3160-35-8

Usage

Uses

Used in Chemical Synthesis:
4-Hydroxybenzylideneacetone is used as a key intermediate in the synthesis of 4-(4-hydroxy-phenyl)-butan-2-one. This process involves the use of cyclohexane and AlCl3 as reagents, with CH2Cl2 serving as the solvent. 4-Hydroxybenzylideneacetone plays a crucial role in the production of various chemical products, contributing to the development of new materials and compounds with potential applications in different sectors.

InChI:InChI=1/C10H10O2/c1-8(11)2-3-9-4-6-10(12)7-5-9/h2-7,12H,1H3/b3-2+

Upstream product

• 123-08-0 4-hydroxy-benzaldehyde 
• 67-64-1 acetone 
• 106-96-7 propargyl bromide 
• 30802-00-7 4-coumaroyl-coenzyme A 
• 524-14-1 S-(hydrogen malonyl)coenzyme A 
• 87199-17-5 4-formylphenylboronic acid, 
• 67-63-0 isopropyl alcohol 
• 1439-36-7 1-triphenylphosphoranylidene-2-propanone 
• 71597-85-8 (p-hydroxyphenyl)boronic acid 
• 540-38-5 p-Iodophenol 
• 78-94-4 methyl vinyl ketone 
• 5471-51-2 4-(4-hydroxyphenyl)-2-oxobutane 

Downstream Products

• 24579-14-4 4'-Hydroxywarfarin 
• 79570-16-4 (E)-4-[4-((E)-3,7-Dimethyl-octa-2,6-dienyloxy)-phenyl]-but-3-en-2-one 
• 69617-84-1 rac-rhododendrol 
• 5471-51-2 4-(4-hydroxyphenyl)-2-oxobutane 
• 27911-81-5 1-(4-nitrophenyl)-5-(4-hydroxyphenyl)-1,4-pentadien-3-one 
• 15999-77-6 1-phenyl-5-(4-hydroxyphenyl)-1,4-pentadien-3-one 
• 518291-03-7 4-[4-(3-piperidinoproproxy)phenyl]but-3-en-2-one 

Relevant academic research and scientific papers

Novel penta-1,4-diene-3-one derivatives containing quinazoline and oxime ether fragments: Design, synthesis and bioactivity

A series of novel penta-1,4-diene-3-one derivatives containing quinazoline and oxime ether moieties were designed and synthesized. Their anticancer activities were evaluated by MTT assay, the results showed that most compounds exhibited extremely inhibitory effects against hepatoma SMMC-7721 cells. In particular, compounds Q2 and Q8 displayed the more potent inhibitory activity with IC50 values of 0.64 and 0.63 μM, which were better than that of gemcitabine (1.40 μM). Further mechanism studies indicated that compounds Q2, Q8, Q13 and Q19 could control the migration of SMMC-7721 cells effectively, and inhibit the proliferation of cancer cells by inhibiting the DNA replication. Western-blot results showed that compounds Q2 and Q8 induced irreversible apoptosis of SMMC-7721 cells by regulating the expression level of apoptose-related proteins. Those studies demonstrated that the penta-1,4-diene-3-one derivatives containing quinazoline and oxime ether fragments merited further research as potential anticancer agents.

8-Hydroxyquinolin-2(1H)-one analogues as potential β2-agonists: Design, synthesis and activity study

β2-Agonists that bind to plasmalemmal β2-adrenoceptors causing cAMP accumulation are widely used as bronchodilators in chronic respiratory diseases. Here, we designed and synthesized a group of 8-hydroxyquinolin-2(1H)-one analogues and studied their β2-agonistic activities with a cellular cAMP assay. Compounds B05 and C08 were identified as potent (EC50 2-agonists among the compounds tested. They behaved as partial β2-agonists in non-overexpressed HEK293 cells, and possessed rapid smooth muscle relaxant actions and long duration of action in isolated guinea pig tracheal strip preparations. In summary, B05 and C08 are β2-agonists with potential applicability in chronic respiratory diseases.

Selective oxidative hydroxylation of arylboronic acids by colloidal nanogold catalyzed in situ generation of H2O2 from alcohols under aerobic conditions

Selective hydroxylation of arylboronic acids was achieved through PVP (polyvinylpyrrolidone)-stabilized nanogold catalyzed in situ generated H2O2 formed by the oxidation of an alcoholic solvent under aerobic conditions. The synthetic application of in situ generated H2O2 was investigated through aerobic epoxidation of (E)-chalcone.

Coumaric acid derivatives as tyrosinase inhibitors: Efficacy studies through in silico, in vitro and ex vivo approaches

p-Coumaric acid is a known inhibitor of tyrosinase, an enzyme involved in the initial steps of the melanin synthesis in human and other species. However, its low lipophilicity impairs its penetration through skin and efficacy as antimelanogenic agent indeed. Accordingly, this paper reports the assessment of several coumaric acid derivatives as tyrosinase inhibitors and antimelanogenic agents in in vitro, in silico and ex vivo assays. The compounds were designed with modifications in the aromatic and acid moieties of p-coumaric acid, being the coumarate esters the most promising derivatives. The compounds showed higher tyrosinase inhibitory activity (pIC50 3.7–4.2) than the parent acid, being compounds 1d, 1e and 1f the most potent inhibitors. Docking analysis showed that these esters are competitive inhibitors per se, and act independently of a redox mechanism as suggested by DPPH assays. Moreover, the esters showed efficacy in reducing the melanin deposition in human skin fragments at 0.1% concentration, especially compound 1e. In summary, there is an important equilibria between tyrosinase affinity and lipophilicity that must be considered to get effective antimelanogenic agents with adequate permeability in the skin.

