CN104414871A - Cosmetic composition and application thereof - Google Patents
Cosmetic composition and application thereof Download PDFInfo
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- CN104414871A CN104414871A CN201310381621.4A CN201310381621A CN104414871A CN 104414871 A CN104414871 A CN 104414871A CN 201310381621 A CN201310381621 A CN 201310381621A CN 104414871 A CN104414871 A CN 104414871A
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Abstract
The invention discloses a cosmetic composition. The cosmetic composition comprises a compound and/or a pharmaceutically acceptable salt, wherein the compound has a formula 1 as shown in the specification, and R is a substituted or unsubstituted aryl group with 4-20 carbon atoms. The cosmetic composition disclosed by the invention has the efficacies of moisturizing, whitening and brightening skin, and the active components of the cosmetic composition can penetrate into the skin easily and have good light and heat stability.
Description
Technical field
The present invention relates to a kind of cosmetic composition and application thereof.
Background technology
Vitamin B6 (Vitamin B6) is also known as pyridoxin, a kind of containing pyridoxol (pyridoxine, PN), the vitamin B group of 2-methyl-3-hydroxy-4-formyl-5-hydroxymethylpyridine. (pyridoxal, PL), pyridoxamine (pyridoxamine, PM) and their phosphoric acid derivatives (PNP, PLP, PMP).Vitamin B6 is clear crystal, soluble in water and ethanol, stable in acid solution, destructible in alkali liquor, and pyridoxol is heat-resisting, 2-methyl-3-hydroxy-4-formyl-5-hydroxymethylpyridine. and the thermo-labile temperature of pyridoxamine, meets light and easily decomposes destruction.Vitamin B6 content in yeast, liver, grain, meat, fish, egg, beans and Semen arachidis hypogaeae is more.Vitamin B6 is the constituent of some coenzyme in human body, participates in multiple metabolic response, especially has substantial connection with amino acid metabolism.
Pyridoxol Chang Zuowei prevents and treats the active component of the preparation of pachylosis, acne, Exposure to Sunlight chloasma hepaticum, seborrheic alopecia, scytitis, general acne etc.But, because pyridoxol is difficult to while maintenance photo and thermal stability, has both water solublity and fat-soluble, limit its application as the component of cosmetics.
Therefore, need badly and find a kind of containing having photo and thermal stability, have both the cosmetic composition of water solublity and fat-soluble pyridoxol cycli phosphate derivant, this cosmetic composition to skin moisture-keeping, brighten and strengthen gloss and have better effects.
Summary of the invention
The object of this invention is to provide a kind of cosmetic composition, this cosmetic composition can overcome for skin moisture-keeping, the problem that active component is poor to Cutaneous permeation, photo and thermal stability is poor brightening and strengthen gloss.
The invention provides a kind of cosmetic composition, this cosmetic composition contains compound shown in following formula 1 and/or its pharmaceutically acceptable salt,
Wherein, the substituted or unsubstituted aryl of R to be carbon number be 4-20.
Present invention also offers a kind of cosmetic composition, described cosmetic composition is emulsion, emulsifiable paste, skin cream, essence, facial film, lip pomade, foundation cream, beautifying liquid, soap, shampoo, hair conditioner or bath gel.
Present invention also offers a kind of cosmetic composition at skin moisture-keeping, brighten and strengthen the application in gloss.
Cosmetic composition of the present invention to skin moisture-keeping, brighten and strengthen gloss and have better effects, and active component is easy to good to Cutaneous permeation, photo and thermal stability.
Other features and advantages of the present invention are described in detail in detailed description of the invention part subsequently.
Detailed description of the invention
Below the specific embodiment of the present invention is described in detail.Should be understood that, detailed description of the invention described herein, only for instruction and explanation of the present invention, is not limited to the present invention.
The invention provides a kind of cosmetic composition, this cosmetic composition contains compound shown in following formula 1 and/or its pharmaceutically acceptable salt, wherein, and the substituted or unsubstituted aryl of R to be carbon number be 4-20.
In the present invention; described aryl can be phenyl, xenyl, thienyl, furyl, pyridine radicals, naphthyl, single benzofuranyl or two benzofuranyl, at least one in acyl group, cyano group, nitro, three halomethyl, phenyl, furyl and thienyl that the alkoxyl that the alkyl that the substituent group on described aryl can be selected from halogen, carbon number is 1-4, carbon number are 1-4, carbon number are 1-4.Described halogen can be fluorine, chlorine, bromine or iodine.Carbon number is the alkyl of 1-4 can be methyl, ethyl, n-pro-pyl, isopropyl, normal-butyl, isobutyl group or the tert-butyl group.Described carbon number is the alkoxyl of 1-4 can be methoxyl group, ethyoxyl, positive propoxy, isopropoxy, n-butoxy, isobutoxy or tert-butoxy.Carbon number is the acyl group of 1-4 can be formoxyl, acetyl group, positive propiono, iso-propionyl, positive bytyry, isobutyryl or tertiary bytyry.Three halomethyl can be trichloromethyl, trisbromomethyl or trifluoromethyl.
