JP2014122187A - Production inhibitor of citral deterioration product, and production inhibition method - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a production inhibitor of a citral deterioration product and a production inhibition method, where generation of a degradation odor can be suppressed and significant quality reduction of a citral-containing composition can be prevented, by inhibiting production of a degradation odor-causing substance (citral deterioration product) from citral produced particularly by heating or passing of time in citral or a citral-containing composition.SOLUTION: As a production inhibitor of a citral deterioration product, a pine-needle extract or a composition having it as an active ingredient is used.

Description

  The present invention relates to a production inhibitor for citral degradation products and a production inhibition method. More specifically, in a citral or a composition containing citral, generation of a compound (citral deteriorated product) caused by deterioration of citral due to heating or change with time is suppressed, and a deteriorated odor generated from the citral deteriorated product (off-note) The present invention relates to a preparation and a method for inhibiting the above.

  Citral is an essential oil component present in lemon peels, lemongrass and the like, and is useful as a component of citrus fragrance because it has a fresh lemon-like aroma. However, it is known that citral undergoes various deterioration reactions under the influence of heat and light, and in particular, the deterioration reaction is likely to occur under the acidic conditions employed in citrus beverages. Such citral deterioration reduces and disappears the lemon-like fragrance peculiar to citral, and at the same time, deteriorated odor caused by a compound produced by citral deterioration (this is referred to as “citral deteriorated product” in the present invention). (Off note) occurs. Among the citral degradation products, p-methylacetophenone and p-cresol produced by thermal degradation have a low odor threshold, so the quality of products containing citral is significantly improved even in small amounts. It causes a decrease.

  For this reason, conventionally, a method for preventing the generation of a deterioration odor by suppressing the heat deterioration and light deterioration reaction of citral has been studied. Specifically, antioxidants such as BHT, BHA, and α-tocopherol have no effect on p-cymene, α, p-dimethylstyrene and p-cymen-8-ol produced by thermal degradation of citral ( Non-patent document 1); On the other hand, it has been reported that ascorbic acid and isoascorbic acid are effective in suppressing the formation of α, p-dimethylstyrene and p-cymen-8-ol (non-patent document 2). Recently, catechins derived from green tea and theaflavins, which are polyphenol components contained in black tea, have been used to suppress the production of p-cresol. It has been reported that theaflavins are effective (Non-patent Document 3). For photodegradation of citral, UV absorbers, especially substances having absorption in the UV-A region (320-400 nm) such as rutin and chlorogenic acid, and radical scavengers such as ascorbic acid are effective. Have been reported (Non-Patent Documents 4 and 5).

  In addition, as a method for suppressing the generation of citral deterioration odor, at least one solvent extract selected from the group consisting of tomorrow, avocado, psyllium, semi-fermented tea leaves, Ebisu rush, and hawthorn; Or extract extracted from cacao; solvent extract from Labiatae Menta mint, Asteraceae Artemisia mugwort, Citrus subfamily Citrus orange, Citrus subfamily Citrus lemon, Citrus subfamily Citrus grapefruit , As a deteriorated odor production inhibitor (Patent Documents 1 to 3), tea extract components, especially products obtained by treating the extract components of Camellia and sinensis with oxidase enzymes (Patent Document 4) used as a citral or citral-containing product Method for inhibiting the generation of deterioration smell components derived from citral by the inclusion of transition metal ions (patent document 5) is known as.

JP 2008-280539 A JP 2002-180081 A JP 2002-255778 A International Publication WO2009 / 011271 Pamphlet JP 2004-123788 A

K. Kimura, et al., J. Agric. Food Chem., 31, 801-804 (1983) V. E. Peacock, et al., J. Agric. Food Chem., 33, 330-335 (1985) T. Ueno, et al., J. Agric. Food Chem., 54, 3055-3061 (2006) Inaba Osamu; Monthly Food Chemical, 13 (7), 23-27 (1997) H. Tateba, et al., Royal Society of Chemistry, Cambridge, U.K., 1996, pp.82-85

  In view of the problems in the prior art described above, the present invention, particularly in citral or citral-containing compositions, suppresses the generation of a detrimental odor-causing substance (citral deteriorated product) derived from citral that is generated particularly with heating or over time. It aims at providing the production | generation inhibitor and production | generation suppression method of a citral degradation product which can suppress generation | occurrence | production of a degradation odor and can prevent the remarkable quality fall of a citral containing composition.

