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3066-90-8,MFCD00017161
Catalog No.:AA0030PO

3066-90-8 | 2,3-Dimethoxy-5-methylhydroquinone

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250mg
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1g
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5g
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$397.00   $278.00
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10g
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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:
AA0030PO
Chemical Name:
2,3-Dimethoxy-5-methylhydroquinone
CAS Number:
3066-90-8
Molecular Formula:
C9H12O4
Molecular Weight:
184.1892
MDL Number:
MFCD00017161
SMILES:
COc1c(O)cc(c(c1OC)O)C
Properties
Computed Properties
 
Complexity:
162  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
13  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
2  
Rotatable Bond Count:
2  
XLogP3:
1  

Downstream Synthesis Route

[1]HelveticaChimicaActa,2005,vol.88,p.2575-2581

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[10]JournalofgeneralchemistryoftheUSSR,1968,vol.38,p.453-456    ZhurnalObshcheiKhimii,1968,vol.38,p.459-462

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[1]Kozhukhova,A.I.;Obol'nikova,E.A.;Kozlova,I.V.;Bekker,A.R.;Filippova,T.M.;Samokhvalov,G.I.[JournalofOrganicChemistryUSSR(EnglishTranslation),1982,vol.18,p.2024-2026][ZhurnalOrganicheskoiKhimii,1982,vol.18,#11,p.2292-2295]

3066-90-8    1113-21-9   
CoenzymQ4 

[1]JournalofgeneralchemistryoftheUSSR,1968,vol.38,p.453-456    ZhurnalObshcheiKhimii,1968,vol.38,p.459-462

[1]Tetrahedron,1998,vol.54,p.1241-1253

[2]Chemistry-AnAsianJournal,2011,vol.6,p.1064-1073

[3]Tetrahedron,1996,vol.52,p.7265-7276

[4]JournaloftheAmericanChemicalSociety,1999,vol.121,p.11664-11673

[5]BioorganicandMedicinalChemistryLetters,2005,vol.15,p.1125-1129

[6]OrganicandBiomolecularChemistry,2004,vol.2,p.2371-2375

[7]Patent:US2008/200732,2008,A1.Locationinpatent:Page/Pagecolumn15

[8]Patent:US2008/200732,2008,A1.Locationinpatent:Page/Pagecolumn15-16

[9]Tetrahedron,2011,vol.67,p.5990-6000

[10]JournaloftheAmericanChemicalSociety,2011,vol.133,p.12366-12369

Literature

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Title: Impact of oral ubiquinol on blood oxidative stress and exercise performance.

Journal: Oxidative medicine and cellular longevity 20120101

Title: Composition of the defensive secretion in three species of European millipedes.

Journal: Journal of chemical ecology 20111201

Title: Nitrite as a mediator of ischemic preconditioning and cytoprotection.

Journal: Nitric oxide : biology and chemistry 20110801

Title: Rosuvastatin combined with regular exercise preserves coenzyme Q10 levels associated with a significant increase in high-density lipoprotein cholesterol in patients with coronary artery disease.

Journal: Atherosclerosis 20110701

Title: Physiological importance of cytochrome c peroxidase in ethanologenic thermotolerant Zymomonas mobilis.

Journal: Journal of molecular microbiology and biotechnology 20110401

Title: Renal preservation effect of ubiquinol, the reduced form of coenzyme Q10.

Journal: Clinical and experimental nephrology 20110201

Title: Ubiquinol formation in isolated photosynthetic reaction centres monitored by time-resolved differential FTIR in combination with 2D correlation spectroscopy and multivariate curve resolution.

Journal: Analytical and bioanalytical chemistry 20110201

Title: Ubiquinol (QH(2)) functions as a negative regulator of purine nucleotide inhibition of Acanthamoeba castellanii mitochondrial uncoupling protein.

Journal: Biochimica et biophysica acta 20110101

Title: Altered redox status of coenzyme Q9 reflects mitochondrial electron transport chain deficiencies in Caenorhabditis elegans.