In the present invention, substituent group quantity can be 1-5, is preferably 1-2.
In the present invention, described aryl is preferably aryl is phenyl, 4-fluorophenyl, 3-chlorphenyl, 4-methoxyphenyl, 3-pyridine radicals or 2-furyl.
In the present invention, there is no particular limitation for the preparation method of compound shown in formula 1, can comprise as the preferred method of one, under substitution reaction condition, contacted by compound shown in compound shown in formula 2 with formula 3 and/or formula 3 ',
Wherein, Hal can be halogen, and such as, fluorine, chlorine, bromine or iodine, R can be the substituted or unsubstituted aryl of 4-20 for carbon number.
Described aryl can be phenyl, xenyl, thienyl, furyl, pyridine radicals, naphthyl, single benzofuranyl or two benzofuranyl, at least one in acyl group, cyano group, nitro, three halomethyl, phenyl, furyl and thienyl that the alkoxyl that the alkyl that the substituent group on described aryl can be selected from halogen, carbon number is 1-4, carbon number are 1-4, carbon number are 1-4.Described halogen can be fluorine, chlorine, bromine or iodine.Carbon number is the alkyl of 1-4 can be methyl, ethyl, n-pro-pyl, isopropyl, normal-butyl, isobutyl group or the tert-butyl group.Described carbon number is the alkoxyl of 1-4 can be methoxyl group, ethyoxyl, positive propoxy, isopropoxy, n-butoxy, isobutoxy or tert-butoxy.Carbon number is the acyl group of 1-4 can be formoxyl, acetyl group, positive propiono, iso-propionyl, positive bytyry, isobutyryl or tertiary bytyry.Three halomethyl can be trichloromethyl, trisbromomethyl or trifluoromethyl.
Substituent group quantity can be 1-5, is preferably 1-2.There is no particular limitation for the position of substitution.
It is phenyl, 4-fluorophenyl, 3-chlorphenyl, 4-methoxyphenyl, 3-pyridine radicals or 2-furyl that described aryl is preferably aryl.
Relative to the consumption of compound shown in described formula 2, the consumption of described formula 3 and/or the shown compound of formula 3 ' can be 10-1000 % by mole, is preferably 50-500 % by mole.
In described substitution reaction, described alkaline matter can be various conventional alkaline material, such as, at least one in alkali metal hydroxide, alkaline earth metal hydroxide, alkali carbonate, alkaline earth metal carbonate, alkali metal hydrogencarbonate, alkali metal acetate, Alkaline Earth Metal Acetate, alkali metal alcoholates or alkaline-earth alkoxides, be preferably at least one in alkali metal hydroxide or alkali metal hydrogencarbonate, at least one more preferably in sodium bicarbonate, sodium hydroxide, potassium hydroxide and potassium bicarbonate, is more preferably sodium hydroxide.
The consumption of described alkaline matter is not particularly limited, and is preferred the pH value of reaction system to be adjusted to 9-10.
In described substitution reaction, described solvent can be at least one in water and various conventional organic solvent, as organic solvent, can enumerate, toluene, dimethylbenzene, benzene, the hydrocarbon system solvents such as hexane, chloroform, dichloromethane, dichloroethanes, chlorobenzene, the chlorinated hydrocarbon solvents such as dichloro-benzenes, glycol dimethyl ether, diethyl ether, cyclohexyl methyl ether, butyl oxide, dimethoxy-ethane, 1, 4-dioxane, the ether series solvents such as oxolane, ethyl acetate, the ester series solvents such as butyl acetate, 2-butanone, the ketone series solvents such as methylisobutylketone, methanol, ethanol, 2-propanol, the alcohol series solvents such as butanols, acetonitrile, isopropyl cyanide, valeronitrile, the nitrile series solvents such as benzonitrile, dioxolane, gamma-butyrolacton, 6-caprolactone, ethylene carbonate, Allyl carbonate, diethyl carbonate, dimethyl sulfoxide, dimethyl formamide, N-methyl 2-Pyrrolidone etc.Above-mentioned solvent can separately and water form mixed solvent, also can multiple while form mixed solvent with water.Preferred substitution reaction solvent is at least one in water and dichloromethane, is more preferably water.
