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58186-27-9

Idebenone

CAS: 58186-27-9

Molecular Formula: C19H30O5

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58186-27-9 - Names and Identifiers

Name Idebenone
Synonyms cv 2619
Idebenon
Idebenone
IDEBENONE(P)
cv 2619 idebenone
6-(10-Hydroxydecyl)ubiquinone
2-(10-hydroxydecyl)-5,6-dimethoxy-3-methyl-p-benzoquinone
2-(10-Hydroxydecyl)-5,6-dimethoxy-3-methyl-2,5-cyclohexadiene-1,4-dione
2-(10-hydroxydecyl)-5,6-dimethoxy-3-methyl-cyclohexa-2,5-diene-1,4-dione
2,5-Cyclohexadiene-1,4-dione, 5,6-dimethoxy-2-(10-hydroxydecyl)-3-methyl-
CAS 58186-27-9
EINECS 1308068-626-2
InChI InChI=1/C19H30O5/c1-14-15(12-10-8-6-4-5-7-9-11-13-20)17(22)19(24-3)18(23-2)16(14)21/h20H,4-13H2,1-3H3
InChIKey JGPMMRGNQUBGND-UHFFFAOYSA-N

58186-27-9 - Physico-chemical Properties

Molecular FormulaC19H30O5
Molar Mass338.44
Density1.08±0.1 g/cm3(Predicted)
Melting Point52-550C
Boling Point497.3±45.0 °C(Predicted)
Flash Point170.1°C
Solubility Soluble in DMSO (up to 25 mg/ml).
Vapor Presure5.67E-12mmHg at 25°C
Appearanceneat
ColorOrange
Merck14,4888
pKa15.20±0.10(Predicted)
Storage Conditionroom temp
StabilityStable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.
Refractive Index1.502
Physical and Chemical PropertiesOrange needle-like crystals are obtained from petroleum ether with a melting point of 46~50 ℃. Crystallized from hexane-ethyl acetate, melting point 52~53 ℃. Easily soluble in chloroform, methanol or anhydrous ethanol, easily soluble in ethyl acetate, soluble in most organic solvents, hardly soluble in n-hexane, and almost insoluble in water.
UseUsed as a cerebral circulation improving drug, intelligent promoting drug

58186-27-9 - Risk and Safety

Hazard SymbolsXi - Irritant
Irritant
WGK Germany3
RTECSGU5290000

58186-27-9 - Nature

Open Data Verified Data

Orange needle-like crystals from petroleum ether, melting point 46-50 °c. Crystals were obtained from hexane-ethyl acetate, melting point 52-53 °c. Very soluble in chloroform, methanol or ethanol, soluble in ethyl acetate, soluble in most organic solvents, insoluble in hexane, almost insoluble in water.

Last Update：2024-01-02 23:10:35

58186-27-9 - Preparation Method

Open Data Verified Data

3,4,5-trimethoxytoluene, 10-acetoxydecanoyl chloride and aluminum trichloride in dichloroethane were cooled in an ice bath and the reaction was stirred. Put into ice water, dichloromethane extraction, treated to give 6-(10-acetoxy-1-oxodecyl) -2,3-= methoxy-5-methylphenol as a light brown oil. Methanol and sodium hydroxide were added thereto, stirred, the solvent was distilled off, and water was added. The precipitated crystals were filtered and vacuum dried to obtain a crude product. The crude product was dissolved in chloroform, separated by silica gel column, and eluted to collect the desired components. The solvent was distilled off and recrystallized to obtain 6-(10-hydroxy-1-oxodecyl) as white crystals. -2,3 dimethoxy-5-methylphenol. The product was mixed with acetic acid, Pd-C and perchloric acid, and hydrogenated at room temperature under normal pressure. The catalyst was filtered off, concentrated, and dichloromethane was added, washed, dried, and the solvent was distilled off to give 6-(10-hydroxydecyl)-2, 3-dimethoxy-5-methylphenol as a pale oil. The oily substance and the newly prepared Freund's salt, dimethyl formamide water monomethyl alcohol and potassium dihydrogen phosphate were mixed and stirred. After complete reaction, the mixture was diluted with water, extracted with dichloromethane, washed, dried and recrystallized to obtain idebenone.

