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58186-27-9,MFCD00274552
Catalog No.:AA00IAA2

58186-27-9 | 2-(10-hydroxydecyl)-5,6-dimethoxy-3-methylcyclohexa-2,5-diene-1,4-dione

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50mg
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1g
98%(HPLC)
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5g
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10g
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$153.00   $107.00
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25g
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100g
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA00IAA2
Chemical Name:
2-(10-hydroxydecyl)-5,6-dimethoxy-3-methylcyclohexa-2,5-diene-1,4-dione
CAS Number:
58186-27-9
Molecular Formula:
C19H30O5
Molecular Weight:
338.4385
MDL Number:
MFCD00274552
SMILES:
OCCCCCCCCCCC1=C(C)C(=O)C(=C(C1=O)OC)OC
NSC Number:
759228
Properties
Computed Properties
 
Complexity:
502  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
24  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
1  
Rotatable Bond Count:
12  
XLogP3:
4.3  

Downstream Synthesis Route

[1]Patent:FR2269333,1975,    Patent:DE2519730,1975,    Chem.Abstr.,1976,vol.84

[1]BulletinoftheChemicalSocietyofJapan,1984,vol.57,p.3182-3196

[2]ChemicalandPharmaceuticalBulletin,1985,vol.33,p.3756-3765

[3]Patent:FR2269333,1975,    Patent:DE2519730,1975,    Chem.Abstr.,1976,vol.84

[1]Patent:US2010/76077,2010,A1.Locationinpatent:Page/Pagecolumn3

[2]ChemicalandPharmaceuticalBulletin,1988,vol.36,p.178-189

[3]Patent:WO2012/22467,2012,A2.Locationinpatent:Page/Pagecolumn62-63

[1]ChemicalandPharmaceuticalBulletin,1988,vol.36,p.178-189

[2]ChemicalandPharmaceuticalBulletin,1988,vol.36,p.178-189

[1]Patent:WO2013/60673,2013,A1.Locationinpatent:Page/Pagecolumn55

[2]Patent:WO2014/63923,2014,A1.Locationinpatent:Page/Pagecolumn51

[3]ChemicalandPharmaceuticalBulletin,1985,vol.33,p.3745-3755

[4]Patent:WO2012/22467,2012,A2.Locationinpatent:Page/Pagecolumn56

Literature

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Title: Is Leber hereditary optic neuropathy treatable? Encouraging results with idebenone in both prospective and retrospective trials and an illustrative case.

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Title: Idebenone-induced recovery of glycerol-3-phosphate and succinate oxidation inhibited by digitonin.

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Title: In vitro evaluation on a model of blood brain barrier of idebenone-loaded solid lipid nanoparticles.

Journal: Journal of nanoscience and nanotechnology 20120101

Title: Features of idebenone and related short-chain quinones that rescue ATP levels under conditions of impaired mitochondrial complex I.

Journal: PloS one 20120101

Title: Determination of idebenone in plasma by HPLC with post-column fluorescence derivatization using 2-cyanoacetamide.

Journal: Chemical & pharmaceutical bulletin 20120101

Title: Idebenone protects against retinal damage and loss of vision in a mouse model of Leber's hereditary optic neuropathy.

Journal: PloS one 20120101

Title: Effect of long-term oral treatment with L-arginine and idebenone on the prevention of stroke-like episodes in an adult MELAS patient.

Journal: Revue neurologique 20111101

Title: Idebenone induces apoptotic cell death in the human dopaminergic neuroblastoma SHSY-5Y cells.

Journal: Neurotoxicity research 20111101

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Title: Treatment of Leber hereditary optic neuropathy.

Journal: Brain : a journal of neurology 20110901

Title: Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.

Journal: Journal of medicinal chemistry 20110714

Title: Idebenone inhibition of glutamate release from rat cerebral cortex nerve endings by suppression of voltage-dependent calcium influx and protein kinase A.

Journal: Naunyn-Schmiedeberg's archives of pharmacology 20110701

Title: α-Tocotrienol quinone modulates oxidative stress response and the biochemistry of aging.

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Journal: Drug development and industrial pharmacy 20110601

Title: Idebenone as a novel, therapeutic approach for Duchenne muscular dystrophy: results from a 12 month, double-blind, randomized placebo-controlled trial.

Journal: Neuromuscular disorders : NMD 20110601

Title: Effects of liposomal encapsulation on the antioxidant activity of lipophilic prodrugs of idebenone.

Journal: Journal of liposome research 20110301

Title: Combined therapy with idebenone and deferiprone in patients with Friedreich's ataxia.

Journal: Cerebellum (London, England) 20110301

Title: Idebenone in Friedreich ataxia cardiomyopathy-results from a 6-month phase III study (IONIA).

