JP2005143370A - Method for suppressing deterioration of citrus flavor - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a method for suppressing the deterioration of citrus flavor of citrus natural essential oil and spice. <P>SOLUTION: This method for suppressing the deterioration of citrus flavor comprises subjecting plant wax to absorption treatment through bringing the citrus natural essential oil or the citrus spice into contact with an absorbent such as a porous absorbent. It is possible to selectively absorb and remove the plant wax as an unvolatile component while removing almost no volatile component essential to citrus flavor by bringing the citrus natural essential oil or the citrus spice into contact with the absorbent, and thus it is possible to suppress the production of uncomfortable smell caused by light and heat while destroying almost no flavor derived from citrus. <P>COPYRIGHT: (C)2005,JPO&NCIPI

Description

  The present invention relates to a method for suppressing deterioration of citrus flavor in citrus natural essential oils and fragrances.

In general, when citrus natural essential oils and fragrances are added to drinks, candy, confectionery and other products, the flavor of the citrus natural oils and fragrances changes over time due to external factors such as light and heat. It is known to deteriorate. Until now, it was thought that the main cause of this deterioration was that terpene compounds such as citral and other volatile components were changed by light and heat. Based on this idea, for example, Non-Patent Document 1 introduces a citrus fragrance from which citral, which is easily deteriorated by light, is removed. Thus, although the device which suppresses deterioration of a citrus flavor conventionally is made | formed, the present condition is that the sufficient flavor deterioration suppression method has not been established yet.
Nozaki Norio, “Recent Soft Drinks”, Fragrance No. 219, September 2003, p.113

  The subject of this invention is providing the deterioration suppression method of the citrus flavor in citrus natural essential oil and a fragrance | flavor.

  As a result of intensive studies to solve the above problems, the present inventors have found that non-volatile components contained in citrus natural essential oils and citrus fragrances, particularly vegetable wax, have a great influence on the deterioration of citrus flavor. A new fact that it is a causative substance was found and the present invention was completed.

  That is, the method for inhibiting deterioration of citrus flavor of the present invention is characterized in that citrus natural essential oil or citrus flavor is brought into contact with an adsorbent.

  According to the present invention, by bringing a citrus natural essential oil or a citrus fragrance into contact with an adsorbent, a vegetable wax that is a non-volatile component is selectively removed without substantially removing volatile components essential to the citrus flavor. Since it can be adsorbed and removed, the generation of unpleasant odor due to light, heat, etc. can be suppressed without substantially impairing the original flavor of citrus fruits.

  Hereinafter, an embodiment of the present invention will be described in detail. In general, natural essential oils are obtained by pressing, solvent extraction, and the like from fruit raw materials. Citrus fruit materials that can be used in the present invention include citrus fruit such as mandarin orange, orange, grapefruit, buntan, lemon, lime, yuzu and kumquat. Citrus natural essential oils obtained by pressing, etc. contain volatile aromatic components such as terpene hydrocarbons, alcohols, and aldehydes, and non-volatile components such as coumarins, furocoumarins, flavonoids, glycosides, and vegetable waxes. It is.

  The method for inhibiting deterioration of citrus flavor according to the present invention comprises bringing the citrus natural essential oil or citrus fragrance such as an essence fragrance obtained from the natural essential oil into contact with an adsorbent (such as a porous adsorbent), thereby bringing about Among them, at least a part of the vegetable wax which is a causative substance of flavor deterioration is removed. Examples of the vegetable wax include β-sitosteryl esters and cholesteryl esters.

  As the adsorbent, for example, activated carbon, cellulose, diatomaceous earth, zeolite or the like can be used. These adsorbents may be in any form such as granular, powdery or massive. The adsorption treatment is performed by adding an adsorbent into the natural essential oil or fragrance and bringing the natural essential oil or fragrance into contact with the adsorbent. At this time, the natural essential oil or fragrance may be diluted with a solvent such as water or alcohol as necessary, and then the adsorption treatment may be performed. The adsorption treatment can be performed batchwise or continuously using a known adsorption device. After the batch-type adsorption treatment, the natural essential oil or fragrance and the porous adsorbent are separated using means such as filtration.

  The vegetable wax content after the adsorption treatment can be adjusted by changing the amount of adsorbent added, the adsorption treatment time, and the like. In order to increase the effect of suppressing flavor deterioration, the content of the vegetable wax in the natural essential oil or fragrance is preferably as low as possible, and preferably the vegetable wax is not substantially contained in the natural essential oil or fragrance. The addition amount of the adsorbent is 1 to 30% by weight, preferably 5 to 10% by weight, based on the citrus natural essential oil or fragrance, and the adsorption treatment time is 30 minutes to 6 hours, preferably 1 to It should be 2 hours.

