DIETHYL 1,4-DIHYDRO-2,4,6-TRIMETHYL-3,5-PYRIDINEDICARBOXYLATE Chemical Properties

Melting point:

130-132 °C(lit.)

Boiling point:

410.51°C (rough estimate)

Density 

1.1116 (rough estimate)

refractive index 

1.5280 (estimate)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

DMF: 30 mg/ml; DMF:PBS (pH 7.2); (1:7): 0.125 mg/ml; DMSO: 20 mg/ml; Ethanol: 20 mg/ml

pka

3.53±0.70(Predicted)

form 

powder to crystal

color 

White to Orange to Green

InChI

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

InChIKey

CDVAIHNNWWJFJW-UHFFFAOYSA-N

SMILES

C1(C)NC(C)=C(C(OCC)=O)C(C)C=1C(OCC)=O

CAS DataBase Reference

632-93-9(CAS DataBase Reference)

EPA Substance Registry System

3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,4,6-trimethyl-, diethyl ester (632-93-9)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

WGK Germany 

3

RTECS 

US7979375

HS Code 

2933.39.9200

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

DIETHYL 1,4-DIHYDRO-2,4,6-TRIMETHYL-3,5-PYRIDINEDICARBOXYLATE Usage And Synthesis

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.]

References

[1] J. ONISAWA R L. Effects of diethyl-1, 4-dihydro-2, 4,6-trimethylpyridine-3,5-dicarboxylate on the metabolism of porphyrins and iron.[J]. The Journal of Biological Chemistry, 1963, 44 1: 724-727. DOI: 10.1016/s0021-9258(18)81326-6
[2] QX YUAN. Mallory body induction in drug-primed mouse liver[J]. Hepatology, 1996, 24 3: Pages 603-612. DOI: 10.1053/jhep.1996.v24.pm0008781332
[3] J. OLIVA  S. W F. Changes in IL12A methylation pattern in livers from mice fed DDC[J]. Experimental and molecular pathology, 2012, 92 2: Pages 191-193. DOI: 10.1016/j.yexmp.2012.01.001

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