1269259-99-5

Basic information

• Product Name: (2E,4E)-ethyl 5-(-4-methoxy-2,3,6-trimethylphenyl)-3-methylpenta-2,4-dienoate
• Synonyms: (2E,4E)-ethyl 5-(-4-methoxy-2,3,6-trimethylphenyl)-3-methylpenta-2,4-dienoate
• CAS NO: 1269259-99-5
• Molecular Weight: 288.387
• Mol File: 1269259-99-5.mol

Chemical Properties

• CAS DataBase Reference: (2E,4E)-ethyl 5-(-4-methoxy-2,3,6-trimethylphenyl)-3-methylpenta-2,4-dienoate(CAS DataBase Reference)
• NIST Chemistry Reference: (2E,4E)-ethyl 5-(-4-methoxy-2,3,6-trimethylphenyl)-3-methylpenta-2,4-dienoate(1269259-99-5)
• EPA Substance Registry System: (2E,4E)-ethyl 5-(-4-methoxy-2,3,6-trimethylphenyl)-3-methylpenta-2,4-dienoate(1269259-99-5)

Safety Data

• Hazardous Substances Data: 1269259-99-5(Hazardous Substances Data)

Upstream product

• 54344-92-2 2,3,6-trimethyl-4-methoxy-benzaldehyde 
• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 62924-31-6 1-(2,5,6-trimethyl-4-methoxyphenyl)-but-1-en-3-one 
• 20469-61-8 2,3,5-trimethylanisole 
• 697-82-5 2,3,5-trimethylphenol 
• 41891-54-7 diethyl 3-(ethoxycarbonyl)-3-methylprop-2-en-yl phosphate 
• 65527-85-7 ethyl (E)-4-hydroxy-3-methyl-2-butenoate 

Downstream Products

• 63650-98-6 5-(4-methoxy-2,3,6-trimethylphenyl)-3-methylpenta-2,4-dien-1-ol 
• 69877-38-9 5-(4-methoxy-2,3,6-trimethylphenyl)-3-methyl-2(E),4(E)-pentadien-1-al 
• 74479-62-2 2-((1E,3E)-5-bromo-3-methylpenta-1,3-dien-1-yl)-5-methoxy-1,3,4-trimethylbenzene 
• 74479-69-9 diethyl ((2E,4E)-5-(4-methoxy-2,3,6-trimethylphenyl)-3-methylpenta-2,4-dien-1-yl)phosphonate 
• 1621283-99-5 4,4’-((1E,3E,5E)-3-methylhexa-1,3,5-triene-1,6-diyl)bis(1-methoxy-2,3,5-trimethylbenzene) 
• 1621283-95-1 4,4’-((1E,3E,5E)-3-methylhexa-1,3,5-triene-1,6-diyl)bis(2,3,5-trimethylphenol) 
• 1621284-00-1 4,4’-((1E,3E,5E,7E,9E)-3,8-dimethyldeca-1,3,5,7,9-pentaene-1,10-diyl)bis(1-methoxy-2,3,5-trimethylbenzene) 
• 1621283-96-2 4,4’-((1E,3E,5E,7E,9E)-3,8-dimethyldeca-1,3,5,7,9-pentaene-1,10-diyl)bis(2,3,5-trimethylphenol) 
• 54350-48-0 etretinate 
• 61630-49-7 (2E,4E,6E,8E)-9-(4-methoxyl-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraen-1-ol 
• 58508-38-6 (2E,4E,6E,8E)-9-(4-methoxyl-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenal 
• 1621284-01-2 4,4’-((1E,3E,5E,7E,9E,11E,13E)-3,7,12-trimethyltetradeca-1,3,5,7,9,11,13-heptaene-1,14-diyl)bis(1-methoxy-2,3,5-trimethylbenzene) 
• 1621283-97-3 4,4’-((1E,3E,5E,7E,9E,11E,13E)-3,7,12-trimethyltetradeca-1,3,5,7,9,11,13-heptaene-1,14-diyl)bis(1-methoxy-2,3,5-trimethylphenol) 

Relevant articles and documents

Tailoring 3,3'-dihydroxyisorenieratene to hydroxystilbene: Finding a resveratrol analogue with increased antiproliferation activity and cell selectivity

Four novel compounds were designed by "tailoring" 3,3'-dihydroxyisorenieratene (a natural carotenoid) based on an isoprene unit retention truncation strategy. Among them, the smallest molecule 1 (2,3,6,2',3',6'-hexamethyl-4,4'-dihydroxy-trans-stilbene) was concisely synthesized in a one-pot Stille-Heck tandem sequence, and surfaced as a promising lead molecule in terms of its selective antiproliferative activity mediated by blocking the NCI-H460 cell cycle in G1 phase. Additionally, theoretical calculations and cell uptake experiments indicate that the unique polymethylation pattern of compound 1 significantly induces a conformational change shift out of planarity and increases its cell uptake and metabolic stability. The observation should be helpful to rationally design resveratrol-inspired antiproliferative agents. Four novel compounds were designed by "tailoring" 3,3'-dihydroxyisorenieratene (a natural carotenoid) based on an isoprene unit retention truncation strategy. Among them, the smallest molecule 1 was concisely synthesized by a one-pot Stille-Heck tandem sequence, and surfaced as a promising lead molecule in terms of its selective antiproliferative activity (see figure).

Syntheses, antiproliferative activity and theoretical characterization of acitretin-type retinoids with changes in the lipophilic part

Acitretin analogs, incorporating changes in the lipophilic part, were efficiently synthesized from commercially available aromatic aldehydes or methyl ketones using the Wittig or Horner-Wadsworth-Emmons reaction. Their antiproliferative activity was evaluated against human breast MCF-7 epithelial cells. Analogs 3, 4, 8 and 11 exhibited strong, dose-dependent, antiproliferative activity on the tested cell line. Analog 3, incorporating three methoxy groups in the aromatic ring, exhibited the strongest inhibitory effect at 10 μM. High-level all electron conventional ab initio and density functional theory quantum chemical calculations were performed to obtain the molecular structure, electron charge distribution and polarization properties of all compounds of interest in this work. The most active analogs were planar and were characterized by larger dipole moments than the other synthesized molecules. Another factor of importance to the analysis of the activity of these molecules is the dipole polarizability.