10310-32-4

Basic information

• Product Name: Tribenoside
• Synonyms: Glivenol;Glucofuranoside, ethyl 3,5,6-tri-O-benzyl- (7CI);Glucofuranoside, ethyl 3,5,6-tri-O-benzyl-, D- (8CI);Glyvenal;Glyvenol;Hemocuron;TBGF;Tribenzoside
• CAS NO: 10310-32-4
• Molecular Formula: C₂₉H₃₄O₆
• Molecular Weight: 478.57666
• EINECS: 233-687-2
• Mol File: 10310-32-4.mol
• Article Data: 1

Chemical Properties

• Boiling Point: bp1.2 270-280°
• Flash Point: 328.085 °C
• Appearance: /
• Density: 1.196 g/cm³
• Vapor Pressure: 3.55E-16mmHg at 25°C
• Refractive Index: 1.59
• Storage Temp.: -20°C
• Solubility: Practically insoluble in water, very soluble in acetone, in methanol and in methylene chloride.
• PKA: 13.01±0.70(Predicted)
• CAS DataBase Reference: Tribenoside(CAS DataBase Reference)
• NIST Chemistry Reference: Tribenoside(10310-32-4)
• EPA Substance Registry System: Tribenoside(10310-32-4)

Safety Data

• Hazardous Substances Data: 10310-32-4(Hazardous Substances Data)

Usage

Chemical Properties

Yellowish to pale yellow, clear, viscous liquid.

Originator

Glyvenol,Ciba,W. Germany,1967

Uses

Different sources of media describe the Uses of 10310-32-4 differently. You can refer to the following data:
1. Tribenoside is a vasoprotective drug. It’s used in the treatment of hemorrhoids as it has mild anti-inflammatory and wound healing properties.
2. Sclerosing agent.

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.

InChI:InChI=1/C29H34O6/c1-2-32-29-26(30)28(34-20-24-16-10-5-11-17-24)27(35-29)25(33-19-23-14-8-4-9-15-23)21-31-18-22-12-6-3-7-13-22/h3-17,25-30H,2,18-21H2,1H3/t25?,26-,27-,28-,29-/m1/s1

Synthetic route

1,2-O-isopropylidene-α-D-gluco-/β-L-idofuranose (253328-56-2) + benzyl chloride (100-44-7) → tribenoside (10310-32-4)

Conditions	Yield
Stage #1: 1,2-O-isopropylidene-α-D-gluco-/β-L-idofuranose In dimethyl sulfoxide at 30℃; for 1h; Stage #2: benzyl chloride In dimethyl sulfoxide at 30℃; for 1h; Temperature;

Upstream product

• 253328-56-2 1,2-O-isopropylidene-α-D-gluco-/β-L-idofuranose 
• 100-44-7 benzyl chloride 

Relevant articles and documents

Synthetic method of tribenoside

The invention discloses a synthetic method of tribenoside. A tribenoside finished product is finally synthesized by using monoacetone glucose and benzyl chloride under a certain condition, and can directly reach a medical standard. The synthetic method makes up a domestic blank in the aspect of synthesizing the tribenoside, and also optimizes synthetic methods of the tribenoside in other countries. By use of the synthetic method, the amount of ''three wastes'' is greatly reduced, a solvent can be recovered, the yield is increased, the process flow is shortened, the purity is improved, the operation is simple and convenient, and the safety is improved.