CN112300228A - A cosmetic containing phloretin derivative containing phloroglucinol group and its preparation method - Google Patents
A cosmetic containing phloretin derivative containing phloroglucinol group and its preparation method Download PDFInfo
- Publication number
- CN112300228A CN112300228A CN202011196901.4A CN202011196901A CN112300228A CN 112300228 A CN112300228 A CN 112300228A CN 202011196901 A CN202011196901 A CN 202011196901A CN 112300228 A CN112300228 A CN 112300228A
- Authority
- CN
- China
- Prior art keywords
- phloretin
- aminotriacetylglucoside
- sodium
- modified
- hydroxyphenylpropionate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- VGEREEWJJVICBM-UHFFFAOYSA-N phloretin Chemical class C1=CC(O)=CC=C1CCC(=O)C1=C(O)C=C(O)C=C1O VGEREEWJJVICBM-UHFFFAOYSA-N 0.000 title claims abstract description 112
- 239000002537 cosmetic Substances 0.000 title claims abstract description 26
- 238000002360 preparation method Methods 0.000 title claims abstract description 22
- 125000002444 phloroglucinyl group Chemical group [H]OC1=C([H])C(O[H])=C(*)C(O[H])=C1[H] 0.000 title claims abstract description 18
- ZWTDXYUDJYDHJR-UHFFFAOYSA-N (E)-1-(2,4-dihydroxyphenyl)-3-(2,4-dihydroxyphenyl)-2-propen-1-one Natural products OC1=CC(O)=CC=C1C=CC(=O)C1=CC=C(O)C=C1O ZWTDXYUDJYDHJR-UHFFFAOYSA-N 0.000 claims abstract description 34
- YQHMWTPYORBCMF-UHFFFAOYSA-N Naringenin chalcone Natural products C1=CC(O)=CC=C1C=CC(=O)C1=C(O)C=C(O)C=C1O YQHMWTPYORBCMF-UHFFFAOYSA-N 0.000 claims abstract description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 23
- -1 phloroglucinol Chemical compound 0.000 claims abstract description 22
- 238000006243 chemical reaction Methods 0.000 claims abstract description 13
- 229930182478 glucoside Natural products 0.000 claims abstract description 10
- 150000008131 glucosides Chemical class 0.000 claims abstract description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 10
- JPYHHZQJCSQRJY-UHFFFAOYSA-N Phloroglucinol Natural products CCC=CCC=CCC=CCC=CCCCCC(=O)C1=C(O)C=C(O)C=C1O JPYHHZQJCSQRJY-UHFFFAOYSA-N 0.000 claims abstract description 8
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229960001553 phloroglucinol Drugs 0.000 claims abstract description 8
- XLARGVYTESPBAK-UHFFFAOYSA-M sodium;2-(4-hydroxyphenyl)propanoate Chemical compound [Na+].[O-]C(=O)C(C)C1=CC=C(O)C=C1 XLARGVYTESPBAK-UHFFFAOYSA-M 0.000 claims description 29
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 27
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 27
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 18
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 18
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 claims description 18
- 239000006071 cream Substances 0.000 claims description 16
- 239000000047 product Substances 0.000 claims description 14
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 claims description 12
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- 239000008367 deionised water Substances 0.000 claims description 9
- 229910021641 deionized water Inorganic materials 0.000 claims description 9
- 238000005406 washing Methods 0.000 claims description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- 230000001815 facial effect Effects 0.000 claims description 8
- 239000007787 solid Substances 0.000 claims description 8
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 6
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 6
- 239000004166 Lanolin Substances 0.000 claims description 6
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 6
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 claims description 6
- 239000005457 ice water Substances 0.000 claims description 6
- 235000019388 lanolin Nutrition 0.000 claims description 6
- 229940039717 lanolin Drugs 0.000 claims description 6
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 6
- 239000012074 organic phase Substances 0.000 claims description 6
- 239000000243 solution Substances 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 6
- LADGBHLMCUINGV-UHFFFAOYSA-N tricaprin Chemical compound CCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCC)COC(=O)CCCCCCCCC LADGBHLMCUINGV-UHFFFAOYSA-N 0.000 claims description 6
- CUNWUEBNSZSNRX-RKGWDQTMSA-N (2r,3r,4r,5s)-hexane-1,2,3,4,5,6-hexol;(z)-octadec-9-enoic acid Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.CCCCCCCC\C=C/CCCCCCCC(O)=O.CCCCCCCC\C=C/CCCCCCCC(O)=O.CCCCCCCC\C=C/CCCCCCCC(O)=O CUNWUEBNSZSNRX-RKGWDQTMSA-N 0.000 claims description 3
- MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 3
- 108010010803 Gelatin Proteins 0.000 claims description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 3
- 229920002125 Sokalan® Polymers 0.000 claims description 3
- MNZMECMQTYGSOI-UHFFFAOYSA-N acetic acid;hydron;bromide Chemical compound Br.CC(O)=O MNZMECMQTYGSOI-UHFFFAOYSA-N 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 235000010323 ascorbic acid Nutrition 0.000 claims description 3
