KR102065037B1 - Ginsenoside fatty acid ester compounds, preparation method thereof, and cosmetic composition comprising the same - Google Patents

Abstract

The present invention relates to a ginsenoside fatty acid ester compound, a method for preparing the same, and a cosmetic composition containing the same, and more particularly, to a ginsenoside fatty acid ester compound modified with a fatty acid ester compound to have hydrophobicity, and a method for preparing the same. The compound is excellent in penetration through keratin skin, effectively suppresses the expression of melanin and MMP-1, and is preferably applied as a cosmetic composition for skin whitening and wrinkle improvement.

Description

Ginsenoside fatty acid ester compound, a manufacturing method thereof, and a cosmetic composition comprising the same {GINSENOSIDE FATTY ACID ESTER COMPOUNDS, PREPARATION METHOD THEREOF, AND COSMETIC COMPOSITION COMPRISING THE SAME}

The present invention relates to a novel ginsenoside fatty acid ester compound having a skin whitening and antioxidant effect, a preparation method thereof, and a cosmetic composition containing the same.

Panax ginseng CA Meyer is a plant belonging to the genus Ogapiaceae ginseng and has been used in Korea, China and Japan for more than 2,000 years. It has been used to prevent disease and extend life. Ginseng's known effects and effects to the central nervous system, anti-carcinogenic and anti-cancer activity, immune function regulation, anti-diabetic effect, liver function anti-inflammatory effect, cardiovascular disorder improvement and anti-arteriosclerosis, blood pressure control action, menopausal Effects on improving disorders and osteoporosis, antistress and anti-fatigue, antioxidant activity and anti-aging effects are known.

Various effects and effects of the above ginseng is due to a component called 'ginsenoside' (Ginsenoside, a glycoside in ginseng, aka saponin) which is a kind of saponin. Ginsenosides have a structure in which sugar is attached to a steroid skeleton, which is changed by heat. Steaming breaks the steroid-glucose bond, resulting in a drop in sugar and a different effect depending on what sugar remains in the position. As the water-soluble sugars fall, they become fat-soluble and produce ginsenosides that are easy to pass through the cell membrane.

There are more than 30 kinds of ginsenosides, and they do not all have the same ingredients and efficacy. These ginsenosides are based on the number of hydroxy groups (OH) in the structure, based on protopanaxadiol (hereinafter referred to as 'PPD') and protopanaxatriol (hereinafter referred to as 'PPT'). Are distinguished. Among these, PPD ginsenosides include Ra1, Ra2, Ra3, Rb1, Rb2, Rb3, Rc, Rd, Rg3, Rh2 and the like, and PPT ginsenosides include Re, Rg1, Rg2, Rf, Rh1, and the like. have.

The PPD-based and PPT-based ginsenosides can be applied to various fields. For example, Korean Patent Publication No. 2015-0083290 discloses Rb1, Rd, F1, Fe, Rg1, F2, Compound K (CK), Rg3, Re, Rh1, Rh2, Rg5, Rk1 and PPD and derivatives thereof have no skin side effects and whitening and anti-wrinkle effect. Korean Patent Registration No. 10-146981 discloses that PP-based ginsenoside Rd promotes collagen biosynthesis. It is disclosed that it can be applied as a cosmetic composition by inhibiting the production of MMP-1.

In addition, Korean Patent Registration No. 10-1233833 contains PPT ginsenoside Re to remove excess keratin of skin and promote cell cycle activity to prevent percutaneous moisture loss and wrinkle formation to improve skin. Patent registration No. 10-1427572 discloses that a mixture of ginsenoside Re and compound K can be applied as an external preparation for skin by promoting the production of hyaluronic acid.

On the other hand, the skin is composed of lipids, the cell gap and the outermost stratum corneum in its structure, the skin surface is covered with sebum (oil component) secreted by the cells. Unfortunately, it is difficult for a hydrophilic material to penetrate through the skin, and to increase the concentration of the hydrophilic substance or give an electric shock such as ion foresis.

