508-77-0

Basic information

• Product Name: CYMARIN
• Synonyms: 20(22),5BETA-CARDENOLID-19-AL-3BETA,5BETA,14BETA-TRIOL 3BETA-MIXED GLYCOSIDES;CIMARIN;CYMARIN;CYMARINE;K STROPHANTHIN;K-STROPHANTHIN-A;K-STROPHANTHIN-ALPHA;K-STROPHANTHIDIN-D-CYMAROSIDE
• CAS NO: 508-77-0
• Molecular Formula: C30H44O9
• Molecular Weight: 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

Chemical Properties

• Melting Point: 148°C
• Boiling Point: 540.83°C (rough estimate)
• Flash Point: 232.7 ºC
• Appearance: /
• Density: 1.1277 (rough estimate)
• Vapor Pressure: 4.46E-24mmHg at 25°C
• Refractive Index: 1.5500 (estimate)
• Storage Temp.: 2-8°C
• PKA: 13.55±0.70(Predicted)
• BRN: 101370
• CAS DataBase Reference: CYMARIN(CAS DataBase Reference)
• NIST Chemistry Reference: CYMARIN(508-77-0)
• EPA Substance Registry System: CYMARIN(508-77-0)

Safety Data

• Hazard Codes: T,T+
• 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
• Hazardous Substances Data: 508-77-0(Hazardous Substances Data)

Usage

Uses

Used in Plant Growth Regulation:
Cymarin is used as a growth inhibitor in plants, helping to control and manage plant growth.
Used in Pharmaceutical Industry:
Cymarin is used as a cardiac glycoside for studying the effects of vascular smooth muscles and ion transport. This helps in understanding the mechanisms of action of cardiac glycosides and their potential therapeutic applications.

Originator

Alvonal,Goumldecke

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 chromatographyCumarin may be also prepared from seeds of Strophantus Kombe

Therapeutic Function

Cardiotonic

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.

InChI:InChI=1/C30H44O9/c1-17-26(33)23(36-3)13-25(38-17)39-19-4-9-28(16-31)21-5-8-27(2)20(18-12-24(32)37-15-18)7-11-30(27,35)22(21)6-10-29(28,34)14-19/h12,16-17,19-23,25-26,33-35H,4-11,13-15H2,1-3H3/t17-,19+,20-,21+,22+,23+,25+,26-,27-,28+,29+,30+/m1/s1

Downstream Products

• 66-28-4 strophanthidin