- 229960005070 ascorbic acid Drugs 0.000 claims description 3
- 239000011668 ascorbic acid Substances 0.000 claims description 3
- 235000013871 bee wax Nutrition 0.000 claims description 3
- 239000012166 beeswax Substances 0.000 claims description 3
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 claims description 3
- 229960001631 carbomer Drugs 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 230000003197 catalytic effect Effects 0.000 claims description 3
- 229960000541 cetyl alcohol Drugs 0.000 claims description 3
- 239000012065 filter cake Substances 0.000 claims description 3
- 239000000706 filtrate Substances 0.000 claims description 3
- 239000008273 gelatin Substances 0.000 claims description 3
- 229920000159 gelatin Polymers 0.000 claims description 3
- 235000019322 gelatine Nutrition 0.000 claims description 3
- 235000011852 gelatine desserts Nutrition 0.000 claims description 3
- 229960002442 glucosamine Drugs 0.000 claims description 3
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 claims description 3
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 claims description 3
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims description 3
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 claims description 3
- 229940057995 liquid paraffin Drugs 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 125000001312 palmitoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 239000012071 phase Substances 0.000 claims description 3
- 239000001818 polyoxyethylene sorbitan monostearate Substances 0.000 claims description 3
- 235000010989 polyoxyethylene sorbitan monostearate Nutrition 0.000 claims description 3
- 229920001184 polypeptide Polymers 0.000 claims description 3
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 3
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 229960005078 sorbitan sesquioleate Drugs 0.000 claims description 3
- 238000000967 suction filtration Methods 0.000 claims description 3
- ASJFVAVKAMMVFI-XJFOESAGSA-N Br[C@@]([C@]([C@@]([C@](C(=O)C(C)=O)(O)C(C)=O)(O)C(C)=O)(O)C(C)=O)(O)CO Chemical compound Br[C@@]([C@]([C@@]([C@](C(=O)C(C)=O)(O)C(C)=O)(O)C(C)=O)(O)C(C)=O)(O)CO ASJFVAVKAMMVFI-XJFOESAGSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 3
- 239000006210 lotion Substances 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 abstract description 6
- 230000000694 effects Effects 0.000 abstract description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 4
- 230000037384 skin absorption Effects 0.000 abstract description 4
- 231100000274 skin absorption Toxicity 0.000 abstract description 4
- NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical compound OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 abstract 1
- 239000002994 raw material Substances 0.000 abstract 1
- 230000002194 synthesizing effect Effects 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 11
- 230000003078 antioxidant effect Effects 0.000 description 8
- 238000010521 absorption reaction Methods 0.000 description 5
- 239000000499 gel Substances 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 230000005764 inhibitory process Effects 0.000 description 4
- 239000003963 antioxidant agent Substances 0.000 description 3
- 235000006708 antioxidants Nutrition 0.000 description 3
- 239000000686 essence Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 235000015097 nutrients Nutrition 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 235000013824 polyphenols Nutrition 0.000 description 3
- 201000004624 Dermatitis Diseases 0.000 description 2
- 240000001307 Myosotis scorpioides Species 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 235000016709 nutrition Nutrition 0.000 description 2
- 230000035764 nutrition Effects 0.000 description 2
- 238000011056 performance test Methods 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 230000000638 stimulation Effects 0.000 description 2
- 230000008961 swelling Effects 0.000 description 2
- NNWKGXBQNBUTTJ-UHFFFAOYSA-N 2-hydroxy-1-phenyl-3-(4,4,6-trihydroxycyclohexa-1,5-dien-1-yl)propan-1-one Chemical compound OC(C(=O)C1=CC=CC=C1)CC1=CCC(C=C1O)(O)O NNWKGXBQNBUTTJ-UHFFFAOYSA-N 0.000 description 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 208000002874 Acne Vulgaris Diseases 0.000 description 1
- 206010014025 Ear swelling Diseases 0.000 description 1
- 244000141359 Malus pumila Species 0.000 description 1
- 241000220324 Pyrus Species 0.000 description 1
- 206010000496 acne Diseases 0.000 description 1
- 235000021016 apples Nutrition 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229930003935 flavonoid Natural products 0.000 description 1
- 150000002215 flavonoids Chemical class 0.000 description 1
