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Escin

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Escin Basic information

Product Name:
Escin
Synonyms:
  • BETA-AESCIN
  • ESCIN
  • Chestnuts extract
  • AESCIN
  • (2S,3S,4S,5R,6R)-6-[[(3S,4R,4aR,6aR,6bS,8R,8aS,9S,10S,12aR,14aR,14bS)-9-Acetyloxy-8-hydroxy-4,8a-bis(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-10-[(Z)-2-methylbut-2-enoyl]oxy-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-4-hydroxy-3,5-bis[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]oxane-2-carboxylic acid
  • a-4700
  • aescusan
  • amorphousaescin
CAS:
6805-41-0
MF:
C55H86O24
MW:
1131.26
EINECS:
229-880-6
Product Categories:
  • Inhibitors
  • Herb extract
Mol File:
6805-41-0.mol
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Escin Chemical Properties

Melting point:
224.5°C
Boiling point:
764.81°C (rough estimate)
Density 
1.1200 (rough estimate)
refractive index 
1.6500 (estimate)
storage temp. 
4°C, protect from light
solubility 
Soluble in methanol.
form 
powder
color 
white
Merck 
13,3730
Stability:
Hygroscopic
CAS DataBase Reference
6805-41-0
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Safety Information

Hazard Codes 
Xn
Risk Statements 
22-20/22
Safety Statements 
22-24/25
RIDADR 
UN 3077 9 / PGIII
WGK Germany 
2
RTECS 
KF6296000

MSDS

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Escin Usage And Synthesis

Chemical Properties

saponin mixture

Originator

Aescin,Sinochem

Uses

membrane permeabilizer

Uses

escin is a saponin occurring in the seed of the horse chestnut tree.

Uses

Escin, a natural mixture of triterpenoid saponins isolated from horse chestnut (Aesculus hippocastanum) seeds, is used and studied as a vasoprotective anti-inflammatory, anti-edematous and anti-nociceptive agent. It may be used to study its pharmacokinetics, safety and efficacy as a chemosensitizer and modulator of NF-κ B cell signaling.

Manufacturing Process

The 1st method of preparation of escin (US Patent No. 3,238,190):
500 g of pulverized horse chestnut seeds were extracted two times for 1 hour with 2.5 L each of aqueous 50% methanol with stirring. The solution was filtered, additional methanol was added thereto to increase the methanol concentration to 65%, and then it was filtered again. The obtained solution containing the extracted saponin had a pH of 5 and was passed through a column of 500 ml (wet volume) of cation exchange resin (Lewatit S-100 of Farben-fabriken Bayer A.G.) which had been treated with 65% methanolic 1% sulfuric acid and then had been washed neutral with 65% methanol. The solution leaving the resin had a pH in the range of about 3 to 4 and was concentrated by distillation to about 4/5 of its original volume. On cooling, crystallization of the escin started and the solution was allowed to stand until the crystallization had been completed. Escin having a melting point of 224- 226°C was obtained in a yield of 2%, calculated on the starting material.
The 2st method of preparations of escin (US Patent No. 3,163,636):
An ethereal solution of 1 kg of cholesterol is added to 100 kg of a 10% aqueous-alcoholic horse extract. The resulting emulsion is stirred at 90°C for 1 hour, while the ether is distilled off. The water insoluble saponin-cholesterol precipitate is centrifuged and washed with cold water until the wash water is colorless. The precipitate is air-dried at room temperature. The resulting dustfine powder is extracted with ether in a Soxhlet apparatus for 10 days. The residue is treated with 20 kg of methanol and the undissolved material is filtered off. The yellowish methanol solution is treated with activated charcoal until it is colorless. The methanol is distilled off in a vacuum, and the residue is dried over phosphorus pentoxide in a vacuum not exceeding 1 mm Hg. The yield of pure sodium escinate obtained thereby is about 0.8 kg (8%).

Therapeutic Function

Antiedemic, Capillary protective

General Description

This substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG

Flammability and Explosibility

Non flammable

EscinSupplier

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