JPS6330882B2 - - Google Patents
Info
- Publication number
- JPS6330882B2 JPS6330882B2 JP2216180A JP2216180A JPS6330882B2 JP S6330882 B2 JPS6330882 B2 JP S6330882B2 JP 2216180 A JP2216180 A JP 2216180A JP 2216180 A JP2216180 A JP 2216180A JP S6330882 B2 JPS6330882 B2 JP S6330882B2
- Authority
- JP
- Japan
- Prior art keywords
- sunscreen
- methylphthalide
- λmax
- yellow
- radiation
- 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.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 claims description 14
- 206010015150 Erythema Diseases 0.000 claims description 13
- 231100000321 erythema Toxicity 0.000 claims description 13
- 230000005855 radiation Effects 0.000 claims description 13
- YRTPZXMEBGTPLM-UVTDQMKNSA-N (3z)-3-benzylidene-2-benzofuran-1-one Chemical compound C12=CC=CC=C2C(=O)O\C1=C/C1=CC=CC=C1 YRTPZXMEBGTPLM-UVTDQMKNSA-N 0.000 claims description 9
- 206010042496 Sunburn Diseases 0.000 claims description 9
- 239000002537 cosmetic Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- OHRFHJYUEWVXBD-UHFFFAOYSA-N 3-[(4-chlorophenyl)methylidene]-2-benzofuran-1-one Chemical compound C1=CC(Cl)=CC=C1C=C1C2=CC=CC=C2C(=O)O1 OHRFHJYUEWVXBD-UHFFFAOYSA-N 0.000 claims description 5
- HYLSWFOHDJRUGQ-UHFFFAOYSA-N 3-[(4-methylphenyl)methylidene]-2-benzofuran-1-one Chemical compound C1=CC(C)=CC=C1C=C1C2=CC=CC=C2C(=O)O1 HYLSWFOHDJRUGQ-UHFFFAOYSA-N 0.000 claims description 5
- HBFNFJMZMTUHCH-UHFFFAOYSA-N 4-[(3-methoxyphenyl)methylidene]-3-methyl-3,3a-dihydro-2-benzofuran-1-one Chemical compound COC1=CC=CC(C=C2C3C(C(OC3C)=O)=CC=C2)=C1 HBFNFJMZMTUHCH-UHFFFAOYSA-N 0.000 claims description 5
- ANVWKIOUVJQSGG-UHFFFAOYSA-N 4-benzylidene-3-methyl-3,3a-dihydro-2-benzofuran-1-one Chemical compound C12C(C)OC(=O)C2=CC=CC1=CC1=CC=CC=C1 ANVWKIOUVJQSGG-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052736 halogen Chemical group 0.000 claims description 3
- 150000002367 halogens Chemical group 0.000 claims description 3
- 150000002431 hydrogen Chemical group 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 239000003223 protective agent Substances 0.000 claims 3
- 239000004480 active ingredient Substances 0.000 claims 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 24
- 239000000516 sunscreening agent Substances 0.000 description 15
- 230000000475 sunscreen effect Effects 0.000 description 14
- 238000002834 transmittance Methods 0.000 description 12
- YRTPZXMEBGTPLM-UHFFFAOYSA-N 3-(phenylmethylene)-1-isobenzofuranone Chemical class C12=CC=CC=C2C(=O)OC1=CC1=CC=CC=C1 YRTPZXMEBGTPLM-UHFFFAOYSA-N 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- 230000000694 effects Effects 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 7
- 238000000862 absorption spectrum Methods 0.000 description 7
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical class CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 6
- 239000001632 sodium acetate Substances 0.000 description 6
- 235000017281 sodium acetate Nutrition 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- XJNLGILMYISDGH-UHFFFAOYSA-N 3-[(3-methoxyphenyl)methylidene]-2-benzofuran-1-one Chemical compound COC1=CC=CC(C=C2C3=CC=CC=C3C(=O)O2)=C1 XJNLGILMYISDGH-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 238000012216 screening Methods 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229960003424 phenylacetic acid Drugs 0.000 description 3
- 239000003279 phenylacetic acid Substances 0.000 description 3
- WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical class O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 2
- VNDWQCSOSCCWIP-UHFFFAOYSA-N 2-tert-butyl-9-fluoro-1,6-dihydrobenzo[h]imidazo[4,5-f]isoquinolin-7-one Chemical compound C1=2C=CNC(=O)C=2C2=CC(F)=CC=C2C2=C1NC(C(C)(C)C)=N2 VNDWQCSOSCCWIP-UHFFFAOYSA-N 0.000 description 2
- TWWAWPHAOPTQEU-UHFFFAOYSA-N 4-methyl-2-benzofuran-1,3-dione Chemical compound CC1=CC=CC2=C1C(=O)OC2=O TWWAWPHAOPTQEU-UHFFFAOYSA-N 0.000 description 2
- LLKFNPUXQZHIAE-UHFFFAOYSA-N 5-(3-aminopropyl)-8-bromo-3-methyl-2h-pyrazolo[4,3-c]quinolin-4-one Chemical compound O=C1N(CCCN)C2=CC=C(Br)C=C2C2=C1C(C)=NN2 LLKFNPUXQZHIAE-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- XUMBMVFBXHLACL-UHFFFAOYSA-N Melanin Chemical compound O=C1C(=O)C(C2=CNC3=C(C(C(=O)C4=C32)=O)C)=C2C4=CNC2=C1C XUMBMVFBXHLACL-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- CDPKJZJVTHSESZ-UHFFFAOYSA-N 4-chlorophenylacetic acid Chemical compound OC(=O)CC1=CC=C(Cl)C=C1 CDPKJZJVTHSESZ-UHFFFAOYSA-N 0.000 description 1
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- DIWVBIXQCNRCFE-UHFFFAOYSA-N DL-alpha-Methoxyphenylacetic acid Chemical compound COC(C(O)=O)C1=CC=CC=C1 DIWVBIXQCNRCFE-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000003581 cosmetic carrier Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 229940120503 dihydroxyacetone Drugs 0.000 description 1
- 238000004836 empirical method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 230000000191 radiation effect Effects 0.000 description 1
- 239000000718 radiation-protective agent Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000037380 skin damage Effects 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
Landscapes
- Cosmetics (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US1459879A | 1979-02-23 | 1979-02-23 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS55115818A JPS55115818A (en) | 1980-09-06 |
| JPS6330882B2 true JPS6330882B2 (enrdf_load_stackoverflow) | 1988-06-21 |
Family
ID=21766433
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2216180A Granted JPS55115818A (en) | 1979-02-23 | 1980-02-23 | Sunshine sheltering agent |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS55115818A (enrdf_load_stackoverflow) |
-
1980
- 1980-02-23 JP JP2216180A patent/JPS55115818A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS55115818A (en) | 1980-09-06 |
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