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[ CAS No. 303-97-9 ] {[proInfo.proName]}

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Chemical Structure| 303-97-9
Chemical Structure| 303-97-9
Structure of 303-97-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 303-97-9 ]

CAS No. :303-97-9 MDL No. :MFCD00056635
Formula : C54H82O4 Boiling Point : -
Linear Structure Formula :- InChI Key :UUGXJSBPSRROMU-WJNLUYJISA-N
M.W : 795.23 Pubchem ID :5280473
Synonyms :
Ubiquinone Q9;CoQ9;NSC 226993;Ubiquinone 9

Safety of [ 303-97-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 303-97-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 303-97-9 ]

[ 303-97-9 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 13190-97-1 ]
  • [ 3066-90-8 ]
  • [ 303-97-9 ]
YieldReaction ConditionsOperation in experiment
63.0% Example 7 Preparation of CoQ9 In a 100 ml flask equipped with a thermometer, a reflux condenser and a stir bar 1.17 g (6.35 mmol) of 2,3-dimethoxy-6-methyl-l,4-hydroquinone (DMMHQ) were dissolved in 6 ml of nitromethane and mixed with 0.83 g (1.27 mmol) of <strong>[13190-97-1]solanesol</strong> dissolved in 12 ml of heptane. After addition of 369 mul of aqueous 1.3 w% H3O40PWi2 solution in nitromethane to the liquid-liquid two-phase system, the mixture was heated to 40C (internal temperature) for 3 hours. After cooling to room temperature, the layers were separated. The heptane phase was washed with 3 ml Of CH3NO2. The heptane-phase was stirred 1 hour at room temperature with 0.7 g OfAg2O (3 mmol) and 0.05 ml of CH3COOH (0.9 mmol) to oxidize the alkylation product to CoQ9. The suspension was filtered over Speedex, the orange solution was concentrated in vacuo (400C, 100 -> 10 mbar). The crude product (0.97 g) was analyzed by HPLC to contain: 2.1 % 2,3-dimethoxy-6-methyl- 1,4-quinone about 18.7 % dienes/dimers; 0.9 % <strong>[13190-97-1]solanesol</strong>; 0.2 % ubihydroquinone; 65.6 % CoQ9. The conversion of <strong>[13190-97-1]solanesol</strong> is 99 % and the yield of CoQ9 63.0 %.
  • 2
  • [ 13190-97-1 ]
  • [ 303-97-9 ]
  • 3
  • [ 303-97-9 ]
  • [ 303-98-0 ]
  • [ 2394-68-5 ]
  • [ 303-95-7 ]
  • [ 74075-00-6 ]
  • ubiquinol [ No CAS ]
  • [ 5677-54-3 ]
YieldReaction ConditionsOperation in experiment
With sodium dithionite In n-heptane; water at 25℃; for 2h; Nitrogen atmosphere; 10 (Example 10) The reduction reaction and crystallization were carried out under exactly the same conditions as in Example 1 except that the oxidized coenzyme Q10 used has a purity of 98.4% (containing 1.0% of oxidized coenzyme Q9, 0.30% of oxidized coenzyme Q8 and 0.04% of oxidized coenzyme Q7). As a result, 93 g of dry white crystals (containing 0.72% of reduced coenzyme Q9, percentage of elimination: 28%; and 0.11% of reduced coenzyme Q8, percentage of elimination: 63%; reduced coenzyme Q7: not detected) (isolated product yield: 93 mole percent) were obtained. The reduced coenzyme Q10/oxidized coenzyme Q10 weight ratio of the crystals obtained was 99.6/0.4, and the purity of the reduced coenzyme Q10 was 99.0%.
  • 4
  • [ 303-97-9 ]
  • [ 303-98-0 ]
  • [ 2394-68-5 ]
  • [ 303-95-7 ]
  • ubiquinol [ No CAS ]
  • [ 5677-54-3 ]
YieldReaction ConditionsOperation in experiment
Stage #1: ubiquinone-45; ubidecarenone; ubiquinone 8; Ubichinon-7 With sodium dithionite In n-heptane; water at 25℃; for 2h; Nitrogen atmosphere; Stage #2: In ethanol; water at 2 - 50℃; Nitrogen atmosphere; 8 (Example 8) A 7% (w/w) ethanol solution of reduced coenzyme Q10 at 50C was prepared (containing 1.00% of reduced coenzyme Q9, 0.30% of reduced coenzyme Q8 and 0.04% of reduced coenzyme Q7) in the same manner as in Example 1 except that the purity of oxidized coenzyme Q8 used was 98.4% (containing 1.0% of oxidized coenzyme Q9, 0.30% of oxidized coenzyme Q8 and 0.04% of oxidized coenzyme Q7). This ethanol solution was added with 50 g of water and cooled to 2 C at cooling rate of 3C/hour while stirring (power required for stirring 0.3 kW/m3) to precipitate a crystal. The slurry showed fairly good fluidity and was easily brushed away from a crystallization container. All the above operations were carried out in a nitrogen atmosphere. The obtained slurry was filtered under reduced pressure (filterability was excellent as compared with Example 1), and the wet crystals were washed in sequence with cold ethanol, cold water and cold ethanol (the cold solvents used for washing having a temperature of 2C). Furthermore, the wet crystal was dried under reduced pressure (20-40C, 1-30mmHg) to give 95 g of white dry crystals (containing 0.52% of reduced coenzyme Q9, removal rate was 48%; reduced coenzyme Q8 and reduced coenzyme Q7 were not detected) (yield: 97 mol%). The reduced coenzyme Q10/oxidized coenzyme Q10 weight ratio of the crystals obtained was 99.3/0.7, and the purity of the reduced coenzymeQ10 was 98.7%.
