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Home > Encyclopedia > Scilliroside

Scilliroside

Scilliroside structure

Scilliroside 

structure
  • CAS No:

    507-60-8

  • Formula:

    C32H44O12

  • Chemical Name:

    Scilliroside

  • Synonyms:

    Bufa-4,20,22-trienolide,6-(acetyloxy)-3-(β-D-glucopyranosyloxy)-8,14-dihydroxy-,(3β,6β)-;Scilliroside;(3β,6β)-6-(Acetyloxy)-3-(β-D-glucopyranosyloxy)-8,14-dihydroxybufa-4,20,22-trienolide;Silmurin;NSC 7523;35-98-3;1329-65-3;11017-26-8;28932-86-7

  • Categories:

    Biochemical Engineering  >  Saccharides

Scilliroside Basic Attributes

620.68456

620.68

208-077-4

2815004NHO

DTXSID5042374

Long prisms from dilute methanol|Long needles or prisms from methanol

Characteristics

196.35000

0.64270

1.45g/cm3

169 °C

794.4ºC at 760mmHg

252.3ºC

1.621

Freely soluble in the lower alcohols, in ethylene glycol, dioxane, glacial acetic acid. Slightly soluble in acetone, chloroform, ethyl acetate. Practically insoluble in ether, petroleum ether

2.06X10-23 mm Hg at 25 deg C (est)

LD50 in mice (mg/kg): 0.471 s.c.; 0.440 orally (Dybing)

D20 -59 to -60° (methanol)

Henry's Law constant = 2.09X10-21 atm-cu m/mol at 25 °C (est)

The crystals are solvated and lose about 8% of their weight in high vacuum, but retain 1/2 mol H2O.|Dried red squill powder loses its scilliroside content on storage and when exposed to the atmosphere|Indistinct MP 168-170 °C, decomposes 200 °C /Scilliroside hemihydrate/

Safety Information

I

6.1(a)

2810

28

36/37-45

T+

P264, P270, P301+P310, P321, P330, P405, P501

H300

SRP: Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.

|Danger|H300: Fatal if swallowed [Danger Acute toxicity, oral]|P264, P270, P301+P310, P321, P330, P405, and P501

It was estimated that 0.3 kg of scilliroside was released into the Rhine River following the Sandoz warehouse fire on November 1, 1986, in Schweizerhalle, Basel Switzerland. The compound was not detected at any of the four downstream sampling locations(1).

Toxicity

IDENTIFICATION AND USE: Scilliroside is a solid; a rodenticide that has been used since the 13th century. HUMAN EXPOSURE AND TOXICITY: There are no data. ANIMAL STUDIES: A single sublethal dose 50 ug/rat brought about changes in cardiac physiology of bandicoot rats. Delayed myocardial repolarization and stress on cardiac tissues were noticed. Elevation of S-T segment above the isoelectric axis diagnostic of recent myocardial infarction was observed. It induced tachycardia. It is inferred that deaths may be due to delayed myocardial repolarization and tachycardia. Mammals, other than rodents, are unlikely to be poisoned. Injection of the glycosides leads to effects typical of digitalis: alterations in cardiac impulse conduction and arrhythmias.

Palytoxin stimulated a cation-dependent short-circuit current (Isc) in rat distal and proximal colon in a concentration-dependent fashion when applied to the mucosal surface of the tissue. The distal colon exhibited a higher sensitivity to the toxin. The palytoxin-induced Isc was blocked by vanadate but was resistant to ouabain or scilliroside, suggesting the conversion of a vanadate-sensitive H+/K+-ATPase into an electrogenic cation transporter. Cation substitution experiments with basolaterally depolarized tissues suggested an apparent permeability of the palytoxin-induced conductance of Na+>K+>Li+. Immunohistochemical control experiments confirmed the absence of the Na+/K+-ATPase in the apical membrane. Consequently, the pore-forming action of palytoxin is not restricted to Na+/K+-ATPase but is also observed with the colonic H+/K+-ATPase.|Distension of the rat colon descendens in vitro by a hydrostatic gradient induced an increase in short-circuit current (Isc). In a mucosa-submucosa preparation containing the plexus submucosus, the increase in Isc was biphasic with a half-time of about 200 s for the spontaneous returning to the baseline. The time course was monophasic in a mucosa preparation without the plexus submucosus. The increase in Isc in the mucosa-submucosa preparation was inhibited by an inhibitor of phospholipase A2, quinacrine, and by indomethacin, tetrodotoxin or atropine; each of these compounds also abolished the second phase of the response. In contrast, only indomethacin was effective in reducing the increase in Isc in the mucosa preparation. In both preparations the response to distension was inhibited by scilliroside, by replacement of Cl- with gluconate, and by administration of frusemide or the chloride channel blocker, anthracene-9-carboxylic acid. The results indicate that distension induces chloride secretion by causing the release of prostaglandins, which act indirectly, i.e. mediated by the submucosal plexus, and directly at the epithelium.

LD50 Rat oral 430 ug/kg|LD50 Mouse oral 350 ug/kg|LD50 Mouse sc 471 ug/kg|LD50 Cat iv 130 ug/kg|LD50 Chicken oral 400 mg/kg

Scilloroside occurs naturally in red squill, the red variety of Urginea maritima L. (Liliaceae)(1). Urginea maritima has a number of scientific names of which two are listed here: Drimea maritima and Scilla maritima(2).

Drug Information

Red squill is a little-used rodenticide, consisting of the inner portions of a small cabbage plant grown in eastern Mediterranean countries. Its toxic properties have been known since ancient times and are probably due to cardiac glycosides. For several reasons, mammals other than rodents are unlikely to be poisoned: (1) red squill is intensely nauseant, so that animals which vomit (rodents do not) are unlikely to retain the poison; (2) the glycoside is not efficiently absorbed from the gut; and (3) absorbed glycoside is rapidly excreted. Injection of the glycosides leads to effects typical of digitalis: alterations in cardiac impulse conduction and arrhythmias.

The purpose of this study was to evaluate the capacity of specific anti-digoxin Fab fragments to bind to and neutralize scilliroside and proscillaridin in acute poisoning. Apparent affinity constants were determined with values of 2.6 10(8)M-1 for scilliroside and 3.8 10(7)M-1 for proscillaridin. These results are in accordance with a possible in-vivo neutralization of these toxins.

scilliroside

Scilliroside Use and Manufacturing

Methods of Manufacturing

Glycoside from red squill, the red variety of Urginea maritima (L.) Baker, Liliaceae.

Rodenticide. Red squill has been used since the 13th century ... bulbs should be dried at temperatures below 80 °C

Agrochemicals -> Rodenticides

Computed Properties

Molecular Weight:620.7
XLogP3:-0.4
Hydrogen Bond Donor Count:6
Hydrogen Bond Acceptor Count:12
Rotatable Bond Count:6
Exact Mass:620.28327683
Monoisotopic Mass:620.28327683
Topological Polar Surface Area:192
Heavy Atom Count:44
Complexity:1280
Defined Atom Stereocenter Count:13
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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