CN106420605A - Skin external-applying preparation based on quasi-ceramide and paeonol and production method thereof - Google Patents

Skin external-applying preparation based on quasi-ceramide and paeonol and production method thereof Download PDF

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CN106420605A
CN106420605A CN201610843009.8A CN201610843009A CN106420605A CN 106420605 A CN106420605 A CN 106420605A CN 201610843009 A CN201610843009 A CN 201610843009A CN 106420605 A CN106420605 A CN 106420605A
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ceramide
paeonol
skin
preparation
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李维宽
杜雪琴
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Suzhou Yao Jimeiyan Pharmaceutical Technology Co Ltd
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Suzhou Yao Jimeiyan Pharmaceutical Technology Co Ltd
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    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/10—Dispersions; Emulsions
    • 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
    • A61K31/12—Ketones
    • 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
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A61K31/164—Amides, e.g. hydroxamic acids of a carboxylic acid with an aminoalcohol, e.g. ceramides
    • 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
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
    • A61K31/221—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin with compounds having an amino group, e.g. acetylcholine, acetylcarnitine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
    • A61K31/223—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin of alpha-aminoacids
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/401—Proline; Derivatives thereof, e.g. captopril
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/12—Carboxylic acids; Salts or anhydrides thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/22—Heterocyclic compounds, e.g. ascorbic acid, tocopherol or pyrrolidones
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/28—Steroids, e.g. cholesterol, bile acids or glycyrrhetinic acid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/44—Oils, fats or waxes according to two or more groups of A61K47/02-A61K47/42; Natural or modified natural oils, fats or waxes, e.g. castor oil, polyethoxylated castor oil, montan wax, lignite, shellac, rosin, beeswax or lanolin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0014—Skin, i.e. galenical aspects of topical compositions

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  • Dermatology (AREA)
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Abstract

The invention discloses a skin external-applying preparation based on quasi-ceramide and paeonol and a production method thereof. The skin external-applying preparation is prepared from, by weight, 10-100 parts of quasi- ceramide compounds, 200-900 parts of water, 1-50 parts of steroidal compounds, 1-20 parts of paeonol, 1-50 parts of fatty acid, 0.01-30 parts of anti-inflammatory components, 0.1-50 parts of antioxidant function components and 2-20 parts of a water-phase thickening agent. According to the mode, the skin external-applying preparation based on the quasi-ceramide and the paeonol and the production method thereof are prepared based on the quasi-ceramide and the paeonol, the skin external-applying preparation can be used for skin treatment and caring and treating or treating some skin symptoms in an auxiliary mode, and particularly can be used for treating dermatitis symptoms such as atopic dermatitis, eczema, acne, seborrheic dermatitis, contact dermatitis, allergic dermatitis, solar dermatitis and Insect biting; for glandula sebacea active areas, the oil-free formula is required; for glandula sebacea inactive areas, the oil-containing formula can be adopted.

Description

Based on preparation for external application to skin and its production method of intending ceramide and paeonol
Technical field
The present invention relates to inflammatory skin external preparation field, more particularly to a kind of based on plan ceramide and paeonol Preparation for external application to skin and its production method.
Background technology
Skin is the organ of human body maximum, and weight is about the 16% of human body, about 1.5 square metres of adult's area.Skin by Epidermis, corium and subcutaneous tissue are constituted, and human internal environment are stablized of crucial importance.Skin has barrier, absorption, sensation, secretion Excretion, thermoregulation, metabolism and immunologic function.Skin also includes various appendages, such as sebaceous gland, hair, sweat gland and fingernail Deng, and abundant blood vessel, lymphatic vessel, N＆M.
Epidermis shallow is divided into basal layer, spinous layer, granular layer, clear layer and horny layer by being deep to.The critically important effect of epidermis One of be exactly barrier action, mainly realized by horny layer.Horny layer is by the keratinocyte of flattening of lost cell core and thin Extracellular lipid components are constituted, and extracellular lipid constitutes lipid barrier.Lipid mainly consist of ceramide (ceramide), cholesterol (cholesterol) and fatty acid (fatty acid).The mol ratio of these three lipids is about 1:1: 1.When the ratio of each component deviates normal ratio, lipid barrier function reduces, and causes across transepidermal water loss (transepidermal Water loss, TEWL) speed increase, water content of stratum corneum decline.On the other hand, the barrier function of reduction can cause to carry out material Permeability increase so that extraneous stimulation is more prone to reach deep skin, body is caused to stimulate or injure (Elias, P.M., 2008, Skin barrier function.Current allergy and asthma reports, 8 (4):299- 305；Proksch,E.,J.M.Brandner and J.M.Jensen,2008,The skin:An indispensable barrier.Experimental dermatology,17(12):1063-1072).
In the dermatosiss of some Chronic inflammation, such as acne, eczema, atopic dermatitiss and rosacea etc., skin screen Barrier has been damaged, and shows as red swelling of the skin heat, across transepidermal water loss increase, to stimulus object (such as face cleaning activating agent, dust mite) sensitivity Increase and (Lebwohl, M.and L.G.Herrmann, the 2005.Impaired skin barrier such as skin pruritus function in dermatologic disease and repair with moisturization.Cutis,76 (6Suppl):7-12).The relative shortage of the total amount of inflammation epiderm skin ceramide is the reason for causing skin barrier function to reduce One of (Cork, M.J., S.G.Danby, Y.Vasilopoulos, J.Hadgraft, M.E.Lane, M.Moustafa, R.H.Guy,A.L. Macgowan,R.Tazi-Ahnini and S.J.Ward,2009.Epidermal barrier dysfunction in atopic dermatitis.The Journal of investigative dermatology,129 (8):1892-1908；Elias,P.M.,2014.Lipid abnormalities and lipid-based repair strategies in atopic dermatitis.Biochimica et biophysica acta,1841(3):323- 330).And inflammation itself can slow down the recovery process of skin barrier, so as to form vicious cycle.The Asia of some non-evident symptons In clinical dermatitis, the damage of skin barrier is also relatively common.This kind of crowd stimulation external to some, such as temperature change and wet Degree change etc. is more more sensitive than general population.When the barrier function of skin is damaged, skin will start a series of biochemical process Barrier is repaired, such as accelerate the synthesis of lipid, including accelerating the synthesis of ceramide, cholesterol and fatty acid.Comparatively, The synthesis of ceramide is that comparison is slow, and therefore the recovery extent of ceramide content also reflects the journey of skin barrier reparation Degree.