PPD-based or PPT-based ginsenoside compounds have two or more OH groups in their molecular structure and exhibit high hydrophilicity. Therefore, the skin penetration of the PPD-based or PPT-based ginsenoside compound is very low, and even if the cosmetic composition contains these components, the amount to be penetrated or absorbed into the skin is small and the effect obtained substantially is inadequate.

Republic of Korea Patent Publication No. 2015-0083290, "Manufacturing method of ginsenoside derivatives and the composition for whitening and wrinkle improvement comprising the ginsenoside derivatives prepared as an active ingredient" Republic of Korea Patent No. 10-146981, "Wrinkle improvement cosmetic composition containing ginsenoside Rd and F2 as an active ingredient" Republic of Korea Patent Registration No. 10-1233833, "Cosmetic composition for skin moisturizing and wrinkle improvement containing ginsenoside Re" Republic of Korea Patent No. 10-1427572, "External skin composition for promoting hyaluronic acid production containing ginsenoside Re and ginsenoside compound 사이드"

In order to solve the above problems, the present inventors reacted with fatty acid vinyl ester compounds to increase the hydrophobicity of PPD- or PPT-based ginsenoside compounds to prepare novel compounds, and the compounds thus obtained have excellent penetration into the stratum corneum, By inhibiting the production of melanin pigment has a skin whitening effect and significantly inhibited the collagen degrading enzyme MMP-1, it was confirmed that the excellent wrinkle improvement effect was completed the present invention.

Accordingly, it is an object of the present invention to provide novel ginsenoside fatty acid ester compounds.

Another object of the present invention is to provide a method for preparing a ginsenoside fatty acid ester compound.

Still another object of the present invention is to provide a use of the ginsenoside fatty acid ester compound as a cosmetic composition.

In order to achieve the above object, the present invention provides a ginsenoside fatty acid ester compound represented by the following formula (1):

[Formula 1]

(In Formula 1, R ₁ to R ₃ are as described in the specification)

In addition, the present invention is represented by the following Scheme 1,

Provided is a method for preparing a ginsenoside fatty acid ester compound of Formula 1 prepared by enzymatic conversion of a compound of Formula 6 and a saturated or unsaturated fatty acid vinyl ester of C12 to C22:

Scheme 1

(In Reaction Scheme 1, R ₁ to R ₃ are as described in the specification)

The present invention also provides a cosmetic composition comprising the ginsenoside fatty acid ester compound represented by Formula 1 as an active ingredient.

The ginsenoside fatty acid ester compound according to the present invention has a whitening effect and wrinkle improvement effect of the existing PPD-based or PPT-based ginsenoside compound, and hydrophobicity is improved to have skin penetration ability to the skin keratin.

Specifically, the compound acts on tyrosinase, an enzyme that produces melanin pigment, which causes freckles and blemishes, inhibits the production of melanin pigment, and has a skin whitening effect, and retinophosphate expression of MMP-1, an enzyme that degrades collagen. It can be more significantly suppressed to obtain a wrinkle improvement effect, it is formulated into a variety of cosmetic products to improve the consumer satisfaction.

1 is a graph showing the MMP-1 inhibitory effect of the compound of Example 1 and Comparative Example 1.

Hereinafter, the present invention will be described in detail.

The present invention proposes a novel compound modified to have hydrophobicity in order to enhance skin absorption of PPD- or PPT-based ginsenoside compounds. Preferably, the novel compound is a ginsenoside fatty acid ester compound represented by Formula 1:

[Formula 1]

(In Formula 1,

R ₁ is OH or a saturated or unsaturated fatty acid group of C12 to C22,

R ₂ is a C12-C22 saturated or unsaturated fatty acid group,

R ₃ is H or OH)

Saturated fatty acid groups of C12 to C22 referred to herein are lauryl group (C12: 0, lauryl), tridecyl group (C13: 0, tridecyl), myristyl group (C14: 0, myristil), pentadecyl group (C15 : 0, pentadecyl), palmityl (C16: 0, palmityl). Margaryl group (C17: 0, margaryl), stearin group (C18: 0, stearyl), nonadecyl group (C19: 0, nonadecyl), arykidyl group (C20: 0, arachidyl), heneicosyl group (C21: 0 , heneixosylyl), or behenyl group C22: 0, behenyl).

