CN114632018A - Skin external composition containing neohesperidin dihydrochalcone - Google Patents
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- CN114632018A CN114632018A CN202111468885.4A CN202111468885A CN114632018A CN 114632018 A CN114632018 A CN 114632018A CN 202111468885 A CN202111468885 A CN 202111468885A CN 114632018 A CN114632018 A CN 114632018A
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/60—Sugars; Derivatives thereof
- A61K8/602—Glycosides, e.g. rutin
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
- A61K31/7034—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/14—Drugs for dermatological disorders for baldness or alopecia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/005—Preparations for sensitive skin
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/08—Anti-ageing preparations
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q7/00—Preparations for affecting hair growth
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Abstract
One embodiment relates to a composition for external use for skin comprising neohesperidin dihydrochalcone as an effective ingredient for promoting ceramide biosynthesis and improving skin barrier. The skin external composition comprising neohesperidin dihydrochalcone according to an embodiment activates enzymes that play an important role in the ceramide production phase, promotes ceramide biosynthesis, and thus has an excellent effect of improving the skin barrier. In addition, the composition has no side effects such as cytotoxicity and skin irritation even after long-term use.
Description
Technical Field
The present invention relates to a skin external composition comprising neohesperidin dihydrochalcone.
Background
The skin is composed of epidermis (epidermis), dermis (dermis) and subcutaneous tissue (subetis), and plays a barrier role in preventing body fluid loss and protecting a human body from external harmful factors based on keratin cells and intercellular lipids of the epidermis.
The Skin barrier (Skin barrier) can maintain its function only in the case where the Stratum corneum (Stratum corneum), which is located at the uppermost part of the epidermis, is normally formed.
In order to improve the skin barrier, various forms of topical therapies utilizing ceramides (or synthetic pseudoceramides) are being attempted. However, natural ceramides are limited in use due to their high price and safety issues, and synthetic ceramides that are the same as or similar to natural ceramides are also problematic in that they are difficult to be formulated into various dosage forms due to their high price and low solubility.
Therefore, the present inventors have made an effort to develop a safe skin external composition for promoting the biosynthesis of ceramide in the skin, having an effect of improving the skin barrier, and having no side effects when applied to the skin, in order to solve the above problems, thereby completing the present invention.
Disclosure of Invention
Problems to be solved by the invention
One embodiment provides a composition for external use for skin, which has few side effects, is safe to the human body, and has an excellent skin barrier improvement effect.
Means for solving the problems
One embodiment provides a composition for external application to the skin, comprising Neohesperidin dihydrochalcone (Neohesperidin dihydrochalcone) as an active ingredient.
The skin external composition may be a composition for improving skin barrier and skin moisturizing.
The neohesperidin dihydrochalcone may be included in an amount of 0.00001 to 10% by weight, relative to the total weight of the skin external preparation composition.
The neohesperidin dihydrochalcone can promote the biosynthesis of ceramide.
The neohesperidin dihydrochalcone can activate Serine Palmitoyl Transferase (SPT), ceramide synthase (CerS), glucosylceramide synthase (GCS), Glucocerebrosidase (GBA) or Acid Sphingomyelinase (ASM).
The concentration of the neohesperidin dihydrochalcone can be 1 mu g/mL to 100 mu g/mL.
The skin external composition may be a cosmetic composition.
The skin external composition may be a hair composition for improving the scalp.
The skin external composition may be a pharmaceutical composition for improving skin barrier and skin moisturization.
Effects of the invention
The skin external composition comprising neohesperidin dihydrochalcone according to an embodiment promotes ceramide biosynthesis, thereby strengthening a skin barrier, improving skin moisturizing ability, and having the effect of relieving or improving dry skin symptoms and allergic symptoms.
In addition, the skin external composition containing neohesperidin dihydrochalcone according to an embodiment has the effects of improving wrinkles of facial skin, improving scalp, preventing hair loss, and promoting hair growth by strengthening skin barrier, improving skin softness and firmness, and increasing skin moisturizing ability.
Drawings
Fig. 1 is a graph showing the degree of increase in ceramide biosynthesis when keratin cells are treated with neohesperidin dihydrochalcone according to experimental example 2 of an embodiment.
Fig. 2 is a graph showing the degree of change in the amount of moisture loss through skin when example 1 and comparative example 1 were coated according to experimental example 4 of an example.
