98886-30-7

Upstream product

• 1134-87-8 3-benzyl-pentane-2,4-dione 
• 121-33-5 vanillin 

Downstream Products

• 98886-16-9 Acetic acid 4-[(1E,3Z,6E)-7-(4-acetoxy-3-methoxy-phenyl)-4-benzyl-3-hydroxy-5-oxo-hepta-1,3,6-trienyl]-2-methoxy-phenyl ester 

Relevant academic research and scientific papers

Electron ionization mass spectrometry of curcumin analogues: An olefin metathesis reaction in the fragmentation of radical cations

The natural compound curcumin, used in cosmetics, traditional medicines and as a spice in food, is known as a multi-factorial anti-inflammatory agent. To study the anti-inflammatory activity of curcumin derivatives, 24 analogues were synthesized and their structures were confirmed by 1H NMR and electron ionization (EI) mass spectrometry. Most signals in the EI mass spectra can be attributed to commonly known fragmentations, but the formation of ring-substituted 1,2-diphenylethene (stilbene)-type radical cations, observed in the spectra of all compounds investigated and resulting in the base peak for some compounds, requires a peculiar rearrangement. Metastable ion spectra and 13C labelling studies show that the stilbene-type ions are formed directly from the molecular ions and contain the two original aryl groups and the 1 and 7 carbon atoms of the olefinic system. It is proposed that the formation of stilbene-type ions results from an intramolecular olefin metathesis reaction; this suggestion is supported by semi-empirical (MNDO/PM3) calculations.

Synthesis of Naturally Occuring Curcuminoids and Related Compounds

Six known naturally occuring curcuminoids like curcumin, and 31 other analogs (Scheme 1) have been synthesized.Among them, 25 curcuminoids were prepared by condensing different substituted 2,4-pentanediones and benzaldehydes.The boron complex 12 has been used to avoid Knoevenagel condensation at C-3 of 2,4-pentanedione.Some curcuminoids containing hydroxy groups in the aromatic moiety have been acylated.Alkylation of the tetrabutylammonium salt of 5-hydroxy-1,7-diphenyl-1,4,6-heptatrien-3-one (1a) by benzyl bromide gave only C-alkylated 4-benzyl-1,7-diphenyl-1,6-heptadiene-3,5-dione (1d*).The 13C NMR data, the UV absorptions, and the tautomerism of the curcuminoids are discussed.