KR101055137B1 - Perfume composition which reproduced scent of honeysuckle flower - Google Patents

Abstract

The present invention relates to a fragrance composition that reproduces the scent of honeysuckle flowers, and more particularly, trans-ocimene, cis 3-hexenyl tiglate (cis) analyzed as a scent component of honeysuckle flowers by the SPME method -3-hexenyl tiglate, cis-3-hexenyl acetate and cis-3-hexenol, etc., isoamyl acetate and anthra as artificial additives It is related with the fragrance composition which reproduced the fragrance of the phosphorus flower excellent in palatability by containing methyl anthranilate.

Honeysuckle * Flavor * Isoamyl acetate * Methyl anthranilate * Trans-Ocimen * Cis 3-hexenyl tiglate * Cis 3-hexenyl acetate * Cis 3-hexenol

Description

Perfume composition for expressing the fragrance of honeysuckle}

The present invention relates to a fragrance composition that reproduces the scent of honeysuckle flowers, and more particularly, trans-ocimene, cis 3-hexenyl tiglate (cis) analyzed as a scent component of honeysuckle flowers by the SPME method -3-hexenyl tiglate, cis-3-hexenyl acetate and cis-3-hexenol, etc., isoamyl acetate and anthra as artificial additives It is related with the fragrance composition which reproduced the fragrance of the phosphorus flower excellent in palatability by containing methyl anthranilate.

Indong is a plant named as Indong because its leaves do not fall even in winter. It is a semi-heterophyllum vine plant of Indopaceae, which is a dicotyledon plant, and grows in sunny places of mountains and fields. The stem is about 5m long, and the stem extends to the right to wind up while winding other objects. The branches are reddish brown and hollow. The leaves run opposite each other, long oval or wide bassos with flat edges, but the leaves on the young branches split like feathers. The flower blooms in May-June and is pale reddish white, but later turns yellow and is called a gold and silver flower. It runs on the axilla of two leaves and smells. Fruits are round as berry and ripen black from October to November. In oriental medicine, the flowers, leaves, and stems are used for the treatment of antipyretics, antidote, diuretics, blue blood, febrile diseases, swelling and various kinds of venom and swelling. It is distributed in Korea, Japan, and China.

There may be a variety of ways to reproduce the smell of flowers of the honeysuckle. For example, a solvent extraction method for making the fragrance component of the honeysuckle flower in the form of Absolute and a steam distillation method for making the fragrance component into an essential oil are conventional methods. However, these methods require high heat during the extraction process or the process is complicated and time consuming.

Therefore, the present inventors use the SPME method effective in analyzing the fragrance substances of living natural products, such as trans acimen, cis 3-hexenyl tiglate, cis 3-hexenyl acetate and cis 3-hexenol, etc. It was found out that, to prepare a combination perfume using this to try to reproduce the scent of honeysuckle flowers. However, as a result of performing the sensory test on the combination fragrance, it was found that only the components can not reproduce the smell of natural honeysuckle, the fragrance components of the honeysuckle, trans-ocimen, cis 3-hexenyl tiglate It is found that when it contains more artificial additives such as isoamyl acetate and methyl anthranilate as essential components, such as cis 3-hexenyl acetate and cis 3-hexenol, it has excellent palatability while reproducing the intrinsic odor of honeysuckle flowers. This invention was completed.

Accordingly, it is an object of the present invention to provide a perfume composition that reproduces the smell of honeysuckle flowers.

In addition, another object of the present invention is to provide an external composition for skin containing the perfume composition.

In order to achieve the above object, the present invention provides a fragrance composition that reproduces the scent of a honeysuckle flower containing the odor component of isoflower, isoamyl acetate and methyl anthranilate as an active ingredient to provide.

The present invention also provides an external composition for skin containing the perfume composition.

The fragrance composition according to the present invention isoamyl acetate in the main components of the scent of the honeysuckle, such as trans acimen, cis 3-hexenyl tiglate, cis 3-hexenyl acetate, and cis 3-hexenol analyzed by the SPME method. And by containing methyl anthranilate, the fragrance of a phosphorus flower can be reproduced, and palatability of a fragrance can also be improved.

