WO2018079640A1 - 食品用変色防止剤 - Google Patents
食品用変色防止剤 Download PDFInfo
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- WO2018079640A1 WO2018079640A1 PCT/JP2017/038641 JP2017038641W WO2018079640A1 WO 2018079640 A1 WO2018079640 A1 WO 2018079640A1 JP 2017038641 W JP2017038641 W JP 2017038641W WO 2018079640 A1 WO2018079640 A1 WO 2018079640A1
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- Prior art keywords
- molecular weight
- lignin
- food
- discoloration
- present
- 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
- A23L3/00—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
- A23L3/34—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals
- A23L3/3454—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals in the form of liquids or solids
- A23L3/3463—Organic compounds; Microorganisms; Enzymes
- A23L3/3472—Compounds of undetermined constitution obtained from animals or plants
-
- 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
- A23L5/00—Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
- A23L5/40—Colouring or decolouring of foods
- A23L5/41—Retaining or modifying natural colour by use of additives, e.g. optical brighteners
-
- 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 inventors have conducted low molecular weight lignin and / or molecular weight of 10,000 to 10,000 having a molecular weight peak at a wavelength of 254 nm in the molecular weight range of 4,000 to 9,500 in GPC molecular weight analysis using a UV detector.
- the present inventors have found that a polymer lignin having a range of 40,000 has an effect of replacing sulfite as a food discoloration inhibitor, and thus completed the present invention.
- the present invention has the following configurations (1) to (9).
- (1) In GPC molecular weight analysis using a UV detector, a low molecular lignin having a molecular weight peak at a wavelength of 254 nm in the range of 4,000 to 9,500 and / or a molecular weight of 10,000 to 40,000.
- a food discoloration inhibitor comprising a polymer lignin as an active ingredient.
- (2) A composition containing 0.05% by weight or more of the low molecular weight lignin and / or the high molecular weight lignin having a molecular weight in the range of 10,000 to 40,000 as a polyphenol amount in terms of catechin is (1) Discoloration inhibitor for foods as described in 1.
- the preferred molecular weight range of the molecular weight peak of the low molecular weight lignin used in the present invention is 4,500 to 9,400, more preferably 5,000 to 9,300.
- the molecular weight of lignin can be determined by the number average molecular weight.
- the preferable average molecular weight of the low molecular weight lignin used in the present invention is 3,500 or more and 6,000 or less, more preferably 3,600 or more and 5,000 or less as the number average molecular weight in GPC molecular weight analysis using a UV detector. is there.
- the preferred average molecular weight of the polymer lignin used in the present invention is 10,000 or more and 20,000 or less, more preferably 10,000 or more and 15,000 or less as the number average molecular weight in GPC molecular weight analysis using a UV detector. is there.
- the preferred average molecular weight of the lignin containing both the low molecular weight lignin and the high molecular weight lignin used in the present invention is 4,000 to 15,000 as the number average molecular weight in GPC molecular weight analysis using a UV detector, more preferably 6,000 to 10,000.
- the low molecular lignin and the high molecular lignin used in the present invention may have a plurality of molecular weight peaks as long as they are within the above molecular weight range. Furthermore, although it may have a molecular weight peak outside the above molecular weight range, in that case, the peak having the maximum height among the molecular weight peaks at a wavelength of 254 nm is the low molecular lignin used in the present invention. If the molecular weight is 4,000 to 9,500 and the polymer lignin used in the present invention, the molecular weight is preferably in the range of 10,000 to 40,000.
- FIG. 1 shows a specific example of GPC molecular weight analysis using a UV detector when both the low molecular lignin used in the present invention and the high molecular lignin used in the present invention are contained.
- a specific example of the low-molecular lignin used in the present invention is shown in FIG. 2, and a specific example of the high-molecular lignin used in the present invention is shown in FIG. 2
- the low molecular lignin used in the present invention is referred to as the low molecular lignin of the present invention
- the high molecular lignin used in the present invention is referred to as the high molecular lignin of the present invention.
- GPC is an abbreviation for Gel Permeation Chromatography; it can separate compounds in a measurement sample for each molecular size.
- the molecular weight can also be calculated by detecting the relative amount of the separated polymer with a detector.
- GPC molecular weight analysis the relationship between elution time and molecular weight is obtained in advance using a standard polymer, and the molecular weight of the measurement sample is converted based on this.
- the molecular weights of the low molecular weight lignin of the present invention and the high molecular weight lignin of the present invention are values measured using polyethylene glycol and polyethylene oxide as standard polymers.
- the detector for GPC molecular weight analysis a detector capable of detecting 250 to 300 nm, which is the absorption wavelength region of lignin, can be used.
- the value analyzed at 254 nm without absorption of cinnamic acids is used in order to eliminate the influence of cinnamic acids such as coumaric acid and ferulic acid which are low molecular aromatics during GPC molecular weight analysis.
- the lignin of the present invention is a value detected by a multi-wavelength ultraviolet-visible absorption detector (SPD-M20A) manufactured by Shimadzu Corporation. From the molecular weight obtained by GPC molecular weight analysis, the number average molecular weight can be calculated by the following formula (1).
- Mn is the number average molecular weight
- M is the molecular weight
- N is the number of polymers
- C is the sample concentration.
- the molecular weight of this invention is the value measured using TSKgelGMPW XL and G2500PW XL .
- the low molecular lignin of the present invention and / or the plant used as the raw material of the high molecular lignin of the present invention include conifers such as pine, cedar and cypress, broad-leaved trees such as eucalyptus and acacia, bagasse and switches that are squeezed sugar cane Grass-based biomass such as grass, napiergrass, Eliansus, corn stover, rice straw, straw, etc., biomass derived from aquatic environment such as algae and seaweed, and cereal shell biomass such as corn hull, wheat hull, soybean hull, rice hull etc. be able to. Bagasse is preferable.
