CYMARIN Chemical Properties

Melting point:

148°C

alpha 

D20 +39.2° (methanol); D22 +39.0° (c = 1.7 in chloroform)

Boiling point:

540.83°C (rough estimate)

Density 

1.1277 (rough estimate)

refractive index 

1.5500 (estimate)

storage temp. 

2-8°C

pka

13.55±0.70(Predicted)

BRN 

101370

LogP

0.640

Safety Information

Hazard Codes 

T,T+

Risk Statements 

23/25-33-26/27/28-41

Safety Statements 

45-36/37/39-36/37-28-26

RIDADR 

UN 3462 6.1/PG 2

WGK Germany 

3

RTECS 

GZ5600000

F 

8-10-23

HazardClass 

6.1(b)

PackingGroup 

III

Toxicity

LD50 i.v. in rats: 24.8±1.8 mg/kg (Vogel, Kluge)

MSDS

• Language:English Provider:SigmaAldrich

CYMARIN Usage And Synthesis

Originator

Alvonal,Goumldecke

Uses

Cymarin is a pure allelochemicals that is a potent growth inhibitor in plants.

Uses

Cymarin was used to study the effect of cardiac glycosides on vascular smooth muscles and ion transport.

Definition

ChEBI: Cymarin is a cardenolide glycoside.

Manufacturing Process

Finely ground seeds of Castilloa elastica (3550 g) are percolated with sufficient light petroleum (boiling point 60°-80°C) to ensure removal of all the fat. The mart is dried with a current of air and percolated with chloroform until no further color is obtained with alkaline m-dinitrobenzene. The percolate is evaporated under reduced pressure, the residue triturated with dry ether (750 ml) and filtered. The residue (69.75 g) is washed with dry ether, dried, and some of the washed residue (20 g) is dissolved in a benzene-chloroform mixture (50 ml), comprising one part benzene to two parts chloroform by volume, and is absorbed on to a column of alumina (7x32 cm), previously deactivated with 10% acetic acid [hereinafter referred to as Column (l)] and eluted with the same solvent mixture.
The compositions of the following fractions (collected from Column (I)) are identified by paper chromatography using Whatman No. 1 paper [Registered Trade Mark] and the aforementioned benzene-chloroform mixture.
Column (I). Fraction: (a) a pigment; (b) a substance of Rf 0.66; (c) a small quantity of a substance of Rf 0.66 and a substance of Rf 0.45; (d) a substance of Rf 0.45.
Fraction (c) is obtained from the column and concentrated. The solid residue is dissolved in the aforementioned benzene-chloroform mixture (15 ml) and fractionated further on a second deactivated alumina column (4x30cm). From this column [hereinafter referred to as Column (II)] the following fractions are collected and identified using the same chromatographic system as was used for identifying the fractions of Column (I).
Column (II). Fraction: (a) a substance of Rf 0.66; (b) a trace of a substance of Rf 0.66; (c) a substance of Rf 0.45.
The fractions (d) of Column (I) and (c) of Column (II) are combined and evaporated and the residue (80 g) crystallized from methanol and ether followed by further re-crystallization from dilute alcohol. On heating to 120°C under a pressure of 0.01 mm/Hg, the crystals Iost water to give a compound, cymarin, which has an [α]d 22 =+39.0°. The [α]d 20 of cymarin (obtained from another source) in methanol is + 39.3°.
Alternatively, fractional crystallization may be used in place of adsorption chromatography
Cumarin may be also prepared from seeds of Strophantus Kombe

Therapeutic Function

Cardiotonic

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

Biochem/physiol Actions

Cymarin is a cardiac glycoside and is classified as cardiotonic steroid. It inhibits ion transport by decreasing the activity of (Na-K)-ATPase.

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