Detailed Description
The present invention is described in more detail below.
One embodiment relates to a composition for external use for skin comprising neohesperidin dihydrochalcone as an effective ingredient.
The term "Neohesperidin dihydrochalcone (Neohesperidin dihydrochalcone)" used in the present specification is a compound represented by the structural formula 2 below. The molecular formula of the neohesperidin dihydrochalcone is C28H36O15And the molecular weight is 612.58.
In one embodiment, neohesperidin dihydrochalcone that can be used includes neohesperidin dihydrochalcone isolated from a plant containing neohesperidin dihydrochalcone, synthetic neohesperidin dihydrochalcone, commercially available neohesperidin dihydrochalcone.
[ chemical formula 2]
According to one embodiment, the skin external composition may be a composition for improving skin barrier and skin moisturizing.
The skin external agent composition according to an embodiment includes neohesperidin dihydrochalcone that biosynthesizes ceramide.
The skin barrier function is largely influenced by the composition (organization) and structure (organization) of lipids. Intercellular keratinocyte lipids are composed of ceramide, cholesterol, and free fatty acids at the same molar ratio (equivalent ratio), and it has been reported that ceramide is reduced in dry skin or skin with impaired skin barrier such as atopic dermatitis, acne skin, and aged skin. Skin barrier dysfunction, a 2-5 fold increase in transdermal water loss (TEWL) and a decrease in the water content of the stratum corneum were observed in the skin of atopic dermatitis patients, and were found to be mainly caused by a decrease in stratum corneum lipids, particularly, ceramide. Therefore, the content of ceramide has an effect on improving skin barrier and skin moisturization, and the composition for external skin preparation in one embodiment capable of biosynthesizing ceramide may be used as a composition for improving skin barrier and skin moisturization. For example, it can be used as a functional cosmetic capable of treating skin having an impaired skin barrier such as atopic dermatitis, acne skin and aged skin, or as a functional cosmetic composition capable of preventing before damage.
The skin external agent composition according to an embodiment may include the neohesperidin dihydrochalcone in an amount of 0.00001 wt% to 10 wt%, preferably, 0.0001 wt% to 5 wt%, with respect to the total weight of the composition. In the case where the composition of one embodiment contains the neohesperidin dihydrochalcone in an amount of less than 0.00001 wt%, a sufficiently effective effect cannot be expected, and when the content exceeds 10 wt%, the stability of the formulation is lowered, and an undesirable skin reaction such as contact dermatitis may occur. According to one example, the neohesperidin dihydrochalcone may activate Serine Palmitoyltransferase (SPT), ceramide synthase (CerS), glucosylceramide synthase (GCS), Glucocerebrosidase (GBA), or Acid Sphingomyelinase (ASM).
According to one embodiment, the skin external composition may be a cosmetic composition for preventing aging and improving wrinkles.
According to an embodiment, the skin external agent composition may be a hair composition for improving the scalp.
According to one embodiment, the skin external composition may be a pharmaceutical composition for improving skin barrier and skin moisturization.
The skin external composition of one embodiment comprises, in addition to the neohesperidin dihydrochalcone for promoting ceramide biosynthesis and improving the skin barrier, moisturizers, thickeners, surfactants, oily bases, preservatives, antioxidants, ethanol, perfumes, pH adjusters, natural extracts, and the like, which can be easily selected and formulated by those skilled in the art within a range that does not impair the effects of the present invention, and in this case, produces a synergistic effect when applied together with other raw materials.
The skin external composition may be a cosmetic composition, a hair composition for improving the scalp, or a pharmaceutical composition.
The formulation of the cosmetic composition is not particularly limited and may be appropriately selected depending on the purpose. For example, the cosmetic composition may be formulated into softening lotion, astringent lotion, nourishing lotion, massage cream, essence, nourishing cream, facial mask, powder, wax cream, etc., but is not limited thereto.
The hair composition for improving scalp may be in the form of shampoo, conditioner, hair rinse, hair mask, etc., but is not limited thereto.
The pharmaceutical composition may be in the form of a transdermal administration form such as emulsion, ointment, gel, cream, patch, etc., but is not limited thereto.
