Name | bucillamine |
Synonyms | sa96 de-019 Tiobutarit bucillamine thiobutarit BUCILLAMINE N-(2-Mercaptoisobutyryl)cysteine N-(2-methyl-2-sulfanylpropanoyl)cysteine N-(2-methyl-2-sulfanylpropanoyl)-L-cysteine L-Cysteine, N-(2-mercapto-2-methyl-1-oxopropyl)- (R)-3-Mercapto-2-(2-Mercapto-2-MethylpropanaMido)propanoic acid |
CAS | 65002-17-7 |
InChI | InChI=1/C7H13NO3S2/c1-7(2,13)6(11)8-4(3-12)5(9)10/h4,12-13H,3H2,1-2H3,(H,8,11)(H,9,10)/t4-/m0/s1 |
Molecular Formula | C7H13NO3S2 |
Molar Mass | 223.31 |
Density | 1.3934 (rough estimate) |
Melting Point | 119-123°C |
Boling Point | 438.0±45.0 °C(Predicted) |
Specific Rotation(α) | D25 +32.3° (c = 1.0 in ethanol) |
Flash Point | 218.7°C |
Solubility | DMSO (Very Slightly), Ethanol (Slightly), Methanol (Slightly), Water (Slightly) |
Vapor Presure | 6.77E-09mmHg at 25°C |
Appearance | Solid |
Color | White to Pale Yellow |
pKa | 3.01±0.10(Predicted) |
Storage Condition | Hygroscopic, -20°C Freezer, Under Inert Atmosphere |
Stability | Air Sensitive, Hygroscopic, Unstable in Solution |
Refractive Index | 1.6370 (estimate) |
Physical and Chemical Properties | White Crystal or crystalline powder, slightly odorous. Soluble in methanol, ethanol or acetic acid, soluble in chloroform, ethyl ether or ethyl acetate, very slightly soluble in water. The melting point was 139-140 °c. [Α] d 25 32.3 °(C = 1.0, ethanol). Acute toxicity LD50 mice (mg/kg):2285 intraperitoneal injection, 989.6 intravenous injection. Acute toxicity LD50 male and female mice, male and female rats (mg/kg):4118,3892,4074,2961 oral; 1546, 1250,2165,2009 subcutaneous injection; 1348,1501,1375,1035 intravenous injection. |
Toxicity | LD50 in mice (mg/kg): 2285 i.p.; 989.6 i.v. (Fujita, 1981) |
Use | for the treatment of chronic joint rheumatism. |
production method | S-benzyl-2-mercapto-2-methylpropionic acid (63.1g,0.30 mo1) reaction with thionyl chloride (39.3g, 0.33 mol) to give S-benzyl-2-mercapto-2-methylpropionyl chloride. In addition, S-benzyl-L-cysteine (73.9g,0.35 mo1) was dissolved in 1 mol/L sodium hydroxide solution (0.70 ML, mo1) and cooled with an ice bath, the propionyl chloride derivative obtained above was added dropwise with stirring, and further stirred for 1H after addition. After acidification with hydrochloric acid, it was extracted with ethyl acetate. The extract was washed with water, dried over anhydrous sodium sulfate, and concentrated. The residue was chromatographed on a silica gel column, eluting with benzene-ethyl acetate (1:1). The eluent was evaporated under reduced pressure to give 89.6g of an oil in 74% yield. The oil obtained above (89.6g,0.222mol) was dissolved in 21.2 of liquid ammonia and sodium metal (0.917g, MOL) was added in small portions with stirring. When the reaction was complete, ammonium chloride (59.4g,1.11 mol) was added and the ammonia was distilled off. The residue was dissolved with water. The aqueous layer was separated, washed with ethyl acetate and then acidified with hydrochloric acid under cooling. The precipitate resulting from acidification was extracted with ethyl acetate. The extract was washed with water, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and recrystallized from ethyl acetate to give 40.1g of buxilamine in 81% yield with a melting point of 139-140 °c. |