Journal: Mitochondrion 20110101

Title: Ubiquinol-induced gene expression signatures are translated into altered parameters of erythropoiesis and reduced low density lipoprotein cholesterol levels in humans.

Journal: IUBMB life 20110101

Title: Ubiquinol-binding site in the alternative oxidase: mutagenesis reveals features important for substrate binding and inhibition.

Journal: Biochimica et biophysica acta 20101201

Title: The quinone-binding sites of the cytochrome bo3 ubiquinol oxidase from Escherichia coli.

Journal: Biochimica et biophysica acta 20101201

Title: Ubiquinol-10 and ubiquinone-10 levels in umbilical cord blood of healthy foetuses and the venous blood of their mothers.

Journal: Free radical research 20101101

Title: The reduced form of coenzyme Q10 mediates distinct effects on cholesterol metabolism at the transcriptional and metabolite level in SAMP1 mice.

Journal: IUBMB life 20101101

Title: Essential role of copper in the activity and regular periodicity of a recombinant, tumor-associated, cell surface, growth-related and time-keeping hydroquinone (NADH) oxidase with protein disulfide-thiol interchange activity (ENOX2).

Journal: Journal of bioenergetics and biomembranes 20101001

Title: Characterization of the semiquinone radical stabilized by the cytochrome aa3-600 menaquinol oxidase of Bacillus subtilis.

Journal: The Journal of biological chemistry 20100611

Title: Tunneling effect in regeneration reaction of vitamin E by ubiquinol.

Journal: The journal of physical chemistry. B 20100520

Title: Purification and kinetic characterization of recombinant alternative oxidase from Trypanosoma brucei brucei.

Journal: Biochimica et biophysica acta 20100401

Title: Modifications of protein environment of the [2Fe-2S] cluster of the bc1 complex: effects on the biophysical properties of the rieske iron-sulfur protein and on the kinetics of the complex.

Journal: The Journal of biological chemistry 20100319

Title: RegB kinase activity is controlled in part by monitoring the ratio of oxidized to reduced ubiquinones in the ubiquinone pool.

Journal: mBio 20100101

Title: Toward a rational design of multitarget-directed antioxidants: merging memoquin and lipoic acid molecular frameworks.

Journal: Journal of medicinal chemistry 20091210

Title: Converting NADH to NAD+ by nicotinamide nucleotide transhydrogenase as a novel strategy against mitochondrial pathologies during aging.

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Title: Theoretical analysis of the unusual temperature dependence of the kinetic isotope effect in quinol oxidation.

Journal: Journal of the American Chemical Society 20090527

Title: The rate-limiting step in the cytochrome bc1 complex (Ubiquinol-Cytochrome c Oxidoreductase) is not changed by inhibition of cytochrome b-dependent deprotonation: implications for the mechanism of ubiquinol oxidation at center P of the bc1 complex.

Journal: The Journal of biological chemistry 20090522

Title: The Electron Transfer Pathway of the Na+-pumping NADH:Quinone Oxidoreductase from Vibrio cholerae.

Journal: The Journal of biological chemistry 20090327

Title: Validation and application of an HPLC-EC method for analysis of coenzyme Q10 in blood platelets.

Journal: Biomedical chromatography : BMC 20081201

Title: Mechanism on two-electron oxidation of ubiquinol at the Qp site in cytochrome bc1 complex: B3LYP study with broken symmetry.

Journal: The journal of physical chemistry. B 20081127

Title: The fully oxidized form of the cytochrome bd quinol oxidase from E. coli does not participate in the catalytic cycle: direct evidence from rapid kinetics studies.

Journal: FEBS letters 20081029

Title: Characterization of mutations in crucial residues around the Q(o) binding site of the cytochrome bc complex from Paracoccus denitrificans.

Journal: The FEBS journal 20081001

Title: High-sensitivity simultaneous analysis of ubiquinol-10 and ubiquinone-10 in human plasma.

Journal: Journal of chromatographic science 20080901

Title: A mitochondria-targeted nitroxide is reduced to its hydroxylamine by ubiquinol in mitochondria.

