632-93-9

Basic information

• Product Name: DIETHYL 1,4-DIHYDRO-2,4,6-TRIMETHYL-3,5-PYRIDINEDICARBOXYLATE
• Synonyms: DIETHYL 1,4-DIHYDRO-2,4,6-TRIMETHYL-3,5-PYRIDINEDICARBOXYLATE;DIETHYL 1,4-DIHYDRO-2,4,6-TRIMETHYLPYRIDINE-3,5-DICARBOXYLATE;3,5-DICARBETHOXY-1,4-DIHYDRO-2,4,6-TRIMETHYLPYRIDINE;3,5-DIETHOXYCARBONYL-1,4-DIHYDRO-2,4,6-COLLIDINE;1,4-DIHYDRO-2,4,6-TRIMETHYL-3,5-PYRIDINEDICARBOXYLIC ACID DIETHYL ESTER;5-pyridinedicarboxylicacid,1,4-dihydro-2,4,6-trimethyl-diethylester;Dicarbethoxydihydrocollidine;diethyl dihydro-2,4,6-trimethyl-3,5-pyridinedicarboxylate
• CAS NO: 632-93-9
• Molecular Formula: C₁₄H₂₁NO₄
• Molecular Weight: 267.32
• EINECS: 211-188-0
• Mol File: 632-93-9.mol
• Article Data: 35

Chemical Properties

• Melting Point: 130-132 °C(lit.)
• Boiling Point: 410.51°C (rough estimate)
• Flash Point: 123.3ºC
• Appearance: /
• Density: 1.1116 (rough estimate)
• Vapor Pressure: 0.000123mmHg at 25°C
• Refractive Index: 1.5280 (estimate)
• Storage Temp.: Flammables area
• PKA: 3.53±0.70(Predicted)
• CAS DataBase Reference: DIETHYL 1,4-DIHYDRO-2,4,6-TRIMETHYL-3,5-PYRIDINEDICARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: DIETHYL 1,4-DIHYDRO-2,4,6-TRIMETHYL-3,5-PYRIDINEDICARBOXYLATE(632-93-9)
• EPA Substance Registry System: DIETHYL 1,4-DIHYDRO-2,4,6-TRIMETHYL-3,5-PYRIDINEDICARBOXYLATE(632-93-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• RTECS: US7979375
• Hazardous Substances Data: 632-93-9(Hazardous Substances Data)

Usage

Description

Diethyl 1,4-dihydro-2,4,6-trimethyl-3,5-pyridinedicarboxylate (DDC) inhibits heme production by inhibiting ferrochelatase, the enzyme that catalyzes the addition of Fe2+ to protoporphyrin IX to create heme B. Chronic DDC administration induces Mallory-Denk body formation, a feature of alcoholic and non-alcoholic hepatitis, and reduces IL-12A methylation in mouse liver.

Chemical Properties

almost white crystalline powder

Uses

Diethyl 1,4-dihydro-2,4,6-trimethyl-3,5-pyridinedicarboxylate was used to induce Mallory-Denk body formation in mice in vivo.

Definition

ChEBI: A dihydropyridine that is 2,4,6-trimethyl-1,4-dihydropyridine substituted by ethoxycarbonyl groups at positions 3 and 5.

Biochem/physiol Actions

Diethyl 1,4-dihydro-2,4,6-trimethyl-3,5-pyridinedicarboxylate blocks the heme synthesis and prevents the induction of hepatic heme oxygenase-1 in mice.

Purification Methods

Crystallise the ester from hot EtOH/water mixture. [Beilstein 22 H 147, 22 I 529, 22 II 100, 22 III/IV 1594.]