The consumption of described solvent is not particularly limited, and such as, relative to the consumption of compound shown in formula 2, the consumption of described solvent can be 5-20 % by mole.
The condition of described substitution reaction comprises: reaction temperature can be 15-30 DEG C, and the response time can be 2-10 hour, and preferably, reaction temperature is 20-25 DEG C, and the response time is 4-8 hour.
There is no particular limitation for the addition sequence of each reactant and alkaline matter and mode, can be order and the mode of this area routine.Such as, directly first each reactant can be dropped in solvent and mix, then drop into alkaline matter adjusted to ph.
Above-mentioned preparation method can complete in the synthesis device of various this areas routine, such as, the there-necked flask of agitator and thermometer is housed.
The method can also comprise, after reaction terminates, separate out compound shown in formula 1 by adding acidic materials.The consumption of described acidic materials is not particularly limited, and is preferred the pH value of reaction system to be adjusted to 5-6.
Described acidic materials can be various conventional acid material, such as, sulphuric acid, nitric acid, perchloric acid, hydrochloric acid, hydrobromic acid, hydroiodic acid, the acid of hydrogen astatine, hydrogen telluric acid, hyperbromic acid, hydrogen folds iodic acid, metaperiodic acid, chloric acid, bromic acid, hexafluosilicic acid, chlorine plumbic acid, Metaphosphoric acid, osmic acid, permanganic acid, selenic acid, ferric acid, hydrogen borate, fluosulfonic acid, the mineral acid such as cyanic acid and Hydrogen thiocyanate, 2, 4, 6-trinitrophenol, 2, 4, 6-trinitrobenzoic acid, trifluoroacetic acid, trichloroacetic acid, methanesulfonic acid, benzenesulfonic acid, ring ethyl mercaptan sulfonic acid, ethanedioic acid, 2-chlorine ethyl mercaptan, formic acid, the organic acid such as acetic acid and p-methyl benzenesulfonic acid.Above-mentioned acidic materials can be used alone and also can be used in combination.
The method can also comprise, and purifies to the product containing compound shown in formula 1.The method of described purification is useless to be particularly limited to, and can be the method for purification of the various routine in this area, such as Filtration, washing method etc.
In the present invention, relative to the gross weight of described cosmetic composition, the content of compound and/or its pharmaceutically acceptable salt shown in described formula 1 can be 0.1-10 % by weight, is preferably 0.5-50 % by weight.
The application mode of cosmetic composition of the present invention is not particularly limited.Such as, can apply as emulsion, emulsifiable paste, skin cream, essence, facial film, lip pomade, foundation cream, beautifying liquid, soap, shampoo, hair conditioner or bath gel.
In addition, in the scope not destroying effect of the present invention, cosmetic composition of the present invention suitably can also contain composition known up to now, such as: surfactant, as sorbitan fatty acid esters, polyglyceryl fatty acid ester, sucrose fatty acid ester and polyoxyethylene alkyl ether; Hydrocarbon, as squalane, liquid paraffin and paraffin; Fatty acid ester, as isopropyl palmitate and butyl stearate; Silicone oil, as simethicone and Cyclomethicone; Oiliness improver, as Cera Flava, olive oil and sunflower oil; Polyhydric alcohol, as glycerol, propylene glycol and butanediol; Stabilizing agent, as sodium chloride and magnesium sulfate; Vitamin, as vitamin A, vitamin B complex, vitamin C and vitamin E; Antiseptic, as potassium sorbate; Antiinflammatory, as aminoacid, glycyrrhetate and glycyrrhetin hydrochlorate; Organic uv absorbers, such as, para-amino benzoic acid class organic uv absorbers (as ESCAROL 507), cinnamic acid organic uv absorbers (as octyl methoxycinnamate), benzophenone organic uv absorbers (as oxo benzophenone), and salicylic acid organic uv absorbers; Spice; Dyestuff; Pigment; Antioxidant; Convergence medicine and cell activator etc.Mentioned component can a kind ofly add separately, also can add by multiple combination.
There is no particular limitation for the addition of mentioned component, can adjust arbitrarily as required.
Cosmetic composition of the present invention can also contain water, such as, and deionized water or distilled water.There is no particular limitation for the consumption of water.
