WO2014054705A1 - エビフレーバー組成物及びエビ風味増強剤 - Google Patents
エビフレーバー組成物及びエビ風味増強剤 Download PDFInfo
- Publication number
- WO2014054705A1 WO2014054705A1 PCT/JP2013/076858 JP2013076858W WO2014054705A1 WO 2014054705 A1 WO2014054705 A1 WO 2014054705A1 JP 2013076858 W JP2013076858 W JP 2013076858W WO 2014054705 A1 WO2014054705 A1 WO 2014054705A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- shrimp
- flavor
- shrimp flavor
- octadien
- food
- Prior art date
Links
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- 229930006696 sabinene Natural products 0.000 description 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
- 235000014102 seafood Nutrition 0.000 description 1
- 230000035807 sensation Effects 0.000 description 1
- 235000019615 sensations Nutrition 0.000 description 1
- 235000015170 shellfish Nutrition 0.000 description 1
- 235000011888 snacks Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- BATOPAZDIZEVQF-UHFFFAOYSA-N sorbic aldehyde Natural products CC=CC=CC=O BATOPAZDIZEVQF-UHFFFAOYSA-N 0.000 description 1
- 235000019721 spearmint oil Nutrition 0.000 description 1
- 229940116411 terpineol Drugs 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- FACAUSJJVBMWLV-JXMROGBWSA-N thiogeraniol Chemical compound CC(C)=CCC\C(C)=C\CS FACAUSJJVBMWLV-JXMROGBWSA-N 0.000 description 1
- 229960000790 thymol Drugs 0.000 description 1
- WXBXVVIUZANZAU-CMDGGOBGSA-N trans-2-decenoic acid Chemical compound CCCCCCC\C=C\C(O)=O WXBXVVIUZANZAU-CMDGGOBGSA-N 0.000 description 1
- MBDOYVRWFFCFHM-UHFFFAOYSA-N trans-2-hexenal Natural products CCCC=CC=O MBDOYVRWFFCFHM-UHFFFAOYSA-N 0.000 description 1
- NPFVOOAXDOBMCE-UHFFFAOYSA-N trans-3-hexenyl acetate Natural products CCC=CCCOC(C)=O NPFVOOAXDOBMCE-UHFFFAOYSA-N 0.000 description 1
- HRHOWZHRCRZVCU-UHFFFAOYSA-N trans-hex-2-enyl acetate Natural products CCCC=CCOC(C)=O HRHOWZHRCRZVCU-UHFFFAOYSA-N 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- WKSPQBFDRTUGEF-UHFFFAOYSA-N tridec-2-enenitrile Chemical compound CCCCCCCCCCC=CC#N WKSPQBFDRTUGEF-UHFFFAOYSA-N 0.000 description 1
- 239000001069 triethyl citrate Substances 0.000 description 1
- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 1
- 235000013769 triethyl citrate Nutrition 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- 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
-
- 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
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/202—Aliphatic compounds
- A23L27/2024—Aliphatic compounds having oxygen as the only hetero atom
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/202—Aliphatic compounds
- A23L27/2024—Aliphatic compounds having oxygen as the only hetero atom
- A23L27/2026—Hydroxy compounds
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
Definitions
- the present invention relates to a shrimp flavor composition containing 1,5-octadien-3-one and / or 1,5-octadien-3-ol, and a food or drink or seasoning containing the shrimp flavor composition
- the present invention relates to a shrimp flavor enhancer comprising 1,5-octadien-3-one and / or 1,5-octadien-3-ol, and a food or drink or a seasoning containing the shrimp flavor enhancer.
- a raw material of the shrimp flavor composition for example, (1) crustacean extract, (2) crustacean oleoresin, (3) seeding oil, (4) supercritical carbon dioxide extract of crustacean, (5 ) Fractionated fragrances, (6) synthetic fragrances, and the like, and a shrimp flavor composition can be obtained by appropriately combining one or more of these depending on the application (Non-patent Document 1).
- the flavor characteristics required for the shrimp flavor composition are required to have a flavor characteristic reminiscent of a natural flavor unique to shrimp, a boiled feeling or a roasted feeling that harmonizes with cooking.
- Patent Document 1 as a stronger and more preferred crustacean flavor composition, (A) hydrocarbons, (B) alcohols, (C) phenols, (D) aldehydes, (E) ketones, ( F) Esters, (G) lactones, (H) carboxylic acids, (I) furan compounds, (J) nitrogen-containing compounds, (K) sulfur-containing compounds, (L) natural fragrances, A crustacean flavor composition characterized by appropriately mixing at least one material selected from the group consisting of (A) to (L), preferably two or more materials, and amino acids is proposed. Yes.
