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Trolox

Trolox is a synthetic, water-soluble analog of vitamin E (α-tocopherol), chemically designated as 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid, with the molecular formula C14H18O4 and a molecular weight of 250.29 g/mol.^[1] It exhibits potent antioxidant properties by scavenging reactive oxygen species (ROS) and lipid peroxides, thereby mitigating oxidative stress and associated cellular damage.^[2] As a cell-permeable compound, Trolox is widely utilized in biochemical and pharmacological research as a standard for evaluating the antioxidant capacity of complex mixtures through assays like the Trolox Equivalent Antioxidant Capacity (TEAC) method.^[3] Developed as a more hydrophilic derivative of natural vitamin E to enhance solubility in aqueous environments, Trolox mimics the chroman ring structure of tocopherol but incorporates a carboxylic acid group at the 2-position, improving its bioavailability in experimental settings.^[4] In research applications, it effectively inhibits peroxynitrite-induced oxidative damage and apoptosis.^[4] Beyond basic antioxidant assays, Trolox has demonstrated utility in studying ferroptosis inhibition, particularly in cancer models like artesunate-treated head and neck squamous cell carcinoma cells, where it blocks lipid peroxidation pathways.^[2] It also shows neuroprotective effects, such as when combined with coenzyme Q10 to reduce oxidative injury in neuronal tissues.^[2] Commercially available from suppliers like Hoffman-La Roche and various chemical vendors, Trolox is typically stored as a powder or solution under refrigerated conditions to maintain stability, with solubility up to 10 mM in water.^[5] While primarily a research tool, its role in adjunctive therapies for conditions involving oxidative stress, including certain cancers and neurodegenerative diseases, continues to be explored in preclinical studies.^[6]

Chemical Properties

Structure and Nomenclature

Trolox is a synthetic organic compound with the chemical formula C14H18O4, serving as a water-soluble analog of vitamin E.^[1] Its systematic IUPAC name is 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid.^[1] Common synonyms include Trolox and Trolox C.^[1] The molecular structure of Trolox features a chroman ring, which is a fused benzene and pyran ring system, with a hydroxyl group (-OH) attached to the 6-position on the benzene ring. Four methyl groups (-CH3) are positioned at the 2, 5, 7, and 8 carbons, and a carboxylic acid group (-COOH) is bonded to the 2-position on the pyran ring, contributing to its overall chirality at that carbon. This arrangement mimics key structural elements of tocopherols while incorporating the polar carboxylic acid for enhanced solubility.^[1] Trolox has a molecular weight of 250.29 g/mol. Its CAS registry number is 53188-07-1, which uniquely identifies it in chemical databases.^[3]

Physical and Spectroscopic Properties

Trolox appears as a white to light beige crystalline powder.^[7] Its melting point ranges from 187 °C to 194 °C.^[8] Trolox demonstrates moderate solubility in water, approximately 0.5 mg/mL at neutral pH, increasing to about 3 mg/mL at pH 7.2 owing to deprotonation of the carboxylic acid group on the chroman ring structure; it is readily soluble in DMSO and ethanol up to 25 mg/mL.^[4]^[9]^[10] The compound remains stable under recommended storage conditions at 2–8 °C and normal pressures but decomposes upon heating beyond its melting point.^[11] In UV-Vis spectroscopy, Trolox exhibits a characteristic absorption maximum at 291 nm in methanol.^[12] Infrared (IR) spectroscopy reveals key vibrational bands including a broad O-H stretch from the phenolic group at 3550–3200 cm⁻¹, a C=O stretch from the carboxylic acid at approximately 1710 cm⁻¹, and aromatic C-H stretches around 3000–3100 cm⁻¹.^[13]^[14] ¹H NMR spectroscopy (400 MHz, DMSO-d₆) displays distinct signals for the methyl protons, with singlets at δ 1.36 (3H, CH₃ at C-2), 1.95 (3H), 2.00 (3H), and 2.03 (3H) for the aromatic methyl groups, alongside multiplets for the chroman ring CH₂ protons at δ 1.48–1.56 (m, 1H, CH₂-3), 2.24–2.29 (m, 1H, CH₂-3), and 2.41–2.44 (m, 2H, CH₂-4).^[14] Trolox possesses two acidic protons with pKₐ values of approximately 3.9 for the carboxylic acid and 11.9 for the phenolic hydroxyl group.^[15]^[16]

Biological Activity

Antioxidant Mechanism

Trolox primarily exerts its antioxidant effects through a hydrogen atom transfer (HAT) mechanism, in which the phenolic hydroxyl group donates a hydrogen atom to peroxyl radicals (ROO•), generating a stable phenoxyl radical (ArO•) that terminates the radical chain reaction.^[17] This process is depicted in the following key reaction:

