aspect of the present invention, by extracting 2-acetyl-1-pyrrolin from a plant, not only 2-acetyl-1-pyrrolin can be obtained on an industrial scale by a simple and safe method, but also natural. It is possible to provide a fragrance material with a rich sense.
本発明の一態様によれば、２－アセチル－１－ピロリンを植物から抽出することにより、簡便かつ安全な方法で、工業的規模で２－アセチル－１－ピロリンが得られるだけでなく、ナチュラル感に富んだ香料素材を提供することができる。 According to the present invention, when combined with a specific cooking oil, 2-acetyl-1-pyrrolin can be stably present, thereby sustaining the characteristic aroma of 2-acetyl-1-pyrrolin. Therefore, it can be suitably used as a fragrance material used in various products.
According to one aspect of the present invention, by extracting 2-acetyl-1-pyrrolin from a plant, not only 2-acetyl-1-pyrrolin can be obtained on an industrial scale by a simple and safe method, but also natural. It is possible to provide a fragrance material with a rich sense.
以下、本発明の各実施態様について具体的に説明する。
Hereinafter, each embodiment of the present invention will be specifically described.
１）２－アセチル－１－ピロリンを含む植物抽出物の製造方法
まず、本発明の一態様である２－アセチル－１－ピロリンを含む植物抽出物の製造方法について説明する。
本発明の２－アセチル－１－ピロリンを含む植物抽出物の製造方法は、２－アセチル－１－ピロリンを含む植物原料を中鎖脂肪酸とグリセリンとのトリエステル（ＭＣＴ）およびトリアセチンからなる群より選ばれる１種または２種の食用油で抽出する抽出工程を含むことを特徴とする。 1) Method for Producing Plant Extract Containing 2-Acetyl-1-pyrrolin First, a method for producing a plant extract containing 2-acetyl-1-pyrrolin, which is one aspect of the present invention, will be described.
In the method for producing a plant extract containing 2-acetyl-1-pyrrolin of the present invention, a plant raw material containing 2-acetyl-1-pyrrolin is composed of a triester (MCT) of a medium-chain fatty acid and glycerin and triacetin. It is characterized by including an extraction step of extracting with one or two selected edible oils.
まず、本発明の一態様である２－アセチル－１－ピロリンを含む植物抽出物の製造方法について説明する。
本発明の２－アセチル－１－ピロリンを含む植物抽出物の製造方法は、２－アセチル－１－ピロリンを含む植物原料を中鎖脂肪酸とグリセリンとのトリエステル（ＭＣＴ）およびトリアセチンからなる群より選ばれる１種または２種の食用油で抽出する抽出工程を含むことを特徴とする。 1) Method for Producing Plant Extract Containing 2-Acetyl-1-pyrrolin First, a method for producing a plant extract containing 2-acetyl-1-pyrrolin, which is one aspect of the present invention, will be described.
In the method for producing a plant extract containing 2-acetyl-1-pyrrolin of the present invention, a plant raw material containing 2-acetyl-1-pyrrolin is composed of a triester (MCT) of a medium-chain fatty acid and glycerin and triacetin. It is characterized by including an extraction step of extracting with one or two selected edible oils.
本発明の植物抽出物の製造方法は、植物原料から２－アセチル－１－ピロリンを抽出するものであるため、安全性に優れており、煩雑な精製工程を経ることなく、２－アセチル－１－ピロリンを工業的規模で得ることができる。また、ナチュラル感に富んだ香料素材を提供することができる。また、本発明の植物抽出物の製造方法は、抽出溶媒として、中鎖脂肪酸とグリセリンとのトリエステル（ＭＣＴ）およびトリアセチンからなる群より選ばれる１種または２種の食用油を用いることにより、得られた植物抽出物中で２－アセチル－１－ピロリンを長期間安定に存在させることができ、２－アセチル－１－ピロリンの特徴的な香りを持続させることができる。
Since the method for producing a plant extract of the present invention extracts 2-acetyl-1-pyrrolin from a plant raw material, it is excellent in safety and 2-acetyl-1 without going through a complicated purification step. -Pyrrolin can be obtained on an industrial scale. In addition, it is possible to provide a fragrance material rich in natural feeling. Further, in the method for producing a plant extract of the present invention, one or two kinds of edible oils selected from the group consisting of triester (MCT) of medium chain fatty acid and glycerin and triacetin are used as an extraction solvent. 2-Acetyl-1-pyrrolin can be stably present in the obtained plant extract for a long period of time, and the characteristic aroma of 2-acetyl-1-pyrrolin can be maintained.
＜抽出工程＞
本工程では、２－アセチル－１－ピロリンを含む植物原料を中鎖脂肪酸とグリセリンとのトリエステル（ＭＣＴ）およびトリアセチンからなる群より選ばれる１種または２種の食用油で抽出する。 <Extraction process>
In this step, a plant material containing 2-acetyl-1-pyrrolin is extracted with one or two edible oils selected from the group consisting of triesters (MCTs) of medium-chain fatty acids and glycerin and triacetin.
本工程では、２－アセチル－１－ピロリンを含む植物原料を中鎖脂肪酸とグリセリンとのトリエステル（ＭＣＴ）およびトリアセチンからなる群より選ばれる１種または２種の食用油で抽出する。 <Extraction process>
In this step, a plant material containing 2-acetyl-1-pyrrolin is extracted with one or two edible oils selected from the group consisting of triesters (MCTs) of medium-chain fatty acids and glycerin and triacetin.
植物原料としては、２－アセチル－１－ピロリンを含むものであれば特に限定されない。そのような植物原料としては、例えば、パンダンリーフ、ダダチャ豆、香り米およびトウモロコシからなる群より選ばれる１種以上が挙げられる。これらの中でも、２－アセチル－１－ピロリンを多く含む点で、パンダンリーフが好ましい。
The plant raw material is not particularly limited as long as it contains 2-acetyl-1-pyrrolin. Examples of such plant raw materials include one or more selected from the group consisting of pandan leaf, dadacha beans, aromatic rice and corn. Among these, pandan leaf is preferable because it contains a large amount of 2-acetyl-1-pyrrolin.
抽出溶媒としては、中鎖脂肪酸とグリセリンとのトリエステル（ＭＣＴ）およびトリアセチンからなる群より選ばれる１種または２種の食用油が用いられる。これらの食用油は、２－アセチル－１－ピロリンを安定な状態で保持する効果がある。本発明においては、これらの食用油を抽出溶媒として用いることで、得られた植物抽出物中でそのまま２－アセチル－１－ピロリンを安定に存在させることができる。
ＭＣＴとしては、例えば炭素数５～１２、好ましくは６～１０の中鎖脂肪酸とグリセリンとのトリエステルが挙げられる。中でも、トリカプロン酸グリセリル、トリカプリル酸グリセリル、トリカプリン酸グリセリルおよびこれらの組み合わせなどが好ましく挙げられる。
食用油と植物原料の使用比率（質量基準）は、１：１～１：３０が好ましく、１：２～１：１５がより好ましく、１：３～１：１０がさらに好ましい。 As the extraction solvent, one or two kinds of edible oils selected from the group consisting of triester (MCT) of medium-chain fatty acid and glycerin and triacetin are used. These cooking oils have the effect of retaining 2-acetyl-1-pyrrolin in a stable state. In the present invention, by using these cooking oils as an extraction solvent, 2-acetyl-1-pyrrolin can be stably present in the obtained plant extract as it is.
Examples of the MCT include a triester of a medium-chain fatty acid having 5 to 12 carbon atoms, preferably 6 to 10 carbon atoms and glycerin. Among them, glyceryl tricaproate, glyceryl tricaprylate, glyceryl tricaprate and combinations thereof are preferably mentioned.
The ratio of cooking oil to plant raw materials (based on mass) is preferably 1: 1 to 1:30, more preferably 1: 2 to 1:15, and even more preferably 1: 3 to 1:10.
ＭＣＴとしては、例えば炭素数５～１２、好ましくは６～１０の中鎖脂肪酸とグリセリンとのトリエステルが挙げられる。中でも、トリカプロン酸グリセリル、トリカプリル酸グリセリル、トリカプリン酸グリセリルおよびこれらの組み合わせなどが好ましく挙げられる。
食用油と植物原料の使用比率（質量基準）は、１：１～１：３０が好ましく、１：２～１：１５がより好ましく、１：３～１：１０がさらに好ましい。 As the extraction solvent, one or two kinds of edible oils selected from the group consisting of triester (MCT) of medium-chain fatty acid and glycerin and triacetin are used. These cooking oils have the effect of retaining 2-acetyl-1-pyrrolin in a stable state. In the present invention, by using these cooking oils as an extraction solvent, 2-acetyl-1-pyrrolin can be stably present in the obtained plant extract as it is.
Examples of the MCT include a triester of a medium-chain fatty acid having 5 to 12 carbon atoms, preferably 6 to 10 carbon atoms and glycerin. Among them, glyceryl tricaproate, glyceryl tricaprylate, glyceryl tricaprate and combinations thereof are preferably mentioned.
The ratio of cooking oil to plant raw materials (based on mass) is preferably 1: 1 to 1:30, more preferably 1: 2 to 1:15, and even more preferably 1: 3 to 1:10.
抽出方法は特に限定されなく、抽出溶媒である食用油中で植物原料を浸漬または加熱還流するなどして食用油と植物原料とを接触させることで、植物原料から２－アセチル－１－ピロリンを抽出する。２－アセチル－１－ピロリンの抽出効率を高めるため、植物原料を予め粉砕処理してもよい。また、植物原料を基質として、細菌・真菌等により発酵処理してもよい。
The extraction method is not particularly limited, and 2-acetyl-1-pyrrolin can be obtained from the plant material by bringing the plant material into contact with the plant material by immersing the plant material in the cooking oil which is the extraction solvent or by heating and refluxing. Extract. In order to increase the extraction efficiency of 2-acetyl-1-pyrrolin, the plant material may be pulverized in advance. In addition, a plant material may be used as a substrate for fermentation treatment with bacteria, fungi, or the like.
