JP7374569B2 - Composition for determining deterioration odor of consumer goods - Google Patents

Description

The present invention relates to a composition for determining the deterioration odor of consumer goods.

In recent years, as consumers have become more health-conscious, products containing vitamins and other ingredients have become more appealing to a variety of products (hereinafter sometimes referred to as consumer goods) such as food and beverages, cosmetics, pharmaceuticals, and health and hygiene products. It's increasing. Among these, foods and drinks to which vitamin C has been added are a typical example.

However, since vitamin C is easily degraded by light and/or heat, the quality of consumer products containing vitamin C may deteriorate due to, for example, heat sterilization during manufacturing, irradiation with light during storage and sale, and heating. do not have. In particular, vitamin C is known to produce a deteriorated odor due to its deterioration (Patent Document 1). Therefore, even if the deterioration of vitamin C itself is slight, changes in the aroma of consumer goods due to the resulting deterioration odor have a large impact on consumers.

Conventionally, compounds generated when vitamin C deteriorates include furfural, 2-furoic acid (furan-2-carboxylic acid), and 3-hydroxypyran-2-one (3-hydroxy-2H-pyran-2-one). is known (Non-patent Document 1).

Japanese Patent Application Publication No. 2011-30512

Journal of Agricultural and Food Chemistry, 1998, 46, 5078-5082

However, Patent Document 1 and Non-Patent Document 1 do not describe the substance that causes the deterioration odor, much less the degree of contribution of the substance to the deterioration odor. Therefore, it has been difficult to quantitatively determine the deterioration odor generated from consumer goods containing vitamin C.

In view of the above, it is an object of the present invention to provide a composition for determining deterioration odor of consumer goods containing vitamin C, a pseudo deterioration odor composition of vitamin C, a method for determining deterioration odor of consumer goods, and a method of evaluating deterioration odor of consumer goods. It is to be.

As a result of intensive research to solve the above problems, the present inventors discovered a component with unknown aroma in consumer products containing vitamin C, and found that this component significantly contributed to deterioration odor. The invention related to the present application has now been completed.

Thus, a brief overview of typical inventions disclosed in this application is as follows.

[1] A composition for determining the deterioration odor of consumer goods containing vitamin C, the composition comprising 1,3-di(furan-2-yl)propan-1-one for determining the deterioration odor of consumer goods. .
[2] A vitamin C pseudo-deterioration odor composition containing 1,3-di(furan-2-yl)propan-1-one.
[3] The vitamin C pseudo-degraded odor composition according to [2], further comprising 4-hydroxy-2,5-dimethyl-3(2H)-furanone.
[4] A method for determining the odor of a consumer product containing vitamin C, using 1,3-di(furan-2-yl)propan-1-one as an indicator .
[5] A method for evaluating deterioration odor of consumer goods containing vitamin C, comprising the steps of: (a) quantifying 1,3-di(furan-2-yl)propan-1-one in the consumer goods; A method for evaluating deterioration odor of consumer goods, including:
[6] The deterioration odor evaluation method according to [5], which comprises the step of (b) quantifying 4-hydroxy-2,5-dimethyl-3(2H)-furanone in the consumer product. Deterioration odor evaluation method.

According to the present invention, it is possible to provide a composition for determining deterioration odor of consumer goods containing vitamin C, a pseudo deterioration odor composition of vitamin C, a method for determining deterioration odor of consumer goods, and a method of evaluating deterioration odor of consumer goods. can.

1 is a graph summarizing differences in the amount of 1,3-di(furan-2-yl)propan-1-one produced depending on storage conditions in Example 1. 1 is a graph summarizing differences in the amount of 4-hydroxy-2,5-dimethyl-3(2H)-furanone produced depending on storage conditions in Example 1. 1 is a graph summarizing differences in vitamin C residual rate depending on storage conditions in Example 1.

