Ubidecarenone

C59H90O4

863.37
2,5-Cyclohexadiene-1,4-dione, 2-[(2E,6E,10E,14E,18E,22E,26E,30E,34E)-3,7,11,15,19,23,27,31,35,39-decamethyl-2,6,10,14,18,22,26,30,34,38-tetracontadecaenyl]-5,6-dimethoxy-3-methyl.
2-[(all-E)-3,7,11,15,19,23,27,31,35,39-Decamethyl-2,6,10,14,18,22,26,30,34,38-tetracontadecaenyl)-5,6-dimethoxy-3-methyl-p-benzoquinone

[303-98-0].

» Ubidecarenone (Coenzyme Q10) contains not less than 98.0 percent and not more than 101.0 percent of C59H90O4, calculated on the anhydrous basis.

Packaging and storage— Preserve in well-closed, light-resistant containers.

USP Reference standards

—
USP Ubidecarenone RS.
USP Ubidecarenone Related Compound A RS

.
USP Ubidecarenone for System Suitability RS.

Identification—

A: Infrared Absorption

197K

B: Dissolve about 50 mg of Ubidecarenone in 1 mL of ethyl ether, and add 10 mL of dehydrated alcohol. To 2 mL of this solution, add 3 mL of dehydrated alcohol and 2 mL of dimethyl malonate, add 1 mL of potassium hydroxide solution (1 in 5) dropwise, and mix: a blue color appears.

not more than 0.2%.

not more than 0.1%.

Heavy metals, Method II

231

0.002%.

Chromatographic purity—

test 1: coenzymes Q7, Q8, Q9, Q11 and related impurities—

Mobile phase— Proceed as directed in the Assay.

Chromatographic system— Proceed as directed in the Assay. To evaluate the system suitability requirements, use the System suitability preparation, as prepared in the Assay.

Standard solution and Test solution— Use the Standard preparation and the Assay preparation, as prepared in the Assay.

Procedure— Proceed as directed in the Assay, measure all the peak areas, and calculate the percentage of impurities in the portion of Ubidecarenone taken by the formula:

100(ri / rs)

in which ri is the sum of all peak responses, other than that for ubidecarenone, obtained from the Test solution; and rs is the sum of all peak responses. Not more than 1.0% is found.

test 2: ubidecarenone (2Z)-isomer and related impurities—

Mobile phase— Prepare a filtered and degassed mixture of n-hexane and ethyl acetate (97:3).

System suitability solution— Prepare a solution of USP Ubidecarenone for System Suitability RS in n-hexane having a concentration of about 1 mg per mL.

Test solution— Prepare a solution of Ubidecarenone in n-hexane having a concentration of about 1 mg per mL.

Chromatographic system— The liquid chromatograph is equipped with a 275-nm detector and a 4.6-mm × 25-cm column that contains packing L3. The flow rate is about 2.0 mL per minute. Chromatograph the System suitability solution, and record the peak responses as directed for Procedure: the relative retention times are about 0.85 for ubidecarenone (2Z)-isomer and 1.0 for ubidecarenone; and the resolution, R, between ubidecarenone (2Z)-isomer and ubidecarenone is not less than 1.5.

Procedure— Inject a volume of the Test solution (about 20 µL) into the chromatograph, record the chromatogram, and measure all the peak responses. Calculate the percentage of impurities in the portion of Ubidecarenone taken by the formula:

100(ri / rs)

in which ri is the sum of all peak responses, other than that for ubidecarenone; and rs is the sum of all peak responses. Not more than 1.0% is found.

Calculate the percentage of total impurities as the sum of the percentages obtained by Test 1 and Test 2: not more than 1.5% of total impurities is found.

Assay—

Mobile phase— Prepare a filtered and degassed mixture of methanol and dehydrated alcohol (13:7). Make adjustments if necessary (see System Suitability under Chromatography

621

System suitability preparation— Dissolve accurately weighed quantities of USP Ubidecarenone RS and USP Ubidecarenone Related Compound A RS in dehydrated alcohol, heating at about 50

for 2 minutes if necessary, to obtain a solution having known concentrations of about 0.5 mg of each per mL.

Standard preparation— Dissolve an accurately weighed quantity of USP Ubidecarenone RS in dehydrated alcohol, heating at about 50

for 2 minutes if necessary, to obtain a solution having a known concentration of about 1.0 mg per mL.

Assay preparation— Transfer about 50 mg of Ubidecarenone, accurately weighed, to a 50-mL volumetric flask, dissolve in dehydrated alcohol, heating at about 50

for 2 minutes if necessary, cool, dilute with dehydrated alcohol to volume, and mix.

Chromatographic system (see Chromatography

621

)— The liquid chromatograph is equipped with a 275-nm detector and a 5-mm × 15-cm column that contains packing L1, and is maintained at a temperature of 35

. The flow rate is adjusted to obtain a retention time of about 11 minutes. Chromatograph the System suitability preparation, and record the peak responses as directed for Procedure: the relative retention times are about 0.75 for ubidecarenone related compound A and 1.0 for ubidecarenone; the resolution, R, between ubidecarenone related compound A and ubidecarenone is not less than 4; and the relative standard deviation for replicate injections is not more than 0.8%.

Procedure— Separately inject equal volumes (about 5 µL) of the Standard preparation and the Assay preparation into the chromatograph, record the chromatograms, and measure the responses for the major peaks. Calculate the quantity, in mg, of C59H90O4 in the portion of Ubidecarenone taken by the formula:

50C(rU / rS)

in which C is the concentration, in mg per mL, of USP Ubidecarenone RS in the Standard preparation; and rU and rS are the peak responses obtained from the Assay preparation and the Standard preparation, respectively.

Auxiliary Information— Please check for your question in the FAQs before contacting USP.

Topic/Question	Contact	Expert Committee
Monograph	Curtis Phinney 1-301-816-8540	(DSN05) Dietary Supplements - Non-Botanicals
Reference Standards	Lili Wang, Technical Services Scientist 1-301-816-8129 RSTech@usp.org

USP32–NF27 Page 1079

Pharmacopeial Forum: Volume No. 31(1) Page 86

Chromatographic Column—

UBIDECARENONE

Chromatographic columns text is not derived from, and not part of, USP 32 or NF 27.