For because epidermis is relative lacks the lipid barrier damage that ceramide causes, can be covered by external oils External preparation based on agent, ceramide is recovering barrier.The effect of oils is to form masked film immediately, plays certain screen Barrier is acted on, but the oils and fatss of external cannot be merged with the natural lipid of epidermis, and external ceramide type material, then can be with table The lipid layer fusion of skin, seamless reparation skin barrier.Effect and weak effect glucocorticoid using this strategy of ceramide Similar, but the side effect without glucocorticoid (Kircik, L., F.Hougeir and J.Bikowski, 2013.Atopic dermatitis,and the role for a ceramide-dominant,physiologic lipid-based barrier repair emulsion.Journal of drugs in dermatology:JDD,12 (9):1024-1027；Meckfessel,M.H.and S.Brandt,2014.The structure,function,and importance of ceramides in skin and their use as therapeutic agents in skin- care products.Journal of the American Academy of Dermatology,71(1):177-184). The ceramide for being used can be natural ceramide, or biosynthesiss or chemosynthesis with natural knot The ceramide of structure.Additionally, the structure of also class synthesis and material as natural ceramide type, referred to as intend ceramide (pseudoceramide).The effect for intending ceramide is similar with natural ceramide, can form fat with cholesterol, fatty acid Matter layer, repair of skin barrier.The skin barrier preparation of commercialization includes Epiceram, Mimyx, Atopiclair, Eletone Deng.Epiceram formula contains mineral oil, silicone oil, intends ceramide PC-104, conjugated linoleic acid, cholesterol etc.. Atopiclair based on synthetic ester oil, containing for Mei Sitan, Fructus Vitis viniferae extract and glycyrrhetinic acid.Mimyx with squalane is Basis, containing N- Palmitylethanolamide.Eletone is then O/W (oil-in-water) emulsion of oil content up to 70%.
For the skin of Chronic inflammation, except barrier breakdown, also inflammation and oxidative pressure.Therefore, for such skin In the external preparation of skin disease, antiinflammatory antioxidant content will promote the recovery of skin.Paeonol, from Cortex Moutan, due to tool Antiinflammatory, antiallergic, antioxidation etc. is had to act on.The antiinflammatory of paeonol and antioxidation and blocking MAPK/ERK/p38 signal path Relevant (Jin, X., J.Wang, Z.M.Xia, C.H.Shang, Q.L.Chao, Y.R.Liu, H.Y.Fan, D.Q.Chen, F.Qiu and F.Zhao,2016.Anti-inflammatory and anti-oxidative activities of paeonol and its metabolites through blocking mapk/erk/p38signaling pathway.Inflammation,39(1):434-446).The acute injury of kidney that paeonol protection endotoxin causes, mechanism of action Be suppression TLR4 and NF-kB signal path (Fan, H.Y., D.Qi, C.Yu, F.Zhao, T.Liu, Z.K.Zhang, M.Y.Yang, L.M.Zhang,D.Q.Chen and Y.Du,2016.Paeonol protects endotoxin-induced acute kidney injury:Potential mechanism of inhibiting tlr4-nf-kappab signal pathway.Oncotarget.DOI 10.18632/oncotarget.8347).The antioxidation of paeonol is also embodied in drop Low free radical, and protection neurocyte (Wang, H., Z.M.Geng, Z.W.Hu, S.Y.Wang and B.Zhao, 2015. [neuroprotective effects of paeonol in a cell model of parkinson disease] .Journal of Zhejiang University.Medical sciences,44(1):30-36), high-order albumen oxygen is resisted Change product cause oxidative pressure (Ping, M., W.Xiao, L.Mo, X.Xiao, S.Song, W.Tang and X.Yang, 2014.Paeonol attenuates advanced oxidation protein product-induced oxidative stress injury in thp-1macrophages.Pharmacology,93(5-6):286-295.DOI 10.1159/ 000363577).The antiinflammatory action of paeonol be also embodied in reduce PGE2 synthesis and reduce COX-2 expression on (Li, M., S.Y.Tan and X.F.Wang,2014.Paeonol exerts an anticancer effect on human colorectal cancer cells through inhibition of pge(2)synthesis and cox- 2expression.Oncology reports,32(6):2845-2853.DOI 10.3892/or.2014.3543).Paeonol Have been used in external preparation.The paeonol of (the tenth page 30 of Traditional Chinese medicine historical preparation) containing 5% paeonol unguentum, for wet The dermatopathies such as rash, dermatitis, prurituss, mosquito bite.However, as paeonol unguentum is with fatty acid as substrate, soap is Emulsifying agent, has certain zest to skin.Excess fat acid external, the ceramide-gallbladder that can also destroy sebum lipid is solid The ratio of alcohol-fatty acid, damages skin barrier.