Hereinafter, one embodiment of the present invention will be described in detail. In this specification, "~" means a range including the lower limit and upper limit, and "concentration (ppm, ppb)" and "%" refer to "mass concentration" and "mass percent concentration," respectively, unless otherwise specified. shall represent. Furthermore, as used herein, "flavor" refers to one or more kinds of sensations that can be changed by aroma (aroma), typically including smell and/or taste. As used herein, the term "flavoring" includes adding a new flavor and/or enhancing the flavor; for example, as a result of adding or enhancing the flavor, the flavor improves. Contains what is done. Furthermore, as a result of flavoring, sensations other than smell and/or taste, such as cold sensation, warm sensation, texture (such as down the throat, hardness, viscosity, etc., also referred to as texture), irritating sensations such as carbonic acid and spiciness, It may also be something that enhances, suppresses, or improves. Further, in this specification, the flavor of food and drink products may be referred to as flavor. Moreover, in this specification, "addition" includes at least one of simply adding to a certain object by spraying, dropping, etc., and mixing with a certain object. In addition, in this specification, for example, when referring to "contains the present flavor-imparting composition or the present flavor composition," unless otherwise specified, the term "contains either the present flavor-imparting composition or the present flavor composition" refers to This includes not only cases where the flavoring composition contains both the flavoring composition and the fragrance composition.

( Composition for determining deterioration odor)
A composition for determining a deterioration odor according to an embodiment of the present invention is a 1,3-di(furan-2-yl)propan-1-one [1,3-di( furan-2-yl)propan-1-one] (hereinafter referred to as the compound).

The compound is described in US Pat. No. 2,532,279 as a product of the hydrogenation reaction of furfuryl acetofuran, but has never been detected in consumer products containing vitamin C. Furthermore, nothing was known about the aroma of this compound.

In this regard, as a result of intensive research, the present inventors discovered the subject compound as a component of the deterioration odor of consumer goods containing vitamin C when they were degraded by light and/or heat. . In addition, the present inventors confirmed that the present compound has a syrup-like and balsam-like aroma. Furthermore, as shown in Example 1 below, the present inventors conducted aroma extract dilution analysis (hereinafter referred to as AEDA) using sniff gas chromatography (hereinafter referred to as GC-O). After confirming the high degree of contribution of the present compound to the deterioration odor, it was found that furfural, 3-hydroxypyran-2-one (3-hydroxy-2H-pyran-2-one), etc. described in Non-Patent Document 1 It was confirmed that the contribution was approximately 10 times higher than that of Thus, the present inventors have discovered that a composition containing the present compound is useful as a composition for determining the deterioration odor of consumer goods containing vitamin C.

The compound of the present invention can be obtained by a common method, and can be synthesized, for example, based on the above-mentioned US Pat. No. 2,532,279. Furthermore, the compound of the present invention obtained by the above synthesis method may be further purified using means such as column chromatography or vacuum distillation, if necessary.

In addition, when using the present compound as a composition for determining a deterioration odor , other ingredients such as a solvent for dissolution or dilution, and additives such as stabilizers, antioxidants, fragrances, and plant extracts may be added. It may be used by preparing a composition suitable for practical purposes such as storage and use in determination tests.

In order to use the present compound as a composition for determining a deterioration odor, the present compound contained in a consumer product may be qualitatively or quantitatively detected and measured. Examples of the detection device include gas chromatography (GC), high performance liquid chromatography (HPLC), and the like. Alternatively, the compound may be detected by sensory evaluation. These specific methods will be explained later in the deterioration odor determination method and deterioration odor evaluation method.

As described above, the composition containing the compound of the present invention is very useful as a composition for determining the deterioration odor of consumer goods containing vitamin C.

(Pseudo deterioration odor composition)
A vitamin C pseudo-degraded odor composition according to an embodiment of the present invention contains 1,3-di(furan-2-yl)propan-1-one (the present compound). As mentioned above, the present compound contributes approximately 10 times more to the deterioration odor than furfural, 3-hydroxypyran-2-one, etc., which were conventionally known as components constituting the deterioration odor of vitamin C. Therefore , an appropriately diluted compound of the present invention can be used as a pseudo-degraded odor composition.

The pseudo-deterioration odor composition according to the present embodiment can be applied to various uses, and as a preferred example, it can be used to evaluate the masking effect of vitamin C deterioration odor. By using the pseudo-deterioration odor composition according to the present embodiment, the deterioration odor of vitamin C can be reproduced with high accuracy, so screening of the vitamin C deterioration odor masking agent and evaluation of the masking effect can be performed accurately and reproducibly. can do well.

Furthermore, the pseudo-deterioration odor composition of the present embodiment can reproduce the deterioration odor even better by mixing the above-mentioned known deterioration odor components in a predetermined ratio in addition to the compound of the present invention. It can be suitably used for determining deterioration odor in. That is, the pseudo-degraded odor composition of the present embodiment contains 4-hydroxy-2,5-dimethyl-3(2H)-furanone [4-hydroxy-2,5-dimethyl-3(2H)] in addition to the compound of the present invention. -furanone], furfural, 2-furoic acid, and 3-hydroxypyran-2-one. By doing so, the pseudo-degraded odor composition of this embodiment can be brought closer to the actually occurring degraded odor derived from vitamin C.