  Since at least a part of the vegetable wax is removed from the citrus natural essential oil and fragrance obtained by the adsorption treatment, deterioration of the flavor over time due to light, heat, or the like is suppressed. Thereby, generation | occurrence | production of unpleasant odors, such as a bad smell, can be suppressed.

  Moreover, the citrus natural essential oil and fragrance obtained by the above-mentioned adsorption treatment may be added to foods etc. in the same form as usual natural essential oil and fragrance, and forms of blended fragrance blended with other components It may be added to foods. The perfume may be used in the form of powder, granule, paste, solution or the like by subjecting the above-mentioned natural essential oil subjected to adsorption treatment to treatment such as concentration, dilution, filtration, and drying as necessary. When drying into powder or granules, additives such as dextrin may be blended. As a means for drying, for example, means such as hot air drying, freeze drying, drum drying, foam drying, fluidized bed drying and the like can be used. Since the citrus natural essential oil and citrus fragrance obtained by the present invention are obtained from the above fruit raw materials, there is no problem in safety when added to foods and the like.

  Specific examples of foods to which citrus natural essential oil and citrus flavor are added include, for example, soft drinks (carbonated drinks, etc.), juice, coffee, tea, liqueur, milk, whey drink, lactic acid bacteria drinks, candy, chewing gum, chocolate, Examples include gummy, yogurt, ice cream, pudding, bread and confectionery.

  The citrus natural essential oil and citrus fragrance may be added to cosmetics such as perfumes, shampoos, rinses, soaps, bath preparations, lipsticks, and other indoor products as well as the above foods.

EXAMPLES Hereinafter, although a reference example, an Example, and a comparative example are given and this invention is demonstrated further in detail, this invention is not limited to a following example.
[Reference Example 1]

  Lemon was squeezed to obtain lemon oil (citrus natural essential oil), 100 g of this lemon oil was distilled under reduced pressure to remove volatile components, and 1.37 g of a non-volatile fraction was obtained. This non-volatile fraction is known to contain coumarins, flavonoids, glycosides, vegetable waxes and the like. This non-volatile fraction was fractionated into eight fractions (fractions 1-8 in order of decreasing polarity) by normal phase silica gel thin layer chromatography (developing phase hexane: ether = 3: 2), each 0.5% An ethanol solution was obtained. In the thin layer chromatography, “Silica gel 60 F254” manufactured by MERCK was used as a plate. Subsequently, each of the fractions 1 to 8 was mixed with granulated sugar, citric acid and ion-exchanged water at the ratio shown in Table 1 to prepare 8 samples.

These samples were left to stand for 7 days while irradiating light of 2250Lx with a white fluorescent lamp at 5 ° C. After a light resistance test, the experienced panelists sampled the fractions 1, 2, and 3 with low polarity. In each of the samples, the change in flavor was particularly remarkable, and the odor was strong. This flavor was very similar to the characteristic of the odor that appeared when the light resistance test of lemon flavored beverages was conducted.

  Next, 0.5 g of fraction 2 was taken, saponified by alkali treatment, and fractionated into a neutral part and an acidic part. When these neutral and acidic parts were added to a saccharic acid solution and tasted, the neutral part was almost tasteless and odorless, but the flavor of the acidic part was an unpleasant taste that occurred when it deteriorated with heat and light. Was presenting.

The neutral part of these substances is compared with the standard migration rate (Rf value) by thin layer chromatography (TLC), and the acidic part is methylated after gas chromatography (GC) and gas chromatography-mass. As confirmed by analysis (GC-MS), the neutral part was phytosterols mainly composed of β-sitosterol, and the acidic part was a higher fatty acid mainly composed of linoleic acid as shown in Table 2. .

  From these facts, the flavor of citrus natural essential oils deteriorates due to light and heat because irradiation with heat and light in an acidic solution hydrolyzes the vegetable wax in natural essential oils and newly generates higher fatty acids. It is estimated that.

