3,5-Diethyl 1,4-dihydro-2,4,6-trimethyl-3,5-pyridinedicarboxylate
Basic information
- CAS
632-93-9- Standard SMILES
CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C- InChIKey
CDVAIHNNWWJFJW-UHFFFAOYSA-N- Molecular formula
- C14H21NO4
- Average molar mass
- 267.32 g/mol
- Monoisotopic mass
- 267.14705815
Overview
3,5-diethoxycarbonyl-1,4-dihydrocollidine is a dihydropyridine that is 2,4,6-trimethyl-1,4-dihydropyridine substituted by ethoxycarbonyl groups at positions 3 and 5. It has a role as a hepatic steatosis inducing agent. It is an ethyl ester and a dihydropyridine.
Names & identifiers
- Preferred name
- 3,5-Diethyl 1,4-dihydro-2,4,6-trimethyl-3,5-pyridinedicarboxylate
- IUPAC
- diethyl 2,4,6-trimethyl-1,4-dihydropyridine-3,5-dicarboxylate
- English name
- Diethyl 1,4-dihydro-2,4,6-trimethyl-3,5-pyridinedicarboxylate
- Molecular formula
- C14H21NO4
- Molecular weight
- 267.32
Names & synonyms
632-93-93,5-Dicarbethoxy-1,4-dihydrocollidineDICARBETHOXYDIHYDROCOLLIDINE3,5-Bis(ethoxycarbonyl)-1,4-dihydrocollidineDiethoxycarbonyldihydrocollidineRefChem:5870463,5-Diethoxycarbonyl-1,4-Dihydro-2,4,6-Trimethylpyridine3,5-Diethyl 1,4-dihydro-2,4,6-trimethyl-3,5-pyridinedicarboxylate211-188-0diethyl 2,4,6-trimethyl-1,4-dihydropyridine-3,5-dicarboxylateDDC (porphyrinogen)3,5-Diethoxycarbonyl-1,4-dihydro-2,4,6-collidine
Show more names
3,5-dicarbethoxy-1,4-dihydrocollidine, DDCDiethyl 1,4-dihydro-s-collidine-3,5-dicarboxylate
3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,4,6-trimethyl-, diethyl ester3,5-Diethoxycarbonyl-1,4-dihydrocollidineNSC 495281,4-Dihydro-3,5-dicarbethoxycollidineNSC 8910MFCD000059503,5-Dicarbethoxy-1,4-dihydro-2,4,6-trimethylpyridineMLS000766200
Database identifiers
- CAS
Properties
Computed structural properties
- XLogP
- 2.2
- Topological polar surface area
- 64.6 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 6
- Heavy atoms
- 19
- Formal charge
- 0
- Complexity
- 408
Physicochemical properties
- Melting point
- 130 · 130-132 °C(lit.)
- Boiling point
- 410.51 °C · 410.51°C (rough estimate)
- Density
- 1.1116 · 1.1116 (rough estimate)
- refractive index
- 1.528 · 1.5280 (estimate)
- storage temp.
- Keep in dark place,Sealed in dry,Room Temperature
- solubility
- 30 mg/ml; · 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 · 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 · 632-93-9(CAS DataBase Reference)
- EPA Substance Registry System
- 3 · 3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,4,6-trimethyl-, diethyl ester (632-93-9)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- US7979375
- hs_code
- 2933.39.9200
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-37/39
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
- Hazard statements
- H315-H319-H335
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
Chemistry & industry
Uses & manufacturing
General Manufacturing Information3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,4,6-trimethyl-, 3,5-diethyl ester: INACTIVE
Applications
DescriptionDiethyl 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.
UsesDiethyl 1,4-dihydro-2,4,6-trimethyl-3,5-pyridinedicarboxylate was used to induce Mallory-Denk body formation in mice in vivo.
Additional notes
DefinitionChEBI: A dihydropyridine that is 2,4,6-trimethyl-1,4-dihydropyridine substituted by ethoxycarbonyl groups at positions 3 and 5.
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