3160-35-8

Basic information

• Product Name: 4-Hydroxybenzylideneacetone
• Synonyms: 4-Hydroxybenzylideneacetone,97%;4-HYDROXYCINNAMOYLMETHANE;4-Hydroxystyrylmethyl ketone;Methyl 4-hydroxystyryl ketone;p-Hydoroxybenzalacetone;p-Hydroxystyrylmethyl ketone;4-Hydrobenzylideneacetone;Aids017763
• CAS NO: 3160-35-8
• Molecular Formula: C₁₀H₁₀O₂
• Molecular Weight: 162.19
• EINECS: 221-607-9
• Product Categories: Aromatic Ketones (substituted)
• Mol File: 3160-35-8.mol
• Article Data: 45

Chemical Properties

• Melting Point: 108-111°C
• Boiling Point: 318.1 °C at 760 mmHg
• Flash Point: 134.8 °C
• Appearance: /
• Density: 1.138 g/cm³
• Vapor Pressure: 0.000198mmHg at 25°C
• Refractive Index: 1.599
• Storage Temp.: Refrigerator
• Solubility: Optimally soluble in aqueous solvents.
• PKA: 9.88±0.26(Predicted)
• BRN: 2412544
• CAS DataBase Reference: 4-Hydroxybenzylideneacetone(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Hydroxybenzylideneacetone(3160-35-8)
• EPA Substance Registry System: 4-Hydroxybenzylideneacetone(3160-35-8)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-37
• TSCA: Yes
• Hazardous Substances Data: 3160-35-8(Hazardous Substances Data)

Usage

Uses

4-Hydroxybenzylideneacetone is used in the synthesis of 4-(4-hydroxy-phenyl)-butan-2-one. This reaction needs the reagents of cyclohexane and AlCl3, and the solvent of CH2Cl2.

Definition

ChEBI: An enone in which a 4-hydroxyphenyl group is attached to the beta-carbon atom of but-3-en-2-one.

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

Downstream Products

• 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 
• 518291-03-7 4-[4-(3-piperidinoproproxy)phenyl]but-3-en-2-one 

Relevant articles and documents

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.

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.

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.