10310-32-4, Tribenoside, 三苄糖苷, CAS:10310-32-4

10310-32-4, Tribenoside,
三苄糖苷,
CAS:10310-32-4
C29H34O6 / 478.58
MFCD00801089

Tribenoside, 三苄糖苷

Ethyl 3,5,6-tri-O-benzyl-D-glucofuranoside,

Tribenoside is a vasoprotective agent with anti-allergic and anti-inflammatory activities. It inhibits agonist-induced contractions in various isolated porcine venous preparations when used at concentrations ranging from 10 to 30 µg/ml. Tribenoside inhibits compound 48/80-induced histamine release in isolated rat peritoneal cells (EC50 = 10 µg/ml). It reduces decreases in proteoglycan levels and the severity of cartilage destruction in the inflamed joints in a rabbit model of surgically induced osteoarthritis when administered at doses of 100 and 200 mg/kg per day. Formulations containing tribenoside have been used in the treatment of hemorrhoids and varicose veins.

(3R,4R,5R)-5-[(1R)-1,2-bis(phenylmethoxy)ethyl]-2-ethoxy-4-phenylmethoxy-3-oxolanol is a glycoside.

Anti-inflammatory agent used in edema of extremities, varicose veins & phlebitis.

Title: Tribenoside

CAS Registry Number: 10310-32-4

CAS Name: Ethyl 3,5,6-tris-O-(phenylmethyl)-D-glucofuranoside

Manufacturers' Codes: Ba-21401

Trademarks: Alven (Firma); Flebosan (Dukron); Glyvenol (Novartis); Hemocuron (Takeda); Venex (Recordati)

Molecular Formula: C29H34O6

Molecular Weight: 478.58

Percent Composition: C 72.78%, H 7.16%, O 20.06%

Literature References: Prepn: Druey, Huber, US 3157634 (1964 to Ciba). Pharmacology: Lecomte, C.R. Seances Soc. Biol. Ses Fil. 163, 1469 (1969); Helfer, Jaques, Pharmacology 5, 23 (1971). Increase in capillary resistance in patients with rheumatoid arthritis: W. C. Dick et al., Ann. Rheum. Dis. 28, 187 (1969). GLC determn in plasma: A. Sioufi, F. Pommier, J. Pharm. Sci. 69, 167 (1980). Excretion as hippuric acid: eidem, Eur. J. Drug Metab. Pharmacokinet. 7, 223 (1982). Review of pharmacology: R. Jaques, ibid. 15, 445-460 (1977).

Properties: bp1.2 270-280°. [a]D26 +8° (chloroform).

Boiling point: bp1.2 270-280°

Optical Rotation: [a]D26 +8° (chloroform)

Therap-Cat: Sclerosing agent.

Keywords: Sclerosing Agent.

Solubility:

DMSO: 30 mg/ml(52.24 mM)

Ethanol: 30 mg/ml(52.24 mM)

DMF: 25 mg/ml(52.24 mM)

CAS Number	10310-32-4
Product Name	Tribenoside
IUPAC Name	(3R,4R,5R)-5-[(1R)-1,2-bis(phenylmethoxy)ethyl]-2-ethoxy-4-phenylmethoxyoxolan-3-ol
Molecular Formula	C29H34O6
Molecular Weight	478.58 g/mol
InChI	InChI=1S/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
InChI Key	ULLNJSBQMBKOJH-VIVFLBMVSA-N
SMILES	CCOC1C(C(C(O1)C(COCC2=CC=CC=C2)OCC3=CC=CC=C3)OCC4=CC=CC=C4)O
Solubility	Soluble in DMSO
Synonyms	Ba 21401, Ba-21401, Ciba 21401 Ba, Ciba 21401-Ba, ethyl 3,5,6-tri-O-benzyl-D-glucofuranoside, Glyvenol, tribenol, tribenoside, tribenoside, (alpha)-isomer, tribenoside, (beta)-isomer
Canonical SMILES	CCOC1C(C(C(O1)C(COCC2=CC=CC=C2)OCC3=CC=CC=C3)OCC4=CC=CC=C4)O
Isomeric SMILES	CCOC1[C@@H]([C@H]([C@H](O1)[C@@H](COCC2=CC=CC=C2)OCC3=CC=CC=C3)OCC4=CC=CC=C4)O

CAS No: 10310-32-4 Synonyms: Tribenoside MDL No: MFCD00801089 Chemical Formula: C29H34O6 Molecular Weight: 478.58

COA:

Product name: Tribenoside CAS: 10310-32-4

M.F.: C₂₉H₃₄O₆M.W._:478.58

*Items*	*Standards*	*Results*
Appearance	Yellow clear, viscous liqiud	Complies
Solubility	Insoluble in water, easily soluble in acetone, methanol and methylene choloride	Complies
Identification	IR	Complies
Specific rotation [α]20/D, in methanol	-31 ~ -40°	-36°
Density (g/mL)	1.02-1.10	1.05
3,5,6-Tri-O-benzyl-1,2-O- isopropylidene-α-D-glucofuranose	Max 0.5%	Complies, 0.17%
Heavy metals	Max.20 ppm	Complies
TLC*	One or two spots (max. two spots)	Complies
Assay by HPLC	96%	96.6%