54757-47-0

Basic information

• Product Name: 4-(4-METHOXY-2,3,6-TRIMETHYLPHENYL)-BUT-3-EN-2-ONE
• Synonyms: 4-(4-METHOXY-2,3,6-TRIMETHYLPHENYL)-BUT-3-EN-2-ONE;(E)-4-(4-METHOXY-2,3,6-TRIMETHYL-PHENYL)-BUT-3-EN-2-ONE;CHEMBRDG-BB 5229800;4-(4-Methoxy-2,3,6-trimethylphenyl)
• CAS NO: 54757-47-0
• Molecular Formula: C₁₄H₁₈O₂
• Molecular Weight: 218.29
• Mol File: 54757-47-0.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 358.7°C at 760 mmHg
• Flash Point: 156.7°C
• Appearance: /
• Density: 1.006g/cm³
• Vapor Pressure: 2.49E-05mmHg at 25°C
• Refractive Index: 1.539
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 4-(4-METHOXY-2,3,6-TRIMETHYLPHENYL)-BUT-3-EN-2-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(4-METHOXY-2,3,6-TRIMETHYLPHENYL)-BUT-3-EN-2-ONE(54757-47-0)
• EPA Substance Registry System: 4-(4-METHOXY-2,3,6-TRIMETHYLPHENYL)-BUT-3-EN-2-ONE(54757-47-0)

Safety Data

• Hazardous Substances Data: 54757-47-0(Hazardous Substances Data)

Usage

General Description

4-(4-Methoxy-2,3,6-trimethylphenyl)-but-3-en-2-one, also known as piperonal, is an organic compound commonly used as a fragrance in perfumes and as a flavoring agent in the food industry. It is found naturally in certain plant extracts and is also synthetically produced for commercial use. Piperonal has a pleasant, sweet, and floral aroma, making it a popular ingredient in cosmetic and food products. However, it is important to note that piperonal is also used as a precursor in the illicit production of the drug MDMA, and it is regulated in some countries due to its potential for abuse.

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

Upstream product

• 54344-92-2 2,3,6-trimethyl-4-methoxy-benzaldehyde 
• 67-64-1 acetone 
• 697-82-5 2,3,5-trimethylphenol 
• 20469-61-8 2,3,5-trimethylanisole 

Downstream Products

• 167637-41-4 ethyl 3-methyl-5-(4'-methoxy-2',3',6'-trimethylphenyl)-2,4-pentadienoate 
• 1228174-61-5 4-(2,3,6-trimethyl-4-methoxyphenyl)-6-methyl-3,4-dihydropyrimidin-2(1H)-thione 
• 74479-40-6 butyl {(2E,4E,6E,8E)-9-(4-methoxy-2,3,6-trimethyl)phenyl-3,7-dimethylnona-2,4,6.8}tetraenoate 
• 54757-44-7 5-(4-methoxy-2,3,6-trimethylphenyl)-3-methylpenta-2,4-diene-1-triphenylphosphonium bromide 
• 54757-46-9 acitretin 
• 54757-48-1 5-(4-methoxy-2,3,6 trimethylphenyl)-3-methylpenta-1,4-dien-3-ol 
• 57399-31-2 trans-9-(4-Methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6-nonatriensaeure 
• 62924-21-4 trans-5-(4-Methoxy-2,3,6-trimethylphenyl)-3-methyl-2-pentensaeureethylester 
• 62924-22-5 trans-5-(4-Methoxy-2,3,6-trimethylphenyl)-3-methyl-2-pentenal 
• 57399-34-5 trans-5-(4-Methoxy-2,3,6-trimethylphenyl)-3-methyl-2-penten-1-ol 
• 419534-29-5 cis,cis-5-(4'-methoxy-2',3',6'-trimethylphenyl)-3-methylpenta-2,4-dienal 
• 167637-42-5 5-(4'-methoxy-2',3',6'-trimethylphenyl)-3-methylpenta-2,4-dienol 
• 69877-38-9 5-(4-methoxy-2,3,6-trimethylphenyl)-3-methyl-2(E),4(E)-pentadien-1-al 
• 57399-32-3 4-(4-methoxy-2,3,6-trimethylphenyl)butan-2-one 

Relevant articles and documents

PROCESS FOR PREPARATION OF ACITRETIN

The present invention provides a process for preparation of {(2E,4E,6E,8E)-9-(4-methoxy-2,3,6- trimethyl)phenyl-3,7-dimethyl-nona-2,4,6,8}tetraenoate, an acitretin intermediate of formula (VI) with trans isomer ≥97%, comprising of reacting 3-formyl-crotonic acid butyl ester of formula (V), substantially free of impurities, with 5-(4-methoxy-2,3,6-trimethylphenyl)-3- methyl-penta-2,4-diene-l-triphenyl phosphonium bromide of formula (IV) and isolating resultant compound of formula (VI), treating the filtrate with iodine for isomerization of the undesired cis intermediate and finally obtaining acitretin (I), with desired trans isomer ≥97%.

Evaluation of retinoid lactones as topical therapeutic agents in dermatology

Purpose. Optimization of the therapeutic ratio of analogs of the topically active 11-cis,13-cis-12-hydroxymethylretinoic acid, δ-lactone (I) relative to antihyperproliferation and antihyperkeratinization vs. toxicity. Methods. Nine analogs of 1, in which variations were made in the lipophilic cyclohexenyl moiety or in the lactone ring, were evaluated for topical activity against hyperkeratinization, inhibition of TPA-induced DNA synthesis and for skin irritation. Results. Although more potent lactones than the parent lactone 1 were identified, none possessed the favorable therapeutic ratio associated with 1. Conclusions. The δ-lactone 1 possesses unique molecular features responsible for its desirable therapeutic ratio as an anti-hyperproliferative and antihyperkeratotic agent. In view of its very low systemic retinoid toxicity and the absence of any systemic toxicity, this lactone may be a good candidate for use in the topical treatment of acne.