CN101040824A - Application of dimethylaminobenzaldehyde thiosemicarbazide in the whitening cosmetics - Google Patents
Application of dimethylaminobenzaldehyde thiosemicarbazide in the whitening cosmetics Download PDFInfo
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- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 1
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Abstract
The invention relates to a paradimethy-laminobenzaldehyde thiosemicarbazone as tyrosinase restrainer, in particular to the paradimethy-laminobenzaldehyde thiosemicarbazone applied in beauty cosmetics. The invention uses paradimethy-laminobenzaldehyde thiosemicarbazone with high-effect restrain function on the activity of tyrosinase as whitening agent to prepare beauty cosmetics, and provides a relative beauty cosmetics and a preparation. The invention uses paradimethy-laminobenzaldehyde thiosemicarbazone as whitening agent of de-crease beauty cosmetics solution which contains sea fish collagen peptide, paradimethy-laminobenzaldehyde thiosemicarbazone, alcohol, glycerin, methyl glycol, plant essence, conservative and water, that dissolves sea fish collagen peptide into water to obtain solution A, dissolves conservative and paradimethy-laminobenzaldehyde thiosemicarbazone into alcohol to obtain solution B, adds glycerin and methyl glycol into solution B to obtain solution C, mixes the solutions A and C, and adds water to form solution D, and adds plant essence into the solution D.
Description
Technical field
The present invention relates to a kind of paradime thylaminobenzaldehyde thiosemicarbazones, especially relate to the paradime thylaminobenzaldehyde thiosemicarbazones and be applied to skin-lightening cosmetic as brightening agent as tyrosinase inhibitor.
Background technology
Tryrosinase extensively is present in the organism, be the biosynthetic key enzyme of melanocyte (Mayer AM, Harel E.Phenoloxidases and their significance in fruit and vegetables.Food Enzymology, Fox P F.Ed, Elsevier; London, 1998,373-398) in organism, tryrosinase at first hydroxylating tyrosine generates L-DOPA, and oxidation L-DOPA generates the DOPA quinone then, and the DOPA quinone forms melanin through a series of enzyme catalysiss and non-enzymatic catalysis reaction again.Therefore, tryrosinase is the synthetic rate-limiting enzyme of melanocyte, it is active relevant with the melanocyte synthetic quantity, can by regulate and control its vigor regulate and control the growing amount of melanocyte (Friedman M.Food browning and its prevention:an overview[J] .J.Agric.Food Chem., 1996,44 (3): 631-653).At present, the whitening composition in the skin-lightening cosmetic mainly carries out the screening of whitening agent as target spot with tryrosinase.The extract of whitening agent that circulates on the market such as kojic acid, Arbutin and some Chinese herbal medicine all is tyrosinase inhibitors.But existing whitening agent effect is not very good, and some also has certain side effect, therefore, presses for the Synthetic inhibitor of melanin that research efficiently has no side effect.
Studies show that (thiosemicarbazone) compound has multiple biological activitys such as antibacterium, tuberculosis, antiviral, antitumor.(Dobek AS, Klaman DL, Dikson ET, et al.Inhibition of clinically significant bacterial organismsin vitro by 2-acetypyridine thiosemicarbazones[J] .Antimicrob Agents Chemother, 1980,18:27; Shukla HK, Desai NC, Astik RR, et al.Studies on some thiosemicarbazones and1,3,4-thiadiazolines as potential antitubercular and antibacterial agents[J] .J Indian Chem Soc, 1984; 61 (2): 168-169; Wilson HR, Revankar GR, Tolman RL.In vivo activity of certainthiosemicarbazones against Trypanosoma cruzi[J] .J Med Chem, 1974,17 (7): 760-761.) still, it does not have report as yet to tryrosinase and the synthetic inhibitory action of melanin, and this compounds being applied in cosmetics still belongs to blank both at home and abroad.Simultaneously, for designing better and the development of new Synthetic inhibitor of melanin, be necessary to inquire into the inhibitory action mechanism of inhibitor to tryrosinase.At present, the brightening agent of main skin-lightening cosmetic generally adopts natural extract on the market, but the natural extract complicated component causes and extracts and processing difficulties.And the brightening agent of chemosynthesis helps producing in enormous quantities, and its processing technology is simple, and whitening effect is quick and remarkable, but has the problem of safety easily, can not be ignored.
