Decylubiquinone | CAS# 55486-00-5

Decylubiquinone
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 329653

CAS#: 55486-00-5

Description: Decylubiquinone is an analog of ubiquinone. Decylubiquinone increases mitochondrial function in synaptosomes. decylubiquinone inhibits the redox-activated mitochondrial permeability transition. It blocks reactive oxygen species production in response to glutathione depletion and inhibits activation of the mitochondrial permeability transition.

Chemical Structure

Decylubiquinone

CAS# 55486-00-5

Instruction

Theoretical Analysis

MedKoo Cat#: 329653
Name: Decylubiquinone
CAS#: 55486-00-5
Chemical Formula: C19H30O4
Exact Mass: 322.21
Molecular Weight: 322.445
Elemental Analysis: C, 70.77; H, 9.38; O, 19.85

Price and Availability

Size	Price	Availability
10mg	USD 275	2 Weeks
25mg	USD 550	2 Weeks
50mg	USD 950	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: Decylubiquinone

IUPAC/Chemical Name: 2-decyl-5,6-dimethoxy-3-methyl-2,5-cyclohexadiene-1,4-dione

InChi Key: VMEGFMNVSYVVOM-UHFFFAOYSA-N

InChi Code: InChI=1S/C19H30O4/c1-5-6-7-8-9-10-11-12-13-15-14(2)16(20)18(22-3)19(23-4)17(15)21/h5-13H2,1-4H3

SMILES Code: O=C1C(CCCCCCCCCC)=C(C)C(C(OC)=C1OC)=O

Appearance: Yellow, viscous oil in pure form (supplied as 200mg / mL ethanol solution)

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Instruction:

View handling instruction

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 322.45 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Telford JE, Kilbride SM, Davey GP. Decylubiquinone increases mitochondrial function in synaptosomes. J Biol Chem. 2010 Mar 19;285(12):8639-45. doi: 10.1074/jbc.M109.079780. Epub 2010 Jan 14. PubMed PMID: 20080966; PubMed Central PMCID: PMC2838286.

2: Murad LB, Guimarães MR, Vianna LM. Effects of decylubiquinone (coenzyme Q10 analog) supplementation on SHRSP. Biofactors. 2007;30(1):13-8. PubMed PMID: 18198397.

3: Armstrong JS, Whiteman M, Rose P, Jones DP. The Coenzyme Q10 analog decylubiquinone inhibits the redox-activated mitochondrial permeability transition: role of mitcohondrial [correction mitochondrial] complex III. J Biol Chem. 2003 Dec 5;278(49):49079-84. Epub 2003 Aug 29. PubMed PMID: 12949071.

4: Amarneh B, Vik SB. Mutagenesis of subunit N of the Escherichia coli complex I. Identification of the initiation codon and the sensitivity of mutants to decylubiquinone. Biochemistry. 2003 May 6;42(17):4800-8. PubMed PMID: 12718520.

5: Gopta OA, Semenov AY, Bloch DA. Electrogenic proton transfer in Rhodobacter sphaeroides reaction centers: effect of coenzyme Q(10) substitution by decylubiquinone in the Q(B) binding site. FEBS Lett. 2001 Jun 15;499(1-2):116-20. Erratum in: FEBS Lett 2002 Apr 24;517(1-3):288. PubMed PMID: 11418124.

6: Zhang Y, Weiner JH. A simple semi-quantitative in vivo method using H₂S detection to monitor sulfide metabolizing enzymes. Biotechniques. 2014 Oct 1;57(4):208-10. doi: 10.2144/000114218. eCollection 2014 Oct. PubMed PMID: 25312091.

7: Bénit P, Slama A, Rustin P. Decylubiquinol impedes mitochondrial respiratory chain complex I activity. Mol Cell Biochem. 2008 Jul;314(1-2):45-50. doi: 10.1007/s11010-008-9763-z. Epub 2008 Apr 15. PubMed PMID: 18414996.

8: Maliniemi P, Kervinen M, Hassinen IE. Modeling of human pathogenic mutations in Escherichia coli complex I reveals a sensitive region in the fourth inside loop of NuoH. Mitochondrion. 2009 Nov;9(6):394-401. doi: 10.1016/j.mito.2009.07.001. Epub 2009 Jul 17. PubMed PMID: 19616643.

