Dioctyl 4-Methoxybenzylidenemalonate:A New UV-B Absorber

• Oguchi (Fujiyama) Nozomi

  株式会社　資生堂リサーチセンター

• Miyazawa Kazuyuki

  株式会社　資生堂リサーチセンター

• Kikuchi Azusa

  横浜国立大学

• Yagi Mikio

  横浜国立大学

Bibliographic Information

Other Title

• 新規UV-B吸収剤：ジオクチルメトキシベンジリデンマロネートの設計とUV-A吸収剤光安定化効果
• シンキ UV-B キュウシュウザイ : ジオクチルメトキシベンジリデンマロネート ノ セッケイ ト UV-A キュウシュウザイ ヒカリ アンテイカ コウカ

Abstract

The most important characteristics of an effective and safe UV absorber used as a UV-blocking compound in cosmetic sunscreens is photochemical stability. The most widely used organic UV-A absorber is 4-tert-butyl-4'-methoxydibenzoylmethane (BMDBM). However, BMDBM is well-known for its photoinstability under actual conditions of use. The commonly employed method for improving the photostablity of BMDBM is based on the addition of another UV absorber. Octocrylene (OCR) has been found to be most effective at stabilizing BMDBM. In some sunscreen formulations, octyl 4-methoxycinnamate (OMC), the most widely used representative UV-B absorber, is added to the mixture of BMDBM and OCR to provide effective protection throughout the whole UV range of solar radiation because the molar absorption coefficients of OCR are small in the UV-B region. In the present study, we have shown that the observed photostablity of BMDBM in the BMDBM-OCR-OMC combination is lower than that in the BMDBM-OCR combination. To eliminate this problem, we have designed a new UV-B absorber, dioctyl 4-methoxybenzylidenemalonate (DOMBM), which does not undergo cis-trans photoisomerization owing to its molecular structure. We tested the effect of the addition of DOMBM on the photostability of BMDBM in the BMDBM-OCR-DOMBM combination. The photostablity of BMDBM in the BMDBM-OCR-DOMBM combination is higher than those in the BMDBM-OCR and BMDBM-OCR-OMC combinations. It is suggested that intermolecular triplet-triplet energy transfer from BMDBM to DOMBM and the photostable filter effect of DOMBM on BMDBM are possible mechanisms to explain the photostability of BMDBM in the combination of UV-A and UV-B absorbers.

Journal

• Journal of Society of Cosmetic Chemists of Japan

  Journal of Society of Cosmetic Chemists of Japan 47 (3), 209-215, 2013

  The Society of Cosmetic Chemists of Japan

Keywords

• UV absorber
• photo stability
• 4-<i>tert</i>-butyl-4'-methoxydibenzoylmethane
• dioctyl 4-methoxybenzylidenemalonate
• octocrylene

Details

• CRID: 1390282679477714560
• NII Article ID: 130005099435
• NII Book ID: AN00101606
• DOI: 10.5107/sccj.47.209
• ISSN: 18844146
• ISSN: 03875253
• NDL BIB ID: 024914964
• Web Site: http://id.ndl.go.jp/bib/024914964
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I024914964
• Web Site: https://www.jstage.jst.go.jp/article/sccj/47/3/47_209/_pdf
• Text Lang: ja
• Data Source:
  • JaLC
  • NDL
  • Crossref
  • CiNii Articles
  • KAKEN
• Abstract License Flag: Disallowed