- Aroma analysis is usually performed by gas chromatography, and the analysis values are generally arranged in the order of the time during which the aroma can be retained (hereinafter, sometimes simply referred to as “retention time”), or grouped for each functional group. Shown. Therefore, a blender who refers to fragrance analysis data often selects various synthetic fragrances with reference to the retention time or selects each functional group to start blending.
- 1,5-octadien-3-one is a known compound contained in beef and the like, and is known as a compound having a metallic odor or a geranium odor (Non-Patent Documents 2 to 6).
- 1,5-octadien-3-ol is a known compound contained in roast chicken, cauliflower, etc., and is known as a compound having a fragrance pronounced of wood or geranium (Non-patent Documents 7 and 8). It has been.
- the shrimp flavor composition prepared by directly reproducing the quantitative analysis data of the aroma component can be used as a composition having the target shrimp flavor, and usually a satisfactory flavor (flavor) cannot be obtained. It was.
- a commonly used synthetic fragrance-based shrimp flavor is an image flavor in which a specific aroma component of shrimp is found by aroma analysis, and its characteristic aroma is emphasized and deformed. That is, by using the shrimp flavor composition together with the color and taste in the final product relating to shrimp, the target shrimp can be recognized, and the preferred shrimp flavor could not be reproduced only by the flavor.
- crustacean extract in order to prepare a preferred shrimp flavor composition, (1) crustacean extract, (2) crustacean oleoresin, (3) seeding oil, (4) crustacean supercritical carbon dioxide gas It was often composed of materials mainly composed of extracts, (5) fractionated fragrances, (6) synthetic fragrances, etc., but those made of these materials are stronger and more preferable because their titers are not high. In the preparation of a composition for obtaining shrimp flavor, a new material is desired and there is room for improvement.
- a first object of the present invention is to provide a shrimp flavor composition and a shrimp flavor enhancer that can provide a more preferable shrimp flavor. Also, providing various foods and drinks and seasonings using the composition or enhancer, imparting shrimp flavor to foods and drinks and seasonings using the composition or enhancer, or enhancing the like.
- the “preferable shrimp flavor” in the present specification means the flavor of soup that occurs when the shrimp is boiled or the flavor that occurs when it is sauteed (boiled feeling), and the flavor of fried shrimp that occurs when the shrimp is fried in oil Sensation) and flavor characteristics (shrimp flavor) reminiscent of the baked shrimp flavor (roasted feeling) produced when baked shrimp are baked.
- the present inventors have obtained a shrimp flavor composition obtained by mixing 1,5-octadien-3-one and / or 1,5-octadien-3-ol. Surprisingly, it has been found that it has a shrimp flavor with a strong flavor and richness and an excellent roasted feeling, and the present invention has been completed.
- the present invention relates to the following [1] to [12].
- [1] A shrimp flavor composition containing at least one of 1,5-octadien-3-one and 1,5-octadien-3-ol.
- [2] The shrimp flavor composition according to the above [1], which has a shrimp flavor selected from a boiled flavor, a fried flavor, or a roasted flavor.
- [3] The above [1] or [2], wherein the total content of the 1,5-octadien-3-one and the 1,5-octadien-3-ol is 0.001 ppm to 1000 ppm on a mass basis Shrimp flavor composition.
- [4] A food or drink or seasoning containing the shrimp flavor composition according to any one of [1] to [3].
- [5] A method of imparting shrimp flavor to a food or drink or seasoning by adding the shrimp flavor composition according to any one of [1] to [3].
- [6] A method for enhancing the shrimp flavor of a food or drink or seasoning by adding the shrimp flavor composition according to any one of [1] to [3].
- [7] A shrimp flavor enhancer comprising at least one of 1,5-octadien-3-one and 1,5-octadien-3-ol.
- the shrimp flavor enhancer according to the above [7] which enhances a shrimp flavor selected from a boiled flavor, a fried flavor, or a roasted flavor.
- [9] A food or drink or seasoning containing the shrimp flavor enhancer according to [7] or [8].
- 1,5-octadien-3-one and / or 1,5-octadien-3-ol which is useful as a flavor enhancer for various foods and beverages and seasonings, is mixed with the shrimp flavor composition.
- the shrimp flavor composition which has the outstanding shrimp flavor with a boiled feeling, a fry feeling, and a roast feeling can be provided.
- mass% “mass part” and “weight%”, and “part by weight” are synonymous with each other, and simply described as “%”, “ppm”, and “ppb”, “Wt%”, “wt ppm” and “wt ppb” are shown respectively.