Especially, the cosmetic composition as the application such as emulsion and emulsifiable paste can also add carboxy vinyl polymer as hydrophilic thickeners or emulsion stabilizer.When being added in cosmetics by carboxy vinyl polymer, relative to the gross mass of cosmetic composition, the addition of carboxy vinyl polymer can be 0.01-5 quality %, is preferably 0.1-3 quality %.When the addition of carboxy vinyl polymer is less than 0.01 quality %, cosmetic composition can not become sufficient gel state in some cases.On the contrary, when the addition of carboxy vinyl polymer is greater than 5 quality %, the viscosity of cosmetic composition can exceed required viscosity.
Below will be described the present invention by embodiment.
In following examples, NMR spectrogram is measured by BRUKER AVANCE400MHz NMR spectrometer with superconducting magnet, and wherein, deuterated reagent is deuterated dimethyl sulfoxide (DMSO-d6), and hydrogen spectrum is interior mark with tetramethylsilane; Mass spectrum is by Thermo Qusest mass spectrograph mass spectrograph; PH value is recorded by prunus mume (sieb.) sieb.et zucc. Teller FE20 type pH value analyzer.Compound shown in formula 2 to be refined company limited purchased from Jiangsu Ai Ke.
Preparation example 1
By compound shown in 0.01mol formula 2,0.05mol Benzenecarbonyl chloride. added in 18g water and mixes, then adds sodium hydroxide adjust ph to 9,25 DEG C of stirring reactions 7 hours, by concentrated hydrochloric acid adjust ph to 6, obtain the product containing solid, filter to obtain crude product, add the ethanol 10g reflux 15 minutes that concentration is 95%, be cooled to stirring at room temperature 2 hours, filter, then use water and washing with alcohol successively, after drying, obtain off-white color crystalline powder product 0.006mol.Carry out nuclear magnetic resonance, NMR and mass spectral analysis to this product, result is as follows:
1H NMR(DMSO-d6)δ2.48(s，3H)，5.40(s，2H)，5.42(d，2H)，7.55(m，2H)，7.69(m，1H)，7.97(d，2H)，8.41(s，1H)；
MS(ESI)：m/e=336(M+1)。
Can be proved by above-mentioned analysis result, gained off-white color crystalline powder is pyridoxol-3,4 '-cycli phosphate-5-benzoate.
Preparation example 2
By compound shown in 0.01mol formula 2,0.03mol added in 18g water fluorobenzoyl chloride and mixes, then adds sodium hydroxide adjust ph to 10,20 DEG C of stirring reactions 8 hours, by concentrated sulphuric acid adjust ph to 5.5, obtain the product containing solid, filter to obtain crude product, add the ethanol 10g reflux 15 minutes that concentration is 95%, be cooled to stirring at room temperature 2 hours, filter, then use water and washing with alcohol successively, after drying, obtain off-white color crystalline powder product 0.005mol.Carry out nuclear magnetic resonance, NMR and mass spectral analysis to this product, result is as follows:
1H NMR(DMSO-d6)δ2.48(s，3H)，5.40(s，2H)，5.42(d，2H)，7.36(t，2H)，8.04(dd，2H)，8.43(s，1H)；
MS(ESI)：m/e=354(M+1)。
Can be proved by above-mentioned analysis result, gained off-white color crystalline powder is pyridoxol-3,4 '-cycli phosphate-5-parafluorobenzoic acid ester.
Preparation example 3
By compound shown in 0.01mol formula 2,0.006mol m-chlorobenzoyl chloride added in 18g water and mixes, then adds sodium hydroxide adjust ph to 9.5,22 DEG C of stirring reactions 4 hours, by concentrated hydrochloric acid adjust ph to 6, obtain the product containing solid, filter to obtain crude product, add the ethanol 10g reflux 15 minutes that concentration is 95%, be cooled to stirring at room temperature 2 hours, filter, then use water and washing with alcohol successively, after drying, obtain off-white color crystalline powder product 0.003mol.Carry out nuclear magnetic resonance, NMR and mass spectral analysis to this product, result is as follows:
1H NMR(DMSO-d6)δ2.46(s，3H)，5.36(d，2H)，5.41(s，2H)，7.59(t，1H)，7.78(m，1H)，7.93(m，2H)，8.36(s，1H)；
MS(ESI)：m/e=370(M+1)。
Can be proved by above-mentioned analysis result, gained off-white color crystalline powder is pyridoxol-3,4 '-cycli phosphate-5-m-chlorobenzoic acid ester.
