CN117180122B - Composition for relaxing and repairing allergy and application thereof - Google Patents
Composition for relaxing and repairing allergy and application thereof Download PDFInfo
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- CN117180122B CN117180122B CN202311444287.2A CN202311444287A CN117180122B CN 117180122 B CN117180122 B CN 117180122B CN 202311444287 A CN202311444287 A CN 202311444287A CN 117180122 B CN117180122 B CN 117180122B
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- 239000000203 mixture Substances 0.000 title claims abstract description 125
- 206010020751 Hypersensitivity Diseases 0.000 title claims abstract description 56
- 208000026935 allergic disease Diseases 0.000 title claims abstract description 56
- 230000007815 allergy Effects 0.000 title description 2
- 230000002040 relaxant effect Effects 0.000 title description 2
- 238000002360 preparation method Methods 0.000 claims abstract description 83
- GFEYWOGCSROPRT-OBXVVNIGSA-N (2s)-1-[(2s)-2-[[(2s)-1-[(2s)-2-[[(2s)-2-[[(2s)-2-amino-3-phenylpropanoyl]amino]-3-methylbutanoyl]amino]propanoyl]pyrrolidine-2-carbonyl]amino]-3-phenylpropanoyl]pyrrolidine-2-carboxylic acid Chemical compound C([C@H](N)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N1[C@@H](CCC1)C(O)=O)C1=CC=CC=C1 GFEYWOGCSROPRT-OBXVVNIGSA-N 0.000 claims abstract description 49
- 108010047657 Phe-Val-Ala-Pro-Phe-Pro Proteins 0.000 claims abstract description 49
- 241000186660 Lactobacillus Species 0.000 claims abstract description 40
- 238000000855 fermentation Methods 0.000 claims abstract description 40
- 230000004151 fermentation Effects 0.000 claims abstract description 40
- 229940039696 lactobacillus Drugs 0.000 claims abstract description 40
- 239000006166 lysate Substances 0.000 claims abstract description 40
- QRYRORQUOLYVBU-VBKZILBWSA-N Carnosic acid Natural products CC([C@@H]1CC2)(C)CCC[C@]1(C(O)=O)C1=C2C=C(C(C)C)C(O)=C1O QRYRORQUOLYVBU-VBKZILBWSA-N 0.000 claims abstract description 39
- 108010087806 Carnosine Proteins 0.000 claims abstract description 39
- CQOVPNPJLQNMDC-UHFFFAOYSA-N N-beta-alanyl-L-histidine Natural products NCCC(=O)NC(C(O)=O)CC1=CN=CN1 CQOVPNPJLQNMDC-UHFFFAOYSA-N 0.000 claims abstract description 39
- CQOVPNPJLQNMDC-ZETCQYMHSA-N carnosine Chemical compound [NH3+]CCC(=O)N[C@H](C([O-])=O)CC1=CNC=N1 CQOVPNPJLQNMDC-ZETCQYMHSA-N 0.000 claims abstract description 39
- 229940044199 carnosine Drugs 0.000 claims abstract description 39
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 claims abstract description 31
- SPLVTQKVMVVJPT-UHFFFAOYSA-N 3-carbamimidoylsulfanylpropanoic acid;hydrochloride Chemical compound Cl.NC(=N)SCCC(O)=O SPLVTQKVMVVJPT-UHFFFAOYSA-N 0.000 claims abstract description 12
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 claims abstract description 12
- 230000008439 repair process Effects 0.000 claims description 103
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical group CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- ZFCHNZDUMIOWFV-UHFFFAOYSA-N pyrimidine-2-carboxylic acid Chemical class OC(=O)C1=NC=CC=N1 ZFCHNZDUMIOWFV-UHFFFAOYSA-N 0.000 claims description 12
- 238000002156 mixing Methods 0.000 claims description 7
- 239000003513 alkali Substances 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 4
- 238000010306 acid treatment Methods 0.000 claims description 3
- 239000002537 cosmetic Substances 0.000 claims description 3
- 239000003153 chemical reaction reagent Substances 0.000 claims description 2
- 230000000694 effects Effects 0.000 abstract description 7
- 231100000135 cytotoxicity Toxicity 0.000 abstract description 5
- 230000003013 cytotoxicity Effects 0.000 abstract description 5
- 230000002378 acidificating effect Effects 0.000 abstract description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 78
- 238000013329 compounding Methods 0.000 description 32
- 229940049964 oleate Drugs 0.000 description 26
- 210000003491 skin Anatomy 0.000 description 26
- 238000012360 testing method Methods 0.000 description 15
- FKENQMMABCRJMK-RITPCOANSA-N sulbactam Chemical compound O=S1(=O)C(C)(C)[C@H](C(O)=O)N2C(=O)C[C@H]21 FKENQMMABCRJMK-RITPCOANSA-N 0.000 description 13
- 229960005256 sulbactam Drugs 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000000243 solution Substances 0.000 description 8
- 210000004027 cell Anatomy 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 7
- 150000004729 acetoacetic acid derivatives Chemical class 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 239000001963 growth medium Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 210000002615 epidermis Anatomy 0.000 description 5
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000000967 suction filtration Methods 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 3
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 description 3
- 230000004888 barrier function Effects 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 108090000765 processed proteins & peptides Proteins 0.000 description 3
