Chemical Properties
Sodium deoxycholate is white to cream crystalline powder
Uses
Sodium deoxycholate is an ionic detergent for the solubilization of membrane-bound proteins.
Uses
Sodium deoxycholate is used as a component in cell lysis buffers.
Definition
ChEBI: Sodium deoxycholate is a bile acid salt. It contains a deoxycholate.
General Description
Sodium deoxycholate is a bile salt and an ionic detergent. Bile salts work along with lipids/fats/cholesterol and form mixed micelles in the intestine. These micelles help in fat digestion and absorption through the intestinal wall.
Biological Activity
Sodium deoxycholate (SDC) is an anionic detergent which has been used both to destroy infectious viruses and to fractionate viral components. Sodium deoxycholate begins to bind to the virus at less than 0.1 mM free equilibrium concentration. It causes lysis of the viral membrane at 0.9 +/- 0.1 mM free equilibrium concentration when 2.2 +/- 0.2 - 103 mol of sodium deoxycholate are bound per mol of the virus. The liberation of proteins from the membrane begins at 1.5 +/- 0.1 mM sodium deoxycholate, and the proteins released are virtually free from phospholipids above 2.0 mM sodium deoxycholate. The overall mechanism of sodium deoxycholate solubilization of the viral membrane resembles that of Triton X-100 and sodium dodecyl sulphate, except that with sodium deoxycholate, the various stages of membrane disruption occur at about 10-fold higher equilibrium free detergent concentrations. At sodium deoxycholate concentrations higher than 2.3 mM, the viral spike glycoproteins can be separated by sucrose gradient centrifugation or gel filtration into constituent polypeptides E1, E2 and E3[1-2].
Biochem/physiol Actions
Solubilizes fats for absorption in the intestines.
Synthesis
Sodium deoxycholate can be prepared by that: 100g of industrial deoxycholic acid (purity 97%) in a 1000mL flask with mechanical stirring, reflux condenser and thermometer, 600mL of absolute ethanol, heating to 60 ℃ with stirring, adding 2g of activated carbon, and stirring for 2h, wherein the slightly turbid solution is obtained. Hot filtered and passed through a 0.45 μm microfiltration membrane. Slowly adding newly prepared sodium hydroxide ethanol solution (the mass concentration of sodium hydroxide is 6%) into the filtrate while stirring until the pH value of the reaction solution is 7.5, continuously stirring for 2h, concentrating under reduced pressure until the concentration of sodium deoxycholate is 25 wt%, cooling to room temperature, and continuously pulping for 5 h. Filtering, leaching the filter cake with absolute ethyl alcohol, drying at 85 ℃ to obtain 97.1g of white sodium deoxycholate powder, wherein the yield is 94.8%, the purity is 100%, the optical rotation is + 44.5%, the sodium content is 6.0%, the heavy metal content is less than or equal to 0.002%, and the arsenic content is less than or equal to 0.0002%.
Purification Methods
Recrystallise it from EtOH and dry it in an oven at 100o. The solution is freed from soluble components by repeated extraction with acid-washed charcoal. [Beilstein 10 IV 1608.]
References
[1] A Helenius. “Solubilization of the Semliki Forest virus membrane with sodium deoxycholate.” Biochimica et biophysica acta 436 2 (1976): 319–34.
[2] A E Auletta, M L Marlowe. “Effect of sodium deoxycholate on rubella virus.” Applied microbiology 16 10 (1968): 1624.