In addition, the unsaturated fatty acid group of C12 to C22 referred to in the present specification is palmitoleyl group (C16: 1, palmitoleyl), oleyl group (C18: 1, oleyl), myrioleyl group (C14: 1 myristoleyl), linoleyl group (C18: 2, linoleyl) or arachidyl group (C20: 3, arachidonyl).

Preferably R ₁ is OH, palmityl group. It is a stearin group or an oleyl group, More preferably, it is an OH or palmityl group.

Also, preferably, R ₂ is a palmityl group. It is a stearin group or an oleyl group, More preferably, it is a palmityl group.

In particular, the compounds of formula 1 of the present invention include all isomers unless otherwise specified. The isomers can be seen due to all stereoisomers, such as those which may exist due to asymmetric carbons on various R and Z substituents (including enantiomers (which may be present even when no asymmetric carbon is present) and diastereomers) Are considered within the scope of the invention. Each stereoisomer of a compound of the invention can be, for example, substantially free of other isomers, or mixed, for example, with racemates or with all stereoisomers or selected stereoisomers.

For example, it may be represented by an isomer of Formula 1a:

[Formula 1a]

(In Formula 1, R ₁ to R ₃ are as described above)

Examples of the compound represented by Formula 1 include the following compounds:

[Formula 2]

[Formula 3]

[Formula 4]

[Formula 5]

In addition, the present invention is represented by the following Scheme 1,

A method for preparing a ginsenoside fatty acid ester compound of Formula 1 by enzymatic conversion of a compound of Formula 6 to a saturated or unsaturated fatty acid vinyl ester of C12 to C22 is provided:

Scheme 1

(In Reaction Scheme 1, R ₁ to R ₃ are as mentioned above)

The compound of Chemical Formula 6, which is a starting material in Scheme 1, is a ginsenoside compound, and may be PPD (R ₃ = H) represented by Chemical Formula 7 or PPT (R ₃ = OH) represented by Chemical Formula 8 or a derivative thereof. have.

[Formula 7]

[Formula 8]

Such starting materials may be obtained from ginseng, red ginseng, white ginseng, ginseng, rice ginseng, ginseng leaves, or ginseng fruit, or directly manufactured or purchased commercially available.

For example, ginseng tablet saponin may be hydrolyzed with acid, alkali or enzyme to remove sugar from ginseng saponin, and then the reaction solution may be prepared by passing through a silica column. Enzymes that can be used here include beta-glucosidase, alpha, and beta-arabinosidase, alpha and beta-rhamnose, which break down saponin sugar bonds. and exo-glucose degrading enzymes such as and β-rhamnosidase, and complex enzymes containing them.

In addition, in Scheme 1, the fatty acid vinyl ester compound is a compound that introduces R ₁ and R ₂ into the chemical structure of Chemical Formula 1, and may be a C12 to C22 saturated or unsaturated fatty acid vinyl ester compound.

Preferably, the C12 to C22 saturated fatty acid vinyl ester compound is a vinyl lauryl ester (C12: 0, lauryl), tridecyl acid vinyl ester (C13: 0, tridecylic acid vinyl ester), myristyl vinyl ester ( C14: 0, myristic acid vinyl ester), pentadecyl acid vinyl ester (C15: 0, pentadecylic acid vinyl ester), palmitic acid vinyl ester (C16: 0, palmitic acid vinyl ester), margaric acid vinyl ester (C17: 0, margaric acid vinyl ester), stearic acid vinyl ester (C18: 0, nonadecylic acid vinyl ester), arycidyl acid vinyl ester (C20: 0, arachidyl), Heneixosylic acid vinyl ester (C21: 0), or behenylic acid vinyl ester (C22: 0).

In addition, the unsaturated fatty acid vinyl ester compounds of C12 to C22 include palmitoleic acid vinyl ester (C16: 1, palmitoleylic acid vinyl ester), oleic acid vinyl ester (C18: 1, oleylic acid vinyl ester), and myrioleoleic acid vinyl ester (C14: 1, myristoleylic acid vinyl ester), linoleylic acid vinyl ester (C18: 2), or arachidonylic acid vinyl ester (C20: 3).