- 150000003230 pyrimidines Chemical class 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 230000001105 regulatory effect Effects 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 210000004207 dermis Anatomy 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N isothiourea group Chemical group NC(S)=N UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- 102000004196 processed proteins & peptides Human genes 0.000 description 2
- 238000002390 rotary evaporation Methods 0.000 description 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
- BGRJTUBHPOOWDU-NSHDSACASA-N (S)-(-)-sulpiride Chemical compound CCN1CCC[C@H]1CNC(=O)C1=CC(S(N)(=O)=O)=CC=C1OC BGRJTUBHPOOWDU-NSHDSACASA-N 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- 108010087230 Sincalide Proteins 0.000 description 1
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- 230000009286 beneficial effect Effects 0.000 description 1
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000010609 cell counting kit-8 assay Methods 0.000 description 1
- 239000006143 cell culture medium Substances 0.000 description 1
- 239000006285 cell suspension Substances 0.000 description 1
- 230000003833 cell viability Effects 0.000 description 1
- 231100000263 cytotoxicity test Toxicity 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
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- 238000004821 distillation Methods 0.000 description 1
- 239000012091 fetal bovine serum Substances 0.000 description 1
- 210000002950 fibroblast Anatomy 0.000 description 1
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 210000002510 keratinocyte Anatomy 0.000 description 1
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- 238000012544 monitoring process Methods 0.000 description 1
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- 239000000419 plant extract Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- IZTQOLKUZKXIRV-YRVFCXMDSA-N sincalide Chemical compound C([C@@H](C(=O)N[C@@H](CCSC)C(=O)NCC(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(N)=O)NC(=O)[C@@H](N)CC(O)=O)C1=CC=C(OS(O)(=O)=O)C=C1 IZTQOLKUZKXIRV-YRVFCXMDSA-N 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 229960004940 sulpiride Drugs 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
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Abstract
The invention discloses a comfort restoration composition and application thereof, which belong to the technical field of skin restoration, and in particular relates to a comfort restoration composition at least containing S-substituent pyrimidinyl carboxylic acid derivatives, wherein the comfort restoration composition can also contain at least 1 of hexapeptide-11, decarboxylated carnosine and lactobacillus fermentation lysate, in the preparation of the S-substituent pyrimidinyl carboxylic acid derivatives, firstly, acetoacetic acid ethyl ester and triethyl orthoformate are reacted to prepare the acetoacetic acid ethyl ester derivatives, then S-carboxyethyl isothiourea chloride and the acetoacetic acid ethyl ester derivatives are used for preparing the S-substituent pyrimidinyl carboxylic acid derivatives, and finally, the S-substituent pyrimidinyl carboxylic acid derivatives are prepared by the S-substituent pyrimidinyl carboxylic acid derivatives under alkaline conditions and acidic conditions. The allergy-relieving restoration composition prepared by the invention has small cytotoxicity, can effectively reduce the moisture loss of the skin, and has allergy-relieving restoration effect on the skin.
Description
Technical Field
The invention belongs to the technical field of skin repair, and particularly relates to a allergy-relieving repair composition and application thereof.
Background
Skin integrity is the ultimate goal of research pursuit of skin repair materials. However, most of the repairing raw materials only act on the epidermis layer of the skin at present, and promote the proliferation of cells of the epidermis, so that the surface layer of the skin is repaired, and the integrity of the barrier of the epidermis is achieved. The integrity of the skin is not limited to the epidermis which is used as a physiological barrier, but also comprises a microorganism layer which is used as a biochemical barrier, and the repair of physiological structures such as a basal membrane, a dermis layer and the like which support the skin structure, so that the skin exists in a complete form.
The damage of epidermis and dermis is represented by the attenuation and withering of keratinocytes and fibroblasts, which is a point of much cosmetic concern at present, but the raw materials and compositions for skin repair are mainly researched at one target point or one to two target points, and plant extract components are mainly used, so that the raw materials and compositions for beautifying peptides for skin repair are relatively less, and particularly, the combination of skin repair with synthetic biological products such as peptides is still blank.
Disclosure of Invention
The invention aims to provide a allergy-relieving restoration composition which has small cytotoxicity, effectively reduces the water loss of skin and has allergy-relieving restoration effect and application thereof.