  In order to solve the above problems, the present inventors have studied a method for suppressing deterioration of citral by heating. By adding a pine needle extract to citral or a citral-containing composition, a main causative substance of a deteriorated odor is obtained. It was found that the production of p-methylacetophenone, which is In addition, the present inventors have confirmed that according to the pine needle extract, the production of p-methylacetophenone, which is a causative substance of a deteriorated odor produced when citral is stored for a long time, can be significantly suppressed.

  The present invention has been completed based on such knowledge, and includes the following embodiments.

(I) Citral degradation product inhibitor (I-1 ) A citral degradation product produced by heating citral or a citral-containing composition or by aging of citral or a citral-containing composition, A citral degradation product production inhibitor characterized by comprising a product as an active ingredient.
(I-2) The citral degradation product formation inhibitor described in (I-1), wherein the citral degradation product is p-methylacetophenone.
(I-3) The citral-containing composition is any one selected from the group consisting of a fragrance composition containing citral, a food and beverage composition, a cosmetic composition, and daily necessities, (I-1) or The citral degradation product formation inhibitor described in (I-2).

  Here, “degraded citral produced by aging” means degradation caused by citral alteration (deterioration) when citral or a citral-containing composition is stored at room temperature (20 ° C.) or higher. It means a compound that causes odor.

(II) A citral-containing composition comprising the citral-containing product inhibitor according to any one of (II-1) (I-1) to (I-3).
(II-2) The citral-containing composition described in (II-1), which is any one selected from the group consisting of a fragrance composition containing citral, a food and drink composition, a cosmetic composition, and daily necessities.

(III) Method for inhibiting citral degradation product generation (III-1) A method for inhibiting citral degradation products produced by heating citral or a citral-containing composition, or by aging of citral or a citral-containing composition, A method for inhibiting citral degradation or production of citral deterioration in a citral-containing composition, comprising blending a pine needle extract with the citral-containing composition.
(III-2) The method for inhibiting citral degradation product formation according to (III-1), wherein the citral degradation product is p-methylacetophenone.
(III-3) The citral-containing composition is any one selected from the group consisting of a fragrance composition containing citral, a food and beverage composition, a cosmetic composition, and daily necessities, (III-1) or ( The method for inhibiting citral degradation products described in III-2).

  By using the citral deterioration product formation inhibitor of the present invention added to citral or a citral-containing composition, generation of a compound (citral deterioration product) generated by deterioration of citral over time or by heating is suppressed, As a result, generation | occurrence | production of the deterioration odor caused by a citral deterioration thing can be suppressed. In particular, the citral degradation product production inhibitor and the citral degradation product production inhibition method of the present invention are excellent in the production inhibition effect of p-methylacetophenone, which is the main causative substance of the degradation odor among the citral degradation products.

  Due to the effects of the present invention, citral or a composition containing citral containing a citral degradation product inhibitor (fragrance composition, food / beverage composition, cosmetic composition, daily necessities, etc.) is manufactured, distributed, or Generation | occurrence | production of the deterioration odor which may arise with time in preservation | save is significantly suppressed, As a result, the citral containing composition which does not impair aroma with a deterioration odor over a comparatively long period can be provided.

In Experimental Example 1, the citral solution was obtained at 40 ° C. or 50 under the coexistence conditions of the pine needle extract (0% to 95% ethanol extract was added in an amount of 5 to 60 ppm in terms of solid amount) or under the non-coexistence conditions (blank). The result of having measured the production amount of p-methylacetophenone after storing at 3 degreeC for 3 days is shown.

