KR101799027B1 - Perfume composition for expressing the fragrance of Citrus unshiu of Jeju island the composition for skin external application containing the same - Google Patents

Abstract

The present invention Jeju citrus flowers (Citrus The present invention relates to a perfume composition recreating the fragrance of unshiu and to a composition for external application for skin containing the fragrance composition. More particularly, the present invention relates to a composition for external application for skin containing Jeju citrus floral fragrance analyzed by SPME (Solid Phase Micro Extraction) The present invention also relates to a composition for external application for skin containing the perfume composition.

Description

TECHNICAL FIELD [0001] The present invention relates to a perfume composition recreating the fragrance of a citrus flower of Jeju Island and a composition for external application for skin containing the fragrance composition for expressing the fragrance of Citrus unshiu,

The present invention Jeju citrus flowers (Citrus The present invention relates to a perfume composition recreating the fragrance of unshiu and to a composition for external application for skin containing the fragrance composition. More particularly, the present invention relates to a composition for external application for skin containing Jeju citrus floral fragrance analyzed by SPME (Solid Phase Micro Extraction) The present invention also relates to a composition for external application for skin containing the perfume composition.

Generally, "citrus" refers to plants belonging to the citrus, citrus, Fortunella and Poncirus of the Rutaceae auranti- oideae. Citrus plants are distributed in Southeast Asia and its surrounding islands, including India and China, the Australian continent, and the African continent, and do not exist in the continental continent or the Americas. Korea is located in the northern most citrus plantation area in the world. Jeju Island, Tongyoung, Geoje and Namhae are the southern coasts of the peninsula. Among them, Jeju Island is the most delicious citrus production area.

Citrus tree is an evergreen broad-leaved arboreous tree, with leaves lanceolate, lanceolate or broad lanceolate, dull, ovate, 5-7 cm long, 5 cm wide, with plain edges, wavy sawtooth, and winged or winged leaves. The stem is straight but has many branches, the bark is brown, it is chopped and there are no thorns on the branches. The fruit is circular, 3 ~ 4cm in diameter, ripened in orange or yellowish red in October, the peel is well separated from the pulp, the center is empty and divided into 9 ~ 10 yarns. The outer skin is smooth and has a shiny finish. The fruit is edible, and the pericarp is called the dermis in one side, and it is used for the cold and so on. The flower is white, bloomed from May to June, and it is single, with a flower length of 2㎝, small and distinctive with a dark scent.

From ancient times, it has been used as the finest noble fragrance by extracting the fragrance of orange flower in various ways and making it into perfume. It is also used as an aromatherapy in Europe for effects such as antidepressants, sterilization, aphrodisiacs, deodorization, nerve stimulation or tonic effects, and dried flowers have also been used to stimulate the nervous system or purify the blood. However, the citrus tree of Jeju Island has been used only as an edible fruit and is not used as a perfume material. However, the citrus flowers that grow in the clean air of Jeju Island have sweet and fresh flowers that are different from the orange flowers, and their importance as domestic spice materials has been highlighted.

In general, there are various methods for reproducing the fragrance of natural products. For example, there are a solvent extraction method which makes the fragrance component into an absolute form and a steam distillation method which makes the fragrance component into essential oil. However, since the above methods require high heat during the extraction process and the processing is complicated and takes a long time, there may be many differences from the original flavor.

The present inventors analyzed the fragrance components by the SPME method to reproduce the fragrance of the citrus flower of Jeju Island and found that Myrcene, Phenylacetaldehyde oxime and Indole are the main components of the citrus flower fragrance of Jeju Island Respectively.

In addition, the present inventors have found that a perfume composition containing the main component of the Jeju Island citrus flower fragrance and methyl anthranilate, which is a characteristic fragrance component representing Jeju Island citrus flower, can reproduce the intrinsic fragrance of the Jeju Island citrus flower as it is And thus the present invention has been completed.

Accordingly, an object of the present invention is to provide a perfume composition having excellent palatability while reproducing intrinsic fragrance of citrus flowers of Jeju Island.