Preparation example 4
By compound shown in 0.01mol formula 2,0.04mol anisoyl chloride added in 84g dichloromethane and mixes, then adds sodium hydroxide adjust ph to 9.5,24 DEG C of stirring reactions 4 hours, by concentrated hydrochloric acid adjust ph to 5, obtain the product containing solid, filter to obtain crude product, add the ethanol 10g reflux 15 minutes that concentration is 95%, be cooled to stirring at room temperature 2 hours, filter, then use water and washing with alcohol successively, after drying, obtain off-white color crystalline powder product 0.006mol.Carry out nuclear magnetic resonance, NMR and mass spectral analysis to this product, result is as follows:
1H NMR(DMSO-d6)δ2.48(s，3H)，4.89(s，3H)，5.40(s，2H)，5.42(d，2H)，7.16(t，2H)，7.95(dd，2H)，8.43(s，1H)；
MS(ESI)：m/e=366(M+1)。
Can be proved by above-mentioned analysis result, gained off-white color crystalline powder is pyridoxol-3,4 '-cycli phosphate-5-p-Methoxybenzoic acid ester.
Preparation example 5
By compound shown in 0.01mol formula 2,0.04mol nicotinoyl chlorine added in 9g water and mixes, then adds sodium hydroxide adjust ph to 9.5,24 DEG C of stirring reactions 4 hours, by concentrated hydrochloric acid adjust ph to 5, obtain the product containing solid, filter to obtain crude product, add the ethanol 10g reflux 15 minutes that concentration is 95%, be cooled to stirring at room temperature 2 hours, filter, then use water and washing with alcohol successively, after drying, obtain off-white color crystalline powder product 0.005mol.Carry out nuclear magnetic resonance, NMR and mass spectral analysis to this product, result is as follows:
1H NMR(DMSO-d6)δ2.49(s，3H)，5.40(d，2H)，5.44(s，2H)，7.60(dd，1H)，8.34(m，1H)，8.41(s，1H)，8.82(m，1H)，9.10(d，1H)；
MS(ESI)：m/e=337(M+1).
Can be proved by above-mentioned analysis result, gained off-white color crystalline powder is pyridoxol-3,4 '-cycli phosphate-5-nicotinate.
Preparation example 6
By compound shown in 0.01mol formula 2,0.1mol furoyl chloride added in 18g water and mixes, then adds sodium hydroxide adjust ph to 9,25 DEG C of stirring reactions 6 hours, by concentrated hydrochloric acid adjust ph to 5.5, obtain the product containing solid, filter to obtain crude product, add the ethanol 10g reflux 15 minutes that concentration is 95%, be cooled to stirring at room temperature 2 hours, filter, then use water and washing with alcohol successively, after drying, obtain off-white color crystalline powder product 0.004mol.Carry out nuclear magnetic resonance, NMR and mass spectral analysis to this product, result is as follows:
1H NMR(DMSO-d6)δ2.47(s，3H)，5.37(d，2H)，5.39(s，2H)，6.73(m，1H)，7.40(m，1H)，8.02(m，1H)，8.37(s，1H)；
MS(ESI)：m/e=326(M+1)。
Can be proved by above-mentioned analysis result, gained off-white color crystalline powder is pyridoxol-3,4 '-cycli phosphate-5-furoate.
Test case 1
The compound obtained in above-described embodiment solubility experiment result in 25 DEG C of water is as shown in table 2.Not molten thing oven dry by the 25 DEG C of stirrings in 100ml water of 1g material being filtered after 1 hour, then calculates through Subtraction method and obtains by dissolubility.
Table 1
| Dissolubility | |
| Vitamin B6 | 10% |
| Compound shown in formula 2 | 11% |
| Embodiment 1 | 2% |
| Embodiment 2 | 1% |
| Embodiment 3 | 4% |
| Embodiment 4 | 4% |
| Embodiment 5 | 2% |
| Embodiment 6 | 3% |
Test case 2
CLogP parameter and the LogP parameter of the compound obtained in above-described embodiment are as shown in table 1.LogP parameter refers to the logarithm value of the partition coefficient of something in normal octane (oil) and water, and CLogP parameter is the value of calculation of this logarithm value.LogP parameter value is larger, and fat-soluble better, less water solublity is better.Logp records according to regulation on pharmaceutics book, is dissolved in the n-octyl alcohol/aqueous medium of different proportion by above-claimed cpd, and shaking table jolting 24h, to balance, then surveys two Xiangli above-claimed cpd concentration, draws LogP(buffer solution pH=7.4).CLogp is obtained by ChemDraw Ultra8.0 computed in software.
