KR20130046996A - Perfume composition for expressing the fragrance of gardenia jasminoides - Google Patents

Abstract

PURPOSE: A perfume composition which reproduces the fragrance of Gardenia jasminoides is provided to contain a perfume ingredient of Gardenia jasminoides and jasmine lactone as active ingredients. CONSTITUTION: A perfume composition which reproduces the fragrance of Gardenia jasminoides contains a perfume ingredient of Gardenia jasminoides and jasmine lactone as active ingredients. The perfume ingredient is trans-ocimene, linalool, trans-alpha-farnesene, methyl benzoate, and cis-3-hexenyl tiglate. An external use skin composition contains the perfume composition.

Description

Perfume composition for expressing the fragrance of Gardenia jasminoides}

The present invention relates to a perfume composition having excellent palatability while reproducing the intrinsic odor of gardenia flowers ( Gardenia jasminoides ).

The gardenia flower is an evergreen shrub belonging to the locust tree of the dicotyledon group P. locust and is native to China. It is 1 ~ 2m high and has a short hair on the twig. Leaves are opposite, long oval, shiny, with flat edges, short petioles and pointed chin leaves. The flower is a single flower, blooms in June ~ July, and is white, but after time passes, it becomes yellowish white and hangs at the end of branches. Corolla is 6 ~ 7cm in diameter, thick in quality, 6 ~ 7 sepals and petals are fragrant. Surgery is the same number. At the bud, the petals are twisted and covered. Fruits are egg-shaped upside down or oval, ripening in yellow red in September. There are 6 ridges about 2cm long, and calyx remains on top and does not split when mature. Inside are yellow pulp and seeds. Fruits are said to let go, and oriental medicine is used to treat insomnia and jaundice and has the effect of anti-inflammatory, hemostasis and diuresis. It is used as a colorant for food, and in the old days, it was stored in gardenia water and steamed to prevent the deterioration of military taste.

There may be various ways to reproduce the scent of the gardenia flower. For example, there are conventional methods of extracting the fragrance component of the flower into a form of Absolute using a solvent, and a steam distillation method of making the fragrance component into an essential oil. However, since the methods require high heat during the extraction process and the process is complicated and takes a lot of time, there may be a lot of difference from the original flavor of the flower.

To compensate for this drawback, solid phase micro extraction (SPME) has been developed. The SPME method is disclosed in a paper (SUPELCO international, Vol. 13, No. 4, p. 9-10), which is hereby incorporated by reference in its entirety. Unlike conventional extraction methods, the SPME method does not use a solvent and does not require pretreatment, so that the perfume component can be analyzed quickly and simply.

Korean Patent Application No. 2007-0023242

Thus, the present inventors attempted to reproduce the odor of gardenia flowers by using the SPME method, which is effective in analyzing the odor substances of actually blooming flowers. As a result, the trans-o-cymene (trans -Ocimene), Li nalrul (Linalool), trans-trans alpha Parr nesen (trans, trans -α-Farnesene), methyl benzoate (Methyl benzoate), cis-3-hexenyl tigeul rate ( cis- 3-Hexenyl tiglate) was found to be the main component of the gardenia flower scent. However, as a result of performing the sensory test, the present inventors found that only these components could not reproduce the smell of the native gardenia flower alone.

Thus, the present inventors conducted a study to reproduce the odor of the gardenia flower, trans -Ocimene, linalul, trans trans alpha farnesene ( trans , trans- α-Farnesene), methyl Jasmine Lactone (Jasmine lactone), which is a characteristic scent component of the gardenia flower such as methyl benzoate and cis- 3-hexenyl tiglate and the fragrance of Korean gardenia flower With the composition containing lactone as an essential ingredient, it was possible to reproduce the inherent odor of the gardenia flower, and found excellent palatability and came to complete the present invention.

Accordingly, it is an object of the present invention to provide a fragrance composition having excellent palatability while reproducing the inherent odor of gardenia flowers.

