4-[(5S,10S,13R,17R)-10,13-dimethyl-3,7,12-trioxo-1,2,4,5,6,8,9,11,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]pentanoic acid

Base Information

• Chemical Name: 4-[(5S,10S,13R,17R)-10,13-dimethyl-3,7,12-trioxo-1,2,4,5,6,8,9,11,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]pentanoic acid
• CAS No.: 81-23-2
• Molecular Formula: C24H34O5
• Molecular Weight: 402.531
• Hs Code.: 2918300000
• NSC Number: 757805
• Wikidata: Q27166907
• ChEMBL ID: CHEMBL3039061
• Mol file: 81-23-2.mol

Synonyms:SR-05000001544;Spectrum_001172;Spectrum2_001375;Spectrum3_001411;BSPBio_003082;KBioSS_001652;SPECTRUM1500907;SPBio_001330;CHEMBL3039061;CHEBI:95125;KBio2_001652;KBio2_004220;KBio2_006788;KBio3_002302;HMS2092O06;Pharmakon1600-01500907;CCG-38851;NSC757805;NSC-757805;NCGC00178307-01;4-[(5S,10S,13R,17R)-10,13-dimethyl-3,7,12-trioxo-1,2,4,5,6,8,9,11,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]pentanoic acid;SBI-0206710.P001;AB01563269_01;SR-05000001544-1;SR-05000001544-2;BRD-A11551002-001-03-8;Q27166907

Chemical Property of 4-[(5S,10S,13R,17R)-10,13-dimethyl-3,7,12-trioxo-1,2,4,5,6,8,9,11,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]pentanoic acid

Chemical Property:

• Appearance/Colour: white to off-white amorphous powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 238-240 °C
• Refractive Index: 30.5 ° (C=2, Dioxane)
• Boiling Point: 581.5 °C at 760 mmHg
• PKA: pKa 5.12(H2O t = 20 c > CMC) (Uncertain)
• Flash Point: 319.5 °C
• PSA: 88.51000
• Density: 1.172 g/cm³
• LogP: 4.07330
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: ethanol: 10 mg/mL
• Water Solubility.: 65mg/L(30 oC)
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 402.24062418
• Heavy Atom Count: 29
• Complexity: 756

Purity/Quality:

98%, ^*data from raw suppliers

Dehydrocholic acid ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CCC(=O)O)C1CCC2C1(C(=O)CC3C2C(=O)CC4C3(CCC(=O)C4)C)C
• Isomeric SMILES: CC(CCC(=O)O)[C@H]1CCC2[C@@]1(C(=O)CC3C2C(=O)C[C@H]4[C@@]3(CCC(=O)C4)C)C
• Description: Dehydrocholic acid is a semisynthetic bile acid, which is made by the oxidation of cholic acid by chromic acid. It can increase the output of bile by the liver and the filling of the gallbladder. Dehydrocholic acid aids the digestion of fats and increases absorption of fat soluble vitamins. It is used as a gastrointestinal agent that stimulates the flow of bile into the duodenum (cholagogue) or stimulate the production of bile by the liver (choleretic). It is also used as laxative to relief constipation, diuretic, and a diagnostic aid.
• Uses: Dehydrocholic Acid is a derivative of Cholic Acid (C432600). a choleretic produced by, and isolated from liver cells. antibacterial
• Therapeutic Function: Choleretic, Diuretic, Diagnostic aid

Technology Process of 4-[(5S,10S,13R,17R)-10,13-dimethyl-3,7,12-trioxo-1,2,4,5,6,8,9,11,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]pentanoic acid

There total 37 articles about 4-[(5S,10S,13R,17R)-10,13-dimethyl-3,7,12-trioxo-1,2,4,5,6,8,9,11,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]pentanoic acid 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: 100.0%

cholic acid (81-25-4) → dehydrocholic acid (81-23-2)

Guidance literature:

With sodium hydroxide; sodium perchlorate; sodium chloride; In water; at 25 ℃; for 40h; pH=12; Electrochemical reaction; 50 mA;

DOI:10.1016/S0039-128X(00)00185-9

Reference yield: 100.0%

3,7,12-trihydroxy-5β-cholan-24-oic acid → dehydrocholic acid (81-23-2)

Guidance literature:

With jones' reagent; In acetone; for 0.0833333h;

DOI:10.1021/jo020146b

Reference yield: 94.0%

C27H46O5 → dehydrocholic acid (81-23-2)

Guidance literature:

C₂₇H₄₆O₅; With potassium sulfate; cerous nitrate; at 8 ℃; for 2.33333h; Large scale;