Table 2
| CLogP | LogP | |
| Vitamin B6 | -0.80 | -0.14 |
| Compound shown in formula 2 | -3.12 | 0.74 |
[0084]
| Embodiment 1 | -0.28 | 2.78 |
| Embodiment 2 | -0.14 | 2.92 |
| Embodiment 3 | 0.43 | 3.31 |
| Embodiment 4 | -0.11 | 2.53 |
| Embodiment 5 | -1.63 | 1.47 |
| Embodiment 6 | -1.11 | 1.26 |
Can be found out by table 1 and 2, the pyridoxol cycli phosphate derivant that cosmetic composition of the present invention contains has both water solublity and fat-soluble, that is, this pyridoxol cycli phosphate derivant had both been suitable as the active component of aqueous cosmetics composition, effectively can permeate again to skin.
Test case 3
The illumination experiment result of the compound obtained in above-described embodiment 1,5 and 6 is respectively as shown in table 3,4 and 5.Sample thief compound, is placed in transparent tool plug weighing botle, irradiates under light intensity 4500Lx, and after often kind of compound places 1,5,10 day respectively, sampling is observed, test.Wherein, fusing point is recorded by SGW X-4B micro-meldometer; Solution color to be contrasted with reference colour color comparison tube with strength solution by preparation and records; PH value is recorded by prunus mume (sieb.) sieb.et zucc. Teller FE20 type pH value analyzer; Content is recorded by Shimazu LC-20AT type high performance liquid chromatograph.1 day weightless (wt%)=(raw sample weight is example weight after-1 day)/raw sample weight × 100%, example weight × 100% of 5 days weightless (wt%)=(after 1 day example weight after-5 days example weight)/after 1 day, example weight × 100% of 10 days weightless (wt%)=(after 5 days example weight after-10 days example weight)/after 5 days.
Table 3
| 1 day | 5 days | 10 days | |
| Outward appearance | Off-white color crystalline powder | Off-white color crystalline powder | Off-white color crystalline powder |
| Fusing point (DEG C) | 180.0-182.5 | 180.0-181.8 | 179.5-180.0 |
[0090]
| Solution color | Be better than Y 7 | Be better than Y 7 | Be better than Y 7 |
| Clarity | Clarification | Clarification | Clarification |
| Acidity (pH) | 3.40 | 3.43 | 3.44 |
| Weightless (wt%) | 0.03 | 0 | 0 |
| Content (wt%) | 99.8 | 99.5 | 99.3 |
Table 4
| 1 day | 5 days | 10 days | |
| Outward appearance | Off-white color crystalline powder | Off-white color crystalline powder | Off-white color crystalline powder |
| Fusing point (DEG C) | 137.0-143.4 | 137.4-143.0 | 137.2-143.0 |
| Solution color | Be better than Y 7 | Be better than Y 7 | Be better than Y 7 |
| Clarity | Clarification | Clarification | Clarification |
| Acidity (pH) | 3.40 | 3.43 | 3.44 |
| Weightless (wt%) | 0.03 | 0 | 0 |
| Content (wt%) | 99.8 | 99.4 | 99.4 |
Table 5
| 1 day | 5 days | 10 days | |
| Outward appearance | Off-white color crystalline powder | Off-white color crystalline powder | Off-white color crystalline powder |
| Fusing point (DEG C) | 137.0-143.4 | 137.4-143.0 | 137.2-143.0 |
| Solution color | Be better than Y 7 | Be better than Y 7 | Be better than Y 7 |
| Clarity | Clarification | Clarification | Clarification |
| Acidity (pH) | 3.40 | 3.43 | 3.44 |
| Weightless (wt%) | 0.03 | 0 | 0 |
[0095]
| Content (wt%) | 99.8 | 99.4 | 99.4 |
Test case 4
The Heating Experiment result of the compound obtained in above-described embodiment 1,5 and 6 is as shown in table 6,7 and 8.Sample thief compound, puts in transparent tool plug weighing botle, heats in 60 DEG C of Constant Temp. Ovens, and after often kind of compound places 1,5,10 day respectively, sampling is observed, test.Wherein, fusing point is recorded by SGW X-4B micro-meldometer; Solution color to be contrasted with reference colour color comparison tube with strength solution by preparation and records; PH value is recorded by prunus mume (sieb.) sieb.et zucc. Teller FE20 type pH value analyzer; Content is recorded by Shimazu LC-20AT type high performance liquid chromatograph.1 day weightless (wt%)=(raw sample weight is example weight after-1 day)/raw sample weight × 100%, example weight × 100% of 5 days weightless (wt%)=(after 1 day example weight after-5 days example weight)/after 1 day, example weight × 100% of 10 days weightless (wt%)=(after 5 days example weight after-10 days example weight)/after 5 days.