(I) Citral degradation product production inhibitor The citral degradation product production inhibitor of the present invention is characterized by comprising a pine needle extract as an active ingredient.

  The pine needle used as the material for the pine needle extract may be a leaf of a plant (pine) belonging to the genus Pinaceae, and the type of pine is not particularly limited. For example, Pinus albicaulis, Pinus aristata, Pinus attenuata, Pinus balfouriana, Banks pine (Pinus banksiana), European pine (Pinus cembra), Pinus cembroides, Pinus clam Pinus contorta, Pinus coulteri, Pinus densiflora, Epine pine (Pinus echinata), Pinus edulis, Pinus elliottii, Pinus engelmannii, Pinus flexilisbra, Pinus held pine ), Pinus jeffreyi, sugar pine (Pinus lambertiana), bristle corn pine (Pinus longaeva), red pine (Pinus massoniana), American pine (Pinus monophylla), American pine (Pinus monticola), Montana pine (Pinus mugo) Bishop pine (Pinus muricata), European pine (Pinus nigra), Japanese pine (Pinus palustris), Go Pinus parviflora, Pinus pungens, Pinus quadrifolia, Pinus radiata, Pinus resinosa, Pinus rigida, Pinus sabiniana, Pinus serotina, Pinus strobiformis, St. pine sylvestris), Pinus tabulaeformis, Pinus taeda, Pinus thunbergiana, Pinus torreyana, Virginia pine (Pinus virginiana), Pinus yuannensis, and Pinus washoensis. Preferably, mention may be made of plants belonging to red pine, such as Pinus densiflora, Pinus massoniana, Pinus tabulaeformis, and Pinus sylvestris. More preferred are red pine and Thai one pine.

  Red pine (Pinus densiflora Sieb. Et Zuee. [Japanese red pine]) leaves have been used as a preventive and therapeutic drug for rheumatism, beriberi and frostbite.

  The pine needles may be subjected to the extraction operation as they are (raw) or as a crushed material, or may be subjected to the extraction operation as pulverized or powdered as necessary after drying. Note that the dried pine needle powder can be obtained commercially.

  Examples of the extraction solvent include water, an organic solvent, or a mixture thereof. Although it does not restrict | limit especially as an organic solvent, For example, according to the kind of the object to which the citral degradation thing generation | occurence | production inhibitor of this invention is applied, it is C1-C4 low, such as methanol, ethanol, propanol, and butanol Alcohol; lower alkyl ester such as ethyl acetate; glycols such as ethylene glycol, butylene glycol, propylene glycol, and glycerin; and other polar solvents such as ethyl ether, acetone, and acetic acid. These solvents may be used alone or in combination of two or more. For example, if necessary, an appropriate amount of water can be added to the organic solvent to use it as a water-containing organic solvent, and examples thereof include a mixed solvent of water and a lower alcohol.

  In the present invention, the extraction solvent is more preferably water, a lower alcohol (preferably ethanol), or a mixed solution of water and a lower alcohol (preferably ethanol). An aqueous solution can be exemplified. The ethanol content in the ethanol-containing aqueous solution is preferably about 20 to 98% by volume, more preferably about 30 to 98% by volume, still more preferably about 40 to 98% by volume, and still more preferably about 50 to 98% by volume. Particularly preferably, it is about 60 to 98% by volume, particularly preferably about 70 to 98% by volume.

  As the extraction method, generally used methods can be adopted, and for example, extraction methods used for the preparation of various herbal preparations such as extracts, elixirs, soaking / decoction, flow extract and tincture can be widely cited. Although it is not limited, for example, the above-mentioned pine needles (as it is (raw) or coarse powder, shredded products) or their dry crushed materials (powder, etc.) are subjected to cold immersion (normally 1 to 25 ° C.) or digestion (normally 35-45 ° C), a method of performing extraction while heating and stirring, a method of obtaining an extract by filtration, a percolation method (usually about 1-30 ° C), and the like.