Furthermore, as shown in Example 1 below, the present inventors found that the contribution of 4-hydroxy-2,5-dimethyl-3(2H)-furanone to the odor of vitamin C deterioration was higher than that of furfural and 3-hydroxypyrane. It has been confirmed that it is approximately 10 times higher than -2-one and comparable to 1,3-di(furan-2-yl)propan-1-one.

Therefore, the pseudo-degraded odor composition according to the present embodiment preferably contains 4-hydroxy-2,5-dimethyl-3(2H)-furanone in addition to the present compound. By quantifying both the subject compound and 4-hydroxy-2,5-dimethyl-3(2H)-furanone, which contribute more to the odor of vitamin C deterioration than other substances, we can determine the difference in pH of vitamin C-containing beverages. It is possible to appropriately evaluate the influence of deterioration odor caused by

In addition, when the pseudo-degraded odor composition according to the present embodiment contains 4-hydroxy-2,5-dimethyl-3(2H)-furanone in addition to the present compound, the present compound (referred to as component (a)) and The content ratio with 4-hydroxy-2,5-dimethyl-3(2H)-furanone (component (b)) is not particularly limited, but as shown in the examples below, The mass ratio of component (b) to (a) [(b)/(a)] is preferably 2 to 60.

(Deterioration odor determination method)
A method for determining a deterioration odor of a consumer product according to an embodiment of the present invention is a method for determining a deterioration odor of a consumer product containing vitamin C. On (this compound) is used as an indicator . As mentioned above, the present compound has a very high contribution to the deterioration odor of vitamin C, so by using the present compound as an index, it is possible to accurately determine the deterioration odor of consumer goods containing vitamin C.

In the method for determining the deterioration odor of consumer goods according to the present embodiment, the step of quantifying the subject compound is not essential, and it is sufficient that the subject compound can be detected by any method. For example, when using GC, the retention time of the Compound is measured in advance, and then the consumer goods to be determined are analyzed to detect the Compound (such as internal standard method or standard addition method), or a well-trained method is used. A method of detecting the subject compound by GC-O was mentioned by the panelists. There is also a method of detecting the subject compound by sensory evaluation of the consumer goods to be determined by well-trained panelists.

In the method for determining the deterioration odor of consumer goods according to the present embodiment, the present compound may be used alone, or other components such as solvents for dissolution or dilution, stabilizers, antioxidants, and fragrances may be used. It can be used by blending additives such as , plant extracts, etc. into a composition suitable for practical use such as storage and use in determination tests.

(Deterioration odor evaluation method)
A method for evaluating deterioration odor of consumer goods according to an embodiment of the present invention is a method for evaluating deterioration odor of consumer goods containing vitamin C, comprising: (a) 1,3-di(furan- 2-yl)propan-1-one (the present compound). As mentioned above, this compound has a very high degree of contribution to the deterioration odor of vitamin C, so by using this compound as an indicator and quantifying this compound in consumer goods, it is possible to identify consumer goods that contain vitamin C. Deterioration odor can be evaluated with high accuracy. In addition, as shown in the Examples below, it is clear that the content of the Compound in consumer goods containing vitamin C increases as vitamin C deteriorates. By doing so, it is possible to accurately evaluate the degree of vitamin C deterioration of consumer goods containing vitamin C.

In the method for evaluating deterioration odor of consumer goods according to the present embodiment, any method can be used for quantifying the compound. For example, when measuring with GC-MS, a calibration curve is created using the subject compound as a standard, and the calibration curve is used to identify the peak of the subject compound contained in consumer goods, and the amount All you have to do is measure it. In addition, when using sensory evaluation as a method for quantifying the Compound, the Compound is diluted in several stages to prepare a standard sample of degraded odor at each concentration, and the odor of the evaluation sample prepared from consumer goods is compared with the standard sample. The amount of the Compound contained in the consumer product can be determined by sensory evaluation. As described above, in the deterioration odor evaluation method according to the present embodiment, highly objective quantitative determination is possible whether the present compound is quantified by instrumental analysis or sensory evaluation.

