64417-10-3

Upstream product

• 53463-68-6 1-bromo-10-decanol 
• 603-35-0 triphenylphosphine 
• 112-47-0 1,10-Decanediol 
• 51795-88-1 1-bromo-10-(tetrahydropyranyloxy)decane 

Downstream Products

• 64437-44-1 (E)-10-Pentadecen-1-ol 
• 64437-42-9 (10Z)-10-pentadecen-1-ol 
• 64437-32-7 (E)-10-tridecen-1-ol 
• 64437-31-6 (Z)-10-tridecen-1-ol 
• 120677-73-8 (10-bromodecyl)triphenylphosphonium bromide 
• 1401526-76-8 C₃₄H₅₄O₂Si 
• 1401526-83-7 C₃₄H₅₆O₂Si 
• 64437-48-5 Δ10-hexadecenol 
• 1581234-54-9 triphenyl (10-((3,4,5-trihydroxybenzoyl)oxy)decyl)phosphonium bromide 
• 56218-70-3 (Z)-10-hexadecenyl acetate 
• 64437-45-2 Acetic acid (E)-pentadec-10-enyl ester 
• 64437-43-0 Z-10-pentadecenyl acetate 
• 86416-30-0 (E/Z)-10-hexadecen-1-ol 

Relevant academic research and scientific papers

A novel selective mitochondrial-targeted curcumin analog with remarkable cytotoxicity in glioma cells

Naturally occurring polyphenol curcumin (4) or demethoxycurcumin (5) and their synthetic derivatives display promising anticancer activities. However, their further development is limited by low bioavailability and poor selectivity. Thus, a mitochondria-targeted compound 14 (DMC-TPP) was prepared in the present study by conjugating a triphenylphosphine moiety to the phenolic hydroxyl group of demethoxycurcumin to enhance its bioavailability and treatment efficacy. The in vitro biological experiments of DMC-TPP showed that it not only displayed higher cytotoxicity as compared with its parent compound 5, but also exhibited superior mitochondria accumulation ability. Glioma cells were more sensitive to DMC-TPP, which inhibited the proliferation of U251 cells with an IC50 of 0.42 μM. The mechanism studies showed that DMC-TPP triggers mitochondria-dependent apoptosis, caused by caspase activation, production of reactive oxygen species (ROS) and decrease of mitochondrial membrane potential (MMP). In addition, DMC-TPP efficiently inhibited cellular thioredoxin reductase, which contributed to its cytotoxicity. Significantly, DMC-TPP delayed tumor progression in a mouse xenograft model of human glioma cancer. Taken together, the potent in vitro and in vivo antitumor activity of DMC-TPP warrant further comprehensive evaluation as a novel anti-glioma agent.

Industrial synthesis method of dichocrocis punctiferalis sex pheromone

The invention belongs to the field of chemical synthesis, and particularly relates to an industrial synthesis method of a dichocrocis punctiferalis sex pheromone. The method comprises the following steps: taking 1, 10-decanediol as a raw material; carrying out a single-side bromination reaction to prepare 10-bromodecanol; then reacting the 10-bromodecanol with triphenylphosphine to obtain 10-hydroxydecyltriphenylphosphine salt; performing a Wittig reaction with n-hexaldehyde under the action of alkali to obtain cis-based 10-hexadecene-1-ol; performing isomerization on the cis-based enol underthe action of p-methylthiophenol to obtain trans-based 10-hexadecene-1-ol; and finally performing oxidation under the action of an oxidant to obtain the final product 10-hexadecenal. The method is mild in reaction condition and suitable for large-scale production.