Last Update：2022-01-01 09:09:42

58186-27-9 - Use

Open Data Verified Data

research and development of the Japan-Japan-phosphoric-acid Pharmaceutical Industry Co., Ltd. was launched in December 1988. Idebenone is a new type of anti-senile dementia specific drug and brain function metabolism and mental symptom improvement drug, and has a mild antihypertensive effect. It can activate the respiratory activity of brain mitochondria, improve the brain energy metabolism of cerebral ischemia, improve the utilization rate of glucose in the brain, increase the production of ATP in the brain, and inhibit the production of lipid peroxide by brain mitochondria, inhibition of membrane dysfunction caused by lipid peroxidation of brain mitochondrial membranes. Clinical for cerebral infarction, cerebral hemorrhage and arteriosclerosis sequelae caused by brain dysfunction, low consciousness, emotional disorders, language disorders, dementia and other patients. The drug had low toxicity.

Last Update：2022-01-01 09:09:43

58186-27-9 - Reference Information

Overview Idebenone (IDBN) chemical name is 6-(10-hydroxydecyl)-2,3-dimethoxy-5-methylbenzoquinone, is a kind of intelligent promoting drug which was developed and listed by the Japan-Japan Institute of Pharmaceutical Industry Corporation in 1986; It has an activating effect on the thread-drawing function, it can improve the metabolism of brain function and brain dysfunction, improve the utilization rate of glucose in the brain, promote the generation of ATP, improve the metabolism of neurotransmitter serotonin in the brain, it has strong antioxidant and free radical scavenging effects. In clinic, it is mainly used to treat many degenerative diseases of the central nervous system related to oxidative compression, such as Parkinson's disease, Alzheimer's disease, multi-infarct dementia, cerebral local anemia and brain failure, it is also used in the treatment of Friedreich's ataxia, and can also be used in cosmetic formulations, with free radical scavenging, inhibition of lipid peroxidation, inhibition of inflammation, inhibition of DNA damage, photoprotection, reduce pigmentation and other cosmetic efficacy.
physical and chemical properties is yellow crystal or crystalline powder, odorless. Very difficult to dissolve in water, very soluble in chloroform, methanol or ethanol, soluble in ethyl acetate, insoluble in hexane.
preparation method 1.3,4, 5-trimethoxytoluene is introduced into 10-acetoxydecanoyl or 9-methoxycarbonylnonanoyl group by a reaction of one gram of formazan, and then hydrolyzed, reduced and oxidized to obtain this product. 2.2,3-dimethoxy -5-methyl -1,4-benzoquinone in the presence of aluminum trichloride and double acyl peroxide action into acetoxy decyl, then HCl-methanol treatment of this product, or the introduction of 9 methoxycarbonyl nonalkyl group, aluminum hydride reduction and ferric chloride oxidation in the system. Using 1 method, instead of phosphorus trichloride thionyl chloride or phosphorus pentachloride preparation of acid chloride, chlorination reactant without treatment and distillation can be directly used for the next step reaction, simple operation, product quality is good. Its synthetic route is shown in Figure 1. Figure 1 for the synthesis of this product
pharmacodynamics This product is for improving brain metabolism, mental symptoms, can activate the brain mitochondrial respiratory activity, the improvement of brain energy metabolism disorder can reduce neurological symptoms, emotional disorders and passive avoidance response disorders in stroke animals and experimental cerebral ischemia animals. 