Another object of the present invention is to provide a skin external preparation containing the above-mentioned perfume composition.

In order to achieve the above object, the present invention provides a composition comprising 60 to 70% by weight of a perfume ingredient composed of myrcene, phenylacetaldehyde oxime and indole in a total weight of the composition, A fragrance composition recreating the fragrance of flowers is provided.

The perfume composition according to the present invention contains the main component of the citrus flower fragrance of Jeju Island analyzed by the SPME method in a specific amount and further added with methyl anthranilate to reproduce the intrinsic fragrance of the citrus flower of Jeju Island as it is, The palatability of the present invention can be improved.

Hereinafter, the present invention will be described in more detail.

In the present invention, SPME (Solid Phase Micro Extraction; SUPELCO international, Vol.13, No.4, p.9-10) was used to analyze the fragrance components of citrus flowers in Jeju Island. Unlike the conventional extraction method, this SPME method does not use a solvent and does not require a pretreatment, and thus it is possible to quickly and easily analyze a flavor component. In addition, the SPME method can analyze the fragrance components of the volatile citrus flowers of Jeju Island because the fractions adsorbed on the fiber can be rapidly desorbed and injected into the GS-MS column without special pretreatment, It is advantageous. In the present invention, based on the fragrance components of citrus flowers of Jeju Island analyzed by SPME method, a combined fragrance was prepared, and likeness to the citrus flower fragrance of Jeju Island and taste preference of the fragrance were investigated through the olfactory sensory test. The sensory evaluation was carried out by a professional irrigation and general person. The similarity with the citrus flower fragrance of Jeju Island and the preference of the fragrance were evaluated through questionnaires.

The present invention provides a fragrance composition containing the fragrance component of citrus flower of Jeju Island and methyl anthranilate as an essential component and reproducing the fragrance of citrus flower of Jeju Island.

Based on the above results, in the present invention, the fragrance component composed of myrcene, phenylacetaldehyde oxime and indole, which is the main component of the citrus flower fragrance of Jeju Island, is contained at 60 to 70 wt% A perfume composition is provided. More specifically, the perfume composition according to the present invention preferably contains 22 to 42% by weight of myrcene, 11 to 31% by weight of phenylacetaldehyde oxime and 1 to 20% by weight of indole based on the total weight of the composition.

In addition, the perfume composition of the present invention can improve palatability by adding methyl anthranilate, which is a characteristic aroma component indicating that it is a citrus flower of Jeju Island, to the main component of the citrus flower fragrance of Jeju Island, May be contained in an amount of 5 to 25% by weight, more preferably 10 to 20% by weight.

Myrcene, phenylacetaldehyde oxime, indole and methyl anthranilate, which are used as main ingredients for reproducing the citrus flower scent of Jeju Island, And the palatability of the fragrance is lowered.

In addition, the perfume composition according to the present invention may further include secondary fragrance components representing the fragrance of citrus flowers of Jeju Island in addition to the main components. For example, 2 to 22% by weight of fennesol, 2-phenylethyl 1 to 10% by weight of alcohol, 0.5 to 13% by weight of linalool, and 0.01 to 11% by weight of geraniol.

Although these secondary components are preferably used within the above range, they do not significantly affect the fragrance of the citrus flowers of Jeju Island, so they may be contained in an amount outside the above range as long as they do not affect the reproduction of the citrus flower fragrance of Jeju Island .

The present invention also relates to a composition for external application for skin containing a perfume composition recreating the citrus floral fragrance of Jeju Island. The composition for external application for skin according to the present invention may contain the above-mentioned perfume composition in an amount of 0.01 to 20% by weight based on the total weight of the composition.

When the composition is contained in the composition for external application for skin in the above-mentioned range, it is possible for the user to perceive the fragrance similar to the citrus flower of Jeju Island, to exhibit high palatability, and to enhance the persistence of fragrance.

Examples of the external preparation for skin containing the perfume composition according to the present invention include ointments, lotions, soluble images, suspensions, emulsions, creams, gels, sprays, papermaking agents, , But are not limited to these, and may be incorporated into any base known in the art.