Journal: Free radical biology & medicine 20080401

Title: Formation of engineered intersubunit disulfide bond in cytochrome bc1 complex disrupts electron transfer activity in the complex.

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Title: Mutations in cytochrome b that affect kinetics of the electron transfer reactions at center N in the yeast cytochrome bc1 complex.

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Journal: The Biochemical journal 20080101

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Journal: The Journal of biological chemistry 20071019

Title: Specific and rapid analysis of ubiquinones using Craven's reaction and HPLC with postcolumn derivatization.

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Title: Effect of carni Q-gel (ubiquinol and carnitine) on cytokines in patients with heart failure in the Tishcon study.

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Title: Ab initio calculation of proton-coupled electron transfer rates using the external-potential representation: a ubiquinol complex in solution.

Journal: The Journal of chemical physics 20070614

Title: Solution structure of the Rhodobacter sphaeroides PufX membrane protein: implications for the quinone exchange and protein-protein interactions.

Journal: Biochemistry 20070327

Title: Mutational analysis of cytochrome b at the ubiquinol oxidation site of yeast complex III.

Journal: The Journal of biological chemistry 20070209

Title: Glutamates 99 and 107 in transmembrane helix III of subunit I of cytochrome bd are critical for binding of the heme b595-d binuclear center and enzyme activity.

Journal: Biochemistry 20061226

Title: Investigation of the mechanism of proton translocation by NADH:ubiquinone oxidoreductase (complex I) from bovine heart mitochondria: does the enzyme operate by a Q-cycle mechanism?

Journal: The Biochemical journal 20061215

Title: Adaptations to oxidative stress induced by vitamin E deficiency in rat liver.

Journal: Journal of bioenergetics and biomembranes 20061201

Title: Regulatory interactions between ubiquinol oxidation and ubiquinone reduction sites in the dimeric cytochrome bc1 complex.

Journal: The Journal of biological chemistry 20061013

Title: Localization of superoxide anion production to mitochondrial electron transport chain in 3-NPA-treated cells.

Journal: Mitochondrion 20061001

Title: Knock-downs of iron-sulfur cluster assembly proteins IscS and IscU down-regulate the active mitochondrion of procyclic Trypanosoma brucei.

Journal: The Journal of biological chemistry 20060929

Title: Probing the role of E272 in quinol oxidation of mitochondrial complex III.

Journal: Biochemistry 20060801

Title: Existence of aa3-type ubiquinol oxidase as a terminal oxidase in sulfite oxidation of Acidithiobacillus thiooxidans.

Journal: Bioscience, biotechnology, and biochemistry 20060701

Title: Probing the ubiquinol-binding site in cytochrome bd by site-directed mutagenesis.

Journal: Biochemistry 20060627

Title: Mass spectrometric analysis of the ubiquinol-binding site in cytochrome bd from Escherichia coli.

Journal: The Journal of biological chemistry 20060127

Title: Different effects of chilling on respiration in leaves and roots of cucumber (Cucumis sativus).

Journal: Plant physiology and biochemistry : PPB 20060101

Title: Ubiquinol: a potential biomarker for tissue energy requirements and oxidative stress.

Journal: Clinica chimica acta; international journal of clinical chemistry 20051001

Title: Lipid peroxidation induced by carbon tetrachloride and its inhibition by antioxidant as evaluated by an oxidative stress marker, HODE.

Journal: Toxicology and applied pharmacology 20051001

Title: Ubiquinol oxidation in the cytochrome bc1 complex: reaction mechanism and prevention of short-circuiting.

Journal: Biochimica et biophysica acta 20050815

Title: Proteins in human brain cortex are modified by oxidation, glycoxidation, and lipoxidation. Effects of Alzheimer disease and identification of lipoxidation targets.

Journal: The Journal of biological chemistry 20050603

Title: Cytochrome b mutations that modify the ubiquinol-binding pocket of the cytochrome bc1 complex and confer anti-malarial drug resistance in Saccharomyces cerevisiae.

Journal: The Journal of biological chemistry 20050429

Title: Structural and biochemical characterization of a quinol binding site of Escherichia coli nitrate reductase A.

