Gadusol

Gadusol
Names
	IUPAC name 3,4,5-trihydroxy-5-(hydroxymethyl)-2-methoxycyclohex-2-en-1-one
Identifiers
CAS Number	76663-30-4;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:172445;
ChemSpider	169841;
PubChem CID	195955;
CompTox Dashboard (EPA)	DTXSID00997986 ;
	InChI 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;
	SMILES COC1=C(C(C(CC1=O)(CO)O)O)O;
Properties
Chemical formula	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). Infobox references

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

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

References

↑ 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.
1 2 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.
↑ 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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[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.

[:0-2] 1 2 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.