抽出温度、時間、圧力等の条件は、抽出方法によって当業者が適宜決定すればよい。
浸漬法により抽出する場合、抽出温度は加熱、室温または冷却条件下のいずれであってもよく特に限定されないが、抽出効率の観点から１０～１００℃が好ましく、２５～９０℃がより好ましく、３０～７０℃がさらに好ましい。
抽出時間は、抽出効率を考慮して決定すればよく特に限定されないが、通常、安定性の観点から０．５～７２時間が好ましく、１～２４時間がより好ましく、１～１２時間がさらに好ましい。
抽出圧力は、常圧、減圧、加圧下のいずれであってもよく、特に限定されないが、通常、安定性の観点から常圧が好ましい。 Conditions such as extraction temperature, time, and pressure may be appropriately determined by those skilled in the art depending on the extraction method.
When extracting by the dipping method, the extraction temperature may be any of heating, room temperature and cooling conditions, but is not particularly limited, but from the viewpoint of extraction efficiency, 10 to 100 ° C. is preferable, 25 to 90 ° C. is more preferable, and 30 ° C. -70 ° C is more preferable.
The extraction time may be determined in consideration of the extraction efficiency and is not particularly limited, but is usually preferably 0.5 to 72 hours, more preferably 1 to 24 hours, still more preferably 1 to 12 hours from the viewpoint of stability. ..
The extraction pressure may be normal pressure, reduced pressure, or pressurized, and is not particularly limited, but usually, normal pressure is preferable from the viewpoint of stability.
浸漬法により抽出する場合、抽出温度は加熱、室温または冷却条件下のいずれであってもよく特に限定されないが、抽出効率の観点から１０～１００℃が好ましく、２５～９０℃がより好ましく、３０～７０℃がさらに好ましい。
抽出時間は、抽出効率を考慮して決定すればよく特に限定されないが、通常、安定性の観点から０．５～７２時間が好ましく、１～２４時間がより好ましく、１～１２時間がさらに好ましい。
抽出圧力は、常圧、減圧、加圧下のいずれであってもよく、特に限定されないが、通常、安定性の観点から常圧が好ましい。 Conditions such as extraction temperature, time, and pressure may be appropriately determined by those skilled in the art depending on the extraction method.
When extracting by the dipping method, the extraction temperature may be any of heating, room temperature and cooling conditions, but is not particularly limited, but from the viewpoint of extraction efficiency, 10 to 100 ° C. is preferable, 25 to 90 ° C. is more preferable, and 30 ° C. -70 ° C is more preferable.
The extraction time may be determined in consideration of the extraction efficiency and is not particularly limited, but is usually preferably 0.5 to 72 hours, more preferably 1 to 24 hours, still more preferably 1 to 12 hours from the viewpoint of stability. ..
The extraction pressure may be normal pressure, reduced pressure, or pressurized, and is not particularly limited, but usually, normal pressure is preferable from the viewpoint of stability.
なお、本発明においては、同じ植物原料を複数回抽出してもよい。また、植物抽出物中の２－アセチル－１－ピロリンの濃度を高めるなどの目的で、植物原料を抽出した抽出溶媒で異なる植物原料を複数回抽出してもよい。
In the present invention, the same plant material may be extracted multiple times. Further, different plant raw materials may be extracted a plurality of times with the extraction solvent from which the plant raw materials are extracted for the purpose of increasing the concentration of 2-acetyl-1-pyrrolin in the plant extract.
抽出操作の後、冷却、静置または遠心分離等の任意の方法によって抽出液を分離して植物抽出物を得ることができる。
After the extraction operation, the extract can be separated to obtain a plant extract by any method such as cooling, standing or centrifuging.
＜前処理工程＞
本発明においては、２－アセチル－１－ピロリンの抽出効率をより高めるため、抽出工程の前に、水蒸気蒸留、水抽出または温水抽出によって植物原料を処理する前処理工程を行ってもよい。温度、時間および圧力等の条件は、処理方法によって当業者が適宜決定すればよい。なお、水抽出によって植物原料を処理する場合、水の温度は１０～３０℃が好ましく、温水抽出によって植物原料を処理する場合、水の温度は３０～６０℃が好ましい。 <Pretreatment process>
In the present invention, in order to further increase the extraction efficiency of 2-acetyl-1-pyrrolin, a pretreatment step of treating the plant raw material by steam distillation, water extraction or warm water extraction may be performed before the extraction step. Conditions such as temperature, time and pressure may be appropriately determined by those skilled in the art depending on the treatment method. When the plant raw material is treated by water extraction, the temperature of water is preferably 10 to 30 ° C., and when the plant raw material is treated by hot water extraction, the temperature of water is preferably 30 to 60 ° C.
本発明においては、２－アセチル－１－ピロリンの抽出効率をより高めるため、抽出工程の前に、水蒸気蒸留、水抽出または温水抽出によって植物原料を処理する前処理工程を行ってもよい。温度、時間および圧力等の条件は、処理方法によって当業者が適宜決定すればよい。なお、水抽出によって植物原料を処理する場合、水の温度は１０～３０℃が好ましく、温水抽出によって植物原料を処理する場合、水の温度は３０～６０℃が好ましい。 <Pretreatment process>
In the present invention, in order to further increase the extraction efficiency of 2-acetyl-1-pyrrolin, a pretreatment step of treating the plant raw material by steam distillation, water extraction or warm water extraction may be performed before the extraction step. Conditions such as temperature, time and pressure may be appropriately determined by those skilled in the art depending on the treatment method. When the plant raw material is treated by water extraction, the temperature of water is preferably 10 to 30 ° C., and when the plant raw material is treated by hot water extraction, the temperature of water is preferably 30 to 60 ° C.
水蒸気蒸留、水抽出または温水抽出によって植物原料を前処理する場合、水または温水は、安定性の観点から、リン酸緩衝液などの緩衝液によってｐＨ値を５～９の範囲に調整することが好ましい。
水蒸気蒸留、水抽出または温水抽出操作の後、冷却、静置または遠心分離等の任意の方法によって前処理抽出液を分離することができる。
なお、前処理工程を行う場合は、前処理抽出液を、食用油と接触させることで、前記抽出工程を行う。 When pretreating plant material by steam distillation, water extraction or hot water extraction, the pH value of water or hot water may be adjusted to the range of 5-9 with a buffer such as phosphate buffer from the viewpoint of stability. preferable.
After the steam distillation, water extraction or hot water extraction operation, the pretreatment extract can be separated by any method such as cooling, standing or centrifuging.
When the pretreatment step is performed, the extraction step is performed by bringing the pretreatment extract into contact with cooking oil.
水蒸気蒸留、水抽出または温水抽出操作の後、冷却、静置または遠心分離等の任意の方法によって前処理抽出液を分離することができる。
なお、前処理工程を行う場合は、前処理抽出液を、食用油と接触させることで、前記抽出工程を行う。 When pretreating plant material by steam distillation, water extraction or hot water extraction, the pH value of water or hot water may be adjusted to the range of 5-9 with a buffer such as phosphate buffer from the viewpoint of stability. preferable.
After the steam distillation, water extraction or hot water extraction operation, the pretreatment extract can be separated by any method such as cooling, standing or centrifuging.
When the pretreatment step is performed, the extraction step is performed by bringing the pretreatment extract into contact with cooking oil.
＜後処理工程＞
抽出工程で得られた２－アセチル－１－ピロリンを含む植物抽出物は、そのままでも香料素材として用いることができるが、脱水および濾過する後処理工程を行うことが好ましい。後処理工程を行うことで、溶媒に不要な固形物を除去し、水分を除去して２－アセチル－１－ピロリンの安定性をより高めることができる。 <Post-treatment process>
The plant extract containing 2-acetyl-1-pyrrolin obtained in the extraction step can be used as it is as a fragrance material, but it is preferable to carry out a post-treatment step of dehydration and filtration. By performing the post-treatment step, the solid matter unnecessary for the solvent can be removed, the water content can be removed, and the stability of 2-acetyl-1-pyrrolin can be further enhanced.
抽出工程で得られた２－アセチル－１－ピロリンを含む植物抽出物は、そのままでも香料素材として用いることができるが、脱水および濾過する後処理工程を行うことが好ましい。後処理工程を行うことで、溶媒に不要な固形物を除去し、水分を除去して２－アセチル－１－ピロリンの安定性をより高めることができる。 <Post-treatment process>
The plant extract containing 2-acetyl-1-pyrrolin obtained in the extraction step can be used as it is as a fragrance material, but it is preferable to carry out a post-treatment step of dehydration and filtration. By performing the post-treatment step, the solid matter unnecessary for the solvent can be removed, the water content can be removed, and the stability of 2-acetyl-1-pyrrolin can be further enhanced.
２）２－アセチル－１－ピロリンを含む植物抽出物
本発明の植物抽出物の製造方法により、２－アセチル－１－ピロリンを含む植物抽出物を得ることができる。得られた植物抽出物は、そのまま香料素材として用いてもよいし、必要に応じて、中鎖脂肪酸とグリセリンとのトリエステル（ＭＣＴ）およびトリアセチンからなる群より選ばれる１種または２種の食用油で希釈して香料素材として用いてもよい。希釈液として用いる食用油は、抽出溶媒と同じであっても異なっていてもよい。 2) Plant extract containing 2-acetyl-1-pyrrolin A plant extract containing 2-acetyl-1-pyrrolin can be obtained by the method for producing a plant extract of the present invention. The obtained plant extract may be used as it is as a perfume material, or if necessary, one or two edible species selected from the group consisting of triester (MCT) of medium-chain fatty acid and glycerin and triacetin. It may be diluted with oil and used as a fragrance material. The cooking oil used as the diluent may be the same as or different from the extraction solvent.
