303-97-9

Basic information

• Product Name: COENZYME Q9
• Synonyms: COENZYME Q9;UBIQUINONE-45;UBIQUINONE-9;,6,10,14,18,22,26,30,34-hexatriacontanonaenyl)-;coenzymeq(sub9);coq(sub9);p-benzoquinone,2,3-dimethoxy-5-methyl-6-(3,7,11,15,19,23,27,31,35-nonamethyl-2;ubiquinoneq(sub9)
• CAS NO: 303-97-9
• Molecular Formula: C₅₄H₈₂O₄
• Molecular Weight: 795.23
• EINECS: 215-668-0
• Product Categories: Mixed Fatty Acids;Fatty Acid Derivatives & Lipids;Glycerols
• Mol File: 303-97-9.mol

Chemical Properties

• Melting Point: 41-43°C
• Boiling Point: 826.8±65.0 °C(Predicted)
• Appearance: /
• Density: 0.97±0.1 g/cm3(Predicted)
• Storage Temp.: −20°C
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly, Heated)
• BRN: 1900081
• CAS DataBase Reference: COENZYME Q9(CAS DataBase Reference)
• NIST Chemistry Reference: COENZYME Q9(303-97-9)
• EPA Substance Registry System: COENZYME Q9(303-97-9)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 2
• RTECS: DK4786000
• F: 8-10
• Hazardous Substances Data: 303-97-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Coenzyme Q9 is used as an active pharmaceutical ingredient for preventing and treating various types of cancer. It exhibits antibacterial and antioxidant properties, which contribute to its effectiveness in combating cancer cells.
Used in Analytical Chemistry:
Coenzyme Q9 serves as an internal standard for the determination of ubiquinol-10 in biological samples through high-performance chromatography (HPLC) and liquid chromatography tandem mass spectrometry. These methods are employed to evaluate oxidative stress.
Used in Research and Development:
Coenzyme Q9 is utilized as an analyte in the chromatographic analysis of different biological samples corresponding to various genetic conditions. This application aids in understanding the role of CoQ9 in different health contexts.
Used in Quality Control:
This product is provided as delivered and specified by the issuing Pharmacopoeia. It is used to ensure the quality and standardization of Coenzyme Q9 in the pharmaceutical industry, with supporting information available from the issuing Pharmacopoeia's website.
Used in Detection Interference Studies:
Coenzyme Q9 has been employed to investigate its interference in the detection of Coenzyme Q10 (CoQ10) by fluorescent spectrophotometer (FS-ECA), which is crucial for accurate analysis and understanding of these related compounds in biological systems.

Biochem/physiol Actions

The coenzyme Q (CoQ) can perform multiple functions such as electron and proton transport. CoQ9 performs similar functions to CoQ10 as the native CoQ in Caenorhabditis elegans. CoQ9 as well as other CoQ molecules may have an impact on cell life-span and these molecules are seeing increase usage in such studies.

Purification Methods

The yellow crystals are purified by recrystallisation from pet ether and by chromatography on SiO2 plates and eluted with Et2O/hexane. The purity can be checked by HPLC (silica column using 7% Et2O/hexane). It has max 270nm ( 14,850) in pet ether. [NMR and MS: Naruta J Org Chem 45 4097 1980, Le et al. Biochem Biophys Acta 32 497 1958, cf Morton Biochemical Spectroscopy (Adam Hilger, London, 1975) p 491, IR: Lester et al. Biochim Biophys Acta 33 169 1959, UV: Rüegg et al. Helv Chim Acta 42 2616 1959, Shunk J Am Chem Soc 81 5000 1959, Beilstein 8 IV 3313.]

InChI:InChI=1/C54H82O4/c1-40(2)22-14-23-41(3)24-15-25-42(4)26-16-27-43(5)28-17-29-44(6)30-18-31-45(7)32-19-33-46(8)34-20-35-47(9)36-21-37-48(10)38-39-50-49(11)51(55)53(57-12)54(58-13)52(50)56/h22,24,26,28,30,32,34,36,38H,14-21,23,25,27,29,31,33,35,37,39H2,1-13H3/b41-24+,42-26+,43-28+,44-30+,45-32+,46-34+,47-36+,48-38+

