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Gadusol

Gadusol
Names
IUPAC name
3,4,5-trihydroxy-5-(hydroxymethyl)-2-methoxycyclohex-2-en-1-one
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
  • InChI=1S/C8H12O6/c1-14-6-4(10)2-8(13,3-9)7(12)5(6)11/h7,9,11-13H,2-3H2,1H3
    Key: KENOUOLPKKQXMX-UHFFFAOYSA-N
  • COC1=C(C(C(CC1=O)(CO)O)O)O
Properties
C8H12O6
Molar mass 204.178 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Gadusol is a secondary metabolite and natural sunscreen produced by various organisms, including marine vertebrates and invertebrates, amphibians, reptiles, and birds.[1][2]

It functions by absorbing ultraviolet radiation through its conjugated ring structure, blocking it from damaging biomolecules.[3] Gladusol is closely related to the mycosporine-like amino acid family,[2] a group of metabolites primarily produced by organisms in high-sunlight environments that absorb UV radiation. Structurally, gadusol is a substituted cyclohexenone.

References

  1. ^ Rice, Marlen C.; Little, Jordan H.; Forrister, Dale L.; Machado, Julane; Clark, Nathan L.; Gagnon, James A. (2023-08-07). "Gadusol is a maternally provided sunscreen that protects fish embryos from DNA damage". Current Biology. 33 (15): 3229–3237.e4. Bibcode:2023CBio...33E3229R. doi:10.1016/j.cub.2023.06.012. ISSN 1879-0445. PMC 10528378. PMID 37369210.
  2. ^ a b Osborn, Andrew R; Almabruk, Khaled H; Holzwarth, Garrett; Asamizu, Shumpei; LaDu, Jane; Kean, Kelsey M; Karplus, P Andrew; Tanguay, Robert L; Bakalinsky, Alan T; Mahmud, Taifo (2015-05-12). van der Donk, Wilfred A (ed.). "De novo synthesis of a sunscreen compound in vertebrates". eLife. 4 e05919. Bibcode:2015eLife...405919O. doi:10.7554/eLife.05919. ISSN 2050-084X. PMC 4426668. PMID 25965179.
  3. ^ Carvalho, P. Gigena; Naveira, R. Isla; Granone, L. I.; Mendive, C. B.; Massa, A. E.; Churio, M. S. (2023-10-01). "A comparative review of natural and synthetic UV filters: Gadusol and benzophenone-3 as representative examples". Environmental Advances. 13 100404. Bibcode:2023EnvAd..1300404C. doi:10.1016/j.envadv.2023.100404. ISSN 2666-7657.
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