Content of the invention
The present invention solves the technical problem of providing a kind of based on the external preparation for skin system for intending ceramide and paeonol Agent and its production method, solve the problems, such as barrier breakdown, inflammation and the oxidative pressure of inflammatory skin illness, carry out skin barrier and repair Multiple, antiinflammatory and antioxidation.
For solving above-mentioned technical problem, one aspect of the present invention is：There is provided a kind of based on plan ceramide With the preparation for external application to skin of paeonol, including the composition of following weight portion：Intend 10～100 parts of Ceramide compound, water 200～ 900 parts and 1～20 part of paeonol, the plan Ceramide compound is following structure I～VIII
One or more in shown, the chemical constitution of the paeonol is IX
Due to intending ceramide type compound, there is amphiphilic structure characteristic, itself there is certain emulsifying capacity, melt molten Can be added water after solution paeonol direct emulsifying.With homogenizer, suspension is dispersed into again after cooling.
In a preferred embodiment of the present invention, the R for intending in Ceramide compound1、R2For carbon number 10～40 The saturation of straight or branched or undersaturated alkyl, R1、R2Identical or different.
In a preferred embodiment of the present invention, in the preparation for external application to skin based on plan ceramide and paeonol also Including one or more in the composition of following weight portion：1～50 part of steroidal compounds, 1～50 part of fatty acid, antiinflammatory component 0.01～30 part, 0.1～50 part of anti-oxidation function component and 2～20 parts of water phase thickener, the steroidal compounds be cholesterol, One or more in cholesterol fatty acid ester, plant sterol and phytosterin fatty acid ester, the fatty acid be containing carbochain One or more in the saturation of length 8～30 or undersaturated straight or branched fatty acid, the water phase thickener is xanthan Glue, AVC, 2-(Acryloyloxy)ethanol/sodium acryloyldimethyl taurate copolymers, poly- third One or more in enoyl- dimethyltaurine sodium, sodium acryloyldimethyl taurate/acrylamide/VP copolymer, institute Stating in the preparation for external application to skin based on plan ceramide and paeonol does not include ethanol, ethylene glycol, Propylene Glycol, butanediol, isopropyl Alcohol, pentanediol.
In a preferred embodiment of the present invention, the preparation for external application to skin based on plan ceramide and paeonol is also wrapped Include the oils and fatss of 0～300 weight portion, the oils and fatss are animal and plant fat, animals and plants wax, ore deposit are cured, mineral oil, alkanes, silicone oil, One or more in three ester of synthetic glycerine, fatty acid ester fatty alcohol, paraffin, wax, silicone oil, siloxanes.
In a preferred embodiment of the present invention, the antiinflammatory group be divided into N- fatty acyl ethanolamine, 4- tert. butyl cyclohexanol, Tea polyphenols, bisabolol, ginger-root extract, Olibanum extract, peony root extractive, glycyrrhetate, glycyrrhetinic acid, green tea are extracted Thing, decoyl Glycine, Monooctamoin, zinc salt, epigallocatechin gallate (EGCG) EGCG, pyridoxol, nicotiamide, urine Bursin, resveratrol, N, N- (double 2- hydroxyethyls) nonanedioyl amine, Radix Arnebiae extract, Herba portulacae extract, Aloe extract, One or more in camomile extract and Semen Vitis viniferae extract.
In a preferred embodiment of the present invention, the anti-oxidation function component is tocopherol, tocopherol acetate, fertility Phenol propionic ester, tocopherol fatty acid ester, tocopherol phosphate sodium, ascorbic acid, L-AA -2- glucoside, 2-O- ethyl Ascorbic acid, 3-O- ethylascorbyl, aminopropanol ascorbic acid phosphoric acid esters, Vitamin C dipalmitate, ascorbic acid Magnesium phosphorate, NAP, Ascorbyl Tetraisopalmitate, resveratrol, beta-carotene, Ubidecarenone, Chinese mugwort One or more in Di Ben, astaxanthin, alpha-lipoic acid, soybean isoflavone, ginkgetin and glutathion.
In a preferred embodiment of the present invention, the pH based on the preparation for external application to skin for intending ceramide and paeonol Being worth for 4.5～5.5, pH value is adjusted using 2-pyrrolidone-5-carboxylic acid's aqueous solution or KOH aqueous solution.
In a preferred embodiment of the present invention, the preparation for external application to skin based on plan ceramide and paeonol is also wrapped The emulsifying agent of 1～50 weight portion is included, the emulsifying agent is span-TWEEN Series, alkyl polyglucoside-fatty alcohol series, glycerol list are hard One or more in fat acid ester/PEG100 stearate.
In a preferred embodiment of the present invention, the preparation for external application to skin based on plan ceramide and paeonol is also wrapped The preservative of 1～20 weight portion is included, the preservative is hexanediol, ethohexadiol, Sensiva SC50, Monooctamoin, chlorine One or more in the sweet ether of benzene.
For solving above-mentioned technical problem, one aspect of the present invention is：There is provided a kind of based on plan ceramide With the production method of the preparation for external application to skin of paeonol, comprise the following steps for：
Reactor is placed under atmosphere of inert gases, jacket temperature is set to 80～95 degrees Celsius, ceramide will be intended Compound heating and melting, adds steroidal compounds, satisfied fatty acid, paeonol, oils and fatss, emulsifying agent, stirs 0.5～10 hour Afterwards, the water of 80～90 DEG C of addition, stirring and emulsifying, homogenizing, obtain emulsion；
Treating that emulsion is cooled to room temperature, water being added, unsaturated fatty acid, antiinflammatory component, anti-oxidation function is added toward in emulsion Component and preservative, stirring, homogenizing, then with 2-pyrrolidone-5-carboxylic acid's aqueous solution that mass percent is 10% or percent mass Than the KOH aqueous solution regulation pH value for 18% to 4.5～5.5, homogenizing, water phase thickener is eventually adding, is uniformly mixing to obtain base In the preparation for external application to skin for intending ceramide and paeonol.
