Hyodeoxycholic acid sodium salt

Catalog Number	ACM10421495-2
CAS	10421-49-5
Structure
Synonyms	Sodium 3α,6α-dihydroxy-5β-cholan-24-oate
IUPAC Name	Sodium;(4R)-4-[(3R,5R,6S,8S,9S,10R,13R,14S,17R)-3,6-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate
Molecular Weight	414.6
Molecular Formula	C24H39NaO4
Canonical SMILES	CC(CCC(=O)[O-])C1CCC2C1(CCC3C2CC(C4C3(CCC(C4)O)C)O)C.[Na+]
InChI	InChI=1S/C24H40O4.Na/c1-14(4-7-22(27)28)17-5-6-18-16-13-21(26)20-12-15(25)8-10-24(20,3)19(16)9-11-23(17,18)2;/h14-21,25-26H,4-13H2,1-3H3,(H,27,28);/q;+1/p-1/t14-,15-,16+,17-,18+,19+,20+,21+,23-,24-;/m1./s1
InChI Key	DUYSCILLIVEITB-ADQIWYCWSA-M
Purity	96%+
Complexity	612
Covalently-Bonded Unit Count	2
Defined Atom Stereocenter Count	10
Exact Mass	414.274604
Heavy Atom Count	29
Hydrogen Bond Acceptor Count	4
Hydrogen Bond Donor Count	2
Isomeric SMILES	C[C@H](CCC(=O)[O-])[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2C[C@@H]([C@H]4[C@@]3(CC[C@H](C4)O)C)O)C.[Na+]
Monoisotopic Mass	414.274604
Physical State	Powder
Rotatable Bond Count	4
Topological Polar Surface Area	80.6 Ų

Knowledge & Learning Case Study Q&A

Hyodeoxycholic Acid Sodium Salt as a Biosurfactant Used in Micellar Extraction

Peng LQ, et al. Journal of Chromatography A, 2017, 1515, 37-44.

Hyodeoxycholic acid sodium salt, a biosurfactant, has been evaluated for its efficacy in micellar extraction methods to isolate and determine active ingredients in ginger. In the present study, sodium porcine deoxycholate was used as extraction medium by ultrasonic assisted micellar extraction (UAME) technique.
The UAME process utilized a KQ ultrasonic system operating at a frequency of 40 kHz and power ranging from 50 to 200 W. Ginger samples (Rhizoma Zingiberis and Rhizoma Zingiberis Preparata) were ground into powder and sieved through a 100 mesh sieve.
Sample Preparation: 0.25 g of ginger powder was weighed and placed into a 50 mL Erlenmeyer flask.
Extraction: 20 mL of a surfactant aqueous solution of hyodeoxycholic acid sodium salt at a specified concentration was added.
Sonication: The mixture was sonicated for a designated time.
Post-extraction Processing: The supernatant was centrifuged at 13,000 rpm for 5 minutes and filtered through a 0.22 μm nylon Millipore membrane filter.
Analysis: The processed extract was subjected to UHPLC analysis to determine the active compounds extracted from the ginger samples.
Results and Discussion
UAME method effectively utilized hyodeoxycholic acid sodium salt as a biosurfactant to extract active compounds from ginger. Hyodeoxycholic acid sodium salt has proven to be an effective biosurfactant for micellar extraction of active ingredients in ginger using both UAME techniques.

Micelle Formation Studies of Sodium Hyodeoxycholate (NaHDC)

Matsuoka K, et al. Chemistry and Physics of Lipids, 2013, 172-173.

Sodium hyodeoxycholate (NaHDC) as a biosurfactant is characterised by an amphiphilic structure of the molecule.NaHDC can form small micelles greater than 5 mM in aqueous solution.
Micelle Formation and Critical Micelle Concentration (CMC)
The formation of micelles by NaHDC was investigated at 308.2 K using a pyrene fluorescence probe to determine the CMC at varying NaCl concentrations. The analysis revealed a two-step aggregation process:
Initial Micelle Formation: The first step involves the formation of small micelles at a concentration of 5 mM.
Stable Aggregate Formation: The second step results in the formation of stable aggregates at 14 mM in an aqueous solution.
Aggregation Behavior: The aggregation number of NaHDC, studied through a stepwise association model, increased from 4 to 7 with rising concentration. This growth in aggregation was confirmed by static light scattering methods, which measured an average aggregation number of 6.7. Despite the relatively small size of these micelles, they fall within the general range of aggregation numbers for human bile salts.
Counterion Binding: The degree of counterion binding to NaHDC micelles was determined using a sodium ion-selective electrode, revealing a binding value of approximately 0.5. This binding degree is notably high among typical bile salts, indicating a significant interaction between the sodium ions and NaHDC micelles.
Solubilization Capacity: The solubilization capacity of NaHDC micelles was assessed using cholesterol as the solubilizate. It was found that NaHDC micelles have a limited capacity to solubilize cholesterol compared to typical human bile salts. The maximum solubilization capacity of NaHDC was equivalent only to that of sodium ursodeoxycholate, highlighting its relatively lower efficacy in solubilizing cholesterol.
Conclusion: NaHDC exhibits unique micellization and aggregation properties distinct from typical human bile salts. Its high degree of counterion binding and limited cholesterol solubilization capacity suggest specialized applications in the absorption and solubilization of sparingly soluble materials within the intestinal tract. Further research into its structural characteristics and interaction with other compounds could unlock new insights into its potential applications in pharmaceuticals and other industries.

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