Journal: American heart journal 20110301

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Journal: Reviews in neurological diseases 20110101

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Journal: Current medicinal chemistry 20110101

Title: Idebenone and resveratrol extend lifespan and improve motor function of HtrA2 knockout mice.

Journal: PloS one 20110101

Title: Antioxidant idebenone-loaded nanoparticles based on chitosan and N-carboxymethylchitosan.

Journal: Nanomedicine : nanotechnology, biology, and medicine 20101201

Title: Pharmacokinetic evaluation of idebenone.

Journal: Expert opinion on drug metabolism & toxicology 20101101

Title: Synthesis and characterization of mitoQ and idebenone analogues as mediators of oxygen consumption in mitochondria.

Journal: Bioorganic & medicinal chemistry 20100901

Title: Nitric oxide pros and cons: The role of L-arginine, a nitric oxide precursor, and idebenone, a coenzyme-Q analogue in ameliorating cerebral hypoxia in rat.

Journal: Brain research bulletin 20100830

Title: A phase 3, double-blind, placebo-controlled trial of idebenone in friedreich ataxia.

Journal: Archives of neurology 20100801

Title: Exercise capacity and idebenone intervention in children and adolescents with Friedreich ataxia.

Journal: Archives of physical medicine and rehabilitation 20100701

Title: Intermediate-dose idebenone and quality of life in Friedreich ataxia.

Journal: Pediatric neurology 20100501

Title: Treatment of mitochondrial electron transport chain disorders: a review of clinical trials over the past decade.

Journal: Molecular genetics and metabolism 20100301

Title: Coenzyme Q10 in neuromuscular and neurodegenerative disorders.

Journal: Current drug targets 20100101

Title: Emergent and unusual allergens in cosmetics.

Journal: Dermatitis : contact, atopic, occupational, drug 20100101

Title: Treatment of CoQ(10) deficient fibroblasts with ubiquinone, CoQ analogs, and vitamin C: time- and compound-dependent effects.

Journal: PloS one 20100101

Title: [The use of noben (idebenone) in the complex treatment of episodic and chronic migraine].

Journal: Zhurnal nevrologii i psikhiatrii imeni S.S. Korsakova 20100101

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Title: Antioxidants and other pharmacological treatments for Friedreich ataxia.

Journal: The Cochrane database of systematic reviews 20091007

Title: Neurophysiological evaluation in children with Friedreich's ataxia.

Journal: Early human development 20091001

Title: Low-dose idebenone treatment in Friedreich's ataxia with and without cardiac hypertrophy.

Journal: Journal of neurology 20090901

Title: Characterizing gait, locomotor status, and disease severity in children and adolescents with Friedreich ataxia.

Journal: Journal of neurologic physical therapy : JNPT 20090901

Title: Use of Noben (idebenone) in the treatment of dementia and memory impairments without dementia.

Journal: Neuroscience and behavioral physiology 20090601

Title: Pharmacokinetics and metabolism of idebenone in healthy male subjects.

Journal: European journal of clinical pharmacology 20090501

Title: Efficacy of idebenone for respiratory failure in a patient with Leigh syndrome: a long-term follow-up study.

Journal: Journal of the neurological sciences 20090315

Title: Investigating idebenone and idebenone linoleate metabolism: in vitro pig ear and mouse melanocyte studies.

Journal: Journal of cosmetic dermatology 20090301

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Title: Long-term blinded placebo-controlled study of SNT-MC17/idebenone in the dystrophin deficient mdx mouse: cardiac protection and improved exercise performance.

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Journal: Contact dermatitis 20080401

Title: Allergic contact dermatitis to hydroxydecyl ubiquinone: a newly described contact allergen in cosmetics.

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Journal: The Lancet. Neurology 20071001

Title: A comparison of the relative antioxidant potency of L-ergothioneine and idebenone.

Journal: Journal of cosmetic dermatology 20070901

Title: Protective effects of Fe-Aox29, a novel antioxidant derived from a molecular combination of Idebenone and vitamin E, in immortalized fibroblasts and fibroblasts from patients with Friedreich Ataxia.

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Title: Friedreich's ataxia: coenzyme Q10 and vitamin E therapy.

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Title: Neurological, cardiological, and oculomotor progression in 104 patients with Friedreich ataxia during long-term follow-up.

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Title: Allergic contact dermatitis to idebenone used as an antioxidant in an anti-wrinkle cream.

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Title: A calorimetric evaluation of the interaction of amphiphilic prodrugs of idebenone with a biomembrane model.

Journal: Journal of colloid and interface science 20060715

Title: Protective properties of idebenone in noise-induced hearing loss in the guinea pig.

Journal: Neuroreport 20060626

Title: Effect of oil phase lipophilicity on in vitro drug release from o/w microemulsions with low surfactant content.