The invention has the beneficial effects as follows：It is a kind of based on the external preparation for skin system for intending ceramide and paeonol that the present invention is pointed out Agent and its production method, be based on intending obtained in ceramide and paeonol, skin nursing maintenance and treatment can be used for or aided in Some skin symptoms are treated, especially for atopic dermatitiss, eczema, acne, seborrheic dermatitis, contact dermatitis, anaphylaxis The dermatitis symptom such as dermatitis, solar dermatitis, sting, for sebaceous gland active regions, need using no oil formula, and are directed to Sebaceous gland not active region, then can adopt containing oil formula.
Description of the drawings
For the technical scheme being illustrated more clearly that in the embodiment of the present invention, below will be to making needed for embodiment description Accompanying drawing is briefly described, it should be apparent that, drawings in the following description are only some embodiments of the present invention, for For those of ordinary skill in the art, on the premise of not paying creative work, other can also be obtained according to these accompanying drawings Accompanying drawing, wherein：
After Fig. 1 is a kind of one preferred embodiment use of preparation for external application to skin based on plan ceramide and paeonol of the present invention Parameters variation schematic diagram.
Specific embodiment
Technical scheme in the embodiment of the present invention will be clearly and completely described below, it is clear that described enforcement Example is only a part of embodiment of the present invention, rather than whole embodiments.Based on the embodiment in the present invention, this area is common All other embodiment that technical staff is obtained under the premise of creative work is not made, belongs to the model of present invention protection Enclose.
Present invention offer is a kind of based on the preparation for external application to skin for intending ceramide and paeonol, rich in plan ceramide chemical combination Thing and paeonol, the external preparation also includes steroidal compounds and fatty acid.When described based on intending ceramide and paeonol Preparation for external application to skin is used for sebaceous gland active regions, then do not contain oils and fatss in formula；And it is inactive for sebaceous gland to work as the preparation Region, then can contain oils and fatss, can be used for nursing and the treatment of the dermatitises such as atopic dermatitis, eczema.
The plan Ceramide compound is the compound that a class and natural ceramide have similar structures, and fusing point is than natural Ceramide is low, and can repair skin barrier, can be elected to be the component of barrier reparation.Selected plan ceramide chemical combination Thing is structure I-VIII
One or more in shown.
R1、R2Saturation or undersaturated alkyl for the straight or branched of carbon atom 10-40.R1With R2Can be identical, also may be used With difference, it is possible to use the compound of single structure, it is possible to use the mixture of the multiple compounds described in I-VIII structure.Relatively In excellent scheme, R1、R2For the straight chain saturation alkane base of carbon atom 11-21, the plan Ceramide compound or its mixture molten Point is generally less than 95 DEG C.
When skin barrier function is damaged, inflammation and oxidative pressure is usually associated with.Therefore, in skin external preparation, The recovery of inflammatory skin illness be will be helpful to comprising appropriate antiinflammatory and antioxidant content.The present invention adopts paeonol, because being somebody's turn to do Composition has antiinflammatory and antioxidative effect simultaneously, while its zest to skin is little, safe.Paeonol unguentum is used In clinic for many years, including Pediatric Clinic, serious adverse reaction is had no.
The steroidal compounds are cholesterol, cholesterol fatty acid ester, plant sterol, in phytosterin fatty acid ester one Plant or multiple.Cholesterol is also one of important lipid of skin barrier.In addition to cholesterol, cholesterol fat can also be selected Acid esters is used as the precursor of cholesterol.The plant steroid compounds close with cholesterol structure, such as phytosterol and its fat Fat esters of gallic acid, acts not only as the lipid components of barrier, also has antiinflammatory action.Common plant sterol structure is as follows：
Another lipid constituent based on the preparation for external application to skin for intending ceramide and paeonol of the present invention is Fatty acid.The molar ratio for intending ceramide-steroidal compounds-fatty acid is (1.5～4.5):(0.5～1.5):(0.5～ 1.5).Fatty acid is one or more in the saturation containing carbon chain lengths 8-30 or undersaturated straight or branched fatty acid. Fatty acid, especially polyunsaturated fatty acid, with the function of supplementing the necessary fatty acid of skin, antiinflammatory.Therefore, preferable scheme It is to select linoleic acid, linolenic acid (alpha-linolenic acid and gamma-Linolenic acid), conjugated linoleic acid and carbon chain lengths straight for the saturation of 12-24 Chain fatty acid composition mixture.
The oils and fatss are animal and plant fat, animals and plants wax, ore deposit are cured, mineral oil, alkanes, silicone oil, three ester of synthetic glycerine, One or more in fatty acid ester fatty alcohol, paraffin, wax, silicone oil, siloxanes.For sebaceous gland active regions, without oils and fatss The reason for be the region smegma sebum a lot, have blocking pore possibility, if again adopt lubricant component, Pore obstruction can be aggravated, caused acne outburst or increase；And for sebaceous gland not active region, then can be become using oils and fatss Point.These oils and fatss have quick covering to act on, and have certain barrier action, are conducive to quickly reducing across transepidermal water loss.
Other anti-inflammatory components that the present invention chooses include N- fatty acyl ethanolamine, 4- tert. butyl cyclohexanol, tea polyphenols, red do not have The sweet ammonia of medicine alcohol, ginger-root extract, Olibanum extract, peony root extractive, glycyrrhetate, glycyrrhetinic acid, green tea extract, decoyl Acid, Monooctamoin, zinc salt, epigallocatechin gallate (EGCG) EGCG, pyridoxol, nicotiamide, allantoin, white hellebore Alcohol, N, N- (double 2- hydroxyethyls) nonanedioyl amine, Radix Arnebiae extract, Herba portulacae extract, Aloe extract, Flos Matricariae chamomillae are extracted One or more in thing, Semen Vitis viniferae extract.