Table 6
| 1 day | 5 days | 10 days | |
| Outward appearance | Off-white color crystalline powder | Off-white color crystalline powder | Off-white color crystalline powder |
| Fusing point (DEG C) | 180.0-182.5 | 180.0-181.8 | 179.5-180.0 |
| Solution color | Be better than Y 7 | Be better than Y 7 | Be better than Y 7 |
| Clarity | Clarification | Clarification | Clarification |
| Acidity (pH) | 3.40 | 3.43 | 3.44 |
| Weightless (wt%) | 0.03 | 0 | 0 |
| Content (wt%) | 99.8 | 99.5 | 99.4 |
Table 7
| 1 day | 5 days | 10 days | |
| Outward appearance | Off-white color crystalline powder | Off-white color crystalline powder | Off-white color crystalline powder |
| Fusing point (DEG C) | 137.0-143.4 | 137.2-143.1 | 137.2-143.0 |
| Solution color | Be better than Y 7 | Be better than Y 7 | Be better than Y 7 |
| Clarity | Clarification | Clarification | Clarification |
| Acidity (pH) | 3.40 | 3.43 | 3.44 |
| Weightless (wt%) | 0 | 0.07 | 0.06 |
| Content (wt%) | 99.8 | 99.5 | 99.3 |
Table 8
| 1 day | 5 days | 10 days | |
| Outward appearance | Off-white color crystalline powder | Off-white color crystalline powder | Off-white color crystalline powder |
| Fusing point (DEG C) | 137.0-143.4 | 137.2-143.1 | 137.2-143.0 |
| Solution color | Be better than Y 7 | Be better than Y 7 | Be better than Y 7 |
| Clarity | Clarification | Clarification | Clarification |
| Acidity (pH) | 3.40 | 3.43 | 3.44 |
| Weightless (wt%) | 0 | 0.07 | 0.06 |
| Content (wt%) | 99.8 | 99.5 | 99.3 |
Can be found out by table 3-8, the pyridoxol cycli phosphate derivant photo and thermal stability that cosmetic composition of the present invention contains is good, that is, this pyridoxol cycli phosphate derivant, as the active component of cosmetic composition, can be preserved or use under Gao Regao illumination condition.
Embodiment 1
Relative to the gross weight of cosmetic composition, pyridoxol cycli phosphate derivant is the pyridoxol-3 obtained by preparation example 5,4 '-cycli phosphate-5-nicotinate, consumption is 2 % by weight, and the consumption of single oleic acid sorbitan ester is 1.5 % by weight, the consumption of simethicone is 0.4 % by weight, the consumption of butyl stearate is 20 % by weight, and the consumption of potassium sorbate is 0.1 % by weight, and the consumption of propylene glycol is 10 % by weight, the consumption of vitamin B3 is 0.5 % by weight, and the consumption of deionized water is 65.5 % by weight.After being uniformly mixed, cosmetic composition is obtained in beaker.
The compositions prepared is for testing the enhancing skin moisture-keeping of 12 volunteer's compositions for the same colour of skin, brightening and strengthen the effect of gloss.Record the initial colour of skin, by experienced pharmacists, above-mentioned composition is applied to the volar forearm (using clear water wash clean in advance) of experimenter in preassigned position.Each administration interval 3 hours, every day, each position used 3 times, used clear water wash clean after in the end having used compositions.Continuous administration one week, the change of the record colour of skin.By compare with compositions position and around it difference of the colour of skin carry out estimating classification with the change of evaluate color.Test instrunment: Mexameter MX18(CK Electronic GmbH, Germany).Mexameter MX18 is a multifunctional testing platform of German CK company skinanalysis apparatus, and main frame self, containing the connecting hole of an oils and fats test probe and eight skin tests probe, can connect maximum eight identical or different skin test probes.Often kind of probe all has different analysis software and display window.The probe connected comprises: Corneometer CM825(moisture content test probe), Sebumeter SM815(oil content test probe), Skin-pH-Meter PH905(acid-base value test probe), Mexameter MX18(melanin and haemachrome test probe)--refer to mottle content and scytitis reaction, Tewameter TM300(water loss test probe TEWL), Reviscometer RVM600(elastic fibrous tissue test probe) and Temperature & Rel.Air humidity(environment temperature and humidity test probe).Effect negative value represents the effect having skin moisture-keeping, brighten and strengthen gloss.Result is as shown in table 9.
Embodiment 2
According to preparing with the same method of embodiment 1 and testing cosmetic composition, be the pyridoxol-3 obtained by preparation example 4 unlike pyridoxol cycli phosphate derivant, 4 '-cycli phosphate-5-p-Methoxybenzoic acid ester, consumption is 4 % by weight, and the consumption of deionized water is 63.5 % by weight.Result is as shown in table 9.
