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D141

Sigma-Aldrich

Digitonin

Used as non-ionic detergent

Synonym(s):

Digitin

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About This Item

Empirical Formula (Hill Notation):
C56H92O29
CAS Number:
11024-24-1
Molecular Weight:
1229.31
Beilstein:
78654
EC Number:
234-255-6
MDL number:
MFCD00077729
UNSPSC Code:
12161900
PubChem Substance ID:
24893429
NACRES:
NA.25

biological source

plant seeds (Digitalis purpurea)

Quality Level

200

form

powder

optical activity

[α]20/D −54°, c = 2.8 in methanol(lit.)

mol wt

micellar avg mol wt 70,000

aggregation number

60

impurities

<6.0% water

CMC

<0.5 mM (20-25°C)
<0.5 mM (20-25°C)

mp

230-240 °C (dec.) (lit.)

solubility

H2O: ~5 % (w/v) (solubilized by heating to 95 °C - 98 °C and then cooling to room temp.)

SMILES string

C[C@@]12[C@]([C@@H]3C)([H])[C@](O[C@]34CC[C@@H](C)CO4)([H])[C@@H](O)[C@@]1([H])[C@@](CC[C@]5([H])[C@@]6(C[C@@H](O)[C@H](O[C@]([C@@H]([C@@H](O)[C@H]7O[C@@](O[C@H](CO)[C@@H](O)[C@@H]8O[C@@](OC[C@@H](O)[C@@H]9O)([H])[C@@H]9O)([H])[C@@H]8O[C@@](O[C@H](CO)[C@H

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

InChI key

UVYVLBIGDKGWPX-KUAJCENISA-N

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General description

Digitonin, a steroidal saponin extracted from the purple foxglove plant (Digitalis purpurea), stands as a versatile non-ionic detergent crucial for cell biology and biochemical research. Its unique attributes position it as a valuable asset in the exploration of cellular membranes, membrane proteins, and intracellular components. Digitonin′s key properties and applications include its ability to solubilize membrane-bound proteins effectively while preserving their native conformation, making it an ideal tool for studying membrane protein interactions and activities.

Moreover, Digitonin selectively permeabilizes the cholesterol-rich plasma membrane, leaving organelle membranes intact. This feature facilitates the extraction and purification of specific organelles, contributing to the study of their functions and roles in cellular processes. The detergent′s capability to permeabilize diverse cell types allows the study of intracellular components and processes by introducing molecules, antibodies, or enzymes into cells. Additionally, Digitonin finds application in immunocytochemistry experiments, enabling the labeling and detection of intracellular proteins and structures.

Application

Digitonin has been used along with permeabilization buffer for cyclic guanosine monophosphate-adenosine monophosphate (cyclic GMP-AMP) stimulation in cells.
Digitonin has been used in a study to assess a procedure for isolating mitochondria from ascites tumor cells. It has also been used in a study to investigate its effect on the cytotoxicity of plant secondary metabolites in cancer cells.

Biochem/physiol Actions

Digitonin plays a key role in permeabilizing cell membranes. It is capable of lysing eukaryotic cells but not bacterial membranes. It is also used to solubilize membrane components. It helps to create pores by interacting specifically with cholesterol in the membrane. It is preferred in biotechnology due to its mild detergency. This membrane-active compound act with doxorubicin against multi-drug resistant cancer cells.

Features and Benefits

Highly versatile compound for your cell biology and biochemical research

Quality

Preparation is free of water-insoluble constituents.

Other Notes

For additional information on our range of Biochemicals, please complete this form.

comparable product

Product No.
Description
Pricing

D5628

Digitonin, ~50% (TLC)

Pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

Signal Word

Danger

Hazard Statements

H301,H373

Precautionary Statements

P301 + P310 + P330 - P314

Hazard Classifications

Acute Tox. 3 Oral - STOT RE 2

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  3. What is the solubility of Product D141, Digitonin?

    The solubility of D141 is tested by heating a 5% solution in water to 95-98°C and then cooling the solution to room temperature. After cooling, the solution should remain practically clear for at least 24 hours. The product can also be dissolved at 100mg/4mL of warm ethanol.

  4. What is the solution stability of Product D141, Digitonin?

    We recommend making solutions fresh for use.

  5. How pure is Product D141, Digitonin?

    The purity of this product is evaluated by Thin Layer Chromatography. The actual results are lot specific and will be reported on the Certificate of Analysis of each lot.

  6. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

  7. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

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    Ask a Scientist here.

R W Moreadith et al.
Analytical biochemistry, 137(2), 360-367 (1984-03-01)
A new, improved procedure for isolating mitochondria from ascites tumor cells is described. The unique feature of this technique is the use of digitonin to make the cells susceptible to disruption by Teflon pestle/glass vessel homogenization. The yield and respiratory
Wattamon Srisakuldee et al.
Cardiovascular research, 103(1), 72-80 (2014-03-22)
Fibroblast growth factor 2 (FGF-2) protects the heart from ischaemia- and reperfusion-induced cell death by a mechanism linked to protein kinase C (PKC)ε-mediated connexin 43 (Cx43) phosphorylation. Cx43 localizes predominantly to gap junctions, but has also been detected at subsarcolemmal
Xianying A Cui et al.
Journal of visualized experiments : JoVE, (70)(70), e50066-e50066 (2012-12-29)
In eukaryotes, most of the messenger RNAs (mRNAs) that encode secreted and membrane proteins are localized to the surface of the endoplasmic reticulum (ER). However, the visualization of these mRNAs can be challenging. This is especially true when only a
Safaa Yehia Eid et al.
Phytomedicine : international journal of phytotherapy and phytopharmacology, 19(14), 1307-1314 (2012-10-16)
In phytotherapy, extracts from medicinal plants are employed which contain mixtures of secondary metabolites. Their modes of action are complex because the secondary metabolites can react with single or multiple targets. The components in a mixture can exert additive or
Xianying A Cui et al.
PLoS biology, 10(5), e1001336-e1001336 (2012-06-09)
In metazoans, the majority of mRNAs coding for secreted and membrane-bound proteins are translated on the surface of the endoplasmic reticulum (ER). Although the targeting of these transcripts to the surface of the ER can be mediated by the translation
View All Related Papers

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