Journal: Drug development and industrial pharmacy 20060601

Title: Ubiquinone, idebenone, and kinetin provide ineffective photoprotection to skin when compared to a topical antioxidant combination of vitamins C and E with ferulic acid.

Journal: The Journal of investigative dermatology 20060501

Title: Microsphere-based protease assays and screening application for lethal factor and factor Xa.

Journal: Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501

Title: Inhibition of glycerophosphate-dependent H2O2 generation in brown fat mitochondria by idebenone.

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Title: Progression despite replacement of a myopathic form of coenzyme Q10 defect.

Journal: Neurology 20040824

Title: Tolerability and improved protective action of idebenone-loaded pegylated liposomes on ethanol-induced injury in primary cortical astrocytes.

Journal: Journal of pharmaceutical sciences 20040701

Title: Idebenone delays the onset of cardiac functional alteration without correction of Fe-S enzymes deficit in a mouse model for Friedreich ataxia.

Journal: Human molecular genetics 20040515

Title: Quinone analogues regulate mitochondrial substrate competitive oxidation.

Journal: Biochemical and biophysical research communications 20040416

Title: Cerebrospinal fluid concentrations of idebenone in Friedreich ataxia patients.

Journal: Neuropediatrics 20040401

Title: Chemical and enzymatic stability evaluation of lipoamino acid esters of idebenone.

Journal: European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V 20040301

Title: Idebenone treatment in Friedreich patients: one-year-long randomized placebo-controlled trial.

Journal: Neurology 20040210

Title: Idebenone treatment fails to slow cognitive decline in Alzheimer's disease.

Journal: Neurology 20031209

Title: Cytosolic and mitochondrial ROS in staurosporine-induced retinal cell apoptosis.

Journal: Free radical biology & medicine 20031201

Title: Mitochondria-targeted antioxidants protect Friedreich Ataxia fibroblasts from endogenous oxidative stress more effectively than untargeted antioxidants.

Journal: FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20031001

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Journal: Orvosi hetilap 20030622

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Journal: Neurology 20030527

Title: Idebenone treatment in Friedreich's ataxia: neurological, cardiac, and biochemical monitoring.

Journal: Neurology 20030527

Title: A cellular model for Friedreich Ataxia reveals small-molecule glutathione peroxidase mimetics as novel treatment strategy.

Journal: Human molecular genetics 20021115

Title: Ethanol-induced injury in rat primary cortical astrocytes involves oxidative stress: effect of idebenone.

Journal: Neuroscience letters 20020823

Title: Friedreich's ataxia: idebenone treatment in early stage patients.

Journal: Neuropediatrics 20020801

Title: Molecular insights into Friedreich's ataxia and antioxidant-based therapies.

Journal: Trends in molecular medicine 20020501

Title: Idebenone and reduced cardiac hypertrophy in Friedreich's ataxia.

Journal: Heart (British Cardiac Society) 20020401

Title: Heart hypertrophy and function are improved by idebenone in Friedreich's ataxia.

Journal: Free radical research 20020401

Title: Monitoring of idebenone treatment in patients with Friedreich's ataxia by high-pressure liquid chromatography with electrochemical detection.

Journal: Journal of neuroscience methods 20020330

Title: Safety and efficacy of idebenone versus tacrine in patients with Alzheimer's disease: results of a randomized, double-blind, parallel-group multicenter study.

Journal: Pharmacopsychiatry 20020101

Title: Improved antioxidant effect of idebenone-loaded polyethyl-2-cyanoacrylate nanocapsules tested on human fibroblasts.

Journal: Pharmaceutical research 20020101

Title: Coenzyme Q(10) and idebenone in the therapy of respiratory chain diseases: rationale and comparative benefits.

Journal: Molecular genetics and metabolism 20020101

Title: Leber's hereditary optic neuropathy (LHON/11778) with myoclonus: report of two cases.

Journal: Journal of neurology, neurosurgery, and psychiatry 20011201

Title: [Delayed apoptosis and its regulation in astrocytes].

Journal: Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan 20010901

Title: Idebenone in patients with Friedreich ataxia.

Journal: Neuroscience letters 20010629

Title: Idebenone - monograph.

Journal: Alternative medicine review : a journal of clinical therapeutic 20010201

Title: Dramatic improvement in mitochondrial cardiomyopathy following treatment with idebenone.

Journal: Journal of inherited metabolic disease 20010201

Title: Vitamin E prevents apoptosis in cortical neurons during hypoxia and oxygen reperfusion.

Journal: Laboratory investigation; a journal of technical methods and pathology 19981101

Title: Idebenone. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic use in age-related cognitive disorders.

Journal: Drugs & aging 19940801

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Tags:58186-27-9 Molecular Formula|58186-27-9 MDL|58186-27-9 SMILES|58186-27-9 2-(10-hydroxydecyl)-5,6-dimethoxy-3-methylcyclohexa-2,5-diene-1,4-dione