Coenzyme Q10 Chemical Properties

Melting point:

49-51 °C

Boiling point:

715.32°C (rough estimate)

Density 

0.9145 (rough estimate)

refractive index 

1.4760 (estimate)

storage temp. 

-20°C

solubility 

Soluble in chloroform.

form 

Solid

color 

Light Orange to Dark Orange

Sensitive 

Light Sensitive

Merck 

14,9843

BRN 

1900141

Stability:

Stable, but may be light or heat sensitive. Store in the dark at -20 C. Incompatible with strong oxidizing agents.

InChIKey

ACTIUHUUMQJHFO-DQXDOXBUSA-N

LogP

19.119 (est)

CAS DataBase Reference

303-98-0(CAS DataBase Reference)

EPA Substance Registry System

Ubidecarenone (303-98-0)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

22-24/25-26

WGK Germany 

3

RTECS 

DK3900000

F 

8-10

TSCA 

Yes

HS Code 

29146990

Toxicity

LD50 intramuscular in mouse: > 500mg/kg

MSDS

• Language:English Provider:SigmaAldrich

Coenzyme Q10 Usage And Synthesis

Outline

Ubidecarenone is a small molecule lipid-soluble quinone compounds widely found in plant and animal cells, its structure is similar to the structure of vitamin K, used alone or in combination with vitamin E as a powerful antioxidant. It is required for energy generation (ATP) circulation. It promotes phosphorylation reaction and protect the structural integrity of the biofilm oxidation function. Ubidecarenone of different sources are different with its side chain prenyl units number, Ubidecarenone of humans and mammals are 10 prenyl units, thus it is called Ubidecarenone. Ubidecarenone plays an important role in proton translocation in vivo respiratory chain and electron transfer , it is the cell respiration and cell metabolism activator, and also an important antioxidant and non-specific immune enhancer. Modern biology study found that excess free radicals in the body can cause damage to the genetic material of the cell membrane, and macro manifested as aging, cancer and other symptoms. Free radical scavenging process is commonly referred to as "antioxidant." We know that life activities is driven by a variety of enzymes. Enzymes are large proteins, enzymes need some small molecules to help in exercising some functions , these substances are called "coenzyme." Ubidecarenone exists in the mitochondria within the cells. Mitochondria are the place to produce energy in cells, many enzymes and other molecules are involved in the energy production process, and Ubidecarenone is one of the indispensable one. In the organs with more energy consumption in the human body , the content of Ubidecarenone will be relatively high, such as heart, liver, kidney, kidney, spleen, pancreas, adrenal, the content is particularly rich. The total body content of Ubidecarenone is only 500-1500mg, the content changes with age, it decreased for most people after the age of 20 . Lack of Ubidecarenone are usually caused heart failure, gum disease, arrhythmias, stroke, hypertension (blood pressure, food), heart disease, arteriosclerosis, cancer, Parkinson's disease, muscular dystrophy, AIDS. Ubidecarenone can successfully prevent and treat these diseases, from 40 years ago when it was found and isolated, Ubidecarenone has been conducted hundreds of clinical studies, a lot of evidence shows that nutrition is necessary for health (health food) .

Chemical Properties

Ubidecarenone occurs as a yellow to orange crystalline powder. It is odorless and has no taste. It is soluble in diethyl ether, very slightly soluble in ethanol (99.5), and practically insoluble in water. It is gradually decomposed and colored by light.

Ubidecarenone, or coenzyme Q10, is a fat-soluble compound primarily synthesised by the body and also consumed in the diet. Ubidecarenone is a physiological element present in the cells as a component of the mitochondrial respiratory chain. It is involved in the process of energy production by mitochondria and functions as an antioxidant in cell membranes and lipoproteins.It acts directly on the oxidative phosphorylation processes for the production of energy (formation of ATP) through metabolic, especially aerobical, pathways.

Discovery History

Ubidecarenone was discovered in 1957, Dr. Frederick Crane identified the chemical structure in 1958 , and received the highest honor of the American Chemical Society Priestly Medal. He is known as the father of the study of Ubidecarenone, he proposed Ubidecarenone to play an important role in heart function. In real life, Dr. Frederick Crane has been taking Q10 for 40 years, until his death at 91 years old, he had been an active energetic professors engaged in research activities. In 1978, Dr. Peter (Peter), the University of Edinburgh, Scotland, first discovered Ubidecarenone must participate in human cells energy production , and thus obtained Nobel prize. Today, Europe, Japan and other developed countries have incorporated the content of Ubidecarenone in the human body as a measure of the level of of the health of the body as an important indicator.
Ubidecarenone exists in every cell of the human body, the main role is to drive the body cells to produce energy, it can accelerate cell renewal, stimulate cell activity, thus greatly promoting the cells' ability to uptake nutrients. Ubidecarenone ingredients in skin care products can effectively help the skin cells to active the absorption of other nutrients in skin care products , so skin care ingredients is no longer simply to stay on the skin surface, when reaching the underlying skin, it can quickly provide additional protecting energy for skin protection factor. If a person becomes a car for analogy, the Ubidecarenone is equivalent to the "engine", without engine, the car can not travel, without Ubidecarenone, the body can not produce the "power" to carry out daily operations.
The above information is edited by the Chemicalbook of Tian Ye.

