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Flavipin

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Flavipin
Names
Preferred IUPAC name 3,4,5-Trihydroxy-6-methylbenzene-1,2-dicarbaldehyde
Other names
    • 3,4,5-Trihydroxy-6-methylphthalaldehyde
    • HY-N10295
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C9H8O5/c1-4-5(2-10)6(3-11)8(13)9(14)7(4)12/h2-3,12-14H,1H3Key: COJARPHAKVBMFD-UHFFFAOYSA-N
SMILES
  • CC1=C(C(=C(C(=C1O)O)O)C=O)C=O
Properties
Chemical formula C9H8O5
Molar mass 196.158 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Flavipin is a phototoxic, antibiotic and antifungal metabolite with the molecular formula C9H8O5 which is produced by the fungi Aspergillus flavipes, Epicoccum nigrum and Epicoccum andropogonis. Flavipin is also a potent antioxidant.

References

  1. Mücke, Wolfgang; Lemmen, Christa (2004). Schimmelpilze: Vorkommen, Gesundheitsgefahren, Schutzmaßnahmen (in German). ecomed-Storck GmbH. p. 30. ISBN 978-3-609-68001-9.
  2. "Flavipin". Pubchem.ncbi.NLM.nih.gov.
  3. Bamford, P.C.; Norris, G.L.F.; Ward, G. (September 1961). "Flavipin production by Epicoccum spp". Transactions of the British Mycological Society. 44 (3): 354–356. doi:10.1016/S0007-1536(61)80028-4.
  4. Ye, Yonghao; Xiao, Yu; Ma, Liang; Li, Hongxia; Xie, Zhenglu; Wang, Minghua; Ma, Haitian; Tang, Huaiwu; Liu, Junyan (August 2013). "Flavipin in Chaetomium globosum CDW7, an endophytic fungus from Ginkgo biloba, contributes to antioxidant activity". Applied Microbiology and Biotechnology. 97 (16): 7131–7139. doi:10.1007/s00253-013-5013-8. PMID 23740314. S2CID 1246044.

Further reading

  • Korzybski, Tadeusz; Kowszyk-Gindifer, Zuzanna; Kurylowicz, Wlodzimierz (3 September 2013). Antibiotics: Origin, Nature and Properties. Elsevier. p. 1285. ISBN 978-1-4832-2304-9.
  • Abdel-Azeem, Ahmed M. (2021). Industrially Important Fungi for Sustainable Development: Volume 2: Bioprospecting for Biomolecules. Springer Nature. p. 135. ISBN 978-3-030-85603-8.
  • Lloyd, D. (6 December 2012). Topics in Carbocyclic Chemistry: Volume One. Springer Science & Business Media. p. 90. ISBN 978-1-4684-8270-6.
  • Nitao, James; Meyer, Susan; Chitwood, David; Schmidt, Walter; Oliver, James (2002). "Isolation of flavipin, a fungus compound antagonistic to plant-parasitic nematodes". Nematology. 4 (1): 55–63. doi:10.1163/156854102760082203.
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