KR20140018898A

KR20140018898A - 1,3-디옥산-5-온 화합물

1,3-디옥산-5-온 화합물 Download PDF

Info

Publication number: KR20140018898A
Authority: KR; South Korea
Prior art keywords: alkyl; formula; compound; compounds; cycloalkyl
Prior art date: 2011-02-10
Legal status : Withdrawn

Application number

KR1020137023973A

Other languages

English (en)

Korean (ko)

Inventor

토마스 루돌프

필립 뷔흘레

랄프 로쓰코프

Original Assignee

메르크 파텐트 게엠베하

Priority date

2011-02-10

Filing date

2012-01-16

Publication date

2014-02-13

2012-01-16 Application filed by 메르크 파텐트 게엠베하 filed Critical 메르크 파텐트 게엠베하

2014-02-13 Publication of KR20140018898A publication Critical patent/KR20140018898A/ko

Status Withdrawn legal-status Critical Current

Links

GYRVFISXYPPJBT-UHFFFAOYSA-N 1,3-dioxan-5-one Chemical class O=C1COCOC1 GYRVFISXYPPJBT-UHFFFAOYSA-N 0.000 title abstract description 3
238000000034 method Methods 0.000 claims abstract description 19
150000001875 compounds Chemical class 0.000 claims description 223
239000000203 mixture Substances 0.000 claims description 133
125000000217 alkyl group Chemical group 0.000 claims description 91
125000004432 carbon atom Chemical group C* 0.000 claims description 77
125000003118 aryl group Chemical group 0.000 claims description 55
239000000463 material Substances 0.000 claims description 53
238000009472 formulation Methods 0.000 claims description 46
150000003839 salts Chemical class 0.000 claims description 35
125000000753 cycloalkyl group Chemical group 0.000 claims description 31
239000002537 cosmetic Substances 0.000 claims description 30
239000000126 substance Substances 0.000 claims description 30
125000001072 heteroaryl group Chemical group 0.000 claims description 26
210000004209 hair Anatomy 0.000 claims description 23
229920006395 saturated elastomer Polymers 0.000 claims description 17
125000006413 ring segment Chemical group 0.000 claims description 16
239000011159 matrix material Substances 0.000 claims description 14
229910052739 hydrogen Inorganic materials 0.000 claims description 11
229910052760 oxygen Inorganic materials 0.000 claims description 11
229920000642 polymer Polymers 0.000 claims description 11
125000000304 alkynyl group Chemical group 0.000 claims description 10
206010051246 Photodermatosis Diseases 0.000 claims description 9
125000003342 alkenyl group Chemical group 0.000 claims description 9
230000008845 photoaging Effects 0.000 claims description 9
LOTBYPQQWICYBB-UHFFFAOYSA-N methyl n-hexyl-n-[2-(hexylamino)ethyl]carbamate Chemical compound CCCCCCNCCN(C(=O)OC)CCCCCC LOTBYPQQWICYBB-UHFFFAOYSA-N 0.000 claims description 8
229910052794 bromium Inorganic materials 0.000 claims description 6
229910052801 chlorine Inorganic materials 0.000 claims description 6
125000004122 cyclic group Chemical group 0.000 claims description 6
229910052731 fluorine Inorganic materials 0.000 claims description 6
239000000412 dendrimer Substances 0.000 claims description 5
229920000736 dendritic polymer Polymers 0.000 claims description 5
230000005525 hole transport Effects 0.000 claims description 5
238000002347 injection Methods 0.000 claims description 5
239000007924 injection Substances 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
239000012453 solvate Substances 0.000 claims description 5
229910052736 halogen Inorganic materials 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
229910052740 iodine Inorganic materials 0.000 claims description 4
229910052717 sulfur Inorganic materials 0.000 claims description 4
125000004429 atom Chemical group 0.000 claims description 3
239000000969 carrier Substances 0.000 claims description 3
239000000945 filler Substances 0.000 claims description 3
230000005669 field effect Effects 0.000 claims description 2
108091008695 photoreceptors Proteins 0.000 claims description 2
238000010791 quenching Methods 0.000 claims description 2
239000010409 thin film Substances 0.000 claims description 2
125000005418 aryl aryl group Chemical group 0.000 claims 1
230000005518 electrochemistry Effects 0.000 claims 1
239000000975 dye Substances 0.000 abstract description 47