Hereinafter, the present invention will be described in more detail by way of examples, but the present invention is not limited thereto, and other applications, modifications and the like of the present invention will be apparent to those skilled in the art. Hereinafter, the present invention will be described more specifically with reference to examples and test examples. It is to be understood that the scope of the present invention is not limited to these embodiments and test examples, and that variations, substitutions, and insertions conventionally known in the art And this is also included in the scope of the present invention.

[Example 1] Flavor analysis of citrus flowers of Jeju Island using SPME

One fragrant citrus flower was picked and the fragrance component was collected by adsorbing the fragrance component on a polyacrylate fiber coated with 85 ㎛ polyacrylate for 2 hours. Collected for 3 hours at Seogwipo City in Jeju Island.

After capturing the fragrance components, the fiber was sealed, transferred to the inlet of GC-MS, desorbed for 2 minutes, and subjected to GC-MS analysis. GC-MS analysis conditions are as follows.

Analysis condition

· Analytical instrument: HP 5890 II GC

· Detector: HP 5972 MSD

Column: DB-1 (60 m X 0.25 mm x 0.25 m)

· Carrier gas: He

Injection Temperature: 250 ° C

Detector Temperature: 280 ° C

Oven Temperature: 70 to 220 DEG C (3 DEG C / min)

Ionization Voltage: 70 eV

· Removal time: 2 minutes

As a result, the fragrance components of the citrus flowers of Jeju Island analyzed by the SPME method are shown in Table 1 (unit: wt%).

Fragrance component content Mirsen 32.22 Phenylacetaldehyde oxime 21.19 Indole 11.85 Panesol (E, E) 8.34 2-phenylethyl alcohol 3.21 Rinaldo 1.55 Geraniol 0.34 Other 21.3 Total content 100.0

From the results of Table 1, it was confirmed that citrus flowers of Jeju Island contain myrcene, phenylacetaldehyde oxime and indole as major fragrance components, and these major components occupy 65.26% by weight of the entire fragrance.

[Example 2] Preparation of combined fragrance

Based on the results analyzed in Example 1 above, a combined fragrance (Sample B) having the composition shown in Table 2 below was prepared (unit: wt%).

Fragrance component content Mirsen 32.22 Phenylacetaldehyde oxime 21.19 Indole 11.85 Panesol (E, E) 8.34 2-phenylethyl alcohol 3.21 Rinaldo 1.55 Geraniol 0.34 DEP (solvent) 21.3 Total content 100.0

[Test Example 1] Sensory evaluation comparing flavor of combination spice and natural Jeju island citrus flower

The following sensory evaluation was carried out in order to examine the similarity of the flavor similarity between the combined flavor (sample B) prepared in Example 2 and the native Jeju island citrus flower.

The sensory evaluation was performed on 20 normal male and female 20 to 45 year olds. Sample A of the citrus flowerpot of Jeju Island and sample B of the combined fragrance reproduced by SPME method were taken respectively, and the questionnaire of Table 3 (Question 1) and sample palatability (Question 2) of Sample A and Sample B were investigated. The results are shown in Table 4 below.

survey
(1) Question 1: How similar are samples A and B?
1) It is not at all similar.
2) Not very similar.
3) Just so.
4) Somewhat similar.
5) Very similar.
(2) Question 2: How much do you like the smell of Sample B?
1) Not at all good.
2) Not very good.
3) Just so.
4) Somewhat good.
5) Very good.

Rating agent Question 1 (similarity) Question 2 (palatability) One 3 One 2 2 One 3 One 2 4 2 2 5 One 2 6 One 2 7 2 2 8 2 4 9 2 2 10 2 2 11 2 2 12 3 3 13 3 2 14 2 One 15 One 3 16 One 2 17 3 2 18 2 One 19 3 2 20 One 2 Average 1.95 2.00

In the results of Table 4, Sample B, which is a combination fragrance, was different from actual flower flavor of citrus flowerpot.

