19753-63-0

Upstream product

• 603-35-0 triphenylphosphine 
• 17157-48-1 bromoacetaldehyde 

Downstream Products

• 94579-37-0 Triphenylphosphin-brom-formyl-methylen 
• 121525-75-5 4(S)-benzoyloxy-2(E),6(Z),9(Z)-pentadecatrienal 
• 129414-18-2 4(R)-benzoyloxy-2(E),6(Z),9(Z)-pentadecatrienal 
• 2136-75-6 (triphenylphosphoranylidene)acetaldehyde 

Relevant academic research and scientific papers

Stereoselective synthesis of (6Z,8E)-undeca-6,8,10-trien-3-one (yuzunone) for its characterization in yuzu and various citrus essential oils

(6Z,8E)-Undeca-6,8,10-trien-3-one (yuzunone) is reported to be one of the main olfactory contributors of the specific fruity-green-balsamic odor of yuzu peel oil. Using an original stereoselective synthesis, we prepared a pure sample of yuzunone, which was used as a reference compound to check its presence by GC–MS and GC–O in 5 commercial samples of yuzu and citrus essential oils. Surprisingly, we could not detect yuzunone by GC–MS in any of our samples. However, it could be detected by a small part of the panelists involved in GC–O/AEDA experiments in a yuzu commercial oil, but its olfactory contribution proved to be very limited.

Substituted dienes prepared from betulinic acid – Synthesis, cytotoxicity, mechanism of action, and pharmacological parameters

A set of new substituted dienes were synthesized from betulinic acid by its oxidation to 30-oxobetulinic acid followed by the Wittig reaction. Cytotoxicity of all compounds was tested in vitro in eight cancer cell lines and two noncancer fibroblasts. Almost all dienes were more cytotoxic than betulinic acid. Compounds 4.22, 4.30, 4.33, 4.39 had IC50 below 5 μmol/L; 4.22 and 4.39 were selected for studies of the mechanism of action. Cell cycle analysis revealed an increase in the number of apoptotic cells at 5 × IC50 concentration, where activation of irreversible changes leading to cell death can be expected. Both 4.22 and 4.39 led to the accumulation of cells in the G0/G1 phase with partial inhibition of DNA/RNA synthesis at 1 × IC50 and almost complete inhibition at 5 × IC50. Interestingly, compound 4.39 at 5 × IC50 caused the accumulation of cells in the S phase. Higher concentrations of tested drugs probably inhibit more off-targets than lower concentrations. Mechanisms disrupting cellular metabolism can induce the accumulation of cells in the S phase. Both compounds 4.22 and 4.39 trigger selective apoptosis in cancer cells via intrinsic pathway, which we have demonstrated by changes in the expression of the crucial apoptosis-related protein. Pharmacological parameters of derivative 4.22 were superior to 4.39, therefore 4.22 was the finally selected candidate for the development of anticancer drug.

Preparation method of (formylmethylene) triphenyl orthophosphonium

The invention discloses a preparation method of (formylmethylene) triphenyl orthophosphonium, and relates to the technical field of chemical substance preparation. The preparation method specificallycomprises the following steps of: carrying out a hydrolysis reaction on 2-bromo-1,1-dimethoxyethane under an acidic condition to obtain 1-bromoacetaldehyde; reacting 1-bromoacetaldehyde with triphenylphosphine to obtain a transition state intermediate quaternary phosphine salt namely 2-aldehyde ethyl triphenylphosphine bromide; and adding alkali into an aprotic solvent to obtain a product namely (formylmethylene) triphenyl orthophosphonium by losing one molecule of hydrogen bromide. The preparation method provided by the invention has the advantages of short synthesis route, easy synthesis, simple operation, cheap and easily obtained raw materials, less side reactions, high yield and high purity of the prepared (formylmethylene) triphenyl orthophosphonium, and is suitable for industrial production.