Embodiment 3
According to preparing with the same method of embodiment 1 and testing cosmetic composition, be the pyridoxol-3 obtained by preparation example 6 unlike pyridoxol cycli phosphate derivant, 4 '-cycli phosphate-5-thiophene-2-carboxylic acid ester, consumption is 1 % by weight, and the consumption of deionized water is 66.5 % by weight.Result is as shown in table 9.
Comparative example 1
According to preparing with the same method of embodiment 1 and testing cosmetic composition, unlike not containing pyridoxol cycli phosphate derivant.Result is as shown in table 9.
Table 9
| Skin moisture-keeping, brighten and strengthen the meansigma methods of luster effect | |
| Embodiment 1 | -0.21 |
| Embodiment 2 | -0.15 |
| Embodiment 3 | -0.1 |
| Comparative example 1 | 0 |
Can be found out by table 9, cosmetic composition of the present invention to skin moisture-keeping, brighten and strengthen gloss and have better effects.
In sum, cosmetic composition of the present invention to skin moisture-keeping, brighten and strengthen gloss and have better effects, and active component is easy to good to Cutaneous permeation, photo and thermal stability.
More than describe the preferred embodiment of the present invention in detail; but the present invention is not limited to the detail in above-mentioned embodiment, within the scope of technical conceive of the present invention; can carry out multiple simple variant to technical scheme of the present invention, these simple variant all belong to protection scope of the present invention.
It should be noted that in addition, each concrete technical characteristic described in above-mentioned detailed description of the invention, in reconcilable situation, can be combined by any suitable mode, in order to avoid unnecessary repetition, the present invention illustrates no longer separately to various possible compound mode.
In addition, also can carry out combination in any between various different embodiment of the present invention, as long as it is without prejudice to thought of the present invention, it should be considered as content disclosed in this invention equally.
Claims (7)
1. a cosmetic composition, is characterized in that, this cosmetic composition contains compound shown in following formula 1 and/or its pharmaceutically acceptable salt,
Wherein, the substituted or unsubstituted aryl of R to be carbon number be 4-20.
2. cosmetic composition according to claim 1; wherein; described aryl is phenyl, xenyl, thienyl, furyl, pyridine radicals, naphthyl, single benzofuranyl or two benzofuranyl; at least one in acyl group, cyano group, nitro, three halomethyl, phenyl, furyl and thienyl that the alkoxyl that the alkyl that substituent group on described aryl is selected from halogen, carbon number is 1-4, carbon number are 1-4, carbon number are 1-4, substituent group quantity is 1-5.
3. cosmetic composition according to claim 1 and 2, wherein, described aryl is phenyl, 4-fluorophenyl, 3-chlorphenyl, 4-methoxyphenyl, 3-pyridine radicals or 2-furyl.
4., according to the cosmetic composition in claim 1-3 described in any one, wherein, relative to the gross weight of described cosmetic composition, shown in described formula 1, the content of compound and/or its pharmaceutically acceptable salt is 0.1-10 % by weight.
5. cosmetic composition according to claim 4, wherein, relative to the gross weight of described cosmetic composition, shown in described formula 1, the content of compound and/or its pharmaceutically acceptable salt is 0.5-5 % by weight.
6. according to the cosmetic composition in claim 1-5 described in any one, wherein, described cosmetic composition is emulsion, emulsifiable paste, skin cream, essence, facial film, lip pomade, foundation cream, beautifying liquid, soap, shampoo, hair conditioner or bath gel.
7. according to the cosmetic composition in claim 1-5 described in any one at skin moisture-keeping, brighten and strengthen the application in gloss.
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|---|---|---|---|---|
| CN1863811A (en) * | 2003-10-01 | 2006-11-15 | 第一精密化学株式会社 | Stable vitamin B6 derivative |
| WO2008139965A1 (en) * | 2007-05-07 | 2008-11-20 | Daiichi Fine Chemical Co., Ltd. | Novel vitamin b6 derivative |
| CN101311174A (en) * | 2007-05-23 | 2008-11-26 | 吴方 | Vitamin B6 derivates and pharmaceutical use thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN1863811A (en) * | 2003-10-01 | 2006-11-15 | 第一精密化学株式会社 | Stable vitamin B6 derivative |
| WO2008139965A1 (en) * | 2007-05-07 | 2008-11-20 | Daiichi Fine Chemical Co., Ltd. | Novel vitamin b6 derivative |
| CN101311174A (en) * | 2007-05-23 | 2008-11-26 | 吴方 | Vitamin B6 derivates and pharmaceutical use thereof |
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