Sodium Deoxycholate

Synonyme: Deoxycholic acid sodium salt, Sodium 3α,12α-dihydroxy-5β-cholan-24-oate, 7-Deoxycholic acid sodium salt, Sodium deoxycholate, Choleic acid sodium salt

Sodium deoxycholate is a bile salt that occurs naturally in the human body as a secondary bile acid, formed by bacterial 7α-dehydroxylation of cholic acid in the colon. Its molecular architecture features a rigid steroid nucleus with hydroxyl groups at the 3α and 12α positions, and a carboxylate group at the end of a short side chain. This amphipathic structure underpins its distinctive physicochemical behavior: the hydrophobic β-face of the steroid nucleus contrasts with the hydrophilic α-face and the charged side chain, giving the molecule strong surfactant properties. As a sodium salt, it is highly water-soluble and readily forms micelles above its critical micelle concentration (CMC) of approximately 2–6 mM, depending on temperature and ionic strength.

Industrially, sodium deoxycholate is produced by saponification of deoxycholic acid, which is typically obtained from animal bile (bovine or ovine) or through semi-synthetic routes from cholic acid. The resulting product is purified to meet pharmacopeial standards (e.g., USP/NF, EP) and is available in several grades, including reagent grade, cell culture tested, and injectable grade. Each grade differs in residual solvents, heavy metals, and endotoxin levels, making the selection critical for specific applications. For example, injectable grade must be sterile-filtered and pyrogen-free, while cell culture grade requires low endotoxin and no detectable cytotoxicity.

In the life sciences, sodium deoxycholate is indispensable as a mild detergent for membrane protein extraction and cell lysis, where it solubilizes proteins while preserving native conformation. It is also a key component in selective microbiological media, such as MacConkey agar, where it inhibits Gram-positive bacteria. In the pharmaceutical arena, it serves as a solubilizing agent for poorly water-soluble drugs and as an active ingredient in injectable formulations for localized fat reduction. Beyond these, it finds use in proteomics, lipid research, and as a reference standard in analytical chemistry. The growing demand for high-purity bile salts in biopharmaceutical manufacturing has positioned sodium deoxycholate as a critical raw material, with stringent quality requirements driving innovation in purification technologies.

Chemical Structure & Properties

The steroid nucleus of sodium deoxycholate is a cyclopentanoperhydrophenanthrene ring system with a cis A/B ring junction, characteristic of the 5β series. The two hydroxyl groups at C-3 and C-12 are both α-oriented, while the C-17 side chain terminates in a carboxylate anion. This arrangement creates a planar hydrophobic surface on the β-face and a polar surface on the α-face, leading to the formation of micelles in aqueous solution. The sodium salt is freely soluble in water (up to ~330 mg/mL at 20°C) and in ethanol, but practically insoluble in acetone, chloroform, and ether. Its aqueous solutions are mildly alkaline (pH ~7.5–9.0 for a 1% solution) and exhibit a bitter taste. The compound is stable under normal storage conditions but should be protected from moisture and light to prevent degradation. Its surface-active properties are influenced by temperature, pH, and the presence of electrolytes; the CMC decreases with increasing ionic strength.

Mechanism of Action

• Membrane solubilization: Sodium deoxycholate integrates into lipid bilayers, disrupting hydrophobic interactions and solubilizing membrane proteins while maintaining their antigenicity and enzymatic activity.
• Micelle formation: Above the CMC, it aggregates to form mixed micelles that encapsulate hydrophobic compounds, enhancing the aqueous solubility of drugs and lipids.
• Antimicrobial activity: It disrupts bacterial cell membranes, particularly effective against Gram-positive organisms, and is used in selective media to inhibit unwanted flora.
• Lipolysis induction: When injected subcutaneously, it causes nonspecific lysis of adipocytes, leading to localized fat reduction and subsequent fibrosis.
• Protein stabilization: In bioprocessing, it aids in the refolding and stabilization of recombinant proteins by mimicking the lipid environment.

Quality Specifications

Supply & Documentation

• Capacity: 50 metric tons per year
• Lieferzeit: 3–5 Werktage (Lagerware)
• Dokumentation: COA, MSDS, TDS, and additional testing upon request (e.g., residual solvents, elemental impurities)
• Verpackung: 25 kg fiber drums with double polyethylene liners; custom packaging available for small quantities

Angebotsanfrage

• LyvBio GmbH. — E-Mail: info@lyvbio.com