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
• Article Data: 10

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

Chemical Properties

Bright Yellow Solid

Uses

Different sources of media describe the Uses of 303-97-9 differently. You can refer to the following data:
1. Antibacterial and antioxidant for preventing and treating cancer.
2. This product is provided as delivered and specified by the issuing Pharmacopoeia. All information provided in support of this product, including SDS and any product information leaflets have been developed and issued under the Authority of the Issuing Pharmacopoeia. For further information and support please go to the website of the issuing Pharmacopoeia. Ubidecarenone impurity D may be used as an internal standard for the determination of the ubiquinol-10 in biological samples by high performance chromatography method(HPLC) and liquid chromatography tandem mass spectrometry to evaluate the oxidative stress.
3. Coenzyme Q9 has been used to investigate its interference in the detection of coenzyme Q10 (CoQ10) by fluorescent spectrophotometer (FS-ECA). It has also been used as an analyte in chromatographic analysis of different biological samples that correspond to different genetic conditions.

General Description

Coenzyme Q9 (Ubiquinone-9; Ubi-9) is a 9 isoprenyl group member of a family of ubiquinones that share a quinine chemical group but differ in the number of isoprenyl chemical subunits in their tail. The CoQ compounds are lipid soluble components of cell membranes.

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

• 605-94-7 2,3-Dimethoxy-5-methyl-1,4-benzoquinone 
• 72247-20-2 Trimethyl-((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-nonaenyl)-stannane 
• 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 
• 13190-97-1 solanesol 
• 3066-90-8 2,3-dimethoxy-5-methylbenzene-1,4-diol 
• 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 

Downstream Products

• 114832-93-8 1,4-dibenzyloxy-2,3-dimethoxy-5-methyl-6-(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,34'-nonaenyl)benzene 
• 96358-54-2 2,3-dimethoxy-5-methyl-6-(36-chloro-3,7,11,15,19,23,27,31,35-nonamethylhexatriacont-2E,6E,10E,14E,18E,22E,26E,30E,34E-nonaenyl)-1,4-benzoquinone 
• 96381-15-6 2,3-dimethoxy-5-methyl-6-(34-hydroxy-35-methylene-3,7,11,15,19,23,27,31,35-octamethylhexatriacont-2E,6E,10E,14E,18E,22E,26E,30E-octaenyl)-1,4-benzoquinone 
• 96358-53-1 2,3-dimethoxy-5-methyl-6-(34-acetoxy-35-methylene-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 
• 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 
• 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 
• 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 
• 303-98-0 ubidecarenone 
• 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 
• 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 
• 114832-94-9 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 
• 303-98-0 34'Z-ubiquinone-10 
• 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 

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

Disclosed are Compounds that block off-notes in consumables and methods of blocking off-notes in consumables including off-notes provided by artificial sweeteners including aspartame, Saccharin, acesulfame K (Acesulfame potassium), sucralose and cyclamate; and including stevioside, swingle extract, glyccerhizin, perillartine, naringin dihydrochalcone, neohesperidine dihydrochalcone, mogroside V, rubusoside, rubus extract, and rebaudioside A.

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.

METHOD OF STABILIZING REDUCED COENZYME Q10 AND METHOD OF ACIDIC CRYSTALLIZATION

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.