13372-81-1

Usage

Uses

Used in Food Industry:
Cinnamaldehyde oxime is used as a food additive and flavoring agent for its distinctive sweet, spicy, and floral aroma, enhancing the taste and aroma of various food products.
Used in Perfumery and Fragrance Industry:
CINNAMALDEHYDE OXIME is used as a fragrance ingredient for its pleasant and complex scent, contributing to the creation of perfumes, soaps, and other scented products.
Used in Skincare Industry:
CINNAMALDEHYDE OXIME is used as an ingredient in skincare products for its aromatic properties, potentially offering sensory benefits in addition to its use in fragrances.
Used in Pharmaceutical Industry:
CINNAMALDEHYDE OXIME is used as a building block in the synthesis of various drugs and pharmaceutical compounds, leveraging its chemical properties for medicinal purposes.
Safety Considerations:
While CINNAMALDEHYDE OXIME is considered safe for use in small quantities, excessive exposure may cause irritation to the skin, eyes, and respiratory system, necessitating proper handling and usage guidelines.

InChI:InChI=1/C9H9NO/c11-10-8-4-7-9-5-2-1-3-6-9/h1-8,11H/b7-4-,10-8+

Upstream product

• 104-55-2 3-phenyl-propenal 
• 4360-51-4 cinnamylamine 
• 104-54-1 3-Phenylpropenol 
• 5470-11-1 hydroxylamine hydrochloride 
• 67-56-1 methanol 
• 14371-10-9 (E)-3-phenylpropenal 
• 1028432-12-3 C₂₂H₃₁NO₃SSi 
• 4335-60-8 (E)-cinnamylamine 
• 524-38-9 N-hydroxyphthalimide 
• 96-29-7 ethyl methyl ketone oxime 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 99441-44-8 3-phenyl-2-propenyl tetrahydro-2H-pyran-2-yl ether 
• 109283-53-6 trimethylsilyl cinnamyl ether 
• 57294-86-7 (3-azidoprop-1-en-1-yl)benzene 

Downstream Products

• 131605-01-1 5-acetoxymethyl-3-styrylisoxazoline 
• 1006-67-3 5-phenylisoxazole 
• 4360-47-8 cinnamonitrile 
• 105363-16-4 N-hydroxycinnamimidoyl chloride 
• 104-55-2 3-phenyl-propenal 
• 81588-43-4 diethyl <3-(ethoxyamino)-1-phenylallyl>phosphonate 
• 36914-22-4 2,3-Dibromo-3-phenyl-propionaldehyde oxime 
• 66894-04-0 2,3-dibromo-3-phenyl propanal 
• 26958-41-8 cinnamyl-1,3-dithiane 
• 621-79-4 cinnamamide 
• 1237-69-0 cinnamaldehyde 2,4-dinitrophenylhydrazone 
• 1216-15-5 cinnamaldehyde phenylhydrazone 
• 621-79-4 cinnamamide 
• 32555-96-7 4-stilbenecarboxaldehyde 

Relevant academic research and scientific papers

A rapid and efficient solvent-free microwave-assisted synthesis of pyrazolone derivatives containing substituted isoxazole ring

An efficient synthesis of 4-substituted pyrazolone derivatives was developed. 4-Substituted pyrazolone derivatives were synthesized in 78-97% yields starting from various 3-substituted isoxazole-5-carbaldehydes, ethyl acetoacetate and hydrazine under micr

Ru-Catalyzed [3 + 2] Cycloaddition of Nitrile Oxides and Electron-Rich Alkynes with Reversed Regioselectivity

Polarity reversal ("umpolung") of a functional group can override its inherent reactivity and lead to distinct bond-forming modes. Herein we describe a rarely studied cycloaddition between nitrile oxides and electron-rich alkynes with reversed regioselect

Site selective synthesis and anti-inflammatory evaluation of Spiro-isoxazoline stitched adducts of arteannuin B

A library of new spiroisoxazoline analogues of arteannuin B was synthesized through 1, 3-dipolar cycloaddition in stereoselective fashion and consequently screened for anti-inflammatory activity in RAW 264.7 macrophage cells. Three potent analogues (8i, 8 m, and 8n) were found to attenuate the LPS induced release of cytokines IL-6 and TNF-α more potently than the parent molecule. Also, the inhibition of LPS induced nitric oxide production in these cells show moderate to high efficacy. None of the three potent molecules have altered the viability of RAW 264.7 cells following 48 h incubation suggesting that the inhibition of cytokines and nitric oxide production exhibited in the cells was not due to toxicity. In addition, these compounds exhibit an IC50 range of 0.17 μM-1.57 μM and 0.09 μM-0.35 μM for the inhibition of IL-6 release and nitric oxide production respectively. The results disclose potent inhibition of pro-inflammatory mediators which are encouraging and warrant further investigations to develop new therapeutic agents for inflammatory diseases.