\text{ArOH} + \text{ROO}^\bullet \rightarrow \text{ArO}^\bullet + \text{ROOH}

where ArOH represents the phenolic moiety of Trolox.^[18] In addition to targeting peroxyl radicals, Trolox scavenges various reactive oxygen species (ROS), including superoxide anions (O₂⁻•), hydroxyl radicals (•OH), and peroxynitrite (ONOO⁻), thereby mitigating oxidative damage in biological systems.^[19]^[20]^[21] As a chain-breaking antioxidant, Trolox inhibits the propagation phase of lipid peroxidation by donating a hydrogen atom to lipid-derived peroxyl radicals, preventing further radical formation and membrane damage.^[22]^[23] Unlike lipophilic antioxidants such as α-tocopherol, Trolox's carboxylic acid group confers water solubility, enabling it to act effectively in aqueous phases while also partitioning into lipid bilayers of cell membranes to protect against oxidative stress at interfaces.^[24] This dual-phase activity enhances its utility in cellular environments.^[25] Furthermore, Trolox inhibits peroxynitrite-mediated apoptosis by scavenging this potent oxidant, thereby blocking downstream signaling pathways that lead to programmed cell death in oxidative stress conditions.^[26]

Relation to Vitamin E

Trolox was developed by Hoffmann-La Roche in the 1970s as a synthetic analog of α-tocopherol, the predominant and most biologically active form of vitamin E. This compound, which is not found in nature, was created to address limitations in the solubility of natural vitamin E, enabling its use in diverse experimental settings.^[27]^[2] The primary structural change in Trolox is the substitution of α-tocopherol's long, hydrophobic phytyl chain with a carboxylic acid group, rendering it highly water-soluble while preserving the chromanol ring essential for antioxidant function. This modification allows Trolox to mimic vitamin E's role as a chain-breaking antioxidant in lipid environments but extends its efficacy to hydrophilic phases, such as aqueous cellular compartments or extracellular fluids.^[28] In terms of bioavailability, Trolox's water solubility facilitates more rapid absorption in aqueous systems compared to the fat-soluble α-tocopherol, which requires lipid carriers for uptake and is primarily stored in adipose tissue and the liver for long-term reserves. Consequently, Trolox does not accumulate in fatty depots like vitamin E, leading to shorter persistence in the body but improved accessibility in non-lipidic contexts.^[29]^[30] Trolox is frequently employed as a 1:1 molar equivalent to α-tocopherol in antioxidant capacity assays, such as the Trolox Equivalent Antioxidant Capacity (TEAC) method, where it serves as a standard due to its comparable peroxyl radical scavenging efficiency on a molar basis. This equivalence underscores its utility as a benchmark for evaluating other antioxidants in vitro, particularly in water-based systems.^[31]^[32]

Applications

Research Uses

Trolox serves as a standard reference compound in antioxidant assays, particularly the Oxygen Radical Absorbance Capacity (ORAC) assay, where its scavenging activity against peroxyl radicals is used to quantify the antioxidant capacity of other substances.^[33] The Trolox Equivalent (TE) unit is defined as the antioxidant activity equivalent to 1 μM of Trolox, allowing for standardized comparisons across samples, with results often expressed in μmol TE per gram or liter.^[34] In cell biology research, Trolox is employed to protect cells from reactive oxygen species (ROS)-induced damage in various disease models. It demonstrates neuroprotective effects in ischemia by mitigating oxidative stress and neuronal injury in hippocampal and cortical models.^[35] In neurodegeneration studies, such as those using MPTP to induce Parkinson's-like conditions, Trolox attenuates dopaminergic neuron loss by reducing oxidative stress and neuroinflammation.^[36] For inflammation models, Trolox suppresses ROS-dependent neutrophil extracellular trap formation, highlighting its utility in investigating inflammatory pathways.^[37] Trolox is incorporated into antifade reagents for fluorescence microscopy to minimize photobleaching and phototoxicity during live-cell imaging. Its mechanism involves triplet-state quenching of fluorophores via electron transfer, thereby preserving signal intensity over extended observation periods without significantly altering cellular physiology.^[38] In specialized studies, Trolox inhibits osteoclast formation by suppressing RANKL-induced signaling and reduces interleukin-1 (IL-1)-induced bone loss in mouse calvarial models, providing insights into oxidative stress in bone resorption processes.^[39] Similarly, in stem cell research, Trolox enhances the viability of differentiated embryonic stem cells by alleviating T-2 toxin-induced oxidative damage and apoptosis during differentiation protocols.^[40] Experimental dosages of Trolox typically range from 10 to 100 μM in cell culture for effective ROS scavenging, with concentrations adjusted based on the model to balance antioxidant efficacy and avoid pro-oxidant effects at higher levels.^[41] Its water-soluble nature facilitates uniform distribution and cell permeability in these aqueous-based assays.^[33]