- the shrimp flavor composition according to the present invention contains at least one of 1,5-octadien-3-one and 1,5-octadien-3-ol. On and 1,5-octadien-3-ol will be described. Since 1,5-octadien-3-one has cis-trans by substitution to a double bond in the molecule, there are two geometric isomers, (5E) -form and (5Z) -form . Specifically, there are two types, (5E) -1,5-octadien-3-one and (5Z) -1,5-octadien-3-one.
- 1,5-octadien-3-ol has one asymmetric carbon in the molecule
- (3S) -form and (3R) -form and further substitution to a double bond
- These 1,5-octadien-3-one and 1,5-octadien-3-ol are both oily (liquid) at room temperature.
- any isomer of 1,5-octadien-3-one and 1,5-octadien-3-ol can be used, or a mixture thereof may be used. These isomers can be distinguished by the retention time of gas chromatography. In the present specification, these isomers are collectively referred to as “1,5-octadien-3-one” or “1,5-octadien-3-ol” without distinction.
- 1,5-octadien-3-one and / or 1,5-octadien-3-ol may be obtained by extraction from natural products, or may be obtained by chemical synthesis (for example, , Synthesized by the method described in Non-Patent Document 6). Moreover, you may use together the thing obtained from the natural product, and the thing obtained by chemical synthesis. In the case of chemical synthesis, a large amount of 1,5-octadien-3-one and / or 1,5-octadien-3-ol having a high purity can be obtained.
- the total content of 1,5-octadien-3-one and 1,5-octadien-3-ol in the shrimp flavor composition of the present invention is preferably 0.001 ppm to 1000 ppm, more preferably 0.01 ppm. -100 ppm, more preferably 0.1 ppm to 10 ppm.
- the content is 0.001 ppm or more, the effects of the present invention can be sufficiently exerted, and when the content is 1000 ppm or less, the fragrance is preferable as a shrimp flavor.
- the shrimp flavor composition of the present invention can also contain other aroma components.
- Other aromatic components include, for example, hydrocarbons such as limonene, osymene, ⁇ -pinene, ⁇ -pinene, ⁇ -terpinene, sabinene, myrcene; linalool, citronellol, dihydrolinalool, tetrahydromegol, myrsenol, dihydromyrsenol , Tetrahydromyrsenol, osmenol, terpineol, 3-tanol, benzyl alcohol, ⁇ -phenylethyl alcohol, ⁇ -phenylethyl alcohol, cis-3-hexenol, and the like; acetaldehyde, n-hexanal, n-heptanal, n -Octanal, n-nonal, cis-3-hexenal, cis-6-nonen
- Phenols Lactones such as ⁇ -undecalactone and ⁇ -dodecalactone; Fatty acids such as acetic acid, propionic acid, butyric acid, valeric acid, hexanoic acid, octanoic acid, decanoic acid, dodecanoic acid, 2-decenoic acid, and gellanic acid Sulfides such as diallyl sulfide, diallyl disulfide, dipropyl disulfide, methylpropyl disulfide, allylpropyl disulfide, diallyl trisulfide; methyl anthranilate, ethyl anthranilate, N-methylanthra Methyl oxalate, methyl N-2'-methylpentylidene anthranilate, ligantoral, dodecanenitrile, 2-tridecenenitrile, geranylnitrile, citronellylnitrile, 3,7-
- the total content of 1,5-octadien-3-one and 1,5-octadien-3-ol and other aroma components are in a mass ratio of 1: 9 to It is preferable that it is 1: 99.9 from the point which increases shrimp flavor.
- Components other than the fragrance component that can be blended in the shrimp flavor composition of the present invention include a solvent suitable for dissolving the fragrance component.
- a solvent suitable for dissolving the fragrance component For example, water, ethyl alcohol, glycerin, propylene glycol, triacetin, medium chain fatty acid glycerin ester, edible fats and oils such as edible vegetable oil, natural pigments usable in food and drink, vitamins, vegetable resins, etc. .
- These are preferably contained in an amount of 0 to 99% by mass based on the shrimp flavor composition from the viewpoint of easy handling of the composition.
- emulsified using various emulsifiers that can be used for foods and beverages by adding excipients such as lactose, dextrin, gum arabic, and cyclodextrin to the shrimp flavor composition liquefied using the solvent.
- excipients such as lactose, dextrin, gum arabic, and cyclodextrin
- a composition in an arbitrary dosage form such as paste, granule, or microcapsule can be prepared and used according to the purpose of use.
- the shrimp flavor composition according to the present invention preferably has a shrimp flavor selected from a boiled flavor, a fried flavor or a roasted flavor.