- Examples of the method for extracting the low molecular weight lignin of the present invention and / or the high molecular weight lignin of the present invention from the plant include extraction with an organic solvent (ethanol, ethyl acetate, etc.), acid extraction, alkali extraction, hydrothermal extraction, alkaline hydrothermal heat. Extraction or alkaline hot water extraction is preferred, preferably alkaline extraction or alkaline hot water extraction, and more preferably alkaline hot water extraction.
- the alkali compound used for alkali extraction, alkaline hydrothermal extraction or alkaline hot water extraction is not particularly limited, and examples thereof include sodium hydroxide, potassium hydroxide, calcium hydroxide, magnesium hydroxide, and ammonia, preferably sodium hydroxide. Potassium hydroxide, more preferably sodium hydroxide.
- the conditions for alkaline hot water extraction are preferably pH 10 or more and 13.5 or less, temperature 80 ° C. or more and 120 ° C. or less, preferably 0.5 hours or more, more preferably pH 10.5 or more and 13.0 or less, temperature 90 ° C. or more and 120 ° C. or less. It is preferable to make it react for 1 hour or more.
- the upper limit of the alkali concentration is not particularly limited as long as the food discoloration inhibitor of the present invention can be obtained. However, when the alkali concentration is too high for biomass, lignin is reduced in molecular weight, so that the food discoloration prevention of the present invention is performed. For example, when sodium hydroxide is used, 40 g / L or less is preferable because an effective component as an agent cannot be obtained, or a large amount of coloring components are produced, resulting in coloring the food to be processed. .
- Hydrothermal treatment is a method of extracting lignin by treatment with pressurized hot water (180-240 ° C.).
- Alkaline hydrothermal extraction is a method of extracting lignin by treating with pressurized hot water (180 to 240 ° C.) under the pH conditions of alkaline hot water extraction.
- a bagasse 50 g / L (dry weight) concentration solution is reacted at 90 ° C. with a 0.45 (wt / wt)% sodium hydroxide aqueous solution for 2 hours.
- the low molecular lignin of the present invention and / or the high molecular lignin of the present invention can be extracted.
- the dry weight is the weight after drying bagasse at 105 ° C. until the weight becomes constant.
- the low molecular weight lignin of the present invention is converted into a solid fraction by neutralizing to pH 5 or lower and solid-liquid separation.
- the polymeric lignin of the present invention can be separated. This is because the low molecular weight lignin of the present invention dissolves in water under the condition of pH 5, whereas the high molecular weight lignin of the present invention has a feature that it precipitates without dissolving in water.
- the polymer lignin insolubilized under the condition of pH 5 can be redissolved in water by setting the pH again to the alkali side from pH 5, for example, pH 8 or more.
- the preferred content of the low molecular weight lignin of the present invention and / or the high molecular weight lignin of the present invention in the food discoloration preventing agent of the present invention is 0.05% by weight or more in terms of catechin as the amount of polyphenol.
- a more preferred content is 0.1% by weight or more, and most preferred is 0.128% by weight or more.
- the upper limit of the amount of polyphenols is not particularly limited in exhibiting the effect of the food discoloration inhibitor, but when other brown components are mixed, adjusting to a large amount of polyphenols by concentration etc. Since brown components and the like adhere to food and change the appearance and flavor of the food, the content is preferably 2% by weight or less.
- the food discoloration inhibitor of the present invention When used as a solution, it can be used by adjusting to the above concentration range, and when kneaded into food, the weight ratio to the food is as described above. It is preferable to adjust and use it within the range.
- the amount of polyphenol in terms of catechin of the present invention is a value calculated by the foreign thiocult method.
- the foreign thiocult method was originally developed for the purpose of analyzing aromatic amino acids such as tyrosine and tryptophan and proteins having these. This is a method for colorimetric determination at 700 to 770 nm of a blue color generated by reducing phenolic hydroxyl group and molybdic acid with an alkaline phenolic hydroxyl group. The same operation is performed with a specific reference substance such as gallic acid and catechin, and a quantitative value can be shown in terms of the compound. In the present invention, the value in terms of catechin is used. It has the effect of preventing discoloration.
- the discoloration prevented by the food discoloration preventing agent of the present invention refers to a color change from a natural color to brown in the process of storing food. Color is important as an index for discriminating freshness, and by preventing discoloration, food quality and commercial value can be increased.
- the food to which the food discoloration inhibitor of the present invention is applied is not particularly limited as long as it changes in color during storage, and fresh food is preferred.
- the fresh food used in the present invention is food that is not completely heated, and includes food that is partially heated such as the surface of the food, but food that is not heated is preferred.
- Unheated food refers to food that has been stored at room temperature (30 ° C.) or lower after the food is produced or harvested.
- the food that is completely heated is a food that has been heated for 1 minute or more at a central temperature of the food of 75 ° C. or higher.
- Fresh food includes cut foods, foods obtained by cutting and mixing a plurality of foods, and seasoned foods, but unseasoned foods are preferred.
- fresh food examples include shellfish such as shrimp and crab, meat such as beef, pork and chicken, tuna, salmon, trout, bonito, sardines, saury, saury, saury, yellowtail, cod, cod, hokke, Thailand, and eelfish.
- Fish such as puffer, octopus, squid, vegetables such as cabbage, lettuce, spinach, eggplant, cucumber, onion, okra, potato, and fruits such as apple, banana, oyster, peach, avocado, etc.