Upstream product

• 13190-97-1 solanesol 
• 3066-90-8 2,3-dimethoxy-5-methylbenzene-1,4-diol 
• 202843-56-9 2-chloromethyl-5,6-dimethoxy-3-methyl-[1,4]benzoquinone 
• 400010-22-2 (all-E)-2,6,10,14,18,22,26,30,34-nonamethyl-2,6,10,14,18,22,26,30,34-nonacontanonaen-38-yne 
• 5389-87-7 1-chloro-3,7-dimethylocta-2,6-diene 
• 66958-29-0 Acetic acid (4E,8E,12E,16E,20E,24E)-26-(2,5-bis-benzyloxy-3,4-dimethoxy-6-methyl-phenyl)-1-isopropenyl-4,8,12,16,20,24-hexamethyl-hexacosa-4,8,12,16,20,24-hexaenyl ester 
• 66958-28-9 Acetic acid (4E,8E,12E,16E,20E,24E)-26-(2,5-bis-benzyloxy-3,4-dimethoxy-6-methyl-phenyl)-1-(1-hydroxy-1-methyl-ethyl)-4,8,12,16,20,24-hexamethyl-hexacosa-4,8,12,16,20,24-hexaenyl ester 
• 66958-30-3 (6E,10E,14E,18E,22E,26E)-28-(2,5-Bis-benzyloxy-3,4-dimethoxy-6-methyl-phenyl)-2,6,10,14,18,22,26-heptamethyl-octacosa-1,6,10,14,18,22,26-heptaen-3-ol 
• 66958-31-4 1,4-Bis-benzyloxy-2-((2E,6E,10E,14E,18E,22E,26E)-28-chloro-3,7,11,15,19,23,27-heptamethyl-octacosa-2,6,10,14,18,22,26-heptaenyl)-5,6-dimethoxy-3-methyl-benzene 
• 53254-60-7 3,7-dimethyl-1-(p-toluenesulfonyl)-2(E),6-octadiene 
• 66958-27-8 3-[(3E,7E,11E,15E,19E,23E)-25-(2,5-Bis-benzyloxy-3,4-dimethoxy-6-methyl-phenyl)-3,7,11,15,19,23-hexamethyl-pentacosa-3,7,11,15,19,23-hexaenyl]-2,2-dimethyl-oxirane 
• 97804-57-4 rac-1,4,4a,8aα-tetrahydro-6,7-dimethoxy-4aα-methyl-1α,4α-methanonaphthalin-5,8-dion 
• 130627-56-4 rac-6,7-dichloro-1,4,4a,8,8aα-tetrahydro-4aα-methyl-1α,4α-methanonaphthalin-5,8-dion 
• 83626-22-6 2,3-Dimethoxy-6-methyl-4-((2E,6E,10E,14E,18E,22E,26E,30E)-3,7,11,15,19,23,27,31,35-nonamethyl-hexatriaconta-2,6,10,14,18,22,26,30,34-nonaenyloxy)-phenol 