1. The improvement of cerebral ischemia in brain dysfunction: ① the goods prone to stroke in spontaneously hypertensive rats (SHRSP) stroke sequelae, emotional disorders (decreased spontaneous movement, susceptible to stimulation), limb paralysis and other improvement. ② the passive avoidance response disorder can be improved in the rats with experimental cerebral infarction, experimental transient cerebral ischemia and bilateral forebrain basal injury. ③ This product can delay the onset time and death time of SHRSP spasm after ligation of both sides of common carotid artery, and can also delay the death time of Hypoxemia mice. (4) it can improve the low content of acetylcholine and the low metabolism of serotonin in the brain of experimental transient cerebral ischemia rats, and can increase the monoamine metabolites in the cerebrospinal fluid of patients with cerebrovascular disorder. 2. The improvement of cerebral energy metabolism disorder during cerebral ischemia: ① it has inhibitory effect on the decrease of ATP and the increase of lactic acid in the brain of rats with ligation of bilateral common carotid arteries and experimental transient cerebral ischemia. ② After the onset of SHRSP stroke and the destruction of the basal part of the brain in rats with low glucose utilization, this product can make the recovery. 3. Activation of brain mitochondrial respiratory activity: ① in vitro recovery of succinate and NADH oxidase activity (respiratory activity) in mitochondrial samples of injured dog brains, it can activate the function of electron transport system in rat brain mitochondria. (2) in vivo, it can inhibit the formation of lipid peroxide in rat and dog brain mitochondria, and prevent the mitochondrial membrane disorder (swelling) associated with the formation of lipid peroxide and maintain its function.
pharmacokinetics 6 patients with stroke sequela were treated with 30mg orally after meal, and the peak time was 3.31 h, the peak plasma concentration was 290 μg/ml and the Half-Life was 7.69h. The prototype of this product was not detected in urine. Patients with cerebrovascular disorders after a meal oral 30mg within 24 hours, the urinary excretion rate was 32%. Patients with cerebrovascular disorders daily oral 150mg (divided into 3 times) for 8 weeks, no obvious accumulation.
Clinical application 1. It is used for the treatment of many degenerative diseases of the central nervous system associated with oxidative compression, such as Parkinson's disease, Alzheimer's disease, multi-infarct dementia, cerebral local anemia and brain failure. 2. For the treatment of Friedreich's ataxia. 3. Treatment of cardiovascular and cerebrovascular diseases. Overview of idebenone, physical and chemical properties, preparation methods, clinical application is Ding red editing. (2015-11-19)
dosage oral: 30mg for adults, 3 times a day, after meals.
note long-term use, pay attention to check GOT, GPT, etc. The safety of this product to pregnant women has not been fully determined, and therefore disabled for pregnant women. Due to the drug can be secreted into breast milk, and thus lactating women with caution.
adverse reactions the incidence of adverse reactions was 3.77% (1193/2). ① allergy: occasional rash, etc., should be discontinued. The digestive system: occasionally Nausea, loss of appetite, stomach pain, Diarrhea. The nervous system: occasional hyperactivity, seizures, rare dizziness, staggered, excited. (4) blood: occasionally red blood cells decreased, white blood cells decreased. Liver: increased SGOT, SGPT and ALP occasionally. Kidney: occasionally increased BUN. 7 Other: occasional burnout, total cholesterol, triglyceride increased.
Chemical properties Orange needle-like crystals from petroleum ether, melting point 46-50 °c. Crystals were obtained from hexane-ethyl acetate, melting point 52-53 °c. Very soluble in chloroform, methanol or ethanol, soluble in ethyl acetate, soluble in most organic solvents, difficult to dissolve in hexane, a few insoluble in water.
Usage brain function improver, which can improve brain energy metabolism and brain function, and mild antihypertensive effect. Clinical for cerebral infarction, cerebral hemorrhage and arteriosclerosis sequelae caused by brain dysfunction, low consciousness, emotional disorders, language disorders, dementia and other patients.
