A lichen metabolite with diverse biological activities
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Vulpinic Acid

Item No. 21685

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
αE-(3-hydroxy-5-oxo-4-phenyl-2(5H)-furanylidene)-benzeneacetic acid, methyl ester
CAS Number
521-52-8
Synonyms
  • NSC 5897
Molecular Formula
C19H14O5
Formula Weight
322.3
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMF:PBS (pH 7.2) (1:2): 0.33 mg/mlDMSO: 20 mg/ml
λmax
233, 281, 367 nm
SMILES
OC(/C(O1)=C(C(OC)=O)/C2=CC=CC=C2)=C(C3=CC=CC=C3)C1=O
InChi Code
InChI=1S/C19H14O5/c1-23-18(21)15(13-10-6-3-7-11-13)17-16(20)14(19(22)24-17)12-8-4-2-5-9-12/h2-11,20H,1H3/b17-15+
InChi Key
OMZRMXULWNMRAE-BMRADRMJSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    10 mg

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    Product Description

    Vulpinic acid is a lichen metabolite that has been found in L. vulpina and has diverse biological activities.1,2,3,4 It is active against C. perfringens, B. vulgatus, B. fragilis, B. loescheii, P. acnes, E. faecium, and methicillin-susceptible and -resistant S. aureus (MICs = 4-16 μg/ml).1 Vulpinic acid (25-800 μM) prevents UVB-induced apoptosis, cytotoxicity, and cytoskeletal modifications in HaCaT human keratinocytes.2 It also increases scratch wound healing of HaCaT cells.3 Vulpinic acid (15 μM) reduces hydrogen peroxide-induced production of reactive oxygen species (ROS) and cytotoxicity in human umbilical vein endothelial cells (HUVECs).4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Lauterwein, M., Oethinger, M., Belsner, K., et al. In vitro activities of the lichen secondary metabolites vulpinic acid, (+)-usnic acid, and (—)-usnic acid against aerobic and anaerobic microorganisms. Antimicrob. Agents Chemother. 39(11), 2541-2543 (1995).

    2. Varol, M., Türk, A., Candan, M., et al. Photoprotective activity of vulpinic and gyrophoric acids toward ultraviolet B-induced damage in human keratinocytes. Phytother. Res. 30(1), 9-15 (2016).

    3. Burlando, B., Ranzato, E., Volante, A., et al. Antiproliferative effects on tumour cells and promotion of keratinocyte wound healing by different lichen compounds. Planta. Med. 75(6), 607-613 (2009).

    4. Sahin, E., Psav, S.D., Avan, I., et al. Vulpinic acid, a lichen metabolite, emerges as a potential drug candidate in the therapy of oxidative stress–related diseases, such as atherosclerosis. Hum. Exp. Toxicol. 38(6), 675-684 (2019).