Bis(3,5-di-tert-butyl-4-hydroxyphenyl) Mercaptole Acetone
probucol
CAS: 23288-49-5
Molecular Formula: C31H48O2S2
Bis(3,5-di-tert-butyl-4-hydroxyphenyl) Mercaptole Acetone - Names and Identifiers
| Name | probucol |
| Synonyms | bisbid probucol PROBUCOL biphenabid bisphenabid Probucol-[13C3] Probucol (200 mg) Bis(3,5-di-tert-butyl-4-hydroxyphenyl) Mercaptole Acetone 4,4'-(propane-2,2-diyldisulfanediyl)bis(2,6-di-tert-butylphenol) 4,4'-((1-methylethylidene)bis(thio))bis(2,6-bis(1,1-dimethylethyl)-pheno |
| CAS | 23288-49-5 |
| EINECS | 245-560-9 |
| InChI | InChI=1/C31H48O2S2/c1-27(2,3)21-15-19(16-22(25(21)32)28(4,5)6)34-31(13,14)35-20-17-23(29(7,8)9)26(33)24(18-20)30(10,11)12/h15-18,32-33H,1-14H3 |
| InChIKey | FYPMFJGVHOHGLL-UHFFFAOYSA-N |
Bis(3,5-di-tert-butyl-4-hydroxyphenyl) Mercaptole Acetone - Physico-chemical Properties
| Molecular Formula | C31H48O2S2 |
| Molar Mass | 516.84 |
| Density | 1.0008 (rough estimate) |
| Melting Point | 126-128°C |
| Boling Point | 571.58°C (rough estimate) |
| Flash Point | 264.9°C |
| Solubility | It is extremely soluble in chloroform, soluble in ethanol, and insoluble in water. |
| Vapor Presure | 1.46E-12mmHg at 25°C |
| Appearance | White solid |
| Color | White to Off-White |
| Merck | 14,7755 |
| pKa | 10.27±0.70(Predicted) |
| Storage Condition | Keep in dark place,Sealed in dry,Room Temperature |
| Sensitive | Easily absorbing moisture |
| Refractive Index | 1.5341 (estimate) |
| MDL | MFCD00079281 |
| Physical and Chemical Properties | White crystals from ethanol, melting point 124.5~126 deg C; From isopropanol to fine yellow crystals, melting point 125~126.5 deg C. |
| Use | Anti-atherosclerotic agents, for the prevention and treatment of coronary heart disease, regulating blood lipids |
Bis(3,5-di-tert-butyl-4-hydroxyphenyl) Mercaptole Acetone - Risk and Safety
| WGK Germany | 2 |
| RTECS | AL3705000 |
| HS Code | 2930902000 |
Bis(3,5-di-tert-butyl-4-hydroxyphenyl) Mercaptole Acetone - Reference Information
| lipid-lowering drug | probucol is a lipid-lowering drug with strong antioxidant, anti-inflammatory and anti-atherosclerosis effects. it is the only synthetic antioxidant certified by the food and drug administration of the United States. it was listed in the United States as early as 2070s, and its chemical structure is unique to the structure and type of known lipid-regulating drugs. There are two easily oxidized phenolic hydroxyl groups in the molecular structure of Probucol, which have a strong ability to capture oxygen ions. The phenolic hydroxyl groups combine with oxygen ions to form stable phenolic oxygen groups. At the same time, the phenolic hydroxyl group is fat-soluble, and it is mostly distributed on the surface of the lipoprotein monolayer composed of phospholipids and free cholesterol in the lipoprotein particles. Arterial wall cells can prevent water-soluble antioxidant substances in plasma from entering the endothelium through a microporous filtration structure. Therefore, probucol is an antioxidant substance that can be enriched in low-density lipoprotein and easily enter the arterial intima after being ingested, which is beneficial to the treatment of anti-atherosclerosis. Probucol is a lipid regulator and has anti-atherosclerotic effect. Its lipid-lowering effect is to reduce blood cholesterol and low-density lipoprotein by reducing cholesterol synthesis and promoting cholesterol decomposition. It also changes the nature and function of high-density lipoprotein subtypes and reduces blood high-density lipoprotein cholesterol. The clinical significance of lowering high-density lipoprotein cholesterol is unknown. This product has little effect on blood triglycerides. This product has a significant antioxidant effect, can inhibit the formation of foam cells, delay the formation of atherosclerotic plaque, and subside the formed atherosclerotic plaque. It is clinically suitable for all kinds of mild to moderate hyperlipidemia, and is compatible with other drugs in the treatment of severe hyperlipidemia; it is used in patients with high risk of atherosclerosis, and it can protect the oxidation of arterial wall cells, namely endothelial cells, So that atherosclerotic plaque decreases or disappears. Studies have shown that the antioxidant effects of probucol are 5-6 times, l6 times, 95.5 times and 104 times of vitamin E, nimodipine, verapamil and captopril respectively. Later studies have proved that its antioxidant activity can cause obvious anti-atherosclerosis effect. In recent years, clinical studies have found that although probucol reduces high-density lipoprotein (HDL), it does not aggravate atherosclerosis. On the contrary, it shows strong anti-atherosclerosis activity. In addition, probucol also has powerful anti-aging and treatment of restenosis after angioplasty. Therefore, probucol has received clinical attention again. |
