Digitonin

Title: Digitonin
CAS Registry Number: 11024-24-1
Additional Names: Digitin
Molecular Formula: C56H92O29
Molecular Weight: 1229.31
Percent Composition: C 54.71%, H 7.54%, O 37.74%
Literature References: Obtained from the seeds of Digitalis purpurea L., Scrophulariaceae. Extraction procedure: Gisvold, J. Am. Pharm. Assoc. 23, 664 (1934). Purification of commercial digitonin and its separation into two fractions: G. Ruhenstroth-Bauer, P. M. Breitenfeld, Z. Physiol. Chem. 302, 111 (1955). Structure: Tschesche, Wulff, Tetrahedron 19, 621 (1963). Use as clinical reagent: H. H. Leffler, Am. J. Clin. Pathol. 31, 310 (1959).
Properties: Crystals from alc, sinters 225°. Indistinct mp 235-240°. [a]D20 -54° (0.45 g in 15.8 ml methanol). One gram dissolves in 57 ml abs alc, in 220 ml 95% alc. Practically insol in water, forming a soapy suspension. Also practically insol in chloroform, ether.
Melting point: Indistinct mp 235-240°
Optical Rotation: [a]D20 -54° (0.45 g in 15.8 ml methanol)
Use: Clinical reagent (cholesterol determination).
Digitoxigenin Digitoxin Digitoxose Diglyme Digoxigenin

Digitonin
Digitonin CASCC.png
Identifiers
CAS number 11024-24-1 YesY
PubChem 25444
ChemSpider 23753 YesY
EC-number 234-255-6
KEGG C00765 N
ChEMBL CHEMBL404811 N
Jmol-3D images Image 1
Properties
Molecular formula C56H92O29
Molar mass 1,229.31 g mol−1
Chiral rotation [α]D −47 to −49° (10 g/100 ml 75% acetic acid at 25 °C)
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Digitonin is a glycoside obtained from Digitalis purpurea; the aglycone is digitogenin, a spirostan steroid. Used as a detergent, it effectively water-solubilizes lipids. As such, it has several membrane-related applications in biochemistry, including solubilizing membrane proteins, precipitating cholesterol, and permeabilizing cell membranes.

Digitonin is sometimes confused with the cardiac drug digoxin (sometimes also called digitalis or digitoxin), but has no heart-related effects.