238000002360 preparation method Methods 0.000 abstract description 29
-1 1,3-dioxan-5-one compound Chemical class 0.000 description 167
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 82
229920001223 polyethylene glycol Polymers 0.000 description 49
239000002202 Polyethylene glycol Substances 0.000 description 48
235000019441 ethanol Nutrition 0.000 description 46
239000010410 layer Substances 0.000 description 43
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 42
238000006243 chemical reaction Methods 0.000 description 35
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 34
235000014113 dietary fatty acids Nutrition 0.000 description 33
239000000194 fatty acid Substances 0.000 description 33
229930195729 fatty acid Natural products 0.000 description 33
210000003491 skin Anatomy 0.000 description 32
239000003921 oil Substances 0.000 description 30
238000004043 dyeing Methods 0.000 description 27
235000019198 oils Nutrition 0.000 description 27
GWEVSGVZZGPLCZ-UHFFFAOYSA-N titanium dioxide Inorganic materials O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 27
XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 26
HPPLHRMFZPDKNK-UHFFFAOYSA-N 2-ethoxy-2-methyl-1,3-dioxan-5-one Chemical compound CCOC1(C)OCC(=O)CO1 HPPLHRMFZPDKNK-UHFFFAOYSA-N 0.000 description 25
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 23
229910052757 nitrogen Inorganic materials 0.000 description 22
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 19
239000001993 wax Substances 0.000 description 19
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 18
150000004665 fatty acids Chemical class 0.000 description 18
239000000835 fiber Substances 0.000 description 18
239000000047 product Substances 0.000 description 18
238000011282 treatment Methods 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
108010076876 Keratins Proteins 0.000 description 17
102000011782 Keratins Human genes 0.000 description 17
239000004904 UV filter Substances 0.000 description 17
229910052799 carbon Inorganic materials 0.000 description 17
239000003795 chemical substances by application Substances 0.000 description 16
239000013078 crystal Substances 0.000 description 16
239000000839 emulsion Substances 0.000 description 16
235000011187 glycerol Nutrition 0.000 description 16
239000002904 solvent Substances 0.000 description 16
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 15
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 15
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 14
239000002253 acid Substances 0.000 description 14
150000001298 alcohols Chemical class 0.000 description 14
XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 13
239000000982 direct dye Substances 0.000 description 13
239000003995 emulsifying agent Substances 0.000 description 13
229930003935 flavonoid Natural products 0.000 description 13
235000017173 flavonoids Nutrition 0.000 description 13
229910052741 iridium Inorganic materials 0.000 description 13
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 13
239000002243 precursor Substances 0.000 description 13
235000010215 titanium dioxide Nutrition 0.000 description 13
239000011787 zinc oxide Substances 0.000 description 13
229920001577 copolymer Polymers 0.000 description 12
125000002887 hydroxy group Chemical group [H]O* 0.000 description 12
GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 12
238000001126 phototherapy Methods 0.000 description 12
235000013772 propylene glycol Nutrition 0.000 description 12
239000000243 solution Substances 0.000 description 12
239000004408 titanium dioxide Substances 0.000 description 12
239000003963 antioxidant agent Substances 0.000 description 11
150000002148 esters Chemical class 0.000 description 11
150000002215 flavonoids Chemical class 0.000 description 11
125000001424 substituent group Chemical group 0.000 description 11
235000006708 antioxidants Nutrition 0.000 description 10
GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 10
RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 10
239000000049 pigment Substances 0.000 description 10