- 235000017173 flavonoids Nutrition 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 235000021017 pears Nutrition 0.000 description 1
- 239000012466 permeate Substances 0.000 description 1
- 239000011505 plaster Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 235000015192 vegetable juice Nutrition 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/203—Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/60—Sugars; Derivatives thereof
- A61K8/602—Glycosides, e.g. rutin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/08—Anti-ageing preparations
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Dermatology (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Gerontology & Geriatric Medicine (AREA)
- Birds (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Rheumatology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pain & Pain Management (AREA)
- Cosmetics (AREA)
Abstract
The invention provides a preparation method of a phloretin derivative containing a phloroglucinol group, which is a phloretin modified by amino triacetyl glucoside, wherein hydroxyl in p-hydroxy-phenyl propionic acid in raw materials for synthesizing the phloretin is subjected to modified grafting in advance, and then is subjected to synthetic reaction with phloroglucinol, namely phloroglucinol, so that the corresponding phloretin derivative containing the phloroglucinol group and the corresponding phloretin modified by the amino triacetyl glucoside are obtained. The derivative not only retains the inoxidizability and the anti-inflammation of the phloretin, but also has good water solubility and skin absorption efficiency, so that the obtained phloretin derivative can be widely applied to various forms of cosmetic products and has excellent inoxidizability and anti-inflammation effects.
Description
Technical Field
The invention relates to the field of cosmetics, in particular to a cosmetic containing phloretin derivatives containing phloroglucinol groups and a preparation method thereof.
Background
The cosmetic is a product which is applied to the surface part of a human body in a smearing or other similar mode so as to achieve the effects of cleaning, maintaining, beautifying and the like on the surface part. At present, the cosmetics on the market are various in variety, and among them, cosmetics for relieving skin inflammation, resisting oxidation and resisting aging are most favored by women.
Phloretin, namely 2,4, 6-trihydroxy-3- (4-hydroxyphenyl) propiophenone, is a flavonoid natural compound which is mainly distributed in the peel and root bark of juicy fruits such as apples and pears and various vegetable juices. The effects of phloretin in whitening skin, removing acne, resisting oxidation and resisting inflammation are attributed to the 2,4, 6-trihydroxy group in phloretin molecules, namely phloroglucinol group or phloroglucinol group.
However, when the phloretin is added into a formula as a functional component and directly coated on the surface of human skin, solid powder is easily formed and adhered to the skin, stimulation to the skin is likely to be generated, and medicines cannot effectively permeate the surface of the skin and reach a blood circulation system, so that the skin anti-inflammatory effect of the phloretin is greatly limited. Moreover, the water solubility of the phloretin is poor, the absorption utilization rate of the phloretin by the human skin is relatively low, and even if the preparation or the composition containing the phloretin is prepared into the temperature-sensitive gel, the action time of the phloretin on the surface of the human skin can be prolonged, but the absorption efficiency of the human skin on the phloretin cannot be fundamentally improved.
Phloretin can be modified to improve its anti-inflammatory, antioxidant and skin absorption efficiency. However, the active groups which are easily modified and grafted in the phloretin molecule are mainly phenolic hydroxyl groups, so that the phloretin is directly modified, and the phenolic hydroxyl groups, particularly phloroglucinol groups, in the phloretin molecule are easily damaged, so that the oxidation resistance and the anti-inflammation performance of the modified phloretin derivative are reduced, and the application of the modified phloretin derivative in cosmetics is not facilitated.
Therefore, the technical report that the preparation or the composition containing the phloretin is prepared into the temperature-sensitive gel, so that the temperature-sensitive gel keeps a semi-solid state continuously in the using process, the acting time of the phloretin on the surface of human skin is prolonged, the absorption degree of the human skin on the phloretin is improved, and the temperature-sensitive gel has a good anti-inflammatory effect. However, the application diversity of phloretin is limited by the gel preparation.