  The obtained extract may be used as it is, after removing solids by filtration or centrifugation as necessary, or may be used as it is, or partially concentrated by distilling off the solvent to obtain a soft extract or reduced pressure. It can also be used as a dried extract by drying by ordinary means such as drying or freeze-drying. Further, after concentration or drying, the resulting concentrate or dried product may be used after being purified by washing with an insoluble solvent, or may be used by further dissolving or suspending it in an appropriate solvent.

  The pine needle extract thus prepared can be used as it is as a citral degradation product inhibitor of the present invention by adding and blending it into citral or a citral-containing composition, but it can also be used by formulating it. it can.

  The formulation method is not particularly limited, but for example, a method of dissolving in a desired solvent such as water, an organic solvent (alcohol, glycerin, propylene glycol) or a mixture thereof to form a liquid; an excipient such as dextrin in the liquid Method of blending into a paste-form preparation; Method of further granulating or tableting the paste-form preparation into granules or tablets; Spray-drying or freeze-drying the above solution to form a powder-form preparation (powder preparation) Method: Further, a method of preparing an emulsion preparation by adding oils and fats together with an emulsifier to the above liquid agent to disperse and emulsify can be mentioned, and a desired dosage form can be appropriately selected and adopted depending on the application.

  The citral-containing composition to which the citral degradation product formation inhibitor of the present invention is applied is a composition containing citral as an aroma component, and includes a citral-containing fragrance composition, a citral-containing food and beverage composition, and a citral-containing cosmetic composition. And citral-containing daily necessities.

  Examples of the citral-containing fragrance composition include citrus, particularly citrus fragrance preparations. Although it does not restrict | limit as a citral containing food-drinks composition, carbonated drinks, fruit juice drinks, milk drinks, soft drinks, citrus drinks, such as a tea drink; Citrus drinks, such as strawberry high and a cocktail; Yogurt, jelly, ice Citrus confectionery such as cream; citrus confectionery such as candy, gum, chocolate, and baked confectionery; Examples of the citral-containing cosmetic composition include citrus-based cosmetics such as basic cosmetics, funny, foundations, lipsticks, perfumes, and body cosmetics. In addition, citral-containing daily products include citrus oral care products such as mouthwashes and toothpastes; citrus detergents such as laundry detergents, kitchen detergents, toilet cleaners, and bathroom detergents; body care products (solid soaps, hands Soap, body soap, etc.), skin care products (hand cream, lip balm, sunscreen cream, antiperspirant, moisturizing pack, etc.), hair care products (shampoo, conditioner, hair color, hair spray, hair wax, hair restorer, etc.), Citrus daily necessities such as bathing agents, aroma products, and fragrances can be exemplified.

  The citral content in these citral-containing fragrance compositions may be at least the citral odor threshold, specifically 100 ppt or more, preferably at least 1 ppb, more preferably at least 5 ppb, It can be set appropriately according to the purpose.

  As a blending ratio of the citral deterioration product inhibitor of the present invention to be blended with these citral or the citral-containing composition, in the citral or citral-containing composition, the ratio of the generation of the citral degradation product that is the effect of the present invention can be suppressed. There is no particular limitation as long as it is sufficient. For example, when the blending amount of the citral degradation product formation inhibitor of the present invention is converted into a ratio of the pine needle extract as the active ingredient (in solid matter), the final concentration in the citral or citral-containing composition is 1 ppm or more. The ratio is preferably 2 ppm or more, more preferably 5 ppm or more. The upper limit is not particularly limited because the amount of the citral degradation product production inhibitor (pine needle extract) tends to suppress the generation of the citral degradation product, and the practicality of the citral-containing composition and It can be set appropriately from the viewpoint of economy and the like. For example, when the citral-containing composition is a fragrance composition, the blending amount of the citral degradation product generation inhibitor is in the range of 1 to 50,000 ppm in terms of the ratio of pine needle extract (in terms of solid matter), and so on. In the case of a food / beverage composition, it can be set and adjusted as appropriate from the range of 1 to 200 ppm, in the case of a cosmetic composition, in the range of 1 to 500 ppm, and in the case of daily necessities.