Summary of the invention
Chemical compound-paradime thylaminobenzaldehyde the thiosemicarbazones that the objective of the invention is to have efficient restraint of tyrosinase vigor is as the application of brightening agent in the preparation cosmetics.
Another object of the present invention provides a kind of chemical compound-paradime thylaminobenzaldehyde thiosemicarbazones that will have an efficient restraint of tyrosinase vigor as skin-lightening cosmetic of brightening agent and preparation method thereof.
The chemical structural formula of paradime thylaminobenzaldehyde thiosemicarbazones of the present invention is:
Paradime thylaminobenzaldehyde thiosemicarbazones of the present invention is a kind of chemical compound with efficient restraint of tyrosinase vigor, can be used as brightening agent and is used to prepare cosmetics.
Below providing the chemical compound-paradime thylaminobenzaldehyde thiosemicarbazones that will have efficient restraint of tyrosinase vigor consists of as the raw material of a kind of wrinkle removal whitening astringent of brightening agent:
Marine fish collagen peptide, paradime thylaminobenzaldehyde thiosemicarbazones, ethanol, glycerol, propylene glycol, plant essence, antiseptic and water, its content is marine fish collagen peptide 5%～50% by mass percentage, paradime thylaminobenzaldehyde thiosemicarbazones 0.01%～0.05%, ethanol 1%～2%, glycerol 10%～30%, propylene glycol 0.5%～2%, plant essence 0.002%～0.008%, antiseptic 0.1%～0.2%, Yu Weishui.
Plant essence can be selected a kind of in geraniol, Flos Rosae Rugosae quintessence oil, Flos Jasmini Sambac quintessence oil, Garden lavender quintessence oil, rosemary ethereal oil, Flos Pelargonii quintessence oil, clove oil, the lemon extract wet goods for use.
Antiseptic can be selected at least a in Buddhist nun uncle tortoise beetle ester, Ethyl Hydroxybenzoate, the Ni Baijin propyl ester etc. for use.
Below provide the chemical compound-paradime thylaminobenzaldehyde thiosemicarbazones that to have efficient restraint of tyrosinase vigor preparation method, the steps include: as a kind of wrinkle removal whitening astringent of brightening agent
1) it is soluble in water to take by weighing the marine fish collagen peptide by said ratio, marine fish collagen protein peptide solution, be designated as solution A;
2) take by weighing antiseptic and the paradime thylaminobenzaldehyde thiosemicarbazones is dissolved in dehydrated alcohol, solution B;
3) in solution B, add glycerol and propylene glycol, get solution C;
4) solution A and solution C are mixed, add the water mixing, get solution D;
5) add plant essence in solution D, mixing gets target product wrinkle removal whitening astringent.
At least a with in distilled water, deionized water and the pure water etc. of described wet concentration.
Paradime thylaminobenzaldehyde thiosemicarbazones of the present invention is as follows as a kind of effect of cosmetics brightening agent:
The paradime thylaminobenzaldehyde thiosemicarbazones at room temperature can be dissolved in ethanol well, is easy to be applied in the cosmetics.Adopt the enzyme dynamics method, studies show that by inhibition effect tryrosinase, thiosemicarbazides, paradime thylaminobenzaldehyde and paradime thylaminobenzaldehyde thiosemicarbazones are respectively 2.54mmol/L to active half suppression ratio of Mushroom Tyrosinase, 0.665mmol/L, 2.7 μ mol/L (see figure 1)s.With the tryrosinase of slightly carrying mice B16 cell is object of study, then half suppression ratio of paradime thylaminobenzaldehyde thiosemicarbazones is 134.5 μ mol/L, and when paradime thylaminobenzaldehyde concentration was lower than 7.5mmol/L, its suppression ratio to enzymatic activity still only had 54.5% (see figure 2).Double suppression ratio embodied the inhibition strength of inhibitor to enzyme, and half suppression ratio is more little, illustrates that inhibition strength is strong more.At present, detection compound becomes the index of this compounds of measurement as the whitening effect of cosmetics brightening agent to the inhibition activity of tryrosinase.Chemical compound is big more to the inhibition strength of tryrosinase, shows that its whitening effect is good more.Can be shown that by experimental result the paradime thylaminobenzaldehyde thiosemicarbazones has very strong inhibitory action to tryrosinase, its inhibition strength strengthens greatly with respect to its two raw materials.Show by experimental result, the paradime thylaminobenzaldehyde thiosemicarbazones is the reversible inhibitor (see figure 3) of this enzyme, and by this chemical compound the double-reciprocal plot (see figure 4) of the inhibition mechanism research of tryrosinase is shown that this chemical compound is the mixed-type inhibitor of tryrosinase.And can try to achieve the inhibition constant (K of chemical compound by the straight slope of Fig. 5 and Fig. 6 respectively to resolvase
I) be 1.78 μ mol/L, chemical compound is to the inhibition constant (K of resolvase
I) be 6.43 μ mol/L.Chemical compound to the inhibitory action mechanism of Mushroom Tyrosinase referring to table 1.