In the method of evaluating the deterioration odor of consumer goods, the subject compound is used alone or in the presence of other ingredients, such as solvents for dissolution or dilution, stabilizers, antioxidants, fragrances, plant extracts, etc. It can be used by blending additives to prepare a composition suitable for practical use such as storage and use in determination tests.

Furthermore, the method for evaluating deterioration odor of consumer goods according to the present embodiment further includes the step of (b) quantifying 4-hydroxy-2,5-dimethyl-3(2H)-furanone in the consumer goods. . As mentioned above, by quantifying both the subject compound and 4-hydroxy-2,5-dimethyl-3(2H)-furanone, which contribute more to vitamin C deterioration odor than other substances, we found that vitamin C-containing It is possible to appropriately evaluate the influence of differences in pH of beverages on deterioration odor.

In addition, in the deterioration odor evaluation method for consumer goods according to the present embodiment, the order of quantifying the present compound and 4-hydroxy-2,5-dimethyl-3(2H)-furanone does not matter; 4-hydroxy-2,5-dimethyl-3(2H)-furanone and 4-hydroxy-2,5-dimethyl-3(2H)-furanone may be determined simultaneously.

(Search method for deterioration odor masking agent)
A method for searching for a deterioration odor masking agent according to an embodiment of the present invention is a method for searching for a deterioration odor masking agent for consumer goods containing vitamin C, the method comprising: (a) 1,3-di(furan-2- (b) preparing an evaluation sample by adding a candidate for a deterioration odor masking agent to the deterioration odor standard sample; (c) The evaluation sample and the deteriorated odor standard sample to which the deteriorated odor masking agent candidate is not added are each subjected to a sensory evaluation to determine the masking effect of the deteriorated odor masking agent candidate.

As mentioned above, this compound has a very high degree of contribution to the deterioration odor of vitamin C, so the search method for a deterioration odor masking agent for vitamin C using this compound is extremely beneficial in terms of efficiency, cost, etc. It is.

(Consumer goods containing vitamin C)
The consumer goods containing vitamin C that are targeted in the composition for determining a deterioration odor, the pseudo deterioration odor composition , the method for determining a deterioration odor, the method for evaluating a deterioration odor, and the method for searching for a masking agent according to the present embodiment will be described below.

Generally, vitamin C is the common name for L-ascorbic acid ((R)-3,4-dihydroxy-5-((S)-1,2-dihydroxyethyl)furan-2(5H)-one). In the present specification, "vitamin C" refers to ascorbic acid including its optical isomers. The reason for this is that the present inventors have confirmed that 1,3-di(furan-2-yl)propan-1-one (the subject compound) is also included in the deterioration odor of consumer products containing ascorbic acid. It is.

Furthermore, the conditions under which consumer products containing vitamin C develop a deterioration odor are not particularly limited, but it has been confirmed that the deterioration occurs mainly due to light and heat.

In the present embodiment, the consumer goods containing vitamin C are not particularly limited, but may include foods and drinks, cosmetics, medicines, health and hygiene products, etc. Foods and drinks are preferable, and drinks are more preferable.

Foods and drinks containing vitamin C are not particularly limited, but examples include various citrus flavors such as lemon, orange, grapefruit, lime, mandarin, tangerine, kabosu, sudachi, hassaku, iyokan, yuzu, shikkuwasa, and kumquat; strawberry, blueberry, Various fruit flavors such as raspberry, apple, cherry, plum, apricot, peach, pineapple, banana, melon, mango, papaya, kiwi, pear, grape, Muscat, Kyoho; milk flavor such as milk, yogurt, butter; vanilla flavor; Various tea flavors such as green tea, black tea, oolong tea, and herbal tea; coffee flavor; cola flavor; cacao flavor; cocoa flavor; various mint flavors such as spearmint and peppermint; cinnamon, chamomile, cardamom, caraway, cumin, clove, pepper, Various spices or herbal flavors such as coriander, chili pepper, perilla, ginger, star anise, thyme, capsicum, nutmeg, basil, marjoram, rosemary, bay laurel, garlic, and wasabi; various nut flavors such as almond, cashew, and walnut; wine Various alcoholic flavors such as brandy, whiskey, rum, gin, liqueur, sake, shochu, and beer; Vegetable flavors such as onion, celery, carrot, tomato, and cucumber; Chicken, duck, pork, beef, mutton, horsemeat, etc. Various meat flavors: Red fish such as tuna, white fish such as mackerel, sea bream, salmon, and horse mackerel, freshwater fish such as sweetfish, trout, and carp, shellfish such as turban shell, clam, clam, freshwater clam, and various crustaceans such as shrimp and crab. various seafood and seaweed flavors such as seaweed, wakame, and kelp; various grain flavors such as wheat such as rice, barley, wheat, and malt; meat oils and fats such as beef tallow, chicken oil, and lard, and various fish flavors. Examples include food and drink products having one or more of the following flavors: various oil and fat flavors such as oil; In other words, it may be a food or drink that makes you feel only one type of flavor, or it may be a food or drink that makes you feel two or more types of flavor, and the multiple types of flavors may be similar or different; for example, the former Examples of the latter include fruit flavors with multiple fruit flavors such as banana, peach, and apple flavors (so-called mixed fruit flavors), and examples of the latter include those with citrus flavors such as lemon and milk flavors (citrus). Examples include drinks with flavored lactic acid bacteria, etc.), and drinks with mint, citrus, and cola flavors (mint or lemon flavored cola drinks, etc.).