The pharmaceutical composition can be used for skin barrier related diseases, including atopic dermatitis, dermatitis caused by skin roughness, etc., miliaria, fester, frostbite, diaper-caused skin diseases, contact dermatitis, seborrheic dermatitis, lichen simplex chronicus, nummular eczema, housewife eczema, solar dermatitis, insect bite dermatitis, skin pruritus, prurigo, drug eruption, toxic eruption, psoriasis, parapsoriasis, palmoplastic impetigo, lichen planus, lichen glossus, pityriasis rubra pilaris, scab, erythroderma, discoid lupus erythematosus, systemic lupus erythematosus, pemphigus, pemphigoid, dermatitis herpetiformis, alopecia areata, vitiligo vulgaris, sarcoidosis, cutaneous amyloidosis, keloid, hypertrophic scars, wounds, bedsores, skin ulcers, alopecia, hair nourishment and hair growth.
In the skin external composition of each dosage form, those skilled in the art can easily select and formulate other ingredients than the skin external composition of the examples according to the dosage form or the purpose of use, etc., and in this case, when it is applied simultaneously with other raw materials, a synergistic effect is produced.
The present invention will be described in more detail below with reference to examples and experimental examples. This is for the purpose of illustrating the invention only and the scope of the invention is not limited thereto.
<Experimental example 1>Evaluation of expression of enzyme involved in ceramide-producing Process
To evaluate the expression of the enzyme involved in ceramide production by neohesperidin dihydrochalcone, human keratin cells (HaCaT cells) were first cultured in DMEM medium containing 10% FBS and 1% P/S at 2.5X 105Cell/well (cells/well) concentrations were seeded in 6-well plates and 24 hours later neohesperidin dihydrochalcone was applied to human keratinocyte cells at concentrations of 1. mu.g/mL, 10. mu.g/mL, 100. mu.g/mL.
For measuring the amount of gene expression, easy-spin was usedTMTotal RNA extraction reagentCassette (iNtRoN, Korea), total RNA was extracted from the cells. The extracted RNA was synthesized into cDNA using mactam RT PreMix (maxim RT PreMix, inn ron, korea), real-time PCR was performed using ABI 7500 rapid real-time PCR system (applied biosystems, usa), and the gene expression amounts of Serine Palmitoyltransferase (SPT), ceramide synthase (CerS), Glucose Ceramide Synthase (GCS), Glucocerebrosidase (GBA), and Acid Sphingomyelinase (ASM) were confirmed. At this time, as a negative control group, a group not subjected to neohesperidin dihydrochalcone treatment was used, and as an internal control group, mRNA of GAPDH was used.
As a result, as shown in table 1 below, it was confirmed that the treatment with neohesperidin dihydrochalcone increased the gene expression of the ceramide production-related enzymes SPT, CerS, GCS, GBA, and ASM.
[ TABLE 1 ]
| (control treatment ═ 1) | SPT | CerS | GCS | GBA | |
| Neohesperidin dihydrochalcone | |||||
| 1 mu g/mL | 1.2 | 1.2 | 1.3 | 1.2 | 1.2 |
| |
1.8 | 1.7 | 1.5 | 1.4 | 1.5 |
| |
2.8 | 2.8 | 2.7 | 2.8 | 2.5 |
<Experimental example 2>Confirmation test for increase in ceramide production
To measure the effect of increasing the amount of ceramide production by neohesperidin dihydrochalcone, human keratin cells (HaCaT cells) were cultured in DMEM medium containing 10% FBS and 1% P/S at 2.5X 105Cell/well (cells/well) concentrations were seeded in 6-well plates and after 24 hours neohesperidin dihydrochalcone was applied to human keratinocyte cells at concentrations of 1. mu.g/mL, 10. mu.g/mL, 100. mu.g/mL. After 48 hours of culture, the amount of ceramide dissolved out from the medium was measured using an enzyme-linked immunosorbent assay kit (Mybiosource, usa). As a negative control group, a group which was not subjected to neohesperidin dihydrochalcone treatment was used.
As a result, as shown in FIG. 1, it was confirmed that the amount of ceramide production was increased by neohesperidin dihydrochalcone.
<Experimental example 3>Skin safety test
In order to evaluate the degree of irritation to the skin, a skin patch test (Human patch test) was performed. The skin patch test was conducted on 30 normal persons over 20 years old, samples were prepared in a 0.1%, 1%, 10% aqueous solution, and attached to the inner upper arm part for 48 hours using a Finn chamber (Finn chamber), and the skin reaction results were evaluated by first interpretation after removal and second interpretation after 72 hours. The evaluation criteria and the stimulation index were calculated as shown in table 2 and mathematical formula 1, and the results are shown in table 3.
