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C7956 Sigma

Coenzyme Q1

≥95%

Synonym: 2,3-Dimethoxy-5-methyl-6-(3-methyl-2-butenyl)-1,4-benzoquinone, Ubiquinone-1, Ubiquinone-5

  • CAS Number 727-81-1

  • Empirical Formula (Hill Notation) C14H18O4

  • Molecular Weight 250.29

  •  MDL number MFCD00274412

  •  PubChem Substance ID 24892585

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Description

Other Notes

Analog of coenzyme Q10 (not naturally occurring)

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. C7956.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Application

Coenzyme Q1 (CoQ1) is a 1 isoprenyl group (not naturally occurring) member of a family of ubiquinones that share a quinine chemical group but differ in the number of isoprenyl chemical subunits in their tail. The CoQ compounds are lipid soluble components of cell membranes where they perform multiple functions such as electron and proton transport. The most well studied CoQ compound is CoQ10. CoQ1 is frequently used in comparison studies on the effect of isoprenyl chain length on CoQ functions or distribution and to identify quinone reductases.

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Safety & Documentation

Safety Information

Documents

Certificate of Analysis

Certificate of Origin

Protocols & Articles

Peer-Reviewed Papers

References

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NQO1-dependent redox cycling of idebenone: effects on cellular redox potential and energy levels. Haefeli RH, Erb M, Gemperli AC, et al. PLoS ONE 6, e17963, (2011)

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Ubiquinone analogs: a mitochondrial permeability transition pore-dependent pathway to selective cell death. Devun F, Walter L, Belliere J, et al. PLoS ONE 5, e11792, (2010)

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Genetic evidence for NAD(P)H:quinone oxidoreductase 1-catalyzed quinone reduction on passage through the mouse pulmonary circulation. Lindemer BJ, Bongard RD, et al. Am. J. Physiol. Lung Cell. Mol. Physiol. 300, L773-780, (2011)

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Decreases in serum ubiquinone concentrations do not result in reduced levels in muscle tissue during short-term simvastatin treatment in humans. Laaksonen R, Jokelainen K, Sahi T, et al. Clin. Pharmacol. Ther. 57(1), 62-6, (1995)

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Platinum nanoparticles have an activity similar to mitochondrial NADH:ubiquinone oxidoreductase. Hikosaka K, Kim J, Kajita M, et al. Colloids Surf. B Biointerfaces 66(2), 195-200, (2008)

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Diagnostic use of cerebral and extracerebral oxysterols. Leoni V, Masterman T, Mousavi FS, et al. Clin. Chem. Lab Med. 42(2), 186-91, (2004)

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Levels of 7-oxocholesterol in cerebrospinal fluid are more than one thousand times lower than reported in multiple sclerosis. Leoni V, Lütjohann D, and Masterman T J. Lipid Res. 46(2), 191-5, (2005)

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Sulfation and glucuronidation of phenols: implications in coenyzme Q metabolism. Shangari N, Chan TS, and O'Brien PJ Meth. Enzymol. 400, 342-59, (2005)

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Discharge of newly-synthesized dolichol and ubiquinone with lipoproteins to rat liver perfusate and to the bile. Elmberger PG, Kalén A, Brunk UT, et al. Lipids 24(11), 919-30, (1989)

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Coenzyme Q cytoprotective mechanisms. Chan TS, Wilson JX, and O'Brien PJ Meth. Enzymol. 382, 89-104, (2004)

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Quantification of chemical elements in blood of patients affected by multiple sclerosis. Forte G, Visconti A, Santucci S, et al. Ann. Ist. Super. Sanita 41(2), 213-6, (2005)

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Oxidative stress in patients with multiple sclerosis. Syburra C and Passi S Ukr. Biokhim. Zh. 71(3), 112-5, (1999)

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Ubiquinone, dolichol, and cholesterol metabolism in aging and Alzheimer's disease. Edlund C, Söderberg M, Kristensson K, et al. Biochem. Cell Biol. 70(6), 422-8, (1992)

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Measurement of immune markers in the serum and cerebrospinal fluid of multiple sclerosis patients during clinical remission. Shaw CE, Dunbar PR, Macaulay HA, et al. J. Neurol. 242(2), 53-8, (1995)

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Prerequisites for ubiquinone analogs to prevent mitochondrial permeability transition-induced cell death. Belliere J, Devun F, Cottet-Rousselle C, et al. J. Bioenerg. Biomembr. 44(1), 207-12, (2012)

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Hepatocyte metabolism of coenzyme Q1 (ubiquinone-5) to its sulfate conjugate decreases its antioxidant activity. Chan TS and O'Brien PJ Biofactors 18(1-4), 207-18, (2003)

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Folate and methylation status in relation to phosphorylated tau protein(181P) and beta-amyloid(1-42) in cerebrospinal fluid. Obeid R, Kasoha M, Knapp JP, et al. Clin. Chem. 53(6), 1129-36, (2007)

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Coenzyme Q(1) depletes NAD(P)H and impairs recycling of ascorbate in astrocytes. Dragan M, Dixon SJ, Jaworski E, et al. Brain Res. 1078(1), 9-18, (2006)