Table 1
| Chemical compound | IC 50 (μmol/L) | Inhibitory action | Suppress type | Inhibition constants (μmol/L) | |
| K I | K IS | ||||
| Thiosemicarbazides (a) | 2240 | Reversible | Non-competing | 2200 | 2200 |
| 4-dimethylaminobenzaldehyde (b) | 665 | Reversible | Competition | 665 | - |
| 4-dimethylaminobenzaldehyde thiosemicarbazones (c) | 2.7 | Reversible | Mixed I type | 1.78 | 6.43 |
The safety of chemical compound is referring to Fig. 7, and figure is represented relative cell survival rate from left to right successively, relatively tyrosinase residue vigor, melanin content relatively.From cytotoxicity, when the concentration of paradime thylaminobenzaldehyde thiosemicarbazones reached 100 μ mol/L, it had only 14.5% to the growth inhibition ratio of mice B16, and toxicity is less; And when the concentration of paradime thylaminobenzaldehyde thiosemicarbazones reached 100 μ mol/L, tyrosinase activity had stronger inhibition effect in its pair cell, and suppression ratio reaches 11.7%; Melanic content also has the obvious suppression effect in its pair cell, and when concentration was 100 μ mol/L, suppression ratio was 50%.Result of study shows that the toxicity of paradime thylaminobenzaldehyde thiosemicarbazones is less, and restraint of tyrosinase is active strong, can suppress melanic generation effectively, is a kind of very promising cosmetics brightening agent.
Description of drawings
Fig. 1 is thiosemicarbazides (a), paradime thylaminobenzaldehyde (b) and paradime thylaminobenzaldehyde thiosemicarbazones (c) depression effect to Mushroom Tyrosinase.In Fig. 1, abscissa is the concentration [I] of inhibitor, and vertical coordinate is tryrosinase relative surplus vigor Activity (%).
Fig. 2 is paradime thylaminobenzaldehyde (b) and paradime thylaminobenzaldehyde thiosemicarbazones (c) depression effect to tryrosinase vigor in the mice B16 cell of slightly carrying.In Fig. 2, abscissa is the concentration [I] of inhibitor, and vertical coordinate is tryrosinase relative surplus vigor Activity (%).
Fig. 3 is the depression effect of paradime thylaminobenzaldehyde thiosemicarbazones to tryrosinase.In Fig. 3,5 straight lines are respectively 1,2, and 3,4,5; Abscissa is tryrosinase concentration [E] (μ g/ml), and vertical coordinate is the response speed v (μ M/min) of tryrosinase enzymatic reaction.
Fig. 4 is the paradime thylaminobenzaldehyde thiosemicarbazones suppresses type to tryrosinase judgement.In Fig. 4,5 straight lines are respectively 5,4, and 3,2,1; Abscissa is the inverse [S] of L-DOPA concentration
-1(μ M
-1), vertical coordinate is the v reciprocal of the response speed of tryrosinase enzymatic reaction
-1(μ M/min
-1).
Fig. 5 is the mensuration of paradime thylaminobenzaldehyde thiosemicarbazones to the inhibition constant of tryrosinase resolvase.In Fig. 5, abscissa is the concentration [I] (μ M) of paradime thylaminobenzaldehyde thiosemicarbazones, and vertical coordinate is the collinear vertical coordinate intercept of Fig. 4 Intercept.