More specific food and drink examples include rice crackers, arare, okoshi, rice cakes, steamed buns, sweet bean paste, yokan, water yolk, nishikidama, jelly, castella, hard candy, biscuits, crackers, potato chips, cookies, Confectionery such as pies, puddings, butter cream, custard cream, cream puffs, waffles, sponge cakes, donuts, chocolate, chewing gum, caramels, candies, pastes such as peanut paste; bread, udon, ramen, Chinese noodles, sushi, Gomokumeshi, fried rice, pilaf, gyoza skin, shumai skin, okonomiyaki, takoyaki, and other breads, noodles, and rice; rice bran pickles, pickled plums, fukujinzuke, bettarazuke, senmaizuke, rakkyo, miso pickles, takuan pickles, and, Pickles such as mackerel, sardines, saury, salmon, tuna, bonito, whale, flounder, sand eel, sweetfish, squid such as common squid, spear squid, crested squid, firefly squid, octopus, Seafood such as octopuses such as octopus, shrimp such as kuruma prawn, botan prawn, spiny lobster, and black tiger; crabs such as red king crab, snow crab, blue crab, and king crab; shellfish such as clams, clams, scallops, oysters, and mussels; Canned fish, boiled fish, tsukudani, surimi, fish paste products (chikuwa, kamaboko, fried kamaboko, crab leg kamaboko, etc.), fried foods, tempura, and other processed seafood foods; chicken, pork, beef, mutton, horse meat, etc. Meat products: curry, stew, beef stew, hayashi rice sauce, meat sauce, mapo tofu, hamburgers, gyoza, kamameshi base, soups (corn soup, tomato soup, consommé soup, etc.), meat balls, braised braised meat, canned meat, etc. Processed foods and drinks using livestock meat; table salt, seasoned salt, soy sauce, powdered soy sauce, miso, powdered miso, moromi, hishio, furikake, ochazuke base, margarine, mayonnaise, dressing, vinegar, sambai vinegar, powdered sushi vinegar, Chinese food Soy sauce, tempura soup, mentsuyu (kelp stock or bonito stock, etc.), sauce (chuno sauce, tomato sauce, etc.), ketchup, yakiniku sauce, curry roux, stew stock, soup stock, dashi stock (konbu stock or bonito stock) seasonings such as dashi (soup stock, etc.), compound seasonings, new mirin, mixed powders such as fried chicken powder and takoyaki powder, and animal or vegetable stock-flavored foods and drinks to which these seasonings are added; cheese, yogurt , dairy products such as butter; various yeasts such as beer yeast and baker's yeast, and various microbial fermented products such as lactic acid bacteria; simmered vegetables such as boiled vegetables, chikuzeni, oden, and hot pot dishes; toppings for take-out lunch boxes and side dishes; apples, grapes , fruit juice drinks and soft drinks containing fruit juice, such as citrus fruits (grapefruit, oranges, lemons, etc.), fruit pulp drinks and fruit drinks containing fruit particles; tomatoes, green peppers, celery, cucurbits, bitter gourd, carrots, potatoes, asparagus, Foods and beverages containing vegetables such as bracken, Japanese mackerel, vegetable drinks containing these vegetables, vegetable soups, etc.; coffee, cocoa, green tea, black tea, oolong tea, soft drinks, cola drinks, carbonated drinks (various flavors such as citrus flavors) cider etc.), lactic acid bacteria drinks, and other beverages; drinks containing crude drugs and herbs; cola drinks, fruit juice drinks, milk drinks, beer-taste drinks including non-alcoholic beer and so-called "third beer," sports drinks, Functional drinks such as honey drinks, vitamin supplement drinks, mineral supplement drinks, energy drinks, nutrition drinks, lactic acid bacteria drinks; Non-alcoholic beverages such as alcohol-taste drinks with various alcoholic beverages (beer flavor, plum wine flavor, chuhai flavor, etc.) wine, shochu, awamori, sake, beer, chuhai, cocktail drinks, low-malt beer, fruit wine, condiments, other brewed liquors (sparkling) or liqueurs (sparkling), etc., or alcoholic beverages containing these; be able to.