  Moreover, as a ratio of the citral degradation product generation inhibitor with respect to the amount of citral contained in citral or a citral-containing composition, when converted to a ratio of pine needle extract (in terms of solids), 2 masses per 1 mass part of citral Part or more, preferably 5 parts by weight or more.

  In the present invention, the “degraded citral product” is a compound that citral is decomposed and produced over time or by heating, and particularly includes a compound that causes a degradation odor. Preferable examples include p-methylacetophenone, which has a low odor threshold of about 2.7-10.8 ng / L air and is known as a deteriorated odor of citral.

(II) Citral-containing composition The citral-containing composition of the present invention contains the above-mentioned citral degradation product formation inhibitor, so that generation of citral degradation products caused by citral degradation over time or by heating is suppressed, The composition is characterized in that the generation of a deterioration odor caused by a deteriorated citral product is suppressed.

  Here, the “citral deteriorated product” is a compound which citral is decomposed and formed over time or by heating as described above, and particularly includes a compound which causes a deterioration odor. P-methylacetophenone is preferred.

  The citral-containing composition of the present invention is a composition containing citral as an aroma component, and can include citral-containing fragrance compositions, citral-containing food and beverage compositions, citral-containing cosmetic compositions, and citral-containing daily necessities. . Details of these compositions are as described above in (I) above. More preferably, it is a citral-containing fragrance composition and a citral-containing food or drink composition.

  The citral content in these citral-containing fragrance compositions may be at least the citral odor threshold, specifically 100 ppt, preferably at least 1 ppb, more preferably at least 5 ppb. It can be set appropriately according to the purpose.

  The ratio of the citral degradation product generation inhibitor contained in the citral-containing composition of the present invention should be a ratio that can suppress the generation of the citral degradation product that is the effect of the present invention by including the citral degradation product generation inhibitor. There is no particular limitation as long as it is limited. For example, when the concentration of the citral degradation product inhibitor in the citral-containing composition is converted to the ratio of the pine needle extract as the active ingredient (in terms of solids), 1 ppm or more, preferably 2 ppm or more, more preferably 5 ppm. Can be mentioned. The upper limit is not particularly limited because the amount of the citral degradation product production inhibitor (pine needle extract) tends to suppress the generation of the citral degradation product, and the practicality of the citral-containing composition and It can be set appropriately from the viewpoint of economy and the like. For example, when the citral-containing composition is a fragrance composition, the blending amount of the citral degradation product generation inhibitor is in the range of 1 to 50,000 ppm in terms of the ratio of pine needle extract (in terms of solid matter), and so on. In the case of a food / beverage composition, it can be set and adjusted as appropriate from the range of 1 to 200 ppm, in the case of a cosmetic composition, in the range of 1 to 500 ppm, and in the case of daily necessities.

  Moreover, as a ratio of the citral degradation product production | generation inhibitor with respect to the quantity of citral contained in a citral containing composition, when converted into the ratio of pine needle extract (solid substance conversion), 2 mass parts or more with respect to 1 mass part of citral, Preferably 5 mass parts or more can be mentioned.

(III) Method for inhibiting citral degradation product formation The method for inhibiting citral degradation product production of the present invention is characterized by blending a pine needle extract with citral or a citral-containing composition.

  As for the pine needle extract used here, the kind and shape of the pine needle used as the material, the extraction method of the pine needle extract, the state and the form of the pine needle extract are all as described in the above (I), The description of I) can be used.

