Ensorb

Base Information

• Chemical Name: Ensorb
• CAS No.: 303-98-0
• Molecular Formula: C59H90O4
• Molecular Weight: 863.361
• Hs Code.: 29146990
• Mol file: 303-98-0.mol

Synonyms:2,3-dimethoxy-5-methyl-6-decaprenylbenzoquinone;Bio-Quinone Q10;co-enzyme Q10;coenzyme Q10;coenzyme Q10, (Z,Z,Z,Z,Z,Z,E,E,E)-isomer;coenzyme Q10, ion (1-), (all-E)-isomer;CoQ 10;CoQ10;Q-ter;ubidecarenone;ubiquinone 10;ubiquinone 50;ubiquinone Q10;ubisemiquinone;ubisemiquinone radical;Coenzyme Q;Ubiquinone

Chemical Property of Ensorb

Chemical Property:

• Appearance/Colour: yellow-orange crystalline powder
• Vapor Pressure: 1.23E-30mmHg at 25°C
• Melting Point: 49-51 °C
• Refractive Index: 1.525
• Boiling Point: 869 °C at 760 mmHg
• Flash Point: 324.5 °C
• PSA: 52.60000
• Density: 0.97 g/cm³
• LogP: 17.85390
• Storage Temp.: −20°C
• Sensitive.: Light Sensitive
• Solubility.: Soluble in chloroform.
• XLogP3: 19.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 31
• Exact Mass: 862.68391135
• Heavy Atom Count: 63
• Complexity: 1840

Purity/Quality:

