22568-49-6

Basic information

• Product Name: TRANS-4-HYDROXY-BETA-NITROSTYRENE 97
• Synonyms: TRANS-4-HYDROXY-BETA-NITROSTYRENE 97;trans-4-hydroxy-β-nitrostyrene;1-Hydroxy-4-(2-nitrovinyl)benzene, 2-(4-Hydroxyphenyl)nitroethene, trans-4-(2-Nitrovinyl)phenol;4-(2-nitroethenyl)phenol;(E)-4-(2-Nitrovinyl)phenol;Trans-p-hydroxy-beta-nitrostyrene;trans-4-Hydroxy-beta-nitrostyrene 97%
• CAS NO: 22568-49-6
• Molecular Formula: C₈H₇NO₃
• Molecular Weight: 165.147
• Mol File: 22568-49-6.mol
• Article Data: 31

Chemical Properties

• Melting Point: 167-171 °C(lit.)
• Boiling Point: 318.3±17.0 °C(Predicted)
• Appearance: /
• Density: 1.320±0.06 g/cm3(Predicted)
• PKA: 8.04±0.13(Predicted)
• CAS DataBase Reference: TRANS-4-HYDROXY-BETA-NITROSTYRENE 97(CAS DataBase Reference)
• NIST Chemistry Reference: TRANS-4-HYDROXY-BETA-NITROSTYRENE 97(22568-49-6)
• EPA Substance Registry System: TRANS-4-HYDROXY-BETA-NITROSTYRENE 97(22568-49-6)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• Hazardous Substances Data: 22568-49-6(Hazardous Substances Data)

Upstream product

• 7400-08-0 p-Coumaric Acid 
• 878-00-2 4-formylphenyl acetate 
• 75-52-5 nitromethane 
• 123-08-0 4-hydroxy-benzaldehyde 
• 625-75-2 nitroacetic acid 

Downstream Products

• 95834-26-7 6-Amino-5-[1-(4-hydroxy-phenyl)-2-nitro-ethyl]-1,3-dimethyl-1H-pyrimidine-2,4-dione 
• 22568-50-9 4-(2-Nitrovinyl)benzoic acid methyl ester 
• 51-67-2 tyrosamine 
• 7400-08-0 p-Coumaric Acid 

Relevant articles and documents

Biological evaluation and SAR analysis of novel covalent inhibitors against fructose-1,6-bisphosphatase

Fructose-1,6-bisphosphatase (FBPase) is an attractive target for affecting the GNG pathway. In our previous study, the C128 site of FBPase has been identified as a new allosteric site, where several nitrovinyl compounds can bind to inhibit FBPase activity. Herein, a series of nitrostyrene derivatives were further synthesized, and their inhibitory activities against FBPase were investigated in vitro. Most of the prepared nitrostyrene compounds exhibit potent FBPase inhibition (IC50 3, CF3, OH, COOH, or 2-nitrovinyl were installed at the R2 (meta-) position of the benzene ring, the FBPase inhibitory activities of the resulting compounds increased 4.5–55 folds compared to those compounds with the same groups at the R1 (para-) position. In addition, the preferred substituents at the R3 position were Cl or Br, thus compound HS36 exhibited the most potent inhibitory activity (IC50 = 0.15 μM). The molecular docking and site-directed mutation suggest that C128 and N125 are essential for the binding of HS36 and FBPase, which is consistent with the C128-N125-S123 allosteric inhibition mechanism. The reaction enthalpy calculations show that the order of the reactions of compounds with thiol groups at the R3 position is Cl > H > CH3. CoMSIA analysis is consistent with our proposed binding mode. The effect of compounds HS12 and HS36 on glucose production in primary mouse hepatocytes were further evaluated, showing that the inhibition was 71% and 41% at 100 μM, respectively.

NITROALKENE NON STEROIDAL ANTI-INFLAMMATORY DRUGS (NA-NSAIDS) AND METHODS OF TREATING INFLAMMATION RELATED CONDITIONS

Nitroalkene non-steroidal anti-inflammatory compounds, pharmaceutical compositions thereof, and methods of treating inflammation related conditions.

Iodine monobromide catalysed regioselective synthesis of 3-arylquinolines from α-aminoacetophenones and: Trans -β-nitrostyrenes

A simple and efficient method for regioselective synthesis of 3-arylquinolines is described from α-aminoacetophenones and trans-β-nitrostyrenes using 20 mol% iodine monobromide as a catalyst in acetonitrile solvent at 80 °C. The present method involves tandem reaction of α-aminoacetophenones and trans-β-nitrostyrenes, formation of two new C-C bonds and cleavage of one C-C bond in a single step. The salient features of the protocol are metal- and oxidant-free reaction conditions, broad substrate scope, and good yields.