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Ubiquinol information


Ubiquinol
Names
IUPAC name
2-[(2E,6E,10E,14E,18E,22E,26E,30E,34E)-3,7,11,15,19,23,27,31,35,39-decamethyltetraconta-2,6,10,14,18,22,26,30,34,38-decaenyl]-5,6-dimethoxy-3-methyl-benzene-1,4-diol
Other names
Reduced CoQ10, unoxidized CoQ10, CoQ10H2, or dihydroquinone
Identifiers
CAS Number
  • 992-78-9 checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 17216048 ☒N
MeSH C003741
PubChem CID
  • 9962735
UNII
  • M9NL0C577Y checkY
CompTox Dashboard (EPA)
  • DTXSID90912840 Edit this at Wikidata
InChI
  • InChI=1S/C49H78O4/c1-36(2)20-13-21-37(3)22-14-23-38(4)24-15-25-39(5)26-16-27-40(6)28-17-29-41(7)30-18-31-42(8)32-19-33-43(9)34-35-45-44(10)46(50)48(52-11)49(53-12)47(45)51/h20,22,24,26,28,30,32,34,46-47,50-51H,13-19,21,23,25,27,29,31,33,35H2,1-12H3/b37-22+,38-24+,39-26+,40-28+,41-30+,42-32+,43-34+ ☒N
    Key: FLVUMORHBJZINO-SGHXUWJISA-N ☒N
SMILES
  • CC1=C(C(C(=C(C1O)OC)OC)O)C/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CCC=C(C)C
Properties
Chemical formula
C59H92O4
Molar mass 865.381 g·mol−1
Appearance off-white powder
Melting point 45.6 °C (114.1 °F; 318.8 K)
Solubility in water
practically insoluble in water
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

A ubiquinol is an electron-rich (reduced) form of coenzyme Q (ubiquinone). The term most often refers to ubiquinol-10, with a 10-unit tail most commonly found in humans.

The natural ubiquinol form of coenzyme Q is 2,3-dimethoxy-5-methyl-6-poly prenyl-1,4-benzoquinol, where the polyprenylated side-chain is 9-10 units long in mammals. Coenzyme Q10 (CoQ10) exists in three redox states, fully oxidized (ubiquinone), partially reduced (semiquinone or ubisemiquinone), and fully reduced (ubiquinol). The redox functions of ubiquinol in cellular energy production and antioxidant protection are based on the ability to exchange two electrons in a redox cycle between ubiquinol (reduced) and the ubiquinone (oxidized) form.[1][2]

  1. ^ Mellors, A; Tappel, AL (1966). "The inhibition of mitochondrial peroxidation by ubiquinone and ubiquinol". The Journal of Biological Chemistry. 241 (19): 4353–6. doi:10.1016/S0021-9258(18)99728-0. PMID 5922959.
  2. ^ Mellors, A.; Tappel, A. L. (1966). "Quinones and quinols as inhibitors of lipid peroxidation". Lipids. 1 (4): 282–4. doi:10.1007/BF02531617. PMID 17805631. S2CID 2129339.

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Ubiquinol

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A ubiquinol is an electron-rich (reduced) form of coenzyme Q (ubiquinone). The term most often refers to ubiquinol-10, with a 10-unit tail most commonly...

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Q cycle

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reduction of the lipophilic electron carrier Coenzyme Q (CoQ) between the ubiquinol and ubiquinone forms, can result in the net movement of protons across...

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Ubiquinol oxidase

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Ubiquinol oxidases (EC 1.10.3.11) are enzymes in the bacterial electron transport chain that oxidise ubiquinol into ubiquinone and reduce oxygen to water...

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Coenzyme Q10

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branched-chain amino acids oxidation (through flavin-linked dehydrogenases) to ubiquinol–cytochrome-c reductase (complex III) of the ETC: CoQ10 participates in...

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Oxidative phosphorylation

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When Q accepts two electrons and two protons, it becomes reduced to the ubiquinol form (QH2); when QH2 releases two electrons and two protons, it becomes...