- a shrimp flavor can be imparted to a food or drink or seasoning. That is, even if the food / beverage product or the seasoning product has no shrimp flavor, the food / beverage product provided with the shrimp flavor can be easily produced. Moreover, if the shrimp flavor composition which concerns on this invention is added to the food / beverage products or seasoning which originally had shrimp flavor, the food / beverage products or seasoning product which the said shrimp flavor enhanced can also be obtained.
- the blending amount of the shrimp flavor composition of the present invention into the shrimp flavored food and drink or shrimp flavored seasoning varies depending on the purpose or the kind of the shrimp flavor enhancer, the intensity of the scent, etc., for example, 0.001%
- a concentration range of ⁇ 10%, preferably 0.01 ⁇ 3% can be mentioned.
- the present invention can also provide a shrimp flavor enhancer comprising 1,5-octadien-3-one and / or 1,5-octadien-3-ol.
- the flavor enhanced by the enhancer is preferably a shrimp flavor selected from a boiled flavor, a fried flavor or a roasted flavor.
- 1,5-octadien-3-one and / or 1,5-octadien-3-ol may be used alone or in combination of two or more of the aforementioned geometric isomers.
- the total amount of 1,5-octadien-3-one and 1,5-octadien-3-ol in the shrimp flavored food and drink or shrimp flavored seasoning of the shrimp flavor enhancer of the present invention is the purpose or Although depending on the kind of the shrimp flavor enhancer, for example, a concentration range of 0.0001 ppb to 10 ppm, preferably 0.001 ppb to 1 ppm, more preferably 0.01 ppb to 0.1 ppm can be mentioned.
- the total content of 1,5-octadien-3-one and 1,5-octadien-3-ol in the shrimp flavor enhancer is 0.001 ppm to 1000 ppm, so that the effects of the present invention can be sufficiently exerted. It is preferable because it provides a good fragrance as a shrimp flavor.
- the shrimp flavor composition of the present invention can be added to shrimp flavored foods and beverages and shrimp flavored seasonings to enhance those shrimp flavors, and has no shrimp flavor, added to various foods and beverages and seasonings By doing, the food-drinks and seasoning to which the shrimp flavor was provided can be manufactured easily.
- the present invention will be specifically described with reference to examples. However, the present invention is not limited to these examples, and various changes and modifications are made without departing from the scope of the present invention. Also good.
- the unit of the prescription described below shall represent a mass ratio.
- Example 1 Shrimp flavor enhancer As Example 1, a 0.1% aqueous solution of 1,5-octadien-3-one was prepared to prepare a shrimp flavor enhancer.
- 1,5-octadien-3-one is (5Z) -1,5-octadien-3-one, which was obtained by the synthesis method described in Non-Patent Document 6.
- Example 2 Shrimp flavor enhancer As Example 2, a 0.1% aqueous solution of 1,5-octadien-3-one was prepared to prepare a shrimp flavor enhancer.
- 1,5-octadien-3-ol is (5Z) -1,5-octadien-3-ol, which was obtained by the synthesis method described in Non-Patent Document 6.
- the product of the present invention 1, the product of the present invention 2 and the comparative product 1 were each diluted 20 times with rapeseed oil, and as a result of sensory evaluation of the flavor by 10 specialist panelists, all the panelists compared the product of the present invention with that of the comparative product 1. It was confirmed that No. 1 and the product of the present invention 2 had an enhanced top impact, gave an impression of a clear outline, and had a shrimp-flavoring rich in sustainability.
- Test Examples 1-1 to 1-8 Effect test of 1,5-octadien-3-one with shrimp flavored oil
- 1,5-octadien-3-one had the concentrations shown in Table 2.
- an aqueous solution of 1,5-octadien-3-one was prepared, and the shrimp flavor enhancers in Test Examples 1-1 to 1-8 were prepared.
- the shrimp flavor enhancer prepared in place of the “shrimp flavor enhancer of Example 1” in Example 3 the shrimp flavor compositions in Test Examples 1-1 to 1-8 were prepared.
- the shrimp-flavored oils of Test Examples 1-1 to 1-8 were each diluted 20-fold with rapeseed oil, and the flavor was subjected to a sensory evaluation by 10 professional panelists. As a result, all of the panelists conducted Test Examples 1-2 to 1-7. It was recognized that the shrimp-flavored oil had a remarkably round and rich taste, was harmonious, and had a long-lasting shrimp flavor. In particular, the shrimp flavored oils of Test Examples 1-4 to 1-6 were found to have a preferable shrimp flavor. On the other hand, the shrimp flavor oil of Test Example 1-1 did not fully exhibit the shrimp flavor, and the shrimp flavor oil of Test Example 1-8 had an aroma different from the shrimp flavor. It was recognized as undesirable.
- Test Examples 2-1 to 2-8) Effect test of 1,5-octadien-3-ol with shrimp flavor oil
- concentration of 1,5-octadien-3-ol shown in Table 3 was the same as in Example 2.