本発明の植物抽出物の製造方法により、２－アセチル－１－ピロリンを含む植物抽出物を得ることができる。得られた植物抽出物は、そのまま香料素材として用いてもよいし、必要に応じて、中鎖脂肪酸とグリセリンとのトリエステル（ＭＣＴ）およびトリアセチンからなる群より選ばれる１種または２種の食用油で希釈して香料素材として用いてもよい。希釈液として用いる食用油は、抽出溶媒と同じであっても異なっていてもよい。 2) Plant extract containing 2-acetyl-1-pyrrolin A plant extract containing 2-acetyl-1-pyrrolin can be obtained by the method for producing a plant extract of the present invention. The obtained plant extract may be used as it is as a perfume material, or if necessary, one or two edible species selected from the group consisting of triester (MCT) of medium-chain fatty acid and glycerin and triacetin. It may be diluted with oil and used as a fragrance material. The cooking oil used as the diluent may be the same as or different from the extraction solvent.
本発明の植物抽出物において、２－アセチル－１－ピロリンの含有量（質量基準）は、１ｐｐｂ～１０００ｐｐｍであることが好ましく、０．１～５００ｐｐｍがより好ましく、１０～１００ｐｐｍがさらに好ましい。
In the plant extract of the present invention, the content (mass basis) of 2-acetyl-1-pyrrolin is preferably 1 ppb to 1000 ppm, more preferably 0.1 to 500 ppm, still more preferably 10 to 100 ppm.
本発明の植物抽出物は、ナチュラル感に富んでおり、各種製品、特に飲料、食品、医薬品、医薬部外品、たばこ、香粧品、オーラルケア製品および飼料などの香料素材として好適に用いることができる。
また、本発明の植物抽出物は、抽出溶媒として中鎖脂肪酸とグリセリンとのトリエステル（ＭＣＴ）およびトリアセチンからなる群より選ばれる１種または２種の食用油が用いられ、そのまま食用油を担体として２－アセチル－１－ピロリンが保持されているため、２－アセチル－１－ピロリンを安定に存在させることができる。 The plant extract of the present invention is rich in natural feeling and can be suitably used as a fragrance material for various products, especially beverages, foods, pharmaceuticals, quasi-drugs, tobacco, cosmetics, oral care products and feeds. it can.
Further, in the plant extract of the present invention, one or two kinds of edible oil selected from the group consisting of triester (MCT) of medium-chain fatty acid and glycerin and triacetin are used as the extraction solvent, and the edible oil is used as a carrier as it is. Since 2-acetyl-1-pyrrolin is retained as a substance, 2-acetyl-1-pyrrolin can be stably present.
また、本発明の植物抽出物は、抽出溶媒として中鎖脂肪酸とグリセリンとのトリエステル（ＭＣＴ）およびトリアセチンからなる群より選ばれる１種または２種の食用油が用いられ、そのまま食用油を担体として２－アセチル－１－ピロリンが保持されているため、２－アセチル－１－ピロリンを安定に存在させることができる。 The plant extract of the present invention is rich in natural feeling and can be suitably used as a fragrance material for various products, especially beverages, foods, pharmaceuticals, quasi-drugs, tobacco, cosmetics, oral care products and feeds. it can.
Further, in the plant extract of the present invention, one or two kinds of edible oil selected from the group consisting of triester (MCT) of medium-chain fatty acid and glycerin and triacetin are used as the extraction solvent, and the edible oil is used as a carrier as it is. Since 2-acetyl-1-pyrrolin is retained as a substance, 2-acetyl-1-pyrrolin can be stably present.
本発明の好ましい態様によれば、３０℃暗所で、濃度（質量基準）１０ｐｐｍの２－アセチル－１－ピロリンを２ヶ月間保存したときの２－アセチル－１－ピロリンの残存率は６０％以上であり、７０％以上がより好ましく、８０％以上がさらに好ましい。なお、本明細書において、２－アセチル－１－ピロリンの残存率（％）は、下記式で求めることができる。
（３０℃暗所で２ヶ月間保存したときの２－アセチル－１－ピロリンの濃度ｐｐｍ）／（安定性試験開始時の２－アセチル－１－ピロリンの濃度１０ｐｐｍ）×１００（％） According to a preferred embodiment of the present invention, the residual rate of 2-acetyl-1-pyrroline is 60% when 2-acetyl-1-pyrroline at a concentration (mass basis) of 10 ppm is stored for 2 months in a dark place at 30 ° C. As mentioned above, 70% or more is more preferable, and 80% or more is further preferable. In the present specification, the residual rate (%) of 2-acetyl-1-pyrrolin can be calculated by the following formula.
(Concentration of 2-acetyl-1-pyrrolin when stored in a dark place at 30 ° C. for 2 months ppm) / (Concentration of 2-acetyl-1-pyrrolin at the start of stability test 10 ppm) × 100 (%)
（３０℃暗所で２ヶ月間保存したときの２－アセチル－１－ピロリンの濃度ｐｐｍ）／（安定性試験開始時の２－アセチル－１－ピロリンの濃度１０ｐｐｍ）×１００（％） According to a preferred embodiment of the present invention, the residual rate of 2-acetyl-1-pyrroline is 60% when 2-acetyl-1-pyrroline at a concentration (mass basis) of 10 ppm is stored for 2 months in a dark place at 30 ° C. As mentioned above, 70% or more is more preferable, and 80% or more is further preferable. In the present specification, the residual rate (%) of 2-acetyl-1-pyrrolin can be calculated by the following formula.
(Concentration of 2-acetyl-1-pyrrolin when stored in a dark place at 30 ° C. for 2 months ppm) / (Concentration of 2-acetyl-1-pyrrolin at the start of stability test 10 ppm) × 100 (%)
３）２－アセチル－１－ピロリンおよび食用油を含む組成物
本発明の組成物は、２－アセチル－１－ピロリン、および中鎖脂肪酸とグリセリンとのトリエステル（ＭＣＴ）およびトリアセチンからなる群より選ばれる１種または２種の食用油を含むことを特徴とする。
２－アセチル－１－ピロリンは、２－アセチル－１－ピロリンを含む植物原料から抽出したものであってもよいし、合成により得られたものであってもよい。
本発明の組成物においては、中鎖脂肪酸とグリセリンとのトリエステル（ＭＣＴ）およびトリアセチンからなる群より選ばれる１種または２種の食用油中に２－アセチル－１－ピロリンが溶解または分散しているため、２－アセチル－１－ピロリンを安定に存在させることができる。
本発明の好ましい態様によれば、３０℃暗所で、濃度１０ｐｐｍの２－アセチル－１－ピロリンを２ヶ月間保存したときの２－アセチル－１－ピロリンの残存率は６０％以上であり、７０％以上がより好ましく、８０％以上がさらに好ましい。 3) Composition containing 2-acetyl-1-pyrrolin and edible oil The composition of the present invention consists of 2-acetyl-1-pyrrolin, a triester (MCT) of a medium-chain fatty acid and glycerin, and triacetin. It is characterized by containing one or two selected edible oils.
2-Acetyl-1-pyrrolin may be extracted from a plant material containing 2-acetyl-1-pyrrolin, or may be obtained by synthesis.
In the composition of the present invention, 2-acetyl-1-pyrrolin is dissolved or dispersed in one or two edible oils selected from the group consisting of triesters (MCTs) of medium-chain fatty acids and glycerin and triacetin. Therefore, 2-acetyl-1-pyrrolin can be stably present.
According to a preferred embodiment of the present invention, the residual rate of 2-acetyl-1-pyrrolin when 2-acetyl-1-pyrrolin at a concentration of 10 ppm is stored for 2 months in a dark place at 30 ° C. is 60% or more. 70% or more is more preferable, and 80% or more is further preferable.
本発明の組成物は、２－アセチル－１－ピロリン、および中鎖脂肪酸とグリセリンとのトリエステル（ＭＣＴ）およびトリアセチンからなる群より選ばれる１種または２種の食用油を含むことを特徴とする。
２－アセチル－１－ピロリンは、２－アセチル－１－ピロリンを含む植物原料から抽出したものであってもよいし、合成により得られたものであってもよい。
本発明の組成物においては、中鎖脂肪酸とグリセリンとのトリエステル（ＭＣＴ）およびトリアセチンからなる群より選ばれる１種または２種の食用油中に２－アセチル－１－ピロリンが溶解または分散しているため、２－アセチル－１－ピロリンを安定に存在させることができる。
本発明の好ましい態様によれば、３０℃暗所で、濃度１０ｐｐｍの２－アセチル－１－ピロリンを２ヶ月間保存したときの２－アセチル－１－ピロリンの残存率は６０％以上であり、７０％以上がより好ましく、８０％以上がさらに好ましい。 3) Composition containing 2-acetyl-1-pyrrolin and edible oil The composition of the present invention consists of 2-acetyl-1-pyrrolin, a triester (MCT) of a medium-chain fatty acid and glycerin, and triacetin. It is characterized by containing one or two selected edible oils.
2-Acetyl-1-pyrrolin may be extracted from a plant material containing 2-acetyl-1-pyrrolin, or may be obtained by synthesis.
In the composition of the present invention, 2-acetyl-1-pyrrolin is dissolved or dispersed in one or two edible oils selected from the group consisting of triesters (MCTs) of medium-chain fatty acids and glycerin and triacetin. Therefore, 2-acetyl-1-pyrrolin can be stably present.
