:Digitonin

{{Chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 312108100

| Name = Digitonin

| ImageFile = Digitonin CASCC.png

| ImageSize = 280px

| ImageCaption = Chemical structure of digitonin

| ImageFile2 = Digitonin.png

| ImageSize2 = 280px

| ImageCaption2 = Alternate depiction using sugar abbreviations (Gal = galactose, Glc = glucose, Xyl = xylose

| IUPACName =

| OtherNames = Digitin

|Section1={{Chembox Identifiers

| 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

| CASNo = 11024-24-1

| CASNo_Ref = {{cascite|correct|CAS}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = KOO5CM684H

| EC_number = 234-255-6

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 23753

| ChEBI = 27729

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 404811

| PubChem = 25444

| KEGG_Ref = {{keggcite|changed|kegg}}

| KEGG = C00765

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = UVYVLBIGDKGWPX-YCCXZQINSA-N

| 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

}}

|Section2={{Chembox Properties

| C=56 | H=92 | O=29

| MeltingPtC = 244.0-248.5

| MeltingPt_ref = {{cite journal|last1=Tschesche|first1=R.|last2=Wulff|first2=G.|title=Über saponine der spirostanolreihe—IX|journal=Tetrahedron|date=January 1963|volume=19|issue=4|pages=621–634|doi=10.1016/S0040-4020(01)98548-5|language=German}}

| Appearance = White to off-white powder

| SpecRotation = -40° (589.3 nm; 20 °C)

}}

|Section7={{Chembox Hazards

| LD50 = 23 mg/kg (rat, intravenous){{cite journal|last1=Segal|first1=Ruth|last2=Milo-Goldzweig|first2=Ilana|last3=Kaplan|first3=Gideon|last4=Weisenberg|first4=Emil|title=The protective action of glycyrrhizin against saponin toxicity|journal=Biochemical Pharmacology|date=April 1977|volume=26|issue=7|pages=643–645|doi=10.1016/0006-2952(77)90039-9|pmid=856195}}

4 mg/kg (mouse, intravenous){{cite journal|last1=Pitha|first1=Josef|last2=Szente|first2=Lajos|title=Digitonin derivatives of low toxicity: Potential solubilizers for lipophilic compounds|journal=Journal of Pharmaceutical Sciences|date=February 1984|volume=73|issue=2|pages=240–243|doi=10.1002/jps.2600730224|pmid=6707892}}

}}

}}

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.{{cite journal|last1=Geelen|first1=Math J.H.|title=The use of digitonin-permeabilized mammalian cells for measuring enzyme activities in the course of studies on lipid metabolism|journal=Analytical Biochemistry|date=December 2005|volume=347|issue=1|pages=1–9|doi=10.1016/j.ab.2005.03.032|pmid=16291302}}{{cite journal|last1=Fiskum|first1=Gary|title=Intracellular levels and distribution of Ca2+ in digitonin-permeabilized cells|journal=Cell Calcium|date=April 1985|volume=6|issue=1–2|pages=25–37|doi=10.1016/0143-4160(85)90032-6|pmid=4016893}}

Digitonin is sometimes confused with the cardiac drugs digoxin and digitoxin; all three can be extracted from the same source.