More preferably, the fatty acid vinyl ester compound is palmitic acid vinyl ester. Stearic acid vinyl esters, or oleic acid vinyl esters, most preferably vinyl palmitate.

The reaction proceeds with an enzyme conversion reaction.

The enzyme is a protease (protease) or lipase can be characterized by using a hydrolase, such as (lipase), as the hydrolase is let Plastic Im (flavourzyme), protease A (protease A), Alcala the ( alcalase), Sabina claim (savinase), Pro other Mex (protamex), Esper cyclase (esperase), Novozymes (novozyme), esterase (esterlase), acylase (acylase) and, but to use a mixture thereof, It is not limited to this. In addition, a microorganism containing the hydrolase may be used as the enzyme source. Preferably, in the embodiment of the present invention was used novozyme 435 ( novozyme 435, Novozyme).

These strains Bacillus strains (Bacillus sp), Aspergillus duck claim (Aspergillus oryzae ), Aspergillus niger , Candida antarctica and mixtures thereof, and the like, but may be used without limitation as long as the strain or microorganism contains a hydrolase.

Kinds and administration methods of enzymes added in Scheme 1 are not particularly limited as long as they do not cause inactivation of enzymes, and methods commonly used in the art may be used.

The reaction temperature is reacted while stirring for 1 to 120 hours, preferably 36 to 72 hours in the range of 20 ~ 60 ℃ in the case of novozyme temperature, that is, enzyme inactivation does not occur.

The solvent used here is lower alcohols such as water, methanol, ethanol and propanol, and acetone, dimethylformamide (DMF), methylene chloride (MC), diisopropyl ether, diethyl ether and tetrahydrofuran (THF) as organic solvents. ), Dimethylacetamide (DMA), dimethyl sulfoxide (DMSO), chlorobenzene, toluene, benzene and the like can be used singly or in combination, preferably acetone.

The ginsenoside fatty acid ester compound of Formula 1 according to the present invention is applicable to various fields, and may be preferably used as an active ingredient of a cosmetic composition.

That is, the ginsenoside fatty acid ester compound of Formula 1 exhibits hydrophobicity while maintaining the whitening effect and wrinkle improvement effect of the ginsenoside compound, especially the ginsenoside PPD and PPT, and is excellent in penetrating power to the stratum corneum.

In addition, as the ginsenoside fatty acid ester compound of the present invention exhibits hydrophobicity, the reactivity with tyrosinase, an enzyme that produces melanin pigments causing freckles and blemishes, is improved. For this reason, as shown in the test example 1, the whitening effect excellent compared with the koji-acid or rucinol which was excellent in the conventional whitening effect was secured.

In addition, as a result of measuring the expression inhibitory effect of MMP-1, an enzyme that degrades collagen (see Test Example 2), the ginsenoside fatty acid ester compound of the present invention was significantly inhibited than retinoic acid, thereby ensuring wrinkle improvement. It can be seen that.

Thus, the ginsenoside fatty acid ester compound of Formula 1 may be used as an active ingredient of the cosmetic composition, the content of which varies depending on the formulation, it may be used in 0.001 to 99% by weight. When the active ingredient is contained in the above range, it is not only suitable to exhibit the intended effect of the present invention, but also satisfies both the stability and solubility of the composition, and may be appropriate to include in the above range in terms of cost-effectiveness.

Cosmetic compositions can be prepared in any formulations conventionally prepared in the art, including, for example, solution suspensions, emulsions, pastes, gels, creams, lotions, powders, oils, powder foundations, emulsion foundations, wax foundations And it may be formulated in a spray or the like, but is not limited thereto. More specifically, it may be prepared in the form of a sun cream, a flexible lotion, a convergent lotion, a nourishing lotion, a nourishing cream, a massage cream, an essence, an eye cream, a pack, a spray or a powder.