According to a preferred embodiment of the present invention, the residual rate of 2-acetyl-1-pyrrolin when 2-acetyl-1-pyrrolin at a concentration of 10 ppm is stored for 2 months in a dark place at 30 ° C. is 60% or more. 70% or more is more preferable, and 80% or more is further preferable.
４）香料組成物
本発明の香料組成物は、前記植物抽出物または前記組成物を含むことを特徴とする。
本発明の香料組成物において、２－アセチル－１－ピロリンの含有量（質量基準）は、用途や目的に応じて適宜決定されるものであり、特に限定されないが、通常、０．０１ｐｐｂ～１０００ｐｐｍであることが好ましく、０．１ｐｐｂ～１０ｐｐｍがより好ましく、１ｐｐｂ～１００ｐｐｂがさらに好ましい。 4) Fragrance composition The fragrance composition of the present invention is characterized by containing the plant extract or the composition.
In the fragrance composition of the present invention, the content (mass basis) of 2-acetyl-1-pyrrolin is appropriately determined according to the intended use and purpose, and is not particularly limited, but is usually 0.01 ppb to 1000 ppm. It is preferably 0.1 ppb to 10 ppm, more preferably 1 ppb to 100 ppb.
本発明の香料組成物は、前記植物抽出物または前記組成物を含むことを特徴とする。
本発明の香料組成物において、２－アセチル－１－ピロリンの含有量（質量基準）は、用途や目的に応じて適宜決定されるものであり、特に限定されないが、通常、０．０１ｐｐｂ～１０００ｐｐｍであることが好ましく、０．１ｐｐｂ～１０ｐｐｍがより好ましく、１ｐｐｂ～１００ｐｐｂがさらに好ましい。 4) Fragrance composition The fragrance composition of the present invention is characterized by containing the plant extract or the composition.
In the fragrance composition of the present invention, the content (mass basis) of 2-acetyl-1-pyrrolin is appropriately determined according to the intended use and purpose, and is not particularly limited, but is usually 0.01 ppb to 1000 ppm. It is preferably 0.1 ppb to 10 ppm, more preferably 1 ppb to 100 ppb.
本発明の香料組成物は、各種添加剤を含んでいてもよい。添加剤としては、特に限定されないが、例えば、抗酸化剤、防腐剤、抗菌剤、ｐＨ調整剤、希釈剤、担体、その他の添加剤が挙げられる。これらの添加剤は、１種で用いてもよく、２種以上併用してもよい。
抗酸化剤としては、ブチルヒドロキシトルエン、ブチルヒドロキシアニソール、クエン酸、グルタチオン、セレン、リコペン、ビタミンＡ、ビタミンＥ、ビタミンＣ等の他、ピロロピロール誘導体、各種植物からの抽出物から得られるフリーラジカル消去剤（ｆｒｅｅ ｒａｄｉｃａｌ ｓｃａｖｅｎｇｅｒｓ）、スーパーオキサイドディスミューテース（ｓｕｐｅｒｏｘｉｄｅ ｄｉｓｍｕｔａｓｅ）やグルタチオンペルオキシダーゼなどの抗酸化特性を有する酵素などが挙げられる。
防腐剤または抗菌剤としては、安息香酸、安息香酸ナトリウム、パラオキシ安息香酸イソプロピル、パラオキシ安息香酸イソブチル、パラオキシ安息香酸エチル、パラオキシ安息香酸メチル、パラオキシ安息香酸ブチル、パラオキシ安息香酸プロピル、亜硫酸ナトリウム、次亜硫酸ナトリウム、ピロ亜硫酸カリウム、ソルビン酸、ソルビン酸カリウム、デヒドロ酢酸ナトリウム、ツヤプリシン、ウド抽出物、エゴノキ抽出物、カワラヨモギ抽出物、ウーロン茶抽出物、シラコタンパク抽出物、酵素分解ハトムギ抽出物、茶カテキン類、リンゴポリフェノール、ペクチン分解物、キトサン、リゾチーム、ε－ポリリジンなどが挙げられる。 The fragrance composition of the present invention may contain various additives. Additives are not particularly limited, and examples thereof include antioxidants, preservatives, antibacterial agents, pH adjusters, diluents, carriers, and other additives. These additives may be used alone or in combination of two or more.
Antioxidants include butylhydroxytoluene, butylhydroxyanisole, citric acid, glutathione, selenium, lycopene, vitamin A, vitamin E, vitamin C, etc., pyrolopyrrole derivatives, and free radicals obtained from extracts from various plants. Examples thereof include enzymes having antioxidant properties such as scavengers (free radicals), superoxide dismutase and glutathione peroxidase.
Preservatives or antibacterial agents include benzoic acid, sodium benzoate, isopropyl paraoxybenzoate, isobutyl paraoxybenzoate, ethyl paraoxybenzoate, methyl paraoxybenzoate, butyl paraoxybenzoate, propyl paraoxybenzoate, sodium hyposulfate, hyposulfate. Sodium, potassium pyrosulfate, sorbic acid, potassium sorbate, sodium dehydroacetate, luapricin, udo extract, egonoki extract, kawarayomogi extract, oolong tea extract, shirako protein extract, enzymatically decomposed honeybee extract, tea catechins, Examples include apple polyphenol, pectin decomposition product, chitosan, lysozyme, ε-polylysine and the like.
抗酸化剤としては、ブチルヒドロキシトルエン、ブチルヒドロキシアニソール、クエン酸、グルタチオン、セレン、リコペン、ビタミンＡ、ビタミンＥ、ビタミンＣ等の他、ピロロピロール誘導体、各種植物からの抽出物から得られるフリーラジカル消去剤（ｆｒｅｅ ｒａｄｉｃａｌ ｓｃａｖｅｎｇｅｒｓ）、スーパーオキサイドディスミューテース（ｓｕｐｅｒｏｘｉｄｅ ｄｉｓｍｕｔａｓｅ）やグルタチオンペルオキシダーゼなどの抗酸化特性を有する酵素などが挙げられる。
防腐剤または抗菌剤としては、安息香酸、安息香酸ナトリウム、パラオキシ安息香酸イソプロピル、パラオキシ安息香酸イソブチル、パラオキシ安息香酸エチル、パラオキシ安息香酸メチル、パラオキシ安息香酸ブチル、パラオキシ安息香酸プロピル、亜硫酸ナトリウム、次亜硫酸ナトリウム、ピロ亜硫酸カリウム、ソルビン酸、ソルビン酸カリウム、デヒドロ酢酸ナトリウム、ツヤプリシン、ウド抽出物、エゴノキ抽出物、カワラヨモギ抽出物、ウーロン茶抽出物、シラコタンパク抽出物、酵素分解ハトムギ抽出物、茶カテキン類、リンゴポリフェノール、ペクチン分解物、キトサン、リゾチーム、ε－ポリリジンなどが挙げられる。 The fragrance composition of the present invention may contain various additives. Additives are not particularly limited, and examples thereof include antioxidants, preservatives, antibacterial agents, pH adjusters, diluents, carriers, and other additives. These additives may be used alone or in combination of two or more.
Antioxidants include butylhydroxytoluene, butylhydroxyanisole, citric acid, glutathione, selenium, lycopene, vitamin A, vitamin E, vitamin C, etc., pyrolopyrrole derivatives, and free radicals obtained from extracts from various plants. Examples thereof include enzymes having antioxidant properties such as scavengers (free radicals), superoxide dismutase and glutathione peroxidase.
Preservatives or antibacterial agents include benzoic acid, sodium benzoate, isopropyl paraoxybenzoate, isobutyl paraoxybenzoate, ethyl paraoxybenzoate, methyl paraoxybenzoate, butyl paraoxybenzoate, propyl paraoxybenzoate, sodium hyposulfate, hyposulfate. Sodium, potassium pyrosulfate, sorbic acid, potassium sorbate, sodium dehydroacetate, luapricin, udo extract, egonoki extract, kawarayomogi extract, oolong tea extract, shirako protein extract, enzymatically decomposed honeybee extract, tea catechins, Examples include apple polyphenol, pectin decomposition product, chitosan, lysozyme, ε-polylysine and the like.
また、ｐＨ調整剤としては、アジピン酸、クエン酸、クエン酸三ナトリウム、グルコノデルタラクトン、グルコン酸、グルコン酸カリウム、グルコン酸ナトリウム、ＤＬ－酒石酸、Ｌ－酒石酸、ＤＬ－酒石酸水素カリウム、Ｌ－酒石酸水素カリウム、ＤＬ－酒石酸ナトリウム、Ｌ－酒石酸ナトリウム、炭酸カリウム（無水）、炭酸水素ナトリウム、炭酸ナトリウム、二酸化炭素、乳酸、乳酸ナトリウム、氷酢酸、ピロリン酸二水素二ナトリウム、フマル酸、フマル酸一ナトリウム、ＤＬ－リンゴ酸、ＤＬ－リンゴ酸ナトリウム、リン酸、リン酸水素二カリウム、リン酸二水素カリウム、リン酸水素二ナトリウム、リン酸二水素ナトリウムなどが挙げられる。
Examples of the pH adjuster include adipic acid, citric acid, trisodium citrate, gluconodeltalactone, gluconic acid, potassium gluconate, sodium gluconate, DL-tartaric acid, L-tartaric acid, DL-potassium hydrogen tartrate, and L. -Potataric acid hydrogen, DL-Sodium tartarate, L-Sodium tartarate, potassium carbonate (anhydrous), sodium hydrogen carbonate, sodium carbonate, carbon dioxide, lactic acid, sodium lactate, glacial acetic acid, disodium dihydrogen pyrophosphate, fumaric acid, fumal Examples thereof include monosodium acid, DL-tartaric acid, DL-sodium malate, phosphoric acid, dipotassium hydrogen phosphate, potassium dihydrogen phosphate, disodium hydrogen phosphate, and sodium dihydrogen phosphate.