stimulant for central nervous system.
used as cerebral circulation improving drug, intelligent promoting drug
production method Method 1:3,4, 5-trimethoxytoluene, 10-acetoxydecanoyl chloride and aluminum trichloride in dichloroethane were stirred for 2H with ice-bath cooling and for an additional 70H at room temperature. It was poured into ice water, extracted with dichloromethane, washed with water and dried. The solvent was distilled off to give 6-(10-acetoxy-1-oxodecyl)-2, 3-dimethoxy-5-methylphenol as a light brown oil. Methanol and sodium hydroxide were then added and stirred for 2H at room temperature. The solvent was evaporated, water was added and the pH was adjusted to PH 3 with hydrochloric acid. The precipitated crystals were filtered and dried under vacuum. The crude product was dissolved in chloroform and separated by silica gel column. The impurities were eluted with chloroform-methanol (95:5) and then with chloroform-methanol (90:10), The desired components were collected, the solvent was distilled off, and recrystallized from ether-hexane (1:3) to give 6-(10-hydroxy-1-oxodecyl)-2 as white crystals, 3-dimethoxy-5-methylphenol, melting point 66.5-68 °c, yield 63.1% (based on 3,4, 5-trimethoxytoluene). The above product was hydrogenated with acetic acid, 5% Pd-C perchloric acid and 70% perchloric acid at room temperature under atmospheric pressure for more than 20H. The catalyst was filtered off and concentrated. Methylene chloride was added, washed twice with 5% sodium bicarbonate and dried. The solvent was distilled off to give 6-(10-hydroxydecyl)-2, 3-dimethoxy-5-methylphenol as a light colored oil in 95% yield. The oil and the newly prepared Frerny's salt, dimethylformamide-water-methanol (1:1:1) and a small amount of potassium dihydrogen phosphate were stirred at 50 °c for 7 hours. After completion of the reaction, it was diluted with water, extracted with dichloromethane, washed twice with water and dried. The solvent was distilled off and recrystallized from n-hexane-diethyl ether (3:1) to obtain idebenone of orange-red needle-like crystals with a melting point of 54-55 ° C. And a yield of 69.6%. Method 2: The acyl chloride of 3,4, 5-trimethoxytoluene and sebacic acid monoethyl ester is acylated at the 2-position under the catalysis of aluminum trichloride, and then hydrolyzed. It is then reduced to Form 10-(2-hydroxy-3, 4-dimethoxy-6-methylphenyl) decanoic acid, followed by oxidation to quinone, and ethelation of a re-reduced ester group to a hydroxyl group to give idebenone. The only difference from Method 1 is that it is oxidized to quinone first and then the side chain is reduced. The operation method and method 1 are similar.
Last Update：2024-04-09 02:00:03
58186-27-9
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Hubei YoungXin Pharmaceutical Tech Co.,Ltd.
Spot supply
Product Name: Idebenone Visit Supplier Webpage Request for quotation
CAS: 58186-27-9
Tel: 0714-3999186
Email: 2853786052@qq.com
Mobile: 86+15671228036
QQ: 2853786052 Click to send a QQ message
Wechat: 15671228036
Hefei TNJ Chemical Industry Co.,Ltd.
Product Name: Idebenone Request for quotation
CAS: 58186-27-9
Tel: 0086-551-65418684
Email: sales@tnjchem.com
　　　　 info@tnjchem.com
Mobile: 0086 189 4982 3763
QQ: 2881500840 Click to send a QQ message
Wechat: 0086 189 4982 3763
WhatsApp: 0086 189 4982 3763
Product List: View Catalog
Shanghai Yuanye Bio-Technology Co., Ltd.
Multiple SpecificationsSpot supply
Product Name: Idebenone Visit Supplier Webpage Request for quotation
CAS: 58186-27-9
Tel: 18301782025
Email: 3008007409@qq.com
Mobile: 18021002903
QQ: 3008007409 Click to send a QQ message
Wechat: 18301782025
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58186-27-9
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