p-methoxycinnamic acid methyl ester/para-methoxycinnamic acid methylester/4-Methoxybenzeneacrylic acid methyl ester/METHYL P-METHOXYCINNAMATE/4-methoxycinnamatemethylester/4-METHOXYCINNAMIC ACID METHYL ESTER/Cinnamate,methyl p-methoxy/methyl ester of p-methoxycinnamic acid
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provides coniferyl ferulate(CAS#:832-01-9) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate
The palladium metal catalysed Heck reaction of 4-iodoanisole with styrene or methyl acrylate has been studied in a continuous plug flow reactor (PFR) using supercritical carbon dioxide (scCO2) as the solvent, with THF and methanol as modifiers. The catalyst was 2% palladium on silica and the base was diisopropylethylamine due to its solubility in the reaction solvent. No phosphine co-catalysts were used so the work-up procedure was simplified and the green credentials of the reaction were enhanced. The reactions were studied as a function of temperature, pressure and flow rate and in the case of the reaction with styrene compared against a standard, stirred autoclave reaction. Conversion was determined and, in the case of the reaction with styrene, the isomeric product distribution was monitored by GC. In the case of the reaction with methyl acrylate the reactor was scaled from a 1.0 mm to 3.9 mm internal diameter and the conversion and turnover frequency determined. The results show that the Heck reaction can be effectively performed in scCO2 under continuous flow conditions with a palladium metal, phosphine-free catalyst, but care must be taken when selecting the reaction temperature in order to ensure the appropriate isomer distribution is achieved. Higher reaction temperatures were found to enhance formation of the branched terminal alkene isomer as opposed to the linear trans-isomer.
Heck; continuous flow; flow chemistry; palladium; supercritical carbon dioxide
Continuous-flow Heck synthesis of 4-methoxybiphenyl and methyl 4-methoxycinnamate in supercritical carbon dioxide expanded solvent solutions.
Lau PL1, Allen RW2, Styring P2.
2013 Dec 17
In vitro root cultures of Anigozanthos preissii and Wachendorfia thyrsiflora (Haemodoraceae) are suitable biological systems for studying the biosynthesis of phenylphenalenones. Here we report how we used these root cultures to investigate precursor-product relationships between phenylpropanoids and phenylphenalenones whose phenyl rings share identical substitution patterns. Four phenylpropanoic acids, including ferulic acid and the unusual 4-methoxycinnamic acid, were used in (13)C-labeled form as substrates to study their incorporation into phenylphenalenones. In addition to the previously reported 2-hydroxy-9-(4′-hydroxy-3′-methoxyphenyl)-1H-phenalen-1-one (trivial name musanolone F), 2-hydroxy-9-(4′-methoxyphenyl)-1H-phenalen-1-one (proposed trivial name 4′-methoxyanigorufone) was found as a biosynthetic product in A. preissii. The carbon skeleton of 4′-methoxycinnamic acid was biosynthetically incorporated as an intact unit including its 4′-O-methyl substituent at the lateral phenyl ring. 4′-Methoxyanigorufone is reported here for the first time as a natural product.
Copyright © 2015. Published by Elsevier Ltd.
Anigozanthos preissii; Biosynthesis; Haemodoraceae; Labeling; Nuclear magnetic resonance; Phenylphenalenones; Phenylpropanoids; Wachendorfia thyrsiflora
4-Methoxycinnamic acid--An unusual phenylpropanoid involved in phenylphenalenone biosynthesis in Anigozanthos preissii.
Hidalgo W1, Kai M1, Schneider B2.