  The citral-containing composition to which the method of the present invention is applied is a composition containing citral as an aroma component, and includes a citral-containing fragrance composition, a citral-containing food / beverage composition, a citral-containing cosmetic composition, and a citral-containing daily product Can be mentioned. The details are as described in the above (I), and the description of (I) can be used.

  The blending ratio of the pine needle extract to be blended with these citral or citral-containing fragrance composition may be any ratio that can suppress the generation of a citral deteriorated product that is an effect of the present invention in the citral or citral-containing composition. As long as it is not particularly limited. For example, the ratio which the final density | concentration of the pine needle extract in a citral or a citral containing composition will be 1 ppm or more in conversion of a dry matter, Preferably it is 2 ppm or more, More preferably, it can mention 5 ppm. The upper limit is not particularly limited because the amount of the citral degradation product production inhibitor (pine needle extract) tends to suppress the generation of the citral degradation product, and the practicality of the citral-containing composition and It can be set appropriately from the viewpoint of economy and the like. For example, when the citral-containing composition is a fragrance composition, the blending amount of the citral degradation product generation inhibitor is in the range of 1 to 50,000 ppm in terms of the ratio of pine needle extract (in terms of solid matter), and so on. In the case of a food / beverage composition, it can be set and adjusted as appropriate from the range of 1 to 200 ppm, in the case of a cosmetic composition, in the range of 1 to 500 ppm, and in the case of daily necessities.

  Moreover, as a ratio of the pine needle extract with respect to the quantity of citral contained in citral or a citral containing composition, it is 2 mass parts or more with respect to 1 mass part of citral in conversion of solid, Preferably 5 mass parts or more can be mentioned. .

  In the method of the present invention, “degraded citral product” is a compound that citral is decomposed and produced over time or by heating as described above, and particularly includes compounds that cause a degradation odor. For example, p-methylacetophenone.

  EXAMPLES Hereinafter, although this invention is demonstrated further in detail based on an experiment example and an Example, this invention is not restrict | limited at all by these Examples.

Experimental Example 1 p-Methylacetophenone Production Inhibition Test Various test samples were added to a citral-containing acid sugar solution (pH 3) and stored at 40 ° C. or 50 ° C. in a thermostatic chamber. After storage, the citral-containing acid sugar was analyzed by HPLC. The production amount of p-methylacetophenone (p-MAP) in the liquid was measured, and the p-MAP production inhibitory action of the test sample was evaluated.

(1) Preparation of test sample Hydrous ethanol containing 100% dry powder of Tokushima red pine (Pinus densiflora) leaves with water (0% EtOH) or ethanol in a proportion of 10, 30, 50, 70 or 95% by volume 800 g of (10% EtOH, 30% EtOH, 50% EtOH, 70% EtOH, 95% EtOH) was blended and extracted at 70 ° C. for 5 hours with stirring. After extraction, solid-liquid separation was performed to remove solids (extraction residue), and a pine needle extract was obtained. This was used as a test sample.

  In addition, each test sample measured dry solid content with the infrared moisture meter (made by Kett Scientific Laboratory).

(2) The formulation of the citral-containing acid sugar solution used for the preparation test of the citral-containing acid sugar solution is shown below.

Each component shown below was blended at the following ratio, and prepared with water to 100 mass%.
<Prescription of citral-containing acid sugar solution>
Fructose glucose liquid sugar 13% by mass
Citric acid 0.2% by mass
Adjust to pH 3 with 3Na citrate
1% citral 0.5% by mass
100% by mass in water.

