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The Convenient Syntheses of 4-(2,3- Dihydroxypropoxy)-4’-Substitued Dibenzoylmethane Derivatives as Hydrophilic Ultraviolet Absorbing Agents

International Journal of Applied Chemistry
© 2020 by SSRG - IJAC Journal
Volume 7 Issue 1
Year of Publication : 2020
Authors : Yoshifumi Yuasa, Akiko Horizoe
10.14445/23939133/IJAC-V7I1P101
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How to Cite?

Yoshifumi Yuasa, Akiko Horizoe, "The Convenient Syntheses of 4-(2,3- Dihydroxypropoxy)-4’-Substitued Dibenzoylmethane Derivatives as Hydrophilic Ultraviolet Absorbing Agents," SSRG International Journal of Applied Chemistry, vol. 7,  no. 1, pp. 1-5, 2020. Crossref, https://doi.org/10.14445/23939133/IJAC-V7I1P101

Abstract:

New dibenzoylmethane derivatives 1a-e having a glyceryloxy group as the hydrophilic nature have been synthesized by the condensation of 4- acetonidebenzoate 5 and 4-subustited acetophenone 6a-e in the presence of NaNH2, followed by acidic hydrolysis. These compounds 1a-e have an excellent solubility in oily and water-soluble bases and are expected to be the extremely useful as UV absorbers in the UV-A region.

Keywords:

UV absorber; UV-A region, Dibenzoylmethane derivative, Glyceryloxy group, Hydrophilic.

References:

[1] There are many reports, for example, a) FJ. Moloney, S.Collins, GM. Murphy.“Sunscreens: safety, efficacy and appropriate use” Am. J. Clin. Dermatol, 2002, 3(3), pp. 185-191. b) R. Rai, CR. Srinivas. “Photoprotection” Indian J. Dermatol Venereol Leprol. 2007, 73(2), pp. 73-79. c) S. Gabros, P. M. Zito. “Sunscreens and Photoprotection”. StatPearls Publishing LLC, 2019.
[2] a) K.-F. De Polo. “4-(1,1-Dimethyl)-4-methoxydibenzoylmethane” US Patent, 4387089, 1981. b) B.V. Erfinder: C. Wehrli. “Process for the manufacture of dibenzoylmethane derivatives” WO Patent 2012084770A1, 2012.
[3] K.-F. De Polo. “Lichtschutzmittel”. Swiss Patent CH1 1639/78, 1978.
[4] G. Lang: A. Malaval.“Quaternary dibenzoylmethane derivatives and their application as sun filter”, EP. FR Patent, 2488252 (A1), 1982, JP Patent, 5759840(A), 1982.
[5] H. Nakamura: M. Hattori: T. Teshima: N. Takaishi: G. Imokawa. “Long wavelength”, JP Patent, 6019078 (A), 1985.
[6] Y. Utsuki: M. Ochiai. J“New benzophenone derivatives and their application as sun filters”, JP Patent, 58110535(A), 1983.
[7] a) A. N. de Belder, “Cyclic acetals of the aldoses and aldosides.” Adv. Carbohydr. Chem., 20, pp. 219-302, 1965. b) O. Th. Schmidt, Methods Carbohydr. Chem., II, pp. 318-325, 1963.
[8] a) C. R. Hauser, F. W. Swamer, and J. T. Adams. In Organic Reaction, Vol. 8. Edited by R. Adams., John Wiley & Sons, Inc. New York. 1954. Chap. 3; pp. 59-196. b) C. R. Hauser, and J. T. Adams. “The Acylation of Methyl Ketones with Aliphatic Esters by Means of Sodium Amide. Synthesis of β-Diketones of the Type RCOCH2COR1” J. Am. Chem, Soc., 1944, 66, pp. 1220-1222.