The acid-base value of preparation is also the key factor of an impact skin physiology.The pH value of normal skin is 4.5～5.5, The preparation of the present invention, in order to safeguard the acid barrier of skin, the pH value control of preparation is between 4.5～5.5.
When skin is in certain inflammatory process, free radical and the free radical of ultraviolet generation that inflammation is produced, right Keratinocyte is a very big oxidative pressure.In order to resist oxidative pressure, in addition to paeonol, invention formulation can also be wrapped Some antioxidant contents are included, the component of the anti-oxidation function is tocopherol, tocopherol acetate, tocopherol propionic ester, fertility Phenol fatty acid ester, tocopherol phosphate sodium, ascorbic acid, L-AA 2- glucoside, 2-O- ethylascorbyl, 3-O- second Base ascorbic acid, aminopropanol ascorbic acid phosphoric acid esters, Vitamin C dipalmitate, magnesium L-ascorbyl-2-phosphate, Vitamin C Acid phosphoric acid ester sodium, Ascorbyl Tetraisopalmitate, resveratrol, beta-carotene, Ubidecarenone, Ai Diben, astaxanthin, α-sulfur One or more in octanoic acid, soybean isoflavone, ginkgetin, glutathion.
Emulsifying agent is then hard from span-TWEEN Series, alkyl polyglucoside-fatty alcohol series, glyceryl monostearate/PEG100 Fat acid ester etc..Preservative then selects comparatively gentle new system, mainly hexanediol, ethohexadiol, Sensiva SC50, glycerol Single caprylate, one or more of chlorphenesin.Wherein hexanediol, ethohexadiol, Sensiva SC50, Monooctamoin do not have List in preservative list.Water phase thickener then selection need not neutralize, in the range of the pH=4.5-5.5 stable thickening one A little macromolecules, such as xanthan gum, AVC, 2-(Acryloyloxy)ethanol/acryloyldimethyl cattle Sodium sulfonate copolymers, polypropylene acyl group dimethyltaurine sodium, sodium acryloyldimethyl taurate/acrylamide/VP copolymer.
Ethanol, ethylene glycol, Propylene Glycol, butanediol, isopropanol, pentanediol have certain destruction for skin barrier, Therefore, avoid in the preparation of the present invention using these solvents.
Embodiment one：
(the double palmitamide MEA of hydroxypropyl, corresponding in figure compounds of structure I, R to weigh plan ceramide PC-1041、R2All For 15 carbon straight chained alkyls) 100g, under atmosphere of inert gases, in the reactor heating and melting (jacket temperature is 90 DEG C).
It is subsequently adding cholesterol 19.2g, stearic acid 7.3g, Palmic acid 7.0g, paeonol 5.0g, emulsifying agent SIMULSOL 165 (Seppic company is formed by tristerin and PEG-100 stearate are compounding) 10g.
After heating about 2 hours, 85 degrees Celsius of purified water 200g being added, stirring, emulsifying, homogenizing, is cooled to room temperature and obtains Emulsion.
Emulsion 33g, plus purified water 50g is taken, is stirred.Add glycerol 2.4g, tocopherol acetass 1.0g, ethohexadiol 0.2g, Sensiva SC50 0.1g, Monooctamoin 0.7g, epigallocatechin gallate (EGCG) (EGCG) 1.1g.Stir Emulsifying is mixed, then pH value is adjusted for 5.25 with 18%KOH aqueous solution.Then system homogenizing 3～5 minutes.
AVC 1.2g is continuously added under agitation.
After addition is finished, it is stirred until homogeneous.
Embodiment two：
(the double palmitamide MEA of hydroxypropyl, corresponding in figure compounds of structure I, R to weigh plan ceramide PC-1041、R2All For 15 carbon straight chained alkyls) 100g, under atmosphere of inert gases, in the reactor heating and melting (jacket temperature is 90 DEG C).
It is subsequently adding cholesterol 19.2g, stearic acid 7.3g, Palmic acid 7.0g, paeonol 5.0g, emulsifying agent SIMULSOL 165 (Seppic company is formed by tristerin and PEG-100 stearate are compounding) 10g.
After heating about 2 hours, 85 degrees Celsius of purified water 200g being added, stirring, emulsifying, homogenizing, is cooled to room temperature and obtains Emulsion.Emulsion 25g, plus purified water 50g is taken, is stirred.Add glycerol 2.4g, vaseline 2.5g, squalane 2.0g, Semen Lini oil 2.0g, Radix Oenotherae erythrosepalae oil 2.0g, borage oil 2.0g, tocopherol 1.0g, ethohexadiol 0.2g, Sensiva SC50 0.1g, glycerol list Caprylate 0.7g, -20 3.0g of polysorbate, allantoin 0.2g, pyridoxin 0.2g, pantothenylol 0.1g, sodium dihydrogen phosphate 0.1g, EDETATE SODIUM 0.1g.Stirring and emulsifying, then pH value is adjusted for 5.25 with 18%KOH aqueous solution.
Then system homogenizing 3～5 minutes.AVC is continuously added under agitation 1.2g.
After addition is finished, it is stirred until homogeneous.
Embodiment three：
Plan ceramide N- palmityl hydroxyproline cetyl is weighed (corresponding in figure structure I V compound, wherein R1 For 15 carbon straight chained alkyls, R2For 16 carbon straight chained alkyls) 25g, under atmosphere of inert gases, heating and melting (chuck temperature in the reactor Spend for 90 DEG C).