Meanwhile, the method does not fundamentally solve the problems of poor water solubility and low skin absorption efficiency of phloretin.
Therefore, the invention aims to modify phloretin on the basis of keeping phloretin triphenol groups in phloretin molecules through modifying research on the phloretin, so that the water solubility of the phloretin derivative can be improved while the anti-inflammatory and anti-oxygen properties of the phloretin derivative are ensured, the absorption efficiency of human skin on the phloretin derivative can be improved, the application diversity of cosmetics containing the phloretin derivative is enriched, and the effects of relieving skin inflammation, resisting oxidation and resisting aging of the cosmetics containing the phloretin derivative are improved.
Disclosure of Invention
In order to solve the problems of the existing phloretin-containing cosmetics, the invention provides a phloretin derivative containing phloroglucinol groups, a preparation method thereof and cosmetics containing the phloretin derivative.
A preparation method of a phloretin derivative containing a phloroglucinol group is disclosed, wherein the phloretin derivative containing the phloroglucinol group is modified by amino triacetyl glucoside, and the preparation method comprises the following steps:
(1) preparation of bromoamino triacetyl glucose
Adding glucosamine into acetic anhydride with 3-5 times of molar weight, dropwise adding triethylamine with 5-6 times of molar weight under the condition of ice-water bath, reacting for 2 hours, adding enough water to precipitate a product, filtering, washing a filter cake with water, and drying in vacuum to obtain aminotetraacetylglucose; dissolving dried aminotetraacetylglucose in dichloromethane, dropwise adding hydrobromic acid with 2.5-4 times of molar weight of aminotetraacetylglucose at normal temperature, wherein the hydrobromic acid is provided by hydrobromic acid acetic acid solution with mass concentration of 30%, reacting for 1.5-3 hours, pouring into ice water, extracting a water phase by dichloromethane, combining organic phases, rapidly washing the organic phase by saturated sodium bicarbonate solution and saturated saline solution respectively until the pH value is 7, drying anhydrous magnesium sulfate, filtering, distilling the filtrate at normal temperature under reduced pressure to recover dichloromethane, and obtaining bromoaminotriacetylglucose product.
(2) Preparation of sodium p-hydroxyphenylpropionate aminotriacetylglucoside
Mixing and adding aqueous solutions of sodium p-hydroxyphenylpropionate, sodium hydroxide and potassium iodide into a reaction container, stirring at room temperature for reaction, wherein the concentration of the sodium p-hydroxyphenylpropionate is 0.2-0.5mol/L, the concentration of the sodium hydroxide is 20-50g/L, and the concentration of the potassium iodide is 1-3g/L, then dropwise adding bromoaminotriacetylglucose dissolved in acetone into the reaction container, stirring at room temperature for reaction for 6-8 hours, separating out a solid, namely sodium p-hydroxyphenylpropionate aminotriacetylglucoside, and sequentially washing with sodium hydroxide and deionized water after suction filtration to obtain the solid sodium p-hydroxyphenylpropionate aminotriacetylglucoside.
(3) Preparation of phloretin modified by amino triacetyl glucoside
Dissolving sodium p-hydroxyphenylpropionate aminotriacetylglucoside, acetic acid and phloroglucinol in an ethyl acetate solvent, reacting for 4-8 hours under the catalytic action of boron trifluoride diethyl etherate to obtain the aminotriacetylglucoside modified phloretin shown in the formula (I), and distilling and separating to obtain the aminotriacetylglucoside modified phloretin product.
Wherein, the molar ratio of the sodium p-hydroxyphenylpropionate aminotriacetylglucoside to the acetic acid to the phloroglucinol is 1 (1.5-2) to 1.5-2. Wherein, in the step (2), the ratio of the molar amount of the bromoaminotriacetylglucose to the molar amount of the sodium p-hydroxyphenylpropionate which is dripped is (1.2-1.5):1, thereby improving the yield of the sodium p-hydroxyphenylpropionate aminotriacetylglucoside.
Wherein in the step (3), the amount of boron trifluoride diethyl etherate as a catalyst is 1-5g based on 1 mol of sodium p-hydroxyphenylpropionate aminotriacetylglucoside.