In addition, the cosmetic composition according to the present invention is a fatty substance, an organic solvent, a dissolving agent, a thickening agent, a gelling agent, a softening agent, an antioxidant, a suspending agent, a stabilizer, a foaming agent, a fragrance, a surfactant, water, an ionic type or Nonionic emulsifiers, fillers, metal ion sequestrants, chelating agents, preservatives, vitamins, blockers, wetting agents, essential oils, dyes, pigments, hydrophilic or lipophilic active agents, lipid vesicles or any other ingredients commonly used in cosmetics It may contain adjuvants conventionally used in the cosmetic or dermatology field. Such adjuvants are introduced in amounts generally used in the cosmetic or dermatological arts.

When the formulation is a paste, cream or gel, animal oil, vegetable oil, wax, paraffin, starch, tracant, cellulose derivative, polyethylene glycol, silicone, bentonite, silica, talc or zinc oxide may be used as a carrier component. .

If the formulation is a powder or a spray, lactose, talc, silica, aluminum hydroxide, calcium silicate or polyamide powder may be used, especially in the case of a spray, additionally chlorofluorohydrocarbon, propane / butane. Or propellants such as dimethyl ether.

When the formulation is a solution or emulsion, a solvent, solubilizer or emulsion is used as carrier component, such as water, ethanol, isopropanol, ethyl carbonate, ethyl acetate, benzyl alcohol, benzyl benzoate, propylene glycol, 1,3 Fatty acid esters of butylglycol oil, glycerol aliphatic ester, polyethylene glycol or sorbitan.

When the formulation is a suspension, a carrier diluent such as water, ethanol or propylene glycol, suspending agents such as ethoxylated isostearin alcohol, polyoxyethylene sorbitol ester and polyoxyethylene sorbitan ester, microcrystalline cellulose, Aluminum metahydroxide, bentonite, agar or tracant and the like can be used.

Hereinafter, the present invention will be described in more detail with reference to the following examples. However, the following examples are merely to illustrate the present invention, but the content of the present invention is not limited by the following examples.

 [ Example  1] Preparation of the Compound of Formula 2

In a pressure tube (PPD, 1eq), vinyl palmitate (2.5eq), 4 체 molecular sieve (100 wt%), novozyme 435, and anhydrous acetone (500 wt%, 5 to substrate) in a pressure vessel (Pressure Tube) Pear) was injected and stirred at 45 ° C. for 3 days to proceed with the reaction.

After completion of the reaction, the obtained product was purified by silica gel column chromatography (ethyl acetate: methanol = 10: 1) to prepare a compound of formula 2 (white solid, yield 78%).

¹ H NMR (300 MHz, CDCl ₃ ) d 7.26 (1H), 7.00 (1H), 5.26 (1H), 4.31 (1H), 3.94 (1H), 2.32-2.29 (3H), 2.18-2.16 (2H), 1.93 -1.55 (19H), 1.49-1.41 (3H), 1.37-1.24 (29H), 1.07-0.86 (21H)

[ Example  2] Preparation of Compound of Formula 3

A compound of Formula 3 was prepared in the same manner as in Example 1, except that the compound of Formula 8 (PPT, 1eq) was used as a starting material (yield 82%).

¹ H NMR (300 MHz, CDCl ₃ ) d 7.27 (1H), 6.99 (1H), 5.26 (1H), 5.24 (1H), 4.47 (1H), 4.31 (1H), 3.84 (1H), 2.40 (1H), 2.27-2.17 (4H), 2.03-1.55 (20H), 1.4-1.27 (29H), 1.15-0.77 (21H)

[ Example  3] Preparation of Compound of Formula 4

A compound of Formula 4 (yield 90%) was prepared in the same manner as in Example 1, except that the compound of Formula 7 (PPD, 2eq) was used as a starting material.

¹ H NMR (300MHz, CDCl ₃ ) d 7.27 (1H), 5.12 (1H), 4.31 (1H), 3.91 (1H), 2.62 ((1H), 2.30 (4H), 2.09-1.96 (4H), 1.87- 1.49 (20H), 1.41-1.24 (53H), 1.14-0.86 (26H)

[ Example  4] Preparation of Compound of Formula 5

A compound of Chemical Formula 5 (yield 87%) was prepared in the same manner as in Example 1, except that the compound of Chemical Formula 8 (PPT, 2eq) was used as a starting material.