With Tetradecanoic acid 1-methylethyl ester; for 3h; Temperature; Large scale;

upstream raw materials:

cholic acid

(24RS,25RS)-3α,7α,12α,24,26-pentahydroxy-5β-cholestan-27-yl sodium sulfate

sodium cholate

water

Downstream raw materials:

methyl 3,7,12-trioxo-5β-cholan-24-oate

cholanic acid

7,12-dioxo-5β-cholan-24-oic acid

5β-cholanoic acid-(24)-ethyl ester

Refernces

Molecular structure of perfluoroadamantane from gas-phase electron diffraction

10.1016/S0022-2860(97)00412-2

The research aimed to determine the molecular structure of perfluoroadamantane using gas-phase electron diffraction. The study sought to examine the structural consequences of hydrogen/fluorine substitution in adamantane, a carbon-cage molecule with high symmetry, by comparing the bond lengths and angles of perfluoroadamantane to those of adamantane. The researchers found that perfluorination expanded the adamantane cage, with a significant lengthening of the C-C bonds by 0.02 ?, attributed to the electron-withdrawing ability of fluorine ligands. The chemicals used in the process included adamantane, sodium fluoride, anhydrous hydrogen fluoride, and Freon-113 for extraction, as well as helium for agitation during the electrochemical fluorination process. The final product, perfluoroadamantane, was obtained with a yield of 31.1% based on the sample fed and a purity of 99.3% as confirmed by gas chromatography.

Chlorination of various substrates in subcritical carbon tetrachloride

10.1016/j.tet.2010.02.021

The research investigates the chlorination of various substrates, including aliphatic hydrocarbons and the side chains of aromatic hydrocarbons, under subcritical carbon tetrachloride (CCl4) conditions. The study explores the reactions of different compounds such as adamantane, chlorocyclododecane, and various aromatic hydrocarbons, including 1,4-disubstituted benzenes. The chlorination process involves the generation of chloro radicals from the C–Cl bond cleavage of carbon tetrachloride under high-temperature conditions. The study also examines the stability and transformation of other compounds like ketones, sulfones, sulfoxides, and ole?ns under these conditions. The results show that while ketones and sulfones remain stable, sulfoxides are converted into sul?des, and ole?ns form coupling adducts with carbon tetrachloride. The research highlights the unique reactivity of subcritical carbon tetrachloride in facilitating these chlorination reactions and provides insights into the potential applications and mechanisms involved in this process.

Synthesis and Transformations of Aryl-Substituted Alkenes of the Adamantane Series

10.1134/S1070428018070047

The research investigates the synthesis and chemical transformations of aryl-substituted alkenes containing adamantane fragments. The study aims to explore the behavior of these compounds in radical and carbocationic reactions, given the unique structural properties of adamantane derivatives and their potential applications in various fields, including pharmaceuticals and materials science. The key chemicals used in this research include adamantane derivatives such as 1-[(Z,E)-3-phenylprop-2-en-1-yl]adamantane and 1-[(Z)-3-phenylprop-1-en-1-yl]adamantane, synthesized via the Wittig reaction. The researchers also employed reagents like N-bromosuccinimide (NBS) for bromination and sulfuric acid for the Ritter reaction. The study found that the aryl-substituted alkenes exhibited different chemical behaviors depending on their structure and the nature of the acid catalyst used. The products of these reactions included secondary amides, sulfonic acid derivatives, and homoadamantane γ-sultone. The research concludes that the adamantane-containing alkenes can undergo complex transformations, leading to the formation of various functionalized adamantane derivatives, which could be valuable for the development of new materials and pharmaceutical compounds.

Synthesis and crystallographic insight into the structural aspects of some novel adamantane-based ester derivatives

10.3390/molecules201018827

This research aims on the synthesis and structural characterization of a series of novel adamantane-based ester derivatives, which are commercially significant for their potential applications in treating neurological conditions, type-2 diabetes, and viral infections. The study aimed to investigate the antioxidant and anti-inflammatory properties of these compounds. The synthesis involved the reaction of 1-adamantyl bromomethyl ketone with various carboxylic acids using potassium carbonate in dimethylformamide at room temperature. The resulting compounds were characterized using FTIR, NMR, and single-crystal X-ray diffraction analysis. The research concluded that the introduction of the adamantane moiety led to synclinal conformation in all molecular structures, and these compounds exhibited selective antioxidant abilities, particularly in scavenging hydrogen peroxide radicals. Notably, compounds containing nitrogen, such as 2p, 2q, and 2r, showed strong anti-inflammatory effects, outperforming the standard drug diclofenac sodium, suggesting their potential as promising anti-inflammatory agents for future clinical use.