It is subsequently adding cholesterol 5g, stearic acid 1.3g, Palmic acid 1.3g, paeonol 1.5g, emulsifying agent Montanov L (Seppic company is formed by C14-22 alcohol and C14-22 alkyl-glucoside are compounding) 5g.After heating 1 hour, addition 85 is Celsius Purified water 200g of degree, stirring, emulsifying, homogenizing, is cooled to room temperature and obtains emulsion.
Add glycerol 5g, (Symrise Products, are carried with race tocopherol 5g, SymRelief 0.5g by bisabolol Take that thing is compounding to be formed), peony root extractive 0.3g, linoleic acid 0.5g, ethohexadiol 0.5g, Sensiva SC50 0.2g, glycerol list Caprylate 1.8g, EDETATE SODIUM 0.3g, sodium dihydrogen phosphate 0.15g.Stirring and emulsifying, then with 18%KOH aqueous solution and 10% pyrroles Alkanone carboxylic acid for adjusting pH value is 4.95.
Then system homogenizing 3～5 minutes.2-(Acryloyloxy)ethanol/acryloyldimethyl taurine is continuously added under agitation Sodium copolymer 5.0g (Sepinov EMT10, Seppic company).After addition is finished, it is stirred until homogeneous.
Example IV：
Weigh plan ceramide myristyl alcohol palmityl serine ester (PMS, corresponding in figure structure VIII compound, its Middle R1For 15 carbon straight chained alkyls, R2For 14 carbon straight chained alkyls) 30g, under atmosphere of inert gases, heating and melting in the minisize reaction kettle (jacket temperature is 90 DEG C).
It is subsequently adding cholesterol 7g, stearic acid 0.5g, Palmic acid 0.5g, paeonol 0.3g, emulsifying agent Montanov 202 (Seppic company is formed by eicosyl, docosyl alcohol and eicosyl glucoside are compounding) 5g.After heating 0.5 hour, Add 85 degrees Celsius of purified water 300g, stirring, emulsifying, homogenizing, be cooled to room temperature and obtain emulsion.
Add glycerol 5g, tocopherol 5g, linoleic acid 3g, linolenic acid 3g, ethohexadiol 1g, Sensiva SC50 0.5g, glycerol Single caprylate 3.5g, glycyrrhizic acid dipotassium 0.6g, resveratrol 0.5g, glycyrrhetinic acid 3g, ascorbic acid -2- glucoside 3g, EDETATE SODIUM 0.5g, -20 2.0g of polysorbate.
Stirring and emulsifying, then pH value is adjusted for 5.18 with 18%KOH aqueous solution.Then system homogenizing 3～5 minutes.
2-(Acryloyloxy)ethanol/sodium acryloyldimethyl taurate copolymers 5.0g (Sepinov is continuously added under agitation EMT10, Seppic company).After addition is finished, it is stirred until homogeneous.
Embodiment five：
It (corresponding in figure structure I I, is the mixture of four compounds to weigh plan ceramide PC9s：One R of compound1For 13 carbon straight chained alkyls, R2For 16 carbon straight chained alkyls, two R1 of compound is 13 carbon straight chained alkyls, R2 is 18 carbon straight chained alkyls, chemical combination Three R1 of thing is 15 carbon straight chained alkyls, R2 is 16 carbon straight chained alkyls, and four R1 of compound is 15 carbon straight chained alkyls, R2 is 18 carbon straight chain alkane Base) 30g, under atmosphere of inert gases, in the minisize reaction kettle heating and melting (jacket temperature is 90 DEG C).
It is subsequently adding cholesterol 7g, stearic acid 0.5g, Palmic acid 0.5g, vaseline 30g, Radix Oenotherae erythrosepalae oil 20g, emulsifying agent Montanov 202 (Seppic company is formed by eicosyl, docosyl alcohol and eicosyl glucoside are compounding) 5g, pellet Skin phenol 5g.After heating 1 hour, 85 degrees Celsius of purified water 300g being added, stirring, emulsifying, homogenizing, is cooled to room temperature and obtains breast Liquid.
Add glycerol 10g, tocopherol 5g, Radix Glycyrrhizae extract 1.0g, linoleic acid 5.1g, alpha-linolenic acid 5.3g, gamma-Linolenic acid 3.5g, ethohexadiol 1g, Sensiva SC50 0.5g, Monooctamoin 3.5g, glycyrrhizic acid dipotassium 0.6g, ascorbic acid 3g, EDETATE SODIUM 0.5g.
Stirring and emulsifying, then pH value is adjusted for 5.42 with 18%KOH aqueous solution.Then system homogenizing 3～5 minutes.
2-(Acryloyloxy)ethanol/sodium acryloyldimethyl taurate copolymers 5.0g (Sepinov is continuously added under agitation EMT10, Seppic company).After addition is finished, it is stirred until homogeneous.
Embodiment six：
(Questamide H, corresponding in figure structure to weigh the double cetyl maleic amides of plan ceramide double hydroxyethyl III, R1、R2Be 16 carbon straight chained alkyls) 10g, under atmosphere of inert gases, in the reactor heating and melting (jacket temperature be ℃).
It is subsequently adding cholesterol 2g, stearic acid 0.5g, Palmic acid 0.5g, squalane 50g, Radix Oenotherae erythrosepalae oil 30g, paeonol 2g, emulsifying agent Montanov L (Seppic company is formed by C14-22 alcohol and C14-22 alkyl-glucoside are compounding) 15g.
Heating 1 hour, adds 80 degrees Celsius of purified water 400g, stirring, emulsifying, homogenizing, is cooled to room temperature and obtains emulsion.
