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 |
Molecular Formula | C19H30O5 |
Molar Mass | 338.44 |
Density | 1.08±0.1 g/cm3(Predicted) |
Melting Point | 52-550C |
Boling Point | 497.3±45.0 °C(Predicted) |
Flash Point | 170.1°C |
Solubility | Soluble in DMSO (up to 25 mg/ml). |
Vapor Presure | 5.67E-12mmHg at 25°C |
Appearance | neat |
Color | Orange |
Merck | 14,4888 |
pKa | 15.20±0.10(Predicted) |
Storage Condition | room temp |
Stability | Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months. |
Refractive Index | 1.502 |
Physical and Chemical Properties | Orange 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. |
Use | Used as a cerebral circulation improving drug, intelligent promoting drug |
Hazard Symbols | Xi - Irritant |
WGK Germany | 3 |
RTECS | GU5290000 |
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.
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.
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.