- crustaceans include: Cyprididae, Pteridomyceae, Clamaceae, Trichodiaceae, Tridacnaceae, Chilobiidae, Kidahigebiidae, Kurumaebiidae, Musibiidae, Sakurabibiidae, Hyodosabiidae, Numaebiidae, Mikaebiidae, Vietnamesemp, Vietnamesemp, Vietnamesemp, Schmp, Crayfish, Crayfish, Schmp, Osate, Shrimp, Shrimp, Shrimp Kingfish, crabs, crabs, crabs, crabs, crabs, spiders, crabs, crabs, crabs Two-family, portunus trituberculatus family, geryonidae, Ougigani Department, Enkougani Department, ocypodidae, pachygrapsus crassipes family, and the like Kakure
- lobsters of the lobster family lobsters of the crustaceae family, elephant lobster, black shrimp, tiger shrimp family, black tiger, white tiger, tiger shrimp, tiger shrimp, red shrimp, tiger shrimp, tiger shrimp, tiger shrimp, tiger shrimp.
- the red tiger shrimp of the family Shrimp is preferred.
- the food discoloration inhibitor of the present invention may be used as a solution by dissolving the low molecular weight lignin of the present invention and / or the high molecular weight lignin of the present invention, or may be concentrated or dried. It may be used after solidifying.
- the food may be immersed, kneaded into the food, applied to the surface, or sprayed to adhere.
- the effect as a discoloration preventing agent is maintained even if washed with water.
- discoloration can be suppressed by immersing the cut portion that easily changes color because the cells touch oxygen.
- crustaceans such as shrimps, it is effective to immerse the entire food, and there is an effect of preventing discoloration occurring in the entire crustacean food.
- the proportion of the discolored area is visually evaluated or the evaluation result is obtained using the discoloration inhibitor of the present invention. It can be compared with the case where there was no.
- the discolored area can be evaluated in the following 0 to 10 levels. 0: No brown, 2: Brown ratio 0% or more and less than 20%, 4: Brown ratio 20% or more and less than 40%, 6: Brown ratio 40% or more and less than 60%, 8: Brown ratio 60% or more and less than 80%, 10 : Brown ratio 80% or more and 100% or less.
- the food discoloration preventing agent of the present invention may be a composition containing the low molecular lignin of the present invention and / or the polymer lignin of the present invention and other components.
- Other ingredients are not particularly limited as long as they do not inhibit food discoloration prevention, but plant-derived cinnamic acids, particularly coumaric acid and / or ferulic acid, are known to have food discoloration prevention. Therefore, the enhancement effect of the anti-discoloration action of food by the combined use with the low molecular weight lignin of the present invention and / or the high molecular weight lignin of the present invention is expected.
- the concentration in the liquid needs to be 1.0% by weight or more as a discoloration preventing effect by immersing food.
- adding a high concentration of coumaric acid and ferulic acid lowers economic competitiveness.
- the amount of coumaric acid and ferulic acid contained in the composition is less than 1.0% by weight of coumaric acid and 1.0% by weight of ferulic acid. Is preferably 0.04 to 0.5% by weight of coumaric acid and 0.008 to 0.5% by weight of ferulic acid.
- the coumaric acid and ferulic acid concentrations can be quantified by liquid high performance chromatography using a hydrophobic column and a UV detector.
- coumaric acid and ferulic acid can also be measured as polyphenol amounts by the same method as the low-molecular lignin or high-molecular lignin of the present invention.
- the amount of coumaric acid and ferulic acid contained in the composition is preferably 0.0296 to 0.37% by weight of coumaric acid and 0.0064 to 0.4% by weight of ferulic acid in terms of catechin as the amount of polyphenol.
- the polyphenol content contained in the food discoloration preventing agent of the present invention is the low molecular lignin of the present invention and / or the polymer lignin of the present invention. In addition, it is preferably 0.1% by weight or more, more preferably 0.2% by weight or more in terms of catechin.
- the food discoloration preventing agent of the present invention may contain components other than coumaric acid and ferulic acid.
- the food discoloration preventing agent of the present invention may be dissolved and used as a solution or may be solidified. During the cooking process of food or when storing a direct product, the food may be immersed, kneaded into the food, or attached to the surface. Further, after sufficiently contacting with food, even if it is washed away with water, it has an effect as a color change inhibitor for food of the present invention.
- the notation “ ⁇ ” in the table indicates the case where the low molecular weight lignin of the present invention, the high molecular weight lignin and the other lignin cannot be separately determined for catechin conversion, and the notation “0” in the table is theoretically It is clear that it was not included, or that no value was detected by measurement by the foreign thiocult method.
- This alkaline extract was subjected to GPC molecular weight analysis by the method described in Reference Example 1.
- the analysis results are shown in FIG. From this analysis result, it was confirmed that the obtained lignin contained the low molecular lignin of the present invention having a peak at a molecular weight of 7,000 and the high molecular lignin of the present invention having a molecular weight peak at a molecular weight of 21,000.
- the number average molecular weight was 8,900.
- the amount of polyphenols in this bagasse alkaline hot water extract was measured according to Reference Example 2, it was 0.2% by weight in terms of catechin.
- Frozen vaname shrimp (trade name: Myoko Yuki shrimp, manufactured by IMT Engineering Co., Ltd.) L size (about 15 g per animal), which is not used for the food discoloration prevention agent of the present invention, is rapidly thawed with cold water and the bagasse alkali It was immersed in 150 mL of hot water extract (30 mL per animal) for 5 minutes. After soaking, the shrimps were washed with tap water, wrapped in a wrap film and stored at 4 ° C. for 6 days. State observation was performed on the 2nd and 6th days of storage, and the ratio of the area turned brown was evaluated by an appearance test by 6 panelists.
- the discoloration was visually evaluated according to the method described in Non-Patent Document 1, and the following evaluation values from 0 to 10 were set visually and evaluated in 6 stages (average value per 5 animals).
- 0 No brown
- 2 Brown ratio 0% or more and less than 20%
- 4 Brown ratio 20% or more and less than 40%
- 6 Brown ratio 40% or more and less than 60%
- 8 Brown ratio 60% or more and less than 80%
- 10 Brown ratio 80% or more and 100% or less.
- Table 1 shows the average of the respective measurement results and the panelist evaluation results.