Synthesis and biological evaluation of myricetin-pentadienone hybrids as potential anti-inflammatory agents in vitro and in vivo

Some important pro-inflammatory cytokines such as interleukin-6, tumor necrosis factor-α and nitric oxide are thought to play key roles in the destruction of cartilage and bone tissue in joints affected by rheumatoid arthritis. In the present study, a series of new myricetin-pentadienone hybrids were designed and synthesized. Majority of them effectively inhibited the expressions liposaccharide-induced secretion of IL-6, TNF-α and NO in RAW264.7. The most prominent compound 5o could significantly decrease production of above inflammatory factors with IC50 values of 5.22 μM, 8.22 μM and 9.31 μM, respectively. Preliminary mechanism studies indicated that it could inhibit the expression of thioredoxin reductase, resulting in inhibiting of cell signaling pathway nuclear factor (N-κB) and mitogen-activated protein kinases. Significantly, compound 5o was found to effectively inhibit Freund's complete adjuvant induced rat adjuvant arthritis in vivo.

PROCESS FOR THE PREPARATION OF RACTOPAMINE HYDROCHLORIDE VIA NOVEL INTERMEDIATES

The present disclosure describes the new methods of preparation of Ractopamine which are superior to state of art by involving comparatively better and mild reaction conditions. The method of preparation involves following steps: In the first embodiment, 4-(4-hydroxyphenyl)-3-butene-2-one is prepared by condensation of 4-hydroxybenzaldehyde with acetone in the presence of sodium hydroxide/hydrochloric acid. In the next step, 4-(4-hydroxyphenyl)-3-butene-2-one undergoes hydrozination with 4-(-2-amino-1- hydroxyl ethyl) phenolhydrochloride in the presence of base using Pd/C/H2 as a catalyst in methanol/ethanol as solvent to yield Ractopamine base. In another embodiment, advancement over the previous scheme is use of Raney Ni/H2 instead of Pd/C as a catalyst. In yet another embodiment, 2-amino-1-(4-hydroxyphenyl) ethanone hydrochloride reacts with 4-(4-hydroxyphenyl)-butane -2-one in the presence of base and raney nickel/H2 as a catalyst. Compared to the prior art reports where Pd/C was used as a catalyst, Raney Ni is used in the present embodiment which is comparatively economical and better catalyst.

Use of a switchable-hydrophilicity solvent as both a solvent and a catalyst in aldol condensation

A switchable-hydrophilicity solvent, N,N-dimethylcyclohexylamine, was used as a recyclable catalyst and solvent for aldol condensation, giving >97% pure product in 94% isolated yield without the need for purification or additional solvents. CO2-triggered separation produced yields greater than conventional workup and allowed facile recycling of the amine.

Benzothiazole-containing 1,4-pentadiene-3-one derivative as well as preparation method and application thereof

The invention discloses a benzothiazole-containing 1,4-pentadienyl-3-one derivative, as well as a preparation method and application thereof. A general formula (I) is shown as the specification, wherein R is a phenyl group, a substituted phenyl or an aromatic heterocyclic group, the R-substituted phenyl group is one or more methyl or methoxy, trifluoromethyl, trifluoromethoxy, nitro, or one or more halogen atom-substituted phenyl group, and the R-substituted aromatic heterocyclic group is a thienyl group, a substituted naphthyl group or other heterocyclic groups. The benzothiazole-containing 1,4-pentadienyl-3-one derivative has relatively good resistance to tobacco mosaic virus, the reaction conditions are relatively mild, the post-treatment is simple, and the yield is relatively high.

A thioether of triazole containing 1, 4 - pentadiene -3 - ketone derivatives, preparation method and use thereof

The invention discloses a thioether of triazole containing 1, 4 - pentadiene - 3 - ketone derivatives, preparation method and use, its general structure is as follows, wherein: X is 2 - O or 4 - O, R is phenyl, substituted phenyl, heterocyclic base or 4 - methyl thiazole. The invention of tobacco mosaic virus, tobacco wilt bacteria in the dried bean curd is dry and rice pathogens and better control effect.

Pentadienone compound containing triazine, and preparation method and application of pentadienone compound

The invention relates to a pentadienone compound containing triazine, and a preparation method and an application of the pentadienone compound. The compound is shown as formula A as shown in the specification. X selected from O; R is phenyl, substituted phenyl or substituted heterocyclyl; R1 is a hydrogen atom or methoxyl; and R2 is phenyl, substituted phenyl or C1-C6 alkyl. The compound has a better prevention and control effect on pseudomonas solanacearum, xanthomonas citri and xanthomonas campestris pv. oryzae.