Fig. 6 is the paradime thylaminobenzaldehyde thiosemicarbazones suppresses constant to tryrosinase substrate complex a mensuration.In Fig. 6, abscissa is the concentration [I] (μ M) of paradime thylaminobenzaldehyde thiosemicarbazones, and vertical coordinate is the slope S lope of Fig. 4 straight line portion.
Fig. 7 is the influence of paradime thylaminobenzaldehyde thiosemicarbazones to cell proliferation rate, tyrosinase activity and the melanin content of mice B16 cell.In Fig. 7, abscissa is the concentration [I] (μ M) of paradime thylaminobenzaldehyde thiosemicarbazones, and vertical coordinate is relative rate (%).Figure is represented relative cell survival rate from left to right successively, relatively tyrosinase residue vigor and relative melanin content.
The specific embodiment
Take by weighing 4g marine fish collagen peptide and add the 20ml distilled water, mixing obtains solution A.Take by weighing 0.3g Buddhist nun's uncle's tortoise beetle ester and 0.05g paradime thylaminobenzaldehyde thiosemicarbazones, add 1.5ml ethanol, mixing adds 18ml glycerol again, the 1.5ml propylene glycol, and mixing gets solution C.Solution A and solution C are mixed, and add the 30ml distilled water, add 3.1 μ l essence again, mixing the wrinkle removal whitening astringent.
Take by weighing 6g marine fish collagen peptide and add the 20ml distilled water, mixing obtains solution A.Take by weighing 0.25g Buddhist nun's uncle's tortoise beetle ester and 0.035g paradime thylaminobenzaldehyde thiosemicarbazones, add 1.0ml ethanol, mixing adds 25ml glycerol again, the 1.2ml propylene glycol, and mixing gets solution C.Solution A and solution C are mixed, and add the 20ml distilled water, add 4.5 μ l essence again, mixing whitening lotion.
Take by weighing 2.5g marine fish collagen peptide and add the 20ml distilled water, mixing obtains solution A.Take by weighing 0.15g Buddhist nun's uncle's tortoise beetle ester and 0.028g paradime thylaminobenzaldehyde thiosemicarbazones, add 1.2ml ethanol, mixing adds 18ml glycerol again, the 1.2ml propylene glycol, and mixing gets solution C.Solution A and solution C are mixed, and add the 30ml distilled water, add 5.0 μ l essence again, mixing whitening lotion.
Take by weighing 1g marine fish collagen peptide and add the 15ml distilled water, mixing obtains solution A.Take by weighing 0.18g Buddhist nun's uncle's tortoise beetle ester and 0.03g paradime thylaminobenzaldehyde thiosemicarbazones, add 1ml ethanol, mixing adds 12.5ml glycerol again, the 1.5ml propylene glycol, and mixing gets solution C.Solution A and solution C are mixed, and add the 20ml distilled water, add 3.0 μ l essence again, mixing whitening lotion.
Take by weighing 2g marine fish collagen peptide and add the 20ml distilled water, mixing obtains solution A.Take by weighing 0.1g Buddhist nun's uncle's tortoise beetle ester and 0.025g paradime thylaminobenzaldehyde thiosemicarbazones, add 1ml ethanol, mixing adds 15ml glycerol again, the 1.5ml propylene glycol, and mixing gets solution C.Solution A and solution C are mixed, and add the 12.5ml distilled water, add 2.0 μ l essence again, mixing whitening lotion.
Take by weighing 1g marine fish collagen peptide and add the 20ml distilled water, mixing obtains solution A.Take by weighing 0.15g Buddhist nun's uncle's tortoise beetle ester and 0.02g paradime thylaminobenzaldehyde thiosemicarbazones, add 0.8ml ethanol, mixing adds 10ml glycerol again, the 1ml propylene glycol, and mixing gets solution C.Solution A and solution C are mixed, and add the 18ml distilled water, add 2.5 μ l essence again, mixing whitening lotion.