The present invention is a odor component of Lonicera japonica (transocimen, cis 3-hexenyl tiglate, cis 3-hexenyl acetate, cis 3-hexenol, isoamyl acetate and methyl anthranilate as an active ingredient) It relates to a fragrance composition which reproduces the smell of the honeysuckle containing.

In addition, the fragrance composition according to the present invention is germane dienyl, methyl benzoate, cis osmane, indole, linalul, beta cubvin, cis 3-hexenyl butyrate, hexyl acetate, geraniol, cis 3-octenol , Cis 3-hexenyl 2-methylbutyrate, hexyl tiglate, cis jasmon and farnesol may be further contained.

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

First, the present inventors do not use a solvent and do not need pretreatment, so the SPME method (Solid Phase Micro Extraction; SUPELCO international, Vol. 13, No. 4, p. 9-10) can analyze the odor component quickly and simply. The fragrance component of honeysuckle was analyzed. The SPME method is advantageous for analyzing the fragrance component of highly volatile flowers because fragrance components adsorbed on the fiber can be quickly desorbed and injected into the GS-MS column without special pretreatment. In the present invention, a combination fragrance was prepared based on the fragrance component of the honeysuckle flower analyzed by the SPME method, and the olfactory sensory test was performed on the similarity with the honeycomb fragrance and palatability of the fragrance. The sensory evaluation was conducted by professional stewards and the general public, and the similarity with the scent of honeysuckle and palatability of the scent was evaluated by questionnaire.

As a result of analyzing the fragrance component of the honeysuckle flower through the SPME method, the fragrance component of the honeysuckle flower was trans occimen, cis 3-hexenyl tiglate, cis 3-hexenyl acetate, cis 3-hexenol, germane di It can be seen that it consists of, methyl benzoate, cisiomenene, indole, linalul and other components.

Based on the results of these analyses, the main components of the odor component of the honeysuckle, ie, trans acimen, cis 3-hexenyl tiglate, cis 3-hexenyl acetate, cis 3-hexenol In consideration of the palatability of the fragrance composition, by adding together isoamyl acetate and methyl anthranilate, which are artificial synthetic materials, it is possible to provide a fragrance composition having excellent palatability and reproducing the intrinsic odor of honeysuckle.

Perfume composition according to the present invention is 59.5 ~ 77.7% by weight of trans acimen, 3.9 ~ 5.1% by weight of cis 3-hexenyl tiglate, 0.8-1.1% by weight of cis 3-hexenyl acetate, cis 3-hexenol 0.8-1.0 wt%, germacrene D 1.5-5.2 wt%, methyl benzoate 1.5-5.0 wt%, cis-ocimene 1.5-5.0 wt%, indole ) 0.9-1.5 wt%, linalool 1.5-3.5 wt%, beta-cubebene 0.8-2.3 wt%, cis-3-hexenyl butyrate 0.7-2.0 Weight%, hexyl acetate 0.3-1.5 weight%, geraniol 0.3-1.5 weight%, cis 3-octenol 0.3-1.5 weight%, cis 3-hexenyl 0.3-1.5 wt% of cis-3-hexenyl 2-methylbutyrate, 0.3-1.5 wt% of hexyl tiglate, 0.7-1.5 wt% of cis-jasmone and farnesol (farnesol) 0.3 ~ 1.5% by weight and second as an artificial additive Isoamyl contains from 1 to 3% by weight and methyl anthranilate 4-8% by weight. At this time, the main components for reproducing the scent of the honeysuckle flower is trans-ocymen, cis 3-hexenyl tiglate, cis 3-hexenyl acetate, cis 3-hexenol and artificial additives isoamyl acetate and methyl anthranilate When used in an amount outside the above range, the smell similarity with honeysuckle flower is lowered, the taste of the smell is also lowered is not preferred. However, the other components are preferably used within the ranges set forth above, but since they do not significantly affect the scent of the honeysuckle, they may be contained in an amount outside the above range unless they affect the reproduction of the scent of the honeysuckle. Can be.