希釈剤または担体としては、本発明の効果を妨げないものであれば特に限定されない。
例えば、スクロース、グルコース、デキストリン、澱粉類、サイクロデキストリン、トレハロース、ラクトース、マルトース、パラチノース、キシロース、水飴、液糖などの糖類；
エタノール、プロピレングリコール、グリセリン等のアルコール類；
還元水飴、還元麦芽糖水飴、ソルビトール、ラクチトール、パラチニット、マンニトール、キシリトール、エリスリトール、マルチトール等の糖アルコール；
アラビアガム、キサンタンガム、カラギーナン、グァーガム、ジェランガム等の多糖類
などが挙げられる。 The diluent or carrier is not particularly limited as long as it does not interfere with the effects of the present invention.
For example, sugars such as sucrose, glucose, dextrin, starches, cyclodextrin, trehalose, lactose, maltose, palatinose, xylose, candy, liquid sugar;
Alcohols such as ethanol, propylene glycol and glycerin;
Sugar alcohols such as reduced starch syrup, reduced maltose starch syrup, sorbitol, lactitol, palatinit, mannitol, xylitol, erythritol, maltitol;
Examples thereof include polysaccharides such as gum arabic, xanthan gum, carrageenan, guar gum and gellan gum.
例えば、スクロース、グルコース、デキストリン、澱粉類、サイクロデキストリン、トレハロース、ラクトース、マルトース、パラチノース、キシロース、水飴、液糖などの糖類；
エタノール、プロピレングリコール、グリセリン等のアルコール類；
還元水飴、還元麦芽糖水飴、ソルビトール、ラクチトール、パラチニット、マンニトール、キシリトール、エリスリトール、マルチトール等の糖アルコール；
アラビアガム、キサンタンガム、カラギーナン、グァーガム、ジェランガム等の多糖類
などが挙げられる。 The diluent or carrier is not particularly limited as long as it does not interfere with the effects of the present invention.
For example, sugars such as sucrose, glucose, dextrin, starches, cyclodextrin, trehalose, lactose, maltose, palatinose, xylose, candy, liquid sugar;
Alcohols such as ethanol, propylene glycol and glycerin;
Sugar alcohols such as reduced starch syrup, reduced maltose starch syrup, sorbitol, lactitol, palatinit, mannitol, xylitol, erythritol, maltitol;
Examples thereof include polysaccharides such as gum arabic, xanthan gum, carrageenan, guar gum and gellan gum.
その他の添加剤としては、キレート剤、香料、香辛料抽出物、可食性植物抽出物、果物抽出物、コールドプレスオイル低沸点画分、公知の酸化防止剤（例えばＢＨＴ、ＢＨＡ、α－トコフェロール、ビタミンＣなど）、保存料（例えばソルビン酸、安息香酸、しらこたん白抽出物）、日持ち向上剤（例えば酢酸ナトリウム、グリシン、グリセリン脂肪酸エステル、リゾチーム、キトサン）などが挙げられる。
Other additives include chelating agents, fragrances, spice extracts, edible plant extracts, fruit extracts, cold pressed oil low boiling fractions, known antioxidants (eg BHT, BHA, α-tocopherols, vitamins). Preservatives (eg, sorbic acid, benzoic acid, shirako protein extract), shelf life improvers (eg, sodium acetate, glycine, glycerin fatty acid ester, lysozyme, chitosan) and the like.
本発明の香料組成物は、飲料、食品、医薬品、医薬部外品、たばこ、香粧品、オーラルケア製品および飼料などに配合または賦香することができる。
飲料としては、例えば、炭酸飲料、果実飲料、無果汁飲料、野菜飲料、嗜好飲料、アルコール飲料、ノンアルコール飲料、茶飲料、ハーブティー、コーヒー飲料、機能性飲料、シュガーレス飲料、スポーツ飲料、栄養・滋養ドリンク、酪農製品、乳製品、乳酸菌飲料、ヨーグルト飲料、乳飲料、スープ類、各種インスタント飲料などが挙げられる。 The perfume composition of the present invention can be blended or aromatized in beverages, foods, pharmaceuticals, quasi-drugs, tobacco, cosmetics, oral care products, feeds and the like.
Beverages include, for example, carbonated beverages, fruit beverages, fruit-free beverages, vegetable beverages, favorite beverages, alcoholic beverages, non-alcoholic beverages, tea beverages, herbal teas, coffee beverages, functional beverages, sugarless beverages, sports beverages, nutrition.・ Nourishing drinks, dairy products, dairy products, lactic acid bacteria beverages, yogurt beverages, dairy beverages, soups, various instant beverages, etc.
飲料としては、例えば、炭酸飲料、果実飲料、無果汁飲料、野菜飲料、嗜好飲料、アルコール飲料、ノンアルコール飲料、茶飲料、ハーブティー、コーヒー飲料、機能性飲料、シュガーレス飲料、スポーツ飲料、栄養・滋養ドリンク、酪農製品、乳製品、乳酸菌飲料、ヨーグルト飲料、乳飲料、スープ類、各種インスタント飲料などが挙げられる。 The perfume composition of the present invention can be blended or aromatized in beverages, foods, pharmaceuticals, quasi-drugs, tobacco, cosmetics, oral care products, feeds and the like.
Beverages include, for example, carbonated beverages, fruit beverages, fruit-free beverages, vegetable beverages, favorite beverages, alcoholic beverages, non-alcoholic beverages, tea beverages, herbal teas, coffee beverages, functional beverages, sugarless beverages, sports beverages, nutrition.・ Nourishing drinks, dairy products, dairy products, lactic acid bacteria beverages, yogurt beverages, dairy beverages, soups, various instant beverages, etc.
食品としては、例えば、冷菓、和菓子類、洋菓子類、デザート類、アイスクリーム、シャーベット、焼き菓子、ベーカリー類、キャンデー類、チューイングガム、タブレット、グミ、油脂製品、マーガリン、コーヒーホワイトナー、チーズフード、ドレッシング、チョコレート類、調味料、味噌、醤油、ソース、マヨネーズ、農産加工品、麺、植物タンパク加工品、ジャム、ペースト、デザートソース、漬物、農産缶詰、果汁、果肉加工品、粉末スープ、レトルトパウチスープ、缶詰スープ、畜産加工品、ハム、ソーセージ、ハンバーグ、食肉缶詰、水産加工品、魚肉ハム、魚肉ソーセージ、水産練り製品、水産缶詰、冷凍食品、レトルト食品、インスタント食品、各種スナック食品類などが挙げられる。
Foods include, for example, cold confectionery, Japanese confectionery, Western confectionery, desserts, ice cream, sherbet, baked confectionery, bakery, candy, chewing gum, tablets, gummy, oil and fat products, margarine, coffee whitener, cheese food, dressing. , Chocolates, seasonings, miso, soy sauce, sauces, mayonnaise, processed agricultural products, noodles, processed vegetable protein products, jams, pastes, dessert sauces, pickles, canned agricultural products, fruit juices, processed fruit meat products, powdered soups, retort pouch soups , Canned soup, processed livestock products, ham, sausage, hamburger, canned meat, processed marine products, fish meat ham, fish sausage, fish paste products, canned fishery products, frozen foods, retort pouch foods, instant foods, various snack foods, etc. ..
医薬品としては、薬用化粧品、薬用ローション、錠剤、液状の薬、カプセルタイプの薬、顆粒状の薬、などが挙げられる。
Pharmaceuticals include medicated cosmetics, medicated lotions, tablets, liquid medicines, capsule-type medicines, granular medicines, and the like.
医薬部外品としては、サプリメント、薬用化粧品、薬用入浴剤、忌避剤などが挙げられる。
Examples of quasi-drugs include supplements, medicated cosmetics, medicated bath salts, and repellents.
たばことしては、加熱式たばこ、紙巻たばこ、葉巻、無煙たばこ、パイプ、キセル、水たばこ、電子たばこなどが挙げられる。
Examples of cigarettes include heat-not-burn tobacco, cigarettes, cigarettes, smokeless tobacco, pipes, xel, water tobacco, and electronic cigarettes.
香粧品としては、フレグランス製品、基礎化粧品、頭髪化粧品、仕上げ化粧品、トイレタリー製品、浴用剤、ボディケア製品、ヘアケア製品、洗浄剤、台所用洗剤、石鹸、柔軟仕上げ剤、芳香剤などが挙げられる。
Examples of cosmetics include fragrance products, basic cosmetics, hair cosmetics, finishing cosmetics, toiletry products, bathing agents, body care products, hair care products, cleaning agents, kitchen detergents, soaps, soft finishing agents, and air fresheners.
オーラルケア製品としては、洗口剤、歯磨き粉、練歯磨き、液体歯磨きオーラルケア用ガム、オーラルケア用キャンデー、マウススプレーなどが挙げられる。
Oral care products include mouthwashes, toothpastes, toothpastes, liquid toothpastes, oral care gums, oral care candy, and mouth sprays.
飼料としては、家畜用飼料、養魚用飼料、ペット用飼料などが挙げられる。
Examples of feed include livestock feed, fish feed, pet feed, and the like.