(3) Test Method After putting 40 g of the above-mentioned citral-containing acid sugar solution into a 50 mL glass screw tube, various test samples (0% EtOH extract, 10% EtOH extract, 30% EtOH extract, 50% EtOH extraction) Liquid, 70% EtOH extract, and 95% EtOH extract) were added at a rate of 5 to 60 ppm in terms of dry solids. This was stored for 3 days in a thermostat at 40 ° C. or 50 ° C. After storage, the sample was allowed to cool to room temperature. After cooling, the sample was subjected to HPLC under the following conditions to measure the amount of p-MAP produced. In addition, as a comparative test, a sample (control) in which 40 g of citral-containing acid sugar solution as it is without storage of a test sample is stored in a refrigerated light-shielded state (control) and a sample (blank) stored in a thermostatic chamber at 40 ° C. or 50 ° C. for 3 days. Was similarly subjected to HPLC, and the amount of p-MAP produced was measured. The amount of p-MAP produced was determined as the peak area in the HPLC chromatogram.

<HPLC measurement conditions>
Column: Cadenza CD-C18, 4.6 x 150 mm (Imtakt)
Mobile phase: Isocratic elution flow rate of liquid A (0.1% phosphoric acid aqueous solution) 55% and liquid B (acetonitrile) 45%: 1.0 ml / min
Detection wavelength: 254 nm
Column temperature: 40 ° C
Sample injection volume: 20 μl.

(4) The results of the test are shown in Table 1 and FIG.

  As can be seen from this result, by adding the pine needle extract to the citral-containing acid sugar solution, it is possible to suppress the production of p-MAP, which is a causative substance (degraded citral) of the odor caused by heating. The effect depends on the dose of the pine needle extract to be added, and the pine needle extract contains ethanol at a high concentration of, for example, 50% by volume or more, preferably 70% by volume or more, more preferably 90% by volume or more. It was confirmed that it is preferable to use an extract extracted from pine needles with hydrous ethanol.

Example 1 Fragrance preparation (orange fragrance)
The following ingredients were mixed at the following prescription ratio (mass%) to prepare a fragrance preparation (orange fragrance) which was dissolved by stirring and hardly deteriorated. In addition, among the following ingredients, citral is contained in orange oil and lemon oil (total amount of citral in the fragrance preparation is 0.0002%)
Orange oil 7.00 (mass%)
Orange juice 2.00
Lemon oil 1.00
Pine leaf extract (50% EtOH extract: solid content 3.5%) 5.00
L-ascorbic acid 0.04
95% ethanol 50.00
Ion exchange water 34.96
Total 100.00%.

Example 2 Fragrance preparation (grapefruit fragrance)
The following components were mixed at the following prescription ratio (mass%) to prepare a fragrance preparation (grapefruit fragrance) which was dissolved by stirring and hardly deteriorated. In addition, among the following components, citral is contained in orange oil and lemon oil (total amount of citral in the fragrance preparation 0.0005%)
Grapefruit oil 3.0 (mass%)
Orange oil 1.5
Orange essence 0.3
Lemon oil 0.2
Concentrated apricot flavor 5.0
Pine needle extract (70% EtOH extract: solid content 3.6%) 7.0
95% ethanol 37.0%
Orange tincture 42.0
Ion exchange water 6.0
Total 100.0%.

Example 3 Fragrance preparation (lemon fragrance)
The following ingredients were mixed at the following prescription ratio (mass%) to prepare a fragrance preparation (lemon fragrance) which was dissolved by stirring and hardly deteriorated. In addition, among the following components, citral is also contained in orange oil and lemon oil (total amount of citral in the fragrance preparation 0.055%)
Orange oil 20.50 (mass%)
Lemon oil 10.00
Citral 0.05
Geranyl acetate 0.20
Linalool 0.10
95 vol% ethanol 64.15
Pine needle extract (50% EtOH extract: solid content 3.5%) 5.00
Total 100.00%.

Example 4 Beverage Concentrated Orange Juice with Orange Juice 4.40 (mass%)
Fructose glucose liquid sugar 6.00
4.00 sugar
Citric acid 0.15
Trisodium citrate 0.02
L-ascorbic acid 0.03
Orange flavor of Example 1 0.10
100.00% total with ion-exchanged water
It was confirmed that the beverage containing orange juice of Example 4 significantly suppressed the deterioration odor after storage at 40 ° C. for 1 month, compared with the beverage containing orange juice without the pine needle extract added.