99%min ^*data from raw suppliers

Coenzyme Q10 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(=O)C(=C(C1=O)OC)OC)CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C
• Isomeric SMILES: CC1=C(C(=O)C(=C(C1=O)OC)OC)C/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CC/C=C(/C)\CC/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CCC=C(C)C
• Recent ClinicalTrials: Role of Coenzyme Q in ADHD in Children
• Indications: 1. the treatment of heart failure and dilated cardiomyopathy: Ubidecarenone has excellent repair effect on myocardial ischemia (hypoxia) defects caused by heart disease, and can significantly improve cardiac hypertrophy and dilated cardiomyopathy. 2. blood pressure lowering,and lipid-lowering effects: a 12-week double-blind test for 46 men and 37 female with high blood pressure found that patients whose daily consumption of 120 mg (twice) , blood pressure dropped by an average of about 17 mm Hg. 3. the antioxidant activity, application in the cardiovascular system: prevention of atherosclerosis, myocardial infarction and thrombosis, as a strong antioxidant, Ubidecarenone can resist the oxidation of LDL in the blood, reduce the formation of atherosclerosis, prevent myocardial infarction and thrombosis. 4. the treatment of congestive heart weakness: In 1970, the scientist Folkers shown that compared with the conventional drugs, daily consumption of 100 mg of Ubidecarenone for two consecutive months ,significantly improved 2/3 patient's heart function in clinical trials. 5. for post-surgical treatment of heart disease: compared with the patients who had not used Ubidecarenone, the recovery time of patients eating Ubidecarenone is greatly reduced. 6. delaying the development of heart failure, reduce mortality: Ubidecarenone can treat chest pain caused by the narrowing of coronary arteries, enhance heart beating capacity and hypoxia tolerance. 7. anti-aging and beauty: Ubidecarenone can help the skin to prevent oxidative damage to DNA, and anti-light aging, reduce wrinkles. Ubidecarenone are also commonly used in a variety of anti-wrinkle, firming and skin repair formulations. But extensive research believed that: exogenous Ubidecarenone, is far less direct and effective than the endogenous Ubidecarenone against human aging. 8. anti-fatigue: Ubidecarenone can protect and restore the integrity of the biofilm structure, it plays the membrane potential stabilizing role, it is the body's non-specific immune enhancer, and therefore exhibits excellent anti-fatigue action, maintaining the cells at a state of good health.
• Uses: 1. Coenzyme medicines. It is also an important antioxidant and immune enhancer. For congestive heart failure, arrhythmias, sinus tachycardia, premature beats, hypertension and cancer adjuvant therapy for acute and chronic viral hepatitis and subacute hepatic necrosis comprehensive treatment. In addition, it is also tested in primary and secondary aldosteronism, cerebrovascular disorders and hemorrhagic shock. during the application, user may appear nausea, upset stomach, loss of appetite and other phenomena, urticaria, and a transient palpitations occasionally appear. 2. Cardiovascular medicine. 3. It can be widely used in food, cosmetics, dietary supplements and other industries. Coenzyme drugs, is also an important antioxidant and immune enhancer. 4. It can activate human cells and cellular energy nutrition, it can improve human immunity, enhance anti-oxidation, anti-aging and enhance human activity. In addition, recent studies indicate that the product also has anti-tumor effects, for advanced metastatic cancer have a certain effect in clinical, have a significant effect in the prevention of coronary heart disease, alleviate periodontitis, treatment of duodenal and gastric ulcer, strengthen the immune system function and relieve angina . Because Ubidecarenone is effective and without side effects. It is used in pharmaceuticals, cosmetics, food additives and other industries. Ubidecarenone is also known as coenzyme Q10 it is a powerful antioxidant that is naturally found in the cells. It acts as a free radical neutraliser. Coenzyme Q10 (CoQ10) is a naturally occurring quinone found throughout the body in cell membranes, primarily in mitochondrial membranes, with highest concentrations in the heart, lungs, liver, kidneys, spleen, pancreas, and adrenal glands. It is a component of the electron transport chain and participates in aerobic cellular respiration, generating energy in the form of ATP. In its reduced form, CoQ10 acts as an antioxidant, preventing the formation of reactive oxygen species. CoQ10 deficiencies have been associated with heart failure, hypertension, parkinsonism, mitochondrial encephalomyopathies, and other chronic diseases.[Cayman Chemical]
• Production method: The residue was extracted from pig heart after the extraction of cytochrome C. Proceeding as follows: pig heart residues [saponification] saponification liquid [extract] extract [concentration, filtration] concentrate [adsorption] [washing] [eluted] eluent [concentrated] yellow oil [crystalline] [dried] Ubidecarenone from fresh pig heart extract 60.9mg per kilogram of Ubidecarenone. It may also be produced by fermentation. U.S. Patents 3068295,389153 and 4062879 describe the synthesis route of Ubidecarenone. Preparation of the drug substance Method One, alcohol-alkali saponification Preparation of Saponification: to take the pig heart residues, pressed dry weight, according to the weight of the dry residue add 300g/L Industrial Coke sexual gallic acid, stirring, add alcohol-alkaline solution (dry residue weight 3-3.5 times the amount of ethanol, 320g/L sodium hydroxide), was heated under reflux with stirring 25-30min, rapidly cooled to room temperature, the liquid was saponified. Pig heart residues [NaOH] → [Coke sexual gallic acid, ethanol] saponification solution Preparation of concentrate liquid: to take saponification liquid, immediately added 1/10 volume of petroleum ether or 120 petrol to extract 3-4 times, stirring, layered to give the extract. Washed with water to nearly neutral, concentrated to 1/10 of the original volumevbelow 40 ℃, cooled and allowed to stand overnight at less-5 ℃, filtration, concentrate. Saponification solution [petroleum] → extract [<40 ℃] → concentrate Preparation of Ubidecarenone: refined products, the concentrate was subjected to silica gel column chromatography, eluting with petroleum ether, 10% ethyl ether-petroleum ether eluate, solvent recovery, a yellow oil. Ethanol heating dissolved, filtered, and the filtrate was allowed to stand, cooling and crystallization, vacuum drying, Ubidecarenone refined products.v Concentrate [silica gel, ether-petroleum ether] → eluent [ethanol] → Ubidecarenone refined products Method two, alcohol-ether mixed solvent extraction Preparation of the Ubidecarenone crude product: pig heart residue is taken followed by a 1.5-fold amount of ethanol, V: V ether = 3: 1 mixed solvent, heat extraction 3-4 times, each time 15-20min, cooled to room temperature, filtered, and combined the extracts . Concentrated, added water, extracted with petroleum ether , the extraction was concentrated and the yellow oil concentration is Ubidecarenone crude product. Preparation of the finished Ubidecarenone product: Ubidecarenone crude product was dissolved in acetone, set at-10 ℃ to precipitate impurities, filtrated, the filtration was evaporated acetone, added a small amount of petroleum ether to dissolve, silica gel column chromatography, add ethanol crystallized to give Ubidecarenone products. Ubidecarenone crude product [silica gel] → [acetone, ethanol] finished Ubidecarenone Method three, bovine heart slags Bovine Heart residue [10% NaOH-80% ethanol] → brown-black solution [extract] → gasoline extract [washing] → orange butter layer [concentrated] → Ubidecarenone crude product [fat analysis] → clear oil [chromatography] Ubidecarenone → eluent [frozen concentrated to] → orange oil [crystalline sulfate] → finished Ubidecarenone Injection Characters: this product is a yellow clear liquid, with the extension of storage time, there will be precipitated orange, can be set at hot water heating for several minutes, shaking to dissolve, without affecting efficacy. The crystal is less stable, placed for 3-6 months, the concentration decreased about 3%-5%, up to more than 8%, but over time, the concentration decreasing rate will slow along time. Preparation: this product is sterile aqueous solution prepared by Ubidecarenone plus Tween-80 or other cosolvent .
• Description: Coenzyme Q10 (CoQ10) is a quinone that is found throughout the human body in cell membranes, primarily in mitochondrial membranes, with the highest levels in the heart, lungs, liver, kidneys, spleen, pancreas, and adrenal glands. It exists in three redox states: fully oxidized (CoQ10/ubiquinone), partially reduced (semiquinone or ubisemiquinone), and fully reduced (ubiquinol; ). CoQ10 acts as an electron shuttle in the electron transport chain via its reduction to ubiquinol between mitochondrial complexes I and II, also known as NADH dehydrogenase and succinate dehydrogenase, respectively, and mitochondrial complex III, also known as cytochrome bc1 complex. CoQ10 is also reduced to ubiquinol by ferroptosis suppressor protein 1 (FSP1) with NADPH as a cofactor, and ubiquinol traps lipid peroxyl radicals and inhibits lipid peroxidation helping to prevent ferroptosis. Mutations in genes encoding enzymes involved in CoQ10 biosynthesis lead to primary CoQ10 deficiency, which is characterized by encephalopathy, cerebellar ataxia, infantile multisystemic form, nephropathy, and isolated myopathy. Secondary CoQ10 deficiency, induced by non-genetic impaired CoQ10 biosynthesis, insufficient CoQ10 intake, or excessive CoQ10 utilization, has been observed in a variety of conditions, including ataxia-oculomotor-apraxia 1 (AOA1), mitochondrial diseases, and hypercholesteremia with statin therapy. Formulations containing CoQ10 have been used in the treatment of CoQ10 deficiency.
• Therapeutic Function: UBIDECARENONE