Continuous flow synthesis of lipophilic cations derived from benzoic acid as new cytotoxic chemical entities in human head and neck carcinoma cell lines

Continuous flow chemistry was used for the synthesis of a series of delocalized lipophilic triphenylphosphonium cations (DLCs) linked by means of an ester functional group to several hydroxylated benzoic acid derivatives and evaluated in terms of both reaction time and selectivity. The synthesized compounds showed cytotoxic activity and selectivity in head and neck tumor cell lines. The mechanism of action of the molecules involved a mitochondrial uncoupling effect and a decrease in both intracellular ATP production and apoptosis induction. This journal is

Novel benzoate-lipophilic cations selectively induce cell death in human colorectal cancer cell lines

Introduction: Colorectal cancer (CRC) is a critical health issue worldwide. The high rate of liver and lung metastasis associated with CRC creates a significant barrier to effective and efficient therapy. Tumour cells, including CRC cells, have metabolic alterations, such as high levels of glycolytic activity, increased cell proliferation and invasiveness, and chemo- and radio-resistance. However, the abnormally elevated mitochondrial transmembrane potential of these cells also provides an opportunity to develop drugs that selectively target the mitochondrial functions of tumour cells. Methods: In this work, we used a new batch of benzoic acid esters with cytotoxic activities attached to the triphenylphosphonium group as a vehicle to target tumour mitochondria and improve their activity. We evaluated the cytotoxicity, selectivity, and mechanism of action of these derivatives, including the effects on energy stress-induced apoptosis and metabolic behaviour in the human CRC cell lines HCT-15 and COLO-205. Results: The benzoic acid derivatives selectively targeted the tumour cells with high potency and efficacy. The derivatives induced the uncoupling of the oxidative phosphorylation system, decreased the transmembrane potential, and reduced ATP levels while increasing AMPK activation, thereby triggering tumour cell apoptosis in both tumour cell lines tested. Conclusion: The benzoic acid derivatives studied here are promising candidates for assessing in vivo models of CRC, despite the diverse metabolic characteristics of these tumour cells.

Antiproliferative and uncoupling effects of delocalized, lipophilic, cationic gallic acid derivatives on cancer cell lines. Validation in vivo in singenic mice

Tumor cells principally exhibit increased mitochondrial transmembrane potential (Δψm) and altered metabolic pathways. The therapeutic targeting and delivery of anticancer drugs to the mitochondria might improve treatment efficacy. Gallic acid e

Molecular design, synthesis, and evaluation of novel potent apoptosis inhibitors inspired from bongkrekic acid

Bongkrekic acid (BKA) is an inhibitor of adenine nucleotide translocase (ANT). Since inhibition of ANT is connected to the inhibition of cytochrome c release from mitochondria, which then results in the suppression of apoptosis, it has been used as a tool for the mechanistic investigation of apoptosis. BKA consists of a long carbon chain with two asymmetric centers, a nonconjugated olefin, two conjugated dienes, three methyl groups, a methoxyl group, and three carboxylic acids. This complicated chemical structure has caused difficulties in synthesis, supply, and biochemical mechanistic investigations. In this study, we designed and synthesized more simple tricarboxylic acids that were inspired by the molecular structure of BKA. Their cytotoxicity and apoptosis-preventing activity in HeLa cells and the effect on the mitochondrial inner membrane potential (Δψm) in HL-60 cells were then evaluated. All tested tricarboxylic acid derivatives including BKA showed little toxicity against HeLa cells. BKA and two of the synthesized derivatives significantly suppressed staurosporine (STS)-induced reductions in cell viability. Furthermore, STS-induced Δψm collapse was significantly restored by pretreatment with BKA and a tricarboxylic acid derivative. Other derivatives, in which one of three carboxylic acids was esterified, exhibited potent toxicity, especially a derivative bearing a carbon chain of the same length as that of BKA. In conclusion, we have developed a new lead compound as an apoptosis inhibitor bearing three carboxylic acids connected with the proper length of a long carbon chain.