Example 5 Flavored water (lemon flavor)
Fructose glucose liquid sugar 6.00 (mass%)
Sugar 2.00
Citric acid 0.18
Trisodium citrate 0.02
Lemon flavor of Example 3 0.05
100.00% total with ion-exchanged water
It was confirmed that the flavor water (lemon flavor) of Example 5 significantly suppressed the deterioration odor after storage at 40 ° C. for one month, as compared with the flavor water (lemon flavor) to which no pine needle extract was added. .

Example 6 Lotion 95% by volume Ethanol 10.0 (mass%)
POE (60) hydrogenated castor oil 2.0
Methylparaben 0.1
Perfume (containing citral) 0.1
Glycerin 10.0
Pine leaf extract (50% EtOH extract: solid content 3.5%) 5.0
Ion exchange water 72.8
Total of 100.0% with ion-exchanged water
It was confirmed that the skin lotion of Example 6 significantly suppressed the deterioration odor after storage at room temperature for 6 months, compared with the skin lotion to which no pine needle extract was added.

Example 7 Mouthwash 95 volume% ethanol 10.0 (mass%)
Glycerin (85%) 10.0
Propylene glycol 2.0
Citric acid 3.0
Sodium citrate 6.0
Xylit 3.0
Poly (oxyethylene) (20) cetyl ether 2.0
Dextranase 0.1
Sodium fluoride 0.2
Saccharin sodium 0.1
Sodium benzoate 0.2
Perfume (containing citral) 0.7
Pine needle extract (30% EtOH extract: solid content 3.2%) 6.0
Total of 100.0% with ion-exchanged water
It was confirmed that the mouthwash of Example 7 significantly suppressed the deterioration odor after storage at room temperature for 6 months, compared with the mouthwash without addition of pine needle extract.

Example 8 Dentifrice Silicic Acid 10.0 (mass%)
Sorbitol solution (70%) 35.0
Saccharin sodium 0.2
Glycerin 15.0
Polyethylene glycol 6.0
Thickening silica 3.5
Xanthan gum 0.2
Carrageenan 0.2
Carboxymethylcellulose 0.6
Sodium lauryl sulfate 1.5
Perfume (containing citral) 1.0
Pine leaf extract (50% EtOH extract: solid content 3.5%) 4.0
100.0% with deionized water
It was confirmed that the dentifrice of Example 8 significantly suppressed the deterioration odor after storage at room temperature and 6 months, compared with the dentifrice additive-free dentifrice.

Claims (8)

A citral or citral-containing composition is heated, or a citral degradation product produced by aging of a citral or a citral-containing composition, characterized by comprising a pine needle extract as an active ingredient, Citral degradation product inhibitor for citral-containing compositions. The citral degradation product production inhibitor according to claim 1, wherein the citral degradation product is p-methylacetophenone. The citral-containing product produced according to claim 1 or 2, wherein the citral-containing composition is any one selected from the group consisting of a fragrance composition containing citral, a food and drink composition, a cosmetic composition, and daily necessities. Inhibitor. A citral-containing composition containing the citral degradation product production inhibitor according to any one of claims 1 to 3. The citral-containing composition according to claim 4, which is any one selected from the group consisting of a fragrance composition containing citral, a food / beverage composition, a cosmetic composition, and daily necessities. A method for suppressing a citral or a citral-degraded product produced by heating a citral or a citral-containing composition or a change over time of the citral or a citral-containing composition, wherein a pine needle extract is blended with the citral or the citral-containing composition And a method for suppressing citral degradation products. The method for inhibiting citral degradation product formation according to claim 6, wherein the citral degradation product is p-methylacetophenone. The citral-containing product produced according to claim 6 or 7, wherein the citral-containing composition is any one selected from the group consisting of a fragrance composition containing citral, a food and drink composition, a cosmetic composition, and a daily necessities. Suppression method.

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