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

In order to achieve the above object, the present invention is not contained in the odor component of the gardenia flower and the natural gardenia flower, but the scent is a synthetic material having a floral, fruity scent as a substance close to the natural gardenia flower as a whole Provided is a fragrance composition that reproduces the odor of gardenia flowers containing jasmine lactone as an active ingredient.

The present invention also provides a topical skin composition containing a fragrance composition that reproduces the smell of the gardenia flower.

Fragrance composition according to the invention as the major component of the transformer to reproduce the gardenia flower flavor analysis by the SPME method o-cymene (trans -Ocimene), Li nalrul (Linalool), trans-trans alpha Parr nesen (trans, trans - α-Farnesene, methyl benzoate and cis- 3-hexenyl tiglate contain jasmine lactone, a synthetic substance that does not exist in natural gardenia flowers. The odor of gardenia flowers can be reproduced, and the palatability of the odor can be improved.

In the present invention, the analysis method for the odor component of the gardenia flower uses the SPME method. The SPME method analyzes the fragrance components of the volatile gardenia flower because the fragrance components adsorbed on the fiber can be quickly desorbed and injected into the GS-MS column without special pretreatment. It is advantageous. In the present invention, based on the fragrance component of the gardenia flower odor of South Sea of Gyeongsangnam-do analyzed by the SPME method, a combination fragrance was formed, and the similarity with the gardenia flower odor and palatability of the odor was performed through olfactory sensory test. Sensory tests were conducted by professional steering staff and the general public. Similarity with the gardenia flower scent and palatability were evaluated by questionnaire.

Fragrance components of the fragrance components of gardenia flower through the SPME method which results gardenia flower assay trans o-cymene (trans -Ocimene), Li nalrul (Linalool), trans-trans alpha Parr nesen (trans, trans -α-Farnesene ), Methyl benzoate, cis- 3-hexenyl tiglate and cis- 3-hexenol, cis 3-hexenol, cis 3-hexenyl benzoate It can be seen that (cis-3-Hexenyl benzoate), trans isoeugenol ( trans -Isoeugenol), cis -Ocimene ( cis -Ocimene).

This analysis on the basis of the results, gardenia trans o-cymene of the fragrance components of gardenia flower to reproduce the fragrance of flower trees (trans -Ocimene), Li nalrul (Linalool), trans-trans alpha Parr nesen (trans, trans -α -Farnesene, methyl benzoate, cis- 3-hexenyl tiglate, by adding Jasmine lactone, an ingredient for the Korean gardenia flower fragrance, It is possible to provide a composition that reproduces the natural odor of gardenia flowers having excellent palatability.

Perfume composition according to the present invention ( trans -Ocimene), linalul (Linalool), trans trans alpha farnesene ( trans , trans -α-Farnesene), methyl benzoate (Methyl benzoate), cis 3-hexenyl Tiglate ( cis- 3-Hexenyl tiglate) and Jasmine lactone are included as an active ingredient.

In addition, the perfume composition is cis 3-hexenol ( cis- 3-Hexenol), cis 3-hexenyl benzoate ( trans -Isoeugenol) and cis acimen ( cis -Ocimene).

Perfume composition according to the present invention, 39.6 to 48.2% by weight of trans -Ocimene, 23.3 to 28.3% by weight of linalool, trans trans alpha farnesene ( trans , trans- α-Farnesene) 13.2 ~ 16.0% by weight, methyl benzoate (5.2 ~ 6.3% by weight) and cis- 3-hexenyl tiglate ( cis- 3-Hexenyl tiglate) in the range of 5.1 to 6.2% by weight do. And jasmine lactone in the range of 3.8 to 4.7% by weight. Gardenia trans O as a main component to reproduce the flavor of wood flower cymene (trans -Ocimene), Li nalrul (Linalool), trans-trans alpha Parr nesen (trans, trans -α-Farnesene) , methyl benzoate (Methyl benzoate), cis-3-hexenyl tigeul rate (cis -3-hexenyl tiglate), jasmine lactone (Jasmine lactone) are preferable because even when it is used as a lower range is out of the range, gardenia lowering the fragrance similarity and tree flower, preference of fragrance Not. However, other ingredients are preferably used within the above range, but since they do not significantly affect the fragrance of the gardenia flower, they may be used in amounts outside the above range unless they affect the reproduction of the fragrance of the gardenia flower. It may be contained.

