2-(10-hydroxydecyl)-5,6-dimethoxy-3-methylcyclohexa-2,5-diene-1,4-dione

• ChemBase ID: 73274
• Molecular Formular: C19H30O5
• Molecular Mass: 338.4385
• Monoisotopic Mass: 338.20932406
• SMILES: C1(=O)C(=C(C(=O)C(=C1C)CCCCCCCCCCO)OC)OC
• Canonical SMILES: OCCCCCCCCCCC1=C(C)C(=O)C(=C(C1=O)OC)OC
• 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
• InChIKey: JGPMMRGNQUBGND-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(10-hydroxydecyl)-5,6-dimethoxy-3-methylcyclohexa-2,5-diene-1,4-dione
• IUPAC Traditional name: idebenone; 2-(10-hydroxydecyl)-5,6-dimethoxy-3-methylcyclohexa-2,5-diene-1,4-dione
• Synonyms: Idebenone; Cerestabon; Esanic; Geniceral; Idesol; Lucenabol; Nemocebral; Idebenone; 2-(10-Hydroxydecyl)-5,6-methoxy-3-methyl-2,5-cyclohexadiene-1,4-dione; 2,3-Dimethoxy-6-(10-hydroxydecyl)-5-methyl-1,4-benzoquinone; Avan; CV 2619; Daruma; Mnesis; 2-(10-hydroxydecyl)-5,6-dimethoxy-3-methylcyclohexa-2,5-diene-1,4-dione; Idebenone; 5,6-Dimethoxy-2-(10-hydroxydecyl)-3-methyl-1,4-benzoquinone

Database IDs

• CAS Number: 58186-27-9
• MDL Number: MFCD00274552
• PubChem SID: 162038194
• PubChem CID: 3686

CALCULATED PROPERTIES

• Acid pKa: 16.843943
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 3.5679936
• LogD (pH = 7.4): 3.5679936
• Log P: 3.5679936
• Molar Refractivity: 96.5179 cm^3
• Polarizability: 36.67194 Å^3
• Polar Surface Area: 72.83 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Yellow-Orange Solid
• Melting Point: 52-55°C

Safety Information

• Storage Condition: -20°C; Amber Vial, -20°C Freezer
• Storage Warning: Irritant

Pharmacology Properties

• Mechanism of Action: Free radical scavenger

Product Information

• Salt Data: Free Base
• Application(s): Cardiovascular agent; Drug for enhancement of immune response; Neuroprotective agent; Nootropic

DETAILS

Selleck Chemicals - S2605

Biological Activity:
Idebenone is a synthetic analog of coenzyme Q10 (CoQ10) and a brain stimulant. Idebenone is used for the treatment of Alzheimer’s disease and other cognitive defects. Idebenone is inhibits lipoperoxide formation.is a synthetic analog of coenzyme Q10 (CoQ10). Idebenone increases brain energy levels and rejuvinates cell mitochondria throughout the whole body. Most recently, idebenone has been shown to be very supportive in the treatment of Friedreich’s ataxia and Duchenne muscular dystrophy. Chemically, idebenone is an organic compound of the quinone family. Idebenone has properties similar to CoQ10 in its antioxidant properties, and has therefore been used in anti-aging on the basis of free-radical theory. [1][2][3]References on Idebenone[1] Nippon Yakurigaku Zasshi. , 1988 May, 91(5):295-9[2] http://en.wikipedia.org/wiki/Idebenone, , [3] Lancet Neurol., 2007 Oct, 6(10):878-86

Toronto Research Chemicals - I170050

Ubiquinone derivative with protective effects against cerebral ischemia. Nootropic.

REFERENCES

• Di Prospero NA et al. Lancet Neurol. 2007 Oct;6(10):878-86.
• Barkworth, M.F., et al.: Arzneim.-Forsch., 35, 1704 (1985)
• Kobayashi, T., et al.: J. Pharmacobio-Dyn., 8, 448 (1985)
• Zs-Nagy, I., et al.: Arch. Gerontol. Geriatr., 11, 177 (1985)
• Ger. Pat., 1975, Takeda, 2 519 730; CA, 84, 58928j, (synth)
• Okamoto, K. et al., Chem. Pharm. Bull., 1982, 30, 2797
• Naguoka, A. et al., Jpn. J. Pharmacol., 1984, 36, 291
• Morimoto, H., Naturwissenschaften, 1989, 76, 200, (synth)
• Wakabayashi, H. et al., J. Chromatogr., 1992, 573, 154, (hplc)
• Naito, M. et al., Artery (Leonidas, Mich.), 1993, 20, 314, (pharmacol)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 1227
• Gillis, J.C. et al., Drugs Aging, 1994, 5, 133, (rev)
• Bruno, V. et al., Neurosci. Lett., 1994, 178, 193, (pharmacol)
• Jung, Y.-S. et al., Synth. Commun., 2001, 31, 2735-2741, (synth, pmr, cmr)