Digitonin

Digitonin
Other names digitin
Identifiers
CAS number	11024-24-1 Y
PubChem	25444
ChemSpider	23753 Y
EC-number	234-255-6
KEGG	C00765 N
ChEMBL	CHEMBL404811 N
Jmol-3D images	Image 1
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
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
Properties
Molecular formula	C56H92O29
Molar mass	1229.31 g mol−1
Chiral rotation [α]D	-47 to -49º (10 g/100 ml 75% acetic acid at 25 °C)
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 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.

Physical, chemical and biological properties

Critical micelle concentration = < 0.5 mM
Average micellar weight = 70000
Appearance = White to off-white powder
Boiling Point/Melting Point = 230 °C to 240 °C
Aggregation number = 60
Rat-LD₅₀ = 4 mg/kg body weight (IVN), 51 mg/kg body weight (ORAL)

This article about an organic compound is a stub. You can help Wikipedia by expanding it.v · Categories: Glycosides Spiro compounds Steroids Organic compound stubs Wikimedia Foundation. 2010. Игры ⚽ Нужно сделать НИР? Danny Buderus List of countries by unemployment rate Look at other dictionaries: Digitonin — Strukturformel Allgemeines Name Digitonin Andere Namen Digiti …   Deutsch Wikipedia Digitonin — Di|gi|to|nin [Kurzw. aus nlat. Digitalis = Fingerhut (Bot.) u. ↑ Saponin] ein giftiges, nicht herzwirksames Glykosid (↑ Saponin) aus einem Spirostan Derivat (Digitogenin) u. einem Pentasaccharid aus Xylose u. je zwei Molekülen Galaktose u.… …   Universal-Lexikon digitonin — digitoninas statusas T sritis chemija apibrėžtis Steroidinis augalų glikozidas, saponinas. atitikmenys: angl. digitonin rus. дигитонин …   Chemijos terminų aiškinamasis žodynas digitonin reaction — the formation of a precipitate on treating a sterol, such as cholesterol or ergosterol, with digitonin; employed to define cholesterol esters which do not precipitate in total serum cholesterol determinations …   Medical dictionary digitonin — noun Etymology: International Scientific Vocabulary digit (from New Latin Digitalis) + saponin Date: 1875 a steroid saponin C56H92O29 occurring in the leaves and seeds of the common foxglove …   New Collegiate Dictionary digitonin — See saponin …   Dictionary of molecular biology digitonin — noun A glycoside, obtained from Digitalis purpurea, that is used as a detergent and whose aglycone is digitogenin …   Wiktionary digitonin — 1. A steroid glycoside obtained from Digitalis purpurea that has no cardiac action; used as a reagent in the determination of plasma cholesterol and steroids having a 3 hydroxyl group in beta …   Medical dictionary digitonin — dig·i·to·nin …   English syllables digitonin — ˈtōnə̇n noun ( s) Etymology: International Scientific Vocabulary digit (from New Latin Digitalis) + onin (as in saponin) : a crystalline steroid saponin C56H92O29 occurring in the leaves and seeds of purple foxglove …   Useful english dictionary 18+ © Academic, 2000-2024 Contact us: Technical Support, Advertising Dictionaries export, created on PHP, Joomla, Drupal, WordPress, MODx. Mark and share Search through all dictionaries Translate… Search Internet Share the article and excerpts Direct link … Do a right-click on the link above and select “Copy Link”