62924-31-6

Basic information

• Product Name: (E)-(4-methoxy-2,3,6-trimethylphenyl)-3-buten-2-one
• Synonyms: (E)-(4-methoxy-2,3,6-trimethylphenyl)-3-buten-2-one;(E)-4-(2,3,6-Trimethyl-4-methoxyphenyl)-3-butene-2-one;(E)-4-(4-Methoxy-2,3,6-trimethylphenyl)-3-buten-2-one;(4-Methoxy-2,3,6-triMethylphenyl)-3-buten-2-one
• CAS NO: 62924-31-6
• Molecular Formula: C₁₄H₁₈O₂
• Molecular Weight: 218.29152
• EINECS: 263-760-4
• Mol File: 62924-31-6.mol

Chemical Properties

• Boiling Point: 347.4oC at 760 mmHg
• Flash Point: 149.1oC
• Appearance: /
• Density: 1.006
• Vapor Pressure: 5.4E-05mmHg at 25°C
• Refractive Index: 1.51
• CAS DataBase Reference: (E)-(4-methoxy-2,3,6-trimethylphenyl)-3-buten-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-(4-methoxy-2,3,6-trimethylphenyl)-3-buten-2-one(62924-31-6)
• EPA Substance Registry System: (E)-(4-methoxy-2,3,6-trimethylphenyl)-3-buten-2-one(62924-31-6)

Safety Data

• Hazardous Substances Data: 62924-31-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C14H18O2/c1-6-12(15)8-13-9(2)7-14(16-5)11(4)10(13)3/h6-7H,1,8H2,2-5H3

Upstream product

• 154406-54-9 4-(4-methoxy-2,3,6-trimethylphenyl)-3-bromobutan-2-one 
• 20469-61-8 2,3,5-trimethylanisole 
• 697-82-5 2,3,5-trimethylphenol 
• 5469-19-2 1-bromo-2,4,5-trimethylbenzene 
• 154406-43-6 3-(2,5-dimethyl-4-methoxybenzoyl)-2-methylpropanoic acid 
• 154406-44-7 4-(2,5-dimethyl-4-methoxy-1-phenylyl)-2-methylbutanoic acid 
• 54344-92-2 2,3,6-trimethyl-4-methoxy-benzaldehyde 
• 67-64-1 acetone 
• 1706-11-2 2,5-Dimethyl-anisol 
• 154406-46-9 7-methoxy-2,5,8-trimethyl-1-tetralol 
• 154406-47-0 7-methoxy-2,5,8-trimethyl-3,4-dihydronaphthalene 
• 154406-45-8 7-methoxy-2,5,8-trimethyl-1-tetralone 
• 57399-32-3 4-(4-methoxy-2,3,6-trimethylphenyl)butan-2-one 
• 154152-57-5 4-bromo-3-nitro-1,2,5-trimethylbenzene 

Downstream Products

• 69877-39-0 (2Z,4E)-5-(4-methoxy-2,3,6-trimethylphenyl)-3-methylpenta-2,4-dienal 
• 69877-38-9 5-(4-methoxy-2,3,6-trimethylphenyl)-3-methyl-2(E),4(E)-pentadien-1-al 
• 419534-28-4 (2E,4E)-5-(4-Methoxy-2,3,6-trimethyl-phenyl)-3-methyl-penta-2,4-dien-1-ol 
• 419534-27-3 (2E,4E)-5-(4-Methoxy-2,3,6-trimethyl-phenyl)-3-methyl-penta-2,4-dienoic acid methyl ester 
• 70573-55-6 2-((1E,3E)-5-Benzenesulfonyl-3-methyl-penta-1,3-dienyl)-5-methoxy-1,3,4-trimethyl-benzene 
• 57399-32-3 4-(4-methoxy-2,3,6-trimethylphenyl)butan-2-one 
• 102996-47-4 Methyl₇-(4-Methoxy-2,3,6-trimethylphenyl)-5-Methyl-Hepta-2,4,6-Trienoate 
• 1269259-99-5 (2E,4E)-ethyl 5-(-4-methoxy-2,3,6-trimethylphenyl)-3-methylpenta-2,4-dienoate 
• 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) 

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).

A new stereoselective synthesis of acitretin (=Soriatane, Neotigason)

A new synthesis of acitretin via a C15 + C5 route is reported. The C15 unit is the key step, involving a procedure that provides the required (all-E)-C15-aldehyde with high stereoselectivity.

STEREOSELECTIVE SYNTHESIS OF 5-ARYL-3-METHYL-2E,4E-PENTADIENALS

A series of 5-aryl-3-methyl-2E,4E-pentadienals were synthesized stereoselectively from 4-aryl-3E-buten-2-ones and methylmagnesium iodide followed by formylation of the obtained tertiary dimethylstyrylcarbinols by the formylating complex produced from dimethylformamide and phosphorus oxychloride.A synthesis of 2,3,6-trimethyl-4-methoxybenzaldehyde, starting from pseudocumene, is proposed.

Synthesis of 4-(4-methoxy-2,3,6-trimethylphenyl)-3-buten-2-one, a key synthon for etretinate and its metabolites

A synthetic route to 4-(4-methoxy-2,3,6-trimethylphenyl)-3-buten-2-one (2), a valuable synthon to etretinate (1), a potent antipsoriatic drug is described.The keto acids (3a) and (3b) obtained from 2,5-dimethylanisole by acylation with methylsuccinic and succinic anhydrides, respectively are elaborated separately to the identical methoxytrimethyldihydronaphthalene (7a) which on ozonolysis furnishes the ring opened arylketoaldehyde (8).Strategic manipulation of the keto and aldehyde functions of 8 leads to the arylbutanone (14).Side chain bromination of 14 gives the bromoketone (15) which provides on dehydrobromination the key synthon (2).