The phloretin modified by the amino triacetyl glucoside synthesized by the invention reserves the phloroglucinol group therein, and ensures the inoxidizability and the anti-inflammation of the phloretin modified by the amino triacetyl glucoside. Meanwhile, an aminotriacetylglucoside group is grafted and introduced on a phenolic hydroxyl group of the 4-hydroxyphenyl group, so that the water solubility and the skin absorption efficiency of the phloretin derivative are improved, the obtained phloretin derivative can be widely applied to various forms of cosmetic products, and has excellent oxidation resistance and anti-inflammatory effects.
A cosmetic containing an aminotriacetylglucoside-modified phloretin, which is characterized in that: the content of the aminotriacetylglucoside modified phloretin is 1-3 wt.%.
Further, the cosmetic is one of nourishing cream, facial mask, cream, skin moistening cream, essence, cream and plaster. Further, the cosmetic is a nourishing cream, and the nourishing cream comprises the following components in percentage by weight:
1-3% of aminotriacetylglucoside modified phloretin, 1-2% of hydrogenated lanolin, 0.5-2% of polyoxyethylene sorbitan monostearate, 6-8% of beeswax, 1-2% of cetyl alcohol, 2-4% of caprylic/capric triglyceride, 6-10% of glycerol, 3-4% of liquid paraffin, 0.1-0.5% of triethanolamine, 0.1-0.2% of essence and the balance of deionized water.
Further, the cosmetic is a facial mask, and the facial mask comprises the following components in percentage by weight:
1-3% of aminotriacetylglucoside modified phloretin, 0.2-1% of carbomer, 0.3-0.5% of triethanolamine, 2-3% of ascorbic acid polypeptide, 43-5% of palmitoyl pentapeptide, 8-12% of glycerol, 2-4% of hydroxypropyl methyl cellulose, 3-5% of propylene glycol, 2-4% of hydrolyzed gelatin, 1-2% of sorbitan sesquioleate, 1-2% of hydrogenated lanolin, 2-4% of caprylic/capric triglyceride and the balance of deionized water.
Detailed Description
The present invention will be described below with reference to specific examples, but these are not intended to be all the invention. Firstly, preparing the phloretin derivative containing the phloroglucinol group according to the following preparation method, wherein the phloretin derivative containing the phloroglucinol group is phloretin modified by amino triacetyl glucoside:
(1) preparation of bromotetraacetylglucose
Adding glucosamine into acetic anhydride with 3-5 times of molar weight, dropwise adding triethylamine with 5-6 times of molar weight under the condition of ice-water bath, reacting for 2 hours, adding enough water to precipitate a product, filtering, washing a filter cake with water, and drying in vacuum to obtain aminotetraacetylglucose; dissolving dried aminotetraacetylglucose in dichloromethane, dropwise adding hydrobromic acid with 2.5-4 times of molar weight of aminotetraacetylglucose at normal temperature, wherein the hydrobromic acid is provided by hydrobromic acid acetic acid solution with mass concentration of 30%, reacting for 1.5-3 hours, pouring into ice water, extracting a water phase by dichloromethane, combining organic phases, rapidly washing the organic phase by saturated sodium bicarbonate solution and saturated saline solution respectively until the pH value is 7, drying anhydrous magnesium sulfate, filtering, distilling the filtrate at normal temperature under reduced pressure to recover dichloromethane, and obtaining bromoaminotriacetylglucose product.
(2) Preparation of sodium p-hydroxyphenylpropionate aminotriacetylglucoside
Mixing and adding aqueous solutions of sodium p-hydroxyphenylpropionate, sodium hydroxide and potassium iodide into a reaction container, stirring at room temperature for reaction, wherein the concentration of the sodium p-hydroxyphenylpropionate is 0.2-0.5mol/L, the concentration of the sodium hydroxide is 20-50g/L, and the concentration of the potassium iodide is 1-3g/L, then dropwise adding bromoaminotriacetylglucose dissolved in acetone into the reaction container, stirring at room temperature for reaction for 6-8 hours, separating out a solid, namely sodium p-hydroxyphenylpropionate aminotriacetylglucoside, and sequentially washing with sodium hydroxide and deionized water after suction filtration to obtain the solid sodium p-hydroxyphenylpropionate aminotriacetylglucoside.
(3) Preparation of phloretin modified by amino triacetyl glucoside
Dissolving sodium p-hydroxyphenylpropionate aminotriacetylglucoside, acetic acid and phloroglucinol in an ethyl acetate solvent, reacting for 4-8 hours under the catalytic action of boron trifluoride diethyl etherate to obtain the aminotriacetylglucoside modified phloretin shown in the formula (I), and distilling and separating to obtain the aminotriacetylglucoside modified phloretin product.