各種製品中の２－アセチル－１－ピロリンの含有量（質量基準）は、目的および用途に応じて適宜決定すればよく、特に限定されないが、通常０．０２ｐｐｔ～２０ｐｐｂの範囲が好ましく、０．２ｐｐｔ～２ｐｐｂの範囲がより好ましく、２ｐｐｔ～２００ｐｐｔの範囲がさらに好ましい。各種製品中の２－アセチル－１－ピロリンの含有量が上記の範囲になる量で、本発明の香料組成物を配合または賦香することが好ましい。
The content (mass basis) of 2-acetyl-1-pyrrolin in various products may be appropriately determined according to the purpose and application, and is not particularly limited, but is usually preferably in the range of 0.02 ppt to 20 ppb, and 0. The range of 2 ppt to 2 ppt is more preferable, and the range of 2 ppt to 200 ppt is even more preferable. It is preferable to blend or perfume the perfume composition of the present invention in an amount such that the content of 2-acetyl-1-pyrrolin in various products falls within the above range.
５）２－アセチル－１－ピロリンの安定化方法
２－アセチル－１－ピロリンは非常に不安定な化合物であるが、中鎖脂肪酸とグリセリンとのトリエステル（ＭＣＴ）およびトリアセチンからなる群より選ばれる１種または２種の食用油と混合することで、２－アセチル－１－ピロリンを安定化することができる。
すなわち、本発明は、２－アセチル－１－ピロリンを、中鎖脂肪酸とグリセリンとのトリエステル（ＭＣＴ）およびトリアセチンからなる群より選ばれる１種または２種の食用油と混合することを含む、２－アセチル－１－ピロリンの安定化方法をも包含するものである。
本発明の方法によれば、２－アセチル－１－ピロリンを長期間安定に存在させることが可能である。 5) Method for stabilizing 2-acetyl-1-pyrrolin Although 2-acetyl-1-pyrrolin is a very unstable compound, it is selected from the group consisting of triester (MCT) of medium-chain fatty acid and glycerin and triacetin. 2-Acetyl-1-pyrrolin can be stabilized by mixing with one or two edible oils.
That is, the present invention comprises mixing 2-acetyl-1-pyrrolin with one or two edible oils selected from the group consisting of triesters (MCTs) of medium chain fatty acids and glycerin and triacetin. It also includes methods for stabilizing 2-acetyl-1-pyrrolin.
According to the method of the present invention, 2-acetyl-1-pyrrolin can be stably present for a long period of time.
２－アセチル－１－ピロリンは非常に不安定な化合物であるが、中鎖脂肪酸とグリセリンとのトリエステル（ＭＣＴ）およびトリアセチンからなる群より選ばれる１種または２種の食用油と混合することで、２－アセチル－１－ピロリンを安定化することができる。
すなわち、本発明は、２－アセチル－１－ピロリンを、中鎖脂肪酸とグリセリンとのトリエステル（ＭＣＴ）およびトリアセチンからなる群より選ばれる１種または２種の食用油と混合することを含む、２－アセチル－１－ピロリンの安定化方法をも包含するものである。
本発明の方法によれば、２－アセチル－１－ピロリンを長期間安定に存在させることが可能である。 5) Method for stabilizing 2-acetyl-1-pyrrolin Although 2-acetyl-1-pyrrolin is a very unstable compound, it is selected from the group consisting of triester (MCT) of medium-chain fatty acid and glycerin and triacetin. 2-Acetyl-1-pyrrolin can be stabilized by mixing with one or two edible oils.
That is, the present invention comprises mixing 2-acetyl-1-pyrrolin with one or two edible oils selected from the group consisting of triesters (MCTs) of medium chain fatty acids and glycerin and triacetin. It also includes methods for stabilizing 2-acetyl-1-pyrrolin.
According to the method of the present invention, 2-acetyl-1-pyrrolin can be stably present for a long period of time.
本発明の好ましい態様によれば、３０℃暗所で、濃度（質量基準）１０ｐｐｍの２－アセチル－１－ピロリンを２ヶ月間保存したときの２－アセチル－１－ピロリンの残存率は６０％以上、より好ましくは７０％以上、さらに好ましくは８０％以上である。
According to a preferred embodiment of the present invention, the residual rate of 2-acetyl-1-pyrroline is 60% when 2-acetyl-1-pyrroline at a concentration (mass basis) of 10 ppm is stored for 2 months in a dark place at 30 ° C. As mentioned above, it is more preferably 70% or more, still more preferably 80% or more.
なお、２－アセチル－１－ピロリンの残存率は、保存開始時の２－アセチル－１－ピロリンの濃度に依存することが判明している。
It has been found that the residual rate of 2-acetyl-1-pyrrolin depends on the concentration of 2-acetyl-1-pyrrolin at the start of storage.
本発明の好ましい態様によれば、３０℃暗所で、濃度（質量基準）１ｐｐｍの２－アセチル－１－ピロリンを２ヶ月間保存したときの２－アセチル－１－ピロリンの残存率は６０％以上、より好ましくは７０％以上、さらに好ましくは８０％以上である。
According to a preferred embodiment of the present invention, the residual rate of 2-acetyl-1-pyrrolin when 2-acetyl-1-pyrrolin at a concentration (mass basis) of 1 ppm is stored for 2 months in a dark place at 30 ° C. is 60%. As mentioned above, it is more preferably 70% or more, still more preferably 80% or more.
また、本発明の好ましい態様によれば、３０℃暗所で、濃度（質量基準）１００ｐｐｍの２－アセチル－１－ピロリンを２ヶ月間保存したときの２－アセチル－１－ピロリンの残存率は６０％以上、より好ましくは７０％以上、さらに好ましくは８０％以上である。
Further, according to a preferred embodiment of the present invention, the residual rate of 2-acetyl-1-pyrrolin when 2-acetyl-1-pyrrolin at a concentration (mass basis) of 100 ppm is stored for 2 months in a dark place at 30 ° C. It is 60% or more, more preferably 70% or more, still more preferably 80% or more.
以下、実施例を挙げて本発明をさらに詳細に説明するが、本発明はこれらの実施例に何ら限定されるものではない。
Hereinafter, the present invention will be described in more detail with reference to examples, but the present invention is not limited to these examples.
〔実施例１〕
植物原料としてパンダンリーフ（市販品）１０ｇを使用し、ｐＨ７のリン酸緩衝液５０ｇを添加した。１時間室温で攪拌したのち、食用油としてＭＣＴ（トリ（カプリル・カプリン酸）グリセリル、炭素数Ｃ６：Ｃ８の比率が６：４のＭＣＴ）を添加し、３０分室温で攪拌しながら抽出をおこなった。得られたオイル層を植物抽出物とし、ガスクロマトグラフィーにて２－アセチル－１－ピロリンが含まれていることを確認した。 [Example 1]
10 g of Pandan leaf (commercially available) was used as a plant raw material, and 50 g of a phosphate buffer solution having a pH of 7 was added. After stirring at room temperature for 1 hour, MCT (tri (caprylic capric acid) glyceryl, MCT with a carbon number of C6: C8 ratio of 6: 4) was added as edible oil, and extraction was performed while stirring at room temperature for 30 minutes. It was. The obtained oil layer was used as a plant extract, and it was confirmed by gas chromatography that 2-acetyl-1-pyrrolin was contained.
植物原料としてパンダンリーフ（市販品）１０ｇを使用し、ｐＨ７のリン酸緩衝液５０ｇを添加した。１時間室温で攪拌したのち、食用油としてＭＣＴ（トリ（カプリル・カプリン酸）グリセリル、炭素数Ｃ６：Ｃ８の比率が６：４のＭＣＴ）を添加し、３０分室温で攪拌しながら抽出をおこなった。得られたオイル層を植物抽出物とし、ガスクロマトグラフィーにて２－アセチル－１－ピロリンが含まれていることを確認した。 [Example 1]
10 g of Pandan leaf (commercially available) was used as a plant raw material, and 50 g of a phosphate buffer solution having a pH of 7 was added. After stirring at room temperature for 1 hour, MCT (tri (caprylic capric acid) glyceryl, MCT with a carbon number of C6: C8 ratio of 6: 4) was added as edible oil, and extraction was performed while stirring at room temperature for 30 minutes. It was. The obtained oil layer was used as a plant extract, and it was confirmed by gas chromatography that 2-acetyl-1-pyrrolin was contained.
〔試験例１〕（官能評価）
エビフレーバー０．１ｇと粉末スープ１００ｇとを混合し、熱湯１００ｍＬを加えてよく混ぜ、海老のビスクを作製し、実施例１で得られた植物抽出物の添加の有無で比較および評価を行った。それぞれ８人のパネルが官能評価を行った。 [Test Example 1] (Sensory evaluation)
0.1 g of shrimp flavor and 100 g of powdered soup were mixed, 100 mL of boiling water was added and mixed well to prepare a bisque of shrimp, and comparison and evaluation were performed with and without addition of the plant extract obtained in Example 1. .. A panel of 8 people each performed a sensory evaluation.
エビフレーバー０．１ｇと粉末スープ１００ｇとを混合し、熱湯１００ｍＬを加えてよく混ぜ、海老のビスクを作製し、実施例１で得られた植物抽出物の添加の有無で比較および評価を行った。それぞれ８人のパネルが官能評価を行った。 [Test Example 1] (Sensory evaluation)
0.1 g of shrimp flavor and 100 g of powdered soup were mixed, 100 mL of boiling water was added and mixed well to prepare a bisque of shrimp, and comparison and evaluation were performed with and without addition of the plant extract obtained in Example 1. .. A panel of 8 people each performed a sensory evaluation.
表１に示した「ブランク品」および「実施例１植物抽出物添加品」を０．１質量％ずつ粉末スープ１００ｇに賦香し、熱湯１００ｍＬを加えてよく混ぜ、海老のビスクを作製して評価を行った。
なお、粉末スープの処方は表２に記載のとおりである。
Add 0.1% by mass of each of the "blank product" and "Example 1 plant extract additive" shown in Table 1 to 100 g of powdered soup, add 100 mL of boiling water and mix well to prepare a shrimp bisque. Evaluation was performed.