- an aqueous solution of 1,5-octadien-3-ol was prepared, and the shrimp flavor enhancers in Test Examples 2-1 to 2-8 were prepared.
- shrimp flavor enhancers in Test Examples 2-1 to 2-8 were prepared using the shrimp flavor enhancers prepared in place of the “shrimp flavor enhancer of Example 2” in Example 4.
- the shrimp-flavored oils of Test Examples 2-1 to 2-8 were each diluted 20-fold with rapeseed oil, and the flavor was sensory-evaluated by 10 expert panelists. As a result, all panelists conducted Test Examples 2-2 to 2-7. It was recognized that the shrimp-flavored oil had a remarkably round and rich taste, was harmonious, and had a long-lasting shrimp flavor. In particular, the shrimp flavored oils of Test Examples 2-4 to 2-6 were found to have a preferable shrimp flavor. On the other hand, the shrimp flavor oil of Test Example 2-1 did not fully exhibit the shrimp flavor, and the shrimp flavor oil of Test Example 2-8 had a different fragrance from the shrimp flavor. It was recognized as undesirable.
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- Life Sciences & Earth Sciences (AREA)
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Abstract
Description
エビフレーバー組成物に要求されるフレーバー特性としては、エビ特有の自然な風味や、料理に調和した食欲をそそるボイル感やロースト感等を想起させるような香味特性が求められている。
香気分析は通常ガスクロマトグラフィーにて行い、その分析値は一般に香気を保持可能な時間(以下、単に「保持時間」と称することもある。)の順に並べられるか、或いは官能基ごとにまとめられて示される。そのため、香気分析データを参考にする調合者は、各種合成香料を、保持時間を参考に選択するか、或いは官能基ごとに選択して調合を始めることが多い。
一般に用いられている合成香料系のエビフレーバーは、香気分析によりエビの特異的香気成分を見つけだし、その特徴的香気を強調・デフォルメしたイメージフレーバーである。すなわち、エビに関する最終製品における色彩、呈味とともにエビフレーバー組成物を用いることにより、目的とするエビを認知させられるものであり、そのフレーバーだけで好ましいエビ風味を再現することはできなかった。
なお、本明細書における「好ましいエビフレーバー」とは、エビ類を煮込んだ時に生じるスープの風味或いはソテーした時に生じる風味(ボイル感)、エビ類を油で揚げた時に生じるフライドシュリンプの風味(フライ感)、エビ類を焼いた時に生じる焼いたエビの風味(ロースト感)等を想起させるような香味特性(エビフレーバー)がより好ましいことを意味する。
[1] 1,5-オクタジエン-3-オン及び1,5-オクタジエン-3-オールの少なくともいずれか一方を含有するエビフレーバー組成物。
[2] ボイル風味、フライ風味又はロースト風味から選ばれるエビ風味を有する、前記[1]記載のエビフレーバー組成物。
[3] 前記1,5-オクタジエン-3-オン及び前記1,5-オクタジエン-3-オールの含有量の合計が質量基準で0.001ppm~1000ppmである、前記[1]又は[2]記載のエビフレーバー組成物。
[4] 前記[1]~[3]のいずれか一に記載のエビフレーバー組成物を含有する飲食品又は調味料。
[5] 前記[1]~[3]のいずれか一に記載のエビフレーバー組成物を添加することにより、飲食品又は調味料にエビ風味を付与する方法。
[6] 前記[1]~[3]のいずれか一に記載のエビフレーバー組成物を添加することにより、飲食品又は調味料のエビ風味を増強する方法。
[7] 1,5-オクタジエン-3-オン及び1,5-オクタジエン-3-オールの少なくともいずれか一方からなるエビ風味増強剤。