  • 5
  • [ 303-97-9 ]
  • [ 303-98-0 ]
  • ubiquinol [ No CAS ]
  • [ 5677-54-3 ]
YieldReaction ConditionsOperation in experiment
With sodium dithionite In n-heptane; water at 25℃; for 2h; Nitrogen atmosphere; 1 (Example 1) Oxidized coenzyme Q10 (100 g; containing 0.40% of oxidized coenzyme Q9, purity 99.4%) was dissolved in 1000 g of heptane at 25C. While stirring (power required for stirring: 0.3 kW/m3), an aqueous solution prepared by dissolving 100 g of sodiumhyposulfite (purity: at least 75%), as the reducing agent, in 1000 ml of water was gradually added and the reduction reaction was carried out at 25C and at pH 4 to 6. After the lapse of 2 hours, the aqueous phase was removed from the reaction mixture, and the heptane phase was washed 6 times with 1000 g of a deaerated saturated aqueous sodium chloride solution to give a heptane phase containing 100 g of reduced coenzyme Q10 (containing 0.40% of reduced coenzyme Q9). This heptane phase was cooled to 2C while stirring (power required for stirring: 0.3 kW/m3) to give a white slurry. All the above operations were carried out in a nitrogen atmosphere. The slurry obtained was filtered under reduced pressure, and the wet crystals were washed in sequence with cold heptane, cold ethanol, cold water, cold ethanol and cold heptane (the cold solvents used for washing having a temperature of 2C). The wet crystals were further dried under reduced pressure (20-40C, 1-30 mmHg) to give 93 g of white dry crystals (containing 0.29% of reduced coenzyme Q9, percentage of elimination: 28%) (isolated product yield: 93 mole percent). The reduced coenzyme Q10/oxidized coenzyme Q10 weight ratio of the crystals obtained was 99.6/0.4, and the purity of the reduced coenzyme Q10 was 99.2%.
Stage #1: ubiquinone-45; ubidecarenone With sodium dithionite In n-heptane; water at 25℃; for 2h; Nitrogen atmosphere; Stage #2: In isopropyl alcohol at 2 - 50℃; Nitrogen atmosphere; 2 (Example 2) A series of operations from the reduction reaction to washing with water was carried out under the same conditions as in Example 1 to obtain a heptane solution of reduced coenzyme Q10 (containing 100 g of reduced coenzyme Q10 (containing 0.40% of reduced coenzyme Q9)). This heptane solution was subjected to solvent substitution under reduced pressure to prepare a 7% (w/w) 2-propanol solution of reduced coenzyme Q10 at 50C. This solution was cooled to 2C at cooling rate of 10C/hour while stirring in a nitrogen atmosphere to precipitate a crystal. The slurry showed good fluidity and was easily brushed away from a crystallization container. The obtained slurry was filtered under reduced pressure (filterability was good same as in Example 1), and the wet crystals were washed in sequence with cold 2-propanol, cold water and cold 2-propanol (the cold solvents used for washing having a temperature of 2C). Furthermore, the wet crystal was dried under reduced pressure (20-40C, 1-30 mmHg) to obtain 94 g of white dry crystals (containing 0.20% of reduced coenzyme Q9, percentage of elimination: 50%) (isolated product yield: 94 mol%). The reduced coenzyme Q10/oxidized coenzyme Q10 weight ratio of the crystals obtained was 99.3/0.7, and the purity of the reduced coenzymeQ10 was 99.0%.
