Taurochenodeoxycholic acid sodium, the sodium salt of Taurochenodeoxycholic acid, is a naturally occuring bile salt produced in the liver of animals/humans used as a detergent for the solubilization of lipids and membrane-bound proteins. Additionally, it has the ability to solubilize fats in the small intestine. Taurochenodeoxycholic acid sodium can cause apoptosis and has anti-inflammatory and immunomodulatory properties.
Physicochemical Properties
| Molecular Formula | C26H44NNAO6S |
| Molecular Weight | 521.68 |
| Exact Mass | 521.278 |
| CAS # | 6009-98-9 |
| Related CAS # | Taurochenodeoxycholic acid;516-35-8;Taurochenodeoxycholic acid-d9 sodium;2483832-00-2;Taurochenodeoxycholic acid-d5 sodium;Taurochenodeoxycholic acid-d4-1 sodium;Taurochenodeoxycholic acid-d4 sodium;2410279-85-3 |
| PubChem CID | 387316 |
| Appearance | Off-white to light yellow solid |
| Density | 1.164 g/mL at 25 °C(lit.) |
| Boiling Point | 215 °C(lit.) |
| Flash Point | 195 °F |
| Index of Refraction | n20/D 1.558(lit.) |
| LogP | 4.526 |
| Hydrogen Bond Donor Count | 4 |
| Hydrogen Bond Acceptor Count | 6 |
| Rotatable Bond Count | 7 |
| Heavy Atom Count | 34 |
| Complexity | 858 |
| Defined Atom Stereocenter Count | 10 |
| SMILES | C[C@H](CCC(=NCCS(=O)(=O)O)[O-])[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@]12C)[C@@]4(C)CC[C@H](C[C@H]4C[C@H]3O)O.[Na+] |
| InChi Key | IYPNVUSIMGAJFC-HLEJRKHJSA-M |
| InChi Code | InChI=1S/C26H45NO6S.Na/c1-16(4-7-23(30)27-12-13-34(31,32)33)19-5-6-20-24-21(9-11-26(19,20)3)25(2)10-8-18(28)14-17(25)15-22(24)29;/h16-22,24,28-29H,4-15H2,1-3H3,(H,27,30)(H,31,32,33);/q;+1/p-1/t16-,17+,18-,19-,20+,21+,22-,24+,25+,26-;/m1./s1 |
| Chemical Name | sodium;2-[[(4R)-4-[(3R,5S,7R,8R,9S,10S,13R,14S,17R)-3,7-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]pentanoyl]amino]ethanesulfonate |
| Synonyms | Taurochenodeoxycholic acid sodium salt |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| Targets | Microbial Metabolite; Human Endogenous Metabolite |
| ln Vitro | Taurochenodeoxycholic acid (12-Deoxycholyltaurine) sodium significantly increases the apoptosis rate of NR8383 cells in a concentration-dependent manner. Taurochenodeoxycholic acid sodium, meanwhile, significantly boosts PKC mRNA levels and activities and raises JNK, caspase-3, and caspase-8 mRNA expression levels and activities[1]. |
| ln Vivo | Taurochenodeoxycholic acid (12-Deoxycholyltaurine; TCDCA; 0.05, 0.1g/kg) sodium lowers the pulmonary coefficient in model mice and lessens the pathological damage to their lungs. It can also lower the expression levels of TNF-α and TIMP-2 in pulmonary tissues in pulmonary fibrosis mice, but it has no appreciable effects on MMP2[2]. Taurochenodeoxycholic acid sodium prevents indomethacin-induced increases in the biliary contents of secondary bile acids and hydrophobicity index and significantly normalizes the clinical inflammatory parameters. It also tends to lessen intestinal inflammation[3]. Taurochenodeoxycholic acid sodium significantly reduces polyarthritis index and paw swelling in AA rats, increases thymus and spleen loss body weight, and corrects radiologic changes. All TCDCA-treated rats have significantly decreased levels of serum and synovium tissue TNF-α, IL-1β, and IL-6 mRNA expression and overproduction[4]. |