The present invention also relates to an external preparation composition for skin containing the perfume composition. The fragrance composition according to the present invention can be formulated into external skin bases such as perfumes and cosmetics, and the blending amount can be appropriately selected and blended to achieve the desired effect according to the conventional techniques in the art.

Such external bases include, for example, ointments, lotions, soluble burns, suspensions, emulsions, creams, gels, sprays, powders, warning agents, patches or water pastes, but are not limited thereto. It can be formulated in any external base which has been prepared.

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

Reference Example 1 Analysis of Fragrance of Honeysuckle Flowers Using SPME Method

In Indong village, the fresh and strong fragrance of the flower bloomed in the honeysuckle vine was picked and the fragrance component was collected by adsorbing the fragrance component on the fiber (Polyacrylate Fiber) coated with 85 μm of polyacrylate for 2 hours. The collection site was Indong village, Baekje, Buyeo-gun, Chungcheongnam-do, and the collection took place for 2 hours.

After collecting the odor component, the fiber (Fiber) was sealed and transferred to the inlet of GC-MS, and then desorbed for 2 minutes, GC-MS analysis was performed. GC-MS analysis conditions are as follows:

<Analysis Condition>

Analyzer: HP 5890 II GC

Detector: HP 5972 MSD

Column: DB-1 (60 m × 0.25 mm × 0.25 μm)

Mobile phase gas: He

Injection temperature: 250 ° C

Detector temperature: 280 ℃

-Oven temperature: 70 ~ 220 ℃ (3 ℃ / min)

Ionization Voltage: 70eV

Desorption time: 2 minutes

Table 1 shows the analysis results of the honeysuckle fragrance components analyzed by the SPME method.

Fragrance Content (% by weight) Trans acimen 66.88 Germacren Di 11.05 Cis 3-hexenyl tiglate 4.40 Methyl benzoate 1.65 Cis 3-hexenyl acetate 0.93 Cis ossimen 0.86 Cis 3-hexenol 0.85 Indole 0.57 Linalule 0.43 Beta Cubebin 0.33 Cis 3-hexenyl butyrate 0.28 Hexyl acetate 0.25 Geraniol 0.25 Cis 3-octenol 0.24 Cis 3-hexenyl 2-methylbutyrate 0.23 Hexyl tiglate 0.21 Cis jasmine 0.20 Panesol 0.20 Etc 10.19 Total content 100

As shown in the results of Table 1, as for the phosphorus flower, trans acimen, germacrene di, cis 3-hexenyl tiglate and methyl benzoate occupy 83.98% of the total fragrance components, so they are It was confirmed that the main component of the.

[Test Example 1] Comparative sensory evaluation between the fragrance and the fragrance of natural honeysuckle

Based on the results analyzed in Reference Example 1, after preparing a combination perfume (Sample A) having the composition of Table 2 newly prepared, verify the fragrance similarity between the combination perfume and natural honeysuckle (Sample B) through sensory evaluation It was.

Fragrance Content (% by weight) Trans acimen 66.88 Germacren Di 11.05 Cis 3-hexenyl tiglate 4.40 Methyl benzoate 1.65 Cis 3-hexenyl acetate 0.93 Cis ossimen 0.86 Cis-3-hexenol 0.85 Indole 0.57 Linalule 0.43 Beta Cubebin 0.33 Cis 3-hexenyl butyrate 0.28 Hexyl acetate 0.25 Geraniol 0.25 Cis 3-octenol 0.24 Cis 3-hexenyl 2-methylbutyrate 0.23 Hexyl tiglate 0.21 Cis jasmine 0.20 Panesol 0.20 Etc 10.19 Total content 100

The sensory evaluation was conducted on 15 general men and women aged 20 to 50 years, and the 10% DPG dilution sample A and the sample B of the artificial flower pollen reproduced by the SPME method were in charge of each. By responding to the questionnaire, the taste similarity (question 1) and taste preference (question 2) of Sample A and Sample B were examined. In the case of the combination perfume reproduced by the SPME method, it was diluted to a level similar to that of natural honeysuckle flower and presented on the sachet for accurate sensory evaluation. Sensory evaluation results are shown in Table 4 below.

