Mitoquinone mesylate

Synonyme: MitoQ, Mitoquinol mesylate, Mitoquinone mesylate, (10-(4,5-Dimethoxy-2-methyl-3,6-dioxo-1,4-cyclohexadien-1-yl)decyl)triphenylphosphonium mesylate

Mitoquinone mesylate is a synthetic derivative of coenzyme Q10 (ubiquinone) engineered to accumulate within mitochondria. Its structure couples a quinone redox core to a ten-carbon aliphatic chain terminated by a triphenylphosphonium (TPP⁺) cation. This lipophilic cation drives rapid electrophoretic uptake across the mitochondrial inner membrane, where the membrane potential (Δψ_m) is highly negative. The result is a mitochondria-targeted antioxidant that concentrates several hundred-fold inside the organelle, far exceeding the distribution of native CoQ10.

As a research chemical, Mitoquinone mesylate is supplied as the mesylate salt to improve aqueous solubility and handling stability. It is widely used in cellular and animal models to interrogate mitochondrial oxidative stress, redox signaling, and bioenergetics. Typical applications include studies on aging, neurodegeneration, cardiovascular ischemia-reperfusion injury, and metabolic disorders.

In the pharmaceutical and nutraceutical supply chain, Mitoquinone mesylate is recognized as a high-value active pharmaceutical ingredient (API) candidate and a reference standard for analytical method development. Its synthesis involves a multi-step route that demands strict control over purity, residual solvents, and counterion stoichiometry. LyvBio provides Mitoquinone mesylate with full analytical documentation, supporting formulation development and preclinical research.

Chemical Structure & Properties

The molecule consists of a 2,3-dimethoxy-5-methyl-1,4-benzoquinone headgroup linked via a decyl chain to a triphenylphosphonium moiety. The mesylate counterion (CH₃SO₃^–) balances the positive charge, yielding a crystalline solid with improved water dispersibility compared to the free base. The compound is sensitive to light and reducing agents; storage under inert gas at low temperature is recommended to prevent quinone reduction or degradation.

Mechanism of Action

• Mitochondrial targeting: The TPP⁺ cation undergoes potential-driven accumulation across the inner mitochondrial membrane, achieving concentrations up to 500-fold higher than in the cytosol.
• Redox cycling: The quinone core is reduced by complex I or II to the active ubiquinol form, which scavenges superoxide and peroxynitrite, then is reoxidized, allowing catalytic antioxidant turnover.
• Electron transport chain support: Mitoquinone can bypass damaged respiratory complexes, maintaining ATP production under oxidative stress.
• Redox signaling modulation: By altering mitochondrial reactive oxygen species (ROS) levels, it influences Nrf2, NF-κB, and HIF-1α pathways, affecting inflammation and cell survival.

Quality Specifications

Supply & Documentation

• Capacity: 10 kg per month (GMP-compliant production)
• Lieferzeit: 3–5 Werktage (Lagerware)
• Dokumentation: COA, MSDS, TDS, HPLC chromatogram, NMR spectrum, residual solvent report
• Verpackung: Amber glass vials under argon; bulk orders in aluminum foil bags or fiber drums

Angebotsanfrage

• LyvBio GmbH. — E-Mail: info@lyvbio.com