InChI:InChI=1/C14H21NO4/c1-6-18-13(16)11-8(3)12(14(17)19-7-2)10(5)15-9(11)4/h8,11H,6-7H2,1-5H3/t8-,11?/m1/s1

Upstream product

• 64-17-5 ethanol 
• 75926-37-3 5-Benzylsulfanylcarbonyl-2,4,6-trimethyl-1,4-dihydro-pyridine-3-carboxylic acid ethyl ester 
• 60544-22-1 1-methylpyrimidin-1-ium iodide 
• 41867-20-3 ethyl (E)-3-aminobut-2-enoate 
• 21759-71-7 ethyl N-methyl-β-aminocrotonate 
• 108-05-4 vinyl acetate 
• 626-34-6 ethyl aminocrotonate 
• 50-00-0 formaldehyd 
• 141-97-9 ethyl acetoacetate 
• 506-87-6 ammonium carbonate 
• 75-07-0 acetaldehyde 
• 631-61-8 ammonium acetate 
• 1150-55-6 2,4,6-trimethylpyridine-3,5-dicarboxylic acid diethyl ester 
• 17469-21-5 β-(Dimethylamino)crotonsaeure-ethylester 

Downstream Products

• 1721-13-7 ethyl 2,6-dimethylnicotinate 
• 2199-54-4 2,4,5-trimethyl-3-ethoxycarbonylpyrrole 
• 14258-08-3 diethyl 1,2,4,6-tetramethyl-1,4-dihydropyridine-3,5-dicarboxylate 
• 1123-09-7 3,5-dimethyl-2-cyclohexen-1-one 
• 64-17-5 ethanol 
• 74-85-1 ethene 
• 1149-24-2 2,6-dimethyl-pyridine-3,5-dicarboxylic acid diethyl ester 
• 20329-30-0 1,3-Bis-(N',N'-diphenyl-hydrazino)-5-chlor-2,4,6-tricyan-benzol 
• 1150-55-6 2,4,6-trimethylpyridine-3,5-dicarboxylic acid diethyl ester 
• 18998-40-8 N_.N-Diphenyl-N'-(3.5-dichlor-2.4.6-tricyan-phenyl)-hydrazin 
• 20329-31-1 1,3,5-Tris-(N',N'-diphenyl-hydrazino)-2,4,6-tricyan-benzol 
• 61360-76-7 2,4-Bis-(N',N'-diphenyl-hydrazino)-6-piperidin-1-yl-benzene-1,3,5-tricarbonitrile 
• 75-00-3 chloroethane 
• 75-07-0 acetaldehyde 

Relevant articles and documents

-

-

CAN mediated mechanochemical synthesis of substituted pyridine derivatives

A simple, green and cost-effective protocol has been devised for the synthesis of 4-substituted-2,6-dimethyl-3,5-pyridinecarboxylates from Hantzsch-type 1,4-dihydropyridines via rapid oxidation in excellent yields using 1.5 equivalent of ceric ammonium nitrate within 15 minutes in solvent-free conditions. The method was able to furnish the products in excellent yields. The products obtained were characterized by their NMR and melting points data.

Pyridine five formic acid and potassium compound and its preparation method

The invention relates to a pyridine-2,3,4,5,6-pentacarbonic acid dipotassium compound and a preparation method thereof. The pyridine-2,3,4,5,6-pentacarbonic acid dipotassium compound is characterized in that a structure of the compound is shown as a following formula. The preparation method comprises the following steps: ethyl acetoacetate and acetaldehyde are performed with a chemical reaction under catalysis effect of organic amine, then is reacted with ammonia to obtain 2,4,6-trimethyl-1,4-dihydropyridine-3,5-diethyl phthalate; nitric acid oxidation is carried out to obtain 2,4,6-trimethylpyridine-3,5-diethyl phthalate; KOH hydrolysis is carried out to obtain 2,4,6-trimethylpyridine-3,5-dioctyl phthalate dipotassium; and finally KMnO4 oxidation is carried out to obtain the pyridine-2,3,4,5,6-pentacarbonic acid dipotassium compound. The compound can be used as a pH buffering agent, and has large buffer capability when pH value is 2.3. The preparation method has the advantages of simple preparation, low energy consumption, easy acquisition of raw materials, and good popularization and application prospects.