¹ H NMR (300MHz, CDCl ₃ ) d 7.27 (1H), 5.26 (1H), 5.12 (1H), 4.47 (1H), 4.31 (1H), 3.98 (1H), 2.71 ((1H), 2.30 (4H) , 2.12 (1H), 2.03-1.90 (4H), 1.82-1.55 (19H), 1.41-1.24 (52H), 1.16-0.86 (25H)

[ Test Example  1] Inhibitory effect of melanogenesis in melanocyte-producing cells

The melanin production inhibitory effect in melanocyte-producing cells to the compound prepared in Example 2 was measured by Dooley's method.

The cell line used mouse-derived B16 F10 (melanoma cells) purchased from Korea Cell Line Bank. DMEM (Cat No. 11995), FBS (Cat No. 16000-044) and antibiotic-antifungal reagents (Cat No. 15240-062) required for cell culture were purchased from Invitrogen (GIBCO).

Cell lines were incubated under 37 ° C., 5% CO ₂ . Cultured B16F10 cells were detached with 0.05% Trypsin-EDTA and seeded in 48-well plates again in the same number (1 × 10 ⁴ cells / well), followed by three consecutive days from the second day. Compounds were replaced with medium containing 10 ppm concentration. In this case, kojic acid and rucinol were used as comparative examples.

After 5 days, 1N NaOH was treated and reacted at 60 ° C. for 2 hours to melt melanin contained in the cells, and the amount of melanin was measured by measuring absorbance at 405 nm. From this the concentration of Example (IC ₅₀ ) required to reduce melanin production in melanocytes by half is calculated and shown in the table below.

Test substance IC ₅₀ Kojisan > 500 μM Rucinol 16 μM Compound of Example 1 7.4 μM Compound of Example 2 7.3 μM Compound of Example 3 7.6 μM Compound of Example 4 7.8 μM

Referring to Table 1, the compound according to the present invention can inhibit melanin production in a small amount compared to koji acid and rucinol and the like. Therefore, it can be seen that the ginsenoside fatty acid ester compounds according to the present invention have excellent skin whitening effect by inhibiting melanin production.

[ Test Example  2] MMP -1 expression inhibitory effect

To evaluate the inhibitory efficacy of MMP-1 expression of ginsenoside fatty acid ester compounds, fibroblasts were dispensed in ^four well plates at 1 × 10 ⁴ per well, containing 10% FBS until reaching about 80% confluency. Incubated for about 24 hours in the medium. Thereafter, the cells were exchanged with a medium without FBS for 24 hours.

After washing the cells once with PBS for UV irradiation, UVB 15 mJ / ㎠ was irradiated with 100 ml of PBS. After PBS was removed, the resultant was treated by diluting the final concentration of the ginsenoside fatty acid ester compound prepared in Example 1 to 0.01, 0.05, 0.1 and 0.5% in a fresh medium without FBS. Retinoic acid was used. After 48 hours of treatment with the test material, the culture supernatants were collected and evaluated for expression of MMP-1 using ELISA kits (enzyme-linked immunosorbent assay kits; RPN 2610, Biotrak Amersham Pharmacia Biotech, UK). The amount of MMP-1 respectively measured was corrected by the total protein amount, and the results are shown in Table 2 and FIG. 1. 1 is a graph comparing the MMP-1 inhibition rate of the compound of Example 1 and Comparative Example 1.

% Inhibition of MMP-1 expression density(%) Example 1 Example 2 Example 3 Example 4  Comparative Example 1 0 100 100 100 100 100 0.01 98.1 98.1 97.9 97.6 98.1 0.05 76.7 76.3 78.2 77.5 87.3 0.1 65.3 67.1 61.7 68.0 82.5 0.5 41.1 43.0 41.3 44.1 72.2

Referring to Table 2 and Figure 1, ginsenoside fatty acid ester compound according to the present invention is a retinoic acid than Comparative Example 1 It can be seen that it significantly inhibits the expression of MMP-1.