[8] ボイル風味、フライ風味又はロースト風味から選ばれるエビ風味を増強する、前記[7]記載のエビ風味増強剤。
[9] 前記[7]又は[8]記載のエビ風味増強剤を含有する飲食品又は調味料。
[10] 前記1,5-オクタジエン-3-オン及び前記1,5-オクタジエン-3-オールの含有量の合計が質量基準で0.0001ppb~10ppmである、前記[9]記載の飲食品又は調味料。
[11] 前記[7]又は[8]記載のエビ風味増強剤を添加することにより、飲食品又は調味料へエビ風味を付与する方法。
[12] 前記[7]又は[8]記載のエビ風味増強剤を添加することにより、飲食品又は調味料のエビ風味を増強する方法。
また、本明細書において、“質量%”、“質量部”と“重量%”、“重量部”とはそれぞれ同義であり、単に“%”、“ppm”及び“ppb”と記載した場合、それぞれ“重量%”、“重量ppm”及び“重量ppb”のことを示す。
1,5-オクタジエン-3-オンは、分子内に二重結合への置換によるシス-トランスがあるために、(5E)-体と(5Z)-体の2個の幾何異性体が存在する。具体的には、(5E)-1,5-オクタジエン-3-オン、(5Z)-1,5-オクタジエン-3-オンの2種類がある。
また、1,5-オクタジエン-3-オールは、分子内に1個の不斉炭素を有しているため(3S)-体と(3R)-体があり、さらには二重結合への置換によるシス-トランスがあるために、(5E)-体と(5Z)-体の2個の幾何異性体が存在する。具体的には、(3S)-(5E)-1,5-オクタジエン-3-オール、(3R)-(5E)-1,5-オクタジエン-3-オール、(3S)-(5Z)-1,5-オクタジエン-3-オール、(3R)-(5Z)-1,5-オクタジエン-3-オールの4種類がある。
これらの1,5-オクタジエン-3-オン及び1,5-オクタジエン-3-オールは、いずれも、常温でオイル状(液状)を呈している。
これら異性体はガスクロマトグラフィーの保持時間によって区別することができる。また、本明細書では、これら異性体を区別せずに、それぞれまとめて「1,5-オクタジエン-3-オン」又は「1,5-オクタジエン-3-オール」と称するものとする。
化学合成による場合では、1,5-オクタジエン-3-オン及び/又は1,5-オクタジエン-3-オールの高純度のものを多量に取得することができる。
他の香気成分としては例えば、リモネン、オシメン、α-ピネン、β-ピネン、γ-テルピネン、サビネン、ミルセンなどの炭化水素類;リナロール、シトロネロール、ジヒドロリナロール、テトラヒドロムゴール、ミルセノール、ジヒドロミルセノール、テトラヒドロミルセノール、オシメノール、テルピネオール、3-ツヤノール、ベンジルアルコール、β-フェニルエチルアルコール、α-フェニルエチルアルコール、シス-3-ヘキセノールなどのアルコール類;アセトアルデヒド、n-ヘキサナール、n-ヘプタナール、n-オクタナール、n-ノナナール、シス-3-ヘキセナール、シス-6-ノネナール、3,5,5-トリメチルヘキサナール、デカナール、ウンデカナール、2-メチルデカナール、ドデカナール、トリデカナール、テトラデカナール、トランス-2-ヘキセナール、トランス-4-デセナール、シス-4-デセナール、トランス-2-デセナール、10-ウンデセナール、トランス-2-ウンデセナール、トランス-2-ドデセナール、3-ドデセナール、トランス-2-トリデセナール、2,4-ヘキサジエナール、2,4-デカジエナール、2,4-ドデカジエナール、5,9-ジメチル-4,8-デカジエナール、シトラール、シトロネラール、ベンズアルデヒド、クミンアルデヒド、バニリン、エチルバニリンなどのアルデヒド類;2-ブタノン、3-ヘプタノン、3-オクタノン、2-ノナノン、2-ウンデカノン、2-トリデカノン、メチルヘプテノン、ジメチルオクテノン、ゲラニルアセトン、2,3,5-トリメチル-4-シクロヘキセニル-1-メチルケトン、3-メチル-2,4-ノナンジオン、ネロン(ジボダン社、登録商標)、ヌートカトン、ジヒドロヌートカトン、アセトフェノン、4,7-ジヒドロ-2-イソペンチル-2-メチル-1,3-ジオキセピンなどのケトン類;ギ酸プロピル、ギ酸オクチル、ギ酸リナリル、ギ酸シトロネリル、ギ酸ゲラニル、ギ酸ネリル、ギ酸テルピニル、酢酸エチル、酢酸イソプロピル、酢酸シス-3-ヘキセニル、酢酸トランス-2-ヘキセニル、酢酸オクチル、酢酸ノニル、酢酸デシル、酢酸ドデシル、酢酸ジメチルウンデカジエニル、酢酸オシメニル、酢酸ミルセニル、酢酸ジヒドロミルセニル、酢酸リナリル、酢酸シトロネリル、酢酸ゲラニル、酢酸ネリル、酢酸テトラヒドロムゴール、酢酸ラバンジュリル、酢酸ネロリドール、酢酸ジヒドロクミニル、酢酸テルピニル、酢酸シトリル、酢酸ノピル、酢酸ジヒドロテルピニル、酢酸2,4-ジメチル-3-シクロヘキセニルメチル、酢酸ミラルディル、酢酸ベチコール、プロピオン酸デセニル、プロピオン酸リナリル、プロピオン酸ゲラニル、プロピオン酸ネリル、プロピオン酸テルピニル、プロピオン酸トリシクロデセニル、プロピオン酸スチラリル、酪酸オクチル、酪酸ネリル、