Pharmacological effects

1. It can reduce myocardial contractility decrease , reduce creatine phosphate and ATP content decrease in acute ischemia, maintaining morphology of ischemic myocardium mitochondria, having a protective effect for myocardial ischemia.
2. It can increase cardiac output, reduced peripheral resistance, conducive to anti-heart failure treatment, may inhibit the synthesis and secretion of aldosterone, and block its effects on the kidney tubules.
3. Under hypoxic conditions in vitro perfusion animals ventricular muscle, it can shorten the duration of the action potential, resulting in ventricular arrhythmia threshold than the control animals.
4. It can decrease peripheral vascular resistance, and owns anti-aldosterone effect.
5. Ubidecarenone owns anti-cardiotoxic effects and hepatoprotective effect of doxorubicin.

Biological Activity

Coenzyme Q10 (ubiquinone, ubidecarenone, coenzyme Q) is a 1,4-benzoquinone, where Q refers to the quinone chemical group, and 10 refers to the number of isoprenyl chemical subunits in its tail. This oil-soluble, vitamin-like substance is found in all cells as part of the electron transfer chain responsible for energy production and provides 95% of the body’s energy in the form of ATP. There are three redox states of coenzyme Q10: fully oxidized (ubiquinone), semiquinone (ubisemiquinone), and fully reduced (ubiquinol). A natural resource of coenzyme Q10 is fish and shellfish although animal’s foods such heart will have very high concentrations reflecting mitochondrial levels in such tissue (Crane, 2001). It has been used to reduce wrinkles (changes in the dermal matrix), reduce cell death and DNA oxidative stress, increase ATP systhesis, and suppress collagenase following UVA irradiation (Muta-Takada et al., 2009). For example, coenzyme Q10 accelerates production of basement membrane components, i.e. laminin 332 and type IV and VII collagens, in keratinocytes and fibroblasts, respectively. However, it has no effect on type I collagen production in fibroblasts. Coenzyme Q10 also shows protective effects against cell death induced by ROS in keratinocytes (Muta-Takada et al., 2009).

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.

What role in the human body

Ubidecarenone(303-98-0) has two main functions in the body, the first is playing an important role in the process of transferring nutrients into energy in the mitochondria, the second is a clear anti-lipid peroxidation effect.
It is well known that free radicals generation is the the main reasons of aging. Most cells contain between 500 to 2,000 mitochondria. These mitochondrial act like a little "energy factory", transferring the food we eat into energy, thereby to maintain the operation of life. Ubidecarenone is a metabolic activator, it can activate cell respiration, accelerate the production of the energy needed by the body----adenosine triphosphate (ATP). Studies have shown that once human blood Ubidecarenone levels reduced by 25%, the body's major organs (especially the heart) will no maintain optimum operating condition because of insufficient energy. Studies have shown that antioxidants can prevent and reduce the risk of incidence of many diseases. Ubidecarenone can be synthesized in the human tissue, after age 20, the synthesis will be weakened, the liver loses the ability to synthesize Ubidecarenone, while Ubidecarenone is also difficult to obtain from the food supplement. In addition to age, bad habits, stress and infections can affect the body, resulting in not enough supply of Ubidecarenone, the body will gradually reduce the natural coenzyme in cells, which means that the body's cells gradually lose their protection. Thus accelerating the skin aging process.

Toxicity

Acute toxicity test in mice and rats shows the LD50 greater than 4000mg/Kg. In subacute toxicity experiments, the male and female Wistar rats were given daily 40mg, 200mg and 1000mg/Kg, sharing five weeks, male and female rabbits daily 6mg, 60mg and 600mg/Kg, continuous application of 23 days, no special finding in the test animal blood , urine test, and morphological changes. In the chronic toxicity test, the male and female Wistar rats were given daily 6mg, 60mg and 600mg/Kg 26 consecutive weeks, no special finding in the general state of the tested animals , blood and urine tests, and morphological changes.

Uses

1. Coenzyme(303-98-0) 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.

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.

Chemical Properties

Yellow-Orange Crystalline Powder

Originator

Neuquinon,Eisai,Japan,1974

Occurrence

Coenzyme Q10 is found in dietary sources. Coenzyme Qmolecules have side chains of differentlengths in different types of organismsbut function in similar ways.

