Scilliroside

from Wikipedia, the free encyclopedia
Structural formula
Structural formula of scilliroside
General
Surname Scilliroside
other names

6-β-acetoxy-3-β- (β-D-glucopyranosyloxy) -8,14-dihydroxybufa-4,20,22-trienolide

Molecular formula C 32 H 44 O 12
Brief description

Solid

External identifiers / databases
CAS number 507-60-8
EC number 208-077-4
ECHA InfoCard 100.007.344
PubChem 441871
Wikidata Q7433895
properties
Molar mass 620.69 g mol −1
Physical state

firmly

Melting point

168-170 ° C

solubility
  • poorly soluble in water
  • Easily soluble in lower alcohols, ethylene glycol, dioxane and glacial acetic acid
  • sparingly soluble acetone, chloroform and ethyl acetate
  • practically insoluble in ether
safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary
06 - Toxic or very toxic

danger

H and P phrases H: 300
P: ?
Toxicological data

0.43 mg kg −1 ( LD 50 ,  mouse ,  oral )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Scilliroside is a chemical compound from the group of substituted carboxylic acid esters and bufadienolides . Along with scillaries A , proscillaridin A and glucoscillaries A, it is one of the scilla glycosides and a glycoside of the red squill ( Scilla maritima ). The plant belongs to the Liliaceae family and is the red variation of white sea onion .

Occurrence

Scilliroside occurs naturally to about 0.0035% in the bulbs of the red variation of the sea onion, but the content changes with the time of harvest and the provenance.

properties

Scilliroside is a solid that is sparingly soluble in water. It decomposes when heated above 200 ° C. The crystals precipitating from aqueous media represent a hydrate that still gives off water in a high vacuum but is still present as a hemihydrate afterwards.

use

Scilliroside is used as a rat bait and rodenticide . It is the active ingredient of the red sea onion whose specific poisonous effect has been known in the Mediterranean countries for centuries.

safety instructions

Scilliroside is highly toxic and acts as a strong emetic by irritating the mucous membranes (except in species such as the rat that cannot vomit). In addition, it is a cardiac glycoside that produces cardiac effects similar to those of the digitalis glycosides . The minimum lethal dose (oral) of the raw sea onion extract is 145 mg / kg for the dog and 100 mg / kg for the cat.

Individual evidence

  1. ↑ a b c d e f g Entry on scilliroside in the GESTIS substance database of the IFA , accessed on December 30, 2019(JavaScript required) .
  2. ^ A b c Karl Winterfeld : Organic-chemical drug analysis . Springer-Verlag, 1965, ISBN 978-3-662-29419-2 , p. 268 ( limited preview in Google Book search).
  3. ↑ Entry on 6β-acetoxy-3beta (β-D-glucopyranosyloxy) -8,14-dihydroxybufa-4,20,22-trienolide in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on December 30, 2019 . marketer can use the harmonized classification and labeling expand .
  4. ↑ a b Entry on Scillirosid - Small Animal at CliniTox
  5. ↑ a b Richard Wegler (Ed.): Chemistry of the pesticides and pesticides . Springer, 1970, ISBN 978-3-642-46210-8 , pp. 608 ( limited preview in Google Book search).
  6. ↑ Georg Arends, Heinrich Zörnig, Hermann Hager, Georg Frerichs, Walther Kern: Hager's handbook of pharmaceutical practice for pharmacists, drug manufacturers, druggists, doctors etc. Medical officer . Springer-Verlag, 2013, ISBN 978-3-662-36329-4 , p. 1541 ( limited preview in Google Book search).
  7. ^ Felix R. Althaus: Textbook of pharmacology and toxicology for veterinary medicine 131 tables . Georg Thieme Verlag, 2010, ISBN 978-3-8304-1079-9 , p. 626 ( limited preview in Google Book search).