The technical scheme adopted by the invention for achieving the purpose is as follows:
a allergy-relieving repair composition comprising: at least comprising S-substituent pyrimidinyl carboxylic acid derivatives, and further comprising at least 1 of hexapeptide-11, decarboxylated carnosine and lactobacillus fermentation lysate; s-substituent pyrimidinyl carboxylic acid derivative has isothiourea group. According to the invention, the acetoacetic acid ethyl ester derivative is prepared by reacting acetoacetic acid ethyl ester and triethyl orthoformate, then the S-substituent pyrimidine derivative is prepared by reacting S-carboxyethyl isothiourea chloride with the acetoacetic acid ethyl ester derivative, finally the S-substituent pyrimidine derivative is prepared into the S-substituent pyrimidine carboxylic acid derivative, and then the S-substituent pyrimidine carboxylic acid derivative is mixed with at least 1 of hexapeptide-11, decarboxylated carnosine and lactobacillus fermentation lysate to prepare the comfort repair composition, so that the comfort repair composition containing the S-substituent pyrimidine carboxylic acid derivative can effectively reduce the water loss of skin, and has excellent effects.
Preferably, the S-substituent pyrimidinyl carboxylic acid derivative and hexapeptide-11 are present in a mass ratio of 1: mixing at a ratio of 0.1-10; or, S-substituent pyrimidinyl carboxylic acid derivative and decarboxylated carnosine in a mass ratio of 1: mixing at a ratio of 0.1-10; or, S-substituent pyrimidinyl carboxylic acid derivative and lactobacillus fermentation lysate in a mass ratio of 1: mixing at a ratio of 0.1-10.
The invention discloses application of the allergy-relieving repair composition in cosmetics.
The invention discloses a preparation method of an S-substituent pyrimidinyl carboxylic acid derivative, which comprises the following steps: the method comprises the steps of reacting acetoacetic acid ethyl ester with triethyl orthoformate to obtain an acetoacetic acid ethyl ester derivative, reacting S-carboxyethyl isothiourea chloride with the acetoacetic acid ethyl ester derivative to obtain an S-substituent pyrimidine derivative, and finally preparing the S-substituent pyrimidine carboxylic acid derivative from the S-substituent pyrimidine derivative; s-substituent pyrimidinyl carboxylic acid derivative has isothiourea group.
Preferably, the amount of triethyl orthoformate used is 60-80wt% of ethyl acetoacetate; or the S-carboxyethyl isothiourea chloride is used in an amount of 70-90wt% of the acetoacetic ester derivative; or, the S-substituent pyrimidinyl carboxylic acid derivative is prepared by alkali treatment and acid treatment.
Preferably, the temperature of the alkali treatment is 40-70 ℃; or, the alkaline reagent in the alkaline treatment is sodium hydroxide solution with the concentration of 0.5-2mol/L.
Preferably, the preparation solvent of the acetoacetic acid ethyl ester derivative is acetic anhydride; or, the solvent for preparing the S-substituent pyrimidine derivative is ethanol.
Preferably, in the preparation of the acetoacetic acid ethyl ester derivative, acetoacetic acid ethyl ester, triethyl orthoformate and acetic anhydride are mixed and reacted for 1 to 4 hours under stirring at a temperature of between 100 and 120 ℃, and after the reaction is completed, acetic anhydride is removed by distillation under reduced pressure, thus obtaining the acetoacetic acid ethyl ester derivative.
More preferably, in the preparation of the acetoacetate derivative, the acetoacetate is used in an amount of 40 to 60% by weight of acetic anhydride.
More preferably, in the preparation of the acetoacetate derivative, the amount of triethyl orthoformate used is 60 to 80% by weight of the acetoacetate.
Preferably, in the preparation of the S-substituent pyrimidine derivative, the S-carboxyethyl isothiourea chloride and the acetoacetic ester derivative are added into ethanol, the pH is regulated to 8-9, the mixture is stirred and reacted for 4-8 hours at 20-40 ℃, after the reaction is finished, the mixture is concentrated by rotary evaporation, ice bath treatment is carried out for 5-30min, solids are separated out, suction filtration is carried out, and the solids are collected, so that the S-substituent pyrimidine derivative is obtained.
More preferably, in the preparation of the S-substituted pyrimidine derivative, the ethyl acetoacetate derivative is used in an amount of 30 to 60% by weight of ethanol.
More preferably, in the preparation of the S-substituted pyrimidine derivative, the S-carboxyethyl isothiourea chloride is used in an amount of 70 to 90wt% of the acetoacetate derivative.
Preferably, in the preparation of the S-substituent pyrimidinyl carboxylic acid derivative, the S-substituent pyrimidinyl carboxylic acid derivative is added into sodium hydroxide solution, heated to 40-70 ℃ and stirred until complete dissolution, TLC detection reaction is complete, pH is regulated to 2-3 after cooling, solid is separated out, and suction filtration is carried out to obtain the S-substituent pyrimidinyl carboxylic acid derivative.
More preferably, the concentration of sodium hydroxide solution in the preparation of the S-substituted pyrimidinyl carboxylic acid derivative is 0.5-2mol/L.
More preferably, the S-substituted pyrimidine carboxylic acid derivative is prepared in an amount of 4 to 12% by weight of the sodium hydroxide solution.