| indication | probucol, as the only antioxidant drug certified by the U.S. Food and Drug Administration (FDA), is an antioxidant substance that can accumulate in LDL and easily enter the arterial intima after being ingested. The main pharmacological effects of probucol include reducing cholesterol synthesis and promoting cholesterol decomposition, changing the nature and function of high-density lipoprotein subtypes, antioxidant effects, inhibiting the formation of foam cells, delaying the formation of atherosclerotic plaques, and regressing the formation of atherosclerotic lesions. Used for type Ⅱa hyperlipoproteinemia, combined with other lipid-lowering drugs can be used for type Ⅱb and Ⅲ, Ⅳ hyperlipoproteinemia. Fig. 1 is the structural formula of probucol |
| pharmacokinetics | absorption and blood drug concentration animal studies show that intestines and stomach can only absorb 2%-8% of one oral dose, and the absorption of human intestines and stomach is also weak, but the individual differences of patients are large, and taking medicine immediately after meals will increase absorption. After taking 3-4 months, the blood drug concentration reached a stable level. The blood drug concentration decreased by 60% after 6 weeks of drug withdrawal, and by 80% after 6 months of drug withdrawal. Distribution animal experiments show that probucol mainly accumulates in adipose tissue, adrenal glands, liver, bile and milk; the 90% of probucol in blood is distributed in serum and 10% in red blood cells; the 95% of probucol in serum is distributed in lipoprotein Part, and probucol in lipoprotein is mainly distributed in low-density lipid protein and very low-density lipid protein. Metabolism and excretion of metabolic products are unknown. 84% is excreted from feces and 2% from urine. |
| adverse reactions | 1. the most common adverse reactions of this product are gastrointestinal discomfort, the incidence of diarrhea is about 10%, as well as flatulence, abdominal pain, nausea and vomiting. 2. Rare reactions include headache, dizziness, paresthesia, insomnia, tinnitus, rash, skin itching, etc. Anaphylaxis of angioneurotic edema has been reported. 4. Rare serious adverse reactions include ECG QT interval prolongation, ventricular tachycardia, thrombocytopenia, etc. (2016-03-11) |
| taboo | 1. those who are allergic to this product are prohibited. 2. Because this product can cause ECG QT interval prolongation and severe ventricular arrhythmia, it is forbidden in the following situations: ① Recent myocardial damage, such as new and near myocardial infarction. ②Severe ventricular arrhythmia, such as bradycardia. (3) Cardiac syncope or unexplained syncope. ④ Those with prolonged QT interval. ⑤ Those who are applying drugs that extend the QT interval. ⑥ Low blood potassium or magnesium. |
| precautions | 1. taking this product can temporarily increase blood aminotransferase, bilirubin, creatine phosphokinase, uric acid and urea nitrogen. 2. The QT interval of electrocardiogram should be checked regularly during taking this product. 3. During medication, a low-fat and low-cholesterol diet should be used. 4.FDA classified the pregnancy safety of this drug as Class B. |
| drug interaction | 1. when this product is combined with drugs that can cause arrhythmia, such as tricyclic antidepressants, class I and class III antiarrhythmic drugs and phenothiazine drugs, attention should be paid to the increased risk of adverse reactions. 2. This product can strengthen the anticoagulant effect of coumarin drugs. 3. This product can strengthen the effect of hypoglycemic drugs. 4. When this product is combined with cyclosporine, it can reduce the blood concentration of the latter. |
| use | has the effect of lowering plasma cholesterol, but has no effect on very low density lipoprotein and no triglyceride lowering effect. It is used for type Ⅱ α hyperlipoprotein disease, combined with lipid-lowering drugs that lower triglycerides, and can also be used for type Ⅱ B, Ⅲ and Ⅳ hyperlipoproteinemia. Anti-atherosclerotic disease, prevent and treat coronary heart disease, and adjust blood lipids. |
| production method | 47.5g(0.2 mo1)2,6-di-tert-butyl-4-mercaptophenol dissolved in 50ml of methanol, heated to 50 ℃, added catalytic concentrated hydrochloric acid (1ml), and then added 5.8g(0.1 mo1) acetone. The reaction temperature was raised to 60 ℃ and reacted at 60~65 ℃ for 1.5h. Cool, dilute with water and about 10ml aqueous sodium bicarbonate solution, and then extract with ether. Concentrate the extract, and the residue is recrystallized successively with ethanol and isopropanol to obtain probucol with a melting point of 125~126 ℃. The 2, 6-di-tert-butyl-4-mercaptophenol used in the preparation can be 2, 6-di-tert-butylphenol as raw material, and is reacted with sulfur or sulfur chloride to obtain polysulfide, and then by reduction. It is also possible to directly obtain 2, 6-di-tert-butyl-4-mercaptophenol from 2, 6-di-tert-butylphenol through the following reaction. |
Last Update：2024-04-10 22:29:15
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Multiple SpecificationsSpot supply
Product Name: Probucol Visit Supplier Webpage Request for quotationCAS: 23288-49-5
Tel: 18301782025
Email: 3008007409@qq.com
Mobile: 18021002903
QQ: 3008007409
Wechat: 18301782025
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