Cholic Acid

Catalog Number	ACM81254-2
CAS	81-25-4
Structure
Synonyms	3,7,12-Trihydroxy-cholan-24-oic acid
IUPAC Name	(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]pentanoic acid
Molecular Weight	408.58
Molecular Formula	C24H40O5
Canonical SMILES	CC(CCC(=O)O)C1CCC2C1(C(CC3C2C(CC4C3(CCC(C4)O)C)O)O)C
InChI	InChI=1S/C24H40O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-20,22,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14+,15-,16-,17+,18+,19-,20+,22+,23+,24-/m1/s1
InChI Key	BHQCQFFYRZLCQQ-OELDTZBJSA-N
Boiling Point	449.08 °C
Melting Point	200-201 °C(lit.)
Flash Point	9 °C
Purity	98%
Density	1.0310 g/cm³
Solubility	Soluble in glacial acetic acid, practically insoluble in benzene
Appearance	Solid
Storage	2-8 °C
Complexity	637
Covalently-Bonded Unit Count	1
Defined Atom Stereocenter Count	11
EC Number	201-337-8
Exact Mass	408.28757437
Heavy Atom Count	29
Hydrogen Bond Acceptor Count	5
Hydrogen Bond Donor Count	4
Isomeric SMILES	C[C@H](CCC(=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
MDL Number	MFCD00003672
Monoisotopic Mass	408.28757437
Physical State	Neat
Rotatable Bond Count	4
Topological Polar Surface Area	98 Ų

Knowledge & Learning Case Study Q&A

Cholic Acid in the Synthesis of Deoxycholic Acid

Wang X, et al. Organic Process Research & Development, 2024.

Cholic acid serves as a versatile precursor in the synthesis of deoxycholic acid, with significant implications for pharmaceutical applications. The novel synthesis pathway presented offers a more efficient and high-yield route to obtain deoxycholic acid with exceptional purity, making it suitable for use in research and therapeutic formulations.
Synthesis Pathway Overview
A new and streamlined method for synthesizing deoxycholic acid from cholic acid has been reported, highlighting its potential for high-purity production. The process begins with the selective oxidation of cholic acid to obtain compound 20, a key intermediate. This is followed by condensation with p-toluenesulfonylhydrazine to form hydrazone (21). The hydrazone is then reduced using sodium borohydride (NaBH4) through a three-step reaction to produce deoxycholic acid. This approach achieved a remarkable overall yield of 62.9%, with an HPLC purity of 100.00%, underscoring the method's efficiency and practicality.

Cholic Acid as a Capping and Reducing Agent in Nanoparticle Synthesis

Shanmugam C, et al. Reactive and Functional Polymers, 2024, 194, 105772.

Cholic acid, a bile acid derived from cholesterol, has been effectively utilized as a capping and reducing agent in the synthesis of nanoparticles (NPs). Cholic acid-functionalized star poly(DL-lactide) provides an efficient and green approach for the synthesis of Au and Ag nanoparticles. The CA-(PDLLA) stabilized nanoparticles demonstrated significant catalytic potential, suggesting their utility in various chemical and industrial applications.
Synthesis of CA-(PDLLA):
CA-(PDLLA) was synthesized through the ring-opening polymerization (ROP) of DL-lactide, using cholic acid as a core and Sn(Oct)2 as a catalyst. The reaction was conducted at a feed ratio of 1:120 (cholic acid to DL-lactide) under a nitrogen atmosphere at high temperatures (200°C for 10 minutes, followed by 150°C for 12 hours). The resulting CA-(PDLLA) polymer was purified by dissolving in tetrahydrofuran (THF) and precipitating with ethanol, yielding a star-shaped polymer suitable for nanoparticle synthesis.
Synthesis of Au and Ag Nanoparticles:
The CA-(PDLLA) polymer served as both a capping and reducing agent in the photochemical synthesis of Au and Ag NPs. For the synthesis of AuNPs, 50 μL of HAuCl4 solution was added to varying concentrations of CA-(PDLLA), with the final mixture irradiated under UV light (365 nm). The formation of AuNPs was indicated by a color change from light yellow to pink or red. Similarly, the synthesis of AgNPs was achieved by adding 50 μL of AgNO3 to different concentrations of CA-(PDLLA), followed by UV irradiation, resulting in a color change from colorless to brown or yellow.