Embodiment 7
Similar to Example 1, its difference is that its content is marine fish collagen peptide 5% by mass percentage, paradime thylaminobenzaldehyde thiosemicarbazones 0.04%, ethanol 1.5%, glycerol 20%, propylene glycol 1.5%, geraniol 0.005%, antiseptic Buddhist nun uncle tortoise beetle ester 0.16%, Yu Weishui.
Similar to Example 1, its difference is that its content is marine fish collagen peptide 15% by mass percentage, paradime thylaminobenzaldehyde thiosemicarbazones 0.02%, ethanol 1.2%, glycerol 10%, propylene glycol 1.8%, Flos Rosae Rugosae quintessence oil 0.003%, antiseptic Ethyl Hydroxybenzoate 0.15%, Yu Weishui.
Embodiment 9
Similar to Example 1, its difference is that its content is marine fish collagen peptide 20% by mass percentage, paradime thylaminobenzaldehyde thiosemicarbazones 0.01%, ethanol 1.8%, glycerol 25%, propylene glycol 1.0%, Flos Jasmini Sambac quintessence oil 0.006%, antiseptic Ni Baijin propyl ester 0.13%, Yu Weishui.
Similar to Example 1, its difference is that its content is marine fish collagen peptide 25% by mass percentage, paradime thylaminobenzaldehyde thiosemicarbazones 0.05%, ethanol 2%, glycerol 15%, propylene glycol 0.8%, Garden lavender quintessence oil 0.002%, antiseptic Buddhist nun uncle tortoise beetle ester 0.18%, Yu Weishui.
Embodiment 11
Similar to Example 1, its difference is that its content is marine fish collagen peptide 30% by mass percentage, paradime thylaminobenzaldehyde thiosemicarbazones 0.025%, ethanol 1.6%, glycerol 30%, propylene glycol 2%, rosemary ethereal oil 0.008%, antiseptic Ethyl Hydroxybenzoate 0.14%, Yu Weishui.
Embodiment 12
Similar to Example 1, its difference is that its content is marine fish collagen peptide 35% by mass percentage, paradime thylaminobenzaldehyde thiosemicarbazones 0.015%, ethanol 1.7%, glycerol 15%, propylene glycol 0.5%, Flos Pelargonii quintessence oil 0.004%, antiseptic Buddhist nun uncle tortoise beetle ester 0.2%, Yu Weishui.
Embodiment 13
Similar to Example 1, its difference is that its content is marine fish collagen peptide 40% by mass percentage, paradime thylaminobenzaldehyde thiosemicarbazones 0.035%, ethanol 1.4%, glycerol 18%, propylene glycol 1.2%, clove oil 0.007%, antiseptic Ethyl Hydroxybenzoate 0.16%, Yu Weishui.
Embodiment 14
Similar to Example 1, its difference is that its content is marine fish collagen peptide 50% by mass percentage, paradime thylaminobenzaldehyde thiosemicarbazones 0.03%, ethanol 1.3%, glycerol 16%, propylene glycol 1.6%, Fructus Citri Limoniae quintessence oil 0.005%, antiseptic Ni Baijin propyl ester 0.1%, Yu Weishui.
Claims (6)
1. the paradime thylaminobenzaldehyde thiosemicarbazones is as the application of brightening agent in the preparation cosmetics.
2. paradime thylaminobenzaldehyde thiosemicarbazones as claimed in claim 1 is characterized in that as the application of brightening agent in a kind of wrinkle removal whitening astringent of preparation its raw material consists of:
Marine fish collagen peptide, paradime thylaminobenzaldehyde thiosemicarbazones, ethanol, glycerol, propylene glycol, plant essence, antiseptic and water, its content is marine fish collagen peptide 5%～50% by mass percentage, paradime thylaminobenzaldehyde thiosemicarbazones 0.01%～0.05%, ethanol 1%～2%, glycerol 10%～30%, propylene glycol 0.5%～2%, plant essence 0.002%～0.008%, antiseptic 0.1%～0.2%, Yu Weishui.
3. paradime thylaminobenzaldehyde thiosemicarbazones as claimed in claim 2 in the application of preparation in a kind of wrinkle removal whitening astringent, is characterized in that plant essence is selected from a kind of in geraniol, Flos Rosae Rugosae quintessence oil, Flos Jasmini Sambac quintessence oil, Garden lavender quintessence oil, rosemary ethereal oil, Flos Pelargonii quintessence oil, clove oil and the Fructus Citri Limoniae quintessence oil as brightening agent.
