Synthesis and evaluation of novel tetrapropoxycalix[4]arene enones and cinnamates for protection from ultraviolet radiation

J Photochem Photobiol B. 2011 Oct 5;105(1):25-33. doi: 10.1016/j.jphotobiol.2011.06.007. Epub 2011 Jul 6.

Abstract

A series of novel calix[4]arene enones (5-7) and cinnamates (12-14) have been synthesized and evaluated for ensuring protection from ultraviolet radiation (UVR). Spectroscopic analyses has revealed that compound 6 absorbs ultraviolet radiations between 280 and 350 nm with an absorption maximum at 312 nm. Its molar absorption coefficient (ε) (>5 × 10(4)M(-1)cm(-1)) and bandwidth are larger than those for the commercially used sun protectants (oxybenzone (OB), 2-ethylhexyl 4-methoxycinnamate (OMC) and avobenzone). The in vitro Sun Protection Factor (SPF) measurement revealed an SPF of 5.2 at 2% concentration of 6 in home made emulsion formulations while combination of 2% each of 6 and OMC gave an SPF of 8.8. Lower sun protection seems to be compensated by significant protection from more harmful UVA radiations (UVA/UVB absorbance ratio of 0.62).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Calixarenes / chemical synthesis*
  • Calixarenes / chemistry
  • Calixarenes / pharmacology
  • Cinnamates / chemical synthesis
  • Cinnamates / chemistry*
  • Cinnamates / pharmacology
  • Humans
  • Isomerism
  • Phenols / chemical synthesis*
  • Phenols / chemistry
  • Phenols / pharmacology
  • Skin / drug effects
  • Skin / radiation effects
  • Spectrophotometry, Ultraviolet
  • Sunscreening Agents / chemical synthesis*
  • Sunscreening Agents / chemistry
  • Sunscreening Agents / pharmacology
  • Ultraviolet Rays*

Substances

  • Cinnamates
  • Phenols
  • Sunscreening Agents
  • calix(4)arene
  • Calixarenes
  • 4-methoxycinnamic acid