[ TABLE 2]
| Reaction of | Weighted values | Evaluation criteria |
| - | 0.0 | No reaction |
| ± | 0.5 | Suspected positive reaction |
| + | 1.0 | Weak positive reaction |
| ++ | 2.0 | Strong positive reaction |
| +++ | 3.0 | Very positive reaction |
< equation 1>
Skin irritation index ═ Σ (weighted value X number of responding persons)/(highest weighted value X total number of tested persons) × 100
[ TABLE 3 ]
| Index of skin irritation | Degree of irritation | |
| Neohesperidin dihydrochalcone (0.1 wt%) | 0.0 | Has no irritation |
| Neohesperidin dihydrochalcone (1 wt%) | 0.0 | Has no irritation |
| Neohesperidin dihydrochalcone (10 wt%) | 0.0 | Has no irritation |
The experimental result shows that the neohesperidin dihydrochalcone has no stimulation to the skin at the weight percent of less than 10 percent, and when the neohesperidin dihydrochalcone is used as a raw material of the skin external preparation, the neohesperidin dihydrochalcone is judged to have no stimulation to the skin.
<Experimental example 4>Skin barrier improvement test measured by transdermal moisture loss (TEWL)
In order to confirm the skin barrier improvement effect of the skin external agent composition according to an embodiment, the inventors prepared cream compositions as shown in example 1 and comparative example 1 of table 4 below and then performed the following skin barrier improvement experiment.
[ TABLE 4 ]
The skin barrier improvement test was evaluated by measuring the amount of percutaneous Water Loss (Transepidermal Water Loss: TEWL) after neohesperidin dihydrochalcone was applied to the skin.
Experiments were performed using example 1 and comparative example 1 in which 10 adults aged 30 to 43 years were used, and two 1.5cm × 1.5cm regions were provided on the inner forearm side of the subject as test sites.
First, after measuring the amount of percutaneous water loss at a test site using a percutaneous water loss measuring device (Vapometer percutaneous water loss measuring instrument, Delfin Technologies, finland), the stratum corneum at the test site was removed by tape stripping technique (tape striping) to artificially damage the skin barrier. After the skin barrier injury, example 1 and comparative example 1 were applied to the test site 2 times a day, and the amount of percutaneous water loss was measured after 1 day, 3 days, and 5 days.
The amount of moisture (g/m) lost through the skin of example 1 and comparative example 1 was measured2h) The variation is shown in figure 2.
As a result of the experiment, it was found that the transdermal water loss value was decreased in the application example 1 and the skin barrier improvement effect was excellent as compared with the application comparative example 1.
Based on the results of the above experimental examples, various dosage forms using neohesperidin dihydrochalcone were prepared and shown below. However, those skilled in the art will appreciate that these dosage form examples are merely illustrative examples and that the dosage forms of the examples are not limited to these dosage form examples.
<Dosage form example 1>Softening lotion (skin)
toner)
[ TABLE 5 ]
| Name of composition | Content (wt%) |
| Neohesperidin dihydrochalcone | 0.5 |
| Glycerol | 5.0 |
| 1, 3-butanediol | 3.0 |
| Ethanol | 3.0 |
| Polyoxyethylene nonyl phenyl ether | 0.5 |
| Perfume | Proper amount of |
| Preservative | Proper amount of |
| Purified water | Residual amount of |
<Dosage form example 2>Astringent lotion (astringent)
[ TABLE 6 ]
| Name of the ingredient | Content (wt%) |
| Neohesperidin dihydrochalcone | 0.5 |
| Glycerol | 3.0 |
| Citric acid | 0.1 |
| Ethanol | 5.0 |
| Polyoxyethylene oleyl ether | 1.0 |
| Sorbitol | 2.0 |
| Perfume | Proper amount of |
| Preservative | Proper amount of |
| Purified water | Residual amount of |
<Dosage form example 3>Emulsion and method of making
[ TABLE 7 ]
<Dosage form example 4>Cream (create)
[ TABLE 8 ]
| Name of composition | Content (wt%) |
| Neohesperidin dihydrochalcone | 0.5 |
| Glycerol | 5.0 |
| Stearic acid | 8.0 |
| Squalane | 5.0 |
| Self-emulsifying glyceryl monostearate | 2.5 |
| Polyoxyethylene sorbitan monostearate | 1.5 |
| Propylene glycol | 4.0 |
| Glycyrrhetinic acid stearyl alcohol ester | 0.2 |
| Vaseline | 2.0 |
| Oxidation preventive | Proper amount of |
| Perfume | Proper amount of |
| Preservative | Proper amount of |
| Purified water | Residual amount of |
In one embodiment, as shown in the above tables 5 to 8, the skin external composition of various dosage forms configured with neohesperidin dihydrochalcone shows excellent effects in promoting ceramide biosynthesis and improving skin barrier.
