Digitonin

Digitonin
	File:Digitonin CASCC.png Chemical structure of digitonin
	File:Digitonin.png Alternate depiction using sugar abbreviations (Gal = galactose, Glc = glucose, Xyl = xylose
Names
	Other names Digitin
Identifiers
CAS Number	11024-24-1 check;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:27729;
ChEMBL	ChEMBL404811 ☒;
ChemSpider	23753 check;
ECHA InfoCard	Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value). Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value).Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
EC Number	234-255-6;
E number	Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value).
KEGG	C00765 ☒;
PubChem CID	25444;
UNII	KOO5CM684H check;
CompTox Dashboard (EPA)	{{#property:P3117}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).;
	InChI InChI=1S/C56H92O29/c1-19-7-10-56(75-17-19)20(2)31-45(85-56)37(67)32-22-6-5-21-11-26(24(61)12-55(21,4)23(22)8-9-54(31,32)3)76-50-42(72)39(69)44(30(16-60)80-50)81-53-48(47(36(66)29(15-59)79-53)83-49-40(70)33(63)25(62)18-74-49)84-52-43(73)46(35(65)28(14-58)78-52)82-51-41(71)38(68)34(64)27(13-57)77-51/h19-53,57-73H,5-18H2,1-4H3/t19-,20+,21+,22-,23+,24-,25-,26-,27-,28-,29-,30-,31+,32-,33+,34-,35+,36?,37+,38+,39-,40-,41-,42-,43-,44+,45-,46+,47+,48-,49+,50-,51+,52+,53+,54-,55+,56-/m1/s1 ☒ Key: UVYVLBIGDKGWPX-YCCXZQINSA-N ☒; InChI=1/C56H92O29/c1-19-7-10-56(75-17-19)20(2)31-45(85-56)37(67)32-22-6-5-21-11-26(24(61)12-55(21,4)23(22)8-9-54(31,32)3)76-50-42(72)39(69)44(30(16-60)80-50)81-53-48(47(36(66)29(15-59)79-53)83-49-40(70)33(63)25(62)18-74-49)84-52-43(73)46(35(65)28(14-58)78-52)82-51-41(71)38(68)34(64)27(13-57)77-51/h19-53,57-73H,5-18H2,1-4H3/ t19-,20+,21+,22-,23+,24-,25-,26-,27-,28-,29-,30-,31+,32-,33+,34-,35+,36?,37+,38+,39-,40-,41-,42-,43-,44+,45-,46+,47+,48-,49+,50-,5 1+,52+,53+,54-,55+,56-/m1/s1;
	SMILES O[C@@H]%11[C@@H](O)[C@H](O)[C@H](O[C@H]%11O[C@@H]1[C@@H](O)[C@@H](O[C@H](CO)[C@@H]1O)O[C@@H]%10[C@@H](O[C@@H]2OC[C@@H](O)[C@H](O)[C@H]2O)C(O)[C@H](O[C@H]%10O[C@@H]3[C@H](O)[C@@H](O)[C@@H](O[C@@H]3CO)O[C@H]9[C@H](O)C[C@@]8(C)[C@@H](CC[C@@H]6[C@@H]8CC[C@@]7([C@@H]5[C@@H](O[C@@]4(OC[C@@H](CC4)C)[C@H]5C)[C@@H](O)[C@@H]67)C)C9)CO)CO;
Properties
Chemical formula	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)
Chiral rotation ([α]D)	-40° (589.3 nm; 20 °C)
Hazards
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	23 mg/kg (rat, intravenous) 4 mg/kg (mouse, intravenous)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). ☒ verify (what is check☒ ?) Infobox references

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.