[Test Example 2] Analysis of fragrance by a professional evaluation team and comparison of fragrance with citrus flower

As shown in the results of Test Example 1 above, the combined fragrance composition composed of the components analyzed by the SPME method had no similarity with that of the native Jeju island citrus flower. Therefore, the professional team composed of the irrigation companies performed sensory evaluation on the fragrance components of each of the citrus flowers of Jeju Island. As a result, among the fragrance components of citrus flowers of Jeju Island, Mirceen which produces the sweet balsam flavor, Phenylacetaldehyde oxime which can feel Fresh Floral, and Jasmine-like flavor It was confirmed that the three components of the indole are the main ingredients of the citrus flower.

[Example 3] Production of new combination fragrance according to change in content of main ingredient

From the results of Test Example 2, it can be confirmed that the main components of the original fragrance of citrus flower of Jeju Island are myrcene, phenylacetaldehyde oxime and indole. Therefore, the present inventors made the new combination fragrances of the following # 1 to # 4 in order to produce a fragrance having good palatability while showing the fragrance of the citrus flower of Jeju Island containing these three components.

The combined fragrances # 1 to # 4 were each prepared in the composition shown in Table 5 (unit:% by weight) while varying the content of the three fragrances to 50 to 80% by weight while keeping the ratio of these three components constant.

Fragrance component #One #2 # 3 #4 Mirsen 24.68 29.62 32.09 34.56 Phenylacetaldehyde oxime 16.24 19.49 21.11 22.73 Indole 9.08 10.89 11.80 12.71 Panesol (E, E) 31.03 24.82 21.72 18.62 2-phenylethyl alcohol 11.94 9.56 8.36 7.16 Rinaldo 5.77 4.61 4.04 3.46 Geraniol 1.26 1.01 0.88 0.76 Total content 100.0 100.0 100.0 100.0 Total content of the three main components 55 60 65 70

[Test Example 3] Sensory evaluation of the combined flavorings prepared in Example 3

The sensory evaluation on the similarity and palatability of citrus flower fragrance to the four combined flavorings prepared in Example 3 were carried out in the same manner as in Test Example 1 above. On the other hand, after performing the comparative sensory evaluation on the two fragrances, a resting time of 5 minutes was given to prevent post-sensory paralysis. The sensory evaluation results of the fragrance similarity and palatability of the new combination fragrance and the citrus flower are shown in Table 6 below.

evaluation
agent Question 1 (similarity) Question 2 (palatability) #One #2 # 3 #4 #One #2 # 3 #4 One 2.0 3.0 4.0 2.0 2.0 3.0 3.0 1.0 2 2.0 3.0 3.0 3.0 2.0 3.0 3.0 2.0 3 3.0 4.0 3.0 3.0 1.0 3.0 4.0 2.0 4 2.0 3.0 3.0 2.0 2.0 2.0 3.0 3.0 5 2.0 2.0 4.0 2.0 1.0 3.0 3.0 4.0 6 2.0 3.0 4.0 2.0 2.0 2.0 4.0 3.0 7 3.0 2.0 4.0 2.0 2.0 1.0 2.0 3.0 8 2.0 3.0 3.0 2.0 1.0 2.0 3.0 3.0 9 3.0 3.0 4.0 2.0 2.0 3.0 3.0 3.0 10 2.0 2.0 4.0 3.0 1.0 3.0 4.0 2.0 11 2.0 4.0 3.0 2.0 2.0 2.0 3.0 3.0 12 3.0 3.0 4.0 3.0 3.0 3.0 3.0 2.0 13 2.0 2.0 2.0 3.0 2.0 2.0 3.0 2.0 14 3.0 3.0 2.0 3.0 3.0 3.0 2.0 2.0 15 3.0 3.0 4.0 2.0 3.0 3.0 3.0 2.0 16 2.0 3.0 3.0 2.0 2.0 3.0 3.0 2.0 17 2.0 3.0 3.0 2.0 3.0 3.0 3.0 3.0 18 1.0 3.0 4.0 3.0 3.0 3.0 4.0 2.0 19 2.0 3.0 4.0 3.0 2.0 3.0 4.0 3.0 20 2.0 3.0 3.0 2.0 3.0 2.0 3.0 2.0 Average 2.25 2.90 3.4 2.40 2.10 2.60 3.15 2.45

In the results of Table 6 above, it was confirmed that Sample # 3 having the total content of the three major components of 65% by weight had the best similarity and palatability among the four combined flavors.

