Pharmakon1600-01500837

Base Information

• Chemical Name: Pharmakon1600-01500837
• CAS No.: 474-25-9
• Molecular Formula: C24H40O4
• Molecular Weight: 392.579
• Hs Code.: 29181990
• NSC Number: 757798
• Mol file: 474-25-9.mol

Synonyms:SR-05000001555;Spectrum_000372;Spectrum2_000614;Spectrum3_000631;Spectrum4_001706;Spectrum5_000412;BSPBio_002222;KBioGR_002032;KBioSS_000852;DivK1c_000571;SPECTRUM1500837;SPBio_000548;SCHEMBL1688710;HMS501M13;KBio1_000571;KBio2_000852;KBio2_003420;KBio2_005988;KBio3_001722;NINDS_000571;HMS1921K12;HMS2092M10;Pharmakon1600-01500837;CCG-38531;NSC757798;SDCCGMLS-0066932.P001;IDI1_000571;NCGC00178755-01;SBI-0051696.P002;AB01562946_01;SR-05000001555-1;SR-05000001555-2

Chemical Property of Pharmakon1600-01500837

Chemical Property:

• Appearance/Colour: Off-white solid
• Melting Point: 165-167 °C(lit.)
• Refractive Index: 1.558
• Boiling Point: 547.148 °C at 760 mmHg
• PKA: pKa 4.34 (Uncertain)
• Flash Point: 298.8 °C
• PSA: 77.76000
• Density: 1.129 g/cm³
• LogP: 4.47790
• Storage Temp.: Refrigerator
• Solubility.: PRACTICALLY INSOLUBLE
• Water Solubility.: PRACTICALLY INSOLUBLE
• XLogP3: 4.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 392.29265975
• Heavy Atom Count: 28
• Complexity: 605

Purity/Quality:

99%, ^*data from raw suppliers

Chenodeoxycholic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 63
• Safety Statements: 22-24/25-45-36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(CCC(=O)O)C1CCC2C1(CCC3C2C(CC4C3(CCC(C4)O)C)O)C
• Isomeric SMILES: C[C@H](CCC(=O)O)[C@H]1CCC2[C@@]1(CCC3C2[C@@H](C[C@H]4[C@@]3(CC[C@H](C4)O)C)O)C
• Uses: Chenodeoxycholic acid is a bile acid synthesized in the liver from cholesterol. henodeoxycholic acid has been used in a study to assess its effects as a long-term replacement therapy for cerebrotendinous xanthomatosis (CTX). It has also been used in a study to investigate its effects on the small-intestinal absorption of bile acids in patients with ileostomies. Chenodeoxycholic acid is a bile acid that induces apoptosis through protein kinase C signaling pathways.It is a major bile acid in many vertebrates, occurring as the N-glycine and/or N-taurine conjugate. With other bile acids, forms mixed micelles with lecithin in bile which solubilize cholesterol and thus facilitates its excretion.Bile acids are essential for solubilization and transport of dietary lipids, are the major products of cholesterol catabolism, and are physiological ligands for farnesoid X receptor (FXR), a nuclear receptor that regulates genes involved in lipid metabolism.They are also inherently cytotoxic, as physiological imbalance contributes to increased oxidative stress. Bile acid-controlled signaling pathways are promising novel targets to treat such metabolic diseases as obesity, type II diabetes, hyperlipidemia, and atherosclerosis. Chenodeoxycholic acid is widely utilized in therapeutic applications. It is applied in medical therapy to dissolve gallstones. It is employed in the treatment of cerebrotendineous xanthomatosis. It is used to treat constipation and cerebrotendineous xanthomatosis. It acts as a urea receptor in supramolecular chemistry which can contain anions. It is a staining additive commonly used with ruthenium or organic photo-sensitizers in the preparation of staining solutions for dye solar cells. Chenodeoxycholic Acid is a staining additive commonly used with ruthenium or organic photo-sensitizers in the preparation of staining solutions for Dye Solar Cells. This co-adsorbent will prevent dye aggregation on the semiconductor surface, reducing losses in the solar cell's operation. Chenodeoxycholic Acid is a white solid added with the dye powder to the solvent while preparing staining solutions. The concentration of co-adsorbent is typically 10 fold the dye concentration. Chenodeoxycholic acid has been used in a study to assess its effects as a long-term replacement therapy for cerebrotendinous xanthomatosis (CTX). It has also been used in a study to investigate its effects on the small-intestinal absorption of bile acids in patients with ileostomies. Chenodeoxycholic acid (CDCA) is a hydrophobic primary bile acid that activates nuclear receptors involved in cholesterol metabolism.EC50 concentrations for activation of FXR range from 13-34 μM.In cells, CDCA also binds to bile acid binding proteins (BABP) with a reported stoichiometry of 1:2.CDCA toxicity is linked to increased cellular glutathione levels and increased oxidative stress. Exposure of cells to excess CDCA contributes to liver and intestinal cancers. A major bile acid in many vertebrates, occurring as the N-glycine and/or N-taurine conjugate. With other bile acids, forms mixed micelles with lecithin in bile which solubilize cholesterol and thus fa cilitates its excretion. Fcilitates fat absorption in the small intestine by micellar solubilization of fatty acids and monoglycerides. Anticholelithogenic. Epimeric with Ursodiol. An apoptosis inducer via PKC-dependent signalling pathway.
• Description: Chenodeoxycholic acid is the first agent to be introduced into the US market for the treatment of radiolucent gallstones. Large scale clinical trials have demonstrated the safety and efficacy of this agent. Chenodeoxycholic acid reduces the biliary concentration of cholesterol relative to that of bile acids and phospholipid, reducing the saturation and thus the lithogenicity of the bile. Success rates in dissolving gallstones are in the range of 50-70% within 4-24 months of treatment. Continuation of the drug after stone dissolution may be required to prevent reoccurrence. Chenodeoxycholic acid is the 7α-isomer of ursodeoxycholic acid which was introduced into the European market in 1978. chenodeoxycholic acid structure
• Therapeutic Function: Gallostone dissolving agent

