CYMARIN

CYMARIN Basic information
Product Name:CYMARIN
Synonyms:CIMARIN;CYMARIN;CYMARINE;3β-[(3-O-Methyl-2,6-dideoxy-β-D-ribo-hexopyranosyl)oxy]-5,14-dihydroxy-19-oxo-5β-card-20(22)-enolide;WV-90043a;20(22),5BETA-CARDENOLID-19-AL-3BETA,5BETA,14BETA-TRIOL 3BETA-MIXED GLYCOSIDES;K STROPHANTHIN;K-STROPHANTHIN-A
CAS:508-77-0
MF:C30H44O9
MW:548.66
EINECS:208-087-9
Product Categories:Cardioglycosides & Glycosides;Carbohydrates;Carbohydrates A to;Carbohydrates P-ZBiochemicals and Reagents;Polysaccharide
Mol File:508-77-0.mol
CYMARIN Structure
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
pka13.55±0.70(Predicted)
BRN 101370
LogP0.640
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
8-10-23
HazardClass 6.1(b)
PackingGroup III
ToxicityLD50 i.v. in rats: 24.8±1.8 mg/kg (Vogel, Kluge)
MSDS Information
ProviderLanguage
SigmaAldrich English
CYMARIN Usage And Synthesis
OriginatorAlvonal,Goumldecke
UsesCymarin is a pure allelochemicals that is a potent growth inhibitor in plants.
UsesCymarin was used to study the effect of cardiac glycosides on vascular smooth muscles and ion transport.
DefinitionChEBI: Cymarin is a cardenolide glycoside.
Manufacturing ProcessFinely 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 FunctionCardiotonic
General DescriptionThis 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 ActionsCymarin is a cardiac glycoside and is classified as cardiotonic steroid. It inhibits ion transport by decreasing the activity of (Na-K)-ATPase.
CYMARIN Preparation Products And Raw materials
Preparation ProductsSTROPHANTHIDIN
2-TRIDECENOIC ACID 1,4-PENTANEDIOL 2,3-DIMETHYLCYCLOHEXANOL 3-METHYL-3-HEXANOL Dibutoxymethane TRANS-2-HEXEN-1-OL 1-O-Methyl-2-deoxy-D-ribose K-STROPHANTHIN 1,3-DIMETHYLCYCLOPENTANOL CYMARIN TRANS-2-METHYLCYCLOHEXANOL HYDROXYCITRONELLOL 1,14-TETRADECANEDIOL 3-METHYL-3-NONANOL VINYLCYCLOPENTANE Dipropylene glycol monomethyl ether K-strophanthin-beta Methyl acrylate

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