[Example 4] Preparation of flavor improving fragrance by analysis of a professional evaluation team

In order to improve the similarity and palatability of the fragrance of sample # 3 in which the fragrance of the citrus flower of Jeju Island was most similar in Table 6, 65% by weight of myrcene, phenylacetaldehyde oxime and indole And further added methyl anthranilate, which gives a unique flavor to the reproduction of the citrus flower fragrance, to produce a new combination perfume. At this time, methyl anthranilate was added at 1.00, 5.00, 10.00, 15.00, 20.00, 25.00 and 30.00 wt%, respectively. The standard of methyl anthranilate content was determined by the judgment of the professional group of the irrigation specialist. The compositions of these recombinant flavors are shown in Table 7 below (unit: wt%).

Fragrance component #end #I #All #la #hemp #bar #four Mirsen 32.09 32.09 32.09 32.09 32.09 32.09 32.09 Phenylacetaldehyde oxime 21.11 21.11 21.11 21.11 21.11 21.11 21.11 Indole 11.80 11.80 11.80 11.80 11.80 11.80 11.80 Methyl anthranilate 1.00 5.00 10.00 15.00 20.00 25.00 30.00 Panesol (E, E) 21.10 18.62 15.51 12.41 9.31 6.21 3.10 2-phenylethyl alcohol 8.12 7.16 5.97 4.78 3.58 2.39 1.19 Rinaldo 3.92 3.46 2.89 2.31 1.73 1.15 0.58 Geraniol 0.86 0.76 0.63 0.50 0.38 0.25 0.13 Total content 100.0 100.0 100.0 100.0 100.0 100.0 100.0

[Test Example 4] Sensory evaluation of the combined flavorings prepared in the examples

Sensory evaluation of the fragrance similarity and palatability of the combined fragrance # to # produced in Example 4 was carried out in the same manner as in Test Example 1 above. After performing a comparative sensory evaluation on the two fragrances, a resting time of 5 minutes was given to prevent posterior sensory paralysis. The results are shown in Table 8 below. The results are shown in Table 8 below. ≪ tb > < tb > < TABLE >