Cosmetics containing vitamin C are not particularly limited, but examples include perfumes such as eau de cologne, eau de toilette, eau de parfum, and parfum; hair care products such as shampoo, conditioner, and hair styling products (hair cream, pomade, etc.); foundation, lipstick, and lipstick. Cosmetics such as creams, lip glosses, lotions, cosmetic emulsions, cosmetic creams, cosmetic gels, serums, and packs; Deodorant products such as antiperspirant sprays, deodorant sheets, deodorant creams, and deodorant sticks; Inorganic salt-based , refreshing, carbonated, skin care, enzyme-based, herbal medicine-based bath additives; tanning cosmetics such as suntan products and sunscreen products; facial cleansers such as face soaps and face creams; body soaps and body soaps. , health and hygiene detergents such as laundry soap, laundry detergent, disinfectant detergent, deodorant detergent, fabric softener, kitchen detergent, and cleaning detergent; health and hygiene materials such as toothpaste, tissue paper, and toilet paper; Examples include aroma products such as deodorizers for rooms and cars, and room fragrances.

In this embodiment, the content of vitamin C contained in the consumer goods is not particularly limited, but for example, the concentration of vitamin C in the consumer goods is 1 ppm to 10 ppm based on the total mass of the consumer goods. %, preferably within the range of 10 ppm to 1%. More specifically, the lower limit is 1 ppm, 10 ppm, 100 ppm, 0.1%, 1%, and the upper limit is 10%, 1%, 0.1%, 100 ppm, 10 ppm. The range can be set within any combination of the lower limit value and the upper limit value, but is not limited thereto.

In addition, as a consumer product containing vitamin C, a drink containing vitamin C is mentioned as a preferable example, and a vitamin C-enriched drink described below is mentioned as a more preferable example. Vitamin C-fortified beverages are those that comply with the requirements for "contains labeling" as stated in the Nutrition Labeling Standards, which is a notification by the Ministry of Health, Labor and Welfare based on the provisions of Article 31, Paragraph 1 of the Health Promotion Act. Specifically, it contains 6 mg (approximately 60 ppm) or more of vitamin C per 100 mL of beverage. In vitamin C-fortified beverages, the upper limit of vitamin C is 1000 mg (approximately 1%) per 100 mL of the beverage, and the preferred range of vitamin C content is 100 mg (approximately 0.1%) or more and 1000 mg (approximately 1%) or less. Regarding the quantitative determination of vitamin C, any method such as HPLC may be used.

Hereinafter, the present invention will be explained in more detail with reference to Examples. Note that the present invention is not limited to these.

[Example 1] Deterioration odor analysis of vitamin C-containing beverages The results of deterioration odor analysis of vitamin C-containing beverages will be described below as an example of vitamin C-containing consumer goods.

A vitamin C-containing beverage (hereinafter referred to as vitamin C-containing beverage) was prepared according to the formulation shown in Table 1. The vitamin C-containing beverage was filled into 100 mL cans, which were rolled up and sealed to produce a vitamin C canned beverage.

The vitamin C canned beverage was (1) stored in the refrigerator (4℃) for one week (hereinafter referred to as the refrigerated product (control product)), (2) stored at room temperature (20 to 28℃) for one week (hereinafter referred to as room temperature). ), (3) stored at 60°C for one week (hereinafter referred to as the product stored at 60°C for one week), (4) stored at 60°C for two weeks (hereinafter referred to as the item stored at 60°C for two weeks). They were stored under four conditions (hereinafter collectively referred to as each stored product of vitamin C canned beverages).

In addition, a drink (vitamin C-free drink) was prepared by removing only vitamin C from the formulation shown in Table 1. The vitamin C-free beverage was filled into 100 mL cans, which were rolled up and sealed to produce a vitamin C-free canned beverage. The vitamin C-free canned beverages were stored under the same four conditions (1) to (4) as the vitamin C canned beverages (hereinafter collectively referred to as stored vitamin C-free canned beverages).

