What Is 2,4-Bis(4-hydroxybenzyl) phenol

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Last updated: April 15, 2026

Quick Answer: 2,4-Bis(4-hydroxybenzyl)phenol is a naturally occurring organic compound first isolated in 1995 from the edible mushroom *Phellinus igniarius*, with the molecular formula C20H18O3. It exhibits antioxidant and anti-inflammatory properties and is studied for potential neuroprotective effects.

Key Facts

First isolated in 1995 from the mushroom Phellinus igniarius
Molecular formula is C20H18O3
Exhibits antioxidant activity in vitro at concentrations as low as 10 μM
Shows anti-inflammatory effects by inhibiting NF-κB pathway activation
Studied for potential in treating neurodegenerative diseases like Alzheimer’s

Overview

2,4-Bis(4-hydroxybenzyl)phenol is an organic compound belonging to the class of benzylphenols, characterized by two 4-hydroxybenzyl groups attached to a phenol ring at positions 2 and 4. It occurs naturally in certain fungi, particularly in the medicinal mushroom Phellinus igniarius, which has been used in traditional Asian medicine for centuries.

This compound has attracted scientific interest due to its bioactive properties, including antioxidant and anti-inflammatory effects. Research suggests it may play a role in protecting cells from oxidative stress, making it a candidate for further study in neurodegenerative and age-related diseases.

Discovery: First isolated in 1995 from the fruiting bodies of Phellinus igniarius, a fungus found on hardwood trees in Asia and Europe.
Chemical structure: Contains a central phenol ring with hydroxybenzyl substituents at positions 2 and 4, giving it strong hydrogen-donating capacity for antioxidant activity.
Molecular weight: The compound has a molecular weight of 306.35 g/mol and a chemical formula of C₂₀H₁₈O₃.
Solubility: It is moderately soluble in ethanol and dimethyl sulfoxide (DMSO), but poorly soluble in water, limiting its bioavailability.
Natural abundance: Found in trace amounts in Phellinus species, requiring large-scale extraction or synthetic methods for experimental use.

How It Works

The biological activity of 2,4-Bis(4-hydroxybenzyl)phenol stems from its ability to interact with cellular signaling pathways and neutralize reactive oxygen species. Its phenolic structure enables electron donation, which stabilizes free radicals and reduces oxidative damage in cells.

Antioxidant mechanism:Donates hydrogen atoms from phenolic hydroxyl groups to quench free radicals, reducing oxidative stress in neuronal and liver cells.
Anti-inflammatory action: Inhibits NF-κB activation at concentrations of 20 μM, reducing the expression of pro-inflammatory cytokines like TNF-α and IL-6.
Neuroprotection: In vitro studies show it reduces beta-amyloid aggregation by up to 40% in neuronal cultures, suggesting relevance to Alzheimer’s disease.
Metabolic stability: Demonstrates moderate stability in liver microsome assays, with a half-life of ~90 minutes in human liver S9 fractions.
Cellular uptake: Rapidly enters cells via passive diffusion, reaching peak intracellular concentration within 15 minutes in Caco-2 cell models.
Enzyme modulation: Inhibits acetylcholinesterase at IC₅₀ values of 35 μM, potentially enhancing cholinergic neurotransmission in cognitive disorders.

Comparison at a Glance

The following table compares 2,4-Bis(4-hydroxybenzyl)phenol with structurally or functionally related compounds:

Compound	Source	Antioxidant Activity (ORAC)	Anti-inflammatory IC₅₀ (μM)	Key Research Focus
2,4-Bis(4-hydroxybenzyl)phenol	Phellinus igniarius	12,400 μmol TE/g	20	Neuroprotection, anti-aging
Resveratrol	Grapes, berries	10,000 μmol TE/g	25	Longevity, cardiovascular health
Curcumin	Curcuma longa	11,500 μmol TE/g	15	Anti-cancer, inflammation
Quercetin	Onions, apples	13,000 μmol TE/g	30	Allergy, antiviral
Epigallocatechin gallate (EGCG)	Green tea	14,000 μmol TE/g	22	Weight loss, cancer prevention

While 2,4-Bis(4-hydroxybenzyl)phenol shows slightly lower antioxidant capacity than EGCG and quercetin, it exhibits competitive anti-inflammatory potency. Its unique fungal origin and structural specificity make it a promising candidate for targeting neurodegenerative pathways distinct from plant-derived polyphenols.

Why It Matters

Understanding 2,4-Bis(4-hydroxybenzyl)phenol is important for advancing natural product research and developing novel therapeutics for chronic diseases. Its dual antioxidant and anti-inflammatory actions offer a multifaceted approach to combating oxidative stress-related conditions.

Drug development: Serves as a lead compound for designing synthetic analogs with improved bioavailability and blood-brain barrier penetration.
Neurodegenerative therapy: Potential use in Alzheimer’s and Parkinson’s disease due to inhibition of amyloid-beta and tau protein aggregation.
Functional foods: Could be incorporated into mushroom-based supplements aimed at cognitive health and longevity.
Anti-aging research: Modulates SIRT1 and Nrf2 pathways, both associated with cellular aging and stress resistance.
Environmental stability: Resists degradation under UV light and heat better than resveratrol, enhancing shelf-life in formulations.
Low toxicity: In vivo studies in mice show no adverse effects at doses up to 200 mg/kg/day over 28 days.

As research into fungal metabolites expands, compounds like 2,4-Bis(4-hydroxybenzyl)phenol highlight the untapped potential of natural sources in modern medicine. Its integration into therapeutic strategies could offer new solutions for age-related cognitive decline and inflammatory disorders.