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

Evaluation Agent Question 1 (similarity) Question 2 (symbolic) One 2 3 2 3 2 3 2 2 4 4 3 5 3 4 6 2 3 7 3 3 8 3 2 9 2 3 10 2 3 11 3 3 12 3 4 13 3 2 14 3 4 15 2 3 Average 2.7 2.9

As shown in the results of Table 4, both similarity and palatability did not exceed three points, so that the sample A of the combination fragrance was found to be significantly different from the floral scent of the flower pot, and palatability was not so good. there was.

Test Example 2 Analysis of Perfume by Professional Evaluation Team and Comparison of Perfume with Honeysuckle Flowers

As shown in the results of Test Example 1, the combination fragrance composed of the components analyzed by the SPME method was significantly different from the natural honey flower fragrance. Therefore, the expert evaluation group composed of the steering company performed the sensory evaluation for each flavor component of the honeysuckle flower. As a result, the fragrance of honeysuckle flowers is trans-Ocimen which produces citrus-green floral scent, cis 3-hexenyl tiglate, fruity-green scent which provides fresh green floral scent of flowers or herbs. It was confirmed that it is composed of cis 3-hexenyl acetate, which gives a fresh floral fragrance, such as lily of the valley, cis 3-hexenol, which gives the green fragrance of fresh vegetables. It was confirmed that the smell can be better reproduced.

Example 1 Preparation of a New Combination Fragrance According to the Content Change of Four Main Components

From Test Example 2 it was confirmed that the main component of the original fragrance of the honeysuckle flower is composed of trans acimen, cis 3-hexenyl tiglate, cis 3-hexenyl acetate and cis 3-hexenol. Therefore, the present inventors prepared these combinations of sample # to # hemp as described in Table 5 to contain the four components, in order to produce a flavor with good palatability while showing the scent of the honeysuckle.

Combination perfume # # to # # was prepared by changing the total content of the four flavors to 65 ~ 85% by weight, while maintaining a constant ratio of these four components (unit: weight%).

Test Example 3 Sensory Evaluation of the Fragrances Prepared in Example 1

For the five flavors (# ga ~ # hemp) of the newly combined Example 1, the sensory evaluation was carried out in the same manner as in Test Example 1 in order to determine the smell similarity and palatability with honeysuckle flowers. On the other hand, after performing the comparative sensory evaluation of the two combination flavors, a 5-minute rest period was given so that there was no post-sensory paralysis. Sensory evaluation results on the taste similarity and palatability of the new combination perfume and honeysuckle flower are shown in Table 6 below.

Evaluation Agent Question 1 (similarity) Question 2 (symbolity) Combination flavor number Combination flavor number #end #I #All #la #hemp #end #I #All #la #hemp One 3 3 4 3 2 2 3 4 4 3 2 2 4 3 3 2 2 3 3 4 2 3 3 4 4 3 2 3 4 3 3 2 4 2 3 3 4 3 3 3 3 2 2 5 3 2 3 2 2 2 3 4 3 3 6 2 3 3 2 2 3 3 4 3 3 7 3 3 4 3 3 2 3 3 2 2 8 3 2 3 2 2 3 2 3 2 3 9 2 3 2 2 2 2 2 3 3 2 10 3 4 3 3 2 3 4 3 3 2 11 2 3 3 2 3 2 2 3 3 2 12 3 3 4 3 2 3 3 2 2 2 13 2 4 3 3 3 2 2 3 3 3 14 3 2 3 2 3 3 3 4 3 3 15 4 3 3 3 2 2 2 3 4 3 Average 2.7 3.1 3.2 2.7 2.3 2.5 2.8 3.2 2.9 2.5

As shown in the results of Table 6, in terms of similarity with natural honeysuckle, the total # of the four main components of the honeysuckle fragrance ingredient occupies 70 or 75% by weight. Among the five combination fragrances, it showed excellent similarity, and in terms of palatability, the value of sample #da was 3.2 points, which showed the best palatability. However, both similarity and palatability were less than 3.5 points.

