5273-88-1

Usage

Classification

Phenylpropanoid

Natural occurrence

Found in plants such as nutmeg and parsley

Psychoactive properties

Known for its psychoactive and hallucinogenic effects

Traditional uses

Medicinal and culinary purposes

Scent

Unique spicy and aromatic

Applications

Used in the production of perfumes, flavorings, and fragrances

Toxicity

Potential toxic effects, particularly in high doses

Harmful effects

Can be harmful if ingested in large quantities

Upstream product

• 557-31-3 3-ethoxyprop-1-ene 
• 114605-54-8 2,3,4-trimethoxyphenylmagnesium bromide 
• 450357-58-1 2-hydroxy-3,4-dimethoxyallylbenzene 
• 77-78-1 dimethyl sulfate 
• 5150-42-5 2,3-dimethoxyphenol 
• 106-95-6 allyl bromide 
• 74-88-4 methyl iodide 
• 380621-78-3 1-(allyloxy)-2,3-dimethoxybenzene 
• 10385-36-1 2,3,4-trimethoxybromobenzene 
• 24850-33-7 allyltributylstanane 
• 118062-05-8 2,3,4-trimethoxyphenylboronic acid 

Downstream Products

• 105591-36-4 2,3-Dihydro-6,7-dimethoxy-2-methylbenzofuran 
• 105591-37-5 1-(2'-Bromopropyl)-2,3,4-trimethoxybenzene 
• 5273-89-2 cis-2,3,4-Trimethoxy-1-propenyl-benzol 
• 5273-90-5 (E)-1,2,3-trimethoxy-4-(prop-1-en-1-yl)benzene 
• 1616515-32-2 C₂₀H₂₂O₅ 

Relevant academic research and scientific papers

Palladium-Catalyzed meta-C-H Olefination of Arene-Tethered Diols Directed by Well-Designed Pyrimidine-Based Group

The palladium-catalyzed meta-olefination of arene-tethered diols attached to a well-designed pyrimidine moiety is presented. Applications of the protocol are illustrated by the synthesis of various diol-based natural products, such as coumarins, phenylpropanoids, stilbenes, and chalcones. Advantages of this method are demonstrated through the easy removal of the template and a gram-scale olefination reaction. Finally, experimental verification, including 1H NMR, ESI-MS and IR, and DFT studies are undertaken to elucidate the mechanistic complexity.

Selective Claisen rearrangement and iodination for the synthesis of polyoxygenated allyl phenol derivatives

Allyl aryl ethers and allyl phenol derivatives were prepared starting from commercial or synthetized phenols. Either Williamson reaction or Et2AlCl catalyzed Claisen rearrangement was performed to obtain the polyoxygenated molecules. The pivotal allyl phenols were then modified by methylation, iodocyclization or electrophilic aromatic iodination to afford the polyoxygenated derivatives in good to excellent yields. Additionally, their antibacterial properties were also investigated against Gram-positive and Gram-negative bacteria.

Discovery of structurally simplified analogs of colchicine as an immunosuppressant

We have discovered a new class of colchicine-derived therapeutic agents for immune diseases including rejection of organ-transplantation and autoimmune disease. Compound 2, which had been developed to overcome poor pharmacokinetic properties of compound 1, a first-generation colchicine analog, turned out to show toxicity such as intestinal toxicity and loss of weight during in vivo tests. The deletion of 7-carboxamide group and middle ring-truncation in colchicine allowed us to have structurally simplified analogs with strong immunosuppressive activity. Herein, we report non-alkaloid tricyclic compound 7 and 12 as immunosuppressants which exhibited a strong immunosuppressive in vivo efficacy on the T-dependent antibody response, the Zymosan A-induced arthritis model and the Carrageenan-induced edema model. Compound 7 and 12 revealed less toxicity than the previous lead compound 2, and their minimum lethal doses (MLD) were proved to exceed 100 mg/kg.

STRUCTURE-ACTIVITY RELATIONSHIPS OF PHENYLPROPANOIDS AS GROWTH INHIBITORS OF THE GREEN ALGA SELENASTRUM CAPRICORNUTUM

Twenty-seven commercial or synthetic phenylpropanoids have been tested in broth against the unicellular alga Selenastrum capricornutum.The antialgal activity seems to be linked to the number as well as to the position of the methoxyl group in the molecule.A slight effect of the side chain substitution was also observed. Key Word Index - Selenastrum capricornutum; allelochemicals; phenylpropanoids.