Through these results, the ginsenoside fatty acid ester compound presented in the present invention inhibits the biosynthesis of skin tissue degrading enzyme MMP-1 caused by internal aging or external environmental factors, thereby inhibiting skin aging and improving wrinkles. It can be seen.

Hereinafter, another formulation example of the present invention will be described, but the cosmetic formulation containing the ginsenoside fatty acid ester compound according to the present invention is not limited only to these examples.

[Formulation Example 1] Lotion

The lotion was prepared according to a conventional method with the composition described in the table below.

ingredient Content (% by weight) Compound of Example 1 0.1 glycerin 3.0 Butylene glycol 2.0 Propylene glycol 2.0 Carboxy Vinyl Polymer 0.1 PEG 12 nonylphenyl ether 0.2 Polysorbate 80 0.4 ethanol 10.0 Triethanolamine 0.1 Preservative, coloring, flavoring Quantity Purified water Remaining amount

Formulation Example 2 @ Nutritional Cream

A nutritious cream was prepared according to a conventional method with the composition described in the table below.

ingredient Content (% by weight) Compound of Example 1 2.0 Polysorbate 60 1.5 Solbitan Sesquioleate 0.5 PEG 60 Cured Castor Oil 2.0 Liquid paraffin 10. Squalane 5.0 Caprylic / Capric Triglycerides 5.0 glycerin 5.0 Butylene glycol 3.0 Propylene glycol 3.0 Triethanolamine 0.2 Preservative, coloring, flavoring Quantity Purified water Remaining amount

Formulation Example 3 Massage Cream

Massage creams were prepared according to a conventional method with the compositions described in the table below.

ingredient Content (% by weight) Compound of Example 1 1.0 Beeswax 10.0 Polysorbate 60 1.5 PEG 60 Cured Castor Oil 2.0 Sorbitan sesquioleate 0.8 Liquid paraffin 40.0 Squalane 5.0 Caprylic / Capric Triglycerides 4.0 glycerin 5.0 Butylene glycol 3.0 Propylene glycol 3.0 Triethanolamine 0.2 Preservative, coloring, flavoring Quantity Purified water Remaining amount

[Formulation Example 4] Pack

Packs were prepared according to conventional methods with the compositions described in the table below.

ingredient Content (% by weight) Compound of Example 1 0.2 Polyvinyl alcohol 13.0 Sodium Carboxymethyl Cellulose 0.2 glycerin 5.0 Allantoin 0.1 ethanol 6.0 PEG 12 nonylphenyl ether 0.3 Polysorbate 60 0.3 Preservative, coloring, flavoring Quantity Purified water Remaining amount

Claims (7)

Ginsenoside fatty acid ester compound which is any one of the compounds represented by the following formula (2):
[Formula 2]

[Formula 3]

[Formula 4]

[Formula 5]

delete delete Represented by Scheme 1 below,
A method for preparing a ginsenoside fatty acid ester compound of Formula 1 prepared by enzymatic conversion of a compound of Formula 6 to a saturated or unsaturated fatty acid vinyl ester of C12 to C22:
Scheme 1

(The ginsenoside fatty acid ester compound represented by the formula (1),
R ₁ is OH, R ₂ is a palmityl group, R ₃ is H (compound 2 of claim 1), or
R ₁ is OH, R ₂ is palmityl group, R ₃ is OH (Compound ₃ of claim 1), or
R ₁ and R ₂ is a palmityl group, R ₃ is H (Compound 4 of claim 1), or
R ₁ and R ₂ are palmityl groups, R ₃ is OH (Formula 5 of claim 1),
In Formula 6, R ₃ is H or OH,
The saturated or unsaturated fatty acid vinyl ester compound of C12 to C22 is vinyl palmitate) delete The method of claim 4, wherein
The enzyme conversion reaction is flavozyme ( flavourzyme ), protease A ( protease A), alcalase ( sacalase ), savinase ( savinase ), protamex ( protamex ), esperase ( nosperzyme ), novozyme Method for producing a ginsenoside fatty acid ester compound, characterized in that using one enzyme selected from the group consisting of esterase , acylase and mixtures thereof. Cosmetic composition comprising the ginsenoside fatty acid ester compound according to claim 1 as an active ingredient.

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