Claims (9)
1. A composition for external use on skin comprises neohesperidin dihydrochalcone as an active ingredient.
2. The composition for external application to skin according to claim 1,
the skin external composition is a composition for improving skin barrier and skin moisture.
3. The composition for external preparation for skin according to claim 1,
the neohesperidin dihydrochalcone is contained in an amount of 0.00001 to 10 wt% with respect to the total weight of the skin external preparation composition.
4. The composition for external preparation for skin according to claim 1,
the neohesperidin dihydrochalcone promotes ceramide biosynthesis.
5. The composition for external preparation for skin according to claim 1,
the neohesperidin dihydrochalcone activates serine palmitoyl transferase, ceramide synthase, glucose ceramide synthase, glucocerebrosidase or acid sphingomyelinase.
6. The composition for external application to skin according to claim 1,
the concentration of the neohesperidin dihydrochalcone is 1 mu g/mL-100 mu g/mL.
7. The composition for external skin application according to any one of claims 1 to 6,
the skin external composition is a cosmetic composition.
8. The composition for external skin preparation according to any one of claims 1 to 6,
the external composition for skin is a composition for hair for improving the scalp.
9. The composition for external skin application according to any one of claims 1 to 6,
the skin external composition is a pharmaceutical composition for improving skin barrier and skin moisture.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR10-2020-0175492 | 2020-12-15 | ||
| KR1020200175492A KR102295487B1 (en) | 2020-12-15 | 2020-12-15 | Skin external composition comprising neohesperidin dihydrochalcone |
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| CN114632018A true CN114632018A (en) | 2022-06-17 |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115006271A (en) * | 2022-06-20 | 2022-09-06 | 广州百肤科技有限公司 | Efficient anti-aging moisturizing soothing repairing anti-wrinkle face cream containing neohesperidin dihydrochalcone extract |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101583345A (en) * | 2006-11-02 | 2009-11-18 | 美露香株式会社 | Ceramide synthesis accelerators, cosmetic preparation, skin preparation for external use, method of preventing aging, and method of diminishing wrinkle |
| FR2946253A1 (en) * | 2009-06-08 | 2010-12-10 | Oreal | Cosmetic kit, useful e.g. to treat oxidative stress, comprises first anhydrous composition having vitamin C, and second composition having neohesperidin dihydrochalcone, silicone elastomer and concave particles |
| CN110022850A (en) * | 2016-11-29 | 2019-07-16 | 莱雅公司 | Composition comprising truffle extract and neohesperidin dihydrochalcone |
-
2020
- 2020-12-15 KR KR1020200175492A patent/KR102295487B1/en active IP Right Grant
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2021
- 2021-12-03 CN CN202111468885.4A patent/CN114632018A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101583345A (en) * | 2006-11-02 | 2009-11-18 | 美露香株式会社 | Ceramide synthesis accelerators, cosmetic preparation, skin preparation for external use, method of preventing aging, and method of diminishing wrinkle |
| FR2946253A1 (en) * | 2009-06-08 | 2010-12-10 | Oreal | Cosmetic kit, useful e.g. to treat oxidative stress, comprises first anhydrous composition having vitamin C, and second composition having neohesperidin dihydrochalcone, silicone elastomer and concave particles |
| CN110022850A (en) * | 2016-11-29 | 2019-07-16 | 莱雅公司 | Composition comprising truffle extract and neohesperidin dihydrochalcone |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115006271A (en) * | 2022-06-20 | 2022-09-06 | 广州百肤科技有限公司 | Efficient anti-aging moisturizing soothing repairing anti-wrinkle face cream containing neohesperidin dihydrochalcone extract |
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