| Cell Assay | Our former studies have suggested that taurochenodeoxycholic acid (TCDCA) as a signaling molecule shows obvious anti-inflammatory and immune regulation properties. In this research, we tentatively explored the potential effects and the possible mechanism that involve in the apoptotic process in NR8383 cells induced by TCDCA. Using flow cytometry analysis, we evaluated the apoptosis rate. Gene expression levels were determined by qPCR. The expressions of protein kinase C (PKC), Jun N-terminal kinase (JNK) and their phosphorylation were measured by Western Blot. We observed the activities of caspase-3 and caspase-8 with Caspase-Glo® regent. The results demonstrated that TCDCA dramatically improved the apoptosis rate of NR8383 cells in a concentration-dependent manner. In the meantime, PKC mRNA levels and activities were significantly augmented by TCDCA treatments. In addition, JNK, caspase-3 and caspase-8 mRNA expression levels and activities were increased by TCDCA, while they were markedly decreased by specific inhibitors. We conclude that TCDCA contributes to the apoptosis through the activation of the caspase cascade in NR8383 cells, and the PKC/JNK signaling pathway may be involved in this process. These results indicate that TCDCA may be a latent effective pharmaceutical product for apoptosis-related diseases [1]. |
| References |
[1]. Taurochenodeoxycholic acid induces NR8383 cells apoptosis via PKC/JNK-dependent pathway. Eur J Pharmacol. 2016 Sep 5;786:109-15. [2]. The effects of taurochenodeoxycholic acid in preventing pulmonary fibrosis in mice. Pak J Pharm Sci. 2013 Jul;26(4):761-5. [3]. Taurochenodeoxycholic acid ameliorates and ursodeoxycholic acid exacerbates small intestinal inflammation. Am J Physiol. 1997 May;272(5 Pt 1):G1249-57. [4]. Effects of taurochenodeoxycholic acid on adjuvant arthritis in rats. Int Immunopharmacol. 2011 Dec;11(12):2150-8. |
| Additional Infomation |
Taurochenodeoxycholic acid is a bile acid taurine conjugate of chenodeoxycholic acid. It has a role as a mouse metabolite and a human metabolite. It is functionally related to a chenodeoxycholic acid. It is a conjugate acid of a taurochenodeoxycholate. Taurochenodeoxycholic acid is an experimental drug that is normally produced in the liver. Its physiologic function is to emulsify lipids such as cholesterol in the bile. As a medication, taurochenodeoxycholic acid reduces cholesterol formation in the liver, and is likely used as a choleretic to increase the volume of bile secretion from the liver and as a cholagogue to increase bile discharge into the duodenum. It is also being investigated for its role in inflammation and cancer therapy. Taurochenodeoxycholic acid has been reported in Homo sapiens and Trypanosoma brucei with data available. A bile salt formed in the liver by conjugation of chenodeoxycholate with taurine, usually as the sodium salt. It acts as detergent to solubilize fats in the small intestine and is itself absorbed. It is used as a cholagogue and choleretic. Drug Indication Taurochenodeoxycholic acid is likely indicated as a choleretic and cholagogue. It is also being investigated for its role in inflammation and cancer therapy. Mechanism of Action Chenodeoxycholic acid is a primary bile acid in the liver that combines with taurine to form the bile acid taurochenodeoxycholic acid. In the bile, taurochenodeoxycholic acid is either a sodium (most) or potassium salt. Taurochenodeoxycholic acid is normally produced in the liver, and its physiologic function as a bile salt is to emulsify lipids such as cholesterol in the bile. As a medication, taurochenodeoxycholic acid reduces cholesterol formation in the liver, and is likely used as a choleretic to increase the volume of bile secretion from the liver and as a cholagogue to increase bile discharge into the duodenum. The mechanism of action of taurochenodeoxycholic acid in inflammation and cancer has yet to be determined. |
Solubility Data
| Solubility (In Vitro) | DMSO: ~100 mg/mL (~191.7 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (3.99 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.08 mg/mL (3.99 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.08 mg/mL (3.99 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.9169 mL | 9.5844 mL | 19.1688 mL | |
| 5 mM | 0.3834 mL | 1.9169 mL | 3.8338 mL | |
| 10 mM | 0.1917 mL | 0.9584 mL | 1.9169 mL |