The composition according to the present invention mixed in the above range may be blended into the skin external base such as perfume and cosmetics, and the blending amount may be appropriately selected and blended in order to achieve the desired effect according to techniques conventional in the art. have.

Such external materials include, but are not limited to, ointments, lotions, soluble burns, suspensions, emulsions, creams, gels, sprays, papes, warning agents, patches or water pastes, and the like. It can be formulated in any base that has been formulated.

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  One] SPME Perfume Analysis of Gardenia Flower Using

A strong scented gardenia flower was selected and the scent components were collected by adsorbing the scent components on a fiber (Polyacrylate Fiber) coated with 85 μm polyacrylate for 2 hours. The collection site was collected for three hours at Nam-myeon, Namhae-gun, Gyeongsangnam-do, Korea.

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

. Mobile Phase Gas: He

. Inlet temperature: 250 ° C

. Detector temperature: 280 ℃

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

. Ionization Voltage: 70eV

. Desorption time: 2 minutes

As a result, the perfume components of the gardenia flower analyzed by the SPME method are shown in Table 1.

Flavor Name Content (% by weight) Trans- Ocimene 43.86 Linalool 25.82 Trans Trans Alpha Farnesene
( trans , trans -α-Farnesene) 14.61 Methyl benzoate 5.77 Cis 3-hexenyl tiglate ( cis- 3-Hexenyl tiglate) 5.65 Cis 3-hexenol ( cis- 3-Hexenol) 0.66 Cis-3-hexenyl benzoate 0.30 Trans iso eugenol (trans -Isoeugenol) 0.13 Cis o-cymene (cis -Ocimene) 0.11 Etc 3.09 Total content 100.00

As shown in Table 1, gardenia flower is trans-o-cymene (trans -Ocimene), Li nalrul (Linalool), trans-trans alpha Parr nesen (trans, trans -α-Farnesene) , methyl benzoate (Methyl benzoate), cis It was found that 3-hexenyl tiglate ( cis- 3-Hexenyl tiglate) as the main odor component and these main components occupy 95.71% by weight of the total. In this Reference Example 1, a sample of the perfume component collected directly from the gardenia flower was named sample A.

[ Test Example  1] The fragrance and the odor of the gardenia flower Comparative sensory evaluation

Based on the results of the analysis, a newly prepared combination flavor (Sample B) having the composition of Table 2 was prepared, and the fragrance similarity between the drug and the gardenia flower named Sample A was verified through sensory evaluation.

Flavor Name Content (% by weight) Trans- Ocimene 43.86 Linalool 25.82 Trans Trans Alpha Farnesene
( trans , trans -α-Farnesene) 14.61 Methyl benzoate 5.77 Cis 3-hexenyl tiglate ( cis- 3-Hexenyl tiglate) 5.65 Cis 3-hexenol ( cis- 3-Hexenol) 0.66 Cis-3-hexenyl benzoate 0.30 Trans iso eugenol (trans -Isoeugenol) 0.13 Cis o-cymene (cis -Ocimene) 0.11 Dipropyleneglycol 3.09 Total content 100.00

The sensory evaluation was performed on 20 general men and women aged 20 to 40 years, and each sample A of Gardenia flower and each sample of artificial fragrance analyzed by SPME method were reproduced. In addition, the taste similarity (question 1) and taste preference (question 2) of Sample A and Sample B were examined by responding to the questionnaire of Table 3 below. The results are shown in Table 4 below.

survey
(1) Question 1: How similar is sample A to sample 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 3 3 3 2 3 4 3 2 5 2 2 6 One 3 7 2 3 8 One 2 9 2 2 10 2 2 11 2 2 12 2 3 13 3 2 14 2 2 15 One 2 16 One 2 17 3 2 18 2 3 19 2 One 20 2 2 Average 2.05 2.2

As shown in Table 4, Sample B of the combination fragrance was found to have a lot of difference with the floral odor of gardenia, and also showed a low palatability.