The invention discloses a preparation method of a allergy-relieving repair composition, which comprises the following steps: a process for preparing the S-substituent pyrimidinyl carboxylic acid derivative.
Preferably, the S-substituent pyrimidinyl carboxylic acid derivative is mixed with at least 1 of hexapeptide-11, decarboxylated carnosine and lactobacillus fermentation lysate to prepare the sulbactam composition.
The invention discloses a sensitivity-relieving repair composition which at least comprises an S-substituent pyrimidinyl carboxylic acid derivative and at least comprises 1 of hexapeptide-11, decarboxylated carnosine and lactobacillus fermentation lysate.
Preferably, in the preparation of the comfort repair composition, the S-substituent pyrimidinyl carboxylic acid derivative and the hexapeptide-11 are compounded to obtain the comfort repair composition.
More preferably, in the preparation of the comfort repair composition, the S-substituent pyrimidinyl carboxylic acid derivative and hexapeptide-11 are mixed in a mass ratio of 1: compounding in a ratio of 0.1-10.
Preferably, in the preparation of the comfort repair composition, the S-substituent pyrimidinyl carboxylic acid derivative and the decarboxylated carnosine are compounded to obtain the comfort repair composition.
More preferably, in the preparation of the comfort repair composition, the S-substituent pyrimidinyl carboxylic acid derivative and the decarboxylated carnosine are mixed in a mass ratio of 1: compounding in a ratio of 0.1-10.
Preferably, in the preparation of the sulbactam composition, the S-substituent pyrimidinyl carboxylic acid derivative and the lactobacillus fermentation lysate are compounded to obtain the sulbactam composition.
More preferably, in the preparation of the comfort repair composition, the S-substituent pyrimidinyl carboxylic acid derivative and the lactobacillus fermentation lysate are present in a mass ratio of 1: compounding in a ratio of 0.1-10.
Preferably, in the preparation of the comfort repair composition, the S-substituent pyrimidinyl carboxylic acid derivative, hexapeptide-11 and decarboxylated carnosine are compounded to obtain the comfort repair composition.
More preferably, in the preparation of the comfort repair composition, the S-substituent pyrimidinyl carboxylic acid derivative, hexapeptide-11 and decarboxylated carnosine are mixed in a mass ratio of 1:0.1-10: compounding in a ratio of 0.1-10.
Preferably, in the preparation of the comfort repair composition, the S-substituent pyrimidinyl carboxylic acid derivative, the hexapeptide-11 and the lactobacillus fermentation lysate are compounded to obtain the comfort repair composition.
More preferably, in the preparation of the sulbactam repair composition, the S-substituent pyrimidinyl carboxylic acid derivative, hexapeptide-11 and lactobacillus fermentation lysate are present in a mass ratio of 1:0.1-10: compounding in a ratio of 0.1-10.
Preferably, in the preparation of the sulbactam composition, the S-substituent pyrimidinyl carboxylic acid derivative, hexapeptide-11, decarboxylated carnosine and lactobacillus fermentation lysate are compounded to obtain the sulbactam composition.
More preferably, in the preparation of the sulbactam repair composition, the S-substituent pyrimidinyl carboxylic acid derivative, hexapeptide-11, decarboxylated carnosine and lactobacillus fermentation lysate are present in a mass ratio of 1:0.1-10:0.1-10: compounding in a ratio of 0.1-10.
Preferably, propylene glycol oleate can be added in the preparation of the allergy-relieving repair composition, and the skin repair composition has the effect of further reducing the water loss of the skin and improves the repair of the skin under the action of at least 1 of S-substituent pyrimidinyl carboxylic acid derivatives, hexapeptide-11, decarboxylated carnosine and lactobacillus fermentation lysate.
Preferably, in the preparation of the comfort repair composition, the S-substituent pyrimidinyl carboxylic acid derivative, hexapeptide-11 and propylene glycol oleate are compounded to obtain the comfort repair composition.
More preferably, in the preparation of the comfort repair composition, the S-substituent pyrimidinyl carboxylic acid derivative, hexapeptide-11 and propylene glycol oleate are mixed according to a mass ratio of 1:0.1-10: compounding in the ratio of 0.02-0.2.
Preferably, in the preparation of the comfort repair composition, the S-substituent pyrimidinyl carboxylic acid derivative, the decarboxylated carnosine and the propylene glycol oleate are compounded to obtain the comfort repair composition.
More preferably, in the preparation of the comfort repair composition, the S-substituent pyrimidinyl carboxylic acid derivative, the decarboxylated carnosine and the propylene glycol oleate are mixed according to the mass ratio of 1:0.1-10: compounding in the ratio of 0.02-0.2.
Preferably, in the preparation of the comfort repair composition, the S-substituent pyrimidinyl carboxylic acid derivative, the lactobacillus fermentation lysate and the propylene glycol oleate are compounded to obtain the comfort repair composition.
