Evernic Acid: Properties, Sources & Research Uses

Evernic acid is a naturally occurring depside isolated from lichens, valued in biomedical research for its antimicrobial, antioxidant, and cytotoxic properties.

Chemical Class

Depside (ester-linked phenolic dimer)

Primary Natural Source

Lichens, notably Evernia prunastri (oakmoss) and related species

CAS / SKU

537-09-7 / E332692 (Aladdin Scientific)

Molecular Formula

C₁₇H₁₆O₇

Key Biological Activities

Antimicrobial, antioxidant, anti-inflammatory, cytotoxic

Appearance

White to off-white crystalline solid

Solubility

Soluble in ethanol, DMSO, acetone; sparingly soluble in water

Chemical Identity and Structure

Evernic acid (CAS 537-09-7; molecular formula C₁₇H₁₆O₇; MW ~324.30 g/mol) is a depside — a class of natural polyketide-derived phenolic esters — consisting of two orcinol-type aromatic rings connected by an ester linkage. The compound features hydroxyl, methoxy, and carboxylic acid functional groups that underpin its broad reactivity and bioactivity profile. Its systematic IUPAC name is 2-hydroxy-4-(2-hydroxy-4-methoxy-6-methylbenzoyloxy)-6-methylbenzoic acid. The planar aromatic scaffold and multiple hydrogen-bond donors/acceptors make evernic acid an attractive scaffold for medicinal chemistry exploration. Researchers should be aware that the compound is light- and moisture-sensitive and should be stored at 2–8 °C under inert atmosphere when long-term stability is required.

Natural Sources and Biosynthesis

Evernic acid is produced as a secondary metabolite predominantly by foliose and fruticose lichens. The most well-known source is Evernia prunastri (oakmoss lichen), from which the compound derives its name. It is also found in species of Ramalina, Parmelia, and Usnea. Within the lichen thallus, evernic acid is biosynthesised via the polyketide pathway through iterative condensation of acetate units, followed by aromatic ring formation and esterification to yield the characteristic depside scaffold. Because lichens grow slowly and environmental harvesting is not scalable, chemical synthesis and semi-synthesis from simpler phenolic precursors are used for laboratory supply. Aladdin Scientific supplies evernic acid (SKU E332692) as an isolated, purified reference standard suitable for in vitro assay work.

Biological Activities and Research Applications

Evernic acid has attracted sustained research interest due to its diverse pharmacological activities:

• Antimicrobial activity: Multiple studies have reported inhibitory effects against Gram-positive bacteria (including Staphylococcus aureus and Bacillus spp.) and certain fungi. Its mechanism is proposed to involve disruption of cell membrane integrity and inhibition of key metabolic enzymes, though precise molecular targets remain under investigation.
• Antioxidant activity: Evernic acid scavenges free radicals in standard in vitro assays such as DPPH and ABTS, attributed to its phenolic hydroxyl groups. These properties position it as a tool compound in oxidative-stress research.
• Anti-inflammatory effects: Preliminary studies suggest inhibition of pro-inflammatory mediators, warranting further mechanistic investigation.
• Cytotoxic and anticancer potential: Cell-line studies have demonstrated dose-dependent cytotoxicity against various human cancer cell lines, making evernic acid a candidate scaffold for anticancer drug discovery programs.
• Enzyme inhibition: Evernic acid has been reported to inhibit certain proteases and other enzyme classes, relevant to drug-target interaction studies.

Researchers use evernic acid as a reference compound in natural-product screening libraries, as a positive control in antimicrobial or antioxidant assays, and as a starting material for synthetic analogue programs.

Handling, Storage, and Laboratory Safety

As with most phenolic natural products, evernic acid requires careful handling in the laboratory:

• Storage: Store at 2–8 °C in a tightly sealed container, protected from light and moisture. Under recommended conditions the solid is stable for at least 24 months (verify with certificate of analysis).
• Solvent preparation: Prepare stock solutions in DMSO (typically 10–50 mM) or ethanol. Avoid aqueous dilution without an organic co-solvent, as aqueous solubility is low. Filter-sterilise solutions (0.2 µm) for cell-based assays and use freshly prepared aliquots where possible.
• Personal protective equipment: Wear nitrile gloves, lab coat, and safety glasses. Although evernic acid is not classified as acutely hazardous, its biological activity warrants standard laboratory precautions. Consult the Safety Data Sheet (SDS) before use.
• Waste disposal: Dispose of solutions and contaminated materials according to local regulations for organic chemical waste.

Procurement and Quality at Aladdin Scientific

Aladdin Scientific offers evernic acid under SKU E332692, supplied with a certificate of analysis (CoA) confirming identity, purity, and lot-specific data. The product reference cross-matches to Santa Cruz Biotechnology sc-294581, facilitating direct substitution for researchers transitioning between suppliers. When placing orders, procurement teams should request the CoA and SDS to ensure the material meets in-house quality requirements. For bulk quantities or custom packaging, contact Aladdin Scientific's technical sales team. As a research reagent, evernic acid (E332692) is intended for laboratory research use only and is not approved for clinical or veterinary applications.

Frequently asked questions

What is evernic acid used for in research?

Evernic acid is used as a reference standard and tool compound in studies of antimicrobial, antioxidant, anti-inflammatory, and cytotoxic activities. It is also employed as a positive control in bioassays and as a scaffold for the synthesis of structural analogues in medicinal chemistry programs.

How should evernic acid (E332692) be dissolved for cell-based assays?

Prepare a concentrated stock solution in DMSO (10–50 mM) or ethanol, then dilute into aqueous assay medium immediately before use to avoid precipitation. Ensure the final DMSO concentration in cell culture does not exceed 0.1–0.5% (v/v) to prevent solvent toxicity. Filter-sterilise through a 0.2 µm membrane.

Is Aladdin's evernic acid (E332692) equivalent to Santa Cruz sc-294581?

Yes. The product description confirms a cross-reference to Santa Cruz Biotechnology catalog number sc-294581. Researchers switching suppliers should request and compare certificates of analysis to verify that purity and specification criteria are equivalent for their specific application.

What are the recommended storage conditions for evernic acid?

Store evernic acid as a solid at 2–8 °C in a sealed, light-protected container under dry conditions. For long-term storage, an inert atmosphere (argon or nitrogen) is advisable. Stock solutions should be aliquoted and stored at –20 °C, avoiding repeated freeze-thaw cycles.

What is the molecular weight and formula of evernic acid?

Evernic acid has the molecular formula C₁₇H₁₆O₇ and a molecular weight of approximately 324.30 g/mol. Its CAS registry number is 537-09-7.

References

1. Ranković B. (Ed.) Lichen Secondary Metabolites: Bioactive Properties and Pharmaceutical Potential. Springer, 2015.
2. Shukla V, Joshi GP, Rawat MSM. Lichens as a potential natural source of bioactive compounds: a review. Phytochemistry Reviews. 2010;9(2):303-314.
3. Çobanoğlu G, et al. Antimicrobial activity of some lichen species and their secondary metabolites. Biological Diversity and Conservation. 2010.
4. Aladdin Scientific product page: Evernic acid, SKU E332692. Retrieved 2024.

Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.