Lemon was squeezed to obtain lemon oil, 5 g of powdered activated carbon was added to 100 g of lemon oil, stirred at room temperature for 2 hours, and filtered to obtain 96 g of lemon oil. Subsequently, the lemon oil before and after the adsorption treatment was analyzed by GC. The analysis conditions for GC are as follows.
Analyzer: Shimadzu 14-B, Class GC-10, manufactured by Shimadzu Corporation
Column: TC-WAX (0.25mm × 60m ID 0.25μm) manufactured by GL Sciences
Column temperature: 80 ° C (5 minutes) to 240 ° C (temperature increase rate 3 ° C / min)
Detector: FID (250 ℃)

  FIG. 1 is a spectrum diagram showing the result of GC analysis of lemon oil before adsorption treatment with activated carbon, and FIG. 2 is a spectrum diagram showing the result of GC analysis of lemon oil after adsorption treatment with activated carbon. 1 and 2, it can be seen that almost no change is observed in the volatile components contained in lemon oil by the adsorption treatment with activated carbon.

In addition, when an expert panelist conducted a sensory test on the scent of lemon oil that had been adsorbed with activated carbon and lemon oil that had not been adsorbed, there was almost no change in the scent of lemon oil before and after the adsorption process. It was confirmed that the later lemon oil had a good citrus flavor.
[Reference Example 2]

  In order to confirm the removal effect of activated carbon by activated carbon, the following test was conducted. First, a solution was prepared by dissolving 0.1% by weight of cholesteryl linoleate, a typical vegetable wax contained in citrus natural essential oil, in hexane. To this solution, powdered activated carbon was added at a ratio of 5% by weight with respect to the total amount of the solution, stirred at room temperature for 2 hours, and then filtered. Next, each solution before and after the adsorption treatment with activated carbon was developed in a developing phase of hexane: ethyl acetate = 19: 1 by normal phase silica gel TLC.

  As a result, a spot of cholesteryl linoleate (Rf value = 0.75) was confirmed in the solution before the adsorption treatment with activated carbon, but the spot of cholesteryl linoleate disappeared in the solution after the adsorption treatment. . This shows that the vegetable wax was removed from the solution by the adsorption treatment.

Lemon was squeezed to obtain lemon oil, and 100 g of this lemon oil was added with 5 g of powdered activated carbon, stirred at room temperature for 2 hours, filtered and adsorbed. Next, 100 g of 60% aqueous ethanol was added to 10 g of lemon oil after the adsorption treatment, and the mixture was stirred for 3 hours. Thereafter, the mixture was allowed to stand, the aqueous layer was fractionated, and filtered to obtain a lemon essence fragrance. Subsequently, the lemon essence flavor, granulated sugar, citric acid and ion-exchanged water were mixed at the ratio shown in Table 3 to prepare a lemon flavored beverage.

<Heat resistance test>
The lemon-flavored beverage obtained was left in a dark place at 45 ° C. for 7 days to conduct a heat resistance test, and then 10 skilled panelists sampled this beverage to find freshness, fruit juice, peel and aroma. A sensory test was conducted on the strength of the. In the sensory test, the score before the heat resistance test was given a maximum of 5 points, and a score was assigned between 1 and 5 points, and the average score of 10 people was obtained.

On the other hand, a lemon flavored beverage (Comparative Example 1) was prepared in the same manner as in Example 2 except that the adsorption treatment with activated carbon was not performed, and a sensory test was performed in the same manner as described above. These results are shown in Table 4.

  From Table 4, it can be seen that the beverage of Example 2 subjected to the adsorption treatment with activated carbon is suppressed in flavor deterioration.

<Light resistance test>
The lemon flavored beverage produced in the same manner as in Example 2 was allowed to stand for 7 days while irradiating light with an illuminance of 2250 Lx with a white fluorescent lamp at 5 ° C. and then subjected to a light resistance test. went. A lemon flavored beverage (Comparative Example 2) was prepared in the same manner as in Example 2 except that the adsorption treatment with activated carbon was not performed, and the light resistance test and the sensory test were performed in the same manner as described above. These results are shown in Table 5.

  From Table 5, it can be seen that the beverage of Example 2 subjected to the adsorption treatment with activated carbon has suppressed the deterioration of flavor.

  Orange was squeezed to obtain orange oil, 5% by weight of powdered activated carbon was added to the orange oil, stirred at room temperature for 2 hours, and filtered to obtain an orange oil adsorbed with vegetable wax.

[Prescription example of blended fragrance]
Using the lemon oil of Example 2 and the orange oil of Example 3 (both oils after adsorption treatment), blended flavorings for lemon candy shown in Table 6 were prepared.

In Example 1, it is a spectrum figure which shows the result of having analyzed the lemon oil before carrying out an adsorption process with activated carbon by GC. In Example 1, it is a spectrum figure which shows the result of having analyzed the lemon oil after carrying out the adsorption process with activated carbon by GC.

Claims (1)

A method for inhibiting deterioration of citrus flavor, comprising bringing citrus natural essential oil or citrus flavor into contact with an adsorbent.

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