- Test Example 2 Shrimp discoloration prevention effect (low molecular lignin of the present invention)
- the bagasse alkaline hot water extract prepared in Test Example 1 was neutralized to pH 3 with 6N hydrochloric acid to precipitate the polymer lignin of the present invention.
- solid-liquid separation is performed using a filter press (YTO type manufactured by Iwata Machinery Co., Ltd.), and the low molecular weight lignin solution of the present invention is placed on the filtrate side, and the polymer lignin of the present invention is solidified. Separated to the minute side.
- the obtained filtrate was adjusted to pH 7 with 50% (wt / v) sodium hydroxide, and GPC molecular weight analysis was performed by the method described in Reference Example 1.
- the results of GPC molecular weight analysis are shown in FIG. From this analysis result, it was confirmed that the obtained lignin had the main peak of the low molecular weight lignin of the present invention having a peak at a molecular weight of 7,000. Moreover, the number average molecular weight calculated
- Test Example 3 Shrimp discoloration prevention effect (polymer lignin of the present invention)
- 50% (wt / v) sodium hydroxide was added to adjust the pH to 12, and the polymer lignin of the present invention was dissolved.
- the polymer lignin solution of the present invention was adjusted to pH 7 with 6N hydrochloric acid, and GPC molecular weight analysis was performed by the method described in Reference Example 1. The results of GPC molecular weight analysis are shown in FIG.
- the obtained lignin was the high molecular lignin of the present invention having a peak at a molecular weight of 21,000, and the low molecular lignin of the present invention was not contained.
- required from this analysis result was 13,800.
- the amount of polyphenol of this polymer lignin solution of the present invention was measured according to Reference Example 2, it was 0.1% by weight in terms of catechin.
- coumaric acid and ferulic acid were measured by the method described in Reference Example 3, coumaric acid and ferulic acid were not detected.
- a shrimp discoloration preventing effect test was conducted under the same operation and conditions as in Test Example 1 except that the polymer lignin solution of the present invention obtained in Test Example 3 was used. Table 1 shows the average of the respective measurement results and the panelist evaluation results.
- Test Example 4 Shrimp discoloration preventing effect (low molecular lignin of the present invention and high molecular lignin of the present invention)
- the bagasse alkaline hot water extract of Test Example 1 was diluted twice with distilled water. The test was performed under the same operation and conditions as in Test Example 1 except that the obtained 2-fold diluted bagasse alkaline hot water extract was used. Table 1 shows the average of the respective measurement results and the panelist evaluation results.
- Test Example 5 Shrimp discoloration prevention effect (water) A test for preventing discoloration of shrimp was conducted using tap water. The test was performed under the same operation and conditions as in Test Example 1 except that tap water was used. Table 1 shows the average of the respective measurement results and the panelist evaluation results.
- Test Example 6 Shrimp discoloration prevention effect (sugar cane pressing solution) After crushing the sugarcane that had been cleaned after washing the leaves, add water (50 ° C warm water) to the sugarcane weight 1 and add it to the sugarcane weight 19 while squeezing it, and test the effect of preventing discoloration to shrimp. went. The test was conducted under the same operation and conditions as in Test Example 1 except that the sugar cane pressing solution was used. Table 1 shows the average of the respective measurement results and the panelist evaluation results.
- the active ingredient having the highest peak height has a peak at a molecular weight of 4,000 or less, and the active ingredient having the highest peak height is the low molecular lignin of the present invention and the polymer lignin of the present invention.
- the composition contains the low molecular lignin of the present invention and the high molecular lignin of the present invention.
- coumaric acid and ferulic acid were measured by the method described in Reference Example 3, coumaric acid and ferulic acid were not detected. Further, the solid content of the bagasse hydrothermal treatment liquid was measured and found to be 2.5%.
- Test Example 10 Shrimp discoloration prevention effect (low concentration of low molecular weight lignin of the present invention and high molecular weight lignin of the present invention)
- a solution was prepared by diluting the bagasse alkaline hot water extract of Test Example 1 four times with distilled water. The test was performed under the same operation and conditions as in Test Example 1 except that the solution diluted 4-fold was used. Table 1 shows the average of the respective measurement results and the panelist evaluation results.
- Test Example 13 Cabbage discoloration prevention effect (low molecular weight lignin of the present invention) The test was performed under the same operation and conditions as in Test Example 12 except that the low molecular weight lignin solution of the present invention similar to Test Example 2 was used. The average of the results is shown in Table 2.
- Test Example 14 Effect of preventing cabbage discoloration (polymer lignin of the present invention) The test was performed under the same operation and conditions as in Test Example 12 except that the polymer lignin solution of the present invention obtained in Test Example 3 was used. The results are shown in Table 2.
- Test Example 19 Discoloration prevention effect of cabbage (sodium pyrosulfite) The test was performed under the same operating conditions as in Test Example 12 except that the sodium pyrosulfite solution of Test Example 9 was used. The results are shown in Table 2.
- Test Example 24 Discoloration prevention effect of minced meat (sugar cane pressing solution) The test was performed under the same operation and conditions as in Test Example 20, except that the sugarcane pressing liquid of Test Example 6 was used. The results are shown in Table 3.
- Test Example 27 Discoloration prevention effect of minced meat (sodium pyrosulfite) The test was performed under the same operation and conditions as in Test Example 20, except that the sodium pyrosulfite solution of Test Example 9 was used. The results are shown in Table 3.
- Test Example 30 Yellowfin tuna discoloration prevention effect (polymer lignin of the present invention) The test was performed under the same operation and conditions as in Test Example 28 except that the polymer lignin solution of the present invention in Test Example 3 was used. The results are shown in Table 4.
- Test Example 35 Yellowfin tuna discoloration prevention effect (sodium pyrosulfite) The procedure was the same as Test Example 28 except that the sodium pyrosulfite solution of Test Example 9 was used. The results are shown in Table 4.