Stage #1: ubiquinone-45; ubidecarenone With sodium dithionite In n-heptane; water at 25℃; for 2h; Nitrogen atmosphere; Stage #2: In ethanol; water at 2 - 50℃; Nitrogen atmosphere; 4 (Example 4) The reduction reaction was carried out under the same condition as in Example 1, and further solvent substitution was carried out to prepare a 7% (w/w) ethanol solution at 50C (containing 100 g of reduced coenzyme Q10 (containing 0.40% of reduced coenzyme Q9)). This ethanol solution was added with 50 g of water and cooled to 2C at cooling rate of 10C/hour while stirring in a nitrogen atmosphere to precipitate a crystal. The slurry showed good fluidity and was easily brushed away from a crystallization container. All the above operations were carried out in a nitrogen atmosphere. The obtained slurry was filtered under reduced pressure (filterability was excellent as compared with Example 1), and the wet crystals were washed in sequence with cold ethanol, cold water and cold ethanol (the cold solvents used for washing having a temperature of 2C). Furthermore, the wet crystal was dried under reduced pressure (20-40C, 1-30 mmHg) to obtain 97 g of white dry crystals (containing 0.21% of reduced coenzyme Q9, percentage of elimination: 48%) (isolated product yield: 97 mol%). The reduced coenzyme Q10 /oxidized coenzyme Q10 weight ratio of the crystals obtained was 99.2/0.8, and the purity of the reduced coenzymeQ10 was 98.9%.
Stage #1: ubiquinone-45; ubidecarenone With sodium dithionite In n-heptane; water at 25℃; for 2h; Nitrogen atmosphere; Stage #2: In ethanol at 2 - 50℃; Nitrogen atmosphere; 1 (Comparative Example 1) A heptane phase (containing 0.40% of reduced coenzyme Q9, purity 99.4%) containing 100 g of reduced coenzyme Q10 washed with saturated brine was obtained in the same manner as Example 1. This heptane phase was cooled from 50C to 2C at cooling rate of 10C/hour while stirring (power required for stirring 0. 3 kW/m3) to precipitate a crystal. The obtained slurry showed poor fluidity and was difficult to brush away from a crystallization container as compared with Example 1. All the above operations were carried out in a nitrogen atmosphere. The obtained slurry was filtered under reduced pressure, and the wet crystals were washed in sequence with cold heptane, cold ethanol, cold water, cold ethanol and cold heptane (the cold solvents used for washing having a temperature of 2C). Furthermore, the wet crystal was dried under reduced pressure (20-40C, 1-30 mmHg) to obtain 93 g of white dry crystals (containing 0.29% of reduced coenzyme Q9, percentage of elimination: 28%) (isolated product yield: 93 mol%). The reduced coenzyme Q10 /oxidized coenzyme Q10 weight ratio of the crystals obtained was 99.6/0.4, and the purity of the reduced coenzymeQ10 was 99.2%. The slurry was filtered using a 20 cm-diameter Nutsche funnel with a filter spread thereon and depressurized by an aspirator. The time required for filtration was 37 minutes. Moreover, the obtained crystals were observed with an optical microscope together with the crystals obtained in Examples 1 to 6, they were needle crystals obviously smaller than the cases of Examples 1 to 6.
Stage #1: ubiquinone-45; ubidecarenone With sodium dithionite In n-heptane; water at 25℃; for 2h; Nitrogen atmosphere; Stage #2: In ethanol at 2 - 50℃; Nitrogen atmosphere; 1 (Example 1) Oxidized coenzyme Q10 (100 g; containing 0.40% of oxidized coenzyme Q9, purity 99.4%) was dissolved in 1000 g of heptane at 25C. While stirring (power required for stirring: 0.3 kW/m3), an aqueous solution prepared by dissolving 100 g of sodium hyposulfite (purity: at least 75%), as the reducing agent, in 1000 ml of water was gradually added and the reduction reaction was carried out at 25C and at pH 4 to 6. After the lapse of 2 hours, the aqueous phase was removed from the reaction mixture, and the heptane phase was washed 6 times with 1000 g of deaerated saturated brine. All the above operations were carried out in a nitrogen atmosphere. This heptane phase was subjected to solvent substitution under reducedpressure to prepare a 7% (w/w) ethanol solution of reduced coenzyme Q10 at 50C was prepared (containing 100 g of reduced coenzyme Q10 (containing 0.40% of reduced coenzyme Q9)). Moreover, the solution was cooled to 2C at cooling rate of 10C/hour while stirring in a nitrogen atmosphere (power required for stirring 0.3 kW/m3) to precipitate a crystal. The slurry showed good fluidity andwas easilybrushed away from a crystallization container. The obtained slurry was filtered under reduced pressure, and the wet crystals were washed in sequence with cold ethanol, cold water and cold ethanol (the cold solvents used for washing having a temperature of 2C). The wet crystals were further dried under reduced pressure (20-40C, 1-30 mmHg) to give 95 g of white dry crystals (containing 0.19% of reduced coenzyme Q9, percentage of elimination: 53%) (isolated product yield: 95 mole%). The reduced coenzyme Q10/oxidized coenzyme Q10 weight ratio of the crystals obtained was 99.3/0.7, and the purity of the reduced coenzyme Q10 was 99.0%. The slurry was filtered using a 20 cm-diameter Nutsche funnel with a filter spread thereon and depressurized by an aspirator. The time required for filtration was 12 minutes.
