Taurocholic acid

• CAS: 81-24-3
• Catalog Number: ACM81243-2
• Category: Main Products
• Molecular Weight: 515.706
• Molecular Formula: C26H45NO7S
• Synonyms: 2-[[(3α,5β,7α,12α)-3,7,12-Trihydroxy-24-oxocholan-24-yl]amino]ethanesulfonic Acid;‡3α,7α,12α-Trihydroxy-5β-cholanic Acid-24-taurine; Cholaic Acid; Cholic Acid Taurine Conjugate
• Melting Point: >112 °C
• Appearance: White to off-white solid
• Storage: Solid
• Physical State: Freezer

Case Study

Taurocholic Acid as a Modulator of Intestinal Barrier Permeability

Liu H, et al. Food Chem Toxicol, 2022, 165, 113136.

Taurocholic acid (TCA), a primary 12α-hydroxylated bile acid, plays a significant role in modulating intestinal permeability, particularly within the ileum. Recent studies reveal that a high-fat diet leads to elevated secretion of 12α-hydroxylated bile acids, including TCA, which contributes to increased gut permeability in the distal small intestine of rats. Supplementing with cholic acid (CA) elevates 12αOH bile acid concentrations, thereby disrupting the gut barrier, as evidenced by enhanced phosphorylation of myosin light chain 2 (MLC2) and altered expression of claudins in the ileal epithelia.
In ex vivo experiments, TCA uniquely increased ileal permeability, an effect modulated by inhibiting Rho kinase, indicating a pathway-specific interaction. This increased leakiness was not observed in the jejunum, emphasizing TCA's ileum-specific effects. Furthermore, TCA presence in portal blood correlated with the permeability changes, solidifying its role as a critical factor in modulating gut integrity.
Significantly, the impact of TCA on gut permeability was independent of secondary bile acids. Antibiotic treatment with vancomycin, which suppresses secondary bile acid synthesis, did not alter TCA-induced leakiness, suggesting that primary 12αOH bile acids alone are sufficient to induce this response. Additionally, the CA diet notably altered gene expressions related to barrier function specifically in the ileum, implicating TCA as a mediator of these transcriptional changes. This study underscores the potential of TCA as a key modulator of gut barrier integrity, with implications for understanding gut permeability disorders and developing targeted therapeutic interventions.

Taurocholic Acid in the Synthesis of HDTA Nanoparticles for Targeted Drug Delivery

Khatun Z, et al. Journal of Controlled Release, 2014, 177, 64-73.

Taurocholic acid (TCA), a bile acid derivative, plays a crucial role in the synthesis of HDTA nanoparticles, a system engineered for precision drug delivery applications, particularly in oncological contexts. The development of HDTA nanoparticles centers on a strategic conjugation of TCA with heparin and the chemotherapeutic agent docetaxel (DTX). This unique design aims to leverage TCA's molecular affinity for hepatic receptors and its potential to enhance solubility and targeted cellular uptake of the therapeutic agents.
To activate TCA, sodium taurocholate is dissolved in DMF at low temperatures and reacted with triethylamine (TEA) and 4-nitrophenyl chloroformate (4-NPC). The resulting solution undergoes purification, solvent extraction, and is dried to produce TCA-NPC powder. This compound is further functionalized by introducing 4-methyl-morpholine (4-MMP) and ethylenediamine (EDA), facilitating TCA's coupling with heparin, which is achieved by activating the heparin using EDC and NHS reagents under controlled pH conditions.
The TCA-heparin conjugate (HTA) thus formed is dialyzed to remove residual reactants, ensuring high purity for subsequent steps. In the final assembly of HDTA nanoparticles, DTX is introduced through a gradual addition to HTA in DMSO, followed by sequential activation with TEA and 4-NPC, ensuring robust linkage stability. Methanol and hexane washes remove unbound compounds, and the HDTA nanoparticles are dialyzed and freeze-dried for final purification and solid-state formulation.

Custom Q&A

What is the molecular formula of taurocholic acid?

The molecular formula of taurocholic acid is C26H45NO7S.

What is the molecular weight of taurocholic acid?

The molecular weight of taurocholic acid is 515.7 g/mol.

What are the synonyms of taurocholic acid?

The synonyms of taurocholic acid are TAUROCHOLIC ACID, Taurocholate, 81-24-3, Cholyltaurine, and Cholaic acid.

What is the role of taurocholic acid in mammals?

Taurocholic acid usually occurs as the sodium salt of bile in mammals and has a role as a human metabolite.

What is the chemical structure of taurocholic acid?

The chemical structure of taurocholic acid can be viewed at the following link: https://pubchem.ncbi.nlm.nih.gov/image/img3d.cgi?&cid=6675&t=s

What is the IUPAC name of taurocholic acid?

The IUPAC name of taurocholic acid is 2-[[(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-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]ethanesulfonic acid.

What is the InChI key of taurocholic acid?

The InChI key of taurocholic acid is WBWWGRHZICKQGZ-HZAMXZRMSA-N.

What is the CAS number of taurocholic acid?

The CAS number of taurocholic acid is 81-24-3.

What is the chief ingredient of the bile of carnivorous animals?

The chief ingredient of the bile of carnivorous animals is the sodium salt of taurocholic acid.

What is the use of taurocholic acid?

Taurocholic acid is used as a cholagogue and cholerectic.