[ Test Example  2] Perfume Analysis  Gardenia Flowers Scent Comparison

As shown in Test Example 1, the fragrance composition artificially formulated with the components analyzed by the SPME method had no similarity to the odor collected directly from the gardenia flowers.

Therefore, the expert evaluation group composed of the steering company performed sensory evaluation on each of the flavor components of the gardenia flower. As a result, among the fragrances of the gardenia flower, trans-Ocimene, which has a floral herbal scent, Linalool, which has a citrus floral scent, and green apple ( green apple) trans-trans alpha Parr nesen that the fragrance (trans, trans -α-Farnesene) , that a fruity flavor methylbenzoate (methyl benzoate), cis that a fresh green floral fragrance of flowers, herbs 3-hexenyl Five components of cis- 3-Hexenyl tiglate were found to be the main ingredients that create the unique odor of gardenia flowers.

 [ Example  1] Preparation of New Combination Flavors According to Changes in Content

The test example 2 is the main component from the original fragrance of gardenia flower trans o-cymene (trans -Ocimene), Li nalrul (Linalool), trans-trans alpha Parr nesen (trans, trans -α-Farnesene) , methyl benzoate (Methyl benzoate ), Cis 3-hexenyl tiglate ( cis- 3-Hexenyl tiglate) was confirmed. Therefore, the inventors of the present inventors have made new combination flavors of # 1 to # 4 to produce flavors with palatability while retaining the scent of the gardenia flower by containing these five components.

Combination fragrances # 1 to # 4 were prepared by varying the total content of the five fragrances to 65.8-95.8% by weight while maintaining a constant ratio of these five components (see Table 5).

Combination fee number
Spices people
(Content: wt%) #One
(65.8%) #2
(75.8%) # 3
(85.8%) #4
(95.8%) Trans- Ocimene 30.2 34.7 39.3 43.9 Linalool 17.7 20.4 23.1 25.8 Trans Trans Alpha Farnesene
( trans , trans -α-Farnesene) 10.0 11.6 13.1 14.6 Methyl benzoate 4.0 4.6 5.2 5.8 Cis 3-hexenyl tiglate
( cis- 3-Hexenyl tiglate) 3.9 4.5 5.1 5.7 Cis 3-hexenol ( cis- 3-Hexenol) 18.7 13.3 7.8 2.3 Cis 3-hexenyl benzoate
(cis-3-Hexenyl benzoate) 8.1 5.8 3.4 1.0 Trans iso eugenol (trans -Isoeugenol) 4.1 2.8 1.6 0.5 Cis o-cymene (cis -Ocimene) 3.3 2.3 1.4 0.4 Total content 100.0 100.0 100.0 100.0

[ Test Example  3] Example  Sensory Evaluation of Perfumes Prepared in 1

The four fragrances of Example 1, which were newly combined, were subjected to the similarity and palatability to the gardenia flower scent by sensory evaluation in the same manner as in Test Example 1. On the other hand, after performing the comparative sensory evaluation on the two combined flavorings, a resting time of 5 minutes was given to avoid post-sensory paralysis. Sensory evaluation results on the taste similarity and palatability of the new combination perfume and gardenia flower are shown in Table 6 below.