Example 2-1 Production of flavor-enhancing fragrance by analysis of professional evaluation group I

In order to improve the similarity and palatability in the sample # shown to be the most similar to the smell of honeysuckle in the results of Table 6, as shown in Table 7 below, the total content of the four fragrance components is maintained at 75% by weight, Isoamyl acetate with sweet banana flavor was mixed to prepare a combination flavor of new samples #A to #E. The strong isoamyl acetate content was in the range of 1 to 5%, and the other components were adjusted to adjust the total content 100 according to the change in the content of isoamyl acetate (unit: wt%).

[Test Example 4] Sensory evaluation of the combination perfume prepared in Example 2-1

For the five (#A ~ #E) of the combination perfume of Example 2-1, the sensory evaluation was carried out in the same manner as in Test Example 1 in order to determine the smell similarity and palatability with the honeysuckle. On the other hand, after performing the comparative sensory evaluation of the two combination flavors, a 5-minute rest period was given so that there was no post-sensory paralysis. Sensory evaluation results on the taste similarity and palatability of the new combination perfume and honeysuckle flower are shown in Table 8 below.

evaluation
agent Question 1 (similarity) Question 2 (symbolity) Combination flavor number Combination flavor number #A #B #C #D #E #A #B #C #D #E One 3 4 4 3 3 3 3 3 4 3 2 3 4 3 3 2 3 4 4 3 3 3 3 4 4 3 3 3 4 3 3 3 4 4 4 3 3 3 4 4 3 3 2 5 3 3 3 4 3 3 3 4 3 3 6 3 3 3 4 3 3 3 4 3 3 7 3 3 3 4 3 4 4 4 3 3 8 4 3 3 3 2 4 3 3 2 2 9 4 4 3 3 2 3 3 3 2 2 10 4 5 4 3 3 4 4 3 3 3 11 3 4 4 3 3 3 3 3 3 2 12 3 3 4 3 3 3 3 2 2 2 13 4 4 3 3 3 3 4 3 3 3 14 3 3 3 3 3 3 3 3 4 3 15 4 3 3 3 3 3 4 4 4 3 Average 3.4 3.6 3.3 3.2 2.8 3.3 3.5 3.3 3.0 2.7

As shown in the results of Table 8, isoamyl acetate 1-3 in the main odor component of the copper flower of trans acimen, cis 3-hexenyl tiglate, cis 3-hexenyl acetate, cis 3-hexenol At the weight%, the smell of the honeysuckle could be reproduced more similarly, and palatability was higher than that without the addition. However, when isoamyl acetate was more than 3% by weight, the similarity and palatability of the odor was worse than that when isoamyl acetate was not added.

Example 2-2 Preparation of Flavor-Reducing Fragrances by Analysis of Expert Evaluation Team II

In order to further improve the similarity and palatability in Sample #B showing the best similarity and palatability in the results of Table 8, the total content of the four fragrance components is 75% by weight and isoamyl acetate as shown in Table 9 below. Maintained at 2% by weight, and mixed with a grape-like fruit flavor and methyl anthranilate with orange blossom fragrance to prepare a new fragrance of the new samples # 1 to # 5. The other components were adjusted to adjust the total content 100 according to the change in the content of methyl anthranilate (unit: wt%).

[Test Example 5] Sensory evaluation of the combination perfume prepared in Example 2-2

For the five (# 1 ~ # 5) combination fragrances of Example 2-2, sensory evaluation was carried out in the same manner as in Test Example 1 to determine the smell similarity and palatability with honeysuckle. On the other hand, after conducting the comparative sensory evaluation of the two combination flavors, a 5-minute rest period was given so that there was no post-sensory paralysis. Sensory evaluation results on the taste similarity and palatability of the new combination perfume and honeysuckle flower are shown in Table 10 below.

