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

• 141-97-9 ethyl acetoacetate 
• 75-07-0 acetaldehyde 
• 108-05-4 vinyl acetate 
• 626-34-6 ethyl aminocrotonate 
• 106-93-4 ethylene dibromide 
• 29214-65-1 ethyl 3-iminobutanoate 
• 123-63-7 paracetaldehyde 
• 74955-84-3 2,4,4,6-tetramethyltetrahydro-(2H)-1,3-oxazine 
• 16250-89-8 2-methyl-3-phenyloxazolidine 
• 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 

Downstream Products

• 75-00-3 chloroethane 
• 75-07-0 acetaldehyde 
• 67-64-1 acetone 
• 1123-09-7 3,5-dimethyl-2-cyclohexen-1-one 
• 2199-54-4 2,4,5-trimethyl-3-ethoxycarbonylpyrrole 
• 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 
• 1721-13-7 ethyl 2,6-dimethylnicotinate 

Relevant articles and documents

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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.

Syntheses, Structural Characterization, Reactivity, and Theoretical Studies on Some Heteroligand Oxoperoxotungstate(VI)

White microcrystalline diamagnetic oxoperoxotungstate(VI) complexes K[WO(O2)2F]·H2O, K2[WO(O2)2(CO3)]·H2O, [WO(O2)(SO4)(H2O)2] have been synthesized from reaction of Na2WO4·2H2O with aqueous HF, solid KHCO3, aqueous H2SO4 (W:F? 1:3; W: CO3 2 ? 1:1; and W: SO4 2 ? 1:3), and an excess of 30% H2O2 at pH 7.5–8. Precipitation was completed by the addition of precooled acetone. The occurrence of terminal W?O and triangular bidentate O2 2 ?(C 2 v) in the synthesized compounds was ascertained from IR spectra. The IR spectra also suggested that the F? and SO4 2 ? ions in K[WO(O2)2F]·H2O and [WO(O2)(SO4)(H2O)2] were bonded to the WO +4 center in monodentate manner, while CO3 2 ? ion in K2[WO(O2)2(CO3)]·H2O binds the metal center in bidentate chelating fashion. The complex [WO(O2)(SO4)(H2O)2] is stable upto 110°C. The water molecule in [WO(O2)(SO4)(H2O)2] is coordinated to the WO +4 center, whereas it occurs as water of crystallization in the corresponding peroxo(fluoro) and peroxo(carbonato) compounds. Mass spectra of the compounds are in good agreement with the molecular formulae of the complexes. K2[WO(O2)2(CO3)]·H2O acts as an oxidant for bromide in the aqueous-phase bromination of organic substrates to the corresponding bromo-organics, and the complex also oxidizes Hantzsch-1,4-dihydropyridine to the corresponding pyridine derivative in excellent yield at room temperature. Density functional theory computation was carried out to compute the frequencies of relevant vibrational modes and electronic properties, and the results are in agreement with the experimentally obtained data.