Technology Process of Pharmakon1600-01500837

There total 187 articles about Pharmakon1600-01500837 which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

3α,7α-Dihydroxy-chol-11-ensaeure → chenodeoxycholic acid (474-25-9)

Guidance literature:

With palladium on activated charcoal; hydrogen; In methanol; at 70 ℃; for 12h; under 30003 Torr;

Reference yield: 97.0%

(4R)-methyl 4-((3R,5R,7R,10S,13R,17R)-3-acetoxy-7-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoate (19684-68-5) → chenodeoxycholic acid (474-25-9)

Guidance literature:

With water; sodium hydroxide; In methanol; for 1h; Reflux;

DOI:10.1016/j.steroids.2020.108594

Reference yield: 95.0%

7-Ketolithocholic acid (4651-67-6) → chenodeoxycholic acid (474-25-9) + ursodeoxycholic acid (128-13-2)

Guidance literature:

7-Ketolithocholic acid; With potassium tert-butylate; palladium(II) hydroxide; potassium hydroxide; In isopropyl alcohol; at 20 ℃; for 0.166667h;

With hydrogen; In isopropyl alcohol; at 40 - 80 ℃; Reagent/catalyst; Temperature;

upstream raw materials:

3,7-diketocholanic acid

methyl 3α,7α-diacetoxy-12-one-5β-cholest-24-carboxylate

7-Ketolithocholic acid

sodium ethanolate

Downstream raw materials:

5β-cholestane-3α,7α-diol

7-Ketolithocholic acid

ursodeoxycholic acid

3α,7α-diformyloxy-5β-cholan-24-oic acid

Refernces

• 1、 Kobayashi,Hagiwara,Morisaki,Yuri,Fujimoto. "Non-stereospecific formation of 3α,7α,24-trihydroxy-5β-cholestan-26- oic acid during chenodeoxycholic acid biosynthesis". . p. 1536 - 1538. Retrieved 1994.
• 2、 -. "Method for synthesizing 3alpha, 7alpha-dihydroxy-5-beta-cholanic acid from duck cholic acid". Paragraph 0013. . Retrieved 2021/02/06.
• 3、 -. "Preparation method of chenodeoxycholic acid". Paragraph 0089-0090; 0138-0143; 0181-0183. . Retrieved 2021/01/24.