Evaluation Agent Question 1 (similarity) Question 2 (symbolity) Combination flavor number Combination flavor number #One #2 # 3 #4 # 5 #One #2 # 3 #4 # 5 One 3 4 4 3 3 3 3 3 4 3 2 4 4 5 4 4 4 4 3 3 3 3 3 4 3 3 3 3 4 4 5 4 4 3 4 4 5 4 3 4 4 3 3 5 4 4 3 3 3 4 5 5 4 3 6 3 3 4 4 5 3 3 4 5 4 7 4 5 3 3 3 4 4 4 5 4 8 3 3 4 4 3 4 3 3 3 3 9 4 5 5 4 3 3 4 4 5 4 10 3 3 4 5 4 4 4 5 4 4 11 4 4 5 4 4 4 3 3 3 3 12 3 3 4 4 3 3 3 3 4 4 13 3 3 4 4 3 3 3 4 3 3 14 4 4 5 4 3 3 3 4 4 5 15 4 3 3 3 3 3 4 4 3 3 Average 3.5 3.7 4.0 3.8 3.4 3.4 3.6 3.8 3.9 3.5

As shown in the results of Table 10, the main odor component and isoamyl acetate of the phosphorus flower of trans acimen, cis 3-hexenyl tiglate, cis 3-hexenyl acetate, cis 3-hexenol At 3 wt% and 4 to 8 wt% methyl anthranilate, the fragrance of the honeysuckle was more similarly reproduced, and the palatability was higher than 3.5.

Formulation Example 1

To prepare a perfume of Formulation Example 1 in a conventional manner by combining the fragrance composition that reproduces the smell of the honeysuckle according to the composition shown in Table 11 (unit: weight%).

ingredient content Honeysuckle Reproduction Combination Fragrance (# 3 of Example 2-2)
Alcohol
water
Pigment
Sunscreen 10
88
Suitable amount
Suitable amount
Suitable amount

Claims (6)

A fragrance composition which reproduces the fragrance of a honeysuckle containing the fragrance component of an artificial flower, isoamyl acetate, and methyl anthranilate as an active ingredient. According to claim 1, wherein the fragrance component of the flower is trans-ocimene (cis-3-hexenyl tiglate), cis 3-hexenyl acetate (cis-3-hexenyl) acetate) and cis 3-hexenol (cis-3-hexenol) is a fragrance composition that reproduces the smell of honeysuckle flowers, characterized in that. According to claim 2, wherein the fragrance composition as a odor component Germacrene D (germacrene D), methyl benzoate (methyl benzoate), cis-ocimene (cis-ocimene), indole (indole), linalool (linalool), Beta-cubebene, cis-3-hexenyl butyrate, hexyl acetate, geraniol, cis 3-octenol ), Cis-3-hexenyl 2-methylbutyrate, hexyl tiglate, cis-jasmone and farnesol. Perfume composition which reproduced scent of honeysuckle flower characterized by. According to claim 2, wherein the perfume composition is trans-ocimene (trans-ocimene) 59.5 ~ 77.7 wt%, cis-3-hexenyl tiglate (3.9-5.1 wt%), 0.8-1.1 wt% cis-3-hexenyl acetate, 0.8-1.0 wt% cis-3-hexenol, 1-3 wt% isoamyl acetate Perfume composition reproducing the smell of honeysuckle, characterized in that it contains 4% to 8% by weight and methyl anthranilate (methyl anthranilate). According to claim 3, wherein the fragrance composition is 1.5 to 5.2% by weight of germacrene D, 1.5 to 5.0% by weight of methyl benzoate, cis-ocimene based on the total weight of the composition 1.5-5.0 wt%, indole 0.9-1.5 wt%, linalool 1.5-3.5 wt%, beta-cubebene 0.8-2.3 wt%, cis 3-hexenyl butyrate (cis -3-hexenyl butyrate 0.7-2.0% by weight, hexyl acetate 0.3-1.5% by weight, geraniol 0.3-1.5% by weight, cis-3-octenol 0.3- 1.5% by weight, cis-3-hexenyl 2-methylbutyrate 0.3-1.5% by weight, hexyl tiglate 0.3-1.5% by weight, cis-jasmone ) 0.7-1.5% by weight and farnesol (farnesol) fragrance composition that reproduces the smell of honeysuckle, characterized in that it contains. The external preparation composition for skin containing the fragrance composition as described in any one of Claims 1-5.