Journal: The Journal of biological chemistry 20050415

Title: Reaction intermediates of quinol oxidation in a photoactivatable system that mimics electron transfer in the cytochrome bc1 complex.

Journal: Journal of the American Chemical Society 20050330

Title: Sensitivities of the alternative respiratory components of potato tuber mitochondria to thiol reagents and Ca2+.

Journal: Plant physiology and biochemistry : PPB 20050101

Title: Ubiquinol and the papaverine derivative caroverine prevent the expression of tumour- promoting factors in adenoma and carcinoma colon cancer cells induced by dietary fat.

Journal: BioFactors (Oxford, England) 20050101

Title: Dynamics of lipid oxidation and antioxidant depletion in Mediterranean fish stored at different temperatures.

Journal: BioFactors (Oxford, England) 20050101

Title: Arginine 391 in subunit I of the cytochrome bd quinol oxidase from Escherichia coli stabilizes the reduced form of the hemes and is essential for quinol oxidase activity.

Journal: The Journal of biological chemistry 20041224

Title: Cytochrome bc(1) regulates the mitochondrial permeability transition by two distinct pathways.

Journal: The Journal of biological chemistry 20041126

Title: Active oxygen chemistry within the liposomal bilayer. Part III: Locating Vitamin E, ubiquinol and ubiquinone and their derivatives in the lipid bilayer.

Journal: Chemistry and physics of lipids 20040801

Title: Coenzyme Q10 changes are associated with metabolic syndrome.

Journal: Clinica chimica acta; international journal of clinical chemistry 20040601

Title: Anti-cooperative oxidation of ubiquinol by the yeast cytochrome bc1 complex.

Journal: The Journal of biological chemistry 20040409

Title: NapGH components of the periplasmic nitrate reductase of Escherichia coli K-12: location, topology and physiological roles in quinol oxidation and redox balancing.

Journal: The Biochemical journal 20040401

Title: Disruption of the interaction between the Rieske iron-sulfur protein and cytochrome b in the yeast bc1 complex owing to a human disease-associated mutation within cytochrome b.

Journal: European journal of biochemistry 20040401

Title: Plasma and CSF markers of oxidative stress are increased in Parkinson's disease and influenced by antiparkinsonian medication.

Journal: Neurobiology of disease 20040201

Title: [Protective effect of hydrophilic ubiquinone on cardiac muscle during oxidative stress].

Journal: Kardiologiia 20040101

Title: Elimination of the disulfide bridge in the Rieske iron-sulfur protein allows assembly of the [2Fe-2S] cluster into the Rieske protein but damages the ubiquinol oxidation site in the cytochrome bc1 complex.

Journal: Biochemistry 20031125

Title: Structure of the yeast cytochrome bc1 complex with a hydroxyquinone anion Qo site inhibitor bound.

Journal: The Journal of biological chemistry 20030815

Title: Molecular basis for atovaquone binding to the cytochrome bc1 complex.

Journal: The Journal of biological chemistry 20030815

Title: Protonmotive pathways and mechanisms in the cytochrome bc1 complex.

Journal: FEBS letters 20030612

Title: Architecture of the Qo site of the cytochrome bc1 complex probed by superoxide production.

Journal: Biochemistry 20030603

Title: Inhibition of neutral Mg2+-dependent sphingomyelinase by ubiquinol-mediated plasma membrane electron transport.

Journal: Protoplasma 20030501

Title: Stability studies of ubiquinol in plasma.

Journal: Annals of clinical biochemistry 20030101

Title: Structure and function of quinone binding membrane proteins.

Journal: Advances in protein chemistry 20030101

Title: Regeneration of the antioxidant ubiquinol by lipoamide dehydrogenase, thioredoxin reductase and glutathione reductase.

Journal: BioFactors (Oxford, England) 20030101

Title: Statins lower plasma and lymphocyte ubiquinol/ubiquinone without affecting other antioxidants and PUFA.

Journal: BioFactors (Oxford, England) 20030101

Title: Coenzyme Q10-containing composition (Immugen) protects against occupational and environmental stress in workers of the gas and oil industry.