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Respiratory complex I

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motive force (and accordingly, a ubiquinol-concentrated pool), the enzyme runs in the reverse direction. Ubiquinol is oxidized to ubiquinone, and the...

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Rieske protein

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with widely ranging electron reduction potentials from -150 to +400 mV. Ubiquinol-cytochrome-c reductase (also known as bc1 complex or complex III) is an...

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UQCC2

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Ubiquinol-cytochrome c reductase complex assembly factor 2 is a protein that in humans is encoded by the UQCC2 gene. Located in the mitochondrial nucleoid...

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Succinate dehydrogenase

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oxidation of succinate to fumarate with the reduction of ubiquinone to ubiquinol. This occurs in the inner mitochondrial membrane by coupling the two reactions...

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Electron transport chain

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transferred to a lipid-soluble carrier, ubiquinone (Q). The reduced product, ubiquinol (QH2), freely diffuses within the membrane, and Complex I translocates...

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Cytochrome d

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catalyse the two electron oxidation of ubiquinol. This process is an oxidative phosphorylation that oxidizes the ubiquinol-8 to ubiquinone. The chemical reaction...

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Mitochondrion

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is released at complex III when Fe3+ of cytochrome c reacts to oxidize ubiquinol (QH2): 2 Fe 3 + ( cyt c ) + QH 2 ⟶ 2 Fe 2 + ( cyt c ) + Q + 2 H + ( aq...

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Citric acid cycle

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eventually to ubiquinone (Q) in the mitochondrial membrane, reducing it to ubiquinol (QH2) which is a substrate of the electron transfer chain at the level...

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Cytochrome C1

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Symbol CYC1 Alt. symbols UQCR4, MC3DN6 Alt. names Complex III subunit 4, Ubiquinol-cytochrome-c reductase complex cytochrome c1 subunit NCBI gene 1537 HGNC...

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Hypochlorous acid

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stopping the flow of electrons to oxygen. Later studies revealed that Ubiquinol oxidase activity ceases first, and the still-active cytochromes reduce...

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Semiquinone

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reducing the supplementary form of CoQ10 (ubiquinone) to its active form ubiquinol. Song, Y; Buettner, GR (Sep 15, 2010). "Thermodynamic and kinetic considerations...

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Antimycin A

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of cytochrome c reductase, inhibiting the reduction of ubiquinone to ubiquinol in the Qi site, thereby disrupting the Q-cycle of enzyme turn over. It...

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Cellular respiration

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72 ATP (instead of 2.5) and the 6 protons from oxidizing succinate or ubiquinol would produce 1.64 ATP (instead of 1.5). This is consistent with experimental...

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Antioxidant

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through reduction by other antioxidants, such as ascorbate, retinol or ubiquinol. This is in line with findings showing that α-tocopherol, but not water-soluble...

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Electron bifurcation

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results in oxidative phosphorylation. In that case one electron from ubiquinol is directed to a Rieske cluster and the other electron is directed to...

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Cytochrome b

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respiratory chain complex III (EC 1.10.2.2) — also known as the bc1 complex or ubiquinol-cytochrome c reductase. In plant chloroplasts and cyanobacteria, there...

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Electrochemical gradient

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transport chain, complex I (CI) catalyzes the reduction of ubiquinone (UQ) to ubiquinol (UQH2) by the transfer of two electrons from reduced nicotinamide adenine...

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UQCRC2

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The product of UQCRC2 is a subunit of the respiratory chain protein Ubiquinol Cytochrome c Reductase (UQCR, Complex III or Cytochrome bc1 complex),...

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BCS1L

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Mitochondrial chaperone BCS1 (BCS1L), also known as BCS1 homolog, ubiquinol-cytochrome c reductase complex chaperone (h-BCS1), is a protein that in humans...

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Vitamin E

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through reduction by other antioxidants, such as ascorbate, retinol or ubiquinol. Other forms of vitamin E have their own unique properties; for example...

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