酪酸シンナミル、イソ酪酸イソプロピル、イソ酪酸オクチル、イソ酪酸リナリル、イソ酪酸ネリル、イソ吉草酸リナリル、イソ吉草酸テルピニル、イソ吉草酸フェニルエチル、2-メチル吉草酸2-メチルペンチル、3-ヒドロキシヘキサン酸メチル、3-ヒドロキシヘキサン酸エチル、オクタン酸メチル、オクタン酸オクチル、オクタン酸リナリル、ノナン酸メチル、ウンデシレン酸メチル、安息香酸リナリル、ケイヒ酸メチル、アンゲリカ酸イソプレニル、ゲラン酸メチル、クエン酸トリエチルなどのエステル類;チモール、カルバクロール、β-ナフトールイソブチルエーテルなどのフェノール類;γ-ウンデカラクトン、δ-ドデカラクトンなどのラクトン類;酢酸、プロピオン酸、酪酸、吉草酸、ヘキサン酸、オクタン酸、デカン酸、ドデカン酸、2-デセン酸、ゲラン酸などの脂肪酸類;ジアリルサルファイド、ジアリルジサルファイド、ジプロピルジサルファイド、メチルプロピルジサルファイド、アリルプロピルジサルファイド、ジアリルトリサルファイドなどのサルファイド類;アントラニル酸メチル、アントラニル酸エチル、N-メチルアントラニル酸メチル、N-2’-メチルペンチリデンアントラニル酸メチル、リガントラール、ドデカンニトリル、2-トリデセンニトリル、ゲラニルニトリル、シトロネリルニトリル、3,7-ジメチル-2,6-ノナジエノニトリル、インドール、5-メチル-3-ヘプタノンオキシム、チオゲラニオール、リモネンチオール、P-メンチル-8-チオールなどの含窒素・含硫化合物類;など公知の合成香料化合物および
甲殻類(エビ、カニなど)のエキス;溶剤抽出物、水蒸気蒸留物、酵素処理、加熱反応などにより得られる甲殻類風味を有するフレーバー;魚介類のエキス;ペパーミント油、スペアミント油、ジンジャー、ペッパー、オニオンなどのスパイス精油などの植物精油;スパイス類エキストラクトなどの油性エキストラクト及びこれらのオレオレジン類;等を挙げることができるがこれらに限定されるわけではない。
これらを任意に組み合わせて混合することにより、エビフレーバー組成物を調製することができる。
これらはエビフレーバー組成物に対して0~99質量%含まれることが組成物の取り扱いやすさの点から好ましい。
また、もともとエビ風味を有する飲食品又は調味品に本発明に係るエビフレーバー組成物を添加すれば、前記エビ風味が増強した飲食品又は調味品を得ることもできる。
ここでの1,5-オクタジエン-3-オン及び/又は1,5-オクタジエン-3-オールは先述した幾何異性体のうち一種を用いても二種以上を組み合わせて用いてもよい。
実施例1として1,5-オクタジエン-3-オンの0.1%水溶液を調製し、エビ風味増強剤を調製した。ここで1,5-オクタジエン-3-オンは(5Z)-1,5-オクタジエン-3-オンであり、非特許文献6に記載の合成方法により得た。
(実施例2)エビ風味増強剤
実施例2として1,5-オクタジエン-3-オンの0.1%水溶液を調製し、エビ風味増強剤を調整した。ここで1,5-オクタジエン-3-オールは(5Z)-1,5-オクタジエン-3-オールであり、非特許文献6に記載の合成方法により得た。
下記表1に記載の処方に従い、各成分を混合し、エビフレーバー組成物を得た。得られた組成物はいずれもボイル風味を有していた。
エビ風味増強剤を含まないこと以外は、実施例3と同様にしてエビフレーバー組成物を調製した。
エビがら200gに水1kgを加えて120℃で4時間加熱後冷却し、次いで不溶性固形物を除去してエビエキス850gを得た。このエキスを1/3の質量になるまで減圧濃縮し、得られた濃縮物に菜種油150g及び実施例3のエビフレーバー組成物を菜種油に対して2質量%添加して、100℃で3時間撹拌加熱した。次いで冷却後遠心分離してエビの風味の油層部を採取し本発明品1(エビ風味油)を得た。
実施例3のエビフレーバー組成物の代わりに実施例4のエビフレーバー組成物を用いた以外は、応用例1と同様にして本発明品2(エビ風味油)を得た。
実施例3のエビフレーバー組成物の代わりに比較例1のエビフレーバー組成物を用いた以外は、応用例1と同様にして比較品1(エビ風味油)を得た。
実施例1と同様にして、1,5-オクタジエン-3-オンが表2に示す濃度になるように変化させて1,5-オクタジエン-3-オンの水溶液を調製し、試験例1-1~1-8におけるエビ風味増強剤をそれぞれ調製した。次いで、実施例3の「実施例1のエビ風味増強剤」の代わりに調製したエビ風味増強剤をそれぞれ用いて、試験例1-1~1-8におけるエビフレーバー組成物を調製した。
実施例2と同様にして、1,5-オクタジエン-3-オールが表3に示す濃度になるように変化させて1,5-オクタジエン-3-オールの水溶液を調製し、試験例2-1~2-8におけるエビ風味増強剤をそれぞれ調製した。次いで、実施例4の「実施例2のエビ風味増強剤」の代わりに調製したエビ風味増強剤をそれぞれ用いて、試験例2-1~2-8におけるエビフレーバー組成物を調製した。
本出願は2012年10月2日出願の日本特許出願(特願2012-220787)に基づくものであり、その内容はここに参照として取り込まれる。
Claims (12)