Uses

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]

Uses

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.

Definition

ChEBI: Coenzyme Q10 is a ubiquinone having a side chain of 10 isoprenoid units. In the naturally occurring isomer, all isoprenyl double bonds are in the E- configuration. It has a role as a human metabolite, a ferroptosis inhibitor and an antioxidant. It is found in animal organs and yeast with active in the citric acid cycle in carbohydrate metabolism.

Manufacturing Process

A small fermentation tank (5,000 parts by volume capacity) was charged with 3,000 parts by volume of a culture medium (pH 6.0) comprising 3% glucose, 1% polypepton, 0.5% yeast extract and 0.5% malt extract. The medium was sterilized by heating in a conventional manner and cooled. This medium was inoculated with 150 parts by volume of a pre-culture of Sporidiobolus ruinenii CBS-5001, which had been prepared by growing the same strain on a medium of the same composition as above at 28°C for one day. The inoculated medium was incubated at 28°C and under agitation at 800 rpm with sparging at a rate of 3,000 parts by volume per minute for 24 hours. During this fermentation period, the medium was maintained at pH 6.0 with ammonia and sulfuric acid.
The resultant fermentation broth was centrifuged to harvest the microbial cells, and they were washed with water and centrifuged a second time, whereupon a living cell paste was obtained. (There was obtained an amount of cells equivalent to 54 parts on a dry basis, which contained 920 μg of ubiquinone-10 per gram of dry cells.)
The moist cells were suspended in 750 parts of volume of ethanol and extracted by warming at 60°C for 1 hour. A total of 3 extractions were carried out in a similar manner and the extracts were pooled, diluted with water and further extracted three times with 1,000 parts of volume portions of n_x0002_hexane. The n-hexane layer was concentrated to dryness under reduced pressure to recover 4.12 parts of a yellow oil. This oily residue was dissolved in 6 parts by volume of benzene and passed through a column (500 parts by volume capacity) packed with Floridil (100 to 200 meshes). Elution was carried out using benzene and the eluate was collected in 10 parts by volume fractions. Each fraction was analyzed by thin-layer chromatography and color reaction and the fractions rich in ubiquinone-10 were pooled and concentrated under reduced pressure. By this procedure was obtained 0.562 part of a yellow oil. This product was dissolved in 5 parts by volume of chloroform, coated onto a thin layer plate of silica gel GF254 (silica gel with calcium sulfate) and developed with benzene. The fractions corresponding to ubiquinone-10 were extracted, whereby 0.054 part of a yellow oil was obtained. This oil was dissolved in 10 parts by volume of ethanol and allowed to cool, whereupon 0.029 part of yellow crystals of ubiquinone-10 were obtained, its melting point 48° to 50°C.
There are also synthetic routes to the ubiquinones as described in US Patents 3,068,295; 3,896,153 and 4,062,879.

Therapeutic Function

UBIDECARENONE

General Description

Ubidecarenone, referred to as coenzyme Q, is abundantly available in human cells, with major proportions being present in vital body organs such as heart and kidneys. It plays an important role in cell metabolism owing to its significant contribution to the electron transport pathway. It is a strong antioxidant and acts as an essential enzyme catalyst in mitochondrial oxidative phosphorylation.

Biological Activity

Component of the mitochondrial transporter chain that behaves as a powerful antioxidant. Displays neuroprotective activity.

Biochem/physiol Actions

Coenzyme Q10 is an endogenous cellular antioxidant and an essential component of the electron transfer chain. CoQ10 takes part in aerobic cellular respiration and generation of energy in the form of ATP.

Side effects

Mild side effects might include digestive problems such as: Upper abdominal pain; Loss of appetite; Nausea and vomiting; Diarrhea.
Other possible side effects may include: Headaches and dizziness; Insomnia; Fatigue; Skin itching or rashes; Irritability or agitation.

Drug interactions

Coenzyme Q10 supplements may interact with some antihypertensive (those that lower blood pressure) and chemotherapy drugs. Coenzyme Q10 may increase the risk of blood clots in people who take the anticoagulant warfarin by decreasing warfarin's effectiveness.

Purification Methods

Purify it by recrystallisation from EtOH, EtOH/Me2CO or Et2O/EtOH and by chromatography on silica gel using isoPrOH/Et2O (3:1) to give orange crystals. It has max 270nm ( 15,170) in pet ether. [Terao et al. J Org Chem 44 868 1979, NMR and MS: Naruta et al. J Org Chem 45 4097 1980, IR: Lester et al. Biochem Biophys Acta 42 1278 1959, NMR: Planta et al. Helv Chim Acta 42 1278 1959; Morton Biochemical Spectroscopy (Adam Hilger, London, 1975) p 491].

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