More preferably, in the preparation of the comfort repair composition, the S-substituent pyrimidinyl carboxylic acid derivative, the lactobacillus fermentation lysate and the propylene glycol oleate are mixed according to the mass ratio of 1:0.1-10: compounding in the ratio of 0.02-0.2.
Preferably, in the preparation of the comfort repair composition, the S-substituent pyrimidinyl carboxylic acid derivative, hexapeptide-11, decarboxylated carnosine and propylene glycol oleate are compounded to obtain the comfort repair composition.
More preferably, in the preparation of the comfort repair composition, the S-substituent pyrimidinyl carboxylic acid derivative, hexapeptide-11, decarboxylated carnosine and propylene glycol oleate are mixed in a mass ratio of 1:0.1-10:0.1-10: compounding in the ratio of 0.02-0.2.
Preferably, in the preparation of the comfort repair composition, the S-substituent pyrimidinyl carboxylic acid derivative, hexapeptide-11, lactobacillus fermentation lysate and propylene glycol oleate are compounded to obtain the comfort repair composition.
More preferably, in the preparation of the sulbactam composition, the S-substituent pyrimidinyl carboxylic acid derivative, hexapeptide-11, lactobacillus fermentation lysate and propylene glycol oleate are mixed in a mass ratio of 1:0.1-10:0.1-10: compounding in the ratio of 0.02-0.2.
Preferably, in the preparation of the comfort repair composition, the S-substituent pyrimidinyl carboxylic acid derivative, hexapeptide-11, decarboxylated carnosine, lactobacillus fermentation lysate and propylene glycol oleate are compounded to obtain the comfort repair composition.
More preferably, in the preparation of the sulbactam repair composition, the S-substituent pyrimidinyl carboxylic acid derivative, hexapeptide-11, decarboxylated carnosine, lactobacillus fermentation lysate and propylene glycol oleate are present in a mass ratio of 1:0.1-10:0.1-10:0.1-10: compounding in the ratio of 0.02-0.2.
The sulbactam composition of the invention at least contains S-substituent pyrimidinyl carboxylic acid derivatives, and can also contain at least 1 of hexapeptide-11, decarboxylation carnosine and lactobacillus fermentation lysate, in the preparation of the S-substituent pyrimidinyl carboxylic acid derivatives, firstly, the ethyl acetoacetate and triethyl orthoformate react to prepare the ethyl acetoacetate derivatives, then the S-substituent pyrimidine derivatives are prepared from S-carboxyethyl isothiourea chloride and the ethyl acetoacetate derivatives, and finally the S-substituent pyrimidinyl carboxylic acid derivatives are prepared from the S-substituent pyrimidine derivatives under the treatment of alkaline condition and acidic condition, and then the sulbactam composition is prepared by compounding, thus the sulbactam composition has the following beneficial effects: the allergy-relieving restoration composition prepared by the invention has small cytotoxicity, can effectively reduce the moisture loss of the skin, and has allergy-relieving restoration effect on the skin. Therefore, the invention is a allergy-relieving restoration composition with small cytotoxicity, effective reduction of moisture loss of skin and allergy-relieving restoration effect and application thereof.
Drawings
FIG. 1 is an infrared spectrogram;
fig. 2 is a Δtewl diagram.
Detailed Description
The technical scheme of the invention is further described in detail below with reference to the specific embodiments and the attached drawings:
hexapeptide-11, lactobacillus fermentation lysate and decarboxylated carnosine in the present invention are from Hua Xi biosciences Inc. or Zhejiang surge peptide biosystems Inc.
Example 1: preparation method of allergy-relieving repair composition
Preparation of acetoacetate derivatives: mixing acetoacetic acid ethyl ester, triethyl orthoformate and acetic anhydride, stirring at 110 ℃ for reaction for 2 hours, and distilling under reduced pressure to remove acetic anhydride after the reaction is completed to obtain the acetoacetic acid ethyl ester derivative. The amount of acetic anhydride used was 100g, the amount of acetoacetic acid ethyl ester used was 50g, and the amount of triethyl orthoformate used was 35g.
Preparation of S-substituent pyrimidine derivatives: adding S-carboxyethyl isothiourea chloride and an acetoacetic ester derivative into ethanol, regulating the pH to 9, stirring and reacting for 6 hours at 30 ℃, after the reaction is finished, performing rotary evaporation and concentration, performing ice bath treatment for 10 minutes, separating out solids, performing suction filtration, and collecting the solids to obtain the S-substituent pyrimidine derivative. The amount of ethanol used was 100g, the amount of acetoacetate derivative used was 40g, and the amount of S-carboxyethyl isothiourea chloride used was 32g.
Preparation of S-substituent pyrimidinyl carboxylic acid derivative: and adding the S-substituent pyrimidine derivative into a sodium hydroxide solution, heating to 60 ℃, stirring until the S-substituent pyrimidine derivative is fully dissolved, detecting the reaction by TLC, cooling, adjusting the pH to 2, precipitating a solid, and carrying out suction filtration to obtain the S-substituent pyrimidine carboxylic acid derivative. The concentration of the sodium hydroxide solution was 1mol/L, the amount of the sodium hydroxide solution used was 100g, and the amount of the S-substituted pyrimidine derivative used was 8g.
Preparation of a allergy-relieving repair composition: and compounding the S-substituent pyrimidinyl carboxylic acid derivative and hexapeptide-11 to obtain the allergy-relieving repair composition. S-substituent pyrimidinyl carboxylic acid derivative and hexapeptide-11 in mass ratio of 1: 1.
Example 2: preparation method of allergy-relieving repair composition
This example differs from example 1 in the preparation of a comfort repair composition.
Preparation of a allergy-relieving repair composition: and compounding the S-substituent pyrimidinyl carboxylic acid derivative and the decarboxylated carnosine to obtain the sulpiride repair composition. S-substituent pyrimidinyl carboxylic acid derivative and decarboxylated carnosine in a mass ratio of 1: 1.
Example 3: preparation method of allergy-relieving repair composition
This example differs from example 1 in the preparation of a comfort repair composition.
Preparation of a allergy-relieving repair composition: and compounding the S-substituent pyrimidinyl carboxylic acid derivative and the lactobacillus fermentation lysate to obtain the allergy-relieving repair composition. S-substituent pyrimidinyl carboxylic acid derivative and lactobacillus fermentation lysate in a mass ratio of 1: 1.
Example 4: preparation method of allergy-relieving repair composition
This example differs from example 1 in the preparation of a comfort repair composition.
Preparation of a allergy-relieving repair composition: and compounding the S-substituent pyrimidinyl carboxylic acid derivative, hexapeptide-11 and decarboxylated carnosine to obtain the allergy-relieving repair composition. S-substituent pyrimidinyl carboxylic acid derivative, hexapeptide-11 and decarboxylated carnosine in mass ratio of 1:1: 1.
Example 5: preparation method of allergy-relieving repair composition
This example differs from example 1 in the preparation of a comfort repair composition.
Preparation of a allergy-relieving repair composition: and compounding the S-substituent pyrimidinyl carboxylic acid derivative, hexapeptide-11 and lactobacillus fermentation lysate to obtain the allergy-relieving repair composition. S-substituent pyrimidinyl carboxylic acid derivative, hexapeptide-11 and lactobacillus fermentation lysate in mass ratio of 1:1: 1.
Example 6: preparation method of allergy-relieving repair composition
This example differs from example 1 in the preparation of a comfort repair composition.
Preparation of a allergy-relieving repair composition: and compounding the S-substituent pyrimidinyl carboxylic acid derivative, hexapeptide-11, decarboxylated carnosine and lactobacillus fermentation lysate to obtain the allergy-relieving repair composition. S-substituent pyrimidinyl carboxylic acid derivative, hexapeptide-11, decarboxylated carnosine and lactobacillus fermentation lysate in mass ratio of 1:1:1: 1.
Example 7: preparation method of allergy-relieving repair composition
This example differs from example 1 in the preparation of a comfort repair composition.
Preparation of a allergy-relieving repair composition: and compounding the S-substituent pyrimidinyl carboxylic acid derivative, hexapeptide-11 and propylene glycol oleate to obtain the allergy-relieving repair composition. S-substituent pyrimidinyl carboxylic acid derivative, hexapeptide-11 and propylene glycol oleate in mass ratio of 1:1: compounding in a ratio of 0.1.
Example 8: preparation method of allergy-relieving repair composition
This example differs from example 2 in the preparation of a comfort repair composition.
Preparation of a allergy-relieving repair composition: and compounding the S-substituent pyrimidinyl carboxylic acid derivative, the decarboxylated carnosine and the propylene glycol oleate to obtain the allergy-relieving repair composition. S-substituent pyrimidinyl carboxylic acid derivative, decarboxylated carnosine and propylene glycol oleate in a mass ratio of 1:1: compounding in a ratio of 0.1.
Example 9: preparation method of allergy-relieving repair composition
This example differs from example 3 in the preparation of a comfort repair composition.
Preparation of a allergy-relieving repair composition: and compounding the S-substituent pyrimidinyl carboxylic acid derivative, the lactobacillus fermentation lysate and propylene glycol oleate to obtain the allergy-relieving repair composition. S-substituent pyrimidinyl carboxylic acid derivative, lactobacillus fermentation lysate and propylene glycol oleate in mass ratio of 1:1: compounding in a ratio of 0.1.
Example 10: preparation method of allergy-relieving repair composition
This example differs from example 4 in the preparation of a comfort repair composition.
Preparation of a allergy-relieving repair composition: and compounding the S-substituent pyrimidinyl carboxylic acid derivative, hexapeptide-11, decarboxylated carnosine and propylene glycol oleate to obtain the allergy-relieving repair composition. S-substituent pyrimidinyl carboxylic acid derivative, hexapeptide-11, decarboxylated carnosine and propylene glycol oleate in mass ratio of 1:1:1: compounding in a ratio of 0.1.
Example 11: preparation method of allergy-relieving repair composition
This example differs from example 5 in the preparation of a comfort repair composition.
Preparation of a allergy-relieving repair composition: and compounding the S-substituent pyrimidinyl carboxylic acid derivative, hexapeptide-11, lactobacillus fermentation lysate and propylene glycol oleate to obtain the allergy-relieving repair composition. S-substituent pyrimidinyl carboxylic acid derivative, hexapeptide-11, lactobacillus fermentation lysate and propylene glycol oleate in mass ratio of 1:1:1: compounding in a ratio of 0.1.
Example 12: preparation method of allergy-relieving repair composition
This example differs from example 6 in the preparation of a comfort repair composition.
Preparation of a allergy-relieving repair composition: and compounding the S-substituent pyrimidinyl carboxylic acid derivative, hexapeptide-11, decarboxylated carnosine, lactobacillus fermentation lysate and propylene glycol oleate to obtain the allergy-relieving repair composition. S-substituent pyrimidinyl carboxylic acid derivative, hexapeptide-11, decarboxylated carnosine, lactobacillus fermentation lysate and propylene glycol oleate in mass ratio of 1:1:1:1: compounding in a ratio of 0.1.
Comparative example 1: preparation method of allergy-relieving repair composition
This comparative example differs from example 1 in the preparation of a comfort repair composition.
Preparation of a allergy-relieving repair composition: and compounding the S-substituent pyrimidine derivative and hexapeptide-11 to obtain the allergy-relieving repair composition. S-substituent pyrimidine derivative and hexapeptide-11 in mass ratio of 1: 1.
Test example:
the invention carries out infrared analysis on the S-substituent pyrimidinyl carboxylic acid derivative prepared in the example 1, and the result is shown in figure 1, wherein the S-substituent pyrimidinyl carboxylic acid derivative is between 3000 and 3500cm -1 An infrared absorption peak of a hydroxyl group at 1642cm -1 The infrared absorption peak of carbonyl is 1578cm -1 Is the infrared absorption peak of carbon-nitrogen bond on pyrimidine ring.
The invention adopts S-substituent pyrimidinyl carboxylic acid derivative prepared in the example 1 to carry out cytotoxicity test, HK-2 cells are adopted in the test, the HK-2 cells are cultivated by adopting the prior method, the HK-2 cell culture medium is DMEM culture medium containing 10% fetal bovine serum and 1% double antibody (penicillin 10000U/mL and streptomycin 10 mg/mL), the cultivated HK-2 cells are digested and then are prepared into cell suspension by adopting the DMEM culture medium, and 1 multiplied by 10 is inoculated on a 96-well plate 4 Cells/100. Mu.L, one round of PBS buffer solution is added outside the 96-well plate, the cells are cultured for 24 hours, then the culture medium is removed, then DMEM culture medium containing 5wt% of S-substituted pyrimidinyl carboxylic acid derivative is added, the culture medium is incubated in an incubator for 48 hours, then DMEM culture medium containing 10% of CCK-8 is added under dark condition, after the culture is carried out for 1 hour, absorbance at 450nm is measured by an enzyme-labeling instrument, and cell viability is calculated, wherein, C is a test group using S-substituted pyrimidinyl carboxylic acid derivative, D is a control group not using S-substituted pyrimidinyl carboxylic acid derivative, and the S-substituted pyrimidinyl carboxylic acid derivative prepared by the invention is found to be basically free of cytotoxicity by comparing the test group with the control group.
TABLE 1 cell survival
The invention carries out skin percutaneous water loss rate (TEWL) test in volunteers with the age of 18-60 years meeting the experimental requirements, the test condition is 25 ℃, the relative humidity is 50%, and the real-time dynamic monitoring is carried out, the test samples are prepared into test samples with the concentration of 20mg/L by the comfort repair composition of each example and the comparative example in water, the test samples of the example are smeared on the left face of the volunteers, the test samples of the comparative example are smeared on the right face, the skin percutaneous water loss rate of the volunteers is taken as an initial value when the test is started, the test samples of the example or the comparative example are used twice a day in the morning and evening, the skin percutaneous water loss rate is recorded as a test value after 30D, the delta TEWL is obtained by subtracting the initial value of the skin percutaneous water loss rate from the test value of the skin percutaneous water loss rate, the delta TEWL is a negative value, the value is lower, the test results are shown in FIG. 2, wherein 1 is example 1, S2 is example 2, S3 is example 3, S4 is example 4, S5 is example 5, S6 is example 6, S7 is example 7, S8 is example 8, S9 is example 9, S10 is example 10, S11 is example 11, S12 is example 12, D1 is comparative example 1, the sulbactam composition of the invention contains at least S-substituent pyrimidinylcarboxylic acid derivative, and at least 1 of hexapeptide-11, decarboxylated carnosine and lactobacillus fermentation lysate can be contained in the preparation of S-substituent pyrimidinylcarboxylic acid derivative, the acetoacetate and triethyl orthoformate are reacted to prepare acetoacetate derivative, s-substituent pyrimidine derivatives are prepared from S-carboxyethyl isothiourea chloride and acetoacetic ester derivatives, S-substituent pyrimidine derivatives are prepared from S-substituent pyrimidine derivatives under alkaline conditions and acidic conditions, after the S-substituent pyrimidine carboxylic acid derivatives are prepared into a sulpirimic restoration composition according to the method, the combination of the S-substituent pyrimidine carboxylic acid derivatives and any one of hexapeptide-11, decarboxylated carnosine and lactobacillus fermentation lysate can reduce the water loss of skin, and after the S-substituent pyrimidine carboxylic acid derivatives are replaced by the S-substituent pyrimidine derivatives, the sulpirimic restoration composition formed by the S-substituent pyrimidine carboxylic acid derivatives cannot effectively reduce the water loss of skin, and the combination of the S-substituent pyrimidine carboxylic acid derivatives and lactobacillus fermentation lysate is superior to the combination of the S-substituent pyrimidine carboxylic acid derivatives and hexapeptide-11, the combination of the S-substituent pyrimidine carboxylic acid derivatives and lactobacillus fermentation lysate is superior to the combination of the S-substituent pyrimidine carboxylic acid derivatives and the decarboxylated carnosine, and the sulpirimic acid derivatives can be further compounded into a plurality of sulpirimic acid derivatives; furthermore, propylene glycol oleate can be added into the comfort restoration composition, and the use effect of the comfort restoration composition can be further improved.
The above embodiments are merely for illustrating the present invention and not for limiting the same, and various changes and modifications may be made by one of ordinary skill in the art without departing from the spirit and scope of the invention. Therefore, all equivalent technical solutions are also within the scope of the present invention, which is defined by the claims.
Claims (9)
- A process for the preparation of s-substituted pyrimidinyl carboxylic acid derivatives comprising: the method comprises the steps of reacting acetoacetic acid ethyl ester with triethyl orthoformate to obtain acetoacetic acid ethyl ester derivative, reacting S-carboxyethyl isothiourea chloride with the acetoacetic acid ethyl ester derivative to obtain S-substituent pyrimidine derivative, and finally preparing the S-substituent pyrimidine carboxylic acid derivative from the S-substituent pyrimidine derivative through alkali treatment and acid treatment, wherein an alkaline reagent in the alkali treatment is sodium hydroxide solution with the concentration of 0.5-2mol/L, and the pH value of the acid treatment is 2-3.
- 2. The process for producing an S-substituted pyrimidinyl carboxylic acid derivative according to claim 1, characterized in that: the usage amount of the triethyl orthoformate is 60-80wt% of that of the acetoacetic acid ethyl ester; or the S-carboxyethyl isothiourea chloride is used in an amount of 70-90wt% of the acetoacetic acid ethyl ester derivative.
- 3. The process for producing an S-substituted pyrimidinyl carboxylic acid derivative according to claim 2, characterized in that: the temperature of the alkali treatment is 40-70 ℃.
- 4. The process for producing an S-substituted pyrimidinyl carboxylic acid derivative according to claim 1, characterized in that: the preparation solvent of the acetoacetic acid ethyl ester derivative is acetic anhydride; or, the solvent for preparing the S-substituent pyrimidine derivative is ethanol.
- 5. A sulpirimic repair composition comprising at least the S-substituted pyrimidinyl carboxylic acid derivative prepared by the method of claim 1, further comprising at least 1 of hexapeptide-11, decarboxylated carnosine and lactobacillus fermentation lysate.
- 6. A comfort repair composition according to claim 5, characterized in that: the S-substituent pyrimidinyl carboxylic acid derivative and hexapeptide-11 are in a mass ratio of 1: mixing at a ratio of 0.1-10; or, the S-substituent pyrimidinyl carboxylic acid derivative and decarboxylated carnosine are mixed according to the mass ratio of 1: mixing at a ratio of 0.1-10; or, the S-substituent pyrimidinyl carboxylic acid derivative and lactobacillus fermentation lysate are mixed according to the mass ratio of 1: mixing at a ratio of 0.1-10.
- 7. Use of a allergy-relieving restoration composition according to claim 5 in the preparation of a cosmetic.
- 8. A method of preparing a allergy-relieving repair composition comprising: a process for producing an S-substituted pyrimidinyl carboxylic acid derivative according to claim 1.
- 9. The method for preparing the allergy-relieving repair composition according to claim 8, wherein the method comprises the following steps: the S-substituent pyrimidinyl carboxylic acid derivative is mixed with at least 1 of hexapeptide-11, decarboxylated carnosine and lactobacillus fermentation lysate to prepare the sulpirome restoration composition.
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