Phosphonioalkylthiosulfate zwitterions - New masked thiol ligands for the formation of cationic functionalised gold nanoparticles

We report the synthesis and structural characterisation of a new family of stable phosphonioalkylthiosulfate zwitterions, R3P +(CH2)nS2O3- (R = Ph or Bu, n = 3,4,6, 8 or 10) which behave as cationic masked thiolate ligands with applications in the functionalisation of gold nanoparticles, having potential as new diagnostic biorecognition systems. The ligands were prepared by treatment of ω-bromoalkylphosphonium salts with sodium thiosulfate. The crystal and molecular structures of the zwitterions (R = Ph, n = 3) and (R = Bu, n = 3) were determined. A series of phosphonioalkanethiolate-capped gold nanoparticles dispersed in water was prepared by borohydride reduction of potassium tetrachloroaurate in the presence of the zwitterions in a dichloromethane-water system. UV-visible spectroscopy and scanning transmission electron-microscopy indicated that capped nanoparticles of ca. 5 nm diameter were present. The Royal Society of Chemistry 2006.

Biosynthesis of iso-fatty acids in myxobacteria

The fatty acid (FA) profiles of the myxobacteria Stigmatella aurantiaca and Myxococcus xanthus were investigated by acidic methanolysis of total cell extracts and GC or GC-MS analysis. The main components were 13- methyltetradecanoic acid (iso-15:0) and (Z)-hexadec-11-enoic acid (16:1, ω-5 cis). The biosynthesis of iso-FAs was investigated in several feeding experiments. Feeding of isovaleric acid (IVA) to a mutant impaired in the degradation of leucine to isovaleryl-CoA (IV-CoA) (bkd mutant) of M. xanthus only increased the amount of iso-odd FAs, whereas feeding of isobutyric acid (IBA) gave increased amounts only of iso-even FAs. In contrast, a bkd mutant of S. aurantiaca gave increased amounts of iso-odd and iso-even fatty acids in both experiments. We assumed that in S. aurantiaca α-oxidation takes place. [D7]-15-Methylhexadecanoic acid (8) was synthesised and fed to S. aurantiaca as well as [D10]leucine and [D8]valine to elucidate this pathway in more detail. The iso-fatty acid 8 was degraded by α- and β-oxidation steps. [D10]Leucine was strongly incorporated into iso-odd and iso-even fatty acids, whereas the incorporation rates for [D8]valine into both types of fatty acids were low. Thus α-oxidation plays an important role in the biosynthesis of iso-fatty acids in S. aurantiaca. The incorporation rates observed after feeding of [D 10]leucine and [D8]valine are the highest for iso-17:0 compared to the other acids. This indicates the central role of iso-17:0 in the biosynthesis of iso-FAs. The shorter homologues seem to be formed mainly by α-oxidation and β-oxidation of this acid. After feeding of 8 traces of unsaturated counterparts of this labelled FA occurred in the extracts indicating that desaturases are active in the biosynthesis of unsaturated fatty acids in S. aurantiaca. The Royal Society of Chemistry 2005.

An efficient method for the synthesis of enantiopure ω-amino acids with proteinogenic side chains

An efficient method for the synthesis of enantiopure ω-amino acids with proteinogenic side chains, starting from the corresponding natural α-amino acids, was developed. N-Protected amino aldehydes, obtained from the corresponding amino alcohols by oxidati

The synthesis of β-keto lactones via cyclization of β-keto ester dianions or the cyclization of Meldrum's acid derivatives

Two new methods to synthesize macrocyclic β-keto lactones have been developed.The first involves the synthesis of ω-halo-β-keto esters and an intramolecular alkylation of the dianions to these compounds.The reaction is complicated by elimination in the small and medium ring systems and by difficulties in purifying the final products.However, it is possible to obtain modest yields of the desired β-keto lactones.This procedure was used to synthesize the 25- and 27-membered ring β-hydroxy lactones that are the constituents of termite defense compounds.The second method involves the thermolysis of acylated Meldrum's acid derivatives, which leads directly to β-keto lactones.This process gives modest yields of macrocyclic systems and good yield of the unsubstituted 3-oxopentan-5-olide (25) .The 14-membered macrocyclic β-keto lactone 9j has a complex 1H NMR spectrum, which has been interpreted in terms of multiple conformations.The temperature dependence of the NMR spectrum of 9j is consistent with entropic, rather than enthalpic, control of the equilibrium.Quasiharmonic entropy calculations are consistent with this model.