evaluation
agent Question 1 (similarity) Question 2 (palatability) Combination Spice Number Combination Spice Number #One #2 # 3 #4 #One #2 # 3 #4 One One 3 3 3 2 3 4 3 2 2 3 4 3 2 3 2 3 3 3 3 3 4 3 3 4 3 4 2 2 3 3 2 2 3 3 5 2 3 2 3 2 3 3 3 6 One 2 4 3 One 2 3 4 7 2 3 4 4 2 3 3 2 8 2 2 3 3 2 2 3 3 9 3 3 4 3 3 3 3 3 10 2 2 2 3 2 2 3 3 11 2 2 3 4 2 2 4 3 12 3 3 4 3 3 3 3 3 13 2 3 3 2 2 3 4 4 14 3 2 4 3 3 2 3 3 15 3 3 3 3 3 3 3 3 16 2 2 3 4 2 2 3 4 17 2 3 3 3 2 3 4 3 18 One One 3 3 One One 3 2 19 2 3 4 3 2 3 4 3 20 2 3 3 2 2 3 4 2 Average 2.1 2.6 3.3 3.1 2.2 2.6 3.3 3.0

As shown in Table 6, Sample # 3, in which the total content of the five main components accounted for 85.8% by weight, was shown to have the best similarity and palatability among the four combination perfumes, but both the similarity and palatability did not meet expectations. Appeared.

[ Example  2] Production of flavor-enhancing fragrance by analysis of professional evaluation team

In order to improve the similarity and palatability of the fragrance of Sample # 3 in which the odor of the gardenia flower was the most similar in Table 6, as in Sample # 3, trans- Ocimene, Linalool, and Trans It contains 85.8% by weight of total content of trans alpha transnesene ( trans , α-Farnesene), methyl benzoate, cis- 3-hexenyl tiglate, and synthesized therein. Jasmine lactone, a substance, was used to prepare a new combination fragrance. The content of the jasmine lactone, which is a synthetic material, is added in varying amounts of 1.0 wt%, 2.0 wt%, 3.0 wt%, 4.0 wt%, 4.0 wt%, 5.0 wt% and 6.0 wt%, and the other components are added. The total content of 100 was adjusted to match the content of this material. The composition of these recombinant flavors is shown in Table 7 below.

Combination fee number
Spices people
(Content: wt%) # # Me # All # La # Town # Bar Trans- Ocimene 39.3 39.3 39.3 39.3 39.3 39.3 Linalool 23.1 23.1 23.1 23.1 23.1 23.1 Trans Trans Alpha Farnesene
( trans , trans -α-Farnesene) 13.1 13.1 13.1 13.1 13.1 13.1 Methyl benzoate 5.2 5.2 5.2 5.2 5.2 5.2 Cis 3-hexenyl tiglate
( cis- 3-Hexenyl tiglate) 5.1 5.1 5.1 5.1 5.1 5.1 Cis 3-hexenol ( cis- 3-Hexenol) 7.3 6.7 6.2 5.7 5.1 4.5 Cis 3-hexenyl benzoate
(cis-3-Hexenyl benzoate) 3.1 2.9 2.6 2.4 2.2 2.0 Trans iso eugenol (trans -Isoeugenol) 1.5 1.4 1.3 1.1 1.0 0.9 Cis o-cymene (cis -Ocimene) 1.3 1.2 1.1 1.0 0.9 0.8 Jasmine lactone 1.0 2.0 3.0 4.0 5.0 6.0 Total content 100.0 100.0 100.0 100.0 100.0 100.0

[ Test Example  4] Example  Sensory Evaluation of Combination Perfumes Prepared in 2

With respect to the combination flavors of the six (#, #, #, # d, # d, # hemp, # bar) of Example 2, the taste similarity and palatability of the gardenia flower of the same method as in Test Example 1 It carried out by sensory evaluation. 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 gardenia flower are shown in Table 8 below.