The prescription of the powdered soup is as shown in Table 2.
なお、粉末スープの処方は表２に記載のとおりである。
The prescription of the powdered soup is as shown in Table 2.
表３に示す４項目について各パネルが評価を行い、「ブランク品」、「実施例１植物抽出物添加品」を比較して優位性のあるものに１点、ないものに０点を加えた。以下は８人のパネルの合計点である。
Each panel evaluated the four items shown in Table 3, and compared "blank products" and "Example 1 plant extract additive products", and added 1 point to those with superiority and 0 points to those without. .. The following is the total score of the panel of 8 people.
実施例１植物抽出物添加品は、全体的な力価が強く、味の厚みを持ち上げる効果があることが分かった。また、海老の身の部分を想起させる香気を付与していることも分かった。
Example 1 It was found that the plant extract additive has a strong overall titer and has an effect of increasing the thickness of the taste. It was also found that it gives a scent reminiscent of the body of shrimp.
〔試験例２〕（保存安定性の評価１）
植物原料より２－アセチル－１－ピロリンを表５に記載の各食用油または水で抽出したものを、３０℃暗所で２週間および２ヶ月保存した際の２－アセチル－１－ピロリン含量をＧＣ－ＮＰＤ（ガスクロマトグラフィー－窒素リン検出器）を用いて分析した。
分析に用いた装置および条件は次のとおりである。
装置：Ａｇｉｌｅｎｔ ７８９０Ｂ ＧＣシステム（アジレントテクノロジー社製）
条件：試料導入部２００℃、試料検出部２５０℃、注入量０．５μＬ、スプリットレスモード [Test Example 2] (Evaluation of storage stability 1)
2-Acetyl-1-pyrrolin content extracted from plant raw materials with each of the cooking oils or waters shown in Table 5 and stored at 30 ° C. in the dark for 2 weeks and 2 months. Analysis was performed using GC-NPD (gas chromatography-nitrogen phosphorus detector).
The equipment and conditions used in the analysis are as follows.
Equipment: Agilent 7890B GC system (manufactured by Agilent Technologies)
Conditions: Sample introduction unit 200 ° C, sample detection unit 250 ° C, injection volume 0.5 μL, splitless mode
植物原料より２－アセチル－１－ピロリンを表５に記載の各食用油または水で抽出したものを、３０℃暗所で２週間および２ヶ月保存した際の２－アセチル－１－ピロリン含量をＧＣ－ＮＰＤ（ガスクロマトグラフィー－窒素リン検出器）を用いて分析した。
分析に用いた装置および条件は次のとおりである。
装置：Ａｇｉｌｅｎｔ ７８９０Ｂ ＧＣシステム（アジレントテクノロジー社製）
条件：試料導入部２００℃、試料検出部２５０℃、注入量０．５μＬ、スプリットレスモード [Test Example 2] (Evaluation of storage stability 1)
2-Acetyl-1-pyrrolin content extracted from plant raw materials with each of the cooking oils or waters shown in Table 5 and stored at 30 ° C. in the dark for 2 weeks and 2 months. Analysis was performed using GC-NPD (gas chromatography-nitrogen phosphorus detector).
The equipment and conditions used in the analysis are as follows.
Equipment: Agilent 7890B GC system (manufactured by Agilent Technologies)
Conditions: Sample introduction unit 200 ° C, sample detection unit 250 ° C, injection volume 0.5 μL, splitless mode
保存安定性試験開始時の２－アセチル－１－ピロリン濃度（質量基準）は１ｐｐｍまたは１０ｐｐｍとした。２－アセチル－１－ピロリンの残存率を以下の表５および６にそれぞれ示す。
The 2-acetyl-1-pyrrolin concentration (mass basis) at the start of the storage stability test was 1 ppm or 10 ppm. The residual rates of 2-acetyl-1-pyrrolin are shown in Tables 5 and 6 below, respectively.
〔試験例３〕（保存安定性の評価２）
合成品の２－アセチル－１－ピロリンを表７に記載の各食用油と混合し、３０℃暗所で２ヶ月保存した際の２－アセチル－１－ピロリン含量をＧＣ－ＮＰＤ（ガスクロマトグラフィー－窒素リン検出器）を用いて分析した。分析に用いた装置および条件は試験例２で述べたものと同じである。
保存安定性試験開始時の２－アセチル－１－ピロリン濃度（質量基準）は１００ｐｐｍとした。 [Test Example 3] (Evaluation of storage stability 2)
The content of 2-acetyl-1-pyrrolin when the synthetic product 2-acetyl-1-pyrrolin was mixed with each of the cooking oils shown in Table 7 and stored at 30 ° C. in the dark for 2 months was determined by GC-NPD (gas chromatography). -Analysis was performed using a nitrogen phosphorus detector). The equipment and conditions used for the analysis are the same as those described in Test Example 2.
The 2-acetyl-1-pyrrolin concentration (mass basis) at the start of the storage stability test was 100 ppm.
合成品の２－アセチル－１－ピロリンを表７に記載の各食用油と混合し、３０℃暗所で２ヶ月保存した際の２－アセチル－１－ピロリン含量をＧＣ－ＮＰＤ（ガスクロマトグラフィー－窒素リン検出器）を用いて分析した。分析に用いた装置および条件は試験例２で述べたものと同じである。
保存安定性試験開始時の２－アセチル－１－ピロリン濃度（質量基準）は１００ｐｐｍとした。 [Test Example 3] (Evaluation of storage stability 2)
The content of 2-acetyl-1-pyrrolin when the synthetic product 2-acetyl-1-pyrrolin was mixed with each of the cooking oils shown in Table 7 and stored at 30 ° C. in the dark for 2 months was determined by GC-NPD (gas chromatography). -Analysis was performed using a nitrogen phosphorus detector). The equipment and conditions used for the analysis are the same as those described in Test Example 2.
The 2-acetyl-1-pyrrolin concentration (mass basis) at the start of the storage stability test was 100 ppm.
上記の結果から、ＭＣＴおよびトリアセチン溶媒中において２－アセチル－１－ピロリンが安定であることが明らかとなった。
From the above results, it was clarified that 2-acetyl-1-pyrrolin was stable in MCT and triacetin solvents.
〔試験例４〕（保存安定性の評価３）
合成品の２－アセチル－１－ピロリンをＭＣＴ（実施例１で使用したものと同じものを使用）またはトリアセチンと混合し、３０℃暗所で４ヶ月から１３ヶ月保存した際の２－アセチル－１－ピロリン含量をＧＣ－ＮＰＤ（ガスクロマトグラフィー－窒素リン検出器）を用いて分析した。分析に用いた装置および条件は試験例２で述べたものと同じである。
保存安定性試験開始時の２－アセチル－１－ピロリン濃度（質量基準）は１０ｐｐｍとした。 [Test Example 4] (Evaluation of storage stability 3)
2-Acetyl-1-pyrroline, a synthetic product, mixed with MCT (the same one used in Example 1) or triacetin and stored at 30 ° C. in the dark for 4 to 13 months. The 1-pyrroline content was analyzed using GC-NPD (Gas Chromatography-Nitrogen Phosphorus Detector). The equipment and conditions used for the analysis are the same as those described in Test Example 2.
The 2-acetyl-1-pyrrolin concentration (mass basis) at the start of the storage stability test was 10 ppm.
合成品の２－アセチル－１－ピロリンをＭＣＴ（実施例１で使用したものと同じものを使用）またはトリアセチンと混合し、３０℃暗所で４ヶ月から１３ヶ月保存した際の２－アセチル－１－ピロリン含量をＧＣ－ＮＰＤ（ガスクロマトグラフィー－窒素リン検出器）を用いて分析した。分析に用いた装置および条件は試験例２で述べたものと同じである。
保存安定性試験開始時の２－アセチル－１－ピロリン濃度（質量基準）は１０ｐｐｍとした。 [Test Example 4] (Evaluation of storage stability 3)
2-Acetyl-1-pyrroline, a synthetic product, mixed with MCT (the same one used in Example 1) or triacetin and stored at 30 ° C. in the dark for 4 to 13 months. The 1-pyrroline content was analyzed using GC-NPD (Gas Chromatography-Nitrogen Phosphorus Detector). The equipment and conditions used for the analysis are the same as those described in Test Example 2.
The 2-acetyl-1-pyrrolin concentration (mass basis) at the start of the storage stability test was 10 ppm.
上記の結果から、ＭＣＴ溶媒中において２－アセチル－１－ピロリンが１年間以上安定であることが明らかとなった。
From the above results, it was clarified that 2-acetyl-1-pyrrolin was stable in the MCT solvent for 1 year or more.
〔試験例５〕（保存安定性の評価４）
合成品の２－アセチル－１－ピロリンをアルコール（エタノール、メタノールまたはグリセリン）と混合し、３０℃暗所で２週間保存した際の２－アセチル－１－ピロリン含量をＧＣ－ＮＰＤ（ガスクロマトグラフィー－窒素リン検出器を用いて分析した。分析に用いた装置および条件は試験例２で述べたものと同じである。保存安定性試験開始時の２－アセチル－１－ピロリン濃度（質量基準）は１ｐｐｍ、１０ｐｐｍまたは１００ｐｐｍとなるよう調整した。２－アセチル－１－ピロリンの残存率を以下の表９、１０および１１にそれぞれ示す。 [Test Example 5] (Evaluation of storage stability 4)
The 2-acetyl-1-pyrrolin content of the synthetic product when mixed with alcohol (ethanol, methanol or glycerin) and stored in the dark at 30 ° C for 2 weeks is determined by GC-NPD (gas chromatography). -Analysis was performed using a nitrogen phosphorus detector. The equipment and conditions used for the analysis were the same as those described in Test Example 2. 2-Acetyl-1-pyrrolin concentration (mass basis) at the start of the storage stability test. Was adjusted to 1 ppm, 10 ppm or 100 ppm. The residual rates of 2-acetyl-1-pyrrolin are shown in Tables 9, 10 and 11 below, respectively.