- Test Example 37 Effect of preventing discoloration of apple (low molecular weight lignin of the present invention) The test was conducted under the same procedures and conditions as in Test Example 36 except that the low molecular weight lignin solution of the present invention in Test Example 2 was used. The results are shown in Table 5.
- Test Example 40 Apple discoloration prevention effect (sugar cane pressing solution) The test was conducted under the same operation and conditions as in Test Example 36 except that the sugarcane pressing liquid of Test Example 6 was used. The results are shown in Table 5.
- Test Example 42 Apple discoloration prevention effect (ferulic acid) The test was performed under the same operation and conditions as in Test Example 36 except that the ferulic acid solution of Test Example 8 was used. The results are shown in Table 5.
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Abstract
Description
(1)UV検出器を用いたGPC分子量分析において、波長254nmにおける分子量ピークを、分子量4,000~9,500の範囲に有する低分子リグニンおよび/または分子量10,000~40,000の範囲に有する高分子リグニンを有効成分とする、食品用変色防止剤。
(2)前記低分子リグニンおよび/または分子量10,000~40,000の範囲に有する高分子リグニンを、ポリフェノール量としてカテキン換算0.05重量%以上含む組成物を有効成分とする、(1)に記載の食品用変色防止剤。
(3)さらにクマル酸および/またはフェルラ酸を含む組成物を有効成分とする、(2)に記載の食品用変色防止剤。
(4)前記組成物がバガスのアルカリ熱水抽出物である、(2)または(3)に記載の食品用変色防止剤。
(5)前記食品が生鮮食品である、(1)~(4)のいずれかに記載の食品用変色防止剤。
(6)前記生鮮食品が水産生物である、(5)に記載の食品用変色防止剤。
(7)前記水産生物が甲殻類である、(6)に記載の食品用変色防止剤。
(8)前記甲殻類がエビである、(7)に記載の食品用変色防止剤。
(9)前記食品用変色防止剤を食品に接触させることにより、食品の変色を防止する方法。
本発明の食品用変色防止剤は、食品の変色を防止する効果を有する。本発明の食品用変色防止剤で防止する変色とは、食品を保存する過程で自然の色調から褐色に変化するものを指す。色は鮮度を判別する指標として重要であり、変色を防止することで食品の品質、商品価値を高めることができる。
GPC分子量分析は以下の条件で実施した。
検出器:多波長紫外-可視吸収検出器 UV(株式会社島津製作所製SPD-M20A、波長254nm)
カラム:TSKgelGMPWXL、G2500PWXL直列に各1本(φ7.8mm×30cm、東ソー)
溶媒:アンモニア緩衝液(pH11)/メタノール(1/1=v/v)
流速:0.7mL/min
カラム温度:23℃
注入量:0.2mL
標準試料:東ソー株式会社製、Polymer Laboratories製単分散ポリエチレンオキサイド、ポリエチレングリコール。
ポリフェノール量の測定はフォーリンチオカルト法により以下の条件で実施した。適宜希釈した測定試料1.0mL、フェノール試液(ナカライテスク社)1.0mL、水5mLを25mLのメスフラスコに入れて5分間室温で放置し、これに7%炭酸ナトリウム水溶液10mLを加える。更に水を加えて25mLとして混合し、2時間室温で放置する。反応液の一部を取り、φ0.45μmのPTFEフィルターでろ過し、750nmで吸光度を測定する(吸光度は0.6ABS以下となるようにサンプルを適宜希釈)。標準物質としてカテキン試薬(シグマ社、純度98%以上)を用い、カテキン換算値として算出した。以下の試験例において、本参考例にしたがってポリフェノール量を測定した結果を表1から表6に示す。表中「-」の表記は、本発明の低分子リグニン、高分子リグニンとその他のリグニンとを分けてカテキン換算を求めることができない場合を示し、表中「0」の表記は、理論的に含まれないことが明らかなもの、あるいはフォーリンチオカルト法による測定で値が検出されなかったことを示す。
クマル酸、フェルラ酸等の芳香族化合物濃度の測定は以下の条件で実施した。
機器:日立高速液体クロマトグラムLaChrom Eite
カラム:Synergi 2.5μ Hydro-RP100A 100×3.00mm (Phenomenex)
移動相:0.1%リン酸:アセトニトリル=93:7から5:95までグラジェント
検出器:Diode Array
流速:0.6mL/min
温度:40℃。
