Digitonin

Digitonin
	; Chemical structure of digitonin
	; Alternate depiction using sugar abbreviations (Gal = galactose, Glc = glucose, Xyl = xylose
Names
	Other names Digitin
Identifiers
CAS Number	11024-24-1 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL404811 ;
ChemSpider	23753 ;
ECHA InfoCard	100.031.129
EC Number	234-255-6;
KEGG	C00765 ;
PubChem CID	25444;
UNII	KOO5CM684H ;
CompTox Dashboard (EPA)	DTXSID1025065 ;
	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).

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 and all three can be extracted from the same source.

Chemical properties

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

References

^ ^a ^b Tschesche, R.; Wulff, G. (January 1963). "Über saponine der spirostanolreihe—IX". Tetrahedron (in German). 19 (4): 621–634. doi:10.1016/S0040-4020(01)98548-5.
^ Segal, Ruth; Milo-Goldzweig, Ilana; Kaplan, Gideon; Weisenberg, Emil (April 1977). "The protective action of glycyrrhizin against saponin toxicity". Biochemical Pharmacology. 26 (7): 643–645. doi:10.1016/0006-2952(77)90039-9. PMID 856195.
^ Pitha, Josef; Szente, Lajos (February 1984). "Digitonin derivatives of low toxicity: Potential solubilizers for lipophilic compounds". Journal of Pharmaceutical Sciences. 73 (2): 240–243. doi:10.1002/jps.2600730224. PMID 6707892.
^ Geelen, Math J.H. (December 2005). "The use of digitonin-permeabilized mammalian cells for measuring enzyme activities in the course of studies on lipid metabolism". Analytical Biochemistry. 347 (1): 1–9. doi:10.1016/j.ab.2005.03.032. PMID 16291302.
^ Fiskum, Gary (April 1985). "Intracellular levels and distribution of Ca2+ in digitonin-permeabilized cells". Cell Calcium. 6 (1–2): 25–37. doi:10.1016/0143-4160(85)90032-6. PMID 4016893.

[Wulff-1] Tschesche, R.; Wulff, G. (January 1963). "Über saponine der spirostanolreihe—IX". Tetrahedron (in German). 19 (4): 621–634. doi:10.1016/S0040-4020(01)98548-5.

[2] Segal, Ruth; Milo-Goldzweig, Ilana; Kaplan, Gideon; Weisenberg, Emil (April 1977). "The protective action of glycyrrhizin against saponin toxicity". Biochemical Pharmacology. 26 (7): 643–645. doi:10.1016/0006-2952(77)90039-9. PMID 856195.

[3] Pitha, Josef; Szente, Lajos (February 1984). "Digitonin derivatives of low toxicity: Potential solubilizers for lipophilic compounds". Journal of Pharmaceutical Sciences. 73 (2): 240–243. doi:10.1002/jps.2600730224. PMID 6707892.

[4] Geelen, Math J.H. (December 2005). "The use of digitonin-permeabilized mammalian cells for measuring enzyme activities in the course of studies on lipid metabolism". Analytical Biochemistry. 347 (1): 1–9. doi:10.1016/j.ab.2005.03.032. PMID 16291302.

[5] Fiskum, Gary (April 1985). "Intracellular levels and distribution of Ca2+ in digitonin-permeabilized cells". Cell Calcium. 6 (1–2): 25–37. doi:10.1016/0143-4160(85)90032-6. PMID 4016893.

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[2]

[3]

[4]

[5]

Names
Chemical structure of digitonin
Alternate depiction using sugar abbreviations (Gal = galactose, Glc = glucose, Xyl = xylose
Other names Digitin
Identifiers
CAS Number	11024-24-1
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL404811
ChemSpider	23753
ECHA InfoCard	100.031.129
EC Number	234-255-6
KEGG	C00765
PubChem CID	25444
UNII	KOO5CM684H
CompTox Dashboard (EPA)	DTXSID1025065
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)^[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).