Cholic Acid as a Chondroprotective Agent in Osteoarthritis Models

SHENG J, et al. Biocell, 2024, 48(7), 1095-1104.

This study investigates the chondroprotective properties of cholic acid (CA) using both in vitro and in vivo OA models. CA significantly mitigates cartilage degradation and inflammatory responses in OA models. By targeting the NF-κB/PERK/SIRT1 axis, CA offers a promising therapeutic approach for the treatment of osteoarthritis. Further studies could provide a deeper understanding of its potential clinical applications in OA management.
Methods: The study utilized the Cell Counting Kit-8 to determine the impact of CA on chondrocyte viability, identifying any cytotoxic effects. Various molecular biology techniques were applied to elucidate the signaling pathways through which CA may exert anti-inflammatory and chondroprotective effects. Furthermore, the effect of CA on cartilage degradation was evaluated in an OA model using Sprague-Dawley rats.
Results: CA exhibited significant chondroprotective effects by modulating key inflammatory markers. In TNF-α-treated chondrocytes, CA suppressed the upregulation of inflammatory mediators such as interleukin-1β (IL-1β), cyclooxygenase-2 (COX-2), and matrix metalloproteinase 13 (MMP-13). It also enhanced the expression of cartilage-specific proteins like aggrecan and type II collagen A1 (COL2A). Enrichment analysis of differentially expressed genes (DEGs) identified crucial signaling pathways, including IL-17, TNF, and toll-like receptor pathways, which were influenced by CA treatment. Additionally, CA impeded p65 nuclear translocation and inhibited IκBα phosphorylation, highlighting its impact on the NF-κB signaling pathway. The suppression of PERK, IRE1α, GRP78, and SIRT1 protein expression and downregulation of p-AMPKα further elucidated CA's protective role against TNF-α-induced chondrocyte inflammation.

Cholic Acid for the Development of LLC-202 in Liver Cancer Treatment

Jiang J, et al. Journal of Inorganic Biochemistry, 2023, 243, 112200.

Cholic acid has been leveraged in the development of a novel prodrug, LLC-202, designed for liver cancer treatment. The prodrug is created by conjugating cholic acid with an oxaliplatin analog using a 3-NH2-cyclobutane-1,1-dicarboxylate linker. The amide bond formed between the cholic acid moiety and the linker ensures a strong attachment, optimizing the compound's stability and functionality.
The synthesis of LLC-202 involves multiple steps:
Diethyl 3-TsO-1,1-cyclobutane diethyl dicarboxylate (2): Diethyl 3-hydroxy-1,1-cyclobutane dicarboxylate (1) reacts with triethylamine (Et3N), 4-dimethylaminopyridine (DMAP), and paratoluensulfonyl chloride (TsCl) in dichloromethane under nitrogen. After stirring overnight at room temperature, the product (2) is purified using column chromatography.
Diethyl 3-azido-1,1-cyclobutane dicarboxylate (3): Compound 2 reacts with sodium azide (NaN3) and Bu4NHSO4 in dimethylformamide (DMF) at 80°C under nitrogen. The product (3) is obtained through extraction and column chromatography.
Diethyl 3-amino-1,1-cyclobutane dicarboxylate (4): Compound 3 is hydrogenated using 10% Pd/C catalyst in ethyl acetate, yielding compound 4.
3-Cholic amide-1,1-cyclobutane dicarboxylic acid (6): Compound 5 reacts with NaOH and methanol at 50°C. After purification, compound 6 is obtained.
LLC-202: Compound 6 is reacted with cis-Pt(1R,2R-diaminocyclohexane)(H2O)22 in NaOH. The product is purified through dissolution in DMF, filtration, and re-precipitation in water, preparing it for structural characterization and biological testing.

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