Commercial digitonin preparations can often contain other congeners including tigonin, gitonin, digalonin, and desglucodigitonin.^[6]

Chemical properties

Critical micelle concentration = < 0.5 mM
Average micellar weight = 70000
Aggregation number = 60

References

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v t e Glycosides (glycosidic bond)
Glycone	Fructoside Galactoside Glucoside Glucuronide Rhamnoside Riboside
Aglycone	Alcoholic glycoside Cardiac glycoside Bufadienolide Cardenolide Cyanogenic glycoside Glycosylamine Phenolic glycoside Anthraquinone glycoside Coumarin glycoside Flavonoid glycoside Saponin Steviol glycoside Thioglycoside

Names
File:Digitonin CASCC.png Chemical structure of digitonin
File:Digitonin.png Alternate depiction using sugar abbreviations (Gal = galactose, Glc = glucose, Xyl = xylose
Other names Digitin
Identifiers
CAS Number	11024-24-1^checkY
3D model (JSmol)	Interactive image
ChEBI	CHEBI:27729
ChEMBL	ChEMBL404811^☒N
ChemSpider	23753^checkY
ECHA InfoCard	Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value). Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value).Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
EC Number	234-255-6
E number	Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value).
KEGG	C00765^☒N
PubChem CID	25444
UNII	KOO5CM684H^checkY
CompTox Dashboard (EPA)	{{#property:P3117}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
InChI InChI=1S/C56H92O29/c1-19-7-10-56(75-17-19)20(2)31-45(85-56)37(67)32-22-6-5-21-11-26(24(61)12-55(21,4)23(22)8-9-54(31,32)3)76-50-42(72)39(69)44(30(16-60)80-50)81-53-48(47(36(66)29(15-59)79-53)83-49-40(70)33(63)25(62)18-74-49)84-52-43(73)46(35(65)28(14-58)78-52)82-51-41(71)38(68)34(64)27(13-57)77-51/h19-53,57-73H,5-18H2,1-4H3/t19-,20+,21+,22-,23+,24-,25-,26-,27-,28-,29-,30-,31+,32-,33+,34-,35+,36?,37+,38+,39-,40-,41-,42-,43-,44+,45-,46+,47+,48-,49+,50-,51+,52+,53+,54-,55+,56-/m1/s1^☒N Key: UVYVLBIGDKGWPX-YCCXZQINSA-N^☒N InChI=1/C56H92O29/c1-19-7-10-56(75-17-19)20(2)31-45(85-56)37(67)32-22-6-5-21-11-26(24(61)12-55(21,4)23(22)8-9-54(31,32)3)76-50-42(72)39(69)44(30(16-60)80-50)81-53-48(47(36(66)29(15-59)79-53)83-49-40(70)33(63)25(62)18-74-49)84-52-43(73)46(35(65)28(14-58)78-52)82-51-41(71)38(68)34(64)27(13-57)77-51/h19-53,57-73H,5-18H2,1-4H3/ t19-,20+,21+,22-,23+,24-,25-,26-,27-,28-,29-,30-,31+,32-,33+,34-,35+,36?,37+,38+,39-,40-,41-,42-,43-,44+,45-,46+,47+,48-,49+,50-,5 1+,52+,53+,54-,55+,56-/m1/s1
SMILES O[C@@H]%11[C@@H](O)[C@H](O)[C@H](O[C@H]%11O[C@@H]1[C@@H](O)[C@@H](O[C@H](CO)[C@@H]1O)O[C@@H]%10[C@@H](O[C@@H]2OC[C@@H](O)[C@H](O)[C@H]2O)C(O)[C@H](O[C@H]%10O[C@@H]3[C@H](O)[C@@H](O)[C@@H](O[C@@H]3CO)O[C@H]9[C@H](O)C[C@@]8(C)[C@@H](CC[C@@H]6[C@@H]8CC[C@@]7([C@@H]5[C@@H](O[C@@]4(OC[C@@H](CC4)C)[C@H]5C)[C@@H](O)[C@@H]67)C)C9)CO)CO
Properties
Chemical formula	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). ☒N verify (what is ^checkY☒N ?) Infobox references

Digitonin

Chemical properties

References

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