Tribenoside

Details:

Tribenoside Chemical Properties
alpha     D26 +8° (chloroform)
Boiling point     bp1.2 270-280°
density     1.19±0.1 g/cm3(Predicted)
storage temp.     Sealed in dry,Store in freezer, under -20°C
solubility     Practically insoluble in water, very soluble in acetone, in methanol and in methylene chloride.
pka    13.01±0.70(Predicted)
color     Pale Yellow to Light Yellow
InChIKey    ULLNJSBQMBKOJH-VIVFLBMVSA-N
CAS DataBase Reference    10310-32-4

Tribenoside Usage And Synthesis
Chemical Properties    Yellowish to pale yellow, clear, viscous liquid.
Originator    Glyvenol,Ciba,W. Germany,1967
Uses    Tribenoside is a vasoprotective drug. It’s used in the treatment of hemorrhoids as it has mild anti-inflammatory and wound healing properties.
Uses    Sclerosing agent.
Definition    ChEBI: (3R,4R,5R)-5-[(1R)-1,2-bis(phenylmethoxy)ethyl]-2-ethoxy-4-phenylmethoxy-3-oxolanol is a glycoside.
Manufacturing Process    4.9 g of 3,5,6-tribenzyl-1,2-isopropylidene glucofuranose are kept overnight at room temperature with 100 cc of N-ethanolic hydrochloric acid. Evaporation under vacuum at below 50°C is then carried out and the residue taken up in 150 cc of chloroform. The chloroform solution is thoroughly washed with sodium bicarbonate solution, dried with calcined sodium sulfate and evaporated under vacuum. The oily residue is then distilled under vacuum with a free flame. In this manner there is obtained the ethyl-3,5,6-tribenzyl_x0002_D-glucofuranoside of boiling point 270°C to 275°C under 1 mm pressure. The glucofuranose used as starting material is obtained as follows: 8.8 g of 1,2-isopropylidene-D-glucofuranose and 50.6 g of benzyl chloride are treated with a total of 28 g of potassium hydroxide in portions with cooling and stirring. The mixture is then stirred for 3 hours at 80°C to 90°C. Working up from chloroform solution and distillation at 250°C to 260°C under 0.1 mm pressure give 8.9 g of 1,2-isopropylidene-3,5,6-tribenzyl-D-glucofuranose.
Therapeutic Function    Topical venotonic
Hazard    Low toxicity by ingestion.
Contact allergens    This drug is used for the treatment, both topical and oral, of hemorrhoids. It leads to benzo c acid, that is contained in Myroxylon pereirae as well, and could be the sensitizer.