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Scilliroside

HCID 441871
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Basic information

CAS
507-60-8
Standard SMILES
CC(=O)O[C@@H]1C[C@]2(O)[C@H](CC[C@]3(C)[C@@H](c4ccc(=O)oc4)CC[C@@]32O)[C@@]2(C)CC[C@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)C=C12
InChIKey
LSMIOFMZNVEEBR-ICLSSMQGSA-N
Molecular formula
C32H44O12
Average molar mass
620.7 g/mol
Monoisotopic mass
620.28327683

Overview

scilliroside has been reported in Drimia maritima with data available.

Names & identifiers

Preferred name
Scilliroside
IUPAC
[(3S,6R,8S,9R,10R,13R,14R,17R)-8,14-dihydroxy-10,13-dimethyl-17-(6-oxopyran-3-yl)-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3,6,7,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-yl] acetate

Names & synonyms

SCILLIROSIDESilmurinScillirosidSilmine507-60-8Squill2815004NHO(3-beta,6-beta)scillirosideDTXSID5042374CHEBI:28332NSC-7523Scillirosidin 3-O-beta-D-glucoside
Show more names
[(3S,6R,8S,9R,10R,13R,14R,17R)-8,14-dihydroxy-10,13-dimethyl-17-(6-oxopyran-3-yl)-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3,6,7,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-yl] acetateBufa-4,20,22-trienolide, 6-(acetyloxy)-3-(beta-D-glucopyranosyloxy)-8,14-dihydroxy-, (3beta,6beta)-3-beta,6-beta-6-acetyloxy-3-(beta-d-glocopyranosyloxy)-8,14-dihydroxybufa-4,20,22-trienolide6-beta-6-(acetyloxy)-3-beta-(beta-d-glocopyranosyloxy)-8,14-dihydroxybufa-4,20,22-trienolide(3beta,6beta)-6-(Acetyloxy)-3-(beta-D-glucopyranosyloxy)-8,14-dihydroxybufa-4,20,22-trienolideRodene((3S,6R,8S,9R,10R,13R,14R,17R)-8,14-dihydroxy-10,13-dimethyl-17-(6-oxopyran-3-yl)-3-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy-2,3,6,7,9,11,12,15,16,17-decahydro-1H-cyclopenta(a)phenanthren-6-yl) acetate((3S,6R,8S,9R,10R,13R,14R,17R)-8,14-dihydroxy-10,13-dimethyl-17-(6-oxopyran-3-yl)-3-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl)oxy-2,3,6,7,9,11,12,15,16,17-decahydro-1H-cyclopenta(a)phenanthren-6-yl) acetate

Database identifiers

CAS
507-60-8
PubChem CID
441871
DTXSID
DTXSID5042374
UNII
2815004NHO

Properties

Computed structural properties

XLogP
-0.4
Topological polar surface area
192 Ų
Hydrogen bond donors
6
Hydrogen bond acceptors
12
Rotatable bonds
6
Heavy atoms
44
Formal charge
0
Complexity
1,280

Experimental & physicochemical properties

Pesticides · 2 items

Rodenticides

Active substance -> EU Pesticides database: Not approved

Color/Form · 2 items

Long prisms from dilute methanol

Long needles or prisms from methanol

Solubility · 2 items

Slightly soluble in water

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

Boiling PointDecomposes
DecompositionWhen heated to decomposition it emits acrid smoke and irritating fumes.
Melting Point · 2 items

169 °C

Rosettes of long needles from methanol. MP: 199 °C. Soluble in chloroform. The four additional sugar groups are on the sugar. /Tetraacetyl scilliroside/

Optical RotationSpecific optical rotation: -59 to -60 deg at 20 °C/D (methanol)
Other Experimental Properties

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 6 items

Danger

H300: Fatal if swallowed [Danger Acute toxicity, oral]

P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)

Danger

H300: Fatal if swallowed [Danger Acute toxicity, oral]

P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)

Hazard information

Regulatory Information · 2 items

2004/129/EC

Scilliroside: HSNO Approval: HSR004380 Approved with controls

Hazard Classes and Categories · 2 items

Acute toxicity - category 2

Acute Tox. 2 *

Safety & protection

Disposal Methods · 1 item

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.

Toxicology

Interactions · 2 items

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.

Chemistry & industry

Pharmacology

Absorption, Distribution and Excretion · 1 item

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.

Uses & manufacturing

Uses · 2 items

For scilliroside (USEPA/OPP Pesticide Code: 070801) there are 0 labels match. /SRP: Not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Used as a rodenticide. /Former use/

Methods of ManufacturingGlycoside from red squill, the red variety of Urginea maritima (L.) Baker, Liliaceae.
General Manufacturing InformationRodenticide. Red squill has been used since the 13th century ... bulbs should be dried at temperatures below 80 °C

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Compound notes

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EC Number
208-077-4
Nikkaji
J3.638B
· 3 items

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/

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.

Toxicity Summary · 1 item

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.

Plant ConcentrationsScilliroside was detected not quantified in the bulb of Urginea meritima (Liliaceae), European Squill(1).
Effluent Concentrations · 1 item

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).

Natural Pollution SourcesScilloroside 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).
Non-Human Toxicity Excerpts · 2 items

/LABORATORY ANIMALS: Acute Exposure/ A single sublethal dose of Vacor (1 mg/rat) or Silmurin (50 ug/rat) brought about dissimilar 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. Vacor and Silmurin induced differential changes in heartbeat; Vacor poisoning resulted in bradycardia, whereas Silmurin tachycardia. It is inferred that Vacor deaths may be due to bradycardia associated with atrioventricular block and that of Silmurin to delayed myocardial repolarization and tachycardia.

/LABORATORY ANIMALS: Acute Exposure/ The toxicity and efficacy of the acute rodenticide scilliroside was evaluated in the laboratory against the lesser bandicoot rat, Bandicota bengalensis. The acute oral LD50 and LD95 doses for males were 0.8 mg/kg and 2.5 mg/kg respectively, and for females were 0.5 mg/kg and 1.6 mg/kg, respectively. When caged bandicoots were given a choice between plain and poison baits, the optimum concentration of scilliroside was found to be 0.05%. Symptoms of poisoning appear from 22 to 34 min after feeding starts and the latency pattern indicated an abrupt ceasing to feed at these points. Death occurred from 2 hr to as long as 6 days after poisoning, following prolonged convulsive seizures. There appears to be aversion to scilliroside at all concentrations in food baits. Maximum mortality attained on free-choice feeding on scilliroside was 90%. Despite these disadvantages, the material may have merit as an alternative rodenticide to zinc phosphide where acute toxicants are to be used.

Antidote and Emergency Treatment · 1 item

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.

Non-Human Toxicity Values · 5 items

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