Stage #1: ubiquinone-45; ubidecarenone With sodium dithionite In hexane; water at 25℃; for 2h; Nitrogen atmosphere; Stage #2: In acetone at 2 - 50℃; Nitrogen atmosphere; 3 (Example 3) Oxidized coenzyme Q10 (100 g; containing 0.40% of oxidized coenzyme Q9, purity 99.4%) was dissolved in 1000 g of hexane at 25C. While stirring (power required for stirring 0.3 kW/m3), an aqueous solution prepared by dissolving 100 g of sodium hyposulfite (purity: at least 75%) in 1000 ml of water was gradually added as a reducing agent to carry out the reduction reaction at 25C and at pH of 4 to 6. After the lapse of 2 hours, an aqueous phase was removed from a reaction solution, and further a hexane phase was washed for 6 times with 1000 g of deaerated saturated brine. This hexane phase was subjected to solvent substitution under reduced pressure to prepare a 7% (w/w) acetone solution of reduced coenzyme Q10 at 50C (containing 100 g of reduced coenzyme Q10 (containing 0.40% of reduced coenzyme Q9)). This solution was cooled to 2C at cooling rate of 10C/hour while stirring in a nitrogen atmosphere (power required for stirring 0.3 kW/m3) to precipitate a crystal. The slurry showed good fluidity and was easily brushed away from a crystallization container. The obtained slurry was filtered under reduced pressure (filterability was good same as in Example 1). The wet crystals were washed in sequence with cold acetone, cold water and cold acetone (the cold solvents used for washing having a temperature of 2C). Furthermore, the wet crystal was dried under reduced pressure (20-40C, 1-30 mmHg) to obtain 93 g of white dry crystals (containing 0.21% of reduced coenzyme Q9, percentage of elimination: 48%) (isolatedproduct yield: 93 mol%). The reduced coenzyme Q10 /oxidized coenzyme Q10 weight ratio of the crystals obtained was 99.2/0.8, and the purity of the reduced coenzymeQ10 was 98.9%.

YieldReaction ConditionsOperation in experiment
In carbon dioxide at 35℃;
In chloroform; carbon dioxide at 35℃;
In ethanol; carbon dioxide at 35℃;
In carbon dioxide; acetone at 35℃;
In methanol; carbon dioxide at 25 - 75℃; for 0.0833333 - 0.5h;
In methanol; carbon dioxide at 35℃;

  • 7
  • [ 13190-97-1 ]
  • [ 3066-90-8 ]
  • [ 303-97-9 ]
  • [ 5677-54-3 ]
YieldReaction ConditionsOperation in experiment
11.6%; 40.4% With scandium tris(trifluoromethanesulfonate); In nitromethane; hexane; at 50℃; for 16h; Example 4 Preparation of CoQ9 from DMDHT and <strong>[13190-97-1]solanesol</strong> In a 50 ml four necked flask equipped with a stirrer, thermometer, gas inlet, and a reflux condenser, under argon atmosphere 0.654 g (96.52 %, 1 mmol) of <strong>[13190-97-1]solanesol</strong> (nonaprenol, C45) were dissolved in 15 ml of n-hexane. The solution was mixed with 0.983 g (5.0 mmol) of 2,3-dimethoxy-l,4-dihydroxy-toluene (DMDHT) dissolved in 7.6 ml of nitromethane. The catalyst, Sc(OTf)3 (2.5 mg, 0.005 mmol) was then added. The two- phase mixture was heated up to 5O0C (internal temperature) under stirring (400 rpm). After 16 hours reaction time the mixture was cooled down to room temperature (210C). The hexane layer was separated and washed two times with 4 ml (total 8 ml) of nitromethane. The hexane phase was evaporated and yielded 0.78 g of crude 2,3-dimethoxy-5-methyl-6- ((2E,6E,1 OE, 14E.18E,22E,26E,30E)-3,7,l 1,15, 19,23,27,31,35-nonamethyl-hexatriaconta- 2,6,10,14,18,22,26,30,34-nonaenyl)-benzene-l,4-diol (H2-CoQ9), which was purified by column chromatography on 30 g silica (elution with n-hexane/ethyl acetate = 99/1, v/v), to give 440 mg of an orange oil consisting of 73.2% H2-CoQ9 and 21% CoQ9 (formed from H2-CoQ9 by partial air oxidation during isolation and HPLC analysis), corresponding to yields of 40.4% H2-CoQ9 and 11.6% CoQ9, sum 52%.
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