Wherein the molar ratio of the sodium p-hydroxyphenylpropionate aminotriacetylglucoside to the acetic acid to the phloroglucinol is 1:1.5: 1.5; in the step (2), the ratio of the molar weight of the dropwise added bromoaminotriacetylglucose to the molar weight of the sodium p-hydroxyphenylpropionate is 1.3: 1; in the step (3), the amount of boron trifluoride diethyl etherate as a catalyst is 3g based on 1 mol of sodium p-hydroxyphenylpropionate aminotriacetylglucoside.
Then, according to the following component requirements, the prepared aminotriacetylglucoside modified phloretin is added into a nutrition cream and a facial mask product to prepare the corresponding nutrition cream and facial mask product.
The nutrient cream comprises the following components in percentage by weight:
1-3% of aminotriacetylglucoside modified phloretin, 1-2% of hydrogenated lanolin, 0.5-2% of polyoxyethylene sorbitan monostearate, 6-8% of beeswax, 1-2% of cetyl alcohol, 2-4% of caprylic/capric triglyceride, 6-10% of glycerol, 3-4% of liquid paraffin, 0.1-0.5% of triethanolamine, 0.1-0.2% of essence and the balance of deionized water.
The mask comprises the following components in percentage by weight:
1-3% of aminotriacetylglucoside modified phloretin, 0.2-1% of carbomer, 0.3-0.5% of triethanolamine, 2-3% of ascorbic acid polypeptide, 43-5% of palmitoyl pentapeptide, 8-12% of glycerol, 2-4% of hydroxypropyl methyl cellulose, 3-5% of propylene glycol, 2-4% of hydrolyzed gelatin, 1-2% of sorbitan sesquioleate, 1-2% of hydrogenated lanolin, 2-4% of caprylic/capric triglyceride and the balance of deionized water.
Specifically, specific compositions of the respective examples and performance test results thereof are given in tables 1 and 2. The performance tests include, among others, an antioxidant test, an anti-inflammatory test, and a user experience evaluation.
The antioxidant test comprises DPPH free radical inhibition rate, OH free radical inhibition rate and O2-The inhibition rate of free radicals is three aspects. The anti-inflammation test adopts a mouse ear swelling experiment to carry out test, corresponding nutrient cream and facial mask liquid are directly smeared on the red swelling part of the mouse ear, the nutrient cream and the facial mask liquid are smeared according to the smearing dosage of 100mg/Kg of body weight based on the mass of the aminotriacetylglucoside modified phloretin, and then the swelling inhibition rate is calculated.
The user experience evaluation criteria are:
and 3, dividing: comfortable, and has good anti-inflammatory and antioxidant effects.
And 2, dividing: more comfortable, and has general anti-inflammatory and antioxidant effects.
1 minute: more comfortable, and has no obvious anti-inflammatory and antioxidant effects.
0 minute: discomfort and unobvious anti-inflammatory and antioxidant effects.
TABLE 1
TABLE 2
As can be seen from table 1 and table 2 above, the aminotriacetylglucoside modified phloretin of the present invention has excellent anti-inflammatory and antioxidant effects when applied to cosmetics. And the actual user experience is comfortable, the effect is obvious, and the corresponding product has high absorption rate on the skin surface and has no sensitive stimulation.
Claims (8)
1. A preparation method of a phloretin derivative containing a phloroglucinol group is disclosed, wherein the phloretin derivative containing the phloroglucinol group is modified by amino triacetyl glucoside, and the preparation method comprises the following steps:
(1) preparation of bromotetraacetylglucose
Adding glucosamine into acetic anhydride with 3-5 times of molar weight, dropwise adding triethylamine with 5-6 times of molar weight under the condition of ice-water bath, reacting for 2 hours, adding enough water to precipitate a product, filtering, washing a filter cake with water, and drying in vacuum to obtain aminotetraacetylglucose; dissolving dried aminotetraacetylglucose in dichloromethane, dropwise adding hydrobromic acid with 2.5-4 times of molar weight of aminotetraacetylglucose at normal temperature, wherein the hydrobromic acid is provided by hydrobromic acid acetic acid solution with mass concentration of 30%, reacting for 1.5-3 hours, pouring into ice water, extracting a water phase by dichloromethane, combining organic phases, rapidly washing the organic phase by saturated sodium bicarbonate solution and saturated saline solution respectively until the pH value is 7, drying anhydrous magnesium sulfate, filtering, distilling the filtrate at normal temperature under reduced pressure to recover dichloromethane, and obtaining bromoaminotriacetylglucose product.
