Glycocholic acid hydrate

• CAS: 1192657-83-2
• Catalog Number: ACM1192657832
• Category: Main Products
• Molecular Weight: 465.62 (anhydrous basis)
• Molecular Formula: C26H43NO6·xH₂O
• Synonyms: 3α,7α,12α-Trihydroxy-5β-cholan-24-oic acid N-(carboxymethyl)amide
• IUPAC Name: 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]acetic acid;hydrate
• Canonical SMILES: CC(CCC(=O)NCC(=O)O)C1CCC2C1(C(CC3C2C(CC4C3(CCC(C4)O)C)O)O)C.O
• InChI: InChI=1S/C26H43NO6.H₂O/c1-14(4-7-22(31)27-13-23(32)33)17-5-6-18-24-19(12-21(30)26(17,18)3)25(2)9-8-16(28)10-15(25)11-20(24)29;/h14-21,24,28-30H,4-13H2,1-3H3,(H,27,31)(H,32,33);1H2/t14-,15+,16-,17-,18+,19+,20-,21+,24+,25+,26-;/m1./s1
• InChI Key: WDKPRHOCWKLQPK-ZUHYDKSRSA-N
• Appearance: Powder
• Complexity: 759
• Exact Mass: 483.31960277
• Formal Charge: 0
• Heavy Atom Count: 34
• Hydrogen Bond Acceptor Count: 7
• Hydrogen Bond Donor Count: 6
• Isomeric SMILES: C[C@H](CCC(=O)NCC(=O)O)[C@H]1CC[C@@H]2[C@@]1([C@H](C[C@H]3[C@H]2[C@@H](C[C@H]4[C@@]3(CC[C@H](C4)O)C)O)O)C.O
• MDL Number: MFCD06408004
• Monoisotopic Mass: 483.31960277
• Rotatable Bond Count: 6
• Shipping: Ambient temperature
• Storage Conditions: Room temperature
• Topological Polar Surface Area: 128 Ų

Case Study

Deoxycholic Acid and Glycocholic Acid Functionalized Nanoparticles for Oral Delivery of Exenatide

Han, Ying, et al. Biomaterials, 2021, 275, 120944.

A dual cholic acid-functionalized nanoparticle delivery system was constructed using a combination of hydrophobic deoxycholic acid (DCA) and hydrophilic glycocholic acid (GCA). The nanoparticles NPs are functionalized materials based on LMWP-DCA (L-D) and PSA-b-PEG-GCA (PPG). The results show that the obtained NPs exhibit enhanced uptake and transport of exenatide.
Synthesis of PPG and nanoparticles
· Synthesis of PPG: GCA was dissolved in a DMF solution, followed by the addition of N-hydroxysuccinimide (NHS) and 1-ethyl-(3-dimethylamino propyl) carbonyl diimide hydrochloride (EDC) at room temperature (rt) for 2 hours. Subsequently, DIEA and NH2-PEG2000-tBOC were introduced and allowed to react for 24 hours. The obtained GCA-PEG-tBOC was then dissolved in DCM, with TFA being slowly added. DCM and TFA were then removed through rotary evaporation. GCA-PEG-NH2 was dissolved in water, whereas PSA was dissolved in 10 mL MES buffer, following the addition of NHS and EDC to activate carboxyl at rt for 20 min. Then, sodium hydroxide (NaOH) was added to adjust pH to 8 following the addition of GCA-PEG-NH2 and reacted for 24 h.
· Nanoparticle Preparation: DCA-functionalized nanocomplexes (DNCs) were obtained by assembling Ex in the presence of Zn2+ with L-D in an aqueous solution and stirring magnetically at 4°C overnight. Subsequently, PPG polymer was dissolved in methanol, evaporated under reduced pressure, and combined with the DNCs solution to yield GCA-functionalized nanoparticles (GNPs).

Use of Glycocholic Acid Hydrate in Oral Vitamin K Formulations

Sun, Feilong, et al. Pharmaceutical research, 2016, 33, 2168-2179.

To develop stable vitamin K micellar formulations for oral administration, mixed micelles composed of EPC, DSPE-PEG 2000, and glycocholic acid were prepared by a thin film hydration method. The results showed that the mixed micelles exhibited good cytocompatibility at glycocholic acid concentrations ranging from 0.12 to 1.20 mM.
Preparation of Vitamin K Loaded Micelles
· In a chloroform solution, 1 g of Vitamin K was mixed with 10 ml of chloroform. Then, 0.2 ml of this Vitamin K solution was combined with 3.8 ml of chloroform containing varying amounts of lipids (EPC and DSPE-PEG 2000). The mixture was evaporated under vacuum at 60 °C for 20 minutes to create a film.
· Separately, glycocholic acid hydrate (110 mg, 0.24 mmol) was dissolved in 8 ml of 0.067 M phosphate buffer at 60 °C and added to hydrate the film made of EPC, DSPE-PEG 2000, and Vitamin K.
· The resulting clear dispersion was stirred magnetically for a minimum of 4 hours at room temperature before being extruded three times through a syringe filter. Throughout the process, the dispersions were shielded with aluminized foil to safeguard Vitamin K from light-induced degradation.

Custom Q&A

What is the molecular formula of Glycocholic acid hydrate?

The molecular formula of Glycocholic acid hydrate is C26H45NO7.

What are the synonyms of Glycocholic acid hydrate?

The synonyms of Glycocholic acid hydrate are 1192657-83-2, Glycocholic acid (hydrate), MLS001304001.

What is the molecular weight of Glycocholic acid hydrate?

The molecular weight of Glycocholic acid hydrate is 483.6 g/mol.

What is the parent compound of Glycocholic acid hydrate?

The parent compound of Glycocholic acid hydrate is Glycocholic acid.

What are the component compounds of Glycocholic acid hydrate?

The component compounds of Glycocholic acid hydrate are Water (CID 962) and Glycocholic acid (CID 10140).

When was Glycocholic acid hydrate created?

Glycocholic acid hydrate was created on July 21, 2008.

When was Glycocholic acid hydrate last modified?

Glycocholic acid hydrate was last modified on October 21, 2023.

What is the IUPAC name of Glycocholic acid hydrate?

The IUPAC name of Glycocholic acid hydrate 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]acetic acid;hydrate.

What is the InChIKey of Glycocholic acid hydrate?

The InChIKey of Glycocholic acid hydrate is WDKPRHOCWKLQPK-ZUHYDKSRSA-N.

What is the CAS number of Glycocholic acid hydrate?

The CAS number of Glycocholic acid hydrate is 1192657-83-2.