Photoisomerisation of the sunscreen filter PARSOL® 1789

被引:22
作者
Dubois, M [1 ]
Gilard, P [1 ]
Tiercet, P [1 ]
Deflandre, A [1 ]
Lefebvre, MA [1 ]
机构
[1] LOreal, Lab Rech Avancee, Direct Sci Mat, F-93601 Aulnay Sous Bois, France
关键词
sunscreen; beta-diketone; enol; tautomerism; NMR;
D O I
10.1051/jcp:1998149
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
PARSOL(R) 1789 exists in solution in three tautomeric forms: two cis-enols and a beta-diketone. The enol forms predominate. Irradiation of a very dilute solution of PARSOL(R) 1789 in acetonotrile with a Xenon lamp increases the percentage of beta-diketone to become the predominant form present. This photoisomerisation has been studied by means of H-1 and C-13 NMR.
引用
收藏
页码:388 / 394
页数:7
相关论文
共 13 条
[1]   A UVA filter (4-tert-butyl-4'-methoxydibenzoylmethane): Photoprotection reflects photophysical properties [J].
Andrae, I ;
Bringhen, A ;
Bohm, F ;
Gonzenbach, H ;
Hill, T ;
Mulroy, L ;
Truscott, TG .
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY B-BIOLOGY, 1997, 37 (1-2) :147-150
[2]  
BATTESTI P, 1974, B SOC CHIM FR II-CH, P2214
[3]   H-1 AND C-13 ASSIGNMENTS FROM SENSITIVITY-ENHANCED DETECTION OF HETERONUCLEAR MULTIPLE-BOND CONNECTIVITY BY 2D MULTIPLE QUANTUM NMR [J].
BAX, A ;
SUMMERS, MF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (08) :2093-2094
[4]  
Bolvig S, 1996, MAGN RESON CHEM, V34, P467
[5]  
*CTFA COSM INGR DI, 1995, COSM TOIL FAGR ASS, V1, P120
[6]   THE PREFERENTIAL DIRECTION OF ENOLIZATION OF SOME ASYMMETRIC 1,3-DICARBONYL COMPOUNDS IN SOLUTION - A STUDY BY MULTINUCLEAR NMR-SPECTROSCOPY [J].
GERALDES, CFGC ;
BARROS, MT ;
MAYCOCK, CD ;
SILVA, MI .
JOURNAL OF MOLECULAR STRUCTURE, 1990, 238 :335-346
[7]   INTERMOLECULAR HYDROGEN-BONDING EFFECTS ON C-13 NMR SHIELDING FOR ENOL FORMS OF DIKETONES IN THE SOLID-STATE [J].
IMASHIRO, F ;
MAEDA, S ;
TAKEGOSHI, K ;
TERAO, T ;
SAIKA, A .
CHEMICAL PHYSICS LETTERS, 1982, 92 (06) :642-645
[8]   C-13 NMR-SPECTRA AND ENOL-ENOL TAUTOMERISM IN CRYSTALLINE KETO-ENOLS [J].
KOLTSOV, AI ;
ELKIN, AA ;
ZHEGLOVA, DK .
JOURNAL OF MOLECULAR STRUCTURE, 1990, 221 :309-313
[9]   Keto-enol tautomerism of dimedone studied by dynamic NMR [J].
MartinezRicha, A ;
MendozaDiaz, G ;
JosephNathan, P .
APPLIED SPECTROSCOPY, 1996, 50 (11) :1408-1412
[10]   KINETIC-STUDIES OF FAST EQUILIBRIUM BY MEANS OF HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHY .11. KETO-ENOL-TAUTOMERISM OF SOME BETA-DICARBONYL COMPOUNDS [J].
MORIYASU, M ;
KATO, A ;
HASHIMOTO, Y .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1986, (04) :515-520