Chemical structure of digitonin
| |
| |
Names | |
---|---|
Other names
Digitin
| |
Identifiers | |
3D model (
JSmol)
|
|
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.031.129 |
EC Number |
|
KEGG | |
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
Properties | |
C56H92O29 | |
Molar mass | 1229.323 g·mol−1 |
Appearance | White to off-white powder |
Melting point | 244.0–248.5 °C (471.2–479.3 °F; 517.1–521.6 K) [1] |
Chiral rotation ([α]D)
|
-40° (589.3 nm; 20 °C) [1] |
Hazards | |
Lethal dose or concentration (LD, LC): | |
LD50 (
median dose)
|
23 mg/kg (rat, intravenous)
[2]
4 mg/kg (mouse, intravenous) [3] |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
Digitonin is a steroidal saponin (saraponin) obtained from the foxglove plant Digitalis purpurea. Its aglycone is digitogenin, a spirostan steroid. It has been investigated as a detergent, as it effectively water-solubilizes lipids. As such, it has several potential membrane-related applications in biochemistry, including solubilizing membrane proteins, precipitating cholesterol, and permeabilizing cell membranes. [4] [5]
Digitonin is sometimes confused with the cardiac drugs digoxin and digitoxin; all three can be extracted from the same source.
Chemical structure of digitonin
| |
| |
Names | |
---|---|
Other names
Digitin
| |
Identifiers | |
3D model (
JSmol)
|
|
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.031.129 |
EC Number |
|
KEGG | |
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
Properties | |
C56H92O29 | |
Molar mass | 1229.323 g·mol−1 |
Appearance | White to off-white powder |
Melting point | 244.0–248.5 °C (471.2–479.3 °F; 517.1–521.6 K) [1] |
Chiral rotation ([α]D)
|
-40° (589.3 nm; 20 °C) [1] |
Hazards | |
Lethal dose or concentration (LD, LC): | |
LD50 (
median dose)
|
23 mg/kg (rat, intravenous)
[2]
4 mg/kg (mouse, intravenous) [3] |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
Digitonin is a steroidal saponin (saraponin) obtained from the foxglove plant Digitalis purpurea. Its aglycone is digitogenin, a spirostan steroid. It has been investigated as a detergent, as it effectively water-solubilizes lipids. As such, it has several potential membrane-related applications in biochemistry, including solubilizing membrane proteins, precipitating cholesterol, and permeabilizing cell membranes. [4] [5]
Digitonin is sometimes confused with the cardiac drugs digoxin and digitoxin; all three can be extracted from the same source.