Add glycerol 3g, tocopherol 2.5g, linoleic acid 5g, ethohexadiol 1g, Sensiva SC50 0.5g, Monooctamoin 3.5g, EDETATE SODIUM 0.5g, -20 3.2g of polysorbate, Radix Arnebiae extract 0.5g, allantoin 1.3g, nicotiamide 1g.Stirring Emulsifying, then pH value is adjusted for 5.01 with 18%KOH aqueous solution.
Then system homogenizing 3～5 minutes, are continuously added 2-(Acryloyloxy)ethanol/acryloyldimethyl taurine under agitation Sodium copolymer 5.0g (Sepinov EMT10, Seppic company).After addition is finished, it is stirred until homogeneous.
Embodiment seven：
Plan ceramide cetyl-PG hydroxyethyl palmitamide is weighed (corresponding in figure structure V, R1For 15 carbon straight chain alkane Base, R2For 16 carbon straight chained alkyls) 25g, under atmosphere of inert gases, in the reactor heating and melting (jacket temperature is 85 DEG C).
Be subsequently adding cholesterol ester stearic acid 10g, liquid paraffin 50g, emulsifying agent Montanov L (Seppic company, by C14-22 alcohol and C14-22 alkyl-glucoside are compounding to be formed) 5g, paeonol 2.5g.After heating about 2 hours, 80 degrees Celsius are added Purified water 200g, stirring, emulsifying, homogenizing, be cooled to room temperature and obtain emulsion.
Add glycerol 5g, tocopherol 2.5g, Olibanum extract 0.5g, Herba portulacae extract 0.5g, ethohexadiol 1g, ethyl hexyl Base glycerol 0.5g, Monooctamoin 3.5g, EDETATE SODIUM 0.5g.Stirring and emulsifying, then with 18%KOH aqueous solution regulation pH value be 5.13.Then system homogenizing 3-5 minute.
2-(Acryloyloxy)ethanol/sodium acryloyldimethyl taurate copolymers 5.0g (Sepinov is continuously added under agitation EMT10, Seppic company).After addition is finished, it is stirred until homogeneous.
Recruitment has erythema, pimple, is diagnosed as the women 5 of eczema, uses in sebaceous gland not active region (real containing oil formula Apply example two) described in external preparation two weeks, compare the Parameters variation before and after use.These parameters include：Water content of stratum corneum, skin Skin color, pimple quantity, prurituss degree, across transepidermal water loss.Water content of stratum corneum is measured by Delfin MoistureMeterSC.Skin Skin redness is then obtained by comparing picture.Pimple number is obtained by checking the skin of certain area to count.Prurituss then by Volunteer is felt to weigh.Measurement across transepidermal water loss (TEWL) is foundation Skin Res.Technol.2013,19 (3): 265 278, measured using Delfin VapoMeter.Test result present worth is represented with the ratio of initial value, and each parameter is averaged Value, initial value is defined as 100.The initial value of wherein prurituss is defined as 100, and slight minimizing is defined as 70, reduces and is defined as 50, hence it is evident that subtracts 20 are defined as less.
As shown in figure 1, this it appears that erythema, pimple, across transepidermal water loss minimizing from table, water content of stratum corneum increases, Volunteer feels the reduction of prurituss degree, gets a promotion across the minimizing explanation Cutaneous permeation barrier of transepidermal water loss.
Embodiments of the invention are the foregoing is only, the scope of the claims of the present invention is not thereby limited, every using this Equivalent structure or equivalent flow conversion that bright description is made, or directly or indirectly it is used in other related technology necks Domain, is included within the scope of the present invention.

Claims (10)

1. a kind of based on the preparation for external application to skin for intending ceramide and paeonol, it is characterised in that including becoming for following weight portion Point：Intend 10～100 parts of Ceramide compound, 200～900 parts of water and 1～20 part of paeonol, the plan Ceramide compound For following structure I～VIII
One or more in shown, the chemical constitution of the paeonol is IX
2. according to claim 1 based on the preparation for external application to skin for intending ceramide and paeonol, it is characterised in that described Intend the R in Ceramide compound1、R2Saturation or undersaturated alkyl for the straight or branched of carbon number 10～40, R1、 R2Identical or different.
3. according to claim 1 based on the preparation for external application to skin for intending ceramide and paeonol, it is characterised in that described Based on one or more in the composition for intending also including following weight portion in the preparation for external application to skin of ceramide and paeonol： 1～50 part of steroidal compounds, 1～50 part of fatty acid, 0.01～30 part of antiinflammatory component, 0.1～50 part of anti-oxidation function component and 2～20 parts of water phase thickener, the steroidal compounds are cholesterol, cholesterol fatty acid ester, plant sterol and plant sterol fat One or more in fat acid esters, the fatty acid is the saturation containing carbon chain lengths 8～30 or undersaturated straight or branched One or more in fatty acid, the water phase thickener be xanthan gum, AVC, third Olefin(e) acid hydroxyl ethyl ester/sodium acryloyldimethyl taurate copolymers, polypropylene acyl group dimethyltaurine sodium, acryloyldimethyl cattle One or more in sodium sulfonate/acrylamide/VP copolymer, described based on the external preparation for skin system for intending ceramide and paeonol Ethanol, ethylene glycol, Propylene Glycol, butanediol, isopropanol, pentanediol are not included in agent.
4. according to claim 1 based on the preparation for external application to skin for intending ceramide and paeonol, it is characterised in that described Also include the oils and fatss of 0～300 weight portion based on the preparation for external application to skin for intending ceramide and paeonol, the oils and fatss are animals and plants Oils and fatss, animals and plants wax, ore deposit are cured, mineral oil, alkanes, silicone oil, three ester of synthetic glycerine, fatty acid ester fatty alcohol, paraffin, wax, One or more in silicone oil, siloxanes.