Technology Process of Ensorb

There total 169 articles about Ensorb which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

2-hydroxy-3,4,5-trimethoxy-6-((2E)-decaprenyl)-toluene (899809-10-0) → ubidecarenone (303-98-0,55127-92-9)

Guidance literature:

With iron(III) chloride; In dichloromethane; acetonitrile; at 0 - 5 ℃; for 0.5h; Product distribution / selectivity;

Reference yield: 95.0%

1-[(2E,6E,10E,14E,18E,22E,26E,30E,34E)-3,7,11,15,19,23,27,31,35,39-decamethyltetraconta-2,6,10,14,18,22,26,30,34,38-decaen-1-yl]-3,4-dimethoxy-2,5-bis(methoxymethoxy)-6-methylbenzene (64634-91-9) → ubidecarenone (303-98-0,55127-92-9)

Guidance literature:

With hydrogenchloride; iron(III) chloride; In ethanol; hexane; water; at 20 ℃; for 3h;

DOI:10.1002/ejoc.201200627

Reference yield: 94.0%

2-((2E,6E,10E,14E,18E,22E,26E,30E,34E)-3,7,11,15,19,23,27,31,35,39-Decamethyl-tetraconta-2,6,10,14,18,22,26,30,34,38-decaenyl)-5,6-dimethoxy-3-methyl-phenol (400010-26-6) → ubidecarenone (303-98-0,55127-92-9)

Guidance literature:

With salcomine; oxygen; In N,N-dimethyl-formamide; toluene; at 20 ℃; for 24h;

DOI:10.1021/ja021015v

upstream raw materials:

decaprenol

2,3-dimethoxy-5-methylbenzene-1,4-diol

3,7,11,15,19,23,27,31,35,39-decamethyl-1,6,10,14,18,22,26,30,34,38-tetracontadecaene-3-ol

ubiquinol

Downstream raw materials:

2-(3,7,11,15,19,23,27,31,35,39-decamethyl-tetracontyl)-5,6-dimethoxy-3-methyl-[1,4]benzoquinone

diethoxy-CoQ₁₀

Refernces

• 1、 Eto, Hirozumi,Eguchi, Chikahiko. "A Novel Solvent Effect in the Practical Synthesis of Ubiquinone-10". . p. 1597 - 1600. Retrieved 1988.
• 2、 Oh, Eun-Taek,Taek Oh, Jung,Koo, Sangho,Jin Kim, Hee,Su, Liang,Yun, Inkyun,Nam, Kyunggu,Min, Jae-Hong,Woo Kim, Joon. "Synthesis of coenzyme Q10". . p. 4954 - 4962,9. Retrieved 2020/08/24.
• 3、 -. "Novel Intermediates, Process for Their Preparation and Process for the Preparation of Coq10 Employing the Said Novel Intermediates". Page/Page column 17-18. . Retrieved 2008/12/08.