バガス1kg(台糖農産株式会社より購入、ベトナム製)を0.45(wt/wt)%水酸化ナトリウム水溶液に乾燥重量で5wt%添加・混合し、90℃、2時間反応させ、6N塩酸を用いてpHを7に調整した後、ザルで固体を分離し、MF膜(商品名:トレフィルHFSタイプ、東レ株式会社製)で濾過を行い、バガスアルカリ熱水抽出液を作製した。このアルカリ抽出液を参考例1に記載の方法でGPC分子量分析を行った。分析結果を図1に示す。この分析結果から、得られたリグニンは、分子量7,000にピークを有する本発明の低分子リグニン、および分子量21,000に分子量ピークを有する本発明の高分子リグニンを含有することを確認した。また、数平均分子量は8,900であった。さらに、参考例2に従ってこのバガスアルカリ熱水抽出液のポリフェノール量を測定したところ、カテキン換算で0.2重量%であった。また、参考例3に記載の方法でクマル酸、フェルラ酸を測定したところ、クマル酸が0.08重量%、フェルラ酸が0.016重量%であり、同濃度のクマル酸、フェルラ酸のみ含有した液体のポリフェノール含量はカテキン換算で0.072重量%であった。このことから、本発明の低分子リグニンおよび高分子リグニンはカテキン換算で0.128重量%であることが分かる。
試験例1で作製したバガスアルカリ熱水抽出液を6N塩酸でpH3に中和し、本発明の高分子リグニンを沈殿させた。珪藻土を1%添加・混合後、フィルタープレス(薮田機械株式会社製YTO型)を用いて固液分離を行い、本発明の低分子リグニン液をろ液側に、本発明の高分子リグニンを固形分側に分離した。得られたろ液を50%(wt/v)の水酸化ナトリウムでpH7に調整し、参考例1に記載の方法でGPC分子量分析を行った。GPC分子量分析結果を図2に示す。この分析結果から、得られたリグニンは、分子量7,000にピークを有する本発明の低分子リグニンを主要ピークとしていることを確認した。また、GPC分子量分析結果から求められる数平均分子量は4,000であった。さらに、この本発明の低分子リグニンのポリフェノール量を参考例2に従って測定したところ、カテキン換算で0.1重量%であった。また、参考例3に記載の方法でクマル酸、フェルラ酸を測定したところ、クマル酸が0.06重量%、フェルラ酸が0.012重量%であり、同濃度のクマル酸、フェルラ酸のみ含有した液体のポリフェノール含量はカテキン換算で0.05重量%であった。このことから、本発明の低分子リグニンはカテキン換算で0.05重量%あることが分かる。試験例2で得られた本発明の低分子リグニン液を用いた以外は試験例1と同様の操作・条件でエビへの変色防止効果試験を行った。それぞれの測定結果と、パネリストの評価結果の平均を表1に示す。
試験例2で分離した固形分に対し、50%(wt/v)の水酸化ナトリウムを添加してpHを12に調整し、本発明の高分子リグニンを溶解した。この本発明の高分子リグニン液を6N塩酸でpH7に調整し、参考例1に記載の方法でGPC分子量分析を行った。GPC分子量分析結果を図3に示す。この分析結果から、得られたリグニンは、分子量21,000にピークを有する本発明の高分子リグニンであり、本発明の低分子リグニンは含有していないことを確認した。また、この分析結果から求められる数平均分子量は13,800であった。さらに、この本発明の高分子リグニン液を参考例2に従ってポリフェノール量を測定したところ、カテキン換算で0.1重量%であった。また、参考例3に記載の方法でクマル酸、フェルラ酸を測定したところ、クマル酸、フェルラ酸は検出されなかった。試験例3で得られた本発明の高分子リグニン液を用いた以外は試験例1と同様の操作・条件でエビへの変色防止効果試験を行った。それぞれの測定結果と、パネリストの評価結果の平均を表1に示す。
試験例1のバガスアルカリ熱水抽出液を蒸留水で2倍に希釈した。得られた2倍希釈したバガスアルカリ熱水抽出液を用いた以外は、試験例1と同様の操作・条件で試験を行った。それぞれの測定結果と、パネリストの評価結果の平均を表1に示す。
水道水を用いて、エビへの変色防止効果試験を行った。水道水を用いた以外は、試験例1と同様の操作・条件で試験を行った。それぞれの測定結果と、パネリストの評価結果の平均を表1に示す。
葉を取り除き洗浄したさとうきびを粉砕後、注加水(50℃温水)をさとうきび重量1に対し、注加水重量19で加えながら圧搾して得られた液を用いて、エビへの変色防止効果試験を行った。さとうきびの圧搾液を用いた以外は、試験例1と同様の操作・条件で試験を行った。それぞれの測定結果と、パネリストの評価結果の平均を表1に示す。
バガスを乾燥重量30(wt/wt)%(含水率70%)となるように調整し、高圧で180℃、10分水熱処理(高圧蒸煮処理)を行った。得られたバガス水熱処理物を固液分離し、得られたバガス水熱処理液を、1N水酸化ナトリウムを用いてpH7に調整した。次に、参考例1に記載の方法でGPC分子量分析を行った。結果を図4に示す。この分析結果から、バガスの水熱処理液は、ピーク高さが高い順に、分子量3,200、分子量6,000および分子量17,000に分子量ピークを有するリグニンを含んでいることがわかった。また、GPC分子量分析結果から求められる数平均分子量は2,870であった。このバガス水熱処理液を参考例2に従ってポリフェノール量を測定したところ、カテキン換算で0.001重量%であった。従って、バガスの水熱処理液には、還元力を有するリグニンがほとんど含まれていないことがわかった。バガス水熱処理液は、ピーク高さが最高となる有効成分は分子量4,000以下にピークをもち、このピーク高さが最高となる有効成分は本発明の低分子リグニン、本発明の高分子リグニンとは異なるものの、組成としては本発明の低分子リグニンおよび本発明の高分子リグニンを含有する。更に参考例3に記載の方法でクマル酸、フェルラ酸を測定したところ、クマル酸、フェルラ酸は検出されなかった。また、バガスの水熱処理液の固形分含量を測定したところ、2.5%であった。
フェルラ酸(東京化成工業社より購入、純度98%以上、分子量194)を4N水酸化ナトリウムでpHを7に調整しながら80mg/L(0.008重量%)となるようにフェルラ酸液を調製した。また、フェルラ酸液を参考例2に従ってポリフェノール量を測定したところ、カテキン換算で0.0064重量%であった。調製したフェルラ酸液を用いた以外は、試験例1と同様の操作・条件で試験を行った。それぞれの測定結果と、パネリストの評価結果の平均を表1に示す。