- 1,5-オクタジエン-3-オン及び1,5-オクタジエン-3-オールの少なくともいずれか一方を含有するエビフレーバー組成物。
- ボイル風味、フライ風味又はロースト風味から選ばれるエビ風味を有する、請求項1記載のエビフレーバー組成物。
- 前記1,5-オクタジエン-3-オン及び前記1,5-オクタジエン-3-オールの含有量の合計が質量基準で0.001ppm~1000ppmである、請求項1又は2記載のエビフレーバー組成物。
- 請求項1~3のいずれか一項に記載のエビフレーバー組成物を含有する飲食品又は調味料。
- 請求項1~3のいずれか一項に記載のエビフレーバー組成物を添加することにより、飲食品又は調味料にエビ風味を付与する方法。
- 請求項1~3のいずれか一項に記載のエビフレーバー組成物を添加することにより、飲食品又は調味料のエビ風味を増強する方法。
- 1,5-オクタジエン-3-オン及び1,5-オクタジエン-3-オールの少なくともいずれか一方からなるエビ風味増強剤。
- ボイル風味、フライ風味又はロースト風味から選ばれるエビ風味を増強する、請求項7記載のエビ風味増強剤。
- 請求項7又は8記載のエビ風味増強剤を含有する飲食品又は調味料。
- 前記1,5-オクタジエン-3-オン及び前記1,5-オクタジエン-3-オールの含有量の合計が質量基準で0.0001ppb~10ppmである、請求項9記載の飲食品又は調味料。
- 請求項7又は8記載のエビ風味増強剤を添加することにより、飲食品又は調味料へエビ風味を付与する方法。
- 請求項7又は8記載のエビ風味増強剤を添加することにより、飲食品又は調味料のエビ風味を増強する方法。
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EP13843639.9A EP2904909A4 (en) | 2012-10-02 | 2013-10-02 | SHRIMP FLAVOR COMPOSITION AND SHRIMP TASTE EXHAUSTER |
SG11201502525PA SG11201502525PA (en) | 2012-10-02 | 2013-10-02 | Shrimp flavor composition and shrimp flavor enhancer |
US14/432,895 US20150257421A1 (en) | 2012-10-02 | 2013-10-02 | Shrimp flavor composition and shrimp flavor enhancer |
MX2015004187A MX2015004187A (es) | 2012-10-02 | 2013-10-02 | Composicion con sabor a camaron y potenciador del sabor a camaron. |
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CN201380051802.9A CN104684413A (zh) | 2012-10-02 | 2013-10-02 | 虾味组合物和虾风味增强剂 |
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NAKATOH, A.: "New approach to home style flavor creatiojn prawn and chicken", TAKASAGO SYMPOSIUM 2012, June 2013 (2013-06-01), KORYO, pages 69 - 79 * |
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SWOBODA, P. A. T. ET AL.: "Metallic odour caused by vinyl ketones formed in the oxidation of butterfat. The identification of octa-1, cis-5-dien-3-one", J. SCI. FD AGRIC., vol. 28, 1977, pages 1019 - 1024, XP055251610 * |
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JPWO2014054705A1 (ja) | 2016-08-25 |
MX2015004187A (es) | 2015-06-10 |
EP2904909A1 (en) | 2015-08-12 |
CN104684413A (zh) | 2015-06-03 |
BR112015007566A2 (pt) | 2017-07-04 |
US20150257421A1 (en) | 2015-09-17 |
SG11201502525PA (en) | 2015-05-28 |
EP2904909A4 (en) | 2016-06-22 |
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