Reduced CoQ10, unoxidized CoQ10, CoQ10H2, or dihydroquinone
|Jmol 3D model||Interactive image|
|Molar mass||865.38 g·mol−1|
|Melting point||45.6 °C (114.1 °F; 318.8 K)|
|practically insoluble in water|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
Ubiquinol is an electron-rich (reduced) form of coenzyme Q10.
The natural ubiquinol form of coenzyme Q10 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.
Because humans can synthesize ubiquinol, it is not classed as a vitamin.
It is well-established that CoQ10 is not well absorbed into the body, as has been published in many peer-reviewed scientific journals. Since the ubiquinol form has two additional hydrogens, it results in the conversion of two ketone groups into hydroxyl groups on the active portion of the molecule. This causes an increase in the polarity of the CoQ10 molecule and may be a significant factor behind the observed enhanced bioavailability of ubiquinol. Taken orally, ubiquinol exhibits greater bioavailability than ubiquinone.
However, there are authorities that dispute whether ubiquinol is more bioavailable in practice rather than in theory compared to CoQ10 supplements because those have their CoQ10 molecules dissolved in lipid micelles, which then deliver their cargo to the plasma membrane in the intestinal wall. There they dissolve via simple diffusion in the intestinal cells, then onto the lymphatic vessels, and then into the venous system. Since ubiquinol and CoQ10 are redox pairs and can and are rapidly inter-converted in the body, it is not clear that ubiqinol's more hydrophilic nature compared to CoQ10 is of practical significance.
Content in foods
In foods, there are varying amounts of ubiquinol. An analysis of a range of foods found ubiquinol to be present in 66 out of 70 items and accounted for 46% of the total coenzyme Q10 intake (in the Japanese diet). The following chart is a sample of the results.
|Food||Ubiquinol (μg/g)||Ubiquinone (μg/g)|
The reduction of ubiquinone to ubiquinol occurs in Complexes I & II in the electron transfer chain. The Q cycle is a process that occurs in cytochrome b, a component of Complex III in the electron transport chain, and that converts ubiquinol to ubiquinone in a cyclic fashion. When ubiquinol binds to cytochrome b, the pKa of the phenolic group decreases so that the proton ionizes and the phenoxide anion is formed.
If the phenoxide oxygen is oxidized, the semiquinone is formed with the unpaired electron being located on the ring.
A page on Proteopedia, Complex III of Electron Transport Chain, contains rotatable 3-D structures of Complex III, which may be used to study the peptide structures of Complex III and the mechanism of the Q cycle.
- MitoQ - mitochondria-targeted version of CoQ10 with increased bioavailability and efficacy over other formulations
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- http://proteopedia.org/wiki/index.php/Complex_III_of_Electron_Transport_Chain[full citation needed][unreliable medical source?]