evaluation
agent Question 1 (similarity) Question 2 (palatability) #end #I #All #la #hemp #bar #four #end #I #All #la #hemp #bar #four One 4.0 3.0 4.0 4.0 4.0 3.0 4.0 3.0 3.0 3.0 3.0 3.0 4.0 3.0 2 3.0 3.0 3.0 4.0 4.0 3.0 3.0 2.0 3.0 3.0 4.0 4.0 3.0 3.0 3 3.0 3.0 4.0 5.0 5.0 3.0 2.0 3.0 4.0 4.0 5.0 4.0 3.0 2.0 4 2.0 3.0 4.0 4.0 4.0 3.0 3.0 3.0 3.0 4.0 4.0 4.0 2.0 3.0 5 3.0 3.0 3.0 4.0 4.0 3.0 3.0 3.0 3.0 4.0 5.0 3.0 3.0 3.0 6 3.0 3.0 3.0 3.0 4.0 3.0 3.0 2.0 4.0 3.0 4.0 4.0 4.0 2.0 7 3.0 3.0 4.0 4.0 3.0 3.0 3.0 3.0 4.0 3.0 4.0 3.0 3.0 2.0 8 3.0 4.0 4.0 4.0 3.0 4.0 3.0 3.0 3.0 4.0 3.0 4.0 4.0 3.0 9 3.0 3.0 4.0 4.0 4.0 3.0 2.0 3.0 3.0 3.0 5.0 3.0 3.0 3.0 10 3.0 4.0 3.0 5.0 4.0 4.0 3.0 3.0 3.0 4.0 4.0 4.0 3.0 3.0 11 3.0 3.0 3.0 3.0 4.0 3.0 3.0 3.0 4.0 3.0 4.0 5.0 4.0 4.0 12 3.0 4.0 4.0 5.0 3.0 4.0 2.0 3.0 3.0 4.0 4.0 4.0 3.0 3.0 13 3.0 3.0 3.0 3.0 2.0 3.0 2.0 4.0 2.0 3.0 4.0 4.0 2.0 3.0 14 2.0 3.0 3.0 5.0 3.0 3.0 2.0 3.0 4.0 5.0 3.0 3.0 2.0 2.0 15 3.0 4.0 4.0 4.0 4.0 4.0 3.0 3.0 3.0 4.0 4.0 4.0 3.0 3.0 16 2.0 3.0 4.0 4.0 4.0 3.0 3.0 3.0 3.0 3.0 5.0 4.0 3.0 2.0 17 3.0 3.0 3.0 4.0 4.0 3.0 3.0 3.0 4.0 5.0 4.0 4.0 4.0 2.0 18 3.0 4.0 4.0 4.0 3.0 4.0 3.0 4.0 3.0 4.0 4.0 4.0 2.0 3.0 19 3.0 4.0 4.0 4.0 4.0 4.0 3.0 2.0 2.0 4.0 5.0 4.0 3.0 2.0 20 4.0 3.0 4.0 4.0 4.0 3.0 3.0 2.0 3.0 3.0 5.0 4.0 4.0 3.0 Average 2.95 3.30 3.60 4.10 3.70 3.30 2.80 2.90 3.20 3.70 4.15 3.80 3.10 2.70

From the results of Table 8, it can be seen that when the main flavor component of the Jeju Island citrus flower composed of myrcene, phenylacetaldehyde oxime and indole contains 5 to 25% by weight of methyl anthranilate, the fragrance of the citrus flower of Jeju Island can be reproduced And the palatability was high (average 3.0 or more). In particular, when methyl anthranilate was contained in an amount of 10 to 20% by weight, it was found that the fragrance similarity and flavor preference with citrus flowers were excellent (average 3.5 or more).

On the other hand, when methyl anthranilate is contained in an amount of less than 5 wt% or more than 25 wt%, the similarity and palatability of the fragrance are lowered.

[Production Example 1]

Perfumes comprising fragrance compositions having similarity to the fragrance of citrus flowers of Jeju Island were prepared with the compositions shown in Table 9 below (unit: wt%).

ingredient content Jeju Island citrus flower fragrance reproduction reproduction combination fragrance
(Combination fragrances # to # bar of Example 4) 15 Alcohol 83 water 2 Pigment Suitable amount Sunscreen Suitable amount

Claims (5)

A fragrance composition containing fragrance components composed of myrcene, phenylacetaldehyde oxime and indole and methyl anthranilate to reproduce the fragrance of citrus flowers in Jeju Island,
The content of the fragrance component composed of the myrcene, phenylacetaldehyde oxime and indole is 60 to 70% by weight based on the total weight of the composition,
Wherein the content of methyl anthranilate is 5 to 25% by weight based on the total weight of the composition. The method of claim 1, wherein the content of the myrcene is 29.6 to 34.6 wt%, the content of the phenylacetaldehyde oxime is 19.5 to 22.7 wt%, and the content of the indole is 10.9 to 12.7 wt% The fragrance composition recreating the fragrance of citrus flowers of Jeju Island. The perfume composition according to claim 1, wherein the content of methyl anthranilate is 10 to 20% by weight based on the total weight of the composition. The composition according to claim 1, wherein the composition comprises 3 to 21% by weight of fennesol, 1 to 8% by weight of 2-phenylethyl alcohol, 0.5 to 4% by weight of linalool and 0.01 to 1% Wherein the fragrance composition reproduces the fragrance of the citrus flower of Jeju Island. A cosmetic composition comprising the perfume composition according to any one of claims 1 to 4.