CAS 58186-27-9 Idebenone - Analytical Products / Alfa Chemistry

CAT	APS58186279
CAS	58186-27-9
Structure
MDL Number	MFCD00274552
IUPAC Name	2-(10-hydroxydecyl)-5,6-dimethoxy-3-methylcyclohexa-2,5-diene-1,4-dione
Molecular Weight	338.44
Molecular Formula	C19H30O5
Canonical SMILES	COC1=C(OC)C(=O)C(=C(C)C1=O)CCCCCCCCCCO
InChI	InChI=1S/C19H30O5/c1-14-15(12-10-8-6-4-5-7-9-11-13-20)17(22)19(24-3)18(23-2)16(14)21/h20H,4-13H2,1-3H3
InChI Key	JGPMMRGNQUBGND-UHFFFAOYSA-N

Description	analytical standard
Accurate Mass	338.2093
Assay	≥97.0% (HPLC)
Form	neat; gas chromatography (GC): suitable
Format	Neat
Grade	analytical standard
Shipping	Room Temperature
Size	10MG
Storage Conditions	-20°C Freezer
Subcategory	Quinones

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Case Study

Idebenone Used for the Preparation of Solid Lipid Nanoparticles for Topical Antioxidant Applications

Montenegro, L., Sinico, C., Castangia, I., Carbone, C., & Puglisi, G. (2012). International journal of pharmaceutics, 434(1-2), 169-174.

Idebenone (IDE), a synthetic analogue of coenzyme Q10, exhibits powerful antioxidant properties and has attracted significant interest for the topical treatment of oxidative skin damage. In this study, IDE was effectively encapsulated into solid lipid nanoparticles (SLNs) to enhance dermal delivery and antioxidant efficacy in the upper skin layers.
SLNs were prepared using the phase inversion temperature (PIT) method, employing cetyl palmitate as the solid lipid matrix and three different non-ionic surfactants-ceteth-20, isoceteth-20, and oleth-20-to stabilize the formulation. The PIT method involved separately heating the oil and aqueous phases to ~90 °C, followed by dropwise emulsification and gradual cooling under continuous agitation. Conductivity measurements were employed to identify PIT values, confirming the transition from water-in-oil to oil-in-water systems.
The incorporation of varying concentrations of Idebenone into the SLNs yielded stable, nanoscale dispersions. Thin-layer chromatography (TLC) analysis confirmed the chemical integrity of IDE during processing, indicating no detectable degradation. The formulation preserved IDE's functionality, providing a promising delivery platform for targeted antioxidant therapy.
This study demonstrates the feasibility of formulating Idebenone-loaded SLNs using mild, surfactant-based systems to optimize topical administration and combat skin oxidative stress effectively.

Idebenone Used for the Preparation of Long-Acting Intravitreal Implants for Leber's Hereditary Optic Neuropathy

Varela-Fernández, Rubén, et al. European Journal of Pharmaceutics and Biopharmaceutics 168 (2021): 195-207.

Idebenone, a potent synthetic antioxidant structurally related to coenzyme Q10, has shown therapeutic potential for mitochondrial dysfunctions such as Leber's Hereditary Optic Neuropathy (LHON). In this pilot study, long-acting intravitreal implants were developed to achieve sustained and controlled Idebenone delivery to the posterior segment of the eye.
The implants were prepared using a homogenization/extrusion/solvent evaporation technique, incorporating poly-ε-caprolactone (PCL) as the biodegradable matrix. Physical premixing of Idebenone and PCL at varying drug-to-polymer ratios (1:1, 1:5, and 1:10) ensured homogeneity. The blend was dissolved in dichloromethane, magnetically stirred, and extruded through capillary tubes using a syringe fitted with a 22G needle. Subsequent vacuum drying under controlled pressure gradients facilitated solvent removal and solidification.
The resulting Idebenone-loaded PCL implants exhibited high production yields (PY), encapsulation efficiencies (EE), and drug-loading capacities (LC), indicating excellent formulation performance. The implants were designed to support prolonged Idebenone release, potentially overcoming the limitations of frequent intravitreal injections and enhancing patient compliance in the management of LHON.
This study highlights the feasibility of developing long-term Idebenone delivery systems via biodegradable implants, providing a promising strategy for targeted neuroprotective therapy in retinal mitochondrial disorders.

Idebenone Used for the Preparation of Stock and Calibration Solutions in a Stability-Indicating HPLC Method

Kombath, Sonoube, et al. Journal of Analytical Methods in Chemistry 2015.1 (2015): 835986.

Idebenone, a coenzyme Q10-like compound with therapeutic antioxidant properties, requires precise quantification in pharmaceutical formulations. A stability-indicating HPLC method was developed, with a strong emphasis on the accuracy and reproducibility of solution preparation.
For the preparation of the stock solution, 10 g of idebenone was accurately weighed and transferred to a 100 mL volumetric flask. The volume was adjusted to the mark with methanol, yielding a 100 mg/mL idebenone stock solution, which was stored at 2-8 °C for up to 5 days to maintain stability.
Sample preparation involved crushing two idebenone 45 mg tablets into a fine powder, followed by suspension in 5 mL of methanol. The mixture was quantitatively transferred to a 10 mL volumetric flask and diluted to volume with methanol, resulting in a 9 mg/mL sample solution. This approach ensured excellent recovery (100.4 ± 0.3%), confirming the method's robustness.
For calibration and quality control, standard solutions were freshly prepared from the stock solution at concentrations of 3.0-8.0 mg/mL. Quality control solutions at 3.5, 4.5, and 6.5 mg/mL were similarly prepared extemporaneously.
This meticulous solution preparation protocol underpins the accuracy and reliability of the HPLC method, ensuring its suitability for idebenone quantification in pharmaceutical quality control.