Evaluation Agent Question 1 (similarity) Question 2 (palatability) Combination Spice Number Combination Spice Number #end #I #All #la #hemp #bar #end #I #All #la #hemp #bar One 4 3 4 5 4 3 2 4 4 3 4 4 2 4 4 4 4 4 4 3 3 4 3 4 3 3 4 3 4 4 4 4 3 4 3 4 4 3 4 3 3 3 3 4 4 3 3 4 3 3 3 5 3 4 3 4 3 3 3 4 3 3 4 3 6 3 3 3 4 4 3 4 4 4 5 3 2 7 3 3 4 5 3 4 3 3 3 5 4 3 8 3 4 4 4 3 4 3 4 3 4 3 3 9 3 2 3 5 4 3 3 3 3 4 4 4 10 3 4 4 4 4 3 3 3 3 3 3 3 11 3 3 4 4 4 3 4 4 3 4 4 3 12 3 4 4 4 3 3 4 4 4 4 3 3 13 4 4 4 4 4 3 4 3 3 4 3 4 14 3 3 3 4 3 4 3 4 3 3 3 4 15 3 3 3 5 4 3 3 3 4 4 4 4 16 3 4 3 5 3 3 4 4 3 5 4 4 17 3 3 4 5 4 4 2 3 4 5 3 4 18 2 3 3 3 3 3 3 4 4 4 4 4 19 3 3 3 3 3 4 3 4 3 5 3 3 20 2 4 3 4 3 3 3 3 4 4 3 4 Average 3.1 3.4 3.5 4.2 3.6 3.4 3.2 3.6 3.5 4.0 3.5 3.4

As can be seen from Table 8, the trans five-cymene (trans -Ocimene), Li nalrul (Linalool), trans-trans alpha Parr nesen (trans, trans -α-Farnesene) , methyl benzoate (Methyl benzoate), cis-3-hexyl When the main odor component of gardenia flowers such as cis- 3-Hexenyl tiglate contains 4% by weight of jasmine lactone, the odor of gardenia flowers can be best reproduced and excellent similarity is achieved. And palatability was confirmed.

[ Manufacturing example  One]

As described above, a perfume composition (#D) having a similarity to the odor of gardenia flowers was prepared to prepare a perfume of Table 9 below.

Perfume containing a fragrance composition reproducing the odor of gardenia flowers (content: wt%) Gardenia flower fragrance reproduction combination fragrance
Alcohol
water
Pigment
Sunscreen 15
To 80
Suitable amount
Suitable amount
Suitable amount

Claims (6)

A fragrance composition reproducing the fragrance of the gardenia flower, which contains the fragrance component of the gardenia flower and Jasmine lactone as an active ingredient. The method of claim 1, wherein the fragrance component of Gardenia tree flower is trans o-cymene (trans -Ocimene), Li nalrul (Linalool), trans-trans alpha Parr nesen (trans, trans -α-Farnesene) , methyl benzoate (Methyl benzoate ) And cis- 3-hexenyl tiglate ( cis- 3-Hexenyl tiglate). The method of claim 2 wherein the cis-3-hexyl composition senol (cis -3-Hexenol), cis-3-hexenyl benzoate (cis-3-Hexenyl benzoate) , trans-iso-eugenol (-Isoeugenol trans) and cis O Perfume composition characterized by further containing cimen ( cis- Ocimene). According to claim 2, wherein the fragrance composition is trans- Ocimene ( trans -Ocimene) 39.6 to 48.2% by weight, Linalool (23.3 ~ 28.3% by weight), trans trans alpha farnesene ( trans , 13.2--16.0 wt% of trans -α-Farnesene, 5.2-6.3 wt% of methyl benzoate, 5.1-6.2 wt% of cis- 3-hexenyl tiglate and jasmine Perfume composition characterized in that it contains lactone (Jasmine lactone) in an amount of 3.8 to 4.7% by weight. According to claim 3, wherein the fragrance composition is based on the total weight of the composition cis- 3-hexenol ( cis- 3-Hexenol) 5.2 ~ 6.2% by weight, cis 3-hexenyl benzoate (cis-3-Hexenyl benzoate) 2.2 ~ Perfume composition, characterized in that it is contained in an amount of 2.6% by weight, 1.0 to 1.2% by weight of trans- Isoeugenol and 0.9 to 1.1% by weight of cis- Ocimene. An external preparation composition for skin containing the perfume composition according to any one of claims 1 to 5.