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Serum uric acid levels in multiple sclerosis patients correlate with activity of disease and blood-brain barrier dysfunction. Toncev G, Milicic B, Toncev S, et al. Eur. J. Neurol. 9(3), 221-6, (2002)

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Manipulating respiratory levels in Escherichia coli for aerobic formation of reduced chemical products. Zhu J, Sánchez A, Bennett GN, et al. Metab. Eng. 13(6), 704-12, (2011)

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Genetic evidence for a multi-subunit complex in coenzyme Q biosynthesis in yeast and the role of the Coq1 hexaprenyl diphosphate synthase. Gin P and Clarke CF J. Biol. Chem. 280(4), 2676-81, (2005)

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Inflammatory multiple-sclerosis plaques generate characteristic metabolic profiles in cerebrospinal fluid. Lutz NW, Viola A, Malikova I, et al. PLoS ONE 2(7), e595, (2007)

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Mitochondrial production of reactive oxygen species: role of complex I and quinone analogues. Fato R, Bergamini C, Leoni S, et al. Biofactors 32(1-4), 31-9, (2008)

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Coenzyme Q1 redox metabolism during passage through the rat pulmonary circulation and the effect of hyperoxia. Audi SH, Merker MP, Krenz GS, et al. J. Appl. Physiol. 105(4), 1114-26, (2008)

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Statins lower plasma and lymphocyte ubiquinol/ubiquinone without affecting other antioxidants and PUFA. Passi S, Stancato A, Aleo E, et al. Biofactors 18(1-4), 113-24, (2003)

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Role of mitochondrial electron transport complex I in coenzyme Q1 reduction by intact pulmonary arterial endothelial cells and the effect of hyperoxia. Merker MP, Audi SH, Lindemer BJ, et al. Am. J. Physiol. Lung Cell. Mol. Physiol. 293(3), L809-19, (2007)

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Purification and characterization of Put1p from Saccharomyces cerevisiae. Wanduragala S, Sanyal N, Liang X, et al. Arch. Biochem. Biophys. 498(2), 136-42, (2010)

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Disruption of thiol homeostasis and nitrosative stress in the cerebrospinal fluid of patients with active multiple sclerosis: evidence for a protective role of acetylcarnitine. Calabrese V, Scapagnini G, Ravagna A, et al. Neurochem. Res. 28(9), 1321-8, (2003)

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Reduction of ascorbate free radical by the plasma membrane of synaptic terminals from rat brain. Samhan-Arias AK, Duarte RO, Martín-Romero FJ, et al. Arch. Biochem. Biophys. 469(2), 243-54, (2008)

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Detergent-dependent kinetics of truncated Plasmodium falciparum dihydroorotate dehydrogenase. Malmquist NA, Baldwin J, and Phillips MA J. Biol. Chem. 282(17), 12678-86, (2007)

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Inhibition of glycerophosphate-dependent H2O2 generation in brown fat mitochondria by idebenone. Rauchová H, Vrbacký M, Bergamini C, et al. Biochem. Biophys. Res. Commun. 339(1), 362-6, (2006)

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Inhibitory effect of coenzyme Q on eukaryotic DNA polymerase gamma and DNA topoisomerase II activities on the growth of a human cancer cell line. Yonezawa Y, Kuriyama I, Fukuoh A, et al. Cancer Sci. 97(8), 716-23, (2006)

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Coenzyme Q(1) as a probe for mitochondrial complex I activity in the intact perfused hyperoxia-exposed wild-type and Nqo1-null mouse lung. Bongard RD, Myers CR, Lindemer BJ, et al. Am. J. Physiol. Lung Cell. Mol. Physiol. 302(9), L949-58, (2012)

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Distribution of capillary transit times in isolated lungs of oxygen-tolerant rats. Ramakrishna M, Gan Z, Clough AV, et al. Ann. Biomed. Eng. 38(11), 3449-65, (2010)

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Functional role of coenzyme Q in the energy coupling of NADH-CoQ oxidoreductase (Complex I): stabilization of the semiquinone state with the application of inside-positive membrane potential to proteoliposomes. Ohnishi T, Ohnishi ST, Shinzawa-Ito K, et al. Biofactors 32(1-4), 13-22, (2008)

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C. elegans knockouts in ubiquinone biosynthesis genes result in different phenotypes during larval development. Gavilán A, Asencio C, Cabello J, et al. Biofactors 25(1-4), 21-9, (2005)

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Caenorhabditis elegans ubiquinone biosynthesis genes. Rodríguez-Aguilera JC, Asencio C, Ruiz-Ferrer M, et al. Biofactors 18(1-4), 237-44, (2003)

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Oral administration of coenzyme Q₁₀ reduces MPTP-induced loss of dopaminergic nerve terminals in the striatum in mice. Kobayashi S, Muroyama A, Matsushima H, et al. Neurol. Sci. 33(1), 195-9, (2012)

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Simultaneous determination of ubiquinol and ubiquinone in skeletal muscle of pediatric patients. Pastore A, Giovamberardino GD, Bertini E, et al. Anal. Biochem. 342(2), 352-5, (2005)

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