9: Ke H, Morrisey JM, Ganesan SM, Painter HJ, Mather MW, Vaidya AB. Variation among Plasmodium falciparum strains in their reliance on mitochondrial electron transport chain function. Eukaryot Cell. 2011 Aug;10(8):1053-61. doi: 10.1128/EC.05049-11. Epub 2011 Jun 17. PubMed PMID: 21685321; PubMed Central PMCID: PMC3165440.

10: Ohnishi ST, Shinzawa-Itoh K, Ohta K, Yoshikawa S, Ohnishi T. New insights into the superoxide generation sites in bovine heart NADH-ubiquinone oxidoreductase (Complex I): the significance of protein-associated ubiquinone and the dynamic shifting of generation sites between semiflavin and semiquinone radicals. Biochim Biophys Acta. 2010 Dec;1797(12):1901-9. doi: 10.1016/j.bbabio.2010.05.012. Epub 2010 Jun 1. PubMed PMID: 20513438.

11: Racay P, Tatarkova Z, Chomova M, Hatok J, Kaplan P, Dobrota D. Mitochondrial calcium transport and mitochondrial dysfunction after global brain ischemia in rat hippocampus. Neurochem Res. 2009 Aug;34(8):1469-78. doi: 10.1007/s11064-009-9934-7. Epub 2009 Feb 28. PubMed PMID: 19252983.

12: Fato R, Bergamini C, Leoni S, Lenaz G. Mitochondrial production of reactive oxygen species: role of complex I and quinone analogues. Biofactors. 2008;32(1-4):31-9. PubMed PMID: 19096098.

13: Brière JJ, Schlemmer D, Chretien D, Rustin P. Quinone analogues regulate mitochondrial substrate competitive oxidation. Biochem Biophys Res Commun. 2004 Apr 16;316(4):1138-42. PubMed PMID: 15044103.

14: Yano T, Li LS, Weinstein E, Teh JS, Rubin H. Steady-state kinetics and inhibitory action of antitubercular phenothiazines on mycobacterium tuberculosis type-II NADH-menaquinone oxidoreductase (NDH-2). J Biol Chem. 2006 Apr 28;281(17):11456-63. Epub 2006 Feb 9. PubMed PMID: 16469750.

15: Wang Y, Perchellet EM, Ward MM, Lou K, Hua DH, Perchellet JP. Rapid collapse of mitochondrial transmembrane potential in HL-60 cells and isolated mitochondria treated with anti-tumor 1,4-anthracenediones. Anticancer Drugs. 2005 Oct;16(9):953-67. PubMed PMID: 16162972.

16: Fontaine E, Ichas F, Bernardi P. A ubiquinone-binding site regulates the mitochondrial permeability transition pore. J Biol Chem. 1998 Oct 2;273(40):25734-40. PubMed PMID: 9748242.

17: Karpinich NO, Tafani M, Rothman RJ, Russo MA, Farber JL. The course of etoposide-induced apoptosis from damage to DNA and p53 activation to mitochondrial release of cytochrome c. J Biol Chem. 2002 May 10;277(19):16547-52. Epub 2002 Feb 25. PubMed PMID: 11864976.

18: David P, Baumann M, Wikström M, Finel M. Interaction of purified NDH-1 from Escherichia coli with ubiquinone analogues. Biochim Biophys Acta. 2002 Feb 15;1553(3):268-78. PubMed PMID: 11997136.

19: Hano N, Nakashima Y, Shinzawa-Itoh K, Terada H, Yoshikawa S. Effect of pH on the steady state kinetics of bovine heart NADH: coenzyme Q oxidoreductase. J Bioenerg Biomembr. 2003 Oct;35(5):419-25. PubMed PMID: 14740890.

20: Ge X, Fu YM, Li YQ, Meadows GG. Activation of caspases and cleavage of Bid are required for tyrosine and phenylalanine deficiency-induced apoptosis of human A375 melanoma cells. Arch Biochem Biophys. 2002 Jul 1;403(1):50-8. PubMed PMID: 12061801.

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