Journal: BioFactors (Oxford, England) 20030101

Title: The protective and healing effects of a natural antioxidant formulation based on ubiquinol and Aloe vera against dextran sulfate-induced ulcerative colitis in rats.

Journal: BioFactors (Oxford, England) 20030101

Title: Nonoxidizable ubiquinol derivatives that are suitable for the study of the ubiquinol oxidation site in the cytochrome bc1 complex.

Journal: Biochimica et biophysica acta 20021202

Title: Ubiquinol inhibition of neutral sphingomyelinase in liver plasma membrane: specific inhibition of the Mg(2+)-dependent enzyme and role of isoprenoid chain.

Journal: Biochemical and biophysical research communications 20020927

Title: Interactions of quinone with the iron-sulfur protein of the bc(1) complex: is the mechanism spring-loaded?

Journal: Biochimica et biophysica acta 20020910

Title: Lipoyl dehydrogenase catalyzes reduction of nitrated DNA and protein adducts using dihydrolipoic acid or ubiquinol as the cofactor.

Journal: Chemico-biological interactions 20020815

Title: Multiple Q-cycle bypass reactions at the Qo site of the cytochrome bc1 complex.

Journal: Biochemistry 20020625

Title: Roles of NapF, NapG and NapH, subunits of the Escherichia coli periplasmic nitrate reductase, in ubiquinol oxidation.

Journal: Molecular microbiology 20020401

Title: [Mitochondrial complex II (succinate-ubiquinone oxidoreductase)].

Journal: Nihon rinsho. Japanese journal of clinical medicine 20020401

Title: [Inhibitors of complex I and II of the mitochondrial respiratory chain].

Journal: Nihon rinsho. Japanese journal of clinical medicine 20020401

Title: Mitochondrial superoxide radical formation is controlled by electron bifurcation to the high and low potential pathways.

Journal: Free radical research 20020401

Title: Ubiquinol and a coenzyme Q reducing system protect platelet mitochondrial function of transfusional buffy coats from oxidative stress.

Journal: Free radical research 20020401

Title: Inhibitory analogs of ubiquinol act anti-cooperatively on the Yeast cytochrome bc1 complex. Evidence for an alternating, half-of-the-sites mechanism of ubiquinol oxidation.

Journal: The Journal of biological chemistry 20020111

Title: Role of protonatable groups of bovine heart bc(1) complex in ubiquinol binding and oxidation.

Journal: European journal of biochemistry 20011101

Title: Effect of atorvastatin on LDL oxidation and antioxidants in normocholesterolemic type 2 diabetic patients.

Journal: Clinica chimica acta; international journal of clinical chemistry 20010925

Title: Reactivity of ubiquinones and ubiquinols with free radicals.

Journal: Free radical research 20010701

Title: Neutral magnesium-dependent sphingomyelinase from liver plasma membrane: purification and inhibition by ubiquinol.

Journal: Journal of bioenergetics and biomembranes 20010401

Title: Reduction of ubiquinone by lipoamide dehydrogenase. An antioxidant regenerating pathway.

Journal: European journal of biochemistry 20010301

Title: Direct evidence for the protonation of aspartate-75, proposed to be at a quinol binding site, upon reduction of cytochrome bo3 from Escherichia coli.

Journal: Biochemistry 20010130

Title: Activity of alpha-lipoic acid in the protection against oxidative stress in skin.

Journal: Current problems in dermatology 20010101

Title: Purification and some properties of ubiquinol oxidase from obligately chemolithotrophic iron-oxidizing bacterium, Thiobacillus ferrooxidans NASF-1.

Journal: Bioscience, biotechnology, and biochemistry 20010101

Title: Biochemical, physiological and medical aspects of ubiquinone function.

Journal: Biochimica et biophysica acta 19950524

Title: Ubiquinol: an endogenous antioxidant in aerobic organisms.

Journal: The Clinical investigator 19930101

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Tags:3066-90-8 Molecular Formula|3066-90-8 MDL|3066-90-8 SMILES|3066-90-8 2,3-Dimethoxy-5-methylhydroquinone