A Synergic Activity of Urea/Butyl Imidazolium Ionic Liquid Supported on UiO-66-NH2 Metal–Organic Framework for Synthesis of Oximes

An efficient supported ionic liquid catalyst is designed for condensation reaction of aldehydes and ketones. The Zr-based metal–organic framework (MOF), UiO-66-NH2, was initially functionalized with N,N′-dibutyl imidazolium ionic liquid (UiO-66-NH2-ILBr–), and then urea was attached to the ionic liquid (IL) to form a task-specific IL. Bromide was exchanged with tetrafluoroborate and the catalyst exhibits excellent performance for the synthesis of oximes. The ionic liquid/urea coupling showed a synergistic effect on the efficiency of the reaction. The supported catalyst system was recycled simply by filtration and reused for five times without significant decrease in its activity. The catalyst was characterized with PXRD, FTIR, TGA, XPS, BET, FE-SEM, EDS, elemental mapping and elemental analysis (CHN). Graphic Abstract: MOF/IL/urea catalytic system was used for the synthesis of oximes[Figure not available: see fulltext.].

Chlorotropylium Promoted Conversions of Oximes to Amides and Nitriles

Chlorotropylium chloride as a catalyst for the transformations of oximes, ketones, and aldehydes to their corresponding amides and nitriles in excellent yields (up to 99 %) and in short reaction times (mostly 10–15 min). Oximes were electrophilically attacked on the hydroxyl oxygen by chlorotropylium. The produced tropylium oxime ethers were the key intermediates, of which the ketoxime ether led to amide through Beckmann rearrangement, and the aldoxime ether led to nitrile by nitrogen base DBU assisted formal dehydration. This chlorotropylium activation protocol offered general, mild, and efficient avenues bifurcately from oximes to both amides and nitriles by one organocatalyst.

Design, synthesis and evaluation of novel levoglucosenone derivatives as promising anticancer agents

A series of levoglucosenone-derived 1,2,3-triazoles and isoxazoles featuring a flexible spacer between the heteroaromatic and anhydropyranose cores have been designed and synthesized following an hetero Michael // 1,3-dipolar cycloaddition path. The use o

Unusual Reactivity of 4-Vinyl Isoxazoles in the Copper-Mediated Synthesis of Pyridines, Employing DMSO as a One-Carbon Surrogate

An efficient protocol for the synthesis of nicotinate derivatives and tetrasubstituted pyridines through a copper-mediated cleavage of isoxazoles has been developed. The highlight of the work is the observation of an unusual reactivity of 4-vinyl isoxazoles under the reaction conditions. DMSO serves as a one-carbon surrogate generating an active methylene group during the reaction to form two C-C bonds. This protocol provides a facile and an expeditious approach for the assembly of densely substituted N-heterocyclic compounds.

Uncommon overoxidative catalytic activity in a new halo-tolerant alcohol dehydrogenase

Alcohol dehydrogenases (ADH) are versatile and useful enzymes employed as biocatalysts, especially for the selective oxidation of primary and secondary alcohols, and for the reduction of carbonyl moieties. A new alcohol dehydrogenase (HeADH-II) has been identified from the genome of the halo-adapted bacterium Halomonas elongata, which proved stable in the presence of polar organic solvents and salt exposure. Unusual for this class of enzymes, HeADH-II lacks enantiopreference and is capable of oxidizing both alcohols and aldehydes, enabling a direct overoxidation of primary alcohols to carboxylic acids. HeADH-II was coupled with a NADH-oxidase from Lactobacillus pentosus (LpNOX) to increase the process yields and allowing recycling of the cofactor. The enzymatic oxidation of primary alcohols was also paired with in situ condensation of the intermediate aldehydes with hydroxylamine to prepare the corresponding aldoximes, with particular attention to perillartine (a powerful sweetener), whose enzymatic synthesis starting from natural sources, leads to an equally natural product.

Synthetic method of cinnamonitrile

The invention discloses a synthetic method of cinnamonitrile, and cinnamaldehyde is used as a starting raw material to undergo condensation reaction and elimination reaction to synthesize the cinnamonitrile. According to the method disclosed by the invention, filter liquor is reused in the condensation reaction, so that zero emission of wastewater of the condensation reaction is realized, the yield of cinnamaldehyde oxime is increased, unit consumption of the cinnamaldehyde and hydroxylamine hydrochloride is reduced, and a byproduct sodium chloride or potassium chloride solid is produced; a catalyst is added in the elimination reaction reaction, the esterification capability of acetic anhydride is improved, elimination reaction rate is increased, and the unit consumption of the acetic anhydride is reduced.

Visible light-induced direct conversion of aldehydes into nitriles in aqueous medium using Co@g-C3N4 as photocatalyst

Unprecedented Co@g-C3N4 catalyzed visible light driven efficient conversion of a variety of aldehydes into corresponding nitriles is reported. Operational simplicity, excellent yield of pure products (87–94%), ambient reaction condition, using aqueous methanol as solvent, visible-light photocatalysis are the salient features of envisaged methodology for direct conversion of aldehydes into nitriles. Furthermore, reusability of Co@g-C3N4 was checked up to five runs and it was noticed that there was no substantial change in morphology as well as the catalytic efficiency of catalyst.