Stored products of vitamin C canned beverages and vitamin C-free canned beverages prepared in the above steps were used in Examples 1-1 and 1-2 below.

[Example 1-1] Measurement of aroma contribution of vitamin C deterioration odor-causing substances Solvent extraction was performed using 50 mL of diethyl ether on 100 g of vitamin C canned beverages stored at 60° C. for 2 weeks. Next, using a concentrate prepared by distilling off the organic solvent from the extract under normal pressure conditions, the aroma contribution was evaluated by AEDA by five well-trained panelists (with over 10 years of experience). The evaluation results are shown in Table 2. In Table 2, the FD (Flavor Dilution) value means the magnification at which the panelists determined that the odor of the evaluation object could not be sensed when the evaluation object was diluted to that ratio. That is, it means that a component with a higher FD value contributes to the aroma of the evaluation target.

As shown in Table 2, it contains the above 1,3-di(furan-2-yl)propan-1-one (the present compound). As mentioned above, the present compound contributes approximately 10 times more to the deterioration odor than furfural and 3-hydroxypyran-2-one, which have been known as components constituting the deterioration odor of vitamin C.

In addition, as shown in Table 2, the contribution of 4-hydroxy-2,5-dimethyl-3(2H)-furanone to the odor of vitamin C deterioration is about 10 times that of furfural and 3-hydroxypyran-2-one. It was found to be high and comparable to that of 1,3-di(furan-2-yl)propan-1-one.

[Example 1-2] Quantitative analysis of vitamin C deterioration odor-causing substances For each stored product of vitamin C canned beverages, 2-chlorophenol was used as an internal standard substance, and the internal standard method was used under the GC analysis conditions shown below. , 3-hydroxypyran-2-one, furfural, 2,5-dimethyl-4-hydroxy-3(2H)-furanone, and 1,3-di(furan-2-yl)propan-1-one. went.

<GC measurement method>
The measurement was performed using GC/MS (device name: GC7890A/MSD5975C, manufactured by Agilent Technologies, Inc.). The GC/MS analysis conditions were as follows.
(GC conditions)
GC column for GC/MS measurement: InertCap-WAX manufactured by GL Sciences (length 60 m, inner diameter 0.25 mm, liquid layer film thickness 0.25 μm)
Temperature increase conditions: 40°C to 230°C, 5.0°C/min temperature increase, 20 min hold Column flow rate: 1.0 mL/min (MS conditions)
Electrical ionization (EI) method, 70eV
Scan range: 50-300
Further, regarding vitamin C, quantitative analysis was performed under the HPLC analysis conditions shown below.

<HPLC measurement method>
The measurement was performed using HPLC/PDA (device name: Prominence/SPD-M20A, manufactured by Shimadzu Corporation).
(HPLC conditions)
Column: Shodex Asahipak NH2P-50 4E (4.6 mmI.D. x 250 mm)
Mobile phase: 20mM NaH2PO4 + 30mM H3PO4 aq. /CH3CN=20/80
Flow rate: 1.0mL/min (detector)
Detection wavelength: 254nm

The analysis results are shown in Table 3. In Table 3, the vitamin C residual rate means the content rate calculated based on the vitamin C content of the refrigerated vitamin C canned beverage (control product) as 100% (reference). In addition, among the results in Table 3, Figure 1 shows a graph summarizing the differences in the amount of 1,3-di(furan-2-yl)propan-1-one produced depending on the storage conditions. FIG. 2 shows a graph summarizing the differences in the amount of 5-dimethyl-3(2H)-furanone produced depending on the storage conditions, and FIG. 3 shows a graph summarizing the differences in the vitamin C residual rate depending on the storage conditions.

As shown in Table 3, 3-hydroxypyran-2-one, furfural, and 4-hydroxy-2,5-dimethyl-3(2H)-furanone, which are known as compounds that are produced when vitamin C deteriorates, are shown in Table 3. In addition, 1,3-di(furan-2-yl)propan-1-one, which was not known to be a compound produced when vitamin C deteriorates, was found in products stored at 60°C for 1 week and products stored at 60°C for 2 weeks. was detected. In addition, 1,3-di(furan-2-yl)propan-1-one is similar to 3-hydroxypyran-2-one, furfural, and 4-hydroxy-2,5-dimethyl-3(2H)-furanone. In addition, the product stored at 60°C for 2 weeks produced more product than the product stored at 60°C for 1 week. And 1,3-di(furan-2-yl)propan-1-one is similar to 3-hydroxypyran-2-one, furfural and 4-hydroxy-2,5-dimethyl-3(2H)-furanone. In addition, among vitamin C-containing beverages, it was hardly detected in refrigerated products, products stored at room temperature, and non-vitamin C-containing beverages.