4. paradime thylaminobenzaldehyde thiosemicarbazones as claimed in claim 2 in the application of preparation in a kind of wrinkle removal whitening astringent, is characterized in that antiseptic is selected from least a in Buddhist nun uncle tortoise beetle ester, Ethyl Hydroxybenzoate and the Ni Baijin propyl ester as brightening agent.
5. paradime thylaminobenzaldehyde thiosemicarbazones as claimed in claim 2 is characterized in that the steps include: as the preparation method of brightening agent at a kind of wrinkle removal whitening astringent of preparation
1) it is soluble in water to take by weighing the marine fish collagen peptide by said ratio, marine fish collagen protein peptide solution, be designated as solution A;
2) take by weighing antiseptic and the paradime thylaminobenzaldehyde thiosemicarbazones is dissolved in dehydrated alcohol, solution B;
3) in solution B, add glycerol and propylene glycol, get solution C;
4) solution A and solution C are mixed, add the water mixing, get solution D;
5) add plant essence in solution D, mixing gets target product wrinkle removal whitening astringent.
6. paradime thylaminobenzaldehyde thiosemicarbazones as claimed in claim 5 is as the preparation method of brightening agent at a kind of wrinkle removal whitening astringent of preparation, it is characterized in that at least a with in distilled water, deionized water and the pure water of described wet concentration.
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| CNB2007100088652A CN100512794C (en) | 2007-04-20 | 2007-04-20 | Application of dimethylaminobenzaldehyde thiosemicarbazide in the whitening cosmetics |
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| CN101450052B (en) * | 2007-11-30 | 2011-08-31 | 中国科学院上海药物研究所 | Use of black mulberry extract in preparing tyrosinase inhibitor |
| CN102827050A (en) * | 2012-09-17 | 2012-12-19 | 中山大学 | Methylene-thiosemicarbazone-based substituted phenoxy carboxylic acid derivative, and preparation method and application thereof |
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| CN105294527A (en) * | 2015-11-27 | 2016-02-03 | 中国广州分析测试中心 | Aryl-substituted benzaldehyde or acetophenone thiosemicarbazone derivative and application thereof as tyrosinase inhibitor |
| CN106176323A (en) * | 2016-08-24 | 2016-12-07 | 登封市科技企业孵化服务中心 | Plants essential oil Skin whitening care cosmetics |
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| US5683705A (en) * | 1996-03-29 | 1997-11-04 | Estee Lauder, Inc. | Sulfur-based amides and bis-amides useful against skin disorders |
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| CN101450052B (en) * | 2007-11-30 | 2011-08-31 | 中国科学院上海药物研究所 | Use of black mulberry extract in preparing tyrosinase inhibitor |
| CN102827050A (en) * | 2012-09-17 | 2012-12-19 | 中山大学 | Methylene-thiosemicarbazone-based substituted phenoxy carboxylic acid derivative, and preparation method and application thereof |
| CN102827050B (en) * | 2012-09-17 | 2014-10-22 | 中山大学 | Methylene-thiosemicarbazone-based substituted phenoxy carboxylic acid derivative, and preparation method and application thereof |
| CN103724243A (en) * | 2014-01-16 | 2014-04-16 | 厦门大学 | 4-methoxybenzaldehyde L-cysteine schiff base and preparation method and application thereof |
| CN104644523A (en) * | 2015-01-27 | 2015-05-27 | 广西达庆生物科技有限公司 | Medical biological wrinkle-removing and speckle-inhibiting dressing and preparation method thereof |
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| CN105294527A (en) * | 2015-11-27 | 2016-02-03 | 中国广州分析测试中心 | Aryl-substituted benzaldehyde or acetophenone thiosemicarbazone derivative and application thereof as tyrosinase inhibitor |
| CN106176323A (en) * | 2016-08-24 | 2016-12-07 | 登封市科技企业孵化服务中心 | Plants essential oil Skin whitening care cosmetics |
| CN113025437A (en) * | 2021-03-11 | 2021-06-25 | 河南瑞奇特新材料有限公司 | Washing whitening agent and preparation method thereof |
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