合成品の２－アセチル－１－ピロリンをアルコール（エタノール、メタノールまたはグリセリン）と混合し、３０℃暗所で２週間保存した際の２－アセチル－１－ピロリン含量をＧＣ－ＮＰＤ（ガスクロマトグラフィー－窒素リン検出器を用いて分析した。分析に用いた装置および条件は試験例２で述べたものと同じである。保存安定性試験開始時の２－アセチル－１－ピロリン濃度（質量基準）は１ｐｐｍ、１０ｐｐｍまたは１００ｐｐｍとなるよう調整した。２－アセチル－１－ピロリンの残存率を以下の表９、１０および１１にそれぞれ示す。 [Test Example 5] (Evaluation of storage stability 4)
The 2-acetyl-1-pyrrolin content of the synthetic product when mixed with alcohol (ethanol, methanol or glycerin) and stored in the dark at 30 ° C for 2 weeks is determined by GC-NPD (gas chromatography). -Analysis was performed using a nitrogen phosphorus detector. The equipment and conditions used for the analysis were the same as those described in Test Example 2. 2-Acetyl-1-pyrrolin concentration (mass basis) at the start of the storage stability test. Was adjusted to 1 ppm, 10 ppm or 100 ppm. The residual rates of 2-acetyl-1-pyrrolin are shown in Tables 9, 10 and 11 below, respectively.
上記の結果から、アルコール溶媒中において２－アセチル－１－ピロリンの安定性は、２－アセチル－１－ピロリンの濃度に依存し、２－アセチル－１－ピロリン濃度が１００ｐｐｍの場合に保存安定性が低下することが明らかになった。
アルコール溶媒は、水と混ざりやすいため、水を含む場合に脱水処理することができない。試験例２の結果より、水を含む場合に２－アセチル－１－ピロリンの安定性が低下することが判明していることから、長期間保存した場合、２－アセチル－１－ピロリンの安定性はさらに低下することが予想される。
また、アルコール溶媒は水と分離しないため、水蒸気蒸留後の留液や植物体の水抽出液に対して溶媒抽出を行うことができない。抽出工程の前に、水蒸気蒸留、水抽出または温水抽出によって前記植物原料を処理する前処理工程を行う場合でも、前処理液である水系溶液からの抽出ができるという点においてＭＣＴ等の食用油は優位性があると考えられる。
From the above results, the stability of 2-acetyl-1-pyrrolin in an alcohol solvent depends on the concentration of 2-acetyl-1-pyrrolin, and the storage stability when the concentration of 2-acetyl-1-pyrrolin is 100 ppm. Was found to decrease.
Since the alcohol solvent is easily mixed with water, it cannot be dehydrated when it contains water. From the results of Test Example 2, it has been found that the stability of 2-acetyl-1-pyrrolin decreases when it contains water. Therefore, the stability of 2-acetyl-1-pyrrolin when stored for a long period of time. Is expected to decline further.
In addition, since the alcohol solvent does not separate from water, it is not possible to extract the solvent from the distillate after steam distillation or the water extract of the plant. Even when the pretreatment step of treating the plant raw material by steam distillation, water extraction or warm water extraction is performed before the extraction step, edible oils such as MCT can be extracted from the aqueous solution which is the pretreatment liquid. It is considered to have an advantage.
アルコール溶媒は、水と混ざりやすいため、水を含む場合に脱水処理することができない。試験例２の結果より、水を含む場合に２－アセチル－１－ピロリンの安定性が低下することが判明していることから、長期間保存した場合、２－アセチル－１－ピロリンの安定性はさらに低下することが予想される。
また、アルコール溶媒は水と分離しないため、水蒸気蒸留後の留液や植物体の水抽出液に対して溶媒抽出を行うことができない。抽出工程の前に、水蒸気蒸留、水抽出または温水抽出によって前記植物原料を処理する前処理工程を行う場合でも、前処理液である水系溶液からの抽出ができるという点においてＭＣＴ等の食用油は優位性があると考えられる。
From the above results, the stability of 2-acetyl-1-pyrrolin in an alcohol solvent depends on the concentration of 2-acetyl-1-pyrrolin, and the storage stability when the concentration of 2-acetyl-1-pyrrolin is 100 ppm. Was found to decrease.
Since the alcohol solvent is easily mixed with water, it cannot be dehydrated when it contains water. From the results of Test Example 2, it has been found that the stability of 2-acetyl-1-pyrrolin decreases when it contains water. Therefore, the stability of 2-acetyl-1-pyrrolin when stored for a long period of time. Is expected to decline further.
In addition, since the alcohol solvent does not separate from water, it is not possible to extract the solvent from the distillate after steam distillation or the water extract of the plant. Even when the pretreatment step of treating the plant raw material by steam distillation, water extraction or warm water extraction is performed before the extraction step, edible oils such as MCT can be extracted from the aqueous solution which is the pretreatment liquid. It is considered to have an advantage.
Claims (12)
- ２－アセチル－１－ピロリンを含む植物抽出物の製造方法であって、
２－アセチル－１－ピロリンを含む植物原料を中鎖脂肪酸とグリセリンとのトリエステル（ＭＣＴ）およびトリアセチンからなる群より選ばれる１種または２種の食用油で抽出する抽出工程を含む、前記植物抽出物の製造方法。 A method for producing a plant extract containing 2-acetyl-1-pyrrolin.
The plant comprising an extraction step of extracting a plant material containing 2-acetyl-1-pyrrolin with one or two edible oils selected from the group consisting of triesters (MCTs) of medium chain fatty acids and glycerin and triacetin. How to make an extract. - 前記抽出工程の前に、水蒸気蒸留、水抽出または温水抽出によって前記植物原料を処理する前処理工程を含む、請求項１に記載の製造方法。 The production method according to claim 1, further comprising a pretreatment step of treating the plant raw material by steam distillation, water extraction or hot water extraction before the extraction step.
- 前記抽出工程で得られた抽出物を脱水および濾過する後処理工程を含む、請求項１または２に記載の製造方法。 The production method according to claim 1 or 2, which comprises a post-treatment step of dehydrating and filtering the extract obtained in the extraction step.
- 前記植物原料が、パンダンリーフ、ダダチャ豆、香り米およびトウモロコシからなる群より選ばれる１種以上である、請求項１から３のいずれか一項に記載の製造方法。 The production method according to any one of claims 1 to 3, wherein the plant raw material is at least one selected from the group consisting of pandan leaf, dadacha beans, aromatic rice and corn.
- 請求項１から４のいずれか一項に記載の製造方法で製造された植物抽出物であって、２－アセチル－１－ピロリンを１ｐｐｂ～１０００ｐｐｍ含む、植物抽出物。 A plant extract produced by the production method according to any one of claims 1 to 4, which contains 1 ppb to 1000 ppm of 2-acetyl-1-pyrrolin.
- ３０℃暗所で、濃度１０ｐｐｍの２－アセチル－１－ピロリンを２ヶ月間保存したときの２－アセチル－１－ピロリンの残存率が６０％以上である、請求項５に記載の植物抽出物。 The plant extract according to claim 5, wherein the residual rate of 2-acetyl-1-pyrrolin is 60% or more when 2-acetyl-1-pyrrolin at a concentration of 10 ppm is stored for 2 months in a dark place at 30 ° C. ..
- ２－アセチル－１－ピロリン、および
中鎖脂肪酸とグリセリンとのトリエステル（ＭＣＴ）およびトリアセチンからなる群より選ばれる１種または２種の食用油
を含む組成物。 A composition comprising 2-acetyl-1-pyrroline, and one or two edible oils selected from the group consisting of triesters (MCTs) of medium-chain fatty acids and glycerin and triacetin. - 請求項５または６に記載の植物抽出物、または請求項７に記載の組成物を含む香料組成物。 A fragrance composition containing the plant extract according to claim 5 or 6, or the composition according to claim 7.
- ２－アセチル－１－ピロリンを０．０１ｐｐｂ～１０００ｐｐｍ含む、請求項８に記載の香料組成物。 The fragrance composition according to claim 8, which contains 0.01 ppb to 1000 ppm of 2-acetyl-1-pyrrolin.
- 請求項８または９に記載の香料組成物を含む、飲料、食品、医薬品、医薬部外品、たばこ、香粧品、オーラルケア製品および飼料からなる群より選ばれる製品。 A product selected from the group consisting of beverages, foods, pharmaceuticals, quasi-drugs, tobacco, cosmetics, oral care products and feeds, which comprises the perfume composition according to claim 8 or 9.
- ２－アセチル－１－ピロリンを、中鎖脂肪酸とグリセリンとのトリエステル（ＭＣＴ）およびトリアセチンからなる群より選ばれる１種または２種の食用油と混合することを含む、２－アセチル－１－ピロリンの安定化方法。 2-Acetyl-1-pyrroline comprises mixing 2-acetyl-1-pyrrolin with one or two edible oils selected from the group consisting of triesters (MCTs) of medium chain fatty acids and glycerin and triacetin. How to stabilize pyrrolin.
- ３０℃暗所で、濃度１０ｐｐｍの２－アセチル－１－ピロリンを２ヶ月間保存したときの２－アセチル－１－ピロリンの残存率が６０％以上である、請求項１１に記載の安定化方法。
The stabilization method according to claim 11, wherein the residual rate of 2-acetyl-1-pyrrolin is 60% or more when 2-acetyl-1-pyrrolin at a concentration of 10 ppm is stored for 2 months in a dark place at 30 ° C. ..
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