From the above, it was determined that 1,3-di(furan-2-yl)propan-1-one is a compound produced when vitamin C deteriorates.

[Example 2] Sensory evaluation of the subject compound In order to confirm the contribution to the deterioration odor of each compound detected in the vitamin C-containing beverage in Example 1, 1,3- Beverages of Examples 2-1 to 2-5 were prepared by adding di(furan-2-yl)propan-1-one so that the concentration in the vitamin C-free beverage was as shown in Table 4 below. did. In addition, 3-hydroxypyran-2-one, furfural, and 4-hydroxy-2,5-dimethyl-3(2H)-furanone were added to the vitamin C-free beverage at concentrations shown in Table 4 below. Beverages of Comparative Examples 2-1 to 2-7 were prepared.

The obtained beverages of Examples 2-1 to 2-5 and Comparative Examples 2-1 to 2-7 were subjected to sensory evaluation by 15 well-trained panelists (10 years or more of experience). Sensory evaluation was performed by comparing the flavor of Examples 2-1 to 2-5 and Comparative Examples 2-1 to 2-7 with the control product using a non-vitamin C-containing beverage to which each of the above compounds was not added. The panelists were asked to comment on the differences in the quality of the product, and the scores given by the panelists in accordance with the following evaluation criteria regarding the intensity of deterioration odor compared to the control product were averaged.

<Evaluation criteria regarding deterioration odor intensity>
Significant smell of deterioration compared to control product: 4
Deterioration odor is clearly felt compared to the control product: 3
Slight smell of deterioration compared to the control product: 2
Compared to the control product, there is a very slight smell of deterioration: 1
Equivalent to control product: 0

The results of the sensory evaluation are shown in Table 4 below.

As shown in Table 4, according to Examples 2-1 to 2-5, 1,3-di(furan-2-yl)propan-1-one is recognized as a deterioration odor at a concentration of 3 ppb or more. I understand. Furthermore, when comparing Examples 2-1 to 2-5 and Comparative Examples 2-1 to 2-7, 1,3-di(furan-2-yl)propan-1-one was It was found that the contribution to the deterioration odor was greater than that of 3-hydroxypyran-2-one, furfural, and 4-hydroxy-2,5-dimethyl-3(2H)-furanone, which were thought to be the cause of the odor.

In addition, as shown in Table 4, the aroma of 1,3-di(furan-2-yl)propan-1-one is syrup-like and balsam-like, and 3-hydroxypyran-2-one, furfural and It was found to be easier to distinguish and more characteristic than the aroma of 4-hydroxy-2,5-dimethyl-3(2H)-furanone (brown sugar-like, caramel-like, sugar-like).

From the above points, it was found that the composition containing 1,3-di(furan-2-yl)propan-1-one is excellent as a composition for determining a deterioration odor.

Claims (6)

A composition for determining the deterioration odor of consumer goods containing vitamin C, the composition comprising:
A composition for determining the deterioration odor of consumer goods, containing 1,3-di(furan-2-yl)propan-1-one. A vitamin C pseudo-deterioration odor composition containing 1,3-di(furan-2-yl)propan-1-one. In the vitamin C pseudo-deterioration odor composition according to claim 2,
A pseudo-degraded odor composition of vitamin C, further comprising 4-hydroxy-2,5-dimethyl-3(2H)-furanone. A method for determining deterioration odor of consumer goods containing vitamin C, the method comprising:
A method for determining deterioration odor of consumer goods using 1,3-di(furan-2-yl)propan-1-one as an indicator . A method for evaluating deterioration odor of consumer goods containing vitamin C, the method comprising:
(a) quantifying 1,3-di(furan-2-yl)propan-1-one in the consumer product;
A method for evaluating deterioration odor of consumer goods, including: In the deterioration odor evaluation method according to claim 5,
(b) quantifying 4-hydroxy-2,5-dimethyl-3(2H)-furanone in the consumer product;
A method for evaluating deterioration odor of consumer goods, including:

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