Idebenone

Base Information

• Chemical Name: Idebenone
• CAS No.: 58186-27-9
• Molecular Formula: C19H30O5
• Molecular Weight: 338.444
• Hs Code.: 2933399990
• European Community (EC) Number: 814-253-7
• NSC Number: 759228
• UNII: HB6PN45W4J
• DSSTox Substance ID: DTXSID0040678
• Nikkaji Number: J22.706D
• Wikipedia: Idebenone
• Wikidata: Q4197874
• NCI Thesaurus Code: C74158
• Pharos Ligand ID: 1UY851FM8LZR
• Metabolomics Workbench ID: 87109
• ChEMBL ID: CHEMBL252556
• Mol file: 58186-27-9.mol

Synonyms:CV 2619;CV-2619;hydroxydecyl ubiquinone;idebenone;noben;Raxone

Chemical Property of Idebenone

Chemical Property:

• Appearance/Colour: Yellow-orange crystalline powder
• Vapor Pressure: 5.67E-12mmHg at 25°C
• Melting Point: 52-55 °C
• Refractive Index: 1.502
• Boiling Point: 497.3 °C at 760 mmHg
• PKA: 15.20±0.10(Predicted)
• Flash Point: 170.1 °C
• PSA: 72.83000
• Density: 1.08 g/cm³
• LogP: 3.46230
• Storage Temp.: Room temp
• Solubility.: Soluble in DMSO (up to 25 mg/ml).
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 12
• Exact Mass: 338.20932405
• Heavy Atom Count: 24
• Complexity: 502

Purity/Quality:

99% ^*data from raw suppliers

Idebenone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(=O)C(=C(C1=O)OC)OC)CCCCCCCCCCO
• Recent ClinicalTrials: Study to Assess the Safety and Tolerability of Idebenone in the Treatment of Friedreich's Ataxia Patients
• Recent EU Clinical Trials: Raxone? treatment for patients with dominant optic atrophy due to OPA1 gene mutation
• Recent NIPH Clinical Trials: Multicenter study of therapeutic effects of Idebenone in patients with Leber hereditary optic neuropathy
• General Description: Idebenone is a synthetic benzoquinone compound with demonstrated neuroprotective and antioxidant properties. It functions as an electron carrier in the mitochondrial respiratory chain, enhancing cellular energy metabolism, and exhibits antioxidant effects by inhibiting lipid peroxidation in mitochondrial and microsomal membranes. Studies suggest its potential in mitigating vascular disorders and ischemia-related metabolic dysfunction, with research focusing on optimizing its derivatives for prolonged activity and improved metabolic stability.

Technology Process of Idebenone

There total 37 articles about Idebenone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

10-(2,3,4-trimethoxy-6-methylphenyl)decan-1-ol (1286209-74-2) → Idebenone (58186-27-9)

Guidance literature:

With ammonium peroxydisulfate; nitric acid; In water; acetone; at 50 ℃; for 2.16h;

Reference yield: 96.9%

disodium nitrosodisulfonate + 6-(10-hydroxydecyl)-2,3-dimethoxy-5-methylphenol (77712-29-9) → Idebenone (58186-27-9)

Guidance literature:

In methanol; water;

Reference yield: 87.0%

6-(10-hydroxydecyl)-2,3-dimethoxy-5-methylphenol (77712-29-9) → Idebenone (58186-27-9)

Guidance literature:

With oxygen; salcomine; In N,N-dimethyl-formamide; for 72h; Ambient temperature;

DOI:10.1248/cpb.33.4422

upstream raw materials:

2,3-dimethoxy-5-methyl-6-(9'-methoxycarbonylnonyl)-1,4-benzoquinone

6-(10-hydroxydecyl)-2,3-dimethoxy-5-methylphenol

2,3-dimethoxy-5-methyl-6-(10'-acetoxydecyl)-1,4-benzoquinone

methyl 10-chloro-10-oxodecanoate

Downstream raw materials:

10-(2,3-Dimethoxy-5-methyl-1,4-benzoquinon-6-yl)decanoic acid

6-(10-hydroxydecyl)-3-methoxy-5-methyl-1,4-benzoquinone

6-(10-hydroxydecyl)-2-methoxy-5-methyl-1,4-benzoquinone

2-hydroxy-6-(10-hydroxydecyl)-3-methoxy-5-methyl-1,4-benzoquinone

Refernces

Synthesis, metabolism, and in vitro biological activities of 6-(10-hydroxydecyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone (CV-2619)-related compounds

10.1248/cpb.36.178

The study investigates the synthesis, metabolism, and in vitro biological activities of 6-(10-hydroxydecyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone (CV-2619) and its related compounds. CV-2619 has been reported to suppress renal and cerebral vascular disorders in stroke-prone spontaneously hypertensive rats and alleviate abnormal energy metabolism induced by cerebral ischemia. Its in vitro biological activities include electron transfer activity in the mitochondrial respiratory chain and antioxidant activity in mitochondrial and microsomal membranes. The study synthesizes demethyl derivatives (3a, 3b, and 4) and compounds with modified hydroxyalkyl chains (13, 20, 21, 23a, and 23b) for metabolic studies and biological activity evaluation. In rats, compounds 13 and trans-23a are metabolized more slowly than CV-2619. Except for the demethyl derivatives, these compounds show comparable electron transfer effects to CV-2619 in the succinate oxidation system and inhibit lipid peroxidation in rat liver homogenate. The study aims to develop derivatives with prolonged plasma levels and maintained biological activities.