239000007787 solid Substances 0.000 description 10
238000004659 sterilization and disinfection Methods 0.000 description 10
WSSJONWNBBTCMG-UHFFFAOYSA-N 2-hydroxybenzoic acid (3,3,5-trimethylcyclohexyl) ester Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C1=CC=CC=C1O WSSJONWNBBTCMG-UHFFFAOYSA-N 0.000 description 9
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
150000001299 aldehydes Chemical class 0.000 description 9
210000004027 cell Anatomy 0.000 description 9
239000003086 colorant Substances 0.000 description 9
230000000694 effects Effects 0.000 description 9
229940049964 oleate Drugs 0.000 description 9
ZQPPMHVWECSIRJ-KTKRTIGZSA-M oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC([O-])=O ZQPPMHVWECSIRJ-KTKRTIGZSA-M 0.000 description 9
239000000377 silicon dioxide Substances 0.000 description 9
PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical class NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 8
150000007513 acids Chemical class 0.000 description 8
ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 8
239000002775 capsule Substances 0.000 description 8
150000002191 fatty alcohols Chemical class 0.000 description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
HWYHDWGGACRVEH-UHFFFAOYSA-N n-methyl-n-(4-pyrrolidin-1-ylbut-2-ynyl)acetamide Chemical compound CC(=O)N(C)CC#CCN1CCCC1 HWYHDWGGACRVEH-UHFFFAOYSA-N 0.000 description 8
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 8
235000019645 odor Nutrition 0.000 description 8
230000001590 oxidative effect Effects 0.000 description 8
229920005862 polyol Polymers 0.000 description 8
230000008569 process Effects 0.000 description 8
239000000758 substrate Substances 0.000 description 8
GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 8
POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 7
CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 7
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 7
239000004166 Lanolin Substances 0.000 description 7
REFJWTPEDVJJIY-UHFFFAOYSA-N Quercetin Chemical compound C=1C(O)=CC(O)=C(C(C=2O)=O)C=1OC=2C1=CC=C(O)C(O)=C1 REFJWTPEDVJJIY-UHFFFAOYSA-N 0.000 description 7
239000002671 adjuvant Substances 0.000 description 7
230000003712 anti-aging effect Effects 0.000 description 7
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 7
239000003623 enhancer Substances 0.000 description 7
239000000499 gel Substances 0.000 description 7
229960004592 isopropanol Drugs 0.000 description 7
235000019388 lanolin Nutrition 0.000 description 7
229940039717 lanolin Drugs 0.000 description 7
229910052751 metal Inorganic materials 0.000 description 7
239000002184 metal Substances 0.000 description 7
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 7
150000003077 polyols Chemical class 0.000 description 7
ARIWANIATODDMH-UHFFFAOYSA-N rac-1-monolauroylglycerol Chemical compound CCCCCCCCCCCC(=O)OCC(O)CO ARIWANIATODDMH-UHFFFAOYSA-N 0.000 description 7
235000012239 silicon dioxide Nutrition 0.000 description 7
239000011734 sodium Substances 0.000 description 7
239000003981 vehicle Substances 0.000 description 7
GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 description 6
KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 6
CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 6
SBJKKFFYIZUCET-JLAZNSOCSA-N Dehydro-L-ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(=O)C1=O SBJKKFFYIZUCET-JLAZNSOCSA-N 0.000 description 6
FMRHJJZUHUTGKE-UHFFFAOYSA-N Ethylhexyl salicylate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1O FMRHJJZUHUTGKE-UHFFFAOYSA-N 0.000 description 6
UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 6
239000011786 L-ascorbyl-6-palmitate Substances 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
229910019142 PO4 Inorganic materials 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 6
VYGQUTWHTHXGQB-FFHKNEKCSA-N Retinol Palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C VYGQUTWHTHXGQB-FFHKNEKCSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
238000010521 absorption reaction Methods 0.000 description 6