5. according to claim 3 based on the preparation for external application to skin for intending ceramide and paeonol, it is characterised in that described Antiinflammatory group is divided into N- fatty acyl ethanolamine, 4- tert. butyl cyclohexanol, tea polyphenols, bisabolol, ginger-root extract, Olibanum extraction Thing, peony root extractive, glycyrrhetate, glycyrrhetinic acid, green tea extract, decoyl Glycine, Monooctamoin, zinc salt, table Nutgall catechin gallic acid ester EGCG, pyridoxol, nicotiamide, allantoin, resveratrol, N, N- (double 2- hydroxyethyls) nonyl One kind in diamides, Radix Arnebiae extract, Herba portulacae extract, Aloe extract, camomile extract and Semen Vitis viniferae extract Or it is multiple.
6. according to claim 3 based on the preparation for external application to skin for intending ceramide and paeonol, it is characterised in that described Anti-oxidation function component is tocopherol, tocopherol acetate, tocopherol propionic ester, tocopherol fatty acid ester, tocopherol phosphate Sodium, ascorbic acid, L-AA -2- glucoside, 2-O- ethylascorbyl, 3-O- ethylascorbyl, aminopropanol resist Bad hematic acid phosphate ester, Vitamin C dipalmitate, magnesium L-ascorbyl-2-phosphate, NAP, ascorbic acid four Different cetylate, resveratrol, beta-carotene, Ubidecarenone, Ai Diben, astaxanthin, alpha-lipoic acid, soybean isoflavone, Semen Ginkgo One or more in flavone and glutathion.
7. according to claim 1 based on the preparation for external application to skin for intending ceramide and paeonol, it is characterised in that described PH value based on the preparation for external application to skin for intending ceramide and paeonol is 4.5～5.5, using 2-pyrrolidone-5-carboxylic acid's aqueous solution or Person KOH aqueous solution adjusts pH value.
8. according to claim 1 based on the preparation for external application to skin for intending ceramide and paeonol, it is characterised in that described Also include the emulsifying agent of 1～50 weight portion based on the preparation for external application to skin for intending ceramide and paeonol, the emulsifying agent is department One or more in disk-TWEEN Series, alkyl polyglucoside-fatty alcohol series, glyceryl monostearate/PEG100 stearate.
9. according to claim 1 based on the preparation for external application to skin for intending ceramide and paeonol, it is characterised in that described Also include the preservative of 1～20 weight portion based on the preparation for external application to skin for intending ceramide and paeonol, the preservative is for oneself One or more in glycol, ethohexadiol, Sensiva SC50, Monooctamoin, chlorphenesin.
10. the arbitrary described producer based on the preparation for external application to skin for intending ceramide and paeonol of a kind of claim 1～9 Method, it is characterised in that comprise the following steps for：
Reactor is placed under atmosphere of inert gases, jacket temperature is set to 80～95 degrees Celsius, Ceramide compound will be intended Heating and melting, adds steroidal compounds, satisfied fatty acid, paeonol, oils and fatss, emulsifying agent, after stirring 0.5～10 hour, plus Enter 80～90 DEG C of water, stirring and emulsifying, homogenizing, obtain emulsion；
Treat that emulsion is cooled to room temperature, add water, toward emulsion in addition unsaturated fatty acid, antiinflammatory component, anti-oxidation function component, And preservative, stirring, homogenizing, then with 2-pyrrolidone-5-carboxylic acid's aqueous solution that mass percent is 10% or mass percent it is 18% KOH aqueous solution adjusts pH value to 4.5～5.5, and homogenizing is eventually adding water phase thickener, is uniformly mixing to obtain based on plan Ceramide and the preparation for external application to skin of paeonol.
CN201610843009.8A 2016-09-23 2016-09-23 Skin external-applying preparation based on quasi-ceramide and paeonol and production method thereof Pending CN106420605A (en)

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CN108078848A (en) * 2017-12-29 2018-05-29 广州市科能化妆品科研有限公司 A kind of novel sunscreen synergistic composition
JP7166063B2 (en) 2018-02-28 2022-11-07 株式会社コーセー Cosmetics and external skin preparations
JP7168330B2 (en) 2018-02-28 2022-11-09 株式会社コーセー Cosmetics and external skin preparations
KR20210076845A (en) * 2019-12-16 2021-06-24 주식회사 젠트리바이오 Pharmaceutical composition for external application comprising paeonol, panthenol, or a pharmaceutically acceptable salt thereof as an active ingredient
KR102328178B1 (en) 2019-12-16 2021-11-18 주식회사 젠트리바이오 Pharmaceutical composition for external application comprising paeonol, panthenol, or a pharmaceutically acceptable salt thereof as an active ingredient
KR20210141909A (en) * 2019-12-16 2021-11-23 주식회사 젠트리바이오 Pharmaceutical composition for external application comprising paeonol, panthenol, or a pharmaceutically acceptable salt thereof as an active ingredient
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KR102474935B1 (en) 2019-12-16 2022-12-07 주식회사 젠트리바이오 Pharmaceutical composition comprising paeonol, panthenol, or a pharmaceutically acceptable salt thereof as an active ingredient
CN113082029A (en) * 2021-03-02 2021-07-09 浙大宁波理工学院 Wound cleaning disinfectant
CN117598915A (en) * 2023-07-19 2024-02-27 诺德溯源(广州)生物科技有限公司 Permeation promotion inclusion of 4-tert-butylcyclohexanol and preparation method and application thereof
CN117598915B (en) * 2023-07-19 2024-08-02 诺德溯源(广州)生物科技有限公司 Permeation promotion inclusion of 4-tert-butylcyclohexanol and preparation method and application thereof

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