738606-46-7

Basic information

• Product Name: ETC-1002
• Synonyms: ETC-1002;Bempedoic Acid;ETC-1002 (ESP 55016);ESP 55016
• CAS NO: 738606-46-7
• Molecular Formula: C₁₉H₃₆O₅
• Molecular Weight: 344.48614
• Product Categories: API
• Mol File: 738606-46-7.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 506.5±35.0 °C(Predicted)
• Appearance: /
• Density: 1.045±0.06 g/cm3(Predicted)
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 4.55±0.45(Predicted)
• CAS DataBase Reference: ETC-1002(CAS DataBase Reference)
• NIST Chemistry Reference: ETC-1002(738606-46-7)
• EPA Substance Registry System: ETC-1002(738606-46-7)

Safety Data

• Hazardous Substances Data: 738606-46-7(Hazardous Substances Data)

Usage

Description

Different sources of media describe the Description of 738606-46-7 differently. You can refer to the following data:
1. Etc-1002 is a small molecule that can be used orally to lower LDL-C and is an activator of LIVER AMPK. ETC-1002 has an effective inhibitory effect on liver ATP-Citrate lyase.
2. ETC-1002 is a prodrug form of ETC-1002-CoA. ETC-1002 is conjugated to coenzyme A (CoA) by very long-chain acyl-CoA synthetase-1 (ACSVL1) to form ETC-1002-CoA, which inhibits ATP citrate lyase (Ki = 2 μM) and activates AMP-activated protein kinase (AMPK). ETC-1002 suppresses total lipid synthesis in wild-type and AMPKβ1 knockout primary murine hepatocytes. In vivo, ETC-1002 (30 mg/kg) prevents increases in hepatic cholesterol and reduces the size of aortic atherosclerotic lesions induced by a high-fat high-cholesterol diet in Apoe-/-/Ampkβ1-/- (DKO) mice.

Uses

ETC-1002 (Bempedoic acid, ESP-55016),also known as Bempedoic acid, is an orally available, once-daily LDL-C lowering small molecule designed to lower elevated levels of LDL-C and to avoid side effects associated with existing LDL-C lowering therapies.ETC-1002 is an activator of hepatic AMP-activated protein kinase (AMPK). It has potent inhibitory activity against hepatic ATP-citrate lyase(IC50=29 uM).

Upstream product

• 53545-96-3 6-bromo-2,2-dimethylhexanenitrile 
• 53545-94-1 2,2-dimethyl-6-chloro-n-hexanenitrile 
• 123469-92-1 ethyl-2,2-dimethyl-7-bromoheptanoate 
• 54512-75-3 1-bromo-5-chloropentane 
• 111-24-0 1,5-dibromo-pentane 
• 738606-43-4 2,2,14,14-tetramethyl-8-oxopentadecanedioic acid diethyl ester 
• 738606-64-9 diethyl 8‐hydroxy‐2,2,14,14‐tetramethylpentadecanedioate 
• 30452-00-7 methyl (3-bromo-2,2-dimethyl) propionate 
• 413624-71-2 8-oxo-2,2,14,14-tetramethylpentadecanedioic acid 
• 116288-13-2 1,11-dibromoundecan-6-one 

Relevant articles and documents

Preparation method 8 -hydroxy -2, 2, 14 and 14 -tetramethyl-pentadecanedioic acid

The invention relates to a preparation method of 8 - hydroxyl -2, 2, 14 and 14 -tetramethyldodecanedioic acid. The method utilizes isobutyronitrile (II) and 1, 4 - dihalogenated butane as raw materials to obtain 2, 2 -dimethyl -6 -halogenated n-hexanenitrile, then with 1, 3 -di P-substituted acetone (substituent P) COOR. CN Or CONH2 Through substitution reaction, hydrolysis, acidification and decarboxylation, 8 - oxo -2, 2, 14, 14 - tetramethyldodecanedioic acid, and a boric acid reducing agent are subjected to reduction reaction, and then hydrolyzed and acidified to obtain a target product. To the invention, isobutyronitrile is adopted as an initial raw material, and raw materials are cheap and easily available. Easy operation, reaction conditions easily realize. The system is safe, environment-friendly and small in wastewater generation amount. The method has the advantages of low cost, high reaction selectivity, less byproducts, high target product yield and purity and suitability for green industrial production.

Preparation method of Bempedoic acid

The invention discloses a preparatino method ofBempedoic acid. The preparation method comprises the following steps: carrying out condensation reaction on ethyl isobutyrate and 2-(5-bromo-n-amyl)-1, 3-dioxocyclopentane under the effect of an alkali accelerator, carrying out hydrolysis reaction to obtain an intermediate 8-oxa-2, 2-dimethyl octanoic acid, and carrying out Grignard reaction on the intermediate and 7-bromo-2, 2-dimethyl heptanoic acid to obtain the Bempedoic acid. The preparation method is simple in process, mild in condition, safe and environment-friendly, and provides a new way for industrial production.

Synthesis of bempedoic acid through electrochemical decarboxylation of dialkylated malonic acid

Bempedoic acid is a small-molecule inhibitor of adenosine triphosphate-citrate lyase (ACL) that is effective in the treatment of hypercholesterolemia and hypertension. In this paper, a new, six-step synthesis of bempedoic acid with 42% overall yield is reported. Ketone formation by electrochemical decarboxylation of dialkylated malonic acid is introduced as the key step of this process. This method uses mild conditions and its high efficiency makes it potentially suitable for industrial production.