230000003078 antioxidant effect Effects 0.000 description 6
235000015165 citric acid Nutrition 0.000 description 6
VFLDPWHFBUODDF-FCXRPNKRSA-N curcumin Chemical compound C1=C(O)C(OC)=CC(\C=C\C(=O)CC(=O)\C=C\C=2C=C(OC)C(O)=CC=2)=C1 VFLDPWHFBUODDF-FCXRPNKRSA-N 0.000 description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
239000004615 ingredient Substances 0.000 description 6
239000003446 ligand Substances 0.000 description 6
239000006210 lotion Substances 0.000 description 6
235000021317 phosphate Nutrition 0.000 description 6
229920001296 polysiloxane Polymers 0.000 description 6
239000000843 powder Substances 0.000 description 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
230000004224 protection Effects 0.000 description 6
230000005855 radiation Effects 0.000 description 6
150000003254 radicals Chemical class 0.000 description 6
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 6
239000004094 surface-active agent Substances 0.000 description 6
239000011732 tocopherol Substances 0.000 description 6
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239000011782 vitamin Substances 0.000 description 6
229940018563 3-aminophenol Drugs 0.000 description 5
241000894006 Bacteria Species 0.000 description 5
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 5
108010009736 Protein Hydrolysates Proteins 0.000 description 5
HEAHZSUCFKFERC-IWGRKNQJSA-N [(2e)-2-[[4-[(e)-[7,7-dimethyl-3-oxo-4-(sulfomethyl)-2-bicyclo[2.2.1]heptanylidene]methyl]phenyl]methylidene]-7,7-dimethyl-3-oxo-4-bicyclo[2.2.1]heptanyl]methanesulfonic acid Chemical group CC1(C)C2CCC1(CS(O)(=O)=O)C(=O)\C2=C\C(C=C1)=CC=C1\C=C/1C(=O)C2(CS(O)(=O)=O)CCC\1C2(C)C HEAHZSUCFKFERC-IWGRKNQJSA-N 0.000 description 5
150000004982 aromatic amines Chemical class 0.000 description 5
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230000005284 excitation Effects 0.000 description 5
229940074046 glyceryl laurate Drugs 0.000 description 5
239000007788 liquid Substances 0.000 description 5
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 5
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238000007254 oxidation reaction Methods 0.000 description 5
JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical class [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
239000003531 protein hydrolysate Substances 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 5
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YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 description 4
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CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 4
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AVKBLCWBDLLVRL-UHFFFAOYSA-N 2-(methoxymethyl)benzene-1,4-diamine Chemical compound COCC1=CC(N)=CC=C1N AVKBLCWBDLLVRL-UHFFFAOYSA-N 0.000 description 4
ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical class NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 4
OZCJSIBGTRKJGX-UHFFFAOYSA-N 4-methylcyclohexa-1,5-diene-1,4-diamine Chemical compound CC1(N)CC=C(N)C=C1 OZCJSIBGTRKJGX-UHFFFAOYSA-N 0.000 description 4
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102000008186 Collagen Human genes 0.000 description 4
108010035532 Collagen Proteins 0.000 description 4
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241001465754 Metazoa Species 0.000 description 4
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229920002125 Sokalan® Polymers 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
RLZLDSDDRORMOV-DBQHITQZSA-M [Na+].Cl.COc1ccc2cc(ccc2c1)[C@H](C)C([O-])=O.CCN(CC)CCNC(=O)c1cc(Cl)c(N)cc1OC Chemical compound [Na+].Cl.COc1ccc2cc(ccc2c1)[C@H](C)C([O-])=O.CCN(CC)CCNC(=O)c1cc(Cl)c(N)cc1OC RLZLDSDDRORMOV-DBQHITQZSA-M 0.000 description 4
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229910052783 alkali metal Inorganic materials 0.000 description 4
FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 4
229910052782 aluminium Inorganic materials 0.000 description 4
229910001870 ammonium persulfate Inorganic materials 0.000 description 4
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