Medical and Therapeutic Potential

Trolox has demonstrated neuroprotective effects in preclinical models of neurodegenerative diseases, primarily by mitigating oxidative damage associated with reactive oxygen species (ROS). In Alzheimer's disease models, Trolox reduces amyloid-beta (Aβ) pathology, neuroinflammation, and synaptic dysfunction in Aβ-induced mouse models, leading to improved cognitive outcomes.^[42] Similarly, in Parkinson's disease models using MPTP to induce dopaminergic neuron loss, Trolox attenuates oxidative stress, neuroinflammation, and motor deficits, preserving neuronal viability.^[36] For stroke, Trolox exhibits protective effects against ischemia-reperfusion injury by scavenging peroxyl radicals and stabilizing mitochondrial function in rodent models.^[43] In cardiovascular health, Trolox inhibits peroxynitrite-mediated endothelial dysfunction, a key contributor to vascular complications in conditions like diabetes and hypertension. By neutralizing peroxynitrite-induced oxidative stress, Trolox preserves nitric oxide bioavailability and reduces endothelial cell apoptosis in isolated vessel models, potentially mitigating atherosclerosis progression.^[21]^[44] Trolox exerts anti-inflammatory effects, particularly in rheumatoid arthritis models, where it suppresses osteoclast activity and bone resorption. In RANKL-induced osteoclastogenesis assays, Trolox inhibits RANKL expression in osteoblasts and c-Fos signaling in precursors, reducing joint inflammation and cartilage degradation in adjuvant-induced arthritis in rats.^[45] Combinations with agents like diosmin further enhance these effects by downregulating NF-κB and pro-inflammatory cytokines.^[46] Regarding cancer, Trolox shows potential as an adjunct to protect healthy cells from chemotherapy-induced oxidative stress without compromising anti-tumor efficacy. In models of arsenic trioxide therapy for lymphoma and leukemia, Trolox selectively enhances cancer cell apoptosis while shielding nonmalignant cells from ROS-mediated cytotoxicity, improving therapeutic index.^[47]^[48] As of 2025, Trolox remains primarily in preclinical and early-phase research, with limited human clinical trials focused on its adjunct role in antioxidant therapies for oxidative stress-related conditions; it has no FDA approval as a standalone therapeutic drug.^[49]^[50] Trolox exhibits a favorable toxicity profile, with low acute toxicity evidenced by an oral LD50 exceeding 4 g/kg in rats, indicating safety at typical research doses up to 100 mg/kg; however, long-term effects, including potential hepatotoxicity at millimolar concentrations, require further investigation.^[51]^[52] Delivery of Trolox presents challenges due to its rapid plasma clearance and limited bioavailability, necessitating formulations such as liposomes or conjugates for effective oral or intravenous administration to achieve sustained therapeutic levels.^[53]^[54]

Synthesis and Production

Laboratory Synthesis

Trolox was first synthesized in 1974 by researchers at Hoffman-La Roche, including John W. Scott and colleagues, as part of efforts to develop water-soluble vitamin E analogs. The compound, 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid, is prepared through methods analogous to those for vitamin E, involving the formation of the chroman ring from hydroquinone derivatives and isoprenoid units, with incorporation of the carboxylic acid at the 2-position.^[55] Laboratory-scale synthesis typically yields a racemic mixture at the chiral C2 center. Purification is achieved by recrystallization from ethanol or silica gel column chromatography.^[56] Variants for obtaining enantiomerically pure Trolox focus on resolution of the racemate. One method involves forming diastereomeric salts with chiral resolving agents such as (1S,2S)-(+)-pseudoephedrine, followed by crystallization and liberation of the free acid, achieving enantiomeric excesses greater than 95%. The (S)-enantiomer exhibits biological activity similar to natural α-tocopherol.^[57]

Commercial Production and Availability

Trolox was originally developed and trademarked by Hoffman-La Roche in 1974 as a water-soluble analog of vitamin E. Currently, it is produced and distributed by multiple chemical suppliers, including Sigma-Aldrich, Cayman Chemical, and Thermo Fisher Scientific, which offer it for research and laboratory use. These vendors synthesize Trolox through established chemical processes adapted for commercial scale, ensuring consistent quality for global distribution.^[55]^[4] Commercial grades of Trolox typically achieve purity levels of ≥97% for research applications, as verified by titration or HPLC methods, while GMP-compliant versions are available for potential pharmaceutical development and clinical evaluations. It is commonly packaged in quantities ranging from 1 g to 100 g, with pricing typically between $80 and $100 per gram as of 2023, depending on quantity and supplier, making it accessible for both academic and industrial users.^[56] Trolox is not classified as a controlled substance and is categorized as a research chemical, with no significant import restrictions in most jurisdictions. In the European Union, it complies with REACH regulations and is exempt from mandatory registration for scientific research uses due to low volumes.^[58]

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