Downstream Products

• 75426-26-5 ubiquinol 
• 5677-54-3 ubiquinone-9 
• 74075-00-6 ubiquinol-8 
• 114832-98-3 1,4-dibenzyloxy-2,3-dimethoxy-5-methyl-6-(3',7',11',15',19',23',27',31',35',39'-decamethyltetraconta-2'E,6'E,10'E,14'E,18'E,22'E,26'E,30'E,34'E/Z,38'-decaenyl)benzene 
• 114832-95-0 1,4-dibenzyloxy-2,3-dimethoxy-5-methyl-6-(34',35'-epoxy-3',7',11',15',19',23',27',31',35'-nonamethylhexatriaconta-2'E,6'E,10'E,14'E,18'E,22'E,26'E,30'E-octaenyl)benzene 
• 303-98-0 34'Z-ubiquinone-10 
• 114832-94-9 1,4-dibenzyloxy-2,3-dimethoxy-5-methyl-6-(34'-bromo-35'-hydroxy-3',7',11',15',19',23',27',31',35'-nonamethylhexatriaconta-2'E,6'E,10'E,14'E,18'E,22'E,26'E,30'E-octaenyl)benzene 
• 114832-96-1 1,4-dibenzyloxy-2,3-dimethoxy-5-methyl-6-(34',35'-dihydroxy-3',7',11',15',19',23',27',31',35'-nonamethylhexatriaconta-2'E,6'E,10'E,14'E,18'E,22'E,26'E,30'E-octaenyl)benzene 
• 114832-97-2 1,4-dibenzyloxy-2,3-dimethoxy-5-methyl-6-(33'-formyl-3',7',11',15',19',23',27',31'-octamethyltritriaconta-2'E,6'E,10'E,14'E,18'E,22'E,26'E,30'E-octaenyl)benzene 
• 303-98-0 ubidecarenone 
• 96358-52-0 2,3-dimethoxy-5-methyl-6-(34',35'-dihydroxy-3',7',11',15',19',23',27',31',35'-nonamethylhexatriaconta-2'E,6'E,10'E,14'E,18'E,22'E,26'E,30'E-octaenyl)benzoquinone-1,4 
• 81914-47-8 2,3-dimethoxy-5-methyl-6-(34,35-epoxy-3,7,11,15,19,23,27,31,35-nonamethylhexatriacont-2E,6E,10E,14E,18E,22E,26E,30E-octaenyl)-1,4-benzoquinone 
• 81914-51-4 2,3-dimethoxy-5-methyl-6-(33-formyl-3,7,11,15,19,23,27,31,35-octamethylhexatriacont-2E,6E,10E,14E,18E,22E,26E,30E-octaenyl)-1,4-benzoquinone 
• 96358-51-9 2,3-dimethoxy-5-methyl-6-(34-acetoxy-35-hydroxy-3,7,11,15,19,23,27,31,35-nonamethylhexatriacont-2E,6E,10E,14E,18E,22E,26E,30E-octaenyl)-1,4-benzoquinone 

Relevant articles and documents

A new synthetic route to ubiquinones

Ubiquinones 11 have been prepared employing a new strategy: as key step, the Diels-Alder reaction of 1,1,2-trichloroethene 3 with 2,5-bis[(trimethylsilyl)oxy]-3- methylfuran (2) has been used for the construction of the quinone part. After methanolysis of the [4 + 2] adducts 4a/4b, further reaction with cyclopentadiene and substitution of the Cl-atoms by MeO groups, the intermediate 7 is obtained. Diketone 7 can easily be alkylated with the desired polyprenyl side chain 9 (X = Br) using a strong base to yield, after a retro-Diels-Alder reaction, the corresponding ubiquinones 11 in high yields.

OFF-NOTE BLOCKING SENSORY ORGANIC COMPOUNDS

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New efficient synthesis of ubiquinones

A strategy for the ecofriendly and high-yielding synthesis of ubiquinones starting from simple materials and using mild conditions is reported. CoQ1, CoQ2, CoQ3, and CoQ9 were prepared. Copyright Taylor & Francis Group, LLC.

PROCESS FOR THE PREPARATION OF UBIHYDROQUINONES AND UBIQUINONES

A process for the preparation of ubihydroquinones and ubiquinones by condensation of a prenol or isoprenol with a hydroquinone or derivative thereof in the presence of 0.005 - 1.0 mol% of a catalyst which is a Broensted-acid, a Lewis-acid from the group consisting of a derivative of Bi or In or an element of group 3 of the periodic table of the elements, a heteropolyacid, an NH- or a CH-acidic compound, and optionally oxidizing the ubihydroquinone obtained.

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New strategies for the synthesis of polyphenols, compounds with antioxidant properties contained in every kind of plants, are discussed. Syntheses of different classes of polyphenols, namely ubiquinones, present in many natural systems in which electron-transfer mechanisms are involved, hydroxytyrosol, one of the main components of the phenol fraction in olives, and flavonoids, widespread in the plant kingdom, were approached by simple and environmentally sustainable methods.

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The present invention relates to a method of efficiently producing reduced coenzyme Q10 having excellent qualities which is useful as an ingredient in foods, functional nutritive foods, specific health foods, nutritional supplements, nutrients, animal drugs, drinks, feeds, cosmetics, medicines, remedies, preventive drugs, etc. This method is suitable for industrial production thereof. It is possible to handle reduced coenzyme Q10 in state of being protected from oxidation by molecular oxygen by bringing the reduced coenzyme Q10 in contact with a solvent containing a strong acid. Furthermore, when reduced coenzyme Q10 is crystallized in the presence of a strong acid, crystallization can be carried out while the formation of oxidized coenzyme Q10 as a by product is minimized, and, then high-quality crystals thereof can be produced.

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