ピロ亜硫酸ナトリウム(ナカライテスク社より購入、純度96%以上、別名:二亜硫酸ナトリウム)を12.5g/L(1.25重量%)となるようにピロ亜硫酸ナトリウム液を調製した。調製したピロ亜硫酸ナトリウム液を用いた以外は、試験例1と同様の操作・条件で試験を行った。それぞれの測定結果と、パネリストの評価結果の平均を表1に示す。
試験例1のバガスアルカリ熱水抽出液を蒸留水で4倍に希釈した液を調製した。4倍に希釈した液を用いた以外は、試験例1と同様の操作・条件で試験を行った。それぞれの測定結果と、パネリストの評価結果の平均を表1に示す。
フェルラ酸(東京化成工業社より購入、純度98%以上、分子量194)を4N水酸化ナトリウムでpHを7に調整しながら1250mg/L(0.125重量%)となるようにフェルラ酸液を調製した。また、フェルラ酸液を参考例2に従ってポリフェノール量を測定したところ、カテキン換算で0.1重量%であった。調製したフェルラ酸液を用いた以外は、試験例1と同様の操作・条件で試験を行った。それぞれの測定結果と、パネリストの評価結果の平均を表1に示す。
4分の1カットキャベツの切り口に対し、試験例1で作製したバガスアルカリ熱水抽出液30mLに5分間浸漬させた。浸漬後、キャベツの浸漬部分を水道水で洗浄し、ラップフィルムに包んで4℃で7日間保存した。保存2日目と、7日目に状態観察を行い、キャベツ切り口における変色の度合いをパネリストによる外観試験により評価した。変色は非特許文献1に記載の方法に準じて、目視により以下の0~10段階で評価(2個あたりの平均値)した。0:褐色なし、2:褐色割合0%以上20%未満、4:褐色割合20%以上40%未満、6:褐色割合40%以上60%未満、8:褐色割合60%以上80%未満、10:褐色割合80%以上100%以下。結果を表2に示す。
試験例2と同様の本発明の低分子リグニン液を用いた以外は、試験例12と同様の操作・条件で試験を行った。結果の平均を表2に示す。
試験例3で得られた本発明の高分子リグニン液を用いた以外は、試験例12と同様の操作・条件で試験を行った。結果を表2に示す。
水道水を用いた以外は、試験例12と同様の操作・条件で試験を行った。結果を表2に示す。
試験例6のさとうきび圧搾液を用いた以外は、試験例12と同様の操作・条件で試験を行った。結果を表2に示す。
試験例7のバガス水熱処理液を用いた以外は、試験例12と同様の操作・条件で試験を行った。結果を表2に示す。
試験例8のフェルラ酸液を用いた以外は、試験例12と同様の操作・条件で試験を行った。それぞれの測定結果と、パネリストの評価結果を表2に示す。
試験例9のピロ亜硫酸ナトリウム液を用いた以外は、試験例12と同様の操作条件で試験を行った。結果を表2に示す。
牛豚合い挽き肉60gに対し、試験例1で作製したバガスアルカリ熱水抽出液30mLに5分間浸漬させた。浸漬後、浸漬部分を水道水で洗浄し、ラップフィルムに包んで4℃で保存した。0~5日間状態観察を行い、目視による変色の度合いをパネリスト6名による外観試験により評価した。変色は、目視により以下の0~10段階で評価(2検体あたりの平均値)した。0:褐色なし、2:褐色割合0%以上20%未満、4:褐色割合20%以上40%未満、6:褐色割合40%以上60%未満、8:褐色割合60%以上80%未満、10:褐色割合80%以上100%以下。結果を表3に示す。
試験例2の本発明の低分子リグニン液を用いた以外は、試験例20と同様の操作・条件で試験を行った。結果を表3に示す。
試験例3の本発明の高分子リグニン液を用いた以外は、試験例20と同様の操作・条件で試験を行った。結果を表3に示す。
水道水を用いた以外は、試験例20と同様の操作・条件で試験を行った。結果を表3に示す。
試験例6のさとうきび圧搾液を用いた以外は、試験例20と同様の操作・条件で試験を行った。結果を表3に示す。
試験例7のバガス水熱処理液を用いた以外は、試験例20と同様の操作・条件で試験を行った。結果を表3に示す。
試験例8のフェルラ酸液を用いた以外は、試験例20と同様の操作・条件で試験を行った。結果を表3に示す。
試験例9のピロ亜硫酸ナトリウム液を用いた以外は試験例20と同様の操作・条件で試験を行った。結果を表3に示す。
キハダマグロ約80g±10(FreshDeriたまや より購入)に対し、試験例1で作製したバガスアルカリ熱水抽出液15mLに5分間浸漬させた。浸漬後、浸漬部分を水道水で洗浄し、ラップフィルムに包んで4℃で保存した。0~5日間状態観察を行い、変色の度合いをパネリスト6名による外観試験により評価した。変色は非特許文献1に記載の方法に準じて、目視により以下の0~10段階で評価(2検体あたりの平均値)した。0:褐色なし、2:褐色割合0%以上20%未満、4:褐色割合20%以上40%未満、6:褐色割合40%以上60%未満、8:褐色割合60%以上80%未満、10:褐色割合80%以上100%以下。結果を表4に示す。
試験例2の本発明の低分子リグニン液を用いた以外は、試験例28と同様の操作・条件で試験を行った。結果を表4に示す。
試験例3の本発明の高分子リグニン液を用いた以外は、試験例28と同様の操作・条件で試験を行った。結果を表4に示す。
水道水を用いた以外は、試験例28と同様の操作・条件で試験を行った。結果を表4に示す。
試験例6のさとうきび圧搾液を用いた以外は、試験例28と同様の操作・条件で試験を行った。結果を表4に示す。
試験例7のバガス水熱処理液を用いた以外は、試験例28と同様の操作・条件で試験を行った。結果を表4に示す。
試験例8のフェルラ酸液を用いた以外は、試験例28と同様の操作・条件で試験を行った。結果を表4に示す。
試験例9のピロ亜硫酸ナトリウム液を用いた以外は試験例28と同様のとした。結果を表4に示す。
リンゴを半分にカットし、切り口を試験例1で作製したバガスアルカリ熱水抽出液15mLに5分間浸漬させた。浸漬後、浸漬部分を水道水で洗浄し、ラップフィルムに包んで4℃で保存した。0~1日間状態観察を行い、変色の度合いをパネリスト6名による外観試験により評価した。変色は非特許文献1に記載の方法に準じて、目視により以下の0~10段階で評価(2検体あたりの平均値)した。0:褐色なし、2:褐色割合0%以上20%未満、4:褐色割合20%以上40%未満、6:褐色割合40%以上60%未満、8:褐色割合60%以上80%未満、10:褐色割合80%以上100%以下。結果を表5に示す。