(2) Preparation of sodium p-hydroxyphenylpropionate aminotriacetylglucoside
Mixing and adding aqueous solutions of sodium p-hydroxyphenylpropionate, sodium hydroxide and potassium iodide into a reaction container, stirring at room temperature for reaction, wherein the concentration of the sodium p-hydroxyphenylpropionate is 0.2-0.5mol/L, the concentration of the sodium hydroxide is 20-50g/L, and the concentration of the potassium iodide is 1-3g/L, then dropwise adding bromoaminotriacetylglucose dissolved in acetone into the reaction container, stirring at room temperature for reaction for 6-8 hours, separating out a solid, namely sodium p-hydroxyphenylpropionate aminotriacetylglucoside, and sequentially washing with sodium hydroxide and deionized water after suction filtration to obtain the solid sodium p-hydroxyphenylpropionate aminotriacetylglucoside.
(3) Preparation of phloretin modified by amino triacetyl glucoside
Dissolving sodium p-hydroxyphenylpropionate aminotriacetylglucoside, acetic acid and phloroglucinol in an ethyl acetate solvent, reacting for 4-8 hours under the catalytic action of boron trifluoride diethyl etherate to obtain the aminotriacetylglucoside modified phloretin shown in the formula (I), and distilling and separating to obtain the aminotriacetylglucoside modified phloretin product.
Wherein, the molar ratio of the sodium p-hydroxyphenylpropionate aminotriacetylglucoside to the acetic acid to the phloroglucinol is 1 (1.5-2) to 1.5-2.
2. The method for producing a phloretin derivative having a phloroglucinol group according to claim 1, comprising: in the step (2), the ratio of the molar amount of the bromoaminotriacetylglucose to the molar amount of the sodium p-hydroxyphenylpropionate added dropwise is (1.2-1.5):1, so that the yield of the sodium p-hydroxyphenylpropionate aminotriacetylglucoside can be improved.
3. The method for producing a phloretin derivative having a phloroglucinol group according to claim 1, comprising: in the step (3), the amount of boron trifluoride diethyl etherate as a catalyst is 1-5g based on 1 mol of sodium p-hydroxyphenylpropionate aminotriacetylglucoside.
4. An aminotriacetylglucoside-modified phloretin, which is produced by the production method according to any one of claims 1 to 3.
5. A cosmetic comprising the aminotriacetylglucoside-modified phloretin according to claim 4, wherein: the content of the aminotriacetylglucoside modified phloretin is 1-3 wt.%.
6. The cosmetic of claim 5, wherein the cosmetic is one of a nourishing cream, a facial mask, a cream, a skin lotion, an essence, a cream, and a patch.
7. The cosmetic according to claim 6, wherein the cosmetic is a nourishing cream, and the nourishing cream comprises the following components in percentage by weight:
1-3% of aminotriacetylglucoside modified phloretin, 1-2% of hydrogenated lanolin, 0.5-2% of polyoxyethylene sorbitan monostearate, 6-8% of beeswax, 1-2% of cetyl alcohol, 2-4% of caprylic/capric triglyceride, 6-10% of glycerol, 3-4% of liquid paraffin, 0.1-0.5% of triethanolamine, 0.1-0.2% of essence and the balance of deionized water.
