A lichen metabolite
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Isomer(s)
33079Trypacidin
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Usnic Acid

Item No. 22585

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2,6-diacetyl-7,9-dihydroxy-8,9b-dimethyl-1,3(2H,9bH)-dibenzofurandione
CAS Number
125-46-2
Synonyms
  • NSC 8517
Molecular Formula
C18H16O7
Formula Weight
344.3
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 2.5 mg/mlDMF:PBS (pH7.2) (1:40): 0.02 mg/ml
λmax
233, 282 nm
SMILES
CC1(C(C2C(C)=O)=O)C3=C(O)C(C)=C(O)C(C(C)=O)=C3OC1=CC2=O
InChi Code
InChI=1S/C18H16O7/c1-6-14(22)12(8(3)20)16-13(15(6)23)18(4)10(25-16)5-9(21)11(7(2)19)17(18)24/h5,11,22-23H,1-4H3
InChi Key
CUCUKLJLRRAKFN-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 g

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    Cayman Chemical
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    Product Description

    Usnic acid is a lichen metabolite with antioxidant, anticancer, antifungal, antiprotozoal, and antimicrobial activities.1,2,3,4,5 Usnic acid (>50 mg/kg) reduces the number of indomethacin-induced gastric ulcers in rats through decreased lipid peroxidation and decreased myeloperoxidase activity.1 It is fungicidal against C. orthopsilosis and C. parapsilosis (IC80s = 7.8 and 15.6 μg/ml, respectively) and bactericidal against seven vancomycin-resistant E. faecalis strains (MIC = 125 μg/ml).2,3 Usnic acid (25 mg/kg, injected intralesionally) reduces L. amazonensis parasite loads by 72.3% in footpads of infected mice.4 It also reduces growth of A2780, HeLa, MCF-7, SK-BR-3, HT-29, HCT116, HL-60, and Jurkat cancer cells in vitro (IC50s = 48.5-199 μM).5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Odabasoglu, F., Cakir, A., Suleyman, H., et al. Gastroprotective and antioxidant effects of usnic acid on indomethacin-induced gastric ulcer in rats. J. Ethnopharmacol. 103(1), 59-65 (2006).

    2. Elo, H., Matikainen, J., and Pelttari, E. Potent activity of the lichen antibiotic (+)-usnic acid against clinical isolates of vancomycin-resistant enterococci and methicillin-resistant Staphylococcus aureus. Naturwissenschaften 94(6), 465-468 (2007).

    3. Araújo, A.A., de Melo, M.G., Rabelo, T.K., et al. Review of the biological properties and toxicity of usnic acid. Nat. Prod. Res. 29(23), 2167-2180 (2015).

    4. Fournet, A., Ferreira, M.-E., Rojas de Arias, A., et al. Activity of compounds isolated from Chilean lichens against experimental cutaneous leishmaniasis. Comp. Biochem. Physiol. 116(1), 51-54 (1997).

    5. Bačkorová, M., Bačkor, M., Mikeš, J., et al. Variable responses of different human cancer cells to the lichen compounds parietin, atranorin, usnic acid and gyrophoric acid. Toxicol. In Vitro 25(1), 37-44 (2011).