試験例2の本発明の低分子リグニン液を用いた以外は試験例36と同様の操作・条件で試験を行った。結果を表5に示す。
試験例3の本発明の高分子リグニン液を用いた以外は試験例36と同様の操作・条件で試験を行った。結果を表5に示す。
試験例5の水道水を用いた以外は試験例36と同様の操作・条件で試験を行った。結果を表5に示す。
試験例6のさとうきび圧搾液を用いた以外は、試験例36と同様の操作・条件で試験を行った。結果を表5に示す。
試験例7のバガス水熱処理液を用いた以外は試験例36と同様の操作・条件で試験を行った。結果を表5に示す。
試験例8のフェルラ酸液を用いた以外は試験例36と同様の操作・条件で試験を行った。結果を表5に示す。
試験例9のピロ亜硫酸ナトリウム液を用いた以外は試験例36と同様の操作・条件で試験を行った。結果を表5に示す。
リグノスルホン酸液(日本製紙ケミカル株式会社製 サンエキスP252をNaOHでpH10に調整した水溶液に3%溶解させたもの)を参考例1に記載の方法でGPC分子量分析を行った。結果を図5に示す。このリグノスルホン酸液をこの分析結果から、得られたリグニンは、分子量100,000にピークを有するリグニンを含有することを確認した。また、数平均分子量は39,000であった。さらに、参考例2に従ってこのバガスアルカリ熱水抽出液のポリフェノール量を測定したところ、カテキン換算で0.1重量%であった。さらに6N塩酸でpH7に調整したものを用いて、エビへの変色防止効果試験を行った。リグノスルホン酸液を用いた以外は、試験例1と同様の操作・条件で試験を行った。それぞれの測定結果と、パネリストの評価結果の平均を表6に示す。
バガス1kg(台糖農産株式会社より購入、ベトナム製)を0.6(wt/wt)%水酸化ナトリウム水溶液に乾燥重量で5wt%添加・混合し、180℃、5分反応させ、6N塩酸を用いてpHを7に調整した後、ザルで固体を分離し、MF膜(商品名:トレフィルHFSタイプ、東レ株式会社製)で濾過を行い、バガスアルカリ水熱処理液を作製した。このアルカリ水熱処理を参考例1に記載の方法でGPC分子量分析を行った。分析結果を図6に示す。この分析結果から、得られたリグニンは、分子量3,700にピークを有するリグニンを含有することを確認した。また、数平均分子量は3,300であった。このバガスアルカリ水熱処理液を、6N塩酸を用いてpH7に中和し、3(v/v)倍に減圧濃縮し、参考例2に従ってバガスアルカリ水熱処理液3倍濃縮液のポリフェノール量を測定したところ、カテキン換算で0.1重量%であった。アルカリ水熱処理液3倍濃縮液を用いた以外は、試験例1と同様の操作・条件で試験を行った。それぞれの測定結果と、パネリストの評価結果の平均を表6に示す。
試験例7で得られるバガス水熱処理液を40℃、減圧乾燥で重量変化が無くなるまで乾燥させ、固形分含量を測定したところ、3.3%であった。乾燥前のポリフェノール量がカテキン換算で0.001重量%であったことから、この固形分はカテキン換算で0.03重量%と計算される。
Claims (9)
- UV検出器を用いたGPC分子量分析において、波長254nmにおける分子量ピークを、分子量4,000~9,500の範囲に有する低分子リグニンおよび/または分子量10,000~40,000の範囲に有する高分子リグニンを有効成分とする、食品用変色防止剤。
- 前記低分子リグニンおよび/または高分子リグニンを、ポリフェノール量としてカテキン換算0.05重量%以上含む組成物を有効成分とする、請求項1に記載の食品用変色防止剤。
- さらにクマル酸および/またはフェルラ酸を含む組成物を有効成分とする、請求項2に記載の食品用変色防止剤。
- 前記組成物がバガスのアルカリ熱水抽出物である、請求項2または3に記載の食品用変色防止剤。
- 前記食品が生鮮食品である、請求項1~4のいずれかに記載の食品用変色防止剤。
- 前記生鮮食品が水産生物である、請求項5に記載の食品用変色防止剤。
- 前記水産生物が甲殻類である、請求項6に記載の食品用変色防止剤。
- 前記甲殻類がエビである、請求項7に記載の食品用変色防止剤。
- 前記食品用変色防止剤を食品に接触させることにより、食品の変色を防止する方法。
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JPH06311842A (ja) | 1993-04-28 | 1994-11-08 | Maruha Corp | 甲殻類の黒変防止剤及びその黒変防止方法 |
JP2005041969A (ja) * | 2003-07-28 | 2005-02-17 | Toyota Motor Corp | 樹脂用酸化防止剤 |
JP2008005724A (ja) * | 2006-06-28 | 2008-01-17 | Oji Paper Co Ltd | 褐変防止剤 |
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JP2006177434A (ja) * | 2004-12-22 | 2006-07-06 | Mitsubishi Electric Corp | 水素貯蔵・供給装置 |
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JPH06311842A (ja) | 1993-04-28 | 1994-11-08 | Maruha Corp | 甲殻類の黒変防止剤及びその黒変防止方法 |
JP2005041969A (ja) * | 2003-07-28 | 2005-02-17 | Toyota Motor Corp | 樹脂用酸化防止剤 |
JP2008005724A (ja) * | 2006-06-28 | 2008-01-17 | Oji Paper Co Ltd | 褐変防止剤 |
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