8. The cosmetic according to claim 6, wherein the cosmetic is a mask, and the mask comprises the following components in percentage by weight:
1-3% of aminotriacetylglucoside modified phloretin, 0.2-1% of carbomer, 0.3-0.5% of triethanolamine, 2-3% of ascorbic acid polypeptide, 43-5% of palmitoyl pentapeptide, 8-12% of glycerol, 2-4% of hydroxypropyl methyl cellulose, 3-5% of propylene glycol, 2-4% of hydrolyzed gelatin, 1-2% of sorbitan sesquioleate, 1-2% of hydrogenated lanolin, 2-4% of caprylic/capric triglyceride and the balance of deionized water.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202011196901.4A CN112300228A (en) | 2020-10-31 | 2020-10-31 | A cosmetic containing phloretin derivative containing phloroglucinol group and its preparation method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202011196901.4A CN112300228A (en) | 2020-10-31 | 2020-10-31 | A cosmetic containing phloretin derivative containing phloroglucinol group and its preparation method |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN112300228A true CN112300228A (en) | 2021-02-02 |
Family
ID=74333188
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202011196901.4A Pending CN112300228A (en) | 2020-10-31 | 2020-10-31 | A cosmetic containing phloretin derivative containing phloroglucinol group and its preparation method |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN112300228A (en) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006002422A2 (en) * | 2004-06-24 | 2006-01-05 | Novartis Vaccines And Diagnostics Inc. | Compounds for immunopotentiation |
| CN102286050A (en) * | 2011-06-24 | 2011-12-21 | 天津大学 | Glucose-containing platinum complex for treating tumors and preparation method thereof |
| CN105362229A (en) * | 2015-11-19 | 2016-03-02 | 五邑大学 | Water-soluble phloretin solid dispersion and preparation method thereof |
-
2020
- 2020-10-31 CN CN202011196901.4A patent/CN112300228A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006002422A2 (en) * | 2004-06-24 | 2006-01-05 | Novartis Vaccines And Diagnostics Inc. | Compounds for immunopotentiation |
| CN102286050A (en) * | 2011-06-24 | 2011-12-21 | 天津大学 | Glucose-containing platinum complex for treating tumors and preparation method thereof |
| CN105362229A (en) * | 2015-11-19 | 2016-03-02 | 五邑大学 | Water-soluble phloretin solid dispersion and preparation method thereof |
Non-Patent Citations (2)
| Title |
|---|
| SHOU-YUAN WU,ET AL.: "A new dihydrochalcone glycoside from the stems of Homalium stenophyllum", 《NATURAL PRODUCT RESEARCH》 * |
| 赵育,等: "几种喜树碱-糖缀合物的合成及其抗肿瘤活性研究", 《中国海洋大学学报》 * |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN103230408B (en) | Method for preparing phloretin | |
| JP2024505861A (en) | Oligogalacturonic acid polysaccharide, complex and its preparation method and use thereof | |
| CN112656709A (en) | Skin care compositions and uses thereof | |
| CN108014191A (en) | A kind of Flos persicae extract and its application | |
| CN105943427B (en) | A kind of multiple-effect containing peony seed oil moistens eye cream and preparation method thereof | |
| FR2989087A1 (en) | NOVEL OLIGOSACCHARIDE COMPOUNDS AND THEIR COSMETIC USE | |
| CN104086664B (en) | Gracilaria lemaneiformis polysaccharide extract and preparation method and application thereof | |
| CN112300228A (en) | A cosmetic containing phloretin derivative containing phloroglucinol group and its preparation method | |
| CN117224454B (en) | Anti-aging/anti-saccharification essence and preparation method thereof | |
| CN112125940A (en) | Cosmetic containing tetraacetyl glucoside modified phloretin and preparation method thereof | |
| CN117045564B (en) | Skin care product containing peony extract and preparation method thereof | |
| EP4285890B1 (en) | Methods for extracting compound from ginseng | |
| CN114272165B (en) | Whitening and firming plant essence skin care lotion and preparation method thereof | |
| CN117017829A (en) | Antioxidant moisturizing composition and preparation method and application thereof | |
| CN112062870B (en) | Polysaccharide with whitening and moisturizing activities, whitening and moisturizing cream containing polysaccharide and preparation method of whitening and moisturizing cream | |
| CN112972332B (en) | Rose whitening essence and preparation method thereof | |
| CN113520888B (en) | Fullerene-containing anti-aging composition and preparation method and application thereof | |
| CN112724155B (en) | Method for preparing white glabridin by subcritical technology | |
| KR20010000390A (en) | Skin Improvement Composition Including Anti-Aging and Anti-Acne with Kimchi Extract | |
| KR20030055950A (en) | Cosmetic composition containing punica granatum l. extract for anti-aging effect | |
| CN108143674A (en) | A kind of lotion containing peony seed oil and preparation method thereof | |
| CN112851484A (en) | Method for synthesizing phloretin from naringenin | |
| CN109700690B (en) | Poria cocos moisturizing emulsion and preparation method thereof | |
| CN115025021B (en) | Whitening emulsion containing natural plant extracts | |
| FR2973381A1 (en) | New oligosaccharide compounds useful e.g. for maintaining the integrity of the constituent molecules in the extracellular matrix and for reducing the glycation and/or hyperkeratinization process |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination |