3669-32-7

Basic information

• Product Name: N-Hydroxycinnamamide
• Synonyms: cinnamoylhydroxamic acid;Benzeneacrylohydroximic acid;Cinnamohydroxamic acid;N-Hydroxy-3-phenyl-2-propenamide
• CAS NO: 3669-32-7
• Molecular Formula: C₉H₉NO₂
• Molecular Weight: 163.19
• Mol File: 3669-32-7.mol

Chemical Properties

• Boiling Point: 290.25°C (rough estimate)
• Flash Point: °C
• Appearance: /
• Density: 1.2021 (rough estimate)
• Refractive Index: 1.5460 (estimate)
• CAS DataBase Reference: N-Hydroxycinnamamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-Hydroxycinnamamide(3669-32-7)
• EPA Substance Registry System: N-Hydroxycinnamamide(3669-32-7)

Safety Data

• Hazardous Substances Data: 3669-32-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Applications:
Cinnamoylhydroxamic acid is used as a pharmaceutical agent for its diverse biological activities. It has the potential to inhibit specific enzymes, making it a candidate for the development of new drugs targeting various diseases.
Used in Cancer Research:
In the field of cancer research, cinnamoylhydroxamic acid is used as a cytotoxic and anti-proliferative agent. It has shown promise in inhibiting the growth and proliferation of cancer cells, warranting further investigation into its potential as an anticancer treatment.
Used in Industrial Applications:
Cinnamoylhydroxamic acid is also utilized in various industrial applications due to its ability to chelate metal ions. This property can be harnessed in processes that require the removal or stabilization of metal ions, contributing to the development of new technologies and products in different industries.

InChI:InChI=1/C9H9NO2/c11-9(10-12)7-6-8-4-2-1-3-5-8/h1-7,12H,(H,10,11)/b7-6+

Upstream product

• 14371-10-9 (E)-3-phenylpropenal 
• 599-71-3 piloty's acid 
• 103-36-6 ethyl 3-phenyl-2-propenoate 
• 102-92-1 cinnamoyl chloride 
• 140-10-3 cis-cinnamic acid 
• 103-26-4 methyl cinnamate 
• 1138-15-4 1-(3-phenyl-acryloyl)-1H-imidazole 
• 621-82-9 Cinnamic acid 
• 108761-28-0 (carbonic acid ethyl ester)-cinnamic acid-anhydride 

Downstream Products

• 80-05-7 BPA 
• 54891-84-8 1-(4-nitro-phenyl)-2-(3-styryl-[1,4,2]dioxazol-5-yl)-ethanone 
• 66437-42-1 1-(3-styryl-[1,4,2]dioxazol-5-yl)-pentan-2-one 

Relevant articles and documents

Synthesis, characterization and spectrophotometric determination of vanadium(V) with unsubstituted cinnamoyl hydroxamic acid

A series of hydroxamic acid and their derivatives play a key role in chemistry and metallochemistry in the subject of study of many synthetic experimental investigations. In this paper the synthesized compound were characterized and their structure was co

Silver-Catalyzed Acyl Nitrene Transfer Reactions Involving Dioxazolones: Direct Assembly of N-Acylureas

Dioxazolones and isocyanides are useful synthetic building blocks, and have attracted significant attention from researchers. However, the silver-catalyzed nitrene transfer reaction of dioxazolones has not been investigated to date. Herein, a silver-catalyzed acyl nitrene transfer reaction involving dioxazolones, isocyanides, and water was realized in the presence of Ag2O to afford a series of N-acylureas in moderate to good yields.

Water mediated procedure for preparation of stereoselective oximes as inhibitors of MRCK kinase

Stereoselective aldoximes, preferably Z form have been obtained from α-cyano substituted carbonyl conjugated alkenes. This reaction occurs through Michael addition type reaction followed by retro-Knoevenagel reaction without transition-metal catalysis via C–C bond cleavage. These oximes are evaluated against cancer cell lines employing mechanistic study. Two oximes showed significant cytotoxic activity, which through in silico studies were found to inhibit MRCK Kinase, responsible for metastatic spread of cancer mortality.

Synthesis and biological activity of salinomycin-hydroxamic acid conjugates

Several salinomycin-hydroxamic acid conjugates were designed and synthesized. Most conjugates showed better antiproliferative activities than salinomycin in HT-29 colon cancer, HGC-27 gastric cancer, and especially in MDA-MB-231 triple-negative human breast cancer cells. These conjugates are stable in cell culture media, and they showed much better biological activities than the 1:1 physical mixture with hydroxamic acids and salinomycin. The better membrane permeability and hydrolysis rate of the conjugates may lead to the activity improvements.

Benzoic hydroxamate-based iron complexes as model compounds for humic substances: Synthesis, characterization and algal growth experiments

A series of monomeric and dimeric FeIII complexes bearing benzoic hydroxamates as O,O-chelates has been prepared and characterized by elemental analysis, IR spectroscopy, UV-Vis spectroscopy, electrospray ionization mass spectrometry (ESI-MS), cyclic voltammetry, EPR spectroscopy and for some examples by X-ray diffraction analysis. The stability of the synthesized complexes in pure water and seawater was monitored over 24 h by means of UV-Vis spectrometry. The ability to release iron from the synthesized model complexes has been investigated with algae growth experiments.

Synthesis of (Z)-N-hydroxy-3-methoxy-3-phenylacrylamide as new selective inhibitor of hepatitis C virus replication

According to recently published results, cinnamic hydroxamic acid (CHA) inhibits replication of hepatitis C virus (HCV). We synthesized a structural analogue of CHA, i.e., (Z)-N-hydroxy-3-methoxy3-phenylacrylamide, which inhibited HCV replication five tim

Hydroxamic acids block replication of hepatitis c virus

Intrigued by the role of protein acetylation in hepatitis C virus (HCV) replication, we tested known histone deacetylase (HDAC) inhibitors and a focused library of structurally simple hydroxamic acids for inhibition of a HCV subgenomic replicon. While known HDAC inhibitors with varied inhibitory profiles proved to be either relatively toxic or ineffective, structure-activity relationship (SAR) studies on cinnamic hydroxamic acid and benzo[b]thiophen-2-hydroxamic acid gave rise to compounds 22 and 53, which showed potent and selective anti-HCV activity and therefore are promising starting points for further structural optimization and mechanistic studies.

Potent and selective inhibition of histone deacetylase 6 (HDAC6) does not require a surface-binding motif

Hydroxamic acids were designed, synthesized, and evaluated for their ability to selectively inhibit human histone deacetylase 6 (HDAC6). Several inhibitors, including compound 14 (BRD9757), exhibited excellent potency and selectivity despite the absence of a surface-binding motif. The binding of these highly efficient ligands for HDAC6 is rationalized via structure-activity relationships. These results demonstrate that high selectivity and potent inhibition of HDAC6 can be achieved through careful choice of linker element only.