246529-22-6

Basic information

• Product Name: Aramchol
• Synonyms: Aramchol;Aramchol (in progress);(3beta)-Arachidylamido-7alpha,12alpha-dihydroxy-5beta-cholan-24-oic acid;(3beta,5beta,7alpha,12alpha)-7,12-Dihydroxy-3-[(1-oxoeicosyl)amino]cholan-24-oic acid
• CAS NO: 246529-22-6
• Molecular Formula: C44H79NO5
• Molecular Weight: 702.10176
• EINECS: -0
• Mol File: 246529-22-6.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 806.0±65.0 °C(Predicted)
• Appearance: /
• Density: 1.05±0.1 g/cm3(Predicted)
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 4.76±0.10(Predicted)
• CAS DataBase Reference: Aramchol(CAS DataBase Reference)
• NIST Chemistry Reference: Aramchol(246529-22-6)
• EPA Substance Registry System: Aramchol(246529-22-6)

Safety Data

• Hazardous Substances Data: 246529-22-6(Hazardous Substances Data)

Usage

Uses

Aramchol is a fatty acid conjugate that exhibits?hypocholesterolemic effects. Studies have shown that aramchol?suppresses the activity of?stearoyl-CoA desaturase (SCD), which leads to reduction of obesity, fatty liver and insulin resistance.

Upstream product

• 506-30-9 Arachidic acid 
• 135053-61-1 methyl 3β-azido-7α,12α-dihydroxy-5β-cholan-24-oate 
• 1448-36-8 methyl cholate 
• 160836-52-2 Methyl 3α-methanesulphonyloxy-7α,12α-dihydroxy-5β-cholan-24-oate 
• 135053-62-2 (3β,5β,7α,12α)-3-amino-7,12-dihydroxycholan-24-oic acid methyl ester 
• 135053-65-5 3-mesylcholic acid 
• 153582-79-7 3β-aminocholic acid 
• 40140-09-8 eicosanoyl chloride 
• 81-25-4 cholic acid 
• 246529-32-8 3β-arachidamide-7α,12α-dihydroxycholic acid methyl ester 

Relevant articles and documents

Method for efficiently synthesizing Aramchol

The invention discloses a method for efficiently synthesizing Aramchol. The method comprises the following steps: firstly, generating an intermediate b-methyl cholate through esterification reaction of methanol and cholic acid molecules; reacting an alkylbenzene sulfonyl chloride with a specific structure with methyl cholate in the presence of an acid-binding agent, and selectively reacting with 3-hydroxyl of cholic acid molecules to synthesize a key intermediate c-3 alpha-O-alkylbenzene sulfonyl methyl cholate; and then protecting free hydroxyl in the intermediate c, and removing the free hydroxyl after the amidation reaction is finished, so that the problems of side reaction of acyl chloride and the free hydroxyl, serious emulsification phenomenon in the reaction process and difficulty in separation are effectively avoided.

Preparation methods of arachidic cholic acid and arachidic cholic acid intermediate

The invention discloses preparation methods of arachidic cholic acid and arachidic cholic acid intermediate. The preparation method of the arachidic cholic acid intermediate I provided herein includes the steps: in an organic solvent, performing reductive reaction on arachidic cholic acid intermediate II or II' and a reducing agent to obtain the arachidic cholic acid intermediate I; hydrazine hydrate or methylamine is used as the reducing agent. According to the preparation method, commercially available chemical products such as methyl cholate serve as starting materials, the arachidic cholic acid intermediate I can be prepared only by two steps, the reaction route is short, total yield can reach up to 76%, the purity of the prepared products can reach up to 98.00%, highly toxic products such as sodium azide are omitted, catalytic hydrogenation conditions are avoided, and the preparation method is safe to perform, low in production cost, environmentally friendly and suitable for industrial production.

Bile salt conjugates

The present invention relates to bile acid or bile salt fatty acid conjugates (hereinafter called “BAFAC), to their use in dissolving cholesterol gallstones in bile, preventing their occurrence or recurrence, to their use in reducing or preventing arteriosclerosis and to methods for the treatment of said diseases. The conjugates are of the formula W—X—G in which G is a bile acid or bile salt radical, W stands for one or two saturated fatty acid radicals and X is either a direct bond or a bonding member between said bile acid or bile salt